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In episode 523, Rob hosts a rapid-fire lightning round of listener questions ranging from whether to focus on one or multiple businesses, finding the right amount of customer research, breaking through slow growth, and teaching entrepreneurship to kids.
The topics we cover
[4:38] If you were starting a business today and you were earlier on in your career, would you try multiple business ideas at once or go all-in on one?
[8:11] If building your first tiny product, like a WordPress plugin, what level of customer research should you do?
[10:56] What advice would you give to someone entering a somewhat competitive market?
[15:55] What questions would you be asking yourself if you had a slow-growing 12k MRR B2B SaaS?
[18:22] How would you go about offloading tier-one customer support?
[20:28] How do you feel about entrepreneurship being taught to children?
[22:24] What are things you noticed that bootstrappers commonly overlooked that are preventing them from achieving their goals?
[23:18] What are some of the biggest takeaways you can see across your portfolio of early-stage SaaS companies?
[25:01] Have you ever built a business that got a fairly large portion of its revenue from services instead of products, but not just you consulting?
[26:56] How do you prepare financially or otherwise for your retirement?
Links from the show
- MicroConf Connect
- SavvyCal
- Stay on Top of Your SaaS Metrics: Know What to Measure to Maintain Sustainable Growth – Craig Hewitt
- The 2020 State of Independent SaaS
- ZenFounder
- Indie Founder Bootcamp
- AudienceOps
- Castos Production (formerly Podcast Motor)
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Thanks for joining me this week on Startups For the Rest of Us. I am your host, Rob Walling, and this is Episode 523 where I answer a bunch of listener questions, have a rapid fire lightning round of listener questions. This episode is from MicroConf On Air a few weeks back and there were so many good questions. I spent about 30, 35 minutes answering them. It felt almost a natural Startups For the Rest of Us episode.
Once we dive in, you will hear a little bit of the intro music and hear me intro MicroConf On Air, which is a live stream that we do every Wednesday at 1:00 PM Eastern, 10:00 AM Pacific. If you haven’t checked it out, head to microconfonair.com and you can check out an episode. Sometimes I do live Q&A, taking questions from the chat in MicroConf Connect and in the YouTube comments. Other times, I have a conversation with a successful entrepreneur or an early stage founder. It’s a good time.
You can hear those MicroConf On Air episodes in a podcast feed at microconfpodcast.com if you’re curious to check them out in audio each week. Before we dive into that, I want to remind you that through MicroConf, we are putting on the first of its kind SaaS podcast awards. You can head to saaspodcastawards.com to nominate your favorite SaaS, or bootstrap, or podcast in one of four categories if you haven’t already gone and nominated. Or if you just want to nominate a couple of different shows, please head over to saaspodcastawards.com.
With that, let’s dive into this all listener question episode of Startups For the Rest of Us/MicroConf On Air, where I answer questions like how do you feel about entrepreneurship being taught to children? If you had a slow growing B2B SaaS app, what questions would you be asking yourself to break through the plateau? How do you prepare financially and otherwise for your retirement? What are things you notice that bootstrappers commonly overlook that are preventing them from achieving their goals? And how do I keep my hair looking good during the pandemic? It’s a real question. I probably should have given more of a joke answer. Somehow, I was in the flow of answering questions and I talked about that. With that, let’s dive in.
We are live and welcome to today’s episode of MicroConf On Air. I’m your host, Rob Walling, live streaming direct from my bunker library here in Minneapolis, Minnesota. Every Wednesday at 1:00 PM Eastern and producers, Andrew and I stream for 30 minutes and we cover topics related to building and growing ambitious SaaS startups that bring us freedom and purpose and allow us to value and maintain healthy relationships. We believe that showing up every day and shipping that next feature, that next piece of marketing copy closing that next sale is the way to build a sustainable company.
Thanks so much for joining me today. Today is an all ask-Rob episode. We’re going to be doing live Q&A. We have some good questions coming in on Twitter and in the MicroConf On Air channel in MicroConf Connect. If you’re not part of MicroConf Connect already, you should head into microsoftconnect.com. We have more than, I believe it’s over 1600 founders, bootstrappers, and mostly bootstrapped founders in there hanging out and having conversations like this every day. What I love is when I get into Connect and there’s a solid thread where I see a question and—I know the answer to this, or I have a thought on this, and I go in—and there’s already five amazing answers from other experienced founders who have done exactly this. I don’t even need to weigh in because the answers are good and they’re all legit. I am checking out some questions.
Today, I normally introduce my guest here, but you’ll know me as co-founder of Drip, and MicroConf, and TinySeed, Startups For the Rest of Us host and author of Start Small, Stay Small. I’m going to be answering a bunch of questions today, and it’s a good audience. It’s a great group of creators that are here in MicroConf Connect and participating on Twitter, and just into this MicroConf averse. I did an interview last week. If you haven’t checked this out on Indie Hackers, Courtland Allen and I had a conversation for about 1 hour and 10 minutes, solid, good questions from Courtland, good thoughts from him. I was just weighing, and we were just talking about frameworks, and advantages, and opportunities for launching SaaS in October of 2020. It was very specific to now. Not 5 years ago. Not 10 years ago. That’s spring on a few of the questions that we have today.
I’m going to dive in there. But first I’ve had a request already for a tell-a-joke. In true MicroConf dad joke tradition, this Fibonacci joke I’m going to tell you, it’s as bad as the last two you’ve heard combined. Normally at MicroConf, there’s all these groans. There’s groans, and laughs, and some people clap—slow clapping, golf clapping me—but without that, it loses a little bit.
My first question and today is from Noah Bragg. Thank you, producer Sander. It’s about 20 seconds late. Noah Bragg from MicroConf Connect asks, “If you were starting a business today—I’m going to assume it’s a SaaS company—and you were earlier in your career, would you try multiple business ideas at once, or go all-in on one?” This is a good question.
All-in is a deceptive phrase because I wouldn’t just dive in and say, oh, I have this idea. Oh, I’ve done some validation. Now, I’m going to spend the next six months going all-in on this idea. That’s not what I would do, but I would focus on launching and validating one idea at a time. Personally, I have a huge belief in focus. I’m not saying you can’t own multiple products at a time because I was the King of these micro portfolios back in the day, where I had 10 different products generating revenue for me. But I didn’t launch and grow 10 at once. I launched or acquired and grew one at a time, and then I figured out a way to make it sustainable, and more autopilots, a misnomer. But mostly an autopilot for now is how I’ll phrase it.
It’s on autopilot for 3-6 months. Until something happens, we’ll have to circle back. But focusing on one thing, you get into the headspace of it. All the information and content that you’re consuming, you can adapt or think through how you can apply it to that one thing. I would be doing a ton of validation at every step. When I first come up with an idea, I always think 90% this thing’s going to work. Then by 24 to 48-hour cooling off period before I register any domain, which is what I do these days, I wind up falling down to 10% or 20% certainty that this thing’s going to work.
Then typically I say, okay, what’s my next step to validate, how can I get myself to 25% or 30%? Oftentimes, it’s sending a few emails to people I know. It’s putting something on Twitter, asking opinions. It’s having face-to-face or in this case, these days, Zoom conversations. I might be putting up a landing page, driving traffic to it—whether it’s from my podcast, whether it’s from Twitter, whether it’s from running cold ads, which I did back in the day when we were validating Drip. I would just try to get that validation one step further, one step further.
That’s if I’m going to build maybe a larger, more novel product that doesn’t exist in the space today, and I’m trying to validate the idea itself. What if I know that there’s a gap in the WordPress plugin market, or that all the plugins that do polls on WordPress is just an example that they aren’t very good, or that I know that I can rank. It’s not that hard to rank high in the WordPress repository. There’s just a little bit of WordPress SEO. The algorithm is not as complex as Google. It’s not that smart.
Maybe I don’t want to validate that everybody needs a polling plugin. Maybe I want to validate that I can just rank higher. I get something in there or I email the top 10 poll plugins, especially the ones that haven’t been updated in two or three years, and I say, can I adopt your plugin or can I buy your plugin? These are ways that I would be going about. You don’t always have to build the thing from scratch, but the question of multiple or one, which should you focus on, in my opinion, unless you’re stair-stepping, and even with stair-stepping, I would focus on that. I was going to do an info product at the bottom end, or I would do that WordPress plugin or something as step one, and then I would build on it from there.
“How do you get your hair looking so good during a pandemic?” From Pat Foley. Thank you, sir. I did wear a mask and I get haircuts. That’s the honest answer. I had pandemic hair for the first four months because everything was shut down here, but we are still in—I don’t even know what—stage one lockdown where you can go to places. I went to the gym the other day. We wore a lot of face masks, but knock on wood, Minneapolis is not doing as poorly as many of the states around us. I appreciate the joking question, but that is the honest answer.
Question number two, also from Noah Bragg and MicroConf Connect. He’s following up on the above question. He says, ”If building your first tiny product like a WordPress plugin—” Hey, that was my example. I often say info products to WordPress plugin. There are Shopify ad-ons, there are Photoshop add-ons, there is a Google app store, Google Chrome store, things you can build. There’s a myriad of them. There are Magento ad-ons, we can go on and on. Anytime there’s an app store. Anytime there’s an ecosystem that has something that you’re not just battling to rank in Google for, these are the types of step one ideas I would encourage people to look at.
“If you’re building a first tiny product like a WordPress plugin, what level of customer research should you do? Is it more you see a problem and ship something? Or should you take a more cautious approach and try to validate further before shipping? I appreciate someone handing over money is the only real validation, but I’m trying to get an idea of how quickly you should move and whether it’s a case of trying lots of small bets. I hope that makes sense.” It does make sense. I would tend to act pretty quickly. I wouldn’t tend to do a bunch of customer validation calls or a bunch of customer development calls if I was going to do a small step one thing. I would validate almost in the Start Small, Stay Small approach. You go to startsmall.com, it’s my first book.
While the exact tools and exact numbers that I use there may not be accurate today because it’s 10 years old, the tactic there was you find a small niche or you find even not a small niche, but with an underserved corner that you can somehow measure the interest, whether that’s looking at a WordPress plugin and the repo and saying, oh, it has this many downloads. It must be a popular search term. Or you go to the Google keyword tool or you go to Ahrefs, or SEMrush, or Moz today and you say, oh, there are 5000 searches a month for this thing, and there are a couple of tools, but they’re not that great, or they’ve been abandoned.
There’s ways to validate just using free or lightly paid keyword tools and trying to find gaps in these markets. Even these days, there’s fewer gaps, but it’s places where people have launched and abandoned, or they’re not doing a good job and you see an angle. Then I would try to write some code quickly and move there.
Having a few customer development conversations or trying to figure out, hey, where do these people hang out that would use a plugin like this? Oh, they’re on Facebook. They’re in a couple of Facebook groups. Become a part of those Facebook groups and participate in them. They’re in these Slack groups. They’re in these forums. These discourse or discuss groups. There are ways to get this up to, I would say 20%, 30%, 40% validation, and to be able to write code and ship something in two weeks, three weeks.
For my bet, for my money, I’m probably going to write a little bit of code and get it out there. The learning starts with every bit of validation and frankly, getting something out there quickly in this—small niche is not the right word—but if it is a micro idea, I would lean towards action more than trying to validate for months and months.
Next question from Rami, he is King Ram Star on Twitter, “What advice would you give to someone entering a somewhat competitive market? Let’s say 5-10 direct competitors, which sounds ugly, but it’s less ugly than CRM, project management software, ESPs, marketing automation providers, where there are hundreds of players. Five to ten direct competitors, while that’s a thing, not the end of the world. More specifically, what would you do to out-muscle the competition when the resources are fairly equal, but the competition has social proof and social capital?”
I would not try to out-muscle the competition if I did not have a lot of money, or social capital, or social proof. You’re not going to muscle them. There’s this move in Jiu-Jitsu, or just the whole premise of Jiu-Jitsu is if someone has a bigger opponent than you, you don’t go head on with them and try to out strength them or out-muscle them because they will win. What you do is that you try to take their momentum when they punch you, when they lunge at you, and you peri and you use their momentum against them to get them on the ground, and then you grapple.
Similarly, I would use my opponent’s strengths against them. An example is you have 5-10 direct competitors. They have social proof and social capital. What are they doing wrong? Are you in their forums or their private Facebook groups? What are their customers complaining about? Where are they dropping the ball? Because companies that get to $1 million in ARR, $10 million in ARR, they tend to be leaving out sections of the market that they just have to ignore. They may be disappointing a certain subset of their customer-base or of their prospect-base.
It’s even better if you get big competitors because these are way easier to compete against. Companies like QuickBooks and PayPal. Think of Stripe launching at PayPal. Think of Xero launching at QuickBooks. Think of Drip launching against Marketo, Pardot, and Infusionsoft. They’re these big lumbering companies that aren’t shipping very often. They don’t have the amazing UX that you can build from the ground up. They aren’t just doing hand holding with their customers, they aren’t building the features that a subset or a vertical of the customer set might want.
I would start at the grassroots and I would start by trying to find 5 or 10 unhappy customers that I could interact with and say, what are you unhappy with? If you’ll get someone on the phone and they’ll just complain about everything—oh, the app’s impossible to use, and it’s too expensive, and no one listens to my phone calls, and I send them 10 emails a week and they don’t respond. That’s a toxic customer, they’re angry with everything all the time, they’re going to be unhappy with you too, goodbye.
But then you’ll get people who are, they’re pretty reasonable. They have ignored this corner of the market where photographers have special—I’m making this up. But photographers have special bookkeeping needs and their tax is calculated differently, and QuickBooks has just not listened. Suddenly it’s, oh, really? Who else could support photographers tax, bookkeeping, accounting needs? What other things have you tried to fix this? I’ve looked and there’s not an app that does this. Well, then it’s okay. Can I find 10 more photographers, or salon owners, or whoever it may be startup founders. That’s where I would start is, how do you find that subset if you have all this competition that is being left out.
The other thing I would think about, if you’re already in the space, you try to look for the hated competitor and become the opposite of them. If you can’t figure out a unique positioning—we’re the opposite of QuickBooks because we suck less, or we like QuickBooks but we’re for this particular vertical.
Think of SavvyCal. There’s Calendly and there’s all these big competitors. But look at what Derrick Reimer’s doing with SavvyCal. You go to savvycal.com to check it out. He’s basically saying it’s for busy startup founders and executives who have some pretty specific needs, and want to maybe guard maker time, and want to eliminate the awkwardness of sending a calendar invite. He’s taken a pretty specific tack there. He’s taking a unique position in the space. That’s one way. Another way in these competitive spaces is to have a unique traffic channel. That is, you look at what someone, maybe Ruben Gamez, is doing with Docsketch, which is e-signature, docsketch.com. It’s a terribly crowded space with literally billions and billions of dollars in market cap are in that space, and yet he has figured out a way to do amazing content marketing, amazing SEO, and just channel some of that traffic to where he is being highly successful in a competitive space.
To summarize, if I was going to go into a competitive space like this, I would look for a hated competitor. I would look for areas where that competitor is dropping the ball with either a specific audience or a specific group of people. I would look to position myself uniquely, or I would look for a unique traffic channel. With Drip, we had three of those four. Every one of those you have is better. If you only have one, you can still make it work, it’s just more of an uphill battle. Thanks for the question, Rami. I hope that was helpful.
The next question is from Garrett Lancaster, from MicroConf Connect. He said, “If you had a slow-growing $12,000 MRR, self-funded, B2B SaaS,” I love the specificity of this. “Doing about $150,000 a year, self-funded B2B SaaS, what questions would you be asking yourself?” I think he’s implying it’s slow-growing. What questions would you be asking yourself to get it growing faster? “How much do you think about retention versus conversion in this position?”
If my retention was not high, I have a problem. I’m going to use this phrase that is its product-market fit. I know that’s just a big, muddy, amorphous thing, but all it means is are people sticking around? Do people love your product? Do they stick around? Is your churn below 6%, 7%, your aggregate churn below that number? It depends on the price point, it depends on a bunch of stuff, but if you’re below 5%, then I would not be worried about retention now. I would be looking at increasing traffic and increasing conversion. The big question to ask is where’s the metrics gap? If you’re churning out 10%, 12%, 15% a month, that’s the number one problem. That’s what you have to fix before you do anything else.
That’s where I found myself when we were building Drip. We were a few months after launch and we had grown to $8000-$10,000 a month and we’re churning everybody out. That was a big retention problem. You can watch my MicroConf Talk, The Inside Story of Self-Funded SaaS Growth, I believe it’s called. It’s from, whatever, 2014, 2015.
If your retention is fine and people get on and then churn goes low for people, then, of course, it’s how much traffic, which your visitor-to-trial sign-up rate or visitor-to-trial should be, I’d like around 1%, if I’m asking for a credit card. I’d like about 15%, give or take, maybe 20%, if I’m not asking for a credit card. If I’m substantially below those, you have a trial conversion problem.
If I’m asking for a credit card upfront—trial to paid, I want to be between 40% and 60%. If I’m below 40%, I have a problem. You can look in the state of independent SaaS from 2020 and look at what other conversion rates are, or you can look at Craig Hewitt’s talk from MicroConf Europe in—was it just last year? It feels like 5 years ago. It was just last October. It’s something about viewing your metrics, maybe producers and they’re composed of that in the MicroConf Connect Slack. But he basically walks through rules of thumb and then says, these are the things to pay attention to if you’re below these rules of thumb. Otherwise, move on to the next thing.
At a certain point, my whole funnel is actually pretty solid. Now I’m just going to drive more traffic. I need to spend money on ads. I need to spend money on content. I need to do integrations. I need to go on podcasts, whatever it is, then let’s just see it. As you get more traffic, your conversion rates almost inevitably drop. Then you have to figure out how to then cater to those new folks.
The next question is still from Garrett. He says, “How would you go about offloading tier 1 customer support,” meaning frontline. Let’s say, it’s intercom chat, or it is usually just messaging or it’s email. “How would you go about offloading it when quality support/training is an integral part of your business model?” Everyone who asks this question says when quality support/training is an integral part of your business model—it’s an integral part of every early startup’s business model.
Much if I’m a developer, I write the best code in the world, I always feel like I can give the best support. In many cases, that’s relatively accurate. But how would you go about it? You find someone who’s really […] good. That’s what you do. You don’t settle for someone who isn’t going to learn your tool and who isn’t going to be ravenous about wanting to make people happy and learning your tool.
I had a non-technical, non-developer support guy that I worked with from, it was about 2011, 2012, all the way through when we were acquired. Then he worked with Drip through 2018, 2019. He was not a developer, but he figured out how to view source. He would go dig into people’s JavaScript and hack around in it. Obviously, on his client-side, he wouldn’t hack their website. I taught him how to use FTP. He learned how to edit HTML. He was just teaching himself this stuff.
He would sometimes ask me for a Loom, a quick screencast about stuff. For the most part, he went out and educated himself. In the early days, was he the fastest responder to tickets ever? Well, no because he was teaching himself stuff. But by the time he was working on Drip for a year or two, he knew the product. He knew how to answer support way better than any of us— way better than me, way better than the developers—and that’s the kind of person you’re looking for.
How did I find him? I went on Upwork and I went through two or three support people until I found a guy who was really good. He was working for a bunch of companies at once. He was doing 3 hours for me and 5 hours a week, then 10. Eventually, I said, I just want to hire you full-time, I was good to work with. We got along. We never did video chat, we never actually met in person. He lived in Mexico and that was it.
Many of you, if you emailed Drip, Andy responded to every support request for the first 3 ½ years of Drip’s life. I think it was 3 ½, maybe it’s 2 ½. Every single frontline support was just one guy, Andy. That’s what you do. That’s what I would do today. Hire good people.
The next question from Pablo in MicroConf Connect, “How do you feel about entrepreneurship being taught to children? Do you think it should be taught? Have you witnessed good execution of teaching children entrepreneurship?” I feel good about it with a caveat. My son had a course in eighth grade or maybe it was freshman in high school. It was teaching him stuff about intellectual property. It was trademarks and it was logos and he had to design a logo. We’re they teaching him everything we learned in MicroConf? Of course not. But did he learn some basics that he didn’t know the difference between trademark, and copyright, and some basic fundamentals? I thought that was good.
All of us in high school/college should learn something about entrepreneurship, something about how businesses work, something about personal finance, to be honest. Why is that not taught in school? Why do none of us know how the stock market works? You have to go do educate yourself. You have to go seek that out. How to just simply find a budget and stick to it. To me, it’s a real problem that is not taught to—whether it’s our children or probably our high schoolers.
We have Civics and Economics where we learn about the economy and nobody pays attention about the three branches of government. I’m only joking. Of course, people pay attention. But personal finance and something about entrepreneurship, they should be exposed to it to know this is what entrepreneurship might look like.
There are examples of people who are making caramels or cookies in a local kitchen and you could do a tech startup and raise funding or not. Do you think just being exposed to that would be super helpful for children? Yes, I do think it should be taught. I can’t think of an amazing example of anyone who’s done it.
I will give a spoiler that—I don’t know if she’s announced this—but Dr. Sherry Walling, my wife is writing a book called, Raising Entrepreneurial Children or something like to that effect. That’s the working title. Go to zenfounder.com and sign up for her email list if you want to hear about it. Of course, I’ll be talking about in the future. I may even contribute a chapter or two. Sherry and I had a ZenFounder episode a while back. Zenfinder episode in the first maybe 30 episodes that was all about raising entrepreneurial kids, if you want to check that out.
Next question, “What are things you notice that bootstrappers commonly overlook that are preventing them from achieving their goals?” A lot of bootstrappers overlook the fact that you have to market, that it’s not about building products. Bootstrappers don’t pay enough attention to their metrics, their analytics, or their metrics. They don’t even know what’s working. You ask someone a question and they say, what’s working is word of mouth. Word of mouth is usually the wrong answer.
There’s a lot of mistakes that people make. MicroConf talks point this out. I would say listening to Startups For the Rest of Us, even nugget.one, which is a pretty interesting website, Justin Vincent has a pretty interesting course there. There are definitely the common mistakes before finding an audience building before validating—not an audience—but a customer base building before validating. These are a lot of things that people do. People give up too easily. They build something, it goes to a plateau, and they give up instead of actually doing the hard work, it’s a lot more hard work than people realize.
Another question. This is from Vijay Goel from Chefalytics. He says, “What are some of the biggest takeaways you can see across your portfolio of early-stage SaaS companies? Is it one or two winners generating most returns? VC style? Is it steady progress by most? Will the majority be default alive businesses?” The answer is yes. The vast majority are already default alive businesses.
Every one of the 13 companies of batch 2 is default alive, pretty sure. If I were to put a number to 70% of batch 1, maybe 80% are default alive. So yes, default alive, all of them are making steady progress. Of 23 companies, there’s maybe two or three that are still not growing— two, three, four—it’s a small number. Maybe 10%, 15% are still trying to find that repeatable channel, still trying to find that repeatable customer base, but it is definitely steady progress. I don’t think it’s going to be winner-take-all. But, to be honest, I shouldn’t say I don’t think it will.
Einar did analysis of a bunch of SaaS apps. He got a bunch of anonymized data and he looked backwards over the last five years. If you do look at returns, it was not winner-take-all, but it was definitely a power law. Power law just means there is a small number who get 10 or 100 times larger than the others. In that case, yes, that era in that sense, yes, we may get there. I’ve been doing this for 15 years. There’s a reason MicroConf, and Startups for the Rest of Us, and my books, and TinySeed exist. It’s not to help the winner-take-all. It’s to help everyone. I want to raise the tide so all the boats go up. Yes, even if the returns are generated in that VC style winner-take-all, I will still be around and still be here to help everyone involved.
The question from Patrick Foley, “Have you ever built a business that got a fairly large portion of its revenue from services instead of products, but not just you consulting?” Yes. One I can think of, it’s called CMS Themer. It was a productized service before that term existed. It was at www.cmsthemer.com. I don’t even know if there’s a website there anymore. I ran it for about 18 months to 2 years. I acquired it from someone who wanted to shut it down. I knew how to rank it in Google. I got it to the top first page of Google for WordPress theming and some other things were present, Drupal and Joomla. Then I just had an agency—I believe they were in India—it was somewhere that I could outsource to for cheap. I marked them up 100%. I would charge $500 for you to send me a PSD, I would send it to my agency in India, they’d charge me $250 to turn it into a theme. I would send it back and make $500. It wasn’t a productized subscription service, but it was these one-off themes.
As custom stuff happened, we would increase the price. If you needed something more responsive back in 2009, it was obviously more money. Yeah, I have. It was fine. It was a little, quite a bit of hassle. I had that along with a bunch of software products and ecommerce and stuff. I’m trying to think if there are any takeaways I have from that. Productized services are a great way to get started quick these days, especially subscription services. You look at Audience Ops from Brian Casel, or you look at Podcast Motor from Craig Hewitt and there are other examples.
They get up to whatever $20,000, $30,000, $40,000 a month in no time. And then yes, you have to have a process in place, you have to have people to manage. It’s not a software product, but you learn a lot. It’s probably 70%, 80% the same as building a SaaS. Then Craig Hewitt levered it up to then acquire WordPress plugin to then build Castos and now, everything’s combined into one. It’s like a match made in heaven and it’s like a chef’s kiss to the stair-step approach in a way is building these businesses and building on top of each other.
And now one more question from Christoph Engelhardt, “How do you prepare financially or otherwise, for your retirement?” It’s a good question. I like personal finance. I’m a bit of a nerd with this stuff. Before I had sold Drip, I was contributing to retirement for most years—for both Sherry and I—putting them in the US. There are IRAs or 401(k)s.
I did stop. I will admit at the worst times of Drip, when it was growing fast and we had cash crunches, I stopped contributing to retirement. My bet was that Drip would make enough money in the end, whether through an acquisition or whether through throwing off cash, that it would make up for that. The bet worked out for me. It’s not going to work out for everyone. But by the time we sold Drip, I believed between Sherry and my retirement accounts, we had about $300,000, which I was in my late thirties. Is that right? I might’ve been in my early forties. I would prefer to have more by then, but when I looked at compounding and how it was growing, we would have had I’d say a couple million when we retired. But I also counted on having a lot more earnings and being able to put money in.
For me, it’s about saving early. I started contributing right out of college. In fact, if you can do anything for your kids, or nephews, or whatever—I’ll comment on the US because I know the retirement system here—but if there is a RHYTTAC-shielded retirement account, an individual retirement account called an IRA here, as soon as your kids get any income, match what they make, give and put the money. You can put up to $5500 as of this taping into a retirement account.
If you can put it in when they’re 15 or 16, compound interest is the eighth wonder of the world. I believe Albert Einstein said that. The earlier you get, if you invest at 15 versus 30, you get two more doublings of that, if you invest in the stock market. Put it all in high-risk stuff. I would be 100% in stocks. If you’re making 8% per year, then it’s going to double every 9 years. If you make 9% per year, it’s going double every 8 years. From 15% to 30%, you get almost two doubles of that. If you put in $5000, it becomes $10,000, then $20,000 by the time they’re 30. If they don’t contribute until 30, they have to contribute $20,000 to have the same impact that you do when they’re that young.
I started putting money in when I was 22, and just a little bit. I didn’t have much money. I wasn’t making much. I make $15, $17 out of college per hour. But I started putting $50, $100 a month away as early as I possibly could.
Thanks so much for joining me today. That is going to wrap us up. Thanks for hanging out with me a little longer. Last joke, can you imagine if one day MicroConf acquired Microsoft? Ooh, that was a misspoke. Can you imagine if one day Microsoft acquired WIWORK and named it Microsoft Office?
We do have some special podcasting stuff coming up soon. We’re going to have some voting and some nominations. I’m teasing that, so keep your eye out at microconf.com and thank you as always to Hey and Stripe for supporting MicroConf Headlines partners for the year. We love working with them. Thanks for joining me. I’ll see you next week.
Once we dive in, you will hear a little bit of the intro music and hear me intro MicroConf On Air, which is a live stream that we do every Wednesday at 1:00 PM Eastern, 10:00 AM Pacific. If you haven’t checked it out, head to microconfonair.com and you can check out an episode. Sometimes I do live Q&A, taking questions from the chat in MicroConf Connect and in the YouTube comments. Other times, I have a conversation with a successful entrepreneur or an early stage founder. It’s a good time.
You can hear those MicroConf On Air episodes in a podcast feed at microconfpodcast.com if you’re curious to check them out in audio each week. Before we dive into that, I want to remind you that through MicroConf, we are putting on the first of its kind SaaS podcast awards. You can head to saaspodcastawards.com to nominate your favorite SaaS, or bootstrap, or podcast in one of four categories if you haven’t already gone and nominated. Or if you just want to nominate a couple of different shows, please head over to saaspodcastawards.com.
With that, let’s dive into this all listener question episode of Startups For the Rest of Us/MicroConf On Air, where I answer questions like how do you feel about entrepreneurship being taught to children? If you had a slow growing B2B SaaS app, what questions would you be asking yourself to break through the plateau? How do you prepare financially and otherwise for your retirement? What are things you notice that bootstrappers commonly overlook that are preventing them from achieving their goals? And how do I keep my hair looking good during the pandemic? It’s a real question. I probably should have given more of a joke answer. Somehow, I was in the flow of answering questions and I talked about that. With that, let’s dive in.
We are live and welcome to today’s episode of MicroConf On Air. I’m your host, Rob Walling, live streaming direct from my bunker library here in Minneapolis, Minnesota. Every Wednesday at 1:00 PM Eastern and producers, Andrew and I stream for 30 minutes and we cover topics related to building and growing ambitious SaaS startups that bring us freedom and purpose and allow us to value and maintain healthy relationships. We believe that showing up every day and shipping that next feature, that next piece of marketing copy closing that next sale is the way to build a sustainable company.
Thanks so much for joining me today. Today is an all ask-Rob episode. We’re going to be doing live Q&A. We have some good questions coming in on Twitter and in the MicroConf On Air channel in MicroConf Connect. If you’re not part of MicroConf Connect already, you should head into microsoftconnect.com. We have more than, I believe it’s over 1600 founders, bootstrappers, and mostly bootstrapped founders in there hanging out and having conversations like this every day. What I love is when I get into Connect and there’s a solid thread where I see a question and—I know the answer to this, or I have a thought on this, and I go in—and there’s already five amazing answers from other experienced founders who have done exactly this. I don’t even need to weigh in because the answers are good and they’re all legit. I am checking out some questions.
Today, I normally introduce my guest here, but you’ll know me as co-founder of Drip, and MicroConf, and TinySeed, Startups For the Rest of Us host and author of Start Small, Stay Small. I’m going to be answering a bunch of questions today, and it’s a good audience. It’s a great group of creators that are here in MicroConf Connect and participating on Twitter, and just into this MicroConf averse. I did an interview last week. If you haven’t checked this out on Indie Hackers, Courtland Allen and I had a conversation for about 1 hour and 10 minutes, solid, good questions from Courtland, good thoughts from him. I was just weighing, and we were just talking about frameworks, and advantages, and opportunities for launching SaaS in October of 2020. It was very specific to now. Not 5 years ago. Not 10 years ago. That’s spring on a few of the questions that we have today.
I’m going to dive in there. But first I’ve had a request already for a tell-a-joke. In true MicroConf dad joke tradition, this Fibonacci joke I’m going to tell you, it’s as bad as the last two you’ve heard combined. Normally at MicroConf, there’s all these groans. There’s groans, and laughs, and some people clap—slow clapping, golf clapping me—but without that, it loses a little bit.
My first question and today is from Noah Bragg. Thank you, producer Sander. It’s about 20 seconds late. Noah Bragg from MicroConf Connect asks, “If you were starting a business today—I’m going to assume it’s a SaaS company—and you were earlier in your career, would you try multiple business ideas at once, or go all-in on one?” This is a good question.
All-in is a deceptive phrase because I wouldn’t just dive in and say, oh, I have this idea. Oh, I’ve done some validation. Now, I’m going to spend the next six months going all-in on this idea. That’s not what I would do, but I would focus on launching and validating one idea at a time. Personally, I have a huge belief in focus. I’m not saying you can’t own multiple products at a time because I was the King of these micro portfolios back in the day, where I had 10 different products generating revenue for me. But I didn’t launch and grow 10 at once. I launched or acquired and grew one at a time, and then I figured out a way to make it sustainable, and more autopilots, a misnomer. But mostly an autopilot for now is how I’ll phrase it.
It’s on autopilot for 3-6 months. Until something happens, we’ll have to circle back. But focusing on one thing, you get into the headspace of it. All the information and content that you’re consuming, you can adapt or think through how you can apply it to that one thing. I would be doing a ton of validation at every step. When I first come up with an idea, I always think 90% this thing’s going to work. Then by 24 to 48-hour cooling off period before I register any domain, which is what I do these days, I wind up falling down to 10% or 20% certainty that this thing’s going to work.
Then typically I say, okay, what’s my next step to validate, how can I get myself to 25% or 30%? Oftentimes, it’s sending a few emails to people I know. It’s putting something on Twitter, asking opinions. It’s having face-to-face or in this case, these days, Zoom conversations. I might be putting up a landing page, driving traffic to it—whether it’s from my podcast, whether it’s from Twitter, whether it’s from running cold ads, which I did back in the day when we were validating Drip. I would just try to get that validation one step further, one step further.
That’s if I’m going to build maybe a larger, more novel product that doesn’t exist in the space today, and I’m trying to validate the idea itself. What if I know that there’s a gap in the WordPress plugin market, or that all the plugins that do polls on WordPress is just an example that they aren’t very good, or that I know that I can rank. It’s not that hard to rank high in the WordPress repository. There’s just a little bit of WordPress SEO. The algorithm is not as complex as Google. It’s not that smart.
Maybe I don’t want to validate that everybody needs a polling plugin. Maybe I want to validate that I can just rank higher. I get something in there or I email the top 10 poll plugins, especially the ones that haven’t been updated in two or three years, and I say, can I adopt your plugin or can I buy your plugin? These are ways that I would be going about. You don’t always have to build the thing from scratch, but the question of multiple or one, which should you focus on, in my opinion, unless you’re stair-stepping, and even with stair-stepping, I would focus on that. I was going to do an info product at the bottom end, or I would do that WordPress plugin or something as step one, and then I would build on it from there.
“How do you get your hair looking so good during a pandemic?” From Pat Foley. Thank you, sir. I did wear a mask and I get haircuts. That’s the honest answer. I had pandemic hair for the first four months because everything was shut down here, but we are still in—I don’t even know what—stage one lockdown where you can go to places. I went to the gym the other day. We wore a lot of face masks, but knock on wood, Minneapolis is not doing as poorly as many of the states around us. I appreciate the joking question, but that is the honest answer.
Question number two, also from Noah Bragg and MicroConf Connect. He’s following up on the above question. He says, ”If building your first tiny product like a WordPress plugin—” Hey, that was my example. I often say info products to WordPress plugin. There are Shopify ad-ons, there are Photoshop add-ons, there is a Google app store, Google Chrome store, things you can build. There’s a myriad of them. There are Magento ad-ons, we can go on and on. Anytime there’s an app store. Anytime there’s an ecosystem that has something that you’re not just battling to rank in Google for, these are the types of step one ideas I would encourage people to look at.
“If you’re building a first tiny product like a WordPress plugin, what level of customer research should you do? Is it more you see a problem and ship something? Or should you take a more cautious approach and try to validate further before shipping? I appreciate someone handing over money is the only real validation, but I’m trying to get an idea of how quickly you should move and whether it’s a case of trying lots of small bets. I hope that makes sense.” It does make sense. I would tend to act pretty quickly. I wouldn’t tend to do a bunch of customer validation calls or a bunch of customer development calls if I was going to do a small step one thing. I would validate almost in the Start Small, Stay Small approach. You go to startsmall.com, it’s my first book.
While the exact tools and exact numbers that I use there may not be accurate today because it’s 10 years old, the tactic there was you find a small niche or you find even not a small niche, but with an underserved corner that you can somehow measure the interest, whether that’s looking at a WordPress plugin and the repo and saying, oh, it has this many downloads. It must be a popular search term. Or you go to the Google keyword tool or you go to Ahrefs, or SEMrush, or Moz today and you say, oh, there are 5000 searches a month for this thing, and there are a couple of tools, but they’re not that great, or they’ve been abandoned.
There’s ways to validate just using free or lightly paid keyword tools and trying to find gaps in these markets. Even these days, there’s fewer gaps, but it’s places where people have launched and abandoned, or they’re not doing a good job and you see an angle. Then I would try to write some code quickly and move there.
Having a few customer development conversations or trying to figure out, hey, where do these people hang out that would use a plugin like this? Oh, they’re on Facebook. They’re in a couple of Facebook groups. Become a part of those Facebook groups and participate in them. They’re in these Slack groups. They’re in these forums. These discourse or discuss groups. There are ways to get this up to, I would say 20%, 30%, 40% validation, and to be able to write code and ship something in two weeks, three weeks.
For my bet, for my money, I’m probably going to write a little bit of code and get it out there. The learning starts with every bit of validation and frankly, getting something out there quickly in this—small niche is not the right word—but if it is a micro idea, I would lean towards action more than trying to validate for months and months.
Next question from Rami, he is King Ram Star on Twitter, “What advice would you give to someone entering a somewhat competitive market? Let’s say 5-10 direct competitors, which sounds ugly, but it’s less ugly than CRM, project management software, ESPs, marketing automation providers, where there are hundreds of players. Five to ten direct competitors, while that’s a thing, not the end of the world. More specifically, what would you do to out-muscle the competition when the resources are fairly equal, but the competition has social proof and social capital?”
I would not try to out-muscle the competition if I did not have a lot of money, or social capital, or social proof. You’re not going to muscle them. There’s this move in Jiu-Jitsu, or just the whole premise of Jiu-Jitsu is if someone has a bigger opponent than you, you don’t go head on with them and try to out strength them or out-muscle them because they will win. What you do is that you try to take their momentum when they punch you, when they lunge at you, and you peri and you use their momentum against them to get them on the ground, and then you grapple.
Similarly, I would use my opponent’s strengths against them. An example is you have 5-10 direct competitors. They have social proof and social capital. What are they doing wrong? Are you in their forums or their private Facebook groups? What are their customers complaining about? Where are they dropping the ball? Because companies that get to $1 million in ARR, $10 million in ARR, they tend to be leaving out sections of the market that they just have to ignore. They may be disappointing a certain subset of their customer-base or of their prospect-base.
It’s even better if you get big competitors because these are way easier to compete against. Companies like QuickBooks and PayPal. Think of Stripe launching at PayPal. Think of Xero launching at QuickBooks. Think of Drip launching against Marketo, Pardot, and Infusionsoft. They’re these big lumbering companies that aren’t shipping very often. They don’t have the amazing UX that you can build from the ground up. They aren’t just doing hand holding with their customers, they aren’t building the features that a subset or a vertical of the customer set might want.
I would start at the grassroots and I would start by trying to find 5 or 10 unhappy customers that I could interact with and say, what are you unhappy with? If you’ll get someone on the phone and they’ll just complain about everything—oh, the app’s impossible to use, and it’s too expensive, and no one listens to my phone calls, and I send them 10 emails a week and they don’t respond. That’s a toxic customer, they’re angry with everything all the time, they’re going to be unhappy with you too, goodbye.
But then you’ll get people who are, they’re pretty reasonable. They have ignored this corner of the market where photographers have special—I’m making this up. But photographers have special bookkeeping needs and their tax is calculated differently, and QuickBooks has just not listened. Suddenly it’s, oh, really? Who else could support photographers tax, bookkeeping, accounting needs? What other things have you tried to fix this? I’ve looked and there’s not an app that does this. Well, then it’s okay. Can I find 10 more photographers, or salon owners, or whoever it may be startup founders. That’s where I would start is, how do you find that subset if you have all this competition that is being left out.
The other thing I would think about, if you’re already in the space, you try to look for the hated competitor and become the opposite of them. If you can’t figure out a unique positioning—we’re the opposite of QuickBooks because we suck less, or we like QuickBooks but we’re for this particular vertical.
Think of SavvyCal. There’s Calendly and there’s all these big competitors. But look at what Derrick Reimer’s doing with SavvyCal. You go to savvycal.com to check it out. He’s basically saying it’s for busy startup founders and executives who have some pretty specific needs, and want to maybe guard maker time, and want to eliminate the awkwardness of sending a calendar invite. He’s taken a pretty specific tack there. He’s taking a unique position in the space. That’s one way. Another way in these competitive spaces is to have a unique traffic channel. That is, you look at what someone, maybe Ruben Gamez, is doing with Docsketch, which is e-signature, docsketch.com. It’s a terribly crowded space with literally billions and billions of dollars in market cap are in that space, and yet he has figured out a way to do amazing content marketing, amazing SEO, and just channel some of that traffic to where he is being highly successful in a competitive space.
To summarize, if I was going to go into a competitive space like this, I would look for a hated competitor. I would look for areas where that competitor is dropping the ball with either a specific audience or a specific group of people. I would look to position myself uniquely, or I would look for a unique traffic channel. With Drip, we had three of those four. Every one of those you have is better. If you only have one, you can still make it work, it’s just more of an uphill battle. Thanks for the question, Rami. I hope that was helpful.
The next question is from Garrett Lancaster, from MicroConf Connect. He said, “If you had a slow-growing $12,000 MRR, self-funded, B2B SaaS,” I love the specificity of this. “Doing about $150,000 a year, self-funded B2B SaaS, what questions would you be asking yourself?” I think he’s implying it’s slow-growing. What questions would you be asking yourself to get it growing faster? “How much do you think about retention versus conversion in this position?”
If my retention was not high, I have a problem. I’m going to use this phrase that is its product-market fit. I know that’s just a big, muddy, amorphous thing, but all it means is are people sticking around? Do people love your product? Do they stick around? Is your churn below 6%, 7%, your aggregate churn below that number? It depends on the price point, it depends on a bunch of stuff, but if you’re below 5%, then I would not be worried about retention now. I would be looking at increasing traffic and increasing conversion. The big question to ask is where’s the metrics gap? If you’re churning out 10%, 12%, 15% a month, that’s the number one problem. That’s what you have to fix before you do anything else.
That’s where I found myself when we were building Drip. We were a few months after launch and we had grown to $8000-$10,000 a month and we’re churning everybody out. That was a big retention problem. You can watch my MicroConf Talk, The Inside Story of Self-Funded SaaS Growth, I believe it’s called. It’s from, whatever, 2014, 2015.
If your retention is fine and people get on and then churn goes low for people, then, of course, it’s how much traffic, which your visitor-to-trial sign-up rate or visitor-to-trial should be, I’d like around 1%, if I’m asking for a credit card. I’d like about 15%, give or take, maybe 20%, if I’m not asking for a credit card. If I’m substantially below those, you have a trial conversion problem.
If I’m asking for a credit card upfront—trial to paid, I want to be between 40% and 60%. If I’m below 40%, I have a problem. You can look in the state of independent SaaS from 2020 and look at what other conversion rates are, or you can look at Craig Hewitt’s talk from MicroConf Europe in—was it just last year? It feels like 5 years ago. It was just last October. It’s something about viewing your metrics, maybe producers and they’re composed of that in the MicroConf Connect Slack. But he basically walks through rules of thumb and then says, these are the things to pay attention to if you’re below these rules of thumb. Otherwise, move on to the next thing.
At a certain point, my whole funnel is actually pretty solid. Now I’m just going to drive more traffic. I need to spend money on ads. I need to spend money on content. I need to do integrations. I need to go on podcasts, whatever it is, then let’s just see it. As you get more traffic, your conversion rates almost inevitably drop. Then you have to figure out how to then cater to those new folks.
The next question is still from Garrett. He says, “How would you go about offloading tier 1 customer support,” meaning frontline. Let’s say, it’s intercom chat, or it is usually just messaging or it’s email. “How would you go about offloading it when quality support/training is an integral part of your business model?” Everyone who asks this question says when quality support/training is an integral part of your business model—it’s an integral part of every early startup’s business model.
Much if I’m a developer, I write the best code in the world, I always feel like I can give the best support. In many cases, that’s relatively accurate. But how would you go about it? You find someone who’s really […] good. That’s what you do. You don’t settle for someone who isn’t going to learn your tool and who isn’t going to be ravenous about wanting to make people happy and learning your tool.
I had a non-technical, non-developer support guy that I worked with from, it was about 2011, 2012, all the way through when we were acquired. Then he worked with Drip through 2018, 2019. He was not a developer, but he figured out how to view source. He would go dig into people’s JavaScript and hack around in it. Obviously, on his client-side, he wouldn’t hack their website. I taught him how to use FTP. He learned how to edit HTML. He was just teaching himself this stuff.
He would sometimes ask me for a Loom, a quick screencast about stuff. For the most part, he went out and educated himself. In the early days, was he the fastest responder to tickets ever? Well, no because he was teaching himself stuff. But by the time he was working on Drip for a year or two, he knew the product. He knew how to answer support way better than any of us— way better than me, way better than the developers—and that’s the kind of person you’re looking for.
How did I find him? I went on Upwork and I went through two or three support people until I found a guy who was really good. He was working for a bunch of companies at once. He was doing 3 hours for me and 5 hours a week, then 10. Eventually, I said, I just want to hire you full-time, I was good to work with. We got along. We never did video chat, we never actually met in person. He lived in Mexico and that was it.
Many of you, if you emailed Drip, Andy responded to every support request for the first 3 ½ years of Drip’s life. I think it was 3 ½, maybe it’s 2 ½. Every single frontline support was just one guy, Andy. That’s what you do. That’s what I would do today. Hire good people.
The next question from Pablo in MicroConf Connect, “How do you feel about entrepreneurship being taught to children? Do you think it should be taught? Have you witnessed good execution of teaching children entrepreneurship?” I feel good about it with a caveat. My son had a course in eighth grade or maybe it was freshman in high school. It was teaching him stuff about intellectual property. It was trademarks and it was logos and he had to design a logo. We’re they teaching him everything we learned in MicroConf? Of course not. But did he learn some basics that he didn’t know the difference between trademark, and copyright, and some basic fundamentals? I thought that was good.
All of us in high school/college should learn something about entrepreneurship, something about how businesses work, something about personal finance, to be honest. Why is that not taught in school? Why do none of us know how the stock market works? You have to go do educate yourself. You have to go seek that out. How to just simply find a budget and stick to it. To me, it’s a real problem that is not taught to—whether it’s our children or probably our high schoolers.
We have Civics and Economics where we learn about the economy and nobody pays attention about the three branches of government. I’m only joking. Of course, people pay attention. But personal finance and something about entrepreneurship, they should be exposed to it to know this is what entrepreneurship might look like.
There are examples of people who are making caramels or cookies in a local kitchen and you could do a tech startup and raise funding or not. Do you think just being exposed to that would be super helpful for children? Yes, I do think it should be taught. I can’t think of an amazing example of anyone who’s done it.
I will give a spoiler that—I don’t know if she’s announced this—but Dr. Sherry Walling, my wife is writing a book called, Raising Entrepreneurial Children or something like to that effect. That’s the working title. Go to zenfounder.com and sign up for her email list if you want to hear about it. Of course, I’ll be talking about in the future. I may even contribute a chapter or two. Sherry and I had a ZenFounder episode a while back. Zenfinder episode in the first maybe 30 episodes that was all about raising entrepreneurial kids, if you want to check that out.
Next question, “What are things you notice that bootstrappers commonly overlook that are preventing them from achieving their goals?” A lot of bootstrappers overlook the fact that you have to market, that it’s not about building products. Bootstrappers don’t pay enough attention to their metrics, their analytics, or their metrics. They don’t even know what’s working. You ask someone a question and they say, what’s working is word of mouth. Word of mouth is usually the wrong answer.
There’s a lot of mistakes that people make. MicroConf talks point this out. I would say listening to Startups For the Rest of Us, even nugget.one, which is a pretty interesting website, Justin Vincent has a pretty interesting course there. There are definitely the common mistakes before finding an audience building before validating—not an audience—but a customer base building before validating. These are a lot of things that people do. People give up too easily. They build something, it goes to a plateau, and they give up instead of actually doing the hard work, it’s a lot more hard work than people realize.
Another question. This is from Vijay Goel from Chefalytics. He says, “What are some of the biggest takeaways you can see across your portfolio of early-stage SaaS companies? Is it one or two winners generating most returns? VC style? Is it steady progress by most? Will the majority be default alive businesses?” The answer is yes. The vast majority are already default alive businesses.
Every one of the 13 companies of batch 2 is default alive, pretty sure. If I were to put a number to 70% of batch 1, maybe 80% are default alive. So yes, default alive, all of them are making steady progress. Of 23 companies, there’s maybe two or three that are still not growing— two, three, four—it’s a small number. Maybe 10%, 15% are still trying to find that repeatable channel, still trying to find that repeatable customer base, but it is definitely steady progress. I don’t think it’s going to be winner-take-all. But, to be honest, I shouldn’t say I don’t think it will.
Einar did analysis of a bunch of SaaS apps. He got a bunch of anonymized data and he looked backwards over the last five years. If you do look at returns, it was not winner-take-all, but it was definitely a power law. Power law just means there is a small number who get 10 or 100 times larger than the others. In that case, yes, that era in that sense, yes, we may get there. I’ve been doing this for 15 years. There’s a reason MicroConf, and Startups for the Rest of Us, and my books, and TinySeed exist. It’s not to help the winner-take-all. It’s to help everyone. I want to raise the tide so all the boats go up. Yes, even if the returns are generated in that VC style winner-take-all, I will still be around and still be here to help everyone involved.
The question from Patrick Foley, “Have you ever built a business that got a fairly large portion of its revenue from services instead of products, but not just you consulting?” Yes. One I can think of, it’s called CMS Themer. It was a productized service before that term existed. It was at www.cmsthemer.com. I don’t even know if there’s a website there anymore. I ran it for about 18 months to 2 years. I acquired it from someone who wanted to shut it down. I knew how to rank it in Google. I got it to the top first page of Google for WordPress theming and some other things were present, Drupal and Joomla. Then I just had an agency—I believe they were in India—it was somewhere that I could outsource to for cheap. I marked them up 100%. I would charge $500 for you to send me a PSD, I would send it to my agency in India, they’d charge me $250 to turn it into a theme. I would send it back and make $500. It wasn’t a productized subscription service, but it was these one-off themes.
As custom stuff happened, we would increase the price. If you needed something more responsive back in 2009, it was obviously more money. Yeah, I have. It was fine. It was a little, quite a bit of hassle. I had that along with a bunch of software products and ecommerce and stuff. I’m trying to think if there are any takeaways I have from that. Productized services are a great way to get started quick these days, especially subscription services. You look at Audience Ops from Brian Casel, or you look at Podcast Motor from Craig Hewitt and there are other examples.
They get up to whatever $20,000, $30,000, $40,000 a month in no time. And then yes, you have to have a process in place, you have to have people to manage. It’s not a software product, but you learn a lot. It’s probably 70%, 80% the same as building a SaaS. Then Craig Hewitt levered it up to then acquire WordPress plugin to then build Castos and now, everything’s combined into one. It’s like a match made in heaven and it’s like a chef’s kiss to the stair-step approach in a way is building these businesses and building on top of each other.
And now one more question from Christoph Engelhardt, “How do you prepare financially or otherwise, for your retirement?” It’s a good question. I like personal finance. I’m a bit of a nerd with this stuff. Before I had sold Drip, I was contributing to retirement for most years—for both Sherry and I—putting them in the US. There are IRAs or 401(k)s.
I did stop. I will admit at the worst times of Drip, when it was growing fast and we had cash crunches, I stopped contributing to retirement. My bet was that Drip would make enough money in the end, whether through an acquisition or whether through throwing off cash, that it would make up for that. The bet worked out for me. It’s not going to work out for everyone. But by the time we sold Drip, I believed between Sherry and my retirement accounts, we had about $300,000, which I was in my late thirties. Is that right? I might’ve been in my early forties. I would prefer to have more by then, but when I looked at compounding and how it was growing, we would have had I’d say a couple million when we retired. But I also counted on having a lot more earnings and being able to put money in.
For me, it’s about saving early. I started contributing right out of college. In fact, if you can do anything for your kids, or nephews, or whatever—I’ll comment on the US because I know the retirement system here—but if there is a RHYTTAC-shielded retirement account, an individual retirement account called an IRA here, as soon as your kids get any income, match what they make, give and put the money. You can put up to $5500 as of this taping into a retirement account.
If you can put it in when they’re 15 or 16, compound interest is the eighth wonder of the world. I believe Albert Einstein said that. The earlier you get, if you invest at 15 versus 30, you get two more doublings of that, if you invest in the stock market. Put it all in high-risk stuff. I would be 100% in stocks. If you’re making 8% per year, then it’s going to double every 9 years. If you make 9% per year, it’s going double every 8 years. From 15% to 30%, you get almost two doubles of that. If you put in $5000, it becomes $10,000, then $20,000 by the time they’re 30. If they don’t contribute until 30, they have to contribute $20,000 to have the same impact that you do when they’re that young.
I started putting money in when I was 22, and just a little bit. I didn’t have much money. I wasn’t making much. I make $15, $17 out of college per hour. But I started putting $50, $100 a month away as early as I possibly could.
Thanks so much for joining me today. That is going to wrap us up. Thanks for hanging out with me a little longer. Last joke, can you imagine if one day MicroConf acquired Microsoft? Ooh, that was a misspoke. Can you imagine if one day Microsoft acquired WIWORK and named it Microsoft Office?
We do have some special podcasting stuff coming up soon. We’re going to have some voting and some nominations. I’m teasing that, so keep your eye out at microconf.com and thank you as always to Hey and Stripe for supporting MicroConf Headlines partners for the year. We love working with them. Thanks for joining me. I’ll see you next week.
Episode 522 | Revisiting Castos, One Year Later
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Rob welcomes back to the show a frequent guest, Craig Hewitt for a “Where Are They Now?” syle episode. Craig is the founder of Castos and has appeared many times on Startups For the Rest of Us. In this episode, they reconnect and talk about the latest with Castos, from hiring a growth marketer, merging brands, private podcasting, and so much more.
The topics we cover
[3:54] Reflections on hiring a growth marketer 1 year later
[6:92] How did the free trial without asking for a credit card experiment work out?
[8:92] Merging brands and moving into enterprise offers
[19:91] Private podcasting
[23:44] What’s new and exciting at Castos
Links from the show
- Episode 466 | Answering Listener Questions With Craig Hewitt
- Episode 493 | A Roundtable Discussion about COVID-19, Working From Home, Payroll Protection and More
- TinySeed Tales – Season 1
- Castos Productions (formerly Podcast Motor)
- Rogue Startups
- The SaaS Podcast Award
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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Rob: Welcome to this week’s episode of Startups for the Rest of Us. I am your host, Rob Walling, here for episode 522. Every week on this show, I cover topics related to building and growing startups using an ambitious yet sustainable, sane approach. I know that you’re not willing to sacrifice your health or your relationships to grow your company, and yet we aspire to build an ambitious startup. Thanks for joining me again this week. I have a many time guest back on the show, Craig Hewitt, who has come on for Q&A episodes. He’s come on for a startup news roundtable. He’s told the story of his startup Castos, which went through TinySeed batch one. You could hear that complete story and detail across the first season of TinySeed Tales where we recorded eight episodes over the course of eight or nine months. You’ll hear this nice longitudinal look at his and his team’s journey as they focused on and grew the company during 2019. I wanted to have him back on today because someone wrote in and said, “I want a ‘where are they now’ episode of Startups for the Rest of Us that looks back and catches up from where Craig left off.” Coincidentally, almost to the day, it was one year since we had recorded the season finale of season one. I hope you enjoy the conversation we have today. Before we dig into that, I want to let you know about the SaaS Podcast Awards that MicroConf is holding right now. You can nominate your favorite podcast that has some affiliation or relationship to SaaS, whether it’s two SaaS founders talking about it or whether it’s people doing interviews. There are four categories of podcasts that we’re going to be looking at and highlighting. If you head to saaspodcastawards.com, you can enter your nominees for each category. In a few weeks, we will have finalists, voting, and eventually, we will present awards to the winners. This is the first of its kind. We’re really excited to be able to gather people together and hear what the people’s choice is for the top podcast and podcasts because it’ll be nice to have finalists to look at across each of these categories. Head over to saaspodcastawards.com to nominate a podcast. With that, let’s dive into my conversation with Craig Hewitt, the founder of Castos. Castos is podcast hosting and production plus private podcasting. It’s actually where this podcast you’re listening to is hosted, as well as TinySeed Tales and the MicroConf podcast. I hope you enjoy our conversation as we look back at the last year and hear where Craig and Castos are now. Craig Hewitt, thanks so much for coming back on the show.
Craig: My pleasure. Thanks for having me, Rob.
Rob: People will know you from Rogue Startups with Dave Rodenbaugh, your podcast, the founder of Castos and PodcastMotor, as well as the subject, the victim of TinySeed Tales season one. We recorded eight episodes back in 2019, got a lot of really good reviews and positive comments about that season just about our conversations, how open you were about sharing your victories, struggles, the journey of being a founder, and growing your company. You’ve also been on Startups for the Rest of Us at least two or three times. You’ve answered questions, I interviewed you about starting Castos and all that stuff. I feel like folks should have a decent idea of who you are and what you’re up to, but for those that don’t, Castos is the startup that you’re focused on. Obviously, you went through batch one of TinySeed. We’re talking offline that before season one of TinySeed Tales, as we started recording it, you were at four full-time employees and now you’re at eight. You tripled in revenue, you’re already in the five figures of monthly revenue when the season started. Over the course of that—I don’t remember how long we recorded, it was about eight or nine months—basically, you tripled on revenue and you haven’t raised any additional funding. You took funding from TinySeed and used that to truly catapult forward. You hired a growth marketer named Denise, who I know has worked out really well. Recently, you hired Matt Medeiros who folks may know from the Matt Report, and he’s your Director of Podcaster Success. A ton has gone on. The last time we spoke to record the final episode of season one of TinySeed Tales was almost one year ago today. It was October 30th of 2019 and as we’re recording today, it’s November 4th. With all of that, welcome to the show. Thanks for coming back on. I’m really excited to dive into what’s been going on over the past year.
Craig: First of all, I can’t believe that we only recorded eight of those episodes. They were intense emotionally—for folks listening to follow that story—because we had a lot of ups and a lot of downs. Hearing that that was only eight episodes makes me feel old and makes me have more gray hair from that, but that was a lot of fun.
Rob: It feels that way to me too. I know 8 aired but it feels like we recorded 16 and I don’t know why that is. I think it’s just tough times.
Craig: It’s just an intense time we’re in, right?
Rob: It was. It was pre-COVID and everything. The death of George Floyd hadn’t happened yet. COVID and this very stressful US presidential election that is happening right now, that wasn’t happening. It really was a lot of business stress on you and a pivotal point in the business.
Craig: Absolutely.
Rob: The way I want to do today is I want to revisit a couple of things that we talked about in the final episode of that season, and then talk about some secret audio. You and I recorded about 10–15 minutes where you were talking about some top-secret future plans you were going to do, but you didn’t want to air that because it’ll give away your strategic move. We’re going to pull some snippets out of that to air because now that it’s been a year; you’ve already done those things. And just talk about some recent developments, basically, with Castos, what worked and what hasn’t. Just do a ‘where are they now.’ I want to kick it off with, during the season of TinySeed Tales, you took a big gamble. We took a couple of big gambles, actually. One, you hired a growth marketer. You went all-in on getting someone to hand off marketing to. That was a challenge for you because you had been the only marketer. You had basically written all the copy and just been in-charge of the strategy and all that. You made a difficult transition during the season of starting to hand this over to her. In the end, it was a resolution of yes, that worked, that was smart, and it was working at that time. A year later, I’m curious to hear your reflections on how that’s been going.
Craig: A year later, it was a fantastic decision. We hired the right person for sure. Denise is wonderful at her job. She is very skilled, very detail-oriented, and is becoming a really strategic thinker from a marketing perspective, which I think is the thing that has changed the most. She would probably be the first one to tell you that she came in without any kind of SaaS marketing experience and now is very savvy in that respect. All the way, up and down the stack or the funnel if you will. We talked about this being the goal. It allows you to move your energy and focus on the business and where you operate. We have a weekly marketing meeting and we chat. Now it’s Denise, Matt, and I because Matt, even though he’s tied as a Director of Podcaster Success, he comes from a sales marketing background. He’s a lot of product and podcasting domain expertise so he’s definitely involved in a lot of the marketing stuff that we do now. I go to that meeting and we talk a lot of really high-level strategy stuff. The two of them go and execute almost all of it now. It’s great because what it does is just put you on a different trajectory than if you do it all yourself. It really is what we wanted. Denise wakes up and thinks about how to grow Castos every day. I do, too, but I think about a whole bunch of other stuff. I think the more that we can let someone focus on doing a single thing—and we’re only eight people so nobody can do just one thing—the more we can get to that, the more successful they are at their jobs. That moves the needle for us, the business.
Rob: That’s good to hear. Of course, we know you update us with what’s going on. I knew that was the story but it has been so fun for me to listen back to the season and hear you put out the job description. You had a process for hiring. There’s always uncertainty, there’s always like, I think this person’s right, will it work? It’s nice when it works out that well. We hired the right person because there can be that paradigm shift or that one plus one equals three or whatever cliche you want to use. It just levels you up so much more than you probably even expect.
Craig: Even more, the other path there could be let’s hire a content marketer just to write, let’s hire an agency to run Facebook ads, let’s hire a copywriter to do this landing page, but I’ll be the glue to hold it all together or the person to coordinate it, and that just still requires a ton of your mental energy. Whereas you can say, hey, Denise, you own this part, this outcome of the business. I am here to support you and the company’s here to support you, but I need you to be the one that thinks about this all the time. It’s just a very different kind of way to work.
Rob: Absolutely. I’ve been struggling to find a name for all three of these but I talked a lot about how in the early days, I had a lot of task-based people. It was usually VAs who could do a specific task. That’s like hiring a copywriter, go do this, you’re really good at this, but now, I’m managing it. So, task-based people, project-based people, and owners. Originally, I was thinking of founders, but really I should say it as task-mindset, project-mindset, owner-mindset. That fits who can really own this whole area—maybe even delegates and projects—but be thinking about where a task-based person might think ahead of the next week, a project-based person thinks ahead for the next month, and as an owner thinking 6–12 months out or maybe even two years. They don’t have to technically own. It’s not about equity and business, but I think it’s about owning the key results, really planning, presenting, and certainly taking input. As an owner, you don’t just do everything yourself. Finding those types of people is hard but it’s what you need to really level up a business, especially at your size. With eight full-time employees, everyone has to be really good or else it’s a huge drag on the company.
Craig: Somewhere that we’re just getting into with maybe that next step of ownership is that the leaders of each group of our organization are involved in hiring. That is super cool to see. We hired a full-stack developer recently. Jonathan, our lead developer, was the final say on who we hire basically. We’re hiring support personnel, and Matt on our team is going to be the final say on who we hire there as that last interview. That’s super cool to see. In respect, it takes some of the burdens off of me because I basically get a couple of people through the process and say, I’m happy with any of them. you go pick. Also, because they feel super empowered to be making that decision, and they know they have to live with it afterward. That’s a really good thing. That’s not a negative thing. We’re just getting into that. We’re just in the second iteration of that step but it’s really cool to see.
Rob: Something else you did during the season was you had a credit card upfront in order to get a 14-day free trial of Castos. During that, this season, you removed it. That just sends all your metrics all over the place. I remember it was a little bit mixed in the end where you said, yeah, it’s better but not enough that it totally makes sense. That was my memory of it. Is that still how you feel about it? You’re still not asking for credit cards. Obviously, it’s a better way to go, you’re getting more leads. Do you feel like that was a huge win? Was it awash? What are your thoughts looking back?
Craig: I think it has been a good thing. It’s tough to tell over. I haven’t gone back and looked at our month-over-month metrics from a strictly growth perspective to say whether in that kind of shorter-term it was a really good thing, but from a user perspective, especially in something like podcasting—Rob, even though you’ve been doing this forever—it’s hard to get started. You might need more than two weeks to really get your show off the ground. What we found is that people come in, they give it a try, we give them a chance to extend their trial even if they want to right at the end. From a compatibility with the user behavior perspective, not asking for a credit card upfront is definitely the way to go. We have no plans of changing it at this point. For users, it’s the right thing to do.
Rob: Something you talked about in the final episode as we wrapped was I said, what’s next and you said, we’re looking at offering a freemium tier, basically a pricing tier that has a max usage-based freemium. I think it was what I referred to it as. From what I know, that never happened. When did you make that decision, and what was the thought there of not introducing that free tier?
Craig: Most of it came down to engineering resources. I hate to say this. If it was just a flip of a switch in Stripe or something, I probably would have tried it but it would’ve required a bit of work on the back-end to get that implemented. We just had other things we wanted to do, features to build, UI to improve, and things like that so I just didn’t feel like it would move the needle in a significant way. Maybe looking back on it now, that’s because the no credit card trial thing didn’t move a needle a ton so I thought that a usage-limited trial might just give the same type of result. Coincidentally, we may be looking at it again but for different reasons.
Rob: It’s always hard to spend a lot of engineering time or a lot of your time making a change like removing a credit card and have it be. Maybe that was worth it. I definitely understand why you’d be hesitant to go freemium knowing that you could get something else built in that time that you’re pretty confident will move the needle, and Freemium is just such an experiment. It’s such an experiment and it’s not a few weeks of work. Even if the engineering time is only 3–4 weeks, you get to the point where, okay now we’ve done it and now we need to watch it for months because freemium doesn’t convert in 30 or 60 days. You have months and months. If you have other things that are working, it can be a tough sell to justify that. The last thing that you talked about in that episode was you were thinking about whether you should move a little more into enterprise-type offerings, that the average revenue per user of a podcast host is not great. It tends to be a commodity thing. If you look at all the podcast hosts, they’re not priced that high. You were noodling on whether or not you wanted to get into that space, start selling to enterprises, and have some offerings that really made sense to be higher priced. After the episode, you and I recorded that little secret audio that we can cut to right now, and had a little bit of conversation about something you were thinking about to raise your average revenue per customer. During the TinySeed retreat at MicroConf Europe in Dubrovnik, we did a hot-seat format. That’s typically how we do it, right? We go around and each founder gets 30 minutes to think through a pretty challenging difficult issue to get feedback from the batch, as well as myself, Tracy, and Einar. Something came out of your hot seat that could potentially change the trajectory of Castos. Do you want to talk a little bit about that?
Craig: Yeah. It’s funny, my talk at my MicroConf Europe was about SaaS metrics. All along, ever since you and I started talking about this business, the metric around Castos that has been the worst, that’s tough to a fact just like our average revenue per user. We’re just not a hundred dollar a month kind of app. I don’t know that we would ever be for the majority of our customers. We started thinking about what people would pay $100 or $200 for. Pretty quickly, the answer came to be audio editing either as a service or a software tool. The value in a software tool is incremental. We’re talking in a previous episode about incremental steps versus big major steps that would double or triple the size of the business. Building software to help people edit their podcast is cool but not that cool—doing it for them is really cool. I happen to have a lot of experience in this from another business in the space. The idea is can we take that other business called PodcastMotor and roll that service level into the Castos platform, or make it super easily accessible to all the Castos customers? It was a really interesting thought exercise. I think that everybody who’s running a business should say, how can you double your business tomorrow, and just come up with crazy ways to do it. At first, this seemed really crazy. About an hour and a half later, I was like, yeah, that’s totally the way to go because it’s a natural progression for a lot of our customers. They come in and start a podcast. They have some degree of success with it. They want to keep going with it. They say, wow, editing all this audio sucks, and it takes me two or three hours every episode, I would love to pay somebody a little bit of money to do that for me.
Rob: For folks who don’t know what PodcastMotor is or how it works, could you give just a few sentences on how good of a fit it actually is for exactly what you want to do here?
Craig: PodcastMotor is a productized service that I’ve been running for 4½, almost 5 years. All we do is podcast editing, we do show note writing, we have a transcriptionist team. The idea really is a show like this records their episodes, sticks the files in Dropbox, and then we do all the work from there. We do audio editing. We do show note writing. Then, we publish to a website media-hosting platform. We could build a fair amount of automation around that part of it, about the publishing part of it, but certainly, it takes all of the onus of the post-production side of the world off of podcaster’s plate, to let them focus on other more important stuff like marketing and growing their business.
Rob: You have this unique experience that likely no other podcast host has. This is where you started with this productized consulting. One of the things during the hot seat is, as we were talking about it, I said, you could just make it your highest tier. You have a $19 plan, a $39 plan, and then just have a $1000 plan—I had just thrown out that number, made the numbers up—and that one includes full-service production, editing, and such. We were mulling that over and it was like, wow, this has been really interesting. One thing I said was, yeah, but the problem then is if you get a bunch of new customers, you have to scale. Now you have to hire editors and you have to hire transcriptionists. You looked me in the eye and you said that’s not that hard. To me that is hard, but to you, it’s not. You’ve been doing it now for years, and you have an amazing process to accomplish that.
Craig: The place this really makes sense is in the scalability of it. Because we have been running this business for a while, we know how to hire and vet people, bring them into our process, onboard customers, and things like that. At the scale, we would hopefully be talking about within Castos or expose to the whole Castos user base, new trial customers, and things like that. They would need to be a little better because we have 50 customers on the PodcastMotor side of things now. We could probably have 500 as part of this combined business. It’s nothing if one of our competitors decided today that they wanted to start a PodcastMotor-type of business tomorrow. They would have the years of headaches that I’ve had so far before they could get to where we are.
Rob: It’s a fascinating competitive advantage. I’m surprised that none of us thought about this sooner. I’m including myself in there, you, Einar, and just anyone in the batch that we never thought about enough to think about combining these. Why do you think that is?
Craig: A little backstory, I guess. The first version of our hosting platform was still under the Seriously Simple Podcasting brand. It was on the seriouslysimplepodcasting.com site and all this kind of stuff. We went through a rebranding exercise to become Castos. Part of that rebranding consideration was, why don’t we just call it PodcastMotor? For a lot of reasons—this is one of the decisions we have to make now—it gets difficult to discern between the editing service and the hosting platform if they’re all under the same roof. We’re going to move forward with this integration to bring the two companies together, but they might still have separate websites. They might just be an integration partner that ultimately all the money still goes in the same bank account. That’s the reason we didn’t put the hosting platform under the podcastmotor.com brand before. We had some concerns about what do people who know PodcastMotor as an editing service come in and see this hosting stuff, what are they going to think? I had definitely thought about combining the brands before, and then made a decision to treat them as separate entities. One because of branding, messaging, and things like that. The other is, like Thomas Smail says, one day you’re going to sell your business, or you’re going to end your business. I wanted to have some optionality and keep them separate so that I could do different things with each of the businesses. I didn’t then think that the combined entity together of both facets of the business was as strong together as it is. That’s probably the thing that I got most out of our discussion, with talking with you, Tracy, Einar, and everyone else. The valuation of this combined company is still really, really strong, whereas the valuation of just a service business maybe isn’t as strong. And the value proposition of, hey, you can come in and we can provide now, the two big huge things that a lot of podcasters need. We’re going to check three of the four or five big boxes in podcasting all in one house.
Rob: You were basically talking about merging PodcastMotor into Castos. Or at least, you were talking about offering editing through Castos because there’s a higher price point, higher average revenue per customer. You talked a lot about not merging the brands potentially, and not merging the websites. It seemed like you were uneasy about that. Talk to me about what’s happened over the last year with PodcastMotor and Castos.
Craig: In the spring of 2020, maybe in the fall of last year, we introduced Castos Productions which was, at that time, a white label version of the PodcastMotor service from within the Castos dashboard. You upload your raw recording files or you send us your Squadcast links like we would do for this episode, then the PodcastMotor team on the backend does the editing, show notes, writing, and production work. That went over well. We had a good reception from clients and from our advisors. People just kick in the tires and say, yup, it makes all the sense in the world to put that all in the same place. I’m happy to do that. So July of this year, we formally merged the companies and started the process of migrating those existing PodcastMotor customers over to using the Castos Productions workflow, to manage all of their podcast stuff in the Castos app, both the production work, hosting, distribution, and analytics all in one place. Then, we took the really big leap which was to merge the brands—naming and the websites—just maybe six weeks ago. If you go to podcastmotor.com today, you’ll go to the Castos productions page on castos.com. Overall, it’s been really successful. Rob, you and I talked offline about the decision to do this. For a lot of reasons, managing just one brand generally is a lot easier from an SEO perspective. It definitely is better to have all of your links juice pointing to one place. There will be people that say, yeah but if you were two brands you could have multiple listings on the first page of Google for a term. That’s the case, but generally, we think we can rank for more terms as a single site, so that’s what we’ve done. Generally, the only thing that we knew we would have to do and I think we’ve done a good job is to manage that legacy PodcastMotor name for people that know us or were customers of ours before and want to come back to do another season or something. On that page, on that Castos Productions page, we reference PodcastMotor. We have a banner at the top of the page announcing that PodcastMotor is now Castos Productions and links to an internal blog post that we have about it. I think that’s the thing that I was the most scared of is what is like a really nice brand? The PodcastMotor brand and the job we do there was really great, so how to transfer as much of that over to Castos Productions as possible? The thing that you and I talked a lot about was the thing that gave me pause before and that we’re keeping a very close eye on now that that move is taking place.
Rob: This is one of those decisions that I think is the right decision the way you did it. Correct me if I’m wrong, but I believe I gently nudged you in that direction of my gut based on things I’ve seen, and where you are is that you should fully merge. There’s more power in it, there are more SEO powers, and there’s more brand power and all that. I’m not like it’s 100%. You absolutely have to do this. It’s the only way to do it. I do think there are nuances as you said, but I feel like it is the right decision and has been the right decision from my outsider’s perspective. You’re six weeks post doing it, so obviously you only have so much perspective at this point. Do you feel so far that it was the right choice? Do you have any regrets about merging those two brands?
Craig: It’s definitely been the right choice. I don’t have any regrets. I think the reason is if you look at the potential plus and minus of it, the plus is that everything is in one place. It’s one brand. Messaging should all be really clear around this. The downside is that last part maybe, with two separate brands, you can be more clear and opinionated about what that messaging is. When they’re all in one place, it can get a little more muddled and a little more difficult to be really explicit about what a brand is. Now, Castos is podcast hosting and production, whereas before it was just one thing. I think the positive of having it all in one place. Having these professional services in front of all of our customers is just way above that potential difficulty and messaging.
Rob: Right and it’s such a differentiator because no one else is doing this. Where else can you go to get hosting, to get editing and production, all the transcripts, the YouTube stuff, and just all the things you do? It is a unique space in the market. I’m excited to see where that takes you moving forward. How hard did it wind up being? It’s funny we talked about a year ago and you said you got done with it six weeks ago, surely you weren’t working on it for ten-and-a-half months. It must’ve been starts and stops.
Craig: It was a lot of starts and stops. I probably just forgot about it or it wasn’t a huge priority for a while. I think we really saw some good traction with Castos Productions when it was just a white label version of PodcastMotor. We really thought, time to get more serious about it because at that point we really had three brands. That was too much. I decided to bring it all together. It’s a fair gamble because we talked about reversible decisions. I don’t think that’s a reversible decision. We’re down this path. That’s a 301 redirect like that stuff to take back. We tested the waters with it too. I felt like we had some data well before we did all the stuff in July.
Rob: That’s the thing. I have a question here. Has it moved the needle yet? I’m not totally sure what I mean by that, but I guess I’m thinking you bring over this brand and this new service, and you would hope that new customers or existing customers would adopt it in a way that maybe they wouldn’t have if you kept those two apps separate.
Craig: It’s definitely moved the needle. First, all of our revenue code goes into one place, that’s great. That’s just easier to keep track of and everything. The thing that it does is that it simplifies our messaging a lot because instead of me being on sales calls for Castos Productions and for PodcastMotor, I’m on one side of sales calls. We have one set of pricing, we have one set of offerings, and in that respect, it’s definitely improved our positioning. But it’s still an ongoing thing. It’s still something that we are continuing to refine the experience, the actual user experience, positioning, the pricing, and all of this, which is cool. It’s another lever we can turn and that’s fun to have.
Rob: Yeah. What I love about it is this concept of a dual funnel that I keep bringing up of having this wide, lower-cost funnel. We have a lot of people coming in. Maybe it’s freemium, maybe it’s a credit card or whatever but when you’re getting hundreds of trial sign-ups or even into the low four figures of trial sign-ups in a month, that’s a very wide low touch, low-cost funnel usually with low average revenue per customer. You can build a good business on that. You want to raise average revenue over time. That’s a low touch funnel. Then, there are high touch funnels where you’re selling for $500 or $1000 or $5000 a month and more enterprise stuff, long sales cycles. You can build a business out of there. The dual funnel, when you have a SaaS that has both of those, that’s amazing. Those are the apps that I’m seeing grow the fastest right now. I think back to even in the Drip days of our starting price of $49 and eventually, we had a $1 plan and then a free plan. We had people coming in and saying I’m going to pay $1000 a month or $1500 or $2000 a month. That’s a nice dual funnel. You do have this amazing brand, you have the reach, and your word of mouth because you can have thousands or tens of thousands of paying customers on the low end. Even if you only have 50 or 100 or 200 larger customers, it can become the point where the vast majority of revenue actually comes from those because they pay you such an overwhelming amount of money. A lot more apps out there are like this than people realize. A lot of the apps we use that are inexpensive actually make a ton of money. Slack’s another good example or Zoom where they have this free plan. They have a wide funnel. Everybody knows who they are and if you’re a small company, you pay Slack $6 or $8 a month per employee. My team is a team of five. I’m paying them $30. That’s not a great average revenue per customer for a company that wants a multibillion evaluation. But IBM, Microsoft, or whoever—I guess Microsoft has their own product—insert Fortune 500 company here who doesn’t have a competing product, are likely paying Slack $10,000, $20,000, $30,000 a month. That is the dual funnel that allows them to grow incredibly fast. That’s what you’ve introduced here. You essentially still have this great product with this great low-end price point. Great for consumers, not for your average revenue per customer but great for your customers, and you do have a mini brand with thousands of people that use it. Now, you also have this high-end enterprise offering and that brings that average revenue per customer up pretty substantially.
Craig: Yeah. We’re now getting into the third leg of that stool which is really cool. It has its own messaging challenges but we are having conventional podcasting, podcast editing as a service, and then private podcasting that is in some ways a whole other animal, a whole other product and whole other type of customer but is very interesting both from a revenue perspective and from a business and product and where we are on the market perspective. It’s cool and challenging at the same time.
Rob: I’m really interested to dig into this because when you talked about building private podcasting, the first thing I asked was is anybody else doing this? Why would you do it? I’m not sure I understand it but you guys are essentially on the leading edge of this. You’re stepping out. This is a novel, new entry into the market. That’s the thing. I was thinking, I’m sure it’s aimed at (I can imagine) any Fortune 5000 company might want a private podcast for their sales staff or for their employees in this day and age of working remote, but I could also see Startups For the Rest of Us having a private podcast that people pay a Patreon or a subscription for. I can see MicroConf having a private podcast for people who go to this event or for the Connect Slack Channel with only them. Or how about a TinySeed private podcast only for investors or only for mentors? Am I making this up or is that where it’s headed?
Craig: It’s literally anything you can imagine. We have mental health professionals having private podcasts for each of their patients. We have Fortune 100 companies that we’re working with having internal private podcasts for their sales team or for their HR groups. We also have enormous health and fitness brands having private podcasts as an extension of their membership site or their course. That’s tens of thousands of people coming in. They have a course or they have a membership site. They have content there and they want to add podcasting as another way to connect with their tribe or their members. We are really uniquely positioned. One, from our WordPress integration, that a lot of people do this membership type stuff in WordPress, so we’re a natural fit there. We also have some native integration with membership platforms like MemberSpace to where new members start paying you for access to membership sites. That person automatically gets added to a private podcast in Castos. All totally automatic that you as membership site administrator don’t have to do anything and you’re able to offer this to your members, which is a huge value. I think it’s just such a natural fit. Now that we’re here I think of course, why didn’t we do this a few years ago? Rob, it might be like what you saw with Drip where you weren’t ready, the market maybe wasn’t ready. Now—knock on wood—I feel like we’re at the right place at the right time with this because it’s a huge opportunity and people come to us and they are absolutely thrilled that we do this the way we do. That makes me feel really good.
Rob: It’s easy to think like a product person. The next feature I launch is going to be the one that changes it. Most times it’s not, most times you try to market it and it’s ho-hum. But this one seems to have really resonated in a way that I’m not sure I anticipated when you were talking about it. I’d hope that it would bring in the Fortune 1000 or 5000. You can charge a lot more for this because it is a premium feature, but the conversation you’re having with people on the interest of this, it sounds like has been really strong. Did you expect that or were you a little bit questioning or tentative about it? I know you were all in on building the future but did you expect it to have this level of interest?
Craig: I would be lying if I said of course I knew that this was going to happen. Of course, I was very hopeful, but I think you don’t know when you’re expanding the edge of what people expect from an ecosystem and a platform, and the behavior that they have with something like podcasting or email marketing. It is when you say you can charge money for a podcast directly or you can only offer this podcast to certain people. Even today, folks are saying that’s not a thing and you explain it to them. They go, of course, that totally makes sense. I can imagine doing this for X. When we started to have some of those initial discussions, then we had more confidence in it. We did a fair bit of collecting email addresses and chatting with folks. We had some people on the platform from day one that was duct-taping this together with Zapier and the membership platform and stuff like that but didn’t have that last piece of individualized private RSS feeds from the hosting provider. That’s what we are providing.
Rob: Right, so you can revoke access in essence when it happens. Congrats on getting that life and certainly stoked to hear about the interest. Obviously, as an investor through TinySeed, it’s nice to see when things go right and I get to live vicariously through your victories, which is fun to be along for the ride. I do want to congratulate you as we move to wrapping up. I want to congratulate you on hiring Matt Medeiros as your Director of Podcaster Success. If folks have not listened to the Audience Podcast and if you are interested in starting your own podcast, or growing your audience, or learning how to monetize, or all the tech stuff around podcasting, search for Audience in your podcatcher. I listen to every episode that comes out. It’s a really high-quality show. I can tell that Matt has pulled a burden off of you because I know that you were putting that out every week and I know it was a ton of work for you.
Craig: Yeah. It’s funny. Just before recording this, Matt and I recorded an episode and talked a lot about this, him coming on board, he is a better podcaster than I am and has been doing it for longer and it’s been awesome to bring in a total A player to own that part of the business. As an entity of the podcast, it’s much better off primarily in his hands. It’s been cool.
Rob: That’s a double win when they can do it perhaps a little bit better than you can and that you get the time back. You don’t have the mental burden of, what am I doing because producing content like this is fun, but it does take that good glucose. It takes that creative energy that you can’t put into writing copy or doing other harder things. As we wrap up, I want to hear what you’re excited about right now. What’s new with Castos? Whatever this week or this month? What’s kind of the big thing that gets you excited?
Craig: We have like two real initiatives that were driving hard on. One is doing everything we can to be the obvious choice for people who want to create a podcast and use WordPress as their website. Specifically what that means is we’re launching an integration with Elementor by the time this goes live. This will be out so you can manage all of your podcasts, design, contents, player, everything from the Elementor editor. Elementor is the most popular page builder for WordPress, so we’ll fit directly into the Elementor editor and all of your podcast stuff happens right from Elementor. That is super cool and hopefully opens up a chance to do some co-marketing and brand exposure between organizations. We’re doing more things in that kind of vein of the businesses, just doing cool things and offering good free tools for people on WordPress to make that experience even better. The other one is private podcasting. It takes a lot of different forms. I talked about courses and membership sites but also for internal company podcasts and working with real enterprises and what that looks like. The question mark still—we might have talked about this last year—is Castos directly being able to be the payment processor via Stripe, a way for you to charge money for your podcast directly. That’s still a bit of a question mark. I think it’s a question mark from a strategic perspective because I think about podcasting as a hobbyist and an aspirational thing, I can imagine a lot of people coming into a tool like this, like Substack. I imagine Substack has an enormous number of people that don’t make any money from their newsletter. If you think that what we’re talking about building with premium podcasting is the same kind of thing, you’re going to have a bunch of people coming in, making content, charging money for it, and not making any money. That’s just how it goes. It’s tough to build a community and a following online. It’s even harder to get those people to pay you money having the micropreneur academy, FounderCafe. We’ve taken the approach so far of let’s help people that already have a significant following, and integrating with their course platform, their membership site, or their community, and offering podcasting as something that they add-on at an additional way to that. From a project strategy perspective, I don’t know if going directly to people that want to charge money is the way to go. I’m sure we’ll do it but I think we’ve made the right decision so far to say let’s use the audience we already have and the membership tools that they’re already using to manage those members and payments and things like that and us be the podcasting tool that adds on to those, as opposed to having to—from a product perspective—create the whole stack and maybe have people come in that, think they can build a community, and charge people money for it because I think it’s just really, really hard. We’ll see.
Rob: The aspirational people will come but I think you can get around that with pricing. I’m just going to throw up pricing. If it’s $99 a month plus whatever for downloads or something then you’re not going to get as many aspirational because they’re going to say that’s too expensive. If I had MicroConf as an example or Startups for the Rest of Us, $99 a month is a no brainer for us. Certainly for whoever, Target, General Mills, and Best Buy, these are just Fortune 500 companies that are here in Minneapolis that I was thinking of. For them, it should be even higher. I guess Best Buy, Target, and General Mills are not going to charge their people. That would only be for someone more like Startups for the Rest of Us or MicroConf if we did decide to make that a paid thing. Again, if you just keep that minimum price at a certain point, because you’re not a commodity right now. You’re such a unique offering that if people want it, they need to come to Castos. Once the feature is going to get cloned, you get copy cats, they probably won’t build it as well as you guys have. Eventually, it will get to that point and you have to make that decision of, do we want that lower-end of the market, the aspirational people, but I guess you can make that decision when you get there. Is it something you feel like you could solve with pricing by just having that higher minimum per month?
Craig: I think so, but I think that all that does is it doesn’t attract the aspirational folks that don’t already have that audience or don’t think they could get that audience. The thing that I’m most concerned about is this resource allocation of it’s a month’s worth of work for a developer at least to build all this stuff, could we go do something better with that?
Rob: I want to see it that you have ample leads coming in on that higher-end that want to charge for it. If you’ve only had a handful come in then I don’t know. If you haven’t lost a deal because you don’t have it built-in and it’s a month of work, that’s tough. Given how fast you have to move and how much you’re building, it’s a tough decision to make.
Craig: That’s definitely a question mark. It would be super interesting but I’m not sure.
Rob: Well, awesome man. Thanks again for taking an hour and hanging out with me here again on Startups for the Rest of Us. On Twitter, you are @TheCraigHewitt and obviously castos.com if folks want to see what you’re up to. Thanks so much for joining me again this week. I hope you enjoyed that conversation with Craig. I’ll definitely have him back again in the future. He always has interesting insights, is moving so fast, and doing so many interesting things that it’s pretty easy to bring out essentially good conversation and good content for here on the show.
Craig: My pleasure. Thanks for having me, Rob.
Rob: People will know you from Rogue Startups with Dave Rodenbaugh, your podcast, the founder of Castos and PodcastMotor, as well as the subject, the victim of TinySeed Tales season one. We recorded eight episodes back in 2019, got a lot of really good reviews and positive comments about that season just about our conversations, how open you were about sharing your victories, struggles, the journey of being a founder, and growing your company. You’ve also been on Startups for the Rest of Us at least two or three times. You’ve answered questions, I interviewed you about starting Castos and all that stuff. I feel like folks should have a decent idea of who you are and what you’re up to, but for those that don’t, Castos is the startup that you’re focused on. Obviously, you went through batch one of TinySeed. We’re talking offline that before season one of TinySeed Tales, as we started recording it, you were at four full-time employees and now you’re at eight. You tripled in revenue, you’re already in the five figures of monthly revenue when the season started. Over the course of that—I don’t remember how long we recorded, it was about eight or nine months—basically, you tripled on revenue and you haven’t raised any additional funding. You took funding from TinySeed and used that to truly catapult forward. You hired a growth marketer named Denise, who I know has worked out really well. Recently, you hired Matt Medeiros who folks may know from the Matt Report, and he’s your Director of Podcaster Success. A ton has gone on. The last time we spoke to record the final episode of season one of TinySeed Tales was almost one year ago today. It was October 30th of 2019 and as we’re recording today, it’s November 4th. With all of that, welcome to the show. Thanks for coming back on. I’m really excited to dive into what’s been going on over the past year.
Craig: First of all, I can’t believe that we only recorded eight of those episodes. They were intense emotionally—for folks listening to follow that story—because we had a lot of ups and a lot of downs. Hearing that that was only eight episodes makes me feel old and makes me have more gray hair from that, but that was a lot of fun.
Rob: It feels that way to me too. I know 8 aired but it feels like we recorded 16 and I don’t know why that is. I think it’s just tough times.
Craig: It’s just an intense time we’re in, right?
Rob: It was. It was pre-COVID and everything. The death of George Floyd hadn’t happened yet. COVID and this very stressful US presidential election that is happening right now, that wasn’t happening. It really was a lot of business stress on you and a pivotal point in the business.
Craig: Absolutely.
Rob: The way I want to do today is I want to revisit a couple of things that we talked about in the final episode of that season, and then talk about some secret audio. You and I recorded about 10–15 minutes where you were talking about some top-secret future plans you were going to do, but you didn’t want to air that because it’ll give away your strategic move. We’re going to pull some snippets out of that to air because now that it’s been a year; you’ve already done those things. And just talk about some recent developments, basically, with Castos, what worked and what hasn’t. Just do a ‘where are they now.’ I want to kick it off with, during the season of TinySeed Tales, you took a big gamble. We took a couple of big gambles, actually. One, you hired a growth marketer. You went all-in on getting someone to hand off marketing to. That was a challenge for you because you had been the only marketer. You had basically written all the copy and just been in-charge of the strategy and all that. You made a difficult transition during the season of starting to hand this over to her. In the end, it was a resolution of yes, that worked, that was smart, and it was working at that time. A year later, I’m curious to hear your reflections on how that’s been going.
Craig: A year later, it was a fantastic decision. We hired the right person for sure. Denise is wonderful at her job. She is very skilled, very detail-oriented, and is becoming a really strategic thinker from a marketing perspective, which I think is the thing that has changed the most. She would probably be the first one to tell you that she came in without any kind of SaaS marketing experience and now is very savvy in that respect. All the way, up and down the stack or the funnel if you will. We talked about this being the goal. It allows you to move your energy and focus on the business and where you operate. We have a weekly marketing meeting and we chat. Now it’s Denise, Matt, and I because Matt, even though he’s tied as a Director of Podcaster Success, he comes from a sales marketing background. He’s a lot of product and podcasting domain expertise so he’s definitely involved in a lot of the marketing stuff that we do now. I go to that meeting and we talk a lot of really high-level strategy stuff. The two of them go and execute almost all of it now. It’s great because what it does is just put you on a different trajectory than if you do it all yourself. It really is what we wanted. Denise wakes up and thinks about how to grow Castos every day. I do, too, but I think about a whole bunch of other stuff. I think the more that we can let someone focus on doing a single thing—and we’re only eight people so nobody can do just one thing—the more we can get to that, the more successful they are at their jobs. That moves the needle for us, the business.
Rob: That’s good to hear. Of course, we know you update us with what’s going on. I knew that was the story but it has been so fun for me to listen back to the season and hear you put out the job description. You had a process for hiring. There’s always uncertainty, there’s always like, I think this person’s right, will it work? It’s nice when it works out that well. We hired the right person because there can be that paradigm shift or that one plus one equals three or whatever cliche you want to use. It just levels you up so much more than you probably even expect.
Craig: Even more, the other path there could be let’s hire a content marketer just to write, let’s hire an agency to run Facebook ads, let’s hire a copywriter to do this landing page, but I’ll be the glue to hold it all together or the person to coordinate it, and that just still requires a ton of your mental energy. Whereas you can say, hey, Denise, you own this part, this outcome of the business. I am here to support you and the company’s here to support you, but I need you to be the one that thinks about this all the time. It’s just a very different kind of way to work.
Rob: Absolutely. I’ve been struggling to find a name for all three of these but I talked a lot about how in the early days, I had a lot of task-based people. It was usually VAs who could do a specific task. That’s like hiring a copywriter, go do this, you’re really good at this, but now, I’m managing it. So, task-based people, project-based people, and owners. Originally, I was thinking of founders, but really I should say it as task-mindset, project-mindset, owner-mindset. That fits who can really own this whole area—maybe even delegates and projects—but be thinking about where a task-based person might think ahead of the next week, a project-based person thinks ahead for the next month, and as an owner thinking 6–12 months out or maybe even two years. They don’t have to technically own. It’s not about equity and business, but I think it’s about owning the key results, really planning, presenting, and certainly taking input. As an owner, you don’t just do everything yourself. Finding those types of people is hard but it’s what you need to really level up a business, especially at your size. With eight full-time employees, everyone has to be really good or else it’s a huge drag on the company.
Craig: Somewhere that we’re just getting into with maybe that next step of ownership is that the leaders of each group of our organization are involved in hiring. That is super cool to see. We hired a full-stack developer recently. Jonathan, our lead developer, was the final say on who we hire basically. We’re hiring support personnel, and Matt on our team is going to be the final say on who we hire there as that last interview. That’s super cool to see. In respect, it takes some of the burdens off of me because I basically get a couple of people through the process and say, I’m happy with any of them. you go pick. Also, because they feel super empowered to be making that decision, and they know they have to live with it afterward. That’s a really good thing. That’s not a negative thing. We’re just getting into that. We’re just in the second iteration of that step but it’s really cool to see.
Rob: Something else you did during the season was you had a credit card upfront in order to get a 14-day free trial of Castos. During that, this season, you removed it. That just sends all your metrics all over the place. I remember it was a little bit mixed in the end where you said, yeah, it’s better but not enough that it totally makes sense. That was my memory of it. Is that still how you feel about it? You’re still not asking for credit cards. Obviously, it’s a better way to go, you’re getting more leads. Do you feel like that was a huge win? Was it awash? What are your thoughts looking back?
Craig: I think it has been a good thing. It’s tough to tell over. I haven’t gone back and looked at our month-over-month metrics from a strictly growth perspective to say whether in that kind of shorter-term it was a really good thing, but from a user perspective, especially in something like podcasting—Rob, even though you’ve been doing this forever—it’s hard to get started. You might need more than two weeks to really get your show off the ground. What we found is that people come in, they give it a try, we give them a chance to extend their trial even if they want to right at the end. From a compatibility with the user behavior perspective, not asking for a credit card upfront is definitely the way to go. We have no plans of changing it at this point. For users, it’s the right thing to do.
Rob: Something you talked about in the final episode as we wrapped was I said, what’s next and you said, we’re looking at offering a freemium tier, basically a pricing tier that has a max usage-based freemium. I think it was what I referred to it as. From what I know, that never happened. When did you make that decision, and what was the thought there of not introducing that free tier?
Craig: Most of it came down to engineering resources. I hate to say this. If it was just a flip of a switch in Stripe or something, I probably would have tried it but it would’ve required a bit of work on the back-end to get that implemented. We just had other things we wanted to do, features to build, UI to improve, and things like that so I just didn’t feel like it would move the needle in a significant way. Maybe looking back on it now, that’s because the no credit card trial thing didn’t move a needle a ton so I thought that a usage-limited trial might just give the same type of result. Coincidentally, we may be looking at it again but for different reasons.
Rob: It’s always hard to spend a lot of engineering time or a lot of your time making a change like removing a credit card and have it be. Maybe that was worth it. I definitely understand why you’d be hesitant to go freemium knowing that you could get something else built in that time that you’re pretty confident will move the needle, and Freemium is just such an experiment. It’s such an experiment and it’s not a few weeks of work. Even if the engineering time is only 3–4 weeks, you get to the point where, okay now we’ve done it and now we need to watch it for months because freemium doesn’t convert in 30 or 60 days. You have months and months. If you have other things that are working, it can be a tough sell to justify that. The last thing that you talked about in that episode was you were thinking about whether you should move a little more into enterprise-type offerings, that the average revenue per user of a podcast host is not great. It tends to be a commodity thing. If you look at all the podcast hosts, they’re not priced that high. You were noodling on whether or not you wanted to get into that space, start selling to enterprises, and have some offerings that really made sense to be higher priced. After the episode, you and I recorded that little secret audio that we can cut to right now, and had a little bit of conversation about something you were thinking about to raise your average revenue per customer. During the TinySeed retreat at MicroConf Europe in Dubrovnik, we did a hot-seat format. That’s typically how we do it, right? We go around and each founder gets 30 minutes to think through a pretty challenging difficult issue to get feedback from the batch, as well as myself, Tracy, and Einar. Something came out of your hot seat that could potentially change the trajectory of Castos. Do you want to talk a little bit about that?
Craig: Yeah. It’s funny, my talk at my MicroConf Europe was about SaaS metrics. All along, ever since you and I started talking about this business, the metric around Castos that has been the worst, that’s tough to a fact just like our average revenue per user. We’re just not a hundred dollar a month kind of app. I don’t know that we would ever be for the majority of our customers. We started thinking about what people would pay $100 or $200 for. Pretty quickly, the answer came to be audio editing either as a service or a software tool. The value in a software tool is incremental. We’re talking in a previous episode about incremental steps versus big major steps that would double or triple the size of the business. Building software to help people edit their podcast is cool but not that cool—doing it for them is really cool. I happen to have a lot of experience in this from another business in the space. The idea is can we take that other business called PodcastMotor and roll that service level into the Castos platform, or make it super easily accessible to all the Castos customers? It was a really interesting thought exercise. I think that everybody who’s running a business should say, how can you double your business tomorrow, and just come up with crazy ways to do it. At first, this seemed really crazy. About an hour and a half later, I was like, yeah, that’s totally the way to go because it’s a natural progression for a lot of our customers. They come in and start a podcast. They have some degree of success with it. They want to keep going with it. They say, wow, editing all this audio sucks, and it takes me two or three hours every episode, I would love to pay somebody a little bit of money to do that for me.
Rob: For folks who don’t know what PodcastMotor is or how it works, could you give just a few sentences on how good of a fit it actually is for exactly what you want to do here?
Craig: PodcastMotor is a productized service that I’ve been running for 4½, almost 5 years. All we do is podcast editing, we do show note writing, we have a transcriptionist team. The idea really is a show like this records their episodes, sticks the files in Dropbox, and then we do all the work from there. We do audio editing. We do show note writing. Then, we publish to a website media-hosting platform. We could build a fair amount of automation around that part of it, about the publishing part of it, but certainly, it takes all of the onus of the post-production side of the world off of podcaster’s plate, to let them focus on other more important stuff like marketing and growing their business.
Rob: You have this unique experience that likely no other podcast host has. This is where you started with this productized consulting. One of the things during the hot seat is, as we were talking about it, I said, you could just make it your highest tier. You have a $19 plan, a $39 plan, and then just have a $1000 plan—I had just thrown out that number, made the numbers up—and that one includes full-service production, editing, and such. We were mulling that over and it was like, wow, this has been really interesting. One thing I said was, yeah, but the problem then is if you get a bunch of new customers, you have to scale. Now you have to hire editors and you have to hire transcriptionists. You looked me in the eye and you said that’s not that hard. To me that is hard, but to you, it’s not. You’ve been doing it now for years, and you have an amazing process to accomplish that.
Craig: The place this really makes sense is in the scalability of it. Because we have been running this business for a while, we know how to hire and vet people, bring them into our process, onboard customers, and things like that. At the scale, we would hopefully be talking about within Castos or expose to the whole Castos user base, new trial customers, and things like that. They would need to be a little better because we have 50 customers on the PodcastMotor side of things now. We could probably have 500 as part of this combined business. It’s nothing if one of our competitors decided today that they wanted to start a PodcastMotor-type of business tomorrow. They would have the years of headaches that I’ve had so far before they could get to where we are.
Rob: It’s a fascinating competitive advantage. I’m surprised that none of us thought about this sooner. I’m including myself in there, you, Einar, and just anyone in the batch that we never thought about enough to think about combining these. Why do you think that is?
Craig: A little backstory, I guess. The first version of our hosting platform was still under the Seriously Simple Podcasting brand. It was on the seriouslysimplepodcasting.com site and all this kind of stuff. We went through a rebranding exercise to become Castos. Part of that rebranding consideration was, why don’t we just call it PodcastMotor? For a lot of reasons—this is one of the decisions we have to make now—it gets difficult to discern between the editing service and the hosting platform if they’re all under the same roof. We’re going to move forward with this integration to bring the two companies together, but they might still have separate websites. They might just be an integration partner that ultimately all the money still goes in the same bank account. That’s the reason we didn’t put the hosting platform under the podcastmotor.com brand before. We had some concerns about what do people who know PodcastMotor as an editing service come in and see this hosting stuff, what are they going to think? I had definitely thought about combining the brands before, and then made a decision to treat them as separate entities. One because of branding, messaging, and things like that. The other is, like Thomas Smail says, one day you’re going to sell your business, or you’re going to end your business. I wanted to have some optionality and keep them separate so that I could do different things with each of the businesses. I didn’t then think that the combined entity together of both facets of the business was as strong together as it is. That’s probably the thing that I got most out of our discussion, with talking with you, Tracy, Einar, and everyone else. The valuation of this combined company is still really, really strong, whereas the valuation of just a service business maybe isn’t as strong. And the value proposition of, hey, you can come in and we can provide now, the two big huge things that a lot of podcasters need. We’re going to check three of the four or five big boxes in podcasting all in one house.
Rob: You were basically talking about merging PodcastMotor into Castos. Or at least, you were talking about offering editing through Castos because there’s a higher price point, higher average revenue per customer. You talked a lot about not merging the brands potentially, and not merging the websites. It seemed like you were uneasy about that. Talk to me about what’s happened over the last year with PodcastMotor and Castos.
Craig: In the spring of 2020, maybe in the fall of last year, we introduced Castos Productions which was, at that time, a white label version of the PodcastMotor service from within the Castos dashboard. You upload your raw recording files or you send us your Squadcast links like we would do for this episode, then the PodcastMotor team on the backend does the editing, show notes, writing, and production work. That went over well. We had a good reception from clients and from our advisors. People just kick in the tires and say, yup, it makes all the sense in the world to put that all in the same place. I’m happy to do that. So July of this year, we formally merged the companies and started the process of migrating those existing PodcastMotor customers over to using the Castos Productions workflow, to manage all of their podcast stuff in the Castos app, both the production work, hosting, distribution, and analytics all in one place. Then, we took the really big leap which was to merge the brands—naming and the websites—just maybe six weeks ago. If you go to podcastmotor.com today, you’ll go to the Castos productions page on castos.com. Overall, it’s been really successful. Rob, you and I talked offline about the decision to do this. For a lot of reasons, managing just one brand generally is a lot easier from an SEO perspective. It definitely is better to have all of your links juice pointing to one place. There will be people that say, yeah but if you were two brands you could have multiple listings on the first page of Google for a term. That’s the case, but generally, we think we can rank for more terms as a single site, so that’s what we’ve done. Generally, the only thing that we knew we would have to do and I think we’ve done a good job is to manage that legacy PodcastMotor name for people that know us or were customers of ours before and want to come back to do another season or something. On that page, on that Castos Productions page, we reference PodcastMotor. We have a banner at the top of the page announcing that PodcastMotor is now Castos Productions and links to an internal blog post that we have about it. I think that’s the thing that I was the most scared of is what is like a really nice brand? The PodcastMotor brand and the job we do there was really great, so how to transfer as much of that over to Castos Productions as possible? The thing that you and I talked a lot about was the thing that gave me pause before and that we’re keeping a very close eye on now that that move is taking place.
Rob: This is one of those decisions that I think is the right decision the way you did it. Correct me if I’m wrong, but I believe I gently nudged you in that direction of my gut based on things I’ve seen, and where you are is that you should fully merge. There’s more power in it, there are more SEO powers, and there’s more brand power and all that. I’m not like it’s 100%. You absolutely have to do this. It’s the only way to do it. I do think there are nuances as you said, but I feel like it is the right decision and has been the right decision from my outsider’s perspective. You’re six weeks post doing it, so obviously you only have so much perspective at this point. Do you feel so far that it was the right choice? Do you have any regrets about merging those two brands?
Craig: It’s definitely been the right choice. I don’t have any regrets. I think the reason is if you look at the potential plus and minus of it, the plus is that everything is in one place. It’s one brand. Messaging should all be really clear around this. The downside is that last part maybe, with two separate brands, you can be more clear and opinionated about what that messaging is. When they’re all in one place, it can get a little more muddled and a little more difficult to be really explicit about what a brand is. Now, Castos is podcast hosting and production, whereas before it was just one thing. I think the positive of having it all in one place. Having these professional services in front of all of our customers is just way above that potential difficulty and messaging.
Rob: Right and it’s such a differentiator because no one else is doing this. Where else can you go to get hosting, to get editing and production, all the transcripts, the YouTube stuff, and just all the things you do? It is a unique space in the market. I’m excited to see where that takes you moving forward. How hard did it wind up being? It’s funny we talked about a year ago and you said you got done with it six weeks ago, surely you weren’t working on it for ten-and-a-half months. It must’ve been starts and stops.
Craig: It was a lot of starts and stops. I probably just forgot about it or it wasn’t a huge priority for a while. I think we really saw some good traction with Castos Productions when it was just a white label version of PodcastMotor. We really thought, time to get more serious about it because at that point we really had three brands. That was too much. I decided to bring it all together. It’s a fair gamble because we talked about reversible decisions. I don’t think that’s a reversible decision. We’re down this path. That’s a 301 redirect like that stuff to take back. We tested the waters with it too. I felt like we had some data well before we did all the stuff in July.
Rob: That’s the thing. I have a question here. Has it moved the needle yet? I’m not totally sure what I mean by that, but I guess I’m thinking you bring over this brand and this new service, and you would hope that new customers or existing customers would adopt it in a way that maybe they wouldn’t have if you kept those two apps separate.
Craig: It’s definitely moved the needle. First, all of our revenue code goes into one place, that’s great. That’s just easier to keep track of and everything. The thing that it does is that it simplifies our messaging a lot because instead of me being on sales calls for Castos Productions and for PodcastMotor, I’m on one side of sales calls. We have one set of pricing, we have one set of offerings, and in that respect, it’s definitely improved our positioning. But it’s still an ongoing thing. It’s still something that we are continuing to refine the experience, the actual user experience, positioning, the pricing, and all of this, which is cool. It’s another lever we can turn and that’s fun to have.
Rob: Yeah. What I love about it is this concept of a dual funnel that I keep bringing up of having this wide, lower-cost funnel. We have a lot of people coming in. Maybe it’s freemium, maybe it’s a credit card or whatever but when you’re getting hundreds of trial sign-ups or even into the low four figures of trial sign-ups in a month, that’s a very wide low touch, low-cost funnel usually with low average revenue per customer. You can build a good business on that. You want to raise average revenue over time. That’s a low touch funnel. Then, there are high touch funnels where you’re selling for $500 or $1000 or $5000 a month and more enterprise stuff, long sales cycles. You can build a business out of there. The dual funnel, when you have a SaaS that has both of those, that’s amazing. Those are the apps that I’m seeing grow the fastest right now. I think back to even in the Drip days of our starting price of $49 and eventually, we had a $1 plan and then a free plan. We had people coming in and saying I’m going to pay $1000 a month or $1500 or $2000 a month. That’s a nice dual funnel. You do have this amazing brand, you have the reach, and your word of mouth because you can have thousands or tens of thousands of paying customers on the low end. Even if you only have 50 or 100 or 200 larger customers, it can become the point where the vast majority of revenue actually comes from those because they pay you such an overwhelming amount of money. A lot more apps out there are like this than people realize. A lot of the apps we use that are inexpensive actually make a ton of money. Slack’s another good example or Zoom where they have this free plan. They have a wide funnel. Everybody knows who they are and if you’re a small company, you pay Slack $6 or $8 a month per employee. My team is a team of five. I’m paying them $30. That’s not a great average revenue per customer for a company that wants a multibillion evaluation. But IBM, Microsoft, or whoever—I guess Microsoft has their own product—insert Fortune 500 company here who doesn’t have a competing product, are likely paying Slack $10,000, $20,000, $30,000 a month. That is the dual funnel that allows them to grow incredibly fast. That’s what you’ve introduced here. You essentially still have this great product with this great low-end price point. Great for consumers, not for your average revenue per customer but great for your customers, and you do have a mini brand with thousands of people that use it. Now, you also have this high-end enterprise offering and that brings that average revenue per customer up pretty substantially.
Craig: Yeah. We’re now getting into the third leg of that stool which is really cool. It has its own messaging challenges but we are having conventional podcasting, podcast editing as a service, and then private podcasting that is in some ways a whole other animal, a whole other product and whole other type of customer but is very interesting both from a revenue perspective and from a business and product and where we are on the market perspective. It’s cool and challenging at the same time.
Rob: I’m really interested to dig into this because when you talked about building private podcasting, the first thing I asked was is anybody else doing this? Why would you do it? I’m not sure I understand it but you guys are essentially on the leading edge of this. You’re stepping out. This is a novel, new entry into the market. That’s the thing. I was thinking, I’m sure it’s aimed at (I can imagine) any Fortune 5000 company might want a private podcast for their sales staff or for their employees in this day and age of working remote, but I could also see Startups For the Rest of Us having a private podcast that people pay a Patreon or a subscription for. I can see MicroConf having a private podcast for people who go to this event or for the Connect Slack Channel with only them. Or how about a TinySeed private podcast only for investors or only for mentors? Am I making this up or is that where it’s headed?
Craig: It’s literally anything you can imagine. We have mental health professionals having private podcasts for each of their patients. We have Fortune 100 companies that we’re working with having internal private podcasts for their sales team or for their HR groups. We also have enormous health and fitness brands having private podcasts as an extension of their membership site or their course. That’s tens of thousands of people coming in. They have a course or they have a membership site. They have content there and they want to add podcasting as another way to connect with their tribe or their members. We are really uniquely positioned. One, from our WordPress integration, that a lot of people do this membership type stuff in WordPress, so we’re a natural fit there. We also have some native integration with membership platforms like MemberSpace to where new members start paying you for access to membership sites. That person automatically gets added to a private podcast in Castos. All totally automatic that you as membership site administrator don’t have to do anything and you’re able to offer this to your members, which is a huge value. I think it’s just such a natural fit. Now that we’re here I think of course, why didn’t we do this a few years ago? Rob, it might be like what you saw with Drip where you weren’t ready, the market maybe wasn’t ready. Now—knock on wood—I feel like we’re at the right place at the right time with this because it’s a huge opportunity and people come to us and they are absolutely thrilled that we do this the way we do. That makes me feel really good.
Rob: It’s easy to think like a product person. The next feature I launch is going to be the one that changes it. Most times it’s not, most times you try to market it and it’s ho-hum. But this one seems to have really resonated in a way that I’m not sure I anticipated when you were talking about it. I’d hope that it would bring in the Fortune 1000 or 5000. You can charge a lot more for this because it is a premium feature, but the conversation you’re having with people on the interest of this, it sounds like has been really strong. Did you expect that or were you a little bit questioning or tentative about it? I know you were all in on building the future but did you expect it to have this level of interest?
Craig: I would be lying if I said of course I knew that this was going to happen. Of course, I was very hopeful, but I think you don’t know when you’re expanding the edge of what people expect from an ecosystem and a platform, and the behavior that they have with something like podcasting or email marketing. It is when you say you can charge money for a podcast directly or you can only offer this podcast to certain people. Even today, folks are saying that’s not a thing and you explain it to them. They go, of course, that totally makes sense. I can imagine doing this for X. When we started to have some of those initial discussions, then we had more confidence in it. We did a fair bit of collecting email addresses and chatting with folks. We had some people on the platform from day one that was duct-taping this together with Zapier and the membership platform and stuff like that but didn’t have that last piece of individualized private RSS feeds from the hosting provider. That’s what we are providing.
Rob: Right, so you can revoke access in essence when it happens. Congrats on getting that life and certainly stoked to hear about the interest. Obviously, as an investor through TinySeed, it’s nice to see when things go right and I get to live vicariously through your victories, which is fun to be along for the ride. I do want to congratulate you as we move to wrapping up. I want to congratulate you on hiring Matt Medeiros as your Director of Podcaster Success. If folks have not listened to the Audience Podcast and if you are interested in starting your own podcast, or growing your audience, or learning how to monetize, or all the tech stuff around podcasting, search for Audience in your podcatcher. I listen to every episode that comes out. It’s a really high-quality show. I can tell that Matt has pulled a burden off of you because I know that you were putting that out every week and I know it was a ton of work for you.
Craig: Yeah. It’s funny. Just before recording this, Matt and I recorded an episode and talked a lot about this, him coming on board, he is a better podcaster than I am and has been doing it for longer and it’s been awesome to bring in a total A player to own that part of the business. As an entity of the podcast, it’s much better off primarily in his hands. It’s been cool.
Rob: That’s a double win when they can do it perhaps a little bit better than you can and that you get the time back. You don’t have the mental burden of, what am I doing because producing content like this is fun, but it does take that good glucose. It takes that creative energy that you can’t put into writing copy or doing other harder things. As we wrap up, I want to hear what you’re excited about right now. What’s new with Castos? Whatever this week or this month? What’s kind of the big thing that gets you excited?
Craig: We have like two real initiatives that were driving hard on. One is doing everything we can to be the obvious choice for people who want to create a podcast and use WordPress as their website. Specifically what that means is we’re launching an integration with Elementor by the time this goes live. This will be out so you can manage all of your podcasts, design, contents, player, everything from the Elementor editor. Elementor is the most popular page builder for WordPress, so we’ll fit directly into the Elementor editor and all of your podcast stuff happens right from Elementor. That is super cool and hopefully opens up a chance to do some co-marketing and brand exposure between organizations. We’re doing more things in that kind of vein of the businesses, just doing cool things and offering good free tools for people on WordPress to make that experience even better. The other one is private podcasting. It takes a lot of different forms. I talked about courses and membership sites but also for internal company podcasts and working with real enterprises and what that looks like. The question mark still—we might have talked about this last year—is Castos directly being able to be the payment processor via Stripe, a way for you to charge money for your podcast directly. That’s still a bit of a question mark. I think it’s a question mark from a strategic perspective because I think about podcasting as a hobbyist and an aspirational thing, I can imagine a lot of people coming into a tool like this, like Substack. I imagine Substack has an enormous number of people that don’t make any money from their newsletter. If you think that what we’re talking about building with premium podcasting is the same kind of thing, you’re going to have a bunch of people coming in, making content, charging money for it, and not making any money. That’s just how it goes. It’s tough to build a community and a following online. It’s even harder to get those people to pay you money having the micropreneur academy, FounderCafe. We’ve taken the approach so far of let’s help people that already have a significant following, and integrating with their course platform, their membership site, or their community, and offering podcasting as something that they add-on at an additional way to that. From a project strategy perspective, I don’t know if going directly to people that want to charge money is the way to go. I’m sure we’ll do it but I think we’ve made the right decision so far to say let’s use the audience we already have and the membership tools that they’re already using to manage those members and payments and things like that and us be the podcasting tool that adds on to those, as opposed to having to—from a product perspective—create the whole stack and maybe have people come in that, think they can build a community, and charge people money for it because I think it’s just really, really hard. We’ll see.
Rob: The aspirational people will come but I think you can get around that with pricing. I’m just going to throw up pricing. If it’s $99 a month plus whatever for downloads or something then you’re not going to get as many aspirational because they’re going to say that’s too expensive. If I had MicroConf as an example or Startups for the Rest of Us, $99 a month is a no brainer for us. Certainly for whoever, Target, General Mills, and Best Buy, these are just Fortune 500 companies that are here in Minneapolis that I was thinking of. For them, it should be even higher. I guess Best Buy, Target, and General Mills are not going to charge their people. That would only be for someone more like Startups for the Rest of Us or MicroConf if we did decide to make that a paid thing. Again, if you just keep that minimum price at a certain point, because you’re not a commodity right now. You’re such a unique offering that if people want it, they need to come to Castos. Once the feature is going to get cloned, you get copy cats, they probably won’t build it as well as you guys have. Eventually, it will get to that point and you have to make that decision of, do we want that lower-end of the market, the aspirational people, but I guess you can make that decision when you get there. Is it something you feel like you could solve with pricing by just having that higher minimum per month?
Craig: I think so, but I think that all that does is it doesn’t attract the aspirational folks that don’t already have that audience or don’t think they could get that audience. The thing that I’m most concerned about is this resource allocation of it’s a month’s worth of work for a developer at least to build all this stuff, could we go do something better with that?
Rob: I want to see it that you have ample leads coming in on that higher-end that want to charge for it. If you’ve only had a handful come in then I don’t know. If you haven’t lost a deal because you don’t have it built-in and it’s a month of work, that’s tough. Given how fast you have to move and how much you’re building, it’s a tough decision to make.
Craig: That’s definitely a question mark. It would be super interesting but I’m not sure.
Rob: Well, awesome man. Thanks again for taking an hour and hanging out with me here again on Startups for the Rest of Us. On Twitter, you are @TheCraigHewitt and obviously castos.com if folks want to see what you’re up to. Thanks so much for joining me again this week. I hope you enjoyed that conversation with Craig. I’ll definitely have him back again in the future. He always has interesting insights, is moving so fast, and doing so many interesting things that it’s pretty easy to bring out essentially good conversation and good content for here on the show.
Episode 521 | A Roundtable Discussion about a Potential Recession, Working from Home, Google Anti-trust, and More
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Episode 521 is a roundtable episode where Rob brings on a couple of guests to talk through topics today that relate to bootstrapped and mostly bootstrapped startup founders.
Today, we have Tracy Osborn and Einar Vollset joining us, as we talk through a potential impending recession, the Google anti-trust suit, Dropbox moving to permanent work from home, as well as a handful of other topics.
The topics we cover
[04:03] What do the revenue trends look like in 6-7 months from now?
[13:36] Google anti-trust suit
[19:23] Dropbox remote offices
[27:29] SPACs and why it’s so hard to go public in the US
[39:35] A warning about Glassdoor
Links from the show
- The 99 Investor Problem
- U.S. Accuses Google of Illegally Protecting Monopoly
- Dropbox will let all employees work from home permanently as it turns its offices into WeWork-like ‘collaborative spaces’
- The TinySeed Investment Thesis
- A Warning About Glassdoor
- Tracy Osborn | Twitter
- Einar Vollset | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify | Stitcher
Rob: Welcome to this week’s episode of Startups for the Rest of Us. I’m your host, Rob Walling. Each week on this show, we cover topics related to building and growing startups using an ambitious yet sustainable approach. We’re not willing to sacrifice our health or our relationships to grow our company. We view relentless execution and a long-term mindset as things that we value. This is episode 521. Speaking of long-term mindset, we’ve been doing this show for over 10 years. Today, we are tackling some news stories. This is a startup roundtable episode where I bring on a couple of guests and we talk through topics today that relate to bootstrap and mostly bootstrapped startup founders. Today, I have Tracy Osborn joining me. Tracy’s been on the show many times. She is the program manager at TinySeed so we work together on a day-to-day basis. She is the founder of a startup called WeddingLovely that she worked on pre-TinySeed and shut it down shortly before joining us. My other guest is Einar Vollset. He is my co-founder in TinySeed. It really is a trio of TinySeed folks here today. Einar co-founded TinySeed with me. He does a lot of the investor relations work and works in the accelerator as well. He also founded Discretion Capital, where he helps SaaS founders who are doing $1 million or more in ARR sell for revenue multiples. He’s been on the sell side of SaaS for quite some time. It’s a good panel discussion today. We cover topics ranging from a recession impending. We talk about the Google antitrust and how that may or may not impact our types of companies. We talk about work from home, DropBox going to permanent work from home, and a handful of other topics. Before I dive into that, I got some good feedback—both constructive and some positive feedback—on TinySeed Tales. The final episode of season two goes live here in just a couple of days. I heard from JJ who said, “Love this episode’s great stories and excellent content about the challenge of being a startup founder.” From Dan, he said, “I love listening to this format of the podcast. I find them really interesting and entertaining, as well as hearing some of the smaller scale problems that bootstrappers face. They remind me a little bit of the first Gimlet Series which I truly enjoyed and wish was still around.” From Kyle, I got some feedback saying, “I like the general idea. I did stop listening to season two after a few episodes. I’m a little fuzzy as to why I stopped, but I want to say it didn’t seem as if I was going to learn that much from the company or from the episodes. I’m thinking what would’ve been more intriguing is if you were in more of a cultural and I get to hear you coach them more. Again, if I recall correctly on season one, Craig was further along and he was experienced so you coaching him seemed less critical, but in this one, I felt like I wanted to hear more of your voice on their journey.” We really appreciate everyone who wrote in to me. This was just a sampling. Again, I’ve received both positive and constructive feedback on it. That is what I’m looking for to figure out, (a) should we continue to produce the TinySeed Tales episodes? and (b) what changes we should make to the show format as we move forward? With that, let’s dive into our conversation. Tracy, thanks for joining me on the show today.
Tracy: Yeah, happy to be here.
Rob: Einar, you as well.
Einar: It’s very good to be here.
Rob: It’s good to have the band, I was going to say back together, but this is the first time the three of us were appearing on the podcast. I think it’s cool. You both have made multiple appearances over the past 12–15 months, but I haven’t done too many of these. I get a lot of requests to do the three- and four-person news roundtables, but they tend to be pretty hard to plan. The logistics are tough, and then it’s oftentimes hard to find enough topics that really relate to our crowd. We can talk about stuff that is broader news. Jason Calacanis says this with great success on This Week in Startups, but he’s relating it to the world. He’s talking about trade policy and this and that, and I find that it can sometimes be hard to link that back to boots on the ground, MicroConf, Startups for the Rest of Us, TinySeed-type startups. But I do think we have a good docket today. The first topic we’re going to cover is a listener question about the economy. It’s from an anonymous listener. He said, “Early on in the pandemic, you described a broad revenue trend along the lines of, about 20% of companies that you’re invested in or had the financials off their way down, 60% had a minimal difference and 20% are way up.” This question asker says, “Hey, we actually landed in that 60%.” I said that off the cuff one day and then I came back to it a week later. I looked at the numbers and it wound up being closer to 15%, 70%, and 15% for what it’s worth. Give or take, it doesn’t really matter. He says, “So, here is the question. It’s 6–7 months later, what does that picture look like now? I suspected a lot of us in that initial 60% group are starting to feel signs of a real recession. Maybe a few extra customers churn, maybe customers feel renewed but get lower users. The effects aren’t huge, but they’re there. My sample says it’s small but I’m seeing it. It’s not falling revenue but it’s flat where I had expected growth. There’s a lot of reasons why people don’t want to admit this stuff. Revenue failing to hit forecasts is not a good look. Disappointing looks are hard to face. No one wants to consider the implications of that for themselves or for others. If other startups out there are seeing signs of this, it might be helpful for the community to know what to look for and what to do about it. My business is fine and we have a broad customer base, but I’m curious to see what you’re seeing out there in the space.” Einar, you want to take this first?
Einar: Sure. My view is things haven’t changed all that much. I still think the breakdown is roughly what you said. Particularly SaaS businesses that are serving industries—whether that’s travel, schools, or restaurants and things—I still think they’re hurting. I don’t think it’s quite in the same deep freeze as it was back in March–April time frame but certainly, a lot of those companies are still hurting. I don’t think it has expanded necessarily. I do think on the other 15% side, the growth spurts that came for the winning companies have slowed down a little. We saw some companies, in particular—before COVID were growing 30%, 40%, 50% a year—who all of a sudden grew 100% in 3–4 months because they were at the forefront of whatever, work from home, or something that’s COVID-related. We’re starting to see more normalization for these guys’ growth rate. Some of them are back to where they were, 30%–40%. Some of them are coming down off the peaks and perhaps stabilizing at a higher base. Certainly, that’s true (for example) with things related to ecommerce, delivery things, and stuff like that. In the middle, I don’t know, actually. I’m not 100% sure. I feed bad for the question asker. I want to say, yeah, that’s what I’m seeing all over, but that’s really not fully what I’m seeing or at least hearing. People are still tentative. Budgets are harder to get on and approvals are a little harder, but I’m not sure that it’s going to slow down into the fall, from the people I talked to, anyway. It’s peculiar to this small sample size.
Rob: Tracy, you have insight into at least 23 companies across TinySeed batch 1 and 2. What are your thoughts?
Tracy: One thing I was wondering about this question in terms of timing—and I was going to post a question to you, too—was the possibility of things sliding to a recession, but also worrying about that happening while we’re also going into the holidays. What is the drop in growth? Is that something that happens with startups? It’s something that happened with me in my previous startup because we were so…
Rob: Seasonal?
Tracy: Exactly, we were a seasonal startup. I was wondering if people were like, oh, should I be worried about a recession if it’d be worthwhile to go over what you just see go into the holidays—keeping in mind that holidays are in COVID so things are going to be weird—versus if it’s a recession, how that’s affecting your business.
Rob: My thoughts there are obviously if you’re an ecommerce, Black Friday’s coming up. Any type of ecommerce SaaS, software, or whatever is going to be going up into the right over the next month, and then it’ll drop down in Q1. I saw seasonality in all of the companies that I’ve run. It wasn’t seasonality; it’s too strong. I would see (usually) dips in growth, especially if it was SaaS. It wasn’t the revenue drop, but it was the growth that would slightly decelerate. We get fewer signups right around tax day in the US—mid-April—and then around December. I was counting it lucky if December grew at all. If we stayed flat, that was fine, but I really wanted to have a good November. Then, we would come out swinging pretty hard in January. We often launch big things in January.
Tracy: That’s exactly what I was getting at. I’m curious to see how things would happen in January, also depending on US politics, where we are in COVID. This going […] and getting at is, is it too early to say about the recession, being that there are other things going on?
Rob: The uncertainty of COVID, the uncertainty of US elections and holidays coming up, I can see them making people uneasy and not wanting to purchase. The question asker, his business is flattening or not growing as fast. It could be justified by that. I’m invested in between TinySeed and my independent staff. I have 35 investments, and I’m not hearing that there’s slowing down. I’m not seeing plateaus or slowing across the board. There are two questions here. One of them, I may be answering with no, I don’t think everything is flattening right now yet. The second question he’s asking implicitly is, do you think there is a recession on the horizon when we look out 3–6 months? For me, it’s a big I don’t know. I was talking in 2015–2016, there has to be a recession coming. There was in 1989. Well, no. There was one in 1993, there was one in 2000, there was one in 2008. I kept thinking it’s not that it’s every seven or eight right years, but this has been going on, the stock market’s really overpriced. When I sold Drip and had all this cash, I remember just agonizingly investing in the market. I was like, I’m waiting for this thing to be cut in half any day. That really didn’t happen until COVID. It happened in January of 2016. There was a big correction but it came back the next month, so there’s no recession there. The next big hit obviously was when COVID started, but it was so short-lived that I don’t know what’s coming.
Einar: Well, it was short-lived. There’s sort of a binary outcome to start. I don’t know if we’ll be turning to a stock discussion program here, but if you look at the companies that are listed on the stock industries, you see that basically the reason it’s recovered is because of the big tech firms like Amazon, Facebook, Twitter, Zoom, those kinds of things. They’ve done really, really well, versus the Russell 2000 which was the small-cap companies that are listed. They really haven’t recovered. They’re still down 20%–30%. It’s been a story of two different trade industries, which also partly backs up my view of the market. This relates to M&A, too, in the software space. It’s been very strong. If you’re in software or anything semi-positive, like you had tailwinds for at least the last few months now. Today, I think the Dow is down 3%. There’s obviously a lot of uncertainty around the elections. Who knows what’s going to happen with the vaccine and things, but certainly, the last 3–4 months, if anything, I’ve seen tech firms have tailwinds through the last few months at least.
Rob: I think you’re combining two things because you’re talking bear market, bull market, and stock prices, and I’m thinking more recession or not. I’m thinking of SaaS companies just getting started to several […] and revenue, mostly bootstrapped, are they still growing? Even about the retail store here in town, they don’t necessarily care about the stock market. It obviously impacts the broader economy, but when I think about it, if I was running a SaaS company today—whether I was doing $100,000 a year or $5 million a year, and I was, again, bootstrapped or mostly bootstrapped—I would be slightly cautious right now because of how much uncertainty there is. None of us can predict a recession, but there are a lot of things that can go wrong in the next six months. Personally, I’m fairly risk-averse especially when I’m running a company that I don’t want to lay people off. I don’t want things to go to zero. I don’t want to miss payroll or whatever it is. I would be thinking about being a little bit conservative or having a little more of a cash cushion than I would have in the boom times. I mean, you go back a year, you don’t need so much of a cash cushion if you’re going 10%–20% a month. Right now, I would be thinking about, what are my plans B, C, and D if things start to go sideways here? What if growth flatlines for six months, are we good? I’ll be asking myself some what-ifs and figuring out which of these could be company impacting
Einar: Yeah, I think it’s fair. And buy some Bitcoin, obviously.
Rob: Oh my gosh. Tracy, you’re on crypto?
Tracy: My husband is very into crypto, but I am not. I’m sorry, I’m going offhanded here. It’s fun being adjacent to that world but then listening to Einar and his thoughts.
Rob: Einar is just in it for the big score. I definitely know crypto that people who listen to podcasts know that I dollar-cost averaged in. I blend it on these big runs because right now it’s up. I do a little with a dollar-cost averaging out, so I feel good about that. Our next topic is a story from the New York Times, and it is about the Google antitrust suit. The US accuses Google of illegally protecting a monopoly, the Don’t Be Evil moniker that Google had for many years. A lot of us especially small startups who have experienced whether it’s direct competition, whether it’s being stepped on accidentally, whether it’s having AdWords constantly being more expensive, whether it’s having our keywords be not provided, whether it’s having them not send us traffic because they’re doing snippets at the top of the homepage, I definitely think there is a sentiment in early-stage startups that certainly, Google’s doing something that may not be fair or encouraging of the ecosystem. Tracy, what are your thoughts on this antitrust suit and how do you think it impacts the startups in our community?
Tracy: Google just feels like it owns everything. It has its fingers on everything intact, and you can’t avoid them. People are still talking about Superhuman—this other email thing—while everyone’s like, oh, but Gmail’s the best. You’re like, okay, I won’t talk about advertising, Facebook advertising, Reddit advertising when really, Adwords is a thing you have to start out from. You get a new phone, and Google is on your phone. That’s what you said earlier, that’s a lot of these antitrust cases about the phones and everything coming with that bi-standard. I’m a fan of any kind of breaking up at least a little bit because I feel like Google being in all these areas and having its fingers in everything is slowing or preventing some amount of startup innovation in those spaces. What will we see if Google wasn’t number one in everything that we do? In some way of breaking it up and allowing for more innovation from people, where would tech be if Google wasn’t the behemoth that it is right now?
Einar: Ditto. I broadly agree with that. The specific case that the DOJ brought against Google is pretty narrow. If you read it, they’re saying like, okay, it’s antitrust to protect their search monopoly by paying billions of dollars to Apple and whatever to make Google their default search platform. Broadly, I agree. It feels a little bit similar. It’s like Google is walking towards the situation that Microsoft was in years ago back in the 90s. Microsoft was the big bad wolf that squash you, outcompete, buy you, or do whatever. It’s funny that basically, Microsoft got sued by the DOJ for antitrust when they were 22 years old, and Google is actually 22 years old this year. It’s almost like a college graduation thing, like, congratulations, you made it, here is a lawsuit from DOJ. You look at what happened with Microsoft when they did face that sort of thing. That’s overall been good for the startup ecosystem, that stranglehold that they had on tech. There are two ways to look at it. Either the fact that they go sued and things open up some innovation, but then the flipside of that, too, is people have to work around that monopoly to a large degree. That’s why you get WebApps and things when you did in the early 2000s. I don’t know. It’s one of those really big market-moving things, a direct impact on bootstrap software entrepreneurs. It’s more TBD, to be honest with you.
Rob: The big thing that I’ve seen Google do over the past 15 years as I’ve been more involved in the ecosystem, as I’ve started running Adwords, that has been anti-innovation or anti-startup directly, is this slow titration or this decrease in the amount of data that they give to people who are trying to market their businesses. When I started pulling keywords out of Google Analytics, they give Not Provided instead of the actual keyword people were using to search their site. Before Not Provided, I was a small business that was marketing on the internet. I was either doing SEO or was buying AdWords, but it would tell me, hey, they clicked through this keyword and they converted. This keyword converts really well for you. They pulled it out and they gave some […] excuse about it being privacy. First, it was only SSL and then they just rolled it out to everything. What it did is it forced you to buy ads from them. If you buy their ads, they give you the keyword. So how is it so? It never made sense. There was a bunch of uproaring, and Google said we don’t care. Then, they slowly pulled all the data out. Their keyword tool is completely useless now. They said they would never sell search rankings, but if you just search for any term, the top three, four, five positions now are all ads. The organic number one is oftentimes below the fold depending on how many things you have on your screen. You can’t even identify the damn ads. It’s a tiny little box. I had to teach my kids that those were the ads. My mom still—I’ve watched her using the computer—clicks on the top result every time. I’m actually like, oh, you just cost that store money. She’s like, why? I was like, well, you clicked on their ads. She’s like, how is it an ad, it’s a top search. People don’t understand. That’s not what this suit is about. This suit, to be clear, is about the default search engines on these mobile devices. It’s all intertwined. It’s a lot like Tracy said. They are everywhere. Do I believe that they have used monopoly-like powers to just throw their weight around and not care what the market says? I do.
Einar: Oh, yeah. Just ask Mike Taber. The hoops he had to jump through to be able to get to what effectively is the default email client in the world. That’s something that Google can do. All the big boys do it. Twitter is famous for yanking their developer API after the developer helps them become famous and become popular in the first place. I agree with that.
Rob: Our next story is about Dropbox. I’m reading this on businessinsider.com. By the way, we will post all of these stories in the show notes. The headline of this story is, Dropbox will let all employees work from home permanently as it turns its offices into WeWork-like collaborative spaces. Shouldn’t they just say coworking-like collaborative spaces? Why does it have to be WeWork-like? That’s interesting. It’s like saying, Kleenex instead of tissue, or Band-Aid instead of a bandage. Anyway, in essence, Tracy is this just the rest of the startup world? The Silicon Valley startup world is finally catching up to what bootstrappers have been doing for the past 10 years because we didn’t have the money for offices?
Tracy: No kidding. There’s a lot of negative effects from COVID and the effect around office spaces. There are just these norms that once you got to a certain size, you had this office space. What was it? Yahoo! used to let you work from home, then Marissa Mayer became the CEO and she rescinded that because that was the norm. Yahoo! is innovative before but they’re using that as an excuse to bring in […] back in when she was there because she said that everyone works better together. Bootstrappers know that you can’t get just as good work done remotely but all these companies were facing this norm that was pervasive. Finally, COVID is forcing people to make this change. Now, these big companies are waking up to this idea of, hey, you’re not having your employees drive an hour or two from the office. They have simpler lives. Maybe, they’re getting more work done because they’re faced with fewer distractions from being in the office. I’m looking forward to seeing how this plays out in the next year. Hopefully, as COVID gets better and maybe things are opening up again. I’m hoping that like Dropbox, these other co-companies will also have these policies put in place and that employee’s lives, hopefully, will match something a little bit closer to how bootstrappers have learned to work from home or at least have learned to work from home.
Rob: Einar, you live South of the Bay area. I bet you’re seeing lower traffic now that people are working from home. Do you feel like this is going to change the landscape of these big campuses? I know Facebook. My brother and dad worked in the electrical contracting industry in the Bay Area for years. They were part of doing work on the massive Google campus, the massive Facebook campus, the massive CISCO campus, and all of that stuff. Is that done at this point? Do you think most companies are going to wind-up going at least half remote or work from home permanently?
Einar: I don’t know. I’m torn on this whole subject just like the resident extrovert here. I certainly think like some of the traditional views. I saw some venture capitalists on Twitter making a big deal about the fact that they’re no longer going to make it a requirement when they invest or a qualifier that a company has an office before they invest, which I always thought was really stupid. On the other hand, I do think there might be backlash once the vaccine’s in place. I feel cooped up just in my home office, not seeing people just day-to-day. There’s value in interacting directly face-to-face with people, but there will be a fundamental shift in the expectation probably mostly from the employee side. It will probably start with tech companies and then trickle down where maybe they’ll be there a portion of the time. Maybe they work from home 2–3 days a week and then in the office a couple of days a week. What Dropbox is doing is smart because that facilitates that thing, which, in general, is a good thing. We’re already seeing it just in the real estate markets in the Bay Area. The shift where it’s not a good time to own a one-bedroom condo in downtown San Francisco because everyone is just moving out and buying cheaper, bigger places elsewhere. It’s definitely a trend, but do I think it will become everything is remote-first and offices are going the way of the dodo? I don’t really buy that, but I guess we’ll see. In general, commercial real estate is a bit screwed, particularly in California if Prop 15 passes where the tax increases and things. I don’t know what they’re going to do. It follows on from the fall of shopping malls because e-commerce has taken over. They’re just empty malls everywhere. What are they going to do with all of that real estate? The questions are almost the same even if it’s a small trend, like you say 20% of companies or 20% of employees don’t go to offices regularly, that’s a big drop in the occupancy rate of these places. What are we all going to do with this office space that isn’t being used anymore?
Tracy: Couldn’t we convert some to housing?
Einar: That’s what I think. There’s a mall in town where I live. I looked at them and I’m like, why isn’t that converted into an apartment complex at this point? I don’t think that this is going to fill out again in any way, shape, or form. I don’t see why it can’t be a hybrid: partial apartments and partial shopping-restaurant complex. That stuff takes time, I guess.
Rob: For me, I’ve always been a believer that a lot of the companies that have been remote—the larger companies, let’s say a company with 50–500 employees that is remote—tends to be a lot of introverts. They do tend to hire people who work well remotely. We haven’t done an experiment this large, to your point Einar, with companies that didn’t hire specifically for remote workers or have more extroverts, just more of an extroverted workforce. We got the balance right with Drip when we’re in Fresno. There were 10 of us, and there were some people that were fully remote. They were in New York and I went to other states to find the best people; that’s what I had to do. Everyone in Fresno, we came to the office two or three days a week. The third day was optional. I saw Derek, I saw Anna, and I saw my co-workers. When we sold, we moved to Minneapolis, it was three days a week mandatory. It was Monday and Thursday, everyone had the option and most people just work from home. That is such a good arrangement, especially if you have to do any type of maker time. When I’m at home, I would try to block off and not have as many meetings on those days. I like to keep the mornings to myself, and I would have zero interruptions. In the office, I got social time. We did a lot of whiteboarding, but I get interrupted all the time. At a certain point, I said, I’m no longer a maker. It’s just not going to happen in an open office space. I hear you on that. I don’t know if there will be a transformation of these office spaces into living space, if they alter the form into escape rooms and trampoline parks. I see a lot of these warehouse districts. That’s a thing. It will hurt commercial real estate. The rates on a startup office space are higher than the rates you can charge a trampoline park or whatever innovative new entrepreneurial thought does come out of this. There will be a hit but we’ll just have to see how back to normal things get once there is a vaccine and things start to clean up.
Einar: That’s true. Even if you just take your example, if the majority of companies end up adopting what you’re saying, that’s two days out of five. That’s very low-low.
Rob: Yeah, then we’ll have to figure out, we just paid the rent as if we used it because we had it for 30 days a month. We had it 365 days a year, we just didn’t use it all the time. That was the decision we had to make.
Einar: You could end up with a scenario where two companies split it. You have Monday, Tuesday, Friday, or maybe both of them come in. Everybody comes in on Fridays. That’s a big party. You can see those types of situations.
Rob: Yeah. The fact that WeWork has had some major issues and has tanked pretty bad, but can you imagine if there were a more successful, more sustainable model that a lot of these are just turned into shared office space, into more of a WeWork model. I wonder if there becomes an opportunity, there’s that old phrase of like, I want to be the second buyer of everything because the first buyer, the first investor puts a ton of money in, they burn through it, they prove out the model, and then when that goes out of business, I can buy it for pennies on a dollar. Now I have this asset that there’s an opportunity. I wonder if there isn’t going to be that in commercial real estate in terms of office space. Our next topic is an interesting one. Listener, follow me along with this. This isn’t as relevant to someone who’s running an extreme early-stage startup. I know more than one founder who has hit the point where they’re doing (let’s say) $2–$10 million in ARR, they go to try to raise money, and they don’t want to go the venture unicorn track, but they do want to have some liquidity perhaps for themselves or to pump into the company to continue to grow. There’s a couple of things that tie into this. The bottom line is due to the regulations in the US, it’s virtually impossible to do that. It’s not worth it because of the high expense of going public in the US. First is in Canada, there’s the Toronto Stock Exchange and in Australia, there’s (I think) the Australian Stock Exchange; I forgot the name of it. In Toronto, if your company’s market cap is $4 million, you can go public on their exchange. The fees are between $10,000 and $200,000 depending on how much money you raise. It’s actually quite inexpensive. You could imagine a SaaS app, much like you would meet at MicroConf who’s doing $3, $4, $5 million a year going public. The phrase ‘going public’ has such gravitas with us. It’s like only GE, Apple, and Google are public, these are master companies, but I don’t think that should be the case, actually. Einar, you want to walk us through a little bit? We have a couple of topics to touch on here. One, why the hell is it so expensive and hard to go public in the US. And then, the real topic that leads us into is these things called SPACs which are Special Purpose Acquisition Companies and they’ve been in the news quite a bit lately. I’ve heard them on This Week in Startups and there’s a Forbes piece on them. They are suddenly becoming a popular way to go public in the US.
Einar: It is slightly strange. I think most US investors don’t really look abroad. They just think this is the way it’s become. The trend over the last 10–15 years has become that even though this (perhaps) does not have your regulations than they already were, you end up in a scenario where a company like Airbnb is going public after (maybe) 12 years of existence instead of the more typical which is a decade or plus ago with 4, 5, maybe 6 years. It is slightly weird to me that you have to be one of a small number of unicorns in order to go public. As you mentioned, that’s just not the case in other countries. There are dedicated exchanges like the TSX Venture Exchange in Canada. Being Norwegian, I know there’s one called […] in Norway. There’s a couple of ones in Germany. Basically, people understand that if you’re buying stock on this exchange, then yeah, there are some compliance and things, but these are much riskier bets than your GE, Google, Apple or things like that. On a philosophical level, I don’t really understand why that is impossible. Investors can go on the Robinhood app—like I did—and buy a bunch of put options on United thinking that Donald Trump is going to announce some sort of a vaccine before the elections so it’ll jump up. You can lose all your money as I did in a week. Nobody’s stopping you. There’s no accreditation process or doing that. The stock market is, as we in part of seeing through COVID, to a large degree is a good way to lose a lot of money very quickly. But fundamentally, I think one of these things should exist in the US where if you get a certain size, as you say, $5–$10 million in ARR, why not go public? Companies like that go public all the time abroad. It gives access to retail investors who don’t have access to private markets. Fundamentally, the fact that things take longer to go public means that the average investors who don’t have inside access don’t get to participate in the value creation there. I think I actually like SPACs—to circle back to the topic at hand. SPAC’s a sort of a symptom of this problem. SPACs are basically like empty shell companies that people put together and they go public. They list an empty company, the company basically says, we’re going to sell $500 million worth of stock in our company—in the shell company—and then turn around, use that capital to buy or acquire a private company. Effectively, it’s like a backward IPO almost. The company becomes a public company by virtue of being acquired by the shell company. My view is that that sort of a symptom of how complicated and how long it’s taking for all of these companies to go public. I think we’ll start to see more and more of that trend. I’m sort of pro at it. I don’t think there’s any reason why more companies shouldn’t be public so that more investors get access to the value creation that obviously happens there because you get to $10 million, as you say, what’s your option at this point? It’s to sell to private equity, to sell a portion to private equity for some liquidity and things. But are they really giving you the best price? Wouldn’t it be better to just sell 20% of your stock to the public and not have basically one boss who may have the wrong view of how you should grow and what your strategies should be going forward?
Rob: Yeah. I think SPACs are kind of a loophole or a workaround to what I would say an overly regulated, overly complicated system. I certainly think there need to be investor protections. Yes, most of the laws that are governing all of these were written in 1935. They haven’t really been updated. There was the jobs act that was a little bit for crowdfunding, but really, there are still a lot of problems with what’s going on today. Tracy, you’ve witnessed it first hand as we’ve been raising funds for TinySeed Fund II. Einar came back to us because he was doing research and he said, if you raise a venture fund, which is what TinySeed’s raising and you’re raising more than $10 million, the highest number of investors you can have in that fund, these are accredited investors who either have a million dollars or more in liquid net worth, not including their primary house or they have an income of $200,000 a year for the past two years or $300,000 if they are married. To put this, the definition of a sophisticated investor in the United States, even then, you can only have 99 of them in your fund. If you want to raise, for example, a $40 million fund, you need people to give you your minimum investment to be $400,000 per as average out to that, which is kind of crazy. Because if you could have a thousand investors, then you can drop your minimum way down and you could make it more accessible to so many more people. I think given our love of what we are doing and our belief in this space, that we would prefer for more people to be able to participate. But I’m curious, had you heard of this 99 investor problem before now and any other thoughts on it?
Tracy: This issue really goes back to me as someone who isn’t an investor, has always dreamed about becoming an investor, kind of a baby investor. Coming into TinySeed, I had no idea about what went into raising a fund and being a part of a fund. TinySeed’s thesis, which you put on our website—working here, I totally agree with it—we’re talking about TinySeed being an index fund into B2B SaaS. When you’re talking to people who can be a credit investor, that those require you have before but maybe just barely meet those requirements, a lot of people are very into the mission we’re doing, a lot of people don’t have $400,000, but they’re like, hey, this sounds like a winning bet to me. I love to put it in 5000. It sucks to be like, no, we can’t. We can only talk to the people who already have enough wealth that they can just blow this massive amount of money into TinySeed. It creates this problem between wealth equality in a way that people who are coming from disadvantaged backgrounds have a hard time getting to that level of wealth to be able to throw around that amount of money. When we have something like TinySeed—again, I totally believe in what we’re doing, think they were going to be a success—I want to help other investors, especially from disadvantaged backgrounds, also be a success with us and we have to constantly tell them no. It just drives me absolutely at the wall. The fact that the 99 investor problem exists—Brad Feld wrote a blog post about this if you Google for it—it’s frustrating. And because in 2018, President Trump signed (I think) the startup act or whatever, that was hoping to solve this problem between 99 investors being allowed to invest to be in a fund by opening it up to 250, if I recall. But that only applies to funds that raise less than $10 million, which is ridiculous, because the funds are raising more than $10 million and need to have more number of investors who are able to invest in it. I feel like it’s a huge issue. It leads to the restriction of wealth growth to these already wealthy people. It’s like I can go to a casino, I can spend $5000 in a casino, and no one would bat an eye. But I can’t take $5000 and try to invest it in some larger fund which, because they’re kind of indexing, arguably might have more chance to succeed that’s not allowed for me because those funds are restricted to only large investors. It’s just bananas.
Einar: I obviously agree. I talk to investors all the time and I tell them, I’m sorry, our minimums are minimums. People get frustrated and they’re like, you know, I want to put $50,000 into this. Often, they’re successful operators. They’re people who maybe bootstrap to SaaS business, got it to a million or two, sold it, and now they want to put some money into the area that they understand. In part to support the community and in part to obviously make a return. The crazy thing is, it’s already even worse than that because technically speaking, there are two definitions of investors. There’s more, but the main ones are the accredited, which is what you’re saying. Really, then you’re a pretty wealthy person if you qualify as an accredited investor. But there’s a higher threshold called a qualified purchaser. Basically, what a qualified purchaser is is somebody who has at least $5 million in investments. That’s obviously wealthier than someone who is “just an accredited investor.” But the funny thing is, that you can actually take off the 1999 qualified purchasers. What that means is, our minimums, and any fund’s minimums can be lower for the wealthier investor. Which doesn’t make any sense. I can take $5000 from you if you want to, but only if you’re worth at least $5 million. If you are “only worth $2 or $3 million,” well, I’m sorry, but then I have to take $400,000 or whatever the minimum for the fund size is. That doesn’t seem to make any sense to me. I don’t know that I’ve ever read a good reason why the limit is 99. I don’t understand why it should be like a thousand. You don’t want something that turns into a scam, then gets a million investors caught up in it, but 99 just seems really arbitrary.
Rob: If it was a million then it’d be a public company. If you had that many […] public. But you’re right, there’s a big difference between 99 and a million. We’ll see what happens. I’m just throwing my hands up and being like, somebody needs to figure this out because I do believe this is hurting innovation. Much like the high cost of healthcare in the United States, I think the regulation around going public and the regulation around 99 investor limits on funds, those three things are the things that I have experienced first hand over the past year or two, that are seriously impacting the startups that I’m working with. Not only with TinySeed, but just all around MicroConf and the people listening to Startups For The Rest Of Us. Hopefully, we can do something about it and I would be remiss if I did not recommend people go check out tinyseed.com/thesis. If you click through there, you can of course send Einar an email. You fill out a form and he gets an email, and you could chat with him to hear about the TinySeed thesis and to hear more about what we’re up to and how we’re raising that fund. Our last story of the day is from Reddit and it’s a warning about Glassdoor. The person says, “For the past few years, I’ve often defended Glassdoor as a useful resource, as part of any job seeker’s overall job-seeking toolkit. About a year-and-a-half ago, I interviewed with the company that had horrendous reviews.” This is a thousand […] summarized from here. In essence, there were a lot of negative reviews, the person took the job anyway, the job was not good, and the environment was toxic according to this poster. They wind up going back to Glassdoor and posting a negative review, that then not only got removed but every one of this person’s reviews on Glassdoor was removed. They implied at the end of their post that they’ve heard that Glassdoor has supposedly done a minor pivot into brand management so that perhaps it’s becoming less reliable than it’s trying to get rid of negative reviews or something to that effect. The question I have is maybe two-fold and we’ll start with you, Tracy. Glassdoor has tended to be a bit of a mixed bag, but I’ve used Glassdoor quite a bit for salary recommendations which I find to be pretty reliable. I also used it back when I looked at lead pages, Glassdoor as an example when we were talking about being acquired by them. There have been companies where I have tried to research whether I think they have a positive or a negative reputation with their employees. I have always wondered, much like Yelp and much like Amazon reviews, these things do get gamed eventually. I’ve always had in the back of my mind, I wonder how reliable these actually are. Do you have much experience with Glassdoor and what are your thoughts on this whole topic of can this be a game, do we think that as something gets big, eventually it just does lose its value because they can’t control the potential review spam?
Tracy: It’s just funny to me because I’ve never used Glassdoor other than for salary information like you mentioned. A previous company I worked for had Glassdoor reviews and they were terrible. It was the funniest thing to me. I believe one of the large reasons why they completely renamed and rebranded the company was because their Glassdoor reviews were so terrible and they needed to have some way to wipe the slate clean. This was about seven or so years ago. There are probably a lot more systems to game it now. But back then, you just had to wipe the slate clean in order to get rid of those past reviews. I have checked them recently and they have better reviews before. I assume that they made some management changes in addition to rebranding the company. It’s definitely been games in the past in a very complicated matter like that. I absolutely think it’s being games now. I read that article, that Reddit post they are mentioning. It’s just like Yelp. All these companies are going to be very concerned about their reviews because it’s going to vastly affect the quality of the employees they get. Savvy employees are going to leave bad reviews and they’re going to stay away. Now, these companies are going to be doing whatever they can to either with Glassdoor or otherwise to scrub those reviews just like Yelp. I think what’s going to happen, just like Yelp, I think people are going to use it less now that these things are coming more in the forefront. But I’m curious to hear what you two say about this.
Rob: I’m wondering if this does open up the door, the opportunity for a new Glassdoor competitor to come in and have a better algorithm from the start or some other way of validating this stuff that then becomes reliable for a few years and then the same thing happens. Einar, do you have thoughts or experiences with Glassdoor?
Einar: I don’t have much experience specifically with Glassdoor. But I do think in general, anonymous reviews of things, I think it’s prone to gaming in general. I think you’re right. I think there’s probably a way to make Glassdoor not so easily gameable, but it doesn’t surprise me at all that companies will want to try to do it. Like I said, one of the hardest things—recession talk aside—is to get people to want to work for you, to get quality people to do, and if you have a horrendous review on Glassdoor that says this is the worst place in the world to work, that’s going to be a problem. I think in general. As I said, it’s a little bit like Yelp reviews. Do you really know or is it somebody who has a real aversion to creamer in their coffee and this particular way that this café does it and decides to make it their mission to take this café down? That’s hard to know.
Rob: Yeah. Obviously, if you listen to this, you’re probably at a pretty early stage. Maybe 0 employees, maybe 10 or 20 employees, I do think at least for now that people will go to Glassdoor. If you have no profile, that’s probably fine, because you just say, we’re so early that we don’t have one. The danger is, if you don’t have a profile, someone leaves a negative review, and your only review is negative. I would consider having some type of presence on Glassdoor if you are going to be doing the hiring and you do have at least a couple of employees. You can ask folks, hey, can you just post an honest review of your experience here? I don’t know that this needs too much more commentary or thought, but I do think that’s the problem of these big reviews, especially anonymous reviews. That’s the thing. Yelp, you can effectively be anonymous. You could, over time, can buy accounts on Yelp that have already great reviews. You could set up a new one, leave a bunch of positive reviews, and leave negatives. There are ways you can do that and these things just tend to be really hard if it’s not tied to some identity.
Tracy: As I say, being a Yelp Elite in the early days of Yelp was pretty sweet in the Bay Area. I say as a former Yelp Elite.
Einar: Wait, what’s a Yelp Elite?
Rob: Oh man, you are not in the know.
Tracy: I know right? I was like, how do you not know this? They have this whole program that if you’d left enough reviews—if I recall correctly— you’ll be invited into the special Yelp Elite program and then you will get invitations to restaurant openings and special events. The idea is that they will give a bunch of free food and alcohol and give positive reviews afterward. There was this one summer—quite a while ago for me, like 10 years ago for me—where pretty much every weekend I was drinking for free based on being Yelp Elite.
Einar: What? Oh my God.
Rob: You’re famous. Tracy Osborn, you are @tracymakes on Twitter, and Einar you are @einarvollset. We will link both of those up in the show notes. Einar, thanks so much for joining me again on Startups For The Rest Of Us.
Einar: Thanks for having me.
Rob: And Tracy, thanks for coming on.
Tracy: Happy to be here.
Rob: I really appreciate Tracy and Einar taking the time to record this with me. I hope you enjoyed this episode format. I’ve done just a handful of them over the past several months. If you really enjoy this type of format, please write in questions@startupsfortherestofus.com or hit me up at Twitter @robwalling and let me know what you think. If you think they could be improved or if you just love to hear them more often. I’ve only done them maybe once a quarter, both due to the lack of new stories that are maybe discussion-worthy in our community, but also, they’re a little more effort to set up. But I am willing to do that if I hear resounding yes, yes, yes, this is something that I’d really love to hear. Thanks again for joining me this week and I’ll be in your earbuds again next Tuesday morning.
Tracy: Yeah, happy to be here.
Rob: Einar, you as well.
Einar: It’s very good to be here.
Rob: It’s good to have the band, I was going to say back together, but this is the first time the three of us were appearing on the podcast. I think it’s cool. You both have made multiple appearances over the past 12–15 months, but I haven’t done too many of these. I get a lot of requests to do the three- and four-person news roundtables, but they tend to be pretty hard to plan. The logistics are tough, and then it’s oftentimes hard to find enough topics that really relate to our crowd. We can talk about stuff that is broader news. Jason Calacanis says this with great success on This Week in Startups, but he’s relating it to the world. He’s talking about trade policy and this and that, and I find that it can sometimes be hard to link that back to boots on the ground, MicroConf, Startups for the Rest of Us, TinySeed-type startups. But I do think we have a good docket today. The first topic we’re going to cover is a listener question about the economy. It’s from an anonymous listener. He said, “Early on in the pandemic, you described a broad revenue trend along the lines of, about 20% of companies that you’re invested in or had the financials off their way down, 60% had a minimal difference and 20% are way up.” This question asker says, “Hey, we actually landed in that 60%.” I said that off the cuff one day and then I came back to it a week later. I looked at the numbers and it wound up being closer to 15%, 70%, and 15% for what it’s worth. Give or take, it doesn’t really matter. He says, “So, here is the question. It’s 6–7 months later, what does that picture look like now? I suspected a lot of us in that initial 60% group are starting to feel signs of a real recession. Maybe a few extra customers churn, maybe customers feel renewed but get lower users. The effects aren’t huge, but they’re there. My sample says it’s small but I’m seeing it. It’s not falling revenue but it’s flat where I had expected growth. There’s a lot of reasons why people don’t want to admit this stuff. Revenue failing to hit forecasts is not a good look. Disappointing looks are hard to face. No one wants to consider the implications of that for themselves or for others. If other startups out there are seeing signs of this, it might be helpful for the community to know what to look for and what to do about it. My business is fine and we have a broad customer base, but I’m curious to see what you’re seeing out there in the space.” Einar, you want to take this first?
Einar: Sure. My view is things haven’t changed all that much. I still think the breakdown is roughly what you said. Particularly SaaS businesses that are serving industries—whether that’s travel, schools, or restaurants and things—I still think they’re hurting. I don’t think it’s quite in the same deep freeze as it was back in March–April time frame but certainly, a lot of those companies are still hurting. I don’t think it has expanded necessarily. I do think on the other 15% side, the growth spurts that came for the winning companies have slowed down a little. We saw some companies, in particular—before COVID were growing 30%, 40%, 50% a year—who all of a sudden grew 100% in 3–4 months because they were at the forefront of whatever, work from home, or something that’s COVID-related. We’re starting to see more normalization for these guys’ growth rate. Some of them are back to where they were, 30%–40%. Some of them are coming down off the peaks and perhaps stabilizing at a higher base. Certainly, that’s true (for example) with things related to ecommerce, delivery things, and stuff like that. In the middle, I don’t know, actually. I’m not 100% sure. I feed bad for the question asker. I want to say, yeah, that’s what I’m seeing all over, but that’s really not fully what I’m seeing or at least hearing. People are still tentative. Budgets are harder to get on and approvals are a little harder, but I’m not sure that it’s going to slow down into the fall, from the people I talked to, anyway. It’s peculiar to this small sample size.
Rob: Tracy, you have insight into at least 23 companies across TinySeed batch 1 and 2. What are your thoughts?
Tracy: One thing I was wondering about this question in terms of timing—and I was going to post a question to you, too—was the possibility of things sliding to a recession, but also worrying about that happening while we’re also going into the holidays. What is the drop in growth? Is that something that happens with startups? It’s something that happened with me in my previous startup because we were so…
Rob: Seasonal?
Tracy: Exactly, we were a seasonal startup. I was wondering if people were like, oh, should I be worried about a recession if it’d be worthwhile to go over what you just see go into the holidays—keeping in mind that holidays are in COVID so things are going to be weird—versus if it’s a recession, how that’s affecting your business.
Rob: My thoughts there are obviously if you’re an ecommerce, Black Friday’s coming up. Any type of ecommerce SaaS, software, or whatever is going to be going up into the right over the next month, and then it’ll drop down in Q1. I saw seasonality in all of the companies that I’ve run. It wasn’t seasonality; it’s too strong. I would see (usually) dips in growth, especially if it was SaaS. It wasn’t the revenue drop, but it was the growth that would slightly decelerate. We get fewer signups right around tax day in the US—mid-April—and then around December. I was counting it lucky if December grew at all. If we stayed flat, that was fine, but I really wanted to have a good November. Then, we would come out swinging pretty hard in January. We often launch big things in January.
Tracy: That’s exactly what I was getting at. I’m curious to see how things would happen in January, also depending on US politics, where we are in COVID. This going […] and getting at is, is it too early to say about the recession, being that there are other things going on?
Rob: The uncertainty of COVID, the uncertainty of US elections and holidays coming up, I can see them making people uneasy and not wanting to purchase. The question asker, his business is flattening or not growing as fast. It could be justified by that. I’m invested in between TinySeed and my independent staff. I have 35 investments, and I’m not hearing that there’s slowing down. I’m not seeing plateaus or slowing across the board. There are two questions here. One of them, I may be answering with no, I don’t think everything is flattening right now yet. The second question he’s asking implicitly is, do you think there is a recession on the horizon when we look out 3–6 months? For me, it’s a big I don’t know. I was talking in 2015–2016, there has to be a recession coming. There was in 1989. Well, no. There was one in 1993, there was one in 2000, there was one in 2008. I kept thinking it’s not that it’s every seven or eight right years, but this has been going on, the stock market’s really overpriced. When I sold Drip and had all this cash, I remember just agonizingly investing in the market. I was like, I’m waiting for this thing to be cut in half any day. That really didn’t happen until COVID. It happened in January of 2016. There was a big correction but it came back the next month, so there’s no recession there. The next big hit obviously was when COVID started, but it was so short-lived that I don’t know what’s coming.
Einar: Well, it was short-lived. There’s sort of a binary outcome to start. I don’t know if we’ll be turning to a stock discussion program here, but if you look at the companies that are listed on the stock industries, you see that basically the reason it’s recovered is because of the big tech firms like Amazon, Facebook, Twitter, Zoom, those kinds of things. They’ve done really, really well, versus the Russell 2000 which was the small-cap companies that are listed. They really haven’t recovered. They’re still down 20%–30%. It’s been a story of two different trade industries, which also partly backs up my view of the market. This relates to M&A, too, in the software space. It’s been very strong. If you’re in software or anything semi-positive, like you had tailwinds for at least the last few months now. Today, I think the Dow is down 3%. There’s obviously a lot of uncertainty around the elections. Who knows what’s going to happen with the vaccine and things, but certainly, the last 3–4 months, if anything, I’ve seen tech firms have tailwinds through the last few months at least.
Rob: I think you’re combining two things because you’re talking bear market, bull market, and stock prices, and I’m thinking more recession or not. I’m thinking of SaaS companies just getting started to several […] and revenue, mostly bootstrapped, are they still growing? Even about the retail store here in town, they don’t necessarily care about the stock market. It obviously impacts the broader economy, but when I think about it, if I was running a SaaS company today—whether I was doing $100,000 a year or $5 million a year, and I was, again, bootstrapped or mostly bootstrapped—I would be slightly cautious right now because of how much uncertainty there is. None of us can predict a recession, but there are a lot of things that can go wrong in the next six months. Personally, I’m fairly risk-averse especially when I’m running a company that I don’t want to lay people off. I don’t want things to go to zero. I don’t want to miss payroll or whatever it is. I would be thinking about being a little bit conservative or having a little more of a cash cushion than I would have in the boom times. I mean, you go back a year, you don’t need so much of a cash cushion if you’re going 10%–20% a month. Right now, I would be thinking about, what are my plans B, C, and D if things start to go sideways here? What if growth flatlines for six months, are we good? I’ll be asking myself some what-ifs and figuring out which of these could be company impacting
Einar: Yeah, I think it’s fair. And buy some Bitcoin, obviously.
Rob: Oh my gosh. Tracy, you’re on crypto?
Tracy: My husband is very into crypto, but I am not. I’m sorry, I’m going offhanded here. It’s fun being adjacent to that world but then listening to Einar and his thoughts.
Rob: Einar is just in it for the big score. I definitely know crypto that people who listen to podcasts know that I dollar-cost averaged in. I blend it on these big runs because right now it’s up. I do a little with a dollar-cost averaging out, so I feel good about that. Our next topic is a story from the New York Times, and it is about the Google antitrust suit. The US accuses Google of illegally protecting a monopoly, the Don’t Be Evil moniker that Google had for many years. A lot of us especially small startups who have experienced whether it’s direct competition, whether it’s being stepped on accidentally, whether it’s having AdWords constantly being more expensive, whether it’s having our keywords be not provided, whether it’s having them not send us traffic because they’re doing snippets at the top of the homepage, I definitely think there is a sentiment in early-stage startups that certainly, Google’s doing something that may not be fair or encouraging of the ecosystem. Tracy, what are your thoughts on this antitrust suit and how do you think it impacts the startups in our community?
Tracy: Google just feels like it owns everything. It has its fingers on everything intact, and you can’t avoid them. People are still talking about Superhuman—this other email thing—while everyone’s like, oh, but Gmail’s the best. You’re like, okay, I won’t talk about advertising, Facebook advertising, Reddit advertising when really, Adwords is a thing you have to start out from. You get a new phone, and Google is on your phone. That’s what you said earlier, that’s a lot of these antitrust cases about the phones and everything coming with that bi-standard. I’m a fan of any kind of breaking up at least a little bit because I feel like Google being in all these areas and having its fingers in everything is slowing or preventing some amount of startup innovation in those spaces. What will we see if Google wasn’t number one in everything that we do? In some way of breaking it up and allowing for more innovation from people, where would tech be if Google wasn’t the behemoth that it is right now?
Einar: Ditto. I broadly agree with that. The specific case that the DOJ brought against Google is pretty narrow. If you read it, they’re saying like, okay, it’s antitrust to protect their search monopoly by paying billions of dollars to Apple and whatever to make Google their default search platform. Broadly, I agree. It feels a little bit similar. It’s like Google is walking towards the situation that Microsoft was in years ago back in the 90s. Microsoft was the big bad wolf that squash you, outcompete, buy you, or do whatever. It’s funny that basically, Microsoft got sued by the DOJ for antitrust when they were 22 years old, and Google is actually 22 years old this year. It’s almost like a college graduation thing, like, congratulations, you made it, here is a lawsuit from DOJ. You look at what happened with Microsoft when they did face that sort of thing. That’s overall been good for the startup ecosystem, that stranglehold that they had on tech. There are two ways to look at it. Either the fact that they go sued and things open up some innovation, but then the flipside of that, too, is people have to work around that monopoly to a large degree. That’s why you get WebApps and things when you did in the early 2000s. I don’t know. It’s one of those really big market-moving things, a direct impact on bootstrap software entrepreneurs. It’s more TBD, to be honest with you.
Rob: The big thing that I’ve seen Google do over the past 15 years as I’ve been more involved in the ecosystem, as I’ve started running Adwords, that has been anti-innovation or anti-startup directly, is this slow titration or this decrease in the amount of data that they give to people who are trying to market their businesses. When I started pulling keywords out of Google Analytics, they give Not Provided instead of the actual keyword people were using to search their site. Before Not Provided, I was a small business that was marketing on the internet. I was either doing SEO or was buying AdWords, but it would tell me, hey, they clicked through this keyword and they converted. This keyword converts really well for you. They pulled it out and they gave some […] excuse about it being privacy. First, it was only SSL and then they just rolled it out to everything. What it did is it forced you to buy ads from them. If you buy their ads, they give you the keyword. So how is it so? It never made sense. There was a bunch of uproaring, and Google said we don’t care. Then, they slowly pulled all the data out. Their keyword tool is completely useless now. They said they would never sell search rankings, but if you just search for any term, the top three, four, five positions now are all ads. The organic number one is oftentimes below the fold depending on how many things you have on your screen. You can’t even identify the damn ads. It’s a tiny little box. I had to teach my kids that those were the ads. My mom still—I’ve watched her using the computer—clicks on the top result every time. I’m actually like, oh, you just cost that store money. She’s like, why? I was like, well, you clicked on their ads. She’s like, how is it an ad, it’s a top search. People don’t understand. That’s not what this suit is about. This suit, to be clear, is about the default search engines on these mobile devices. It’s all intertwined. It’s a lot like Tracy said. They are everywhere. Do I believe that they have used monopoly-like powers to just throw their weight around and not care what the market says? I do.
Einar: Oh, yeah. Just ask Mike Taber. The hoops he had to jump through to be able to get to what effectively is the default email client in the world. That’s something that Google can do. All the big boys do it. Twitter is famous for yanking their developer API after the developer helps them become famous and become popular in the first place. I agree with that.
Rob: Our next story is about Dropbox. I’m reading this on businessinsider.com. By the way, we will post all of these stories in the show notes. The headline of this story is, Dropbox will let all employees work from home permanently as it turns its offices into WeWork-like collaborative spaces. Shouldn’t they just say coworking-like collaborative spaces? Why does it have to be WeWork-like? That’s interesting. It’s like saying, Kleenex instead of tissue, or Band-Aid instead of a bandage. Anyway, in essence, Tracy is this just the rest of the startup world? The Silicon Valley startup world is finally catching up to what bootstrappers have been doing for the past 10 years because we didn’t have the money for offices?
Tracy: No kidding. There’s a lot of negative effects from COVID and the effect around office spaces. There are just these norms that once you got to a certain size, you had this office space. What was it? Yahoo! used to let you work from home, then Marissa Mayer became the CEO and she rescinded that because that was the norm. Yahoo! is innovative before but they’re using that as an excuse to bring in […] back in when she was there because she said that everyone works better together. Bootstrappers know that you can’t get just as good work done remotely but all these companies were facing this norm that was pervasive. Finally, COVID is forcing people to make this change. Now, these big companies are waking up to this idea of, hey, you’re not having your employees drive an hour or two from the office. They have simpler lives. Maybe, they’re getting more work done because they’re faced with fewer distractions from being in the office. I’m looking forward to seeing how this plays out in the next year. Hopefully, as COVID gets better and maybe things are opening up again. I’m hoping that like Dropbox, these other co-companies will also have these policies put in place and that employee’s lives, hopefully, will match something a little bit closer to how bootstrappers have learned to work from home or at least have learned to work from home.
Rob: Einar, you live South of the Bay area. I bet you’re seeing lower traffic now that people are working from home. Do you feel like this is going to change the landscape of these big campuses? I know Facebook. My brother and dad worked in the electrical contracting industry in the Bay Area for years. They were part of doing work on the massive Google campus, the massive Facebook campus, the massive CISCO campus, and all of that stuff. Is that done at this point? Do you think most companies are going to wind-up going at least half remote or work from home permanently?
Einar: I don’t know. I’m torn on this whole subject just like the resident extrovert here. I certainly think like some of the traditional views. I saw some venture capitalists on Twitter making a big deal about the fact that they’re no longer going to make it a requirement when they invest or a qualifier that a company has an office before they invest, which I always thought was really stupid. On the other hand, I do think there might be backlash once the vaccine’s in place. I feel cooped up just in my home office, not seeing people just day-to-day. There’s value in interacting directly face-to-face with people, but there will be a fundamental shift in the expectation probably mostly from the employee side. It will probably start with tech companies and then trickle down where maybe they’ll be there a portion of the time. Maybe they work from home 2–3 days a week and then in the office a couple of days a week. What Dropbox is doing is smart because that facilitates that thing, which, in general, is a good thing. We’re already seeing it just in the real estate markets in the Bay Area. The shift where it’s not a good time to own a one-bedroom condo in downtown San Francisco because everyone is just moving out and buying cheaper, bigger places elsewhere. It’s definitely a trend, but do I think it will become everything is remote-first and offices are going the way of the dodo? I don’t really buy that, but I guess we’ll see. In general, commercial real estate is a bit screwed, particularly in California if Prop 15 passes where the tax increases and things. I don’t know what they’re going to do. It follows on from the fall of shopping malls because e-commerce has taken over. They’re just empty malls everywhere. What are they going to do with all of that real estate? The questions are almost the same even if it’s a small trend, like you say 20% of companies or 20% of employees don’t go to offices regularly, that’s a big drop in the occupancy rate of these places. What are we all going to do with this office space that isn’t being used anymore?
Tracy: Couldn’t we convert some to housing?
Einar: That’s what I think. There’s a mall in town where I live. I looked at them and I’m like, why isn’t that converted into an apartment complex at this point? I don’t think that this is going to fill out again in any way, shape, or form. I don’t see why it can’t be a hybrid: partial apartments and partial shopping-restaurant complex. That stuff takes time, I guess.
Rob: For me, I’ve always been a believer that a lot of the companies that have been remote—the larger companies, let’s say a company with 50–500 employees that is remote—tends to be a lot of introverts. They do tend to hire people who work well remotely. We haven’t done an experiment this large, to your point Einar, with companies that didn’t hire specifically for remote workers or have more extroverts, just more of an extroverted workforce. We got the balance right with Drip when we’re in Fresno. There were 10 of us, and there were some people that were fully remote. They were in New York and I went to other states to find the best people; that’s what I had to do. Everyone in Fresno, we came to the office two or three days a week. The third day was optional. I saw Derek, I saw Anna, and I saw my co-workers. When we sold, we moved to Minneapolis, it was three days a week mandatory. It was Monday and Thursday, everyone had the option and most people just work from home. That is such a good arrangement, especially if you have to do any type of maker time. When I’m at home, I would try to block off and not have as many meetings on those days. I like to keep the mornings to myself, and I would have zero interruptions. In the office, I got social time. We did a lot of whiteboarding, but I get interrupted all the time. At a certain point, I said, I’m no longer a maker. It’s just not going to happen in an open office space. I hear you on that. I don’t know if there will be a transformation of these office spaces into living space, if they alter the form into escape rooms and trampoline parks. I see a lot of these warehouse districts. That’s a thing. It will hurt commercial real estate. The rates on a startup office space are higher than the rates you can charge a trampoline park or whatever innovative new entrepreneurial thought does come out of this. There will be a hit but we’ll just have to see how back to normal things get once there is a vaccine and things start to clean up.
Einar: That’s true. Even if you just take your example, if the majority of companies end up adopting what you’re saying, that’s two days out of five. That’s very low-low.
Rob: Yeah, then we’ll have to figure out, we just paid the rent as if we used it because we had it for 30 days a month. We had it 365 days a year, we just didn’t use it all the time. That was the decision we had to make.
Einar: You could end up with a scenario where two companies split it. You have Monday, Tuesday, Friday, or maybe both of them come in. Everybody comes in on Fridays. That’s a big party. You can see those types of situations.
Rob: Yeah. The fact that WeWork has had some major issues and has tanked pretty bad, but can you imagine if there were a more successful, more sustainable model that a lot of these are just turned into shared office space, into more of a WeWork model. I wonder if there becomes an opportunity, there’s that old phrase of like, I want to be the second buyer of everything because the first buyer, the first investor puts a ton of money in, they burn through it, they prove out the model, and then when that goes out of business, I can buy it for pennies on a dollar. Now I have this asset that there’s an opportunity. I wonder if there isn’t going to be that in commercial real estate in terms of office space. Our next topic is an interesting one. Listener, follow me along with this. This isn’t as relevant to someone who’s running an extreme early-stage startup. I know more than one founder who has hit the point where they’re doing (let’s say) $2–$10 million in ARR, they go to try to raise money, and they don’t want to go the venture unicorn track, but they do want to have some liquidity perhaps for themselves or to pump into the company to continue to grow. There’s a couple of things that tie into this. The bottom line is due to the regulations in the US, it’s virtually impossible to do that. It’s not worth it because of the high expense of going public in the US. First is in Canada, there’s the Toronto Stock Exchange and in Australia, there’s (I think) the Australian Stock Exchange; I forgot the name of it. In Toronto, if your company’s market cap is $4 million, you can go public on their exchange. The fees are between $10,000 and $200,000 depending on how much money you raise. It’s actually quite inexpensive. You could imagine a SaaS app, much like you would meet at MicroConf who’s doing $3, $4, $5 million a year going public. The phrase ‘going public’ has such gravitas with us. It’s like only GE, Apple, and Google are public, these are master companies, but I don’t think that should be the case, actually. Einar, you want to walk us through a little bit? We have a couple of topics to touch on here. One, why the hell is it so expensive and hard to go public in the US. And then, the real topic that leads us into is these things called SPACs which are Special Purpose Acquisition Companies and they’ve been in the news quite a bit lately. I’ve heard them on This Week in Startups and there’s a Forbes piece on them. They are suddenly becoming a popular way to go public in the US.
Einar: It is slightly strange. I think most US investors don’t really look abroad. They just think this is the way it’s become. The trend over the last 10–15 years has become that even though this (perhaps) does not have your regulations than they already were, you end up in a scenario where a company like Airbnb is going public after (maybe) 12 years of existence instead of the more typical which is a decade or plus ago with 4, 5, maybe 6 years. It is slightly weird to me that you have to be one of a small number of unicorns in order to go public. As you mentioned, that’s just not the case in other countries. There are dedicated exchanges like the TSX Venture Exchange in Canada. Being Norwegian, I know there’s one called […] in Norway. There’s a couple of ones in Germany. Basically, people understand that if you’re buying stock on this exchange, then yeah, there are some compliance and things, but these are much riskier bets than your GE, Google, Apple or things like that. On a philosophical level, I don’t really understand why that is impossible. Investors can go on the Robinhood app—like I did—and buy a bunch of put options on United thinking that Donald Trump is going to announce some sort of a vaccine before the elections so it’ll jump up. You can lose all your money as I did in a week. Nobody’s stopping you. There’s no accreditation process or doing that. The stock market is, as we in part of seeing through COVID, to a large degree is a good way to lose a lot of money very quickly. But fundamentally, I think one of these things should exist in the US where if you get a certain size, as you say, $5–$10 million in ARR, why not go public? Companies like that go public all the time abroad. It gives access to retail investors who don’t have access to private markets. Fundamentally, the fact that things take longer to go public means that the average investors who don’t have inside access don’t get to participate in the value creation there. I think I actually like SPACs—to circle back to the topic at hand. SPAC’s a sort of a symptom of this problem. SPACs are basically like empty shell companies that people put together and they go public. They list an empty company, the company basically says, we’re going to sell $500 million worth of stock in our company—in the shell company—and then turn around, use that capital to buy or acquire a private company. Effectively, it’s like a backward IPO almost. The company becomes a public company by virtue of being acquired by the shell company. My view is that that sort of a symptom of how complicated and how long it’s taking for all of these companies to go public. I think we’ll start to see more and more of that trend. I’m sort of pro at it. I don’t think there’s any reason why more companies shouldn’t be public so that more investors get access to the value creation that obviously happens there because you get to $10 million, as you say, what’s your option at this point? It’s to sell to private equity, to sell a portion to private equity for some liquidity and things. But are they really giving you the best price? Wouldn’t it be better to just sell 20% of your stock to the public and not have basically one boss who may have the wrong view of how you should grow and what your strategies should be going forward?
Rob: Yeah. I think SPACs are kind of a loophole or a workaround to what I would say an overly regulated, overly complicated system. I certainly think there need to be investor protections. Yes, most of the laws that are governing all of these were written in 1935. They haven’t really been updated. There was the jobs act that was a little bit for crowdfunding, but really, there are still a lot of problems with what’s going on today. Tracy, you’ve witnessed it first hand as we’ve been raising funds for TinySeed Fund II. Einar came back to us because he was doing research and he said, if you raise a venture fund, which is what TinySeed’s raising and you’re raising more than $10 million, the highest number of investors you can have in that fund, these are accredited investors who either have a million dollars or more in liquid net worth, not including their primary house or they have an income of $200,000 a year for the past two years or $300,000 if they are married. To put this, the definition of a sophisticated investor in the United States, even then, you can only have 99 of them in your fund. If you want to raise, for example, a $40 million fund, you need people to give you your minimum investment to be $400,000 per as average out to that, which is kind of crazy. Because if you could have a thousand investors, then you can drop your minimum way down and you could make it more accessible to so many more people. I think given our love of what we are doing and our belief in this space, that we would prefer for more people to be able to participate. But I’m curious, had you heard of this 99 investor problem before now and any other thoughts on it?
Tracy: This issue really goes back to me as someone who isn’t an investor, has always dreamed about becoming an investor, kind of a baby investor. Coming into TinySeed, I had no idea about what went into raising a fund and being a part of a fund. TinySeed’s thesis, which you put on our website—working here, I totally agree with it—we’re talking about TinySeed being an index fund into B2B SaaS. When you’re talking to people who can be a credit investor, that those require you have before but maybe just barely meet those requirements, a lot of people are very into the mission we’re doing, a lot of people don’t have $400,000, but they’re like, hey, this sounds like a winning bet to me. I love to put it in 5000. It sucks to be like, no, we can’t. We can only talk to the people who already have enough wealth that they can just blow this massive amount of money into TinySeed. It creates this problem between wealth equality in a way that people who are coming from disadvantaged backgrounds have a hard time getting to that level of wealth to be able to throw around that amount of money. When we have something like TinySeed—again, I totally believe in what we’re doing, think they were going to be a success—I want to help other investors, especially from disadvantaged backgrounds, also be a success with us and we have to constantly tell them no. It just drives me absolutely at the wall. The fact that the 99 investor problem exists—Brad Feld wrote a blog post about this if you Google for it—it’s frustrating. And because in 2018, President Trump signed (I think) the startup act or whatever, that was hoping to solve this problem between 99 investors being allowed to invest to be in a fund by opening it up to 250, if I recall. But that only applies to funds that raise less than $10 million, which is ridiculous, because the funds are raising more than $10 million and need to have more number of investors who are able to invest in it. I feel like it’s a huge issue. It leads to the restriction of wealth growth to these already wealthy people. It’s like I can go to a casino, I can spend $5000 in a casino, and no one would bat an eye. But I can’t take $5000 and try to invest it in some larger fund which, because they’re kind of indexing, arguably might have more chance to succeed that’s not allowed for me because those funds are restricted to only large investors. It’s just bananas.
Einar: I obviously agree. I talk to investors all the time and I tell them, I’m sorry, our minimums are minimums. People get frustrated and they’re like, you know, I want to put $50,000 into this. Often, they’re successful operators. They’re people who maybe bootstrap to SaaS business, got it to a million or two, sold it, and now they want to put some money into the area that they understand. In part to support the community and in part to obviously make a return. The crazy thing is, it’s already even worse than that because technically speaking, there are two definitions of investors. There’s more, but the main ones are the accredited, which is what you’re saying. Really, then you’re a pretty wealthy person if you qualify as an accredited investor. But there’s a higher threshold called a qualified purchaser. Basically, what a qualified purchaser is is somebody who has at least $5 million in investments. That’s obviously wealthier than someone who is “just an accredited investor.” But the funny thing is, that you can actually take off the 1999 qualified purchasers. What that means is, our minimums, and any fund’s minimums can be lower for the wealthier investor. Which doesn’t make any sense. I can take $5000 from you if you want to, but only if you’re worth at least $5 million. If you are “only worth $2 or $3 million,” well, I’m sorry, but then I have to take $400,000 or whatever the minimum for the fund size is. That doesn’t seem to make any sense to me. I don’t know that I’ve ever read a good reason why the limit is 99. I don’t understand why it should be like a thousand. You don’t want something that turns into a scam, then gets a million investors caught up in it, but 99 just seems really arbitrary.
Rob: If it was a million then it’d be a public company. If you had that many […] public. But you’re right, there’s a big difference between 99 and a million. We’ll see what happens. I’m just throwing my hands up and being like, somebody needs to figure this out because I do believe this is hurting innovation. Much like the high cost of healthcare in the United States, I think the regulation around going public and the regulation around 99 investor limits on funds, those three things are the things that I have experienced first hand over the past year or two, that are seriously impacting the startups that I’m working with. Not only with TinySeed, but just all around MicroConf and the people listening to Startups For The Rest Of Us. Hopefully, we can do something about it and I would be remiss if I did not recommend people go check out tinyseed.com/thesis. If you click through there, you can of course send Einar an email. You fill out a form and he gets an email, and you could chat with him to hear about the TinySeed thesis and to hear more about what we’re up to and how we’re raising that fund. Our last story of the day is from Reddit and it’s a warning about Glassdoor. The person says, “For the past few years, I’ve often defended Glassdoor as a useful resource, as part of any job seeker’s overall job-seeking toolkit. About a year-and-a-half ago, I interviewed with the company that had horrendous reviews.” This is a thousand […] summarized from here. In essence, there were a lot of negative reviews, the person took the job anyway, the job was not good, and the environment was toxic according to this poster. They wind up going back to Glassdoor and posting a negative review, that then not only got removed but every one of this person’s reviews on Glassdoor was removed. They implied at the end of their post that they’ve heard that Glassdoor has supposedly done a minor pivot into brand management so that perhaps it’s becoming less reliable than it’s trying to get rid of negative reviews or something to that effect. The question I have is maybe two-fold and we’ll start with you, Tracy. Glassdoor has tended to be a bit of a mixed bag, but I’ve used Glassdoor quite a bit for salary recommendations which I find to be pretty reliable. I also used it back when I looked at lead pages, Glassdoor as an example when we were talking about being acquired by them. There have been companies where I have tried to research whether I think they have a positive or a negative reputation with their employees. I have always wondered, much like Yelp and much like Amazon reviews, these things do get gamed eventually. I’ve always had in the back of my mind, I wonder how reliable these actually are. Do you have much experience with Glassdoor and what are your thoughts on this whole topic of can this be a game, do we think that as something gets big, eventually it just does lose its value because they can’t control the potential review spam?
Tracy: It’s just funny to me because I’ve never used Glassdoor other than for salary information like you mentioned. A previous company I worked for had Glassdoor reviews and they were terrible. It was the funniest thing to me. I believe one of the large reasons why they completely renamed and rebranded the company was because their Glassdoor reviews were so terrible and they needed to have some way to wipe the slate clean. This was about seven or so years ago. There are probably a lot more systems to game it now. But back then, you just had to wipe the slate clean in order to get rid of those past reviews. I have checked them recently and they have better reviews before. I assume that they made some management changes in addition to rebranding the company. It’s definitely been games in the past in a very complicated matter like that. I absolutely think it’s being games now. I read that article, that Reddit post they are mentioning. It’s just like Yelp. All these companies are going to be very concerned about their reviews because it’s going to vastly affect the quality of the employees they get. Savvy employees are going to leave bad reviews and they’re going to stay away. Now, these companies are going to be doing whatever they can to either with Glassdoor or otherwise to scrub those reviews just like Yelp. I think what’s going to happen, just like Yelp, I think people are going to use it less now that these things are coming more in the forefront. But I’m curious to hear what you two say about this.
Rob: I’m wondering if this does open up the door, the opportunity for a new Glassdoor competitor to come in and have a better algorithm from the start or some other way of validating this stuff that then becomes reliable for a few years and then the same thing happens. Einar, do you have thoughts or experiences with Glassdoor?
Einar: I don’t have much experience specifically with Glassdoor. But I do think in general, anonymous reviews of things, I think it’s prone to gaming in general. I think you’re right. I think there’s probably a way to make Glassdoor not so easily gameable, but it doesn’t surprise me at all that companies will want to try to do it. Like I said, one of the hardest things—recession talk aside—is to get people to want to work for you, to get quality people to do, and if you have a horrendous review on Glassdoor that says this is the worst place in the world to work, that’s going to be a problem. I think in general. As I said, it’s a little bit like Yelp reviews. Do you really know or is it somebody who has a real aversion to creamer in their coffee and this particular way that this café does it and decides to make it their mission to take this café down? That’s hard to know.
Rob: Yeah. Obviously, if you listen to this, you’re probably at a pretty early stage. Maybe 0 employees, maybe 10 or 20 employees, I do think at least for now that people will go to Glassdoor. If you have no profile, that’s probably fine, because you just say, we’re so early that we don’t have one. The danger is, if you don’t have a profile, someone leaves a negative review, and your only review is negative. I would consider having some type of presence on Glassdoor if you are going to be doing the hiring and you do have at least a couple of employees. You can ask folks, hey, can you just post an honest review of your experience here? I don’t know that this needs too much more commentary or thought, but I do think that’s the problem of these big reviews, especially anonymous reviews. That’s the thing. Yelp, you can effectively be anonymous. You could, over time, can buy accounts on Yelp that have already great reviews. You could set up a new one, leave a bunch of positive reviews, and leave negatives. There are ways you can do that and these things just tend to be really hard if it’s not tied to some identity.
Tracy: As I say, being a Yelp Elite in the early days of Yelp was pretty sweet in the Bay Area. I say as a former Yelp Elite.
Einar: Wait, what’s a Yelp Elite?
Rob: Oh man, you are not in the know.
Tracy: I know right? I was like, how do you not know this? They have this whole program that if you’d left enough reviews—if I recall correctly— you’ll be invited into the special Yelp Elite program and then you will get invitations to restaurant openings and special events. The idea is that they will give a bunch of free food and alcohol and give positive reviews afterward. There was this one summer—quite a while ago for me, like 10 years ago for me—where pretty much every weekend I was drinking for free based on being Yelp Elite.
Einar: What? Oh my God.
Rob: You’re famous. Tracy Osborn, you are @tracymakes on Twitter, and Einar you are @einarvollset. We will link both of those up in the show notes. Einar, thanks so much for joining me again on Startups For The Rest Of Us.
Einar: Thanks for having me.
Rob: And Tracy, thanks for coming on.
Tracy: Happy to be here.
Rob: I really appreciate Tracy and Einar taking the time to record this with me. I hope you enjoyed this episode format. I’ve done just a handful of them over the past several months. If you really enjoy this type of format, please write in questions@startupsfortherestofus.com or hit me up at Twitter @robwalling and let me know what you think. If you think they could be improved or if you just love to hear them more often. I’ve only done them maybe once a quarter, both due to the lack of new stories that are maybe discussion-worthy in our community, but also, they’re a little more effort to set up. But I am willing to do that if I hear resounding yes, yes, yes, this is something that I’d really love to hear. Thanks again for joining me this week and I’ll be in your earbuds again next Tuesday morning.
Episode 520 | Why a Million Dollar Agency Quit It All and Moved to SaaS
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In this episode, Rob talks with the founder of SegMetrics, Keith Perhac. SegMetrics is a SaaS product that helps users get clarity on where their leads come from, how they act, and how much their marketing is worth.
We dive into the difference between SegMetrics and other options for attributing sales and revenue to traffic channels.
We also go through Keith’s background and learn about why he shut down his million-dollar marketing agency to double down on his SaaS.
The topics we cover
[04:28] Where does SegMetrics fit within the analytics and attribute market?
[09:35] Why build a SaaS when you are running a 7 figure agency
[12:56] Dealing with a growth plateau
[21:28] Shifting focus to work on SegMetrics full-time
[28:05] Frugality as a bootstrapper (and how it can backfire)
Links from the show
- SegMetrics | Twitter
- SegMetrics | Website
- Keith Perhac | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify | Stitcher
Rob: Welcome to this week’s episode of Startups For The Rest Of Us. This is episode 520 in which I have a lovely conversation with Keith Perhac, the founder of SegMetrics. SegMetrics allows you to get 100% clarity on where your leads come from, how they act, and how much your marketing is really worth. We dive into exactly the difference between SegMetrics and other options for attributing sales and revenue to traffic channels, advertising channels, and all that.
We’ll go through Keith’s background. You may have heard of him. He’s done at least one MicroConf attendee talk. He’s done a MicoConf mainstage talk. He used to host a podcast with Pat. Keith and I cover some really interesting ground today as he talks about why he shut down his million dollar marketing agency to build and double down on his SaaS.
Before we dive into that, I wanted to ask you a favor. If you’ve been listening to the TinySeed Tales episodes that are coming out on Thursday mornings, you have heard through episode seven that came out last week, there are two episodes left. Obviously, this Thursday and next Thursday. I’m curious to get your feedback on season two and frankly, just the whole concept of TinySeed Tales. Feel free to email me directly at questions@startupsfortherestofus.com. You can DM me on Twitter or you can mention me at @robwalling on Twitter.
Given the amount of time and money that they cost to produce, I’m curious to hear if you like the storytelling approach. Obviously, it’s a more produced form than really exists in our space. I enjoy doing them but I also want to make sure that they’re providing some type of value to you; whether it’s entertainment, motivation, inspiration, tactics—just anything that you’re getting out of it. I would appreciate hearing from you. Drop me a line and let me know what you think.
With that, let’s dive right into our conversation. Keith Perhac, thank you so much for joining me on the show today.
Keith: Thanks so much for having me, Rob.
Rob: Today, we’re here to talk about why a multi-million dollar agency owner decided to quit it all and move to SaaS. It’s a great topic.
Keith: It is. It sounds a lot more impressive when you say it.
Rob: Why in the world would you do that, sir? Now, we’re going to dig into that today. Just so folks have some context, you’re a software developer turned marketer—the dangerous combination. I love that combination whether it’s a marketer who learns how to code or a developer who learns how to market.
Keith: It’s like a superpower.
Rob: It really, really is. I don’t think people understand that enough. A lot of us developers, you do it for five years, you do it for seven years. You become senior and you’re like, man, I can do a lot of things. Then, you start over with marketing and it’s a grind. You don’t know any of it, you think it’s fluff. You get three, four, or five years into that and you pile those two on, it’s ridiculous. It’s like an epic, highlevel, multiclass in Dungeons and Dragons.
Keith: Yeah. Just to be able to understand how the internet and all that technology works makes you such a better marketer. People come to us and they’re like, why aren’t these things tracking right? Because you have no idea of how the internet works, why the scripts aren’t firing, and how URLs even work.
Once you understand that, it’s a superpower to get everything. That’s not even touching the automation you can do, it’s crazy.
Rob: Yeah. You were running a seven figure marketing agency. It was called Develop Your Marketing, focused on conversion rate optimization and building out funnels. You had marquee clients, big name clients folks I’ve likely heard of like Ramit Sethi and Eben Pagan.
You decided to build a SaaS on the side. I think you were using the same resources. You were kind of using the agency team to start building that out. That SaaS is called SegMetrics, segmetrics.io. I’m going to read a little bit about it so folks have a context of what you build, then we’re going to go back and kind of talk through your decision to build it, the highs and lows, the launching—just the whole story so folks can both be inspired by it and also feel the agony and the pain of what you felt in the early days. As well as takeaway some actionable stuff. Obviously, your story as a marketer and a developer, I think there’s going to be a lot of folks that can takeaway.
SegMetrics, your h1 is, “Get clarity on your true lead value in every step of the way.” The subtitle there is, “Get 100% clarity on where your leads come from, how they act, and how much your marketing is really worth. Get a handle on the Key Performance Indicators that matter most for your marketing funnels. Built by marketers, for marketers.”
When I think of analytics or attribution, I think of, okay, I have Google Analytics as this anonymous analytics and aggregated. I have a Mixpanel. There’s obviously those types of competitors for individual funnels and people walking through. Of course, I have Facebook Pixels, Google Pixels, and other things for conversions and dollar amounts. I think Mixpanel does that too. Where does SegMetrics fit into that mix?
Keith: The idea is kind of similar to Mixpanel in a way, which is we want to be able to see everything that anyone does in a customer journey. From what ad they landed on to how many times they viewed a page, to if they attended a webinar, to be able to understand who are the most valuable people who are going through your marketing funnel.
The problem with Mixpanel is that it has no native integration. It has no idea of revenue out of the box. It has a garbage in and garbage out problem. Unless you were really diligent about what data you’re sending into Mixpanel, you’re not going to get anything valuable out of it.
What SegMetrics does is we take that idea of like, okay, we want to see every event in an entire customer journey. Marketers are never going to be able to hook this up. What we need to do is integrate directly with all these tools to pull the data out of Google Analytics, out of Google Ads, Facebook Ads, your ESP, your CRM, your Stripe, your payment gateways—everything—and create an individual persona that we can then say this is this person from all this different sources brought together. This is their full customer journey.
Then, what we’re able to do is say, all right, we know that Facebook Ads, our lead value is $50 for each lead we bring in from Facebook. Within that, do we have actions that make people worth more money? Worth less money? Are there certain demographics that can make people more valuable? Is this idea of finding these segments of actions, or demographics, or people that are more valuable so you can then go after them more, be able to market to them better, and understand your audience better.
Rob: Yeah. That makes a lot of sense. It was certainly an issue that I’ve had marketing SaaS, as we were doing ad spend or even getting organic traffic of I had this aggregate numbers of, hey, this is what our churn is, for example. I couldn’t slice it based on demographics or oftentimes, even based on source unless I really have to finagle some stuff.
Keith: That’s why we built it. As a conversion rate optimization agency, that’s what we’re doing. We exported all of this data from all these tools, created a bunch of pivot tables. Five hours later, we had information.
Rob: Yeah. Inside SegMetrics, you can slice and dice it. You could look at churn. You could look at lifetime value based on all this stuff, right?
Keith: Exactly.
Rob: Okay, for me that paints a crystal clear picture. I think most SaaS founders who’ve gotten this far, who are doing $5000 or $10,000 a month or more, are trying to attribute stuff, know the limitations of having to build it custom.
We may have already answered my first question, then. My first question is why build a SaaS company if you’re running a seven figure agency? It’s obvious that over and over and over, you probably have to cobble this together with duct tape and baling wire.
Keith: Yeah. Essentially, we were working with an analytics agency—a friend—who did a lot of our analytics. We had a lot of our analytics done inhouse. We just spend so much time on it. We were spending probably 20%, 30%, of our week just pulling the numbers. That doesn’t even mean the analysis of what they’re doing but just pulling these numbers.
Okay, we have this webinar. What is the lead value of someone who attended the webinar? We pull all that data from whatever system we have then we pull it from all the tags. Then, we pull the revenue. Then, we match them together. Awesome. Then, we write up the report, the PDF, and everything. We take it to the client and they’re like, what about the people who came from organic versus paid? What’s that breakdown look like? I’m like, give us five more hours. We got to go through that whole thing all over again with these new things.
The analytics guy we were talking to and the guy on my team, we were talking about this, and he’s like, it’s just a database. It’s just a spreadsheet. Why can we not just slurp this data in and do this automatically? That’s where it kind of starts. Okay, could we do this? Could we scratch our own itch? Yeah, that’s where it kind of started from.
Rob: Today, you are a team of 10. As you said offline, “Growing very quickly.” Of course, I have your revenue graph here. You’re in batch two of TinySeed, I have access to your numbers. I will confirm that. Doing very well. In fact, your growth has accelerated. It really looks like at April, May, it starts kicking up which coincidentally—
Keith: I wonder what happened in April and May of this year? I have no idea.
Rob: I have no idea. Don’t think batch two started. We’ll get into that later on the interview. I want to do something chronological. You started working on this five years ago, back in 2015. You told me that you built it in two weeks, 2-3 weeks. That you had a customer the first week of launch. That sounds amazing. That is crazy, crazy fast—to build this whole that fast. Second, to get your first customer the first week of launch. Both of those things, how did those happen?
Keith: This is actually the second SaaS I built. The first one was Summit Evergreen which was a membership site platform for marketers. We had made some mistakes that time. We thought we knew what the customers wanted based on the consulting we have done. We built a very large, very complicated app that had a lot of features that turned out no one actually needed. It took us many months to get to market. Once we got to market, it was slow to get people in. It was very difficult.
With this, we built it to scratch our own itch. At the same time, we’re like, this is something that everyone needs. We’re not going to make the same mistake. What we did was we did a very hands-on, iterative process with our customers. We picked two or three customers—clients—that we were working with. We said, hey, we’re building this thing. Here’s the numbers that were looking to get this value. They would respond. We would say, awesome.
We did a raw dump of their data. We plugged in the engine. There’s no UI. There’s nothing at this point. There’s just me doing some math in a PHP file on the backend based off of the CSV. We get that in and we spit that out. We show it to the clients and we say, hey, for this webinar you just ran last week, this is the lead value. They’re like, oh my god, this is amazing. We’re like, okay, this probably has space.
Then, the team had a little bit of downtime. I think this was early February or late January. Right after a big launch. We knew we had two weeks of almost no client work. We decided, let’s put a challenge to ourselves. Let’s get the team together and we’re going to work on this fulltime for two weeks. We’re not going to do any client work because we don’t have much scheduled. We’re going to see how much of this we can build.
In two weeks, we pretty much had version one done. The engine was already built but the UI, the signup, everything around it, the creation of the reports, the spitting out the reports, the graphs, the everything we built around two weeks. Finally, we launched and it was the product of the day when we launched. Super excited about that.
Then, I found out that there was a space in our Stripe public key when I copy-pasted it into the site, no one was able to purchase. That was rough. It didn’t deter us. I think within a month, we were up to $1000 MRR.
Rob: Wow, that’s great. A lot of learnings from that. I think people think of an MVP as a limited version of a product. You really tripled down on that definition.
Keith: It was a text file. I actually have screenshots of me and Slack. Or not Slack, it was Skype. I just had a text file with six lines. I copy-pasted that. Again, is this valuable? I’m like, yes. That was it.
Rob: Yeah. I love that approach. I often talk about, in my first book, human automation of having VAs just do something on the backends and spit out a report. That’s really, in essence, kind of what you did there.
First customer in the first week of launch, you obviously solve a problem. 1000 MRR in the first month; were you getting those leads from clients, or were you actually doing marketing?
Keith: I don’t remember, to be honest. I know we had two clients that had decided to sign up as customers. A number of our clients we kept as just kind of free users. They weren’t interested in the numbers, but we needed it for our work so we did it internally. Then, the rest were people who found us either through Product Hunt or promotions that we did, tweets. That was five years ago. I don’t really remember who they were and where they came from.
Rob: Right. You mentioned to me as we were talking before the interview that you were at about $1000 MRR after the first six months. Is that right? Did growth plateau that much?
Keith: Yes. We didn’t hit $2000 until August of 2016.
Rob: That was more than a year later, because this was early 2015. What happened then? You basically rocketed to $1000 MRR, you solved the problem that people are obviously in a dire pain point. You flatlined, in essence, for a year. What happened there?
Keith: More than a year. More than a year, Rob.
Rob: You remember every minute of that. 15 months.
Keith: What happened was I had a day job. Not a day job like I was working for someone else, but we had the agency. The agency is pulling, like you said, $1 million+ a year. It’s really hard to take the team off of client work and put them on something that’s making $1000. We didn’t have any customers or any clients that paid us $1000, just $1000. That was inconceivable. I think our lowest contract was $10,000 a month.
It was very difficult for us to put the time into it. I think we language there—I’m looking at the graph—until mid-2018. Wow, you can actually see the spike. Mid-2018, I had decided that we were going to focus on SegMetrics. We always said, hey, we’re always the bride’s maid, never the bride. We’re helping our clients run these million dollar launches—multi-million dollar launches. We’re making good money but we want something that we control in our product, in our stuff. We had always thought this. We had SegMetrics there but we haven’t put any love and any energy into it.
That summer, I remember, I spent some time. We rewrote the UI. I said, we’re going to focus on this. Over the next six months, we’re going to transition out of consulting work, out of the agency work, and we’re going to start moving towards SegMetrics and something that we own.
I know it’s going to be slow because we make a lot from the agency and we need to wind that down slowly. That’s our goal. I was just so tired. I think the team was just tired of having this great resource that no one was using. We didn’t spend the time to make it worth it, to put it out there.
Rob: I remember having that same issue before I went full time in products. I was consulting. I had, basically, a micro-agency where it was either me or a few contractors that I markedup and billed out. It was software development. I remember billling $125 an hour, $150 an hour, somewhere in that range, for every hour. I was booked more than full time. 40+ hours a week I could work. I had these products on the side that were doing exactly that. I had a beach towel website that was doing $1000 a month. Net profit was $150 a month. I had DotNetInvoice which was doing a couple of grand a month, most of that profit.
When you compare those numbers, it’s like, I can make a couple grand in two days of work. It was such a struggle. I heard people call it an addiction. The cash agency work or consulting is this cash addiction. It’s amazing when you want to get to full time income or higher quickly but it’s really hard to move away from. As you said, the focus is constantly towards your high value, instant cash infusion, which of course, is working for clients.
It sounds like you got tired of it. You got fed up with it and you wanted to double down on something that you have built. You fired your whole team in order to do this in late December 2018. That must have been brutal.
Keith: It was rough. It was honestly rough. It wasn’t, hey, I decided to work on SegMetrics and I’m letting everyone go. The original plan was to bring everyone over and we’re going to slowly shift over. The team’s going to stay. There were a number of issues with that.
One of them was that same mental model that the company has of, hey, I can do work for clients and make a lot of money. Or, I can spend time and make no money with the SaaS, was also there with the employees, with my team. We actually had a number of conversations over six months. Essentially, what it came down to is, it was too hard of a mental shift to go from the client is asking something right now. I could spend an hour on that and the company makes X hundred dollars. Or, I can spend six hours working on SegMetrics and the company makes… There’s not a one-to-one translation.
At this point, I think we had done the agency for six years. Eight years, maybe? That was the challenge. We have an hour for dollar, time for money exchange with our clients right now. We do not have that for SegMetrics. We have time for literally nothing exchange. It was very hard for not only myself, but my team to prioritize that.
There are also other issues like when you only have less than 100 customers, you don’t need an account manager. Where do we take the account manager? We kept trying to find roles that didn’t fit for people. It was just very difficult. What I ended up doing at the end of 2018 was saying, hey, guys. You guys are incharge of SegMetrics. You guys work on SegMetrics. I’m going to handle all the client stuff so it gets it all of your plate.
The mistake I made was thinking that they understood SegMetrics as well as I do. I’ve been living it for a year at that point, mentally. Trying to think of, what are we doing next? What are we doing next? It was a mistake on my part. It was just a shift that couldn’t happen.
What happened in January, I said, guys, we can’t do this anymore. I helped find them new work, introduce them to clients. Honestly, it was heartbreaking. I worked with these guys for 6-7 years. It’s really rough. The good side of it—kind of the windside of it—is that because SegMetrics has been growing and because there’s very little of the agency side left, I’ve actually brought them back on in the last few months. I’ve brought the team back together and they’re now working in roles that I think run to their strength instead of the things I was trying to force them into, which is really wonderful. I love working with them and I’m glad that they’re back on the team.
Rob: That’s such a cool ending to that story. When you’re in the midst of that, it probably feels devastating. Yet, to circle back two years later and be like, hey, we have a product now that can afford all of us, that makes the salaries. It’s an incredible story. That’s cool.
As you’ve contacted people, I’m assuming you’re bringing them on one at a time, you email them like, hey, want to come back and work on SegMetrics? Are they stoked? Are they over the moon to do it?
Keith: I don’t know. Yes, they were. I was always very nervous about the whole thing because I let them go. I felt like I had failed them, in some way. It was very nerve-racking for me to reachout, to talk about that, and bring them back on. We had talked in the interim. It’s not like I had cut them out of my life completely. I hope there’s no ill will. I enjoy having them back on. Mentally and emotionally, it was a very rough time, I guess.
Rob: I imagine, it seems to me, if I were in your shoes, it would almost be a mix. You have to let these folks go, even working with them. At the same time, once that’s done, you were then full time on SegMetrics—focused, right? By January of 2019, this was a month or two later, you were, essentially, for the first time since you launched it, you’re all in on it. That had to feel good.
Keith: It felt good. It felt very good. It did come with some challenges, though. When there’s other people around, there’s blame to go around. I see this a lot with my family as well. It’s like, it’s noisy here, I can’t concentrate. Or, the kids kept me up last night. I can’t get my work done.
Then, when it’s just you, all those excuses go out the window. You’re like, crap. The reason I’m not being productive, the reason I’m not focusing on what I should be doing is not some external force on me. It’s because I’m an […]. I need to get in gear, get my mental state insync so that I can do my work, and focus on the things that are important.
Rob: Yeah, that’s such an interesting thing. You mentioned to me offline that your family actually left for six weeks and you weren’t able to go with them. They went to Japan, where you guys used to live. You were left alone at the house. Probably, your inner monologue is, finally, all the interruptions are going to stop. It’s going to be so quiet. I’m going to get so much done. That’s not what happened.
Keith: No. The first two days were great. After that, I just had to start wrestling with my own existence at that point. I’m like, why am I not being productive? I remember back when I was younger, I could pull those 14 hour days, it was great and I felt energized by that. Now, I’m almost 40, I’m going to be 40 this year. I don’t have that same energy. There’s a lot of mental stuff that went around that. I had to understand what are the things that make me productive, what are the things that don’t make me productive, and how can I get rid of the things that don’t make me productive.
Rob: Yeah. There’s so much about learning your own psychology, managing that, and learning yourself. Same thing for me, when I was in my 20s, I could do 12 hours a day plus, sometimes, 14 hours a day. That was the point where Sherry went to Africa for a month, I believe. During that time, I would come home from the day job and then I would kick on a season of Friends. I make dinner, just sit on the couch, and code. I was coding side projects. This was 18 years ago or something.
Man, I got so much done. I would basically work from 5-6 at night until 1 or 2 in the morning. I’d get up the next day and go to the day job. It was kind of exhilarating because I was building my own thing. Within a month, she came back and I had launched a product. I believe that was FeedChat, it was a really early one that I did that crashed and burned.
During that time, she came back and I started talking about Ross and Rachel as if they were my friends. I was like, oh, yeah, Ross was saying… She was like, you know they’re not real, right? You know that they’re not real people, right? That’s always been a funny joke.
It’s learning about your own psychology. Obviously, in my 30s and now early 40s, you have to know more about yourself, I think. Atleast, I have to learn more about myself, my ability to make myself focused, and make myself get stuff done. It sounds like you’ve gone through the same thing.
At the beginning of 2020, eight or nine months ago, you hired a project manager to manage you—to basically bust your chops. Tell me about that. It’s pretty smart. I know some people get executive coaches or business coaches who they meet once a week or twice a month or something. You hired someone who’s more in the business and almost they’re like driving tasks. They’re keeping you accountable.
Keith: Yeah. Even before I really had the team back, we were creating quarterly goals. We were creating, okay, this is what we’re going to be working on this month. It gave me two things. One, it kept me on task. If I went off rails too many times, sure, you’ve got something come up with whatever, she kept me on. Like, hey, if you don’t start on this stuff, we’re not going to finish it by the end of the month. We’re not going to finish it by the end of the quarter. Usually, the things that you said were important.
That was one thing that was highly valuable to me because I default the coding. I don’t default to launching or to marketing or to any of that. I default to sitting and building out new features because that’s what I enjoy doing. That’s not going to move the product. She was very good at keeping me on what needed to be done for the business.
The second part of that, which I thought was just as valuable, was that at the end of the month or at the end of the quarter, she’s like, here’s all the things you got done. It was mind blowing. I’m one of those people who no matter how much I get done, it never shows that I got anything done. I feel like I’m constantly busy but I’m not getting enough done in the time. To have her come and we go back over the last month or the last quarter and say, we got 80% of the key tasks you said that you’re going to get done. You got all these other small things that came up during the month that, maybe, didn’t get done. The key things you said needed to get done this month, got done. That was amazing. It was empowering to me.
Rob: Yeah. The accountability alone—to end that, it’s knowing yourself, right? Some folks I know, they can go to the gym, they want to do it on their own, or they get equipment at home and want to workout in their own garage and prefer not to be in the social setting. Other folks want a trainer so that they have to show up this many days a week and get their chops busted. I think that’s kind of a cool hack. Again, I’ve heard other folks hiring CEOs, coaches, or executive coaches but this was a little different take on that. I thought it was interesting.
Keith: It was actually Ramit Sethi who hired someone off Craigslist to slap him each time that he looked at Reddit or anything like that.
Rob: Oh, geez.
Keith: He did a whole blogpost about this. Essentially, he hired someone to sit next to him. Everytime he goofed off, looked at Facebook or something, she just slapped him.
Rob: That’s like a reality TV stunt.
Keith: That’s the value that having my project manager gives me. She’s not physically slapping me but that’s the value that I’m getting out of it. Like, hey, stay on task. You’ve got stuff to do.
Rob: Right. It sounds like you’ve kind of hacked your own psychology a bit with this project manager and fixed that weakness, I guess, for now. Switching gears a little bit, you talked about—I saw it in the TinySeed Slack—that one of the low points of your year was earlier this year. It was a technical snafoo with the database. I’m going to make you relive this. We’ve all been there, you’ve just got to tell the story, man. It’s going to be painful. Do it once. We’ll get it on tape.
Keith: Databases, they are my kryptonite, I guess. What happened was that there’s something in Maestro 57 or whatever you’re using that made the database fillup in about an hour. We went from 30% full to completely full in an hour. Of course, if it’s full, it’s not going to write new data. We’re f-up there. Trying to figure this out, freaking out, and there’s no way to compact it down. I think it’s like a 12-year bug in mySQL.
I finally gave up and said, okay, we’re just going to export the database, create a brand new one, and do it over. We did it. All right, we’re safe. Cool. Two weeks later, the exact same thing happened. This has taken a week of my life at this point. Just to migrate this thing, do it, and make sure everything’s done in this whole thing. Then, we have to do it again. I finally say, I can’t do this anymore.
We moved to a managed hosted solution through DigitalOcean who’s our providers. They have a hosted database setup. We migrate everything over there. Finally, we’re good. All the tests were perfect.
I go to sleep. I wake up to my phone buzzing again. I’m like, oh my god, what now? Apparently, there are some setting differences between how they have it setup and normal mySQL that was causing a bunch of imports to fail. All of our tests ran. I think it was four weeks or maybe six weeks of just screaming constantly about this database issue, throughput issues, and speed issues. It’s just miserable. Just absolutely miserable.
I don’t know what people are supposed to take out of this because it was just painful. The thing that I took out of this was that the reason I was running the local database in the first place, not to manage one, is because it was a fourth of the cost. I was like, I can do this better, I can have it customized, and I’m going to be paying a lot less. That was great until the database exploded. Then, exploded again. I lost 4-6 weeks of productivity because I didn’t want to pay, I don’t know how much. Maybe $100, $300, $200, extra per month for managed solutions.
Rob: Man, as a bootstrap, I would have done the same thing. It can be obvious, in retrospect, like, oh, I just paid a few hundred dollars because it made sense. There’s so many decisions you have to make as you’re growing. You can’t always do the Mercedes.
Keith: You can’t throw money at all. There’s just too many.
Rob: That was a big difference once we sold Drip to Leadpages. You could just throw money at it. They had raised $38 million in venture. I remember having strategic conversations with the senior leadership. I’d be like, man, that’s going to be tough. They’re like, what is the requirement? I’m like, we can just throw a bunch of servers at it. It’s going to be expensive. How expensive? For this event, $5000. Then, they laughed. I was like, bro, this is not even worth the conversation. We just wasted that much in dollars.
It was a nice luxury of having. Obviously, we weren’t flipping with money. You shouldn’t be and all that stuff. Frugality has its own reward. In the sense of having your database managed, I think there’s a lot of value there if you can swing it.
Keith: Yeah. It’s the core things of your business. If this goes down, what is the impact to the business? What’s the chance of it going down if someone else is managing it versus yourself? I don’t think doing a managed server from the beginning was the right move. Once we started having issues, we should have really looked at it instead of trying to do multiple migrations to other self-hosted stuff.
Rob: Yeah, I think that makes sense. As we transition to closing, as we’re getting to time, I did want to dig in, we teased it at the top of the show that your growth has really accelerated since April of this year. Just over the past five months, there’s a real noticeable uptick in your revenue graph. Of course, I’d attribute that to you starting TinySeed. I am curious, what have you done differently? Obviously, in TinySeed, one of the earliest things to talk about is pricing. A lot of the SaaS founders just don’t have pricing dialed in with the value metrics, whether it’s too low. You tweaked with your pricing. I’m curious if that had an impact or what else?
Keith: I think that there were two main events in SegMetrics’ five-year life that moved the needle. One was focusing on it full time. There’s a big jump in revenue starting when I decided to focus on it. The second one was TinySeed. The jump for TinySeed was much bigger than the first one.
The way we changed pricing, I think, had a lot to do with it. What we had originally with our pricing model was essentially large buckets. You were in the starter bucket until you hit 50,000 contacts. As soon as you had 50,001, you had to pay $100 extra. It was difficult because people try to keep their contacts low. People would always email us. Like, hey, I’m only one over. Can I have it cheaper for now? I was like, yeah, sure. Fine. Just one.
People, they upgrade processes with manuals. There’s always stress around it. It’s this whole thing. The pricing is actually pretty similar. I think for the majority of people, they’re paying around the same amount. What we changed was that pricing is now increasing based on the number of contacts you have but only $5 at a time.
The big difference is now not that you are going to hit a wall and suddenly be paying twice as much. It’s like boiling a frog, you’re slowly going up as you get more profitable. As you succeed in your business, you’re going to pay us just a little bit more. That, I think, has made it much easier for people to do that upgrade because people don’t really care about the extra $5 a month. They do care as soon as they hit that threshold of, okay, now, your bill has doubled.
Rob: That’s the thing with pricing. You didn’t really change your pricing. You kind of changed how it auto adjusts. That’s one of these things that is a challenge to foresee if it’s going to make a difference. I think there’s a lesson folks can takeaway. If you do have these big gaps, maybe have smaller tires in between the published tiers. We did this as well with Drip back in the day, where we would go based on subscriber count and have it go up every 1000 subscribers or every 2000 subscribers versus every 10 or 20, like we originally did. It did make a difference for us.
It’s almost closer to metered pricing. True metered would be like $0.5 per subscriber. For you, it would be absolutely per contact. You’re not doing that. It’s still in small tiers but I do think that there’s value in thinking about that.
Keith: Yeah. The other part of it, I think that’s the biggest one. Also, just deciding what integrations, kind of the Zapier model of, okay, if you’re using HubSpot, you’re not going to be a hobby user. Your base price is going to be higher. You have to start out in a higher tier if you are higher level. They require more support, they require more effort. We’re dealing with bigger companies. That, I think, also helped a lot. Before, it was just contact-based. Now, it’s contact plus features.
Rob: Sir, thanks again for joining me on the show. If folks want to keep up with SegMetrics on Twitter, it’s @segmetrics. Obviously, segmetrics.io. You, let me see if I can pronounce it right this time. Is it harisenbon?
Keith: That’s close enough.
Rob: How would you pronounce your Twitter handle?
Keith: Ha-ri-sen-bon.
Rob: Harisenbon, @harisenbon79. We’ll link it up because it’s kind of hard to spell.
Keith: I’m so bad at naming. I can’t believe I ever got into programming. It’s really what it comes down to.
Rob: The two hardest problems in programming are naming cache invalidation and off by one errors. Yeah. You’ve heard me tell that on MicroConf.
Keith: I love that joke.
Rob: Sir, thanks again for joining me on the show. I hope you had fun today.
Keith: I did, Rob. Thanks so much for having me.
Rob: Absolutely. Thank you so much for joining me today. I hope you enjoyed my conversation with Keith Perhac. If you have not headed to startupsfortherestofus.com and entered your email address to receive the two exclusive episodes and PDF guides, I would encourage you to do that. The first one is called 8 Things You Must Know When Launching Your SaaS. Second is 10 Things You Should Know As You Scale Your SaaS. These are two podcast episodes. They’re Rob solo adventures where I run through 8 things and 10 things respectively, that I think you should know as you launch, then as you scale a SaaS app. These are things that I have not released on the podcast. They’re not on my blog and really not available anywhere else.
Check it out, startupsfortherestofus.com. You can checkout the right message popup in the lower right or really go to any page and opt-in the right handside to join thousands of other startup founders who are bootstrapping and mostly bootstrapping ambitious SaaS apps.
That’s it for this week. I will talk to you again on Thursday morning on TinySeed Tales season two, episode eight. I will be here in your earbuds again, next Tuesday morning.
We’ll go through Keith’s background. You may have heard of him. He’s done at least one MicroConf attendee talk. He’s done a MicoConf mainstage talk. He used to host a podcast with Pat. Keith and I cover some really interesting ground today as he talks about why he shut down his million dollar marketing agency to build and double down on his SaaS.
Before we dive into that, I wanted to ask you a favor. If you’ve been listening to the TinySeed Tales episodes that are coming out on Thursday mornings, you have heard through episode seven that came out last week, there are two episodes left. Obviously, this Thursday and next Thursday. I’m curious to get your feedback on season two and frankly, just the whole concept of TinySeed Tales. Feel free to email me directly at questions@startupsfortherestofus.com. You can DM me on Twitter or you can mention me at @robwalling on Twitter.
Given the amount of time and money that they cost to produce, I’m curious to hear if you like the storytelling approach. Obviously, it’s a more produced form than really exists in our space. I enjoy doing them but I also want to make sure that they’re providing some type of value to you; whether it’s entertainment, motivation, inspiration, tactics—just anything that you’re getting out of it. I would appreciate hearing from you. Drop me a line and let me know what you think.
With that, let’s dive right into our conversation. Keith Perhac, thank you so much for joining me on the show today.
Keith: Thanks so much for having me, Rob.
Rob: Today, we’re here to talk about why a multi-million dollar agency owner decided to quit it all and move to SaaS. It’s a great topic.
Keith: It is. It sounds a lot more impressive when you say it.
Rob: Why in the world would you do that, sir? Now, we’re going to dig into that today. Just so folks have some context, you’re a software developer turned marketer—the dangerous combination. I love that combination whether it’s a marketer who learns how to code or a developer who learns how to market.
Keith: It’s like a superpower.
Rob: It really, really is. I don’t think people understand that enough. A lot of us developers, you do it for five years, you do it for seven years. You become senior and you’re like, man, I can do a lot of things. Then, you start over with marketing and it’s a grind. You don’t know any of it, you think it’s fluff. You get three, four, or five years into that and you pile those two on, it’s ridiculous. It’s like an epic, highlevel, multiclass in Dungeons and Dragons.
Keith: Yeah. Just to be able to understand how the internet and all that technology works makes you such a better marketer. People come to us and they’re like, why aren’t these things tracking right? Because you have no idea of how the internet works, why the scripts aren’t firing, and how URLs even work.
Once you understand that, it’s a superpower to get everything. That’s not even touching the automation you can do, it’s crazy.
Rob: Yeah. You were running a seven figure marketing agency. It was called Develop Your Marketing, focused on conversion rate optimization and building out funnels. You had marquee clients, big name clients folks I’ve likely heard of like Ramit Sethi and Eben Pagan.
You decided to build a SaaS on the side. I think you were using the same resources. You were kind of using the agency team to start building that out. That SaaS is called SegMetrics, segmetrics.io. I’m going to read a little bit about it so folks have a context of what you build, then we’re going to go back and kind of talk through your decision to build it, the highs and lows, the launching—just the whole story so folks can both be inspired by it and also feel the agony and the pain of what you felt in the early days. As well as takeaway some actionable stuff. Obviously, your story as a marketer and a developer, I think there’s going to be a lot of folks that can takeaway.
SegMetrics, your h1 is, “Get clarity on your true lead value in every step of the way.” The subtitle there is, “Get 100% clarity on where your leads come from, how they act, and how much your marketing is really worth. Get a handle on the Key Performance Indicators that matter most for your marketing funnels. Built by marketers, for marketers.”
When I think of analytics or attribution, I think of, okay, I have Google Analytics as this anonymous analytics and aggregated. I have a Mixpanel. There’s obviously those types of competitors for individual funnels and people walking through. Of course, I have Facebook Pixels, Google Pixels, and other things for conversions and dollar amounts. I think Mixpanel does that too. Where does SegMetrics fit into that mix?
Keith: The idea is kind of similar to Mixpanel in a way, which is we want to be able to see everything that anyone does in a customer journey. From what ad they landed on to how many times they viewed a page, to if they attended a webinar, to be able to understand who are the most valuable people who are going through your marketing funnel.
The problem with Mixpanel is that it has no native integration. It has no idea of revenue out of the box. It has a garbage in and garbage out problem. Unless you were really diligent about what data you’re sending into Mixpanel, you’re not going to get anything valuable out of it.
What SegMetrics does is we take that idea of like, okay, we want to see every event in an entire customer journey. Marketers are never going to be able to hook this up. What we need to do is integrate directly with all these tools to pull the data out of Google Analytics, out of Google Ads, Facebook Ads, your ESP, your CRM, your Stripe, your payment gateways—everything—and create an individual persona that we can then say this is this person from all this different sources brought together. This is their full customer journey.
Then, what we’re able to do is say, all right, we know that Facebook Ads, our lead value is $50 for each lead we bring in from Facebook. Within that, do we have actions that make people worth more money? Worth less money? Are there certain demographics that can make people more valuable? Is this idea of finding these segments of actions, or demographics, or people that are more valuable so you can then go after them more, be able to market to them better, and understand your audience better.
Rob: Yeah. That makes a lot of sense. It was certainly an issue that I’ve had marketing SaaS, as we were doing ad spend or even getting organic traffic of I had this aggregate numbers of, hey, this is what our churn is, for example. I couldn’t slice it based on demographics or oftentimes, even based on source unless I really have to finagle some stuff.
Keith: That’s why we built it. As a conversion rate optimization agency, that’s what we’re doing. We exported all of this data from all these tools, created a bunch of pivot tables. Five hours later, we had information.
Rob: Yeah. Inside SegMetrics, you can slice and dice it. You could look at churn. You could look at lifetime value based on all this stuff, right?
Keith: Exactly.
Rob: Okay, for me that paints a crystal clear picture. I think most SaaS founders who’ve gotten this far, who are doing $5000 or $10,000 a month or more, are trying to attribute stuff, know the limitations of having to build it custom.
We may have already answered my first question, then. My first question is why build a SaaS company if you’re running a seven figure agency? It’s obvious that over and over and over, you probably have to cobble this together with duct tape and baling wire.
Keith: Yeah. Essentially, we were working with an analytics agency—a friend—who did a lot of our analytics. We had a lot of our analytics done inhouse. We just spend so much time on it. We were spending probably 20%, 30%, of our week just pulling the numbers. That doesn’t even mean the analysis of what they’re doing but just pulling these numbers.
Okay, we have this webinar. What is the lead value of someone who attended the webinar? We pull all that data from whatever system we have then we pull it from all the tags. Then, we pull the revenue. Then, we match them together. Awesome. Then, we write up the report, the PDF, and everything. We take it to the client and they’re like, what about the people who came from organic versus paid? What’s that breakdown look like? I’m like, give us five more hours. We got to go through that whole thing all over again with these new things.
The analytics guy we were talking to and the guy on my team, we were talking about this, and he’s like, it’s just a database. It’s just a spreadsheet. Why can we not just slurp this data in and do this automatically? That’s where it kind of starts. Okay, could we do this? Could we scratch our own itch? Yeah, that’s where it kind of started from.
Rob: Today, you are a team of 10. As you said offline, “Growing very quickly.” Of course, I have your revenue graph here. You’re in batch two of TinySeed, I have access to your numbers. I will confirm that. Doing very well. In fact, your growth has accelerated. It really looks like at April, May, it starts kicking up which coincidentally—
Keith: I wonder what happened in April and May of this year? I have no idea.
Rob: I have no idea. Don’t think batch two started. We’ll get into that later on the interview. I want to do something chronological. You started working on this five years ago, back in 2015. You told me that you built it in two weeks, 2-3 weeks. That you had a customer the first week of launch. That sounds amazing. That is crazy, crazy fast—to build this whole that fast. Second, to get your first customer the first week of launch. Both of those things, how did those happen?
Keith: This is actually the second SaaS I built. The first one was Summit Evergreen which was a membership site platform for marketers. We had made some mistakes that time. We thought we knew what the customers wanted based on the consulting we have done. We built a very large, very complicated app that had a lot of features that turned out no one actually needed. It took us many months to get to market. Once we got to market, it was slow to get people in. It was very difficult.
With this, we built it to scratch our own itch. At the same time, we’re like, this is something that everyone needs. We’re not going to make the same mistake. What we did was we did a very hands-on, iterative process with our customers. We picked two or three customers—clients—that we were working with. We said, hey, we’re building this thing. Here’s the numbers that were looking to get this value. They would respond. We would say, awesome.
We did a raw dump of their data. We plugged in the engine. There’s no UI. There’s nothing at this point. There’s just me doing some math in a PHP file on the backend based off of the CSV. We get that in and we spit that out. We show it to the clients and we say, hey, for this webinar you just ran last week, this is the lead value. They’re like, oh my god, this is amazing. We’re like, okay, this probably has space.
Then, the team had a little bit of downtime. I think this was early February or late January. Right after a big launch. We knew we had two weeks of almost no client work. We decided, let’s put a challenge to ourselves. Let’s get the team together and we’re going to work on this fulltime for two weeks. We’re not going to do any client work because we don’t have much scheduled. We’re going to see how much of this we can build.
In two weeks, we pretty much had version one done. The engine was already built but the UI, the signup, everything around it, the creation of the reports, the spitting out the reports, the graphs, the everything we built around two weeks. Finally, we launched and it was the product of the day when we launched. Super excited about that.
Then, I found out that there was a space in our Stripe public key when I copy-pasted it into the site, no one was able to purchase. That was rough. It didn’t deter us. I think within a month, we were up to $1000 MRR.
Rob: Wow, that’s great. A lot of learnings from that. I think people think of an MVP as a limited version of a product. You really tripled down on that definition.
Keith: It was a text file. I actually have screenshots of me and Slack. Or not Slack, it was Skype. I just had a text file with six lines. I copy-pasted that. Again, is this valuable? I’m like, yes. That was it.
Rob: Yeah. I love that approach. I often talk about, in my first book, human automation of having VAs just do something on the backends and spit out a report. That’s really, in essence, kind of what you did there.
First customer in the first week of launch, you obviously solve a problem. 1000 MRR in the first month; were you getting those leads from clients, or were you actually doing marketing?
Keith: I don’t remember, to be honest. I know we had two clients that had decided to sign up as customers. A number of our clients we kept as just kind of free users. They weren’t interested in the numbers, but we needed it for our work so we did it internally. Then, the rest were people who found us either through Product Hunt or promotions that we did, tweets. That was five years ago. I don’t really remember who they were and where they came from.
Rob: Right. You mentioned to me as we were talking before the interview that you were at about $1000 MRR after the first six months. Is that right? Did growth plateau that much?
Keith: Yes. We didn’t hit $2000 until August of 2016.
Rob: That was more than a year later, because this was early 2015. What happened then? You basically rocketed to $1000 MRR, you solved the problem that people are obviously in a dire pain point. You flatlined, in essence, for a year. What happened there?
Keith: More than a year. More than a year, Rob.
Rob: You remember every minute of that. 15 months.
Keith: What happened was I had a day job. Not a day job like I was working for someone else, but we had the agency. The agency is pulling, like you said, $1 million+ a year. It’s really hard to take the team off of client work and put them on something that’s making $1000. We didn’t have any customers or any clients that paid us $1000, just $1000. That was inconceivable. I think our lowest contract was $10,000 a month.
It was very difficult for us to put the time into it. I think we language there—I’m looking at the graph—until mid-2018. Wow, you can actually see the spike. Mid-2018, I had decided that we were going to focus on SegMetrics. We always said, hey, we’re always the bride’s maid, never the bride. We’re helping our clients run these million dollar launches—multi-million dollar launches. We’re making good money but we want something that we control in our product, in our stuff. We had always thought this. We had SegMetrics there but we haven’t put any love and any energy into it.
That summer, I remember, I spent some time. We rewrote the UI. I said, we’re going to focus on this. Over the next six months, we’re going to transition out of consulting work, out of the agency work, and we’re going to start moving towards SegMetrics and something that we own.
I know it’s going to be slow because we make a lot from the agency and we need to wind that down slowly. That’s our goal. I was just so tired. I think the team was just tired of having this great resource that no one was using. We didn’t spend the time to make it worth it, to put it out there.
Rob: I remember having that same issue before I went full time in products. I was consulting. I had, basically, a micro-agency where it was either me or a few contractors that I markedup and billed out. It was software development. I remember billling $125 an hour, $150 an hour, somewhere in that range, for every hour. I was booked more than full time. 40+ hours a week I could work. I had these products on the side that were doing exactly that. I had a beach towel website that was doing $1000 a month. Net profit was $150 a month. I had DotNetInvoice which was doing a couple of grand a month, most of that profit.
When you compare those numbers, it’s like, I can make a couple grand in two days of work. It was such a struggle. I heard people call it an addiction. The cash agency work or consulting is this cash addiction. It’s amazing when you want to get to full time income or higher quickly but it’s really hard to move away from. As you said, the focus is constantly towards your high value, instant cash infusion, which of course, is working for clients.
It sounds like you got tired of it. You got fed up with it and you wanted to double down on something that you have built. You fired your whole team in order to do this in late December 2018. That must have been brutal.
Keith: It was rough. It was honestly rough. It wasn’t, hey, I decided to work on SegMetrics and I’m letting everyone go. The original plan was to bring everyone over and we’re going to slowly shift over. The team’s going to stay. There were a number of issues with that.
One of them was that same mental model that the company has of, hey, I can do work for clients and make a lot of money. Or, I can spend time and make no money with the SaaS, was also there with the employees, with my team. We actually had a number of conversations over six months. Essentially, what it came down to is, it was too hard of a mental shift to go from the client is asking something right now. I could spend an hour on that and the company makes X hundred dollars. Or, I can spend six hours working on SegMetrics and the company makes… There’s not a one-to-one translation.
At this point, I think we had done the agency for six years. Eight years, maybe? That was the challenge. We have an hour for dollar, time for money exchange with our clients right now. We do not have that for SegMetrics. We have time for literally nothing exchange. It was very hard for not only myself, but my team to prioritize that.
There are also other issues like when you only have less than 100 customers, you don’t need an account manager. Where do we take the account manager? We kept trying to find roles that didn’t fit for people. It was just very difficult. What I ended up doing at the end of 2018 was saying, hey, guys. You guys are incharge of SegMetrics. You guys work on SegMetrics. I’m going to handle all the client stuff so it gets it all of your plate.
The mistake I made was thinking that they understood SegMetrics as well as I do. I’ve been living it for a year at that point, mentally. Trying to think of, what are we doing next? What are we doing next? It was a mistake on my part. It was just a shift that couldn’t happen.
What happened in January, I said, guys, we can’t do this anymore. I helped find them new work, introduce them to clients. Honestly, it was heartbreaking. I worked with these guys for 6-7 years. It’s really rough. The good side of it—kind of the windside of it—is that because SegMetrics has been growing and because there’s very little of the agency side left, I’ve actually brought them back on in the last few months. I’ve brought the team back together and they’re now working in roles that I think run to their strength instead of the things I was trying to force them into, which is really wonderful. I love working with them and I’m glad that they’re back on the team.
Rob: That’s such a cool ending to that story. When you’re in the midst of that, it probably feels devastating. Yet, to circle back two years later and be like, hey, we have a product now that can afford all of us, that makes the salaries. It’s an incredible story. That’s cool.
As you’ve contacted people, I’m assuming you’re bringing them on one at a time, you email them like, hey, want to come back and work on SegMetrics? Are they stoked? Are they over the moon to do it?
Keith: I don’t know. Yes, they were. I was always very nervous about the whole thing because I let them go. I felt like I had failed them, in some way. It was very nerve-racking for me to reachout, to talk about that, and bring them back on. We had talked in the interim. It’s not like I had cut them out of my life completely. I hope there’s no ill will. I enjoy having them back on. Mentally and emotionally, it was a very rough time, I guess.
Rob: I imagine, it seems to me, if I were in your shoes, it would almost be a mix. You have to let these folks go, even working with them. At the same time, once that’s done, you were then full time on SegMetrics—focused, right? By January of 2019, this was a month or two later, you were, essentially, for the first time since you launched it, you’re all in on it. That had to feel good.
Keith: It felt good. It felt very good. It did come with some challenges, though. When there’s other people around, there’s blame to go around. I see this a lot with my family as well. It’s like, it’s noisy here, I can’t concentrate. Or, the kids kept me up last night. I can’t get my work done.
Then, when it’s just you, all those excuses go out the window. You’re like, crap. The reason I’m not being productive, the reason I’m not focusing on what I should be doing is not some external force on me. It’s because I’m an […]. I need to get in gear, get my mental state insync so that I can do my work, and focus on the things that are important.
Rob: Yeah, that’s such an interesting thing. You mentioned to me offline that your family actually left for six weeks and you weren’t able to go with them. They went to Japan, where you guys used to live. You were left alone at the house. Probably, your inner monologue is, finally, all the interruptions are going to stop. It’s going to be so quiet. I’m going to get so much done. That’s not what happened.
Keith: No. The first two days were great. After that, I just had to start wrestling with my own existence at that point. I’m like, why am I not being productive? I remember back when I was younger, I could pull those 14 hour days, it was great and I felt energized by that. Now, I’m almost 40, I’m going to be 40 this year. I don’t have that same energy. There’s a lot of mental stuff that went around that. I had to understand what are the things that make me productive, what are the things that don’t make me productive, and how can I get rid of the things that don’t make me productive.
Rob: Yeah. There’s so much about learning your own psychology, managing that, and learning yourself. Same thing for me, when I was in my 20s, I could do 12 hours a day plus, sometimes, 14 hours a day. That was the point where Sherry went to Africa for a month, I believe. During that time, I would come home from the day job and then I would kick on a season of Friends. I make dinner, just sit on the couch, and code. I was coding side projects. This was 18 years ago or something.
Man, I got so much done. I would basically work from 5-6 at night until 1 or 2 in the morning. I’d get up the next day and go to the day job. It was kind of exhilarating because I was building my own thing. Within a month, she came back and I had launched a product. I believe that was FeedChat, it was a really early one that I did that crashed and burned.
During that time, she came back and I started talking about Ross and Rachel as if they were my friends. I was like, oh, yeah, Ross was saying… She was like, you know they’re not real, right? You know that they’re not real people, right? That’s always been a funny joke.
It’s learning about your own psychology. Obviously, in my 30s and now early 40s, you have to know more about yourself, I think. Atleast, I have to learn more about myself, my ability to make myself focused, and make myself get stuff done. It sounds like you’ve gone through the same thing.
At the beginning of 2020, eight or nine months ago, you hired a project manager to manage you—to basically bust your chops. Tell me about that. It’s pretty smart. I know some people get executive coaches or business coaches who they meet once a week or twice a month or something. You hired someone who’s more in the business and almost they’re like driving tasks. They’re keeping you accountable.
Keith: Yeah. Even before I really had the team back, we were creating quarterly goals. We were creating, okay, this is what we’re going to be working on this month. It gave me two things. One, it kept me on task. If I went off rails too many times, sure, you’ve got something come up with whatever, she kept me on. Like, hey, if you don’t start on this stuff, we’re not going to finish it by the end of the month. We’re not going to finish it by the end of the quarter. Usually, the things that you said were important.
That was one thing that was highly valuable to me because I default the coding. I don’t default to launching or to marketing or to any of that. I default to sitting and building out new features because that’s what I enjoy doing. That’s not going to move the product. She was very good at keeping me on what needed to be done for the business.
The second part of that, which I thought was just as valuable, was that at the end of the month or at the end of the quarter, she’s like, here’s all the things you got done. It was mind blowing. I’m one of those people who no matter how much I get done, it never shows that I got anything done. I feel like I’m constantly busy but I’m not getting enough done in the time. To have her come and we go back over the last month or the last quarter and say, we got 80% of the key tasks you said that you’re going to get done. You got all these other small things that came up during the month that, maybe, didn’t get done. The key things you said needed to get done this month, got done. That was amazing. It was empowering to me.
Rob: Yeah. The accountability alone—to end that, it’s knowing yourself, right? Some folks I know, they can go to the gym, they want to do it on their own, or they get equipment at home and want to workout in their own garage and prefer not to be in the social setting. Other folks want a trainer so that they have to show up this many days a week and get their chops busted. I think that’s kind of a cool hack. Again, I’ve heard other folks hiring CEOs, coaches, or executive coaches but this was a little different take on that. I thought it was interesting.
Keith: It was actually Ramit Sethi who hired someone off Craigslist to slap him each time that he looked at Reddit or anything like that.
Rob: Oh, geez.
Keith: He did a whole blogpost about this. Essentially, he hired someone to sit next to him. Everytime he goofed off, looked at Facebook or something, she just slapped him.
Rob: That’s like a reality TV stunt.
Keith: That’s the value that having my project manager gives me. She’s not physically slapping me but that’s the value that I’m getting out of it. Like, hey, stay on task. You’ve got stuff to do.
Rob: Right. It sounds like you’ve kind of hacked your own psychology a bit with this project manager and fixed that weakness, I guess, for now. Switching gears a little bit, you talked about—I saw it in the TinySeed Slack—that one of the low points of your year was earlier this year. It was a technical snafoo with the database. I’m going to make you relive this. We’ve all been there, you’ve just got to tell the story, man. It’s going to be painful. Do it once. We’ll get it on tape.
Keith: Databases, they are my kryptonite, I guess. What happened was that there’s something in Maestro 57 or whatever you’re using that made the database fillup in about an hour. We went from 30% full to completely full in an hour. Of course, if it’s full, it’s not going to write new data. We’re f-up there. Trying to figure this out, freaking out, and there’s no way to compact it down. I think it’s like a 12-year bug in mySQL.
I finally gave up and said, okay, we’re just going to export the database, create a brand new one, and do it over. We did it. All right, we’re safe. Cool. Two weeks later, the exact same thing happened. This has taken a week of my life at this point. Just to migrate this thing, do it, and make sure everything’s done in this whole thing. Then, we have to do it again. I finally say, I can’t do this anymore.
We moved to a managed hosted solution through DigitalOcean who’s our providers. They have a hosted database setup. We migrate everything over there. Finally, we’re good. All the tests were perfect.
I go to sleep. I wake up to my phone buzzing again. I’m like, oh my god, what now? Apparently, there are some setting differences between how they have it setup and normal mySQL that was causing a bunch of imports to fail. All of our tests ran. I think it was four weeks or maybe six weeks of just screaming constantly about this database issue, throughput issues, and speed issues. It’s just miserable. Just absolutely miserable.
I don’t know what people are supposed to take out of this because it was just painful. The thing that I took out of this was that the reason I was running the local database in the first place, not to manage one, is because it was a fourth of the cost. I was like, I can do this better, I can have it customized, and I’m going to be paying a lot less. That was great until the database exploded. Then, exploded again. I lost 4-6 weeks of productivity because I didn’t want to pay, I don’t know how much. Maybe $100, $300, $200, extra per month for managed solutions.
Rob: Man, as a bootstrap, I would have done the same thing. It can be obvious, in retrospect, like, oh, I just paid a few hundred dollars because it made sense. There’s so many decisions you have to make as you’re growing. You can’t always do the Mercedes.
Keith: You can’t throw money at all. There’s just too many.
Rob: That was a big difference once we sold Drip to Leadpages. You could just throw money at it. They had raised $38 million in venture. I remember having strategic conversations with the senior leadership. I’d be like, man, that’s going to be tough. They’re like, what is the requirement? I’m like, we can just throw a bunch of servers at it. It’s going to be expensive. How expensive? For this event, $5000. Then, they laughed. I was like, bro, this is not even worth the conversation. We just wasted that much in dollars.
It was a nice luxury of having. Obviously, we weren’t flipping with money. You shouldn’t be and all that stuff. Frugality has its own reward. In the sense of having your database managed, I think there’s a lot of value there if you can swing it.
Keith: Yeah. It’s the core things of your business. If this goes down, what is the impact to the business? What’s the chance of it going down if someone else is managing it versus yourself? I don’t think doing a managed server from the beginning was the right move. Once we started having issues, we should have really looked at it instead of trying to do multiple migrations to other self-hosted stuff.
Rob: Yeah, I think that makes sense. As we transition to closing, as we’re getting to time, I did want to dig in, we teased it at the top of the show that your growth has really accelerated since April of this year. Just over the past five months, there’s a real noticeable uptick in your revenue graph. Of course, I’d attribute that to you starting TinySeed. I am curious, what have you done differently? Obviously, in TinySeed, one of the earliest things to talk about is pricing. A lot of the SaaS founders just don’t have pricing dialed in with the value metrics, whether it’s too low. You tweaked with your pricing. I’m curious if that had an impact or what else?
Keith: I think that there were two main events in SegMetrics’ five-year life that moved the needle. One was focusing on it full time. There’s a big jump in revenue starting when I decided to focus on it. The second one was TinySeed. The jump for TinySeed was much bigger than the first one.
The way we changed pricing, I think, had a lot to do with it. What we had originally with our pricing model was essentially large buckets. You were in the starter bucket until you hit 50,000 contacts. As soon as you had 50,001, you had to pay $100 extra. It was difficult because people try to keep their contacts low. People would always email us. Like, hey, I’m only one over. Can I have it cheaper for now? I was like, yeah, sure. Fine. Just one.
People, they upgrade processes with manuals. There’s always stress around it. It’s this whole thing. The pricing is actually pretty similar. I think for the majority of people, they’re paying around the same amount. What we changed was that pricing is now increasing based on the number of contacts you have but only $5 at a time.
The big difference is now not that you are going to hit a wall and suddenly be paying twice as much. It’s like boiling a frog, you’re slowly going up as you get more profitable. As you succeed in your business, you’re going to pay us just a little bit more. That, I think, has made it much easier for people to do that upgrade because people don’t really care about the extra $5 a month. They do care as soon as they hit that threshold of, okay, now, your bill has doubled.
Rob: That’s the thing with pricing. You didn’t really change your pricing. You kind of changed how it auto adjusts. That’s one of these things that is a challenge to foresee if it’s going to make a difference. I think there’s a lesson folks can takeaway. If you do have these big gaps, maybe have smaller tires in between the published tiers. We did this as well with Drip back in the day, where we would go based on subscriber count and have it go up every 1000 subscribers or every 2000 subscribers versus every 10 or 20, like we originally did. It did make a difference for us.
It’s almost closer to metered pricing. True metered would be like $0.5 per subscriber. For you, it would be absolutely per contact. You’re not doing that. It’s still in small tiers but I do think that there’s value in thinking about that.
Keith: Yeah. The other part of it, I think that’s the biggest one. Also, just deciding what integrations, kind of the Zapier model of, okay, if you’re using HubSpot, you’re not going to be a hobby user. Your base price is going to be higher. You have to start out in a higher tier if you are higher level. They require more support, they require more effort. We’re dealing with bigger companies. That, I think, also helped a lot. Before, it was just contact-based. Now, it’s contact plus features.
Rob: Sir, thanks again for joining me on the show. If folks want to keep up with SegMetrics on Twitter, it’s @segmetrics. Obviously, segmetrics.io. You, let me see if I can pronounce it right this time. Is it harisenbon?
Keith: That’s close enough.
Rob: How would you pronounce your Twitter handle?
Keith: Ha-ri-sen-bon.
Rob: Harisenbon, @harisenbon79. We’ll link it up because it’s kind of hard to spell.
Keith: I’m so bad at naming. I can’t believe I ever got into programming. It’s really what it comes down to.
Rob: The two hardest problems in programming are naming cache invalidation and off by one errors. Yeah. You’ve heard me tell that on MicroConf.
Keith: I love that joke.
Rob: Sir, thanks again for joining me on the show. I hope you had fun today.
Keith: I did, Rob. Thanks so much for having me.
Rob: Absolutely. Thank you so much for joining me today. I hope you enjoyed my conversation with Keith Perhac. If you have not headed to startupsfortherestofus.com and entered your email address to receive the two exclusive episodes and PDF guides, I would encourage you to do that. The first one is called 8 Things You Must Know When Launching Your SaaS. Second is 10 Things You Should Know As You Scale Your SaaS. These are two podcast episodes. They’re Rob solo adventures where I run through 8 things and 10 things respectively, that I think you should know as you launch, then as you scale a SaaS app. These are things that I have not released on the podcast. They’re not on my blog and really not available anywhere else.
Check it out, startupsfortherestofus.com. You can checkout the right message popup in the lower right or really go to any page and opt-in the right handside to join thousands of other startup founders who are bootstrapping and mostly bootstrapping ambitious SaaS apps.
That’s it for this week. I will talk to you again on Thursday morning on TinySeed Tales season two, episode eight. I will be here in your earbuds again, next Tuesday morning.
Episode 519 | Profit Sharing, Stock Options, and Equity (A Rob Solo Adventure)
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On this episode, Rob talks through profit sharing, stock options, and equity and makes a comparison between these various approaches.
If you are thinking of ways to incentivize team members as a bootstrapper, this episode is for you.
The topics we cover
[04:34] Bonuses
[07:52] Equity Grants
[11:47] Stock Options
[20:09] Profit Sharing
[26:09] Which is best for your SaaS?
Links from the show
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Turns out, the rumors are true. This is Startups For the Rest of Us episode 519. Thanks for joining me again this week. I’m going to be running a solo adventure today, talking through profit sharing, stock options, and equity, and doing a comparison of those various with the thought of incentivizing employees and team members in mind. This is the conversation I have had at least five times and maybe six in the past three months, so I figured it was time to put some thoughts to tape so it’s a resource I can use to point people in the future.
If you’re thinking about whether as a bootstrapped or mostly bootstrap startup founder, whether to set up a profit-sharing plan to offer stock options to do equity grants or to just pay bonuses or other ways to incentivize your team members, that’s what I’ll really be working through today.
First, I got a couple of the best podcast reviews I think we’ve ever had. The first one is from BrettxKelly via Apple Podcast, and he said, “Rob is the Chuck Norris of bootstrap founders. Thanks for all you do, Rob.” I really appreciate that, Bret. I appreciate the sentiment and the creativity of it.
The other one, the subject line is, “The podcast that changed my life. This podcast was instrumental in my journey from a blah day job to a successful tech founder. Rob and Mike for the first 450 episodes (or so) bring useful, actionable advice every week. I also really appreciate the honest delivery with none of the radio DJ sliminess that so many podcasts seem to embrace.”
Thank you so much for those reviews, and if you haven’t left us a five-star review in Apple podcast, Stitcher, Spotify, or wherever you partake of this show, I would really appreciate it because it definitely helps keep us motivated and it helps bring more listeners to the show.
Next, I wanted to mention hey.com. I’ve mentioned in the past that Basecamp is a headline partner with MicroConf and in partnership with MicroConf, I have had a few Basecamp ads on the show. We are switching those up, and are now for hey.com. If you’re listening to this podcast, you may have heard of it.
If you go to hey.com, you’ll essentially see that the folks at Basecamp have created an entirely new email service, and they say it’s “email’s new heyday. Email sucked for years. Not anymore — we fixed it. HEY’s fresh approach transforms email into something you want to use, not something you’re forced to deal with.”
Hey allows you to screen your emails like you screen calls. You can fix bad subject lines without busting threads, easily find your most important emails every time you log in. They have a built-in reply later workflow that was built from the ground up, and they block email tracking pixels among many, many other things.
I know many of you listeners are already using hey.com, but if you have not checked it out, head over to hey.com and you can try it free. Thanks to Basecamp and Hey for supporting independent startups, MicroConf, and Startups For The Rest of Us.
Let’s dive into our topic for today. As I said at the top of the show, I’m going to be talking through profit sharing, stock options, and equity. I touched on bonuses real quick just as a side note because it occurred to me as I was writing this outline that I should probably address that.
I had this conversation a bunch of times in the past three, four months, and have sent out a bunch of thoughts via email to folks. And I realized, if I just gathered those thoughts, put the bullets on paper, and talked it through that I can probably create, hopefully, an evergreen resource for folks who are thinking about motivating their team members.
I should be really clear that I’m not a lawyer, I’m not an accountant. Do not consider this legal tax advice or any kind of tax advice other than things I have learned from my own experience dealing with these types of incentive programs.
I’d also like to point out that I actually had a conversation with Dru from Trends.vc. If you haven’t checked out Trends.vc, Dru is putting out two reports a month on different trends he’s seeing in the startup space, the bootstrapping space, and he’s creating insightful reports and thoroughly thought out reports. I believe the reports are $20 each if you want to buy the paid version. Each one has a free version, or you can just subscribe for a nominal fee per year. I’m a premium subscriber.
He and I had a conversation a couple of weeks ago when he was preparing his report on profit sharing. If you haven’t checked that out, head to Trends.vc and you can pay a one-off $20 to read his report that’s focused on profit sharing. But today I’m going to be talking about profit sharing, stock options, equity, and touch a little bit on bonuses.
Let’s start with this first question of, I have one, five, ten team members. Why should I give them anything beyond just a salary or their hourly rate anyway? The idea is to align incentives. It’s to motivate people, not just by giving them amazing work to do every day, but to give them a financial incentive to really stick around.
Some people look at it as a retention incentive to not go elsewhere if they can do the same work and make more money. Others look at it as a way to make people just enjoy their jobs more or want to work a little harder and put in some extra hours because they feel like they can make a difference.
There’s a lot of different ways to do it, and of course, this is not a requirement. Giving bonuses or profit-sharing isn’t a requirement, but I personally feel like if your team is cohesive and is working hard to get the same end goal and you are creating profit, creating value, creating wealth. To me, it does feel right (in some way) to share that with your team members.
The first question of why not just give bonuses? Well, you can, and maybe in the early days, that’s something to think about. The big downside to that is oftentimes, bonus programs are pretty arbitrary. You’ve really just had to make a call and say you get a few thousand, here you get $5000, you get two weeks of pay at the end of the year or whatever.
It can feel a little squishy if you try to do this overtime for many years. People can feel like they get left out or they play favorites. Or if they talk among one another, they can feel like perhaps you’re giving more money to someone who doesn’t deserve it. You also don’t want to reinvent the wheel every year. You don’t want to have to reevaluate every year who gets how much bonus and why. As I said, it can feel or even be arbitrary.
In addition, there have been lawsuits from employees of companies where they’re given bonuses every year and they come to count on those bonuses as part of their income and the employees won. I believe this was in California many years ago, so even using the word bonus can be dangerous if you do it year in, year out.
If I were a brand new startup, I had one or two employees, and I wasn’t able to give a bonus one year or maybe two before I got something really structured in place, that’s probably okay. It’s a risk tolerance thing, but it can be dangerous long-term in terms of people to become reliant on it. And if there’s no formula (so to speak) of how to calculate that, which is what profit sharing and the others give you a formula or it’s a set thing that you don’t have to keep rethinking about and reinventing.
Lastly, bonuses are tough because incentives aren’t exactly aligned, are they? Something about profit sharing that’s nice is if the company doesn’t churn a profit that year, people don’t get the profit sharing. Whereas if a company doesn’t turn a profit and you don’t give bonuses, people can be really angry, and they can blame management or their owners. Or they can say it’s mismanagement, and you spent too much money on whatever thing that they don’t like. Therefore, we didn’t get bonuses because we didn’t get a profit.
Bonuses, I think, have a time and place. I think these days, profit sharing or stock options are actually probably better ways to go.
The second thing I want to touch on is equity, and I’m going through this almost in a reverse order of which I think you shouldn’t do. The reason equity is tough, meaning if you just give 1% of your company to the first employee or 3% to the CEO you bring in. Equity grants are not stock options. These are equity grants where you are literally giving a portion of the company. They are taxable on the current value of the company.
While that can be arbitrary, if you have a company—SaaS companies that are doing millions in revenue and you’re trying to give someone 1% of it, the IRS is not going to believe you when they file that the value of that 1% is $1000. You can have serious taxable events if you are given a substantial amount of equity or even an insubstantial amount (to be honest) if the company is large enough.
Now, I will say, if you run a services business, oftentimes—if you run an accounting firm or a legal firm—those can tend to have buy-ins, whereas you come up to become a partner, they value the business. They say, okay, you need to buy 5% or 10% of this business, and you have to buy-in that amount over the course of years. The partners are (in essence) taking that money out.
That’s not a taxable event for the person buying in, that’s different. It’s not an equity grant, that’s just buying into a business, and that is a model. Professional services usually use that model. I’m not talking about that, I’m talking about you’re running a SaaS company and you’re considering just granting equity to someone.
Aside from it being a taxable event based on the current value of the company. Assuming you are running a pass-through entity like an LLC in the United States, if you give someone equity, they now get a K-1 at the end of each year, which makes their taxes more complicated. And if they have never dealt with a K-1, they’re maybe going to want to hire an accountant to do it.
You can imagine this isn’t a big deal if it’s two founders of a company, but what if it’s 20 or 30 employees that you want to incentivize? You’ve suddenly complicated everyone’s taxes. That’s not an ideal outcome.
Another thing to think about is whether you are an LLC or a Corp, you need to have restricted units that vest over time. This would be, even with an equity grant, I wouldn’t tend to just give someone 1% or 3% right at the start. Typically, you have a four-year vesting period, and there’s an initial one-year cliff where they have to work for a year before they get any of the equity. And at that point, they get 25% and then vest it over the three years. That’s the most common approach. Obviously, talk to a lawyer to get specifics.
The interesting part about equity is it does make profit-sharing easy because if someone owns 5% equity and you take out a distribution, then they get 5% of that distribution. It’s simple. It’s tried and true. Equity has been around for hundreds and hundreds of years. It is simple in that respect, but honestly, there can be a danger too.
Let’s say you have an LLC. It makes $500,000 in profit that year, and you’ve given 1% equity to a key employee. Even if you haven’t’ pulled money out, it’s still in the LLC bank account. They get a K-1 for 1% of that $500,000, which will only be $500,000. But in essence, they would then have an income tax bill of $5,000 even though no money came out of it.
Equity makes things complicated. I’ll just put it that way. Know what you’re getting into. To me, equity is for founding employee type folks. If you have co-founders, you know what you are getting into. Straight equity with some vesting is something that a lot of us do. That’s how it’s normally done. But for employee incentives and aligning incentives, I don’t think personally it’s the best way to go.
One last note, if you hold equity for less than a year, it’s short term capital gains. And if you hold it longer for a year, then it’s long term capital gains. That’s one of the best parts of it is if you do have an exit, whether you sell your shares or whether the whole company gets acquired, you do get that nice capital gains treatment. Instead of essentially paying income tax levels on it, you pay 15% or 20%. There’s a much nicer basis there or there’s a much nicer tax outcome. Those are my thoughts on equity incentives.
Let’s move on to stock options, which are the standard Silicon Valley way to motivate folks above and beyond their salary. A stock option is just an option to purchase stock in the company. It’s a specific amount. You’ll say you have 10,000 options. It means you have an option to purchase 10,000 shares at a particular price called the strike price, and that’s set each year by a company’s filing with the IRS.
That strike price is usually quite a bit less than their last funding round. It doesn’t always wind up being that way, but what they say is, okay, you’re starting with us today. Here’s 10,000 options. You have to work for a year. […] Work a year, then you get $2500. And then each month after that, you get essentially 1/36 of the remaining amount up to four years. They typically give you another big chunk of options to keep you retained so you’re always working to just build that up.
A lot of folks don’t exercise their options. They just keep them around, and as long as you’re working at the company, you can just wait until there’s a liquidity event. Of course, the downside of that is paying short-term capital gains on it.
The good news about stock options is there are no capital gains to worry about. If you grant someone options, there’s no real value to them because essentially there’s an option to purchase at the price the company was worth when you’re given the option, so that’s not a taxable event. And they don’t receive a K-1 that complements their taxes, since they’re just an option to buy a share in the future.
It’s actually not owning equity, and there’s no profit sharing unless you would execute the option. They’re designed to payout if you have a liquidity event like going public or being acquired. I guess if you had options in an LLC, it wouldn’t be called stock because there’s no stock in an LLC but unit options, and then you exercise holding those. In theory, if the LLC took a dividend or distribution, you could get that. It’s a very uncommon scenario, and I don’t think people would typically go for that.
The other interesting thing about options is there’s usually this exercise window where if you leave the company and you haven’t exercised any of your options, you usually have about three months. And if you don’t buy the options, they just revert back to the company and you get nothing. I don’t really like that. I actually disagree with that. I don’t think it’s super ethical. I feel like that window should be much, much longer—one, two, three years—and there is a push for that to get longer because it kind of screws employees.
You think about an employee who comes in and they’re going to get 10,000 shares at a $2 strike price. That’s $20,000 worth of options. They work for the company for the full four years, and then they leave. They have this $20,000 that they could purchase. Maybe they don’t have that much in cash, or maybe it’s not a gamble that they can make at that time. But maybe the company sells or goes public a year or two later at $10 a share.
It’s a big gamble for some people to make, and I feel like having a longer time to evaluate that and a longer time to be able to purchase options feels to me like a better way to do it, a more fair way to do it.
The last thing before I tell you my own story about an experience with stock options is that if you exercise your options, you pay the money, then you own the stock in essence. Usually, it’s restricted stock, but it depends on if the company is private. It often has restrictions that you can’t sell it for a certain time.
But if the company is private, then you are typically just holding stock that you can’t sell. If they’re public, you can typically execute and then sell the same day or the same week. You then pay short-term capital gains on any gains that you get. You pay income tax. What I have heard about are folks who have enough money that they’ll exercise them. Hold them for a year, hope that the stock is still higher than when they exercise, and then you get long-term capital gains treatment on that.
My own story with stock options is back in probably about 15 years ago, I was a lead developer and a technical lead for an early prepaid credit card company in LA. We got options and I worked there—I got X thousand options granted, and I only stayed there for 2 years before I went out on my own.
I got half the options that were granted, and when I left, I had to make the decision within 60 or 90 days. Do I buy these? I did, I bought them all. I wound up spending under about $10,000, which is quite a bit of money for me at the time. I figured, hey, it’s a gamble. Maybe it’ll turn out.
Within a year or two of leaving, they raised another round of funding. They didn’t go public, but they allowed people who owned stock to sell a certain percentage of it. I don’t believe I sold any in that offering, but I did sell a little later for about half of it for 10X gain, and then another half for between 10X and 20X gain. It was several hundred thousand dollars, which was obviously really nice at that point in my life. We used a big chunk of it as a down payment on a house, then a chunk of it to fix the roof on the said house, and fix a bunch of other stuff that was broken. Don’t get me started on homeownership. But all in all, it was a good outcome.
If I had stuck around another 2 years I could have made double the money. But I’ve always thought, those were the years that I really cranked up on entrepreneurship. I started writing my book. I built the Micropreneur Academy. It was some early-day stuff. There were a lot of opportunity costs that probably wouldn’t have been worth it.
But my experience with stock options is that one experience. They did later go public, and I actually sold the last of my shares after they went public. My experience, of course, was positive. The reality is in almost all cases, there is no liquidity […]. Most startups fail. Most venture-funded startups fail, and so most venture-funded stock options really aren’t worth it. They just aren’t worth the money, aren’t worth the paper they’re printed on (so to speak).
That’s the reality of gambling on startups. We know that as founders. That it’s dangerous and that it comes with risk. I think it’s harder as an employee when you have so much less control over the company and over the success of it. But these are your choices that you have to make as an employee.
Now, as a founder, as a CEO, if you’re going the Silicon Valley route, you’re raising a big round of venture funding, and you’re doing the Delaware C-corp, stock options are the standard way. If you did anything else, people would look at you funny. I think with bootstrap startups, you can do this.
I think a big question is stock options typically aren’t worth much unless you plan to have a liquidity event, and that doesn’t mean sell or go public necessarily. You can sell shares on a secondary market. Future employees can buy them back. Founders can buy them. There can be some type of liquidity events that can happen. You could take just a minority investment even at some point if you wanted to provide liquidity for employees with a stock option pool.
The bottom line is most startups and most SaaS apps do sell at some point. The vast majority, they do sell within whatever timeframe we could define, 7-10 years. There are very few bootstrappers who are still running the same SaaS product that they were running 10 years ago. That is a reality to think about is there may likely be a liquidity event even if you don’t particularly plan on it today.
I think stock options are a reasonable choice. I hate to even make a recommendation for or against. I think they’re a longer-term play for sure because they do require that liquidity to be worth anything versus profit-sharing, which is more short-term cash out of the business type approach.
But frankly, if you’re not going to pull cash out of the business, if you’re in a high growth market—I think about when we were growing Drip—we weren’t pulling cash out of the business. If we had implemented profit sharing, people would have wanted us to become profitable. The goal at that point was not to be profitable yet, it was to keep growing. In that sense, I think a better motivating or incentive alignment would have been through the use of stock options, even though that can feel weird.
I think about an LLC having stock options, and it’s totally possible to set up a structure like that, but it can feel a little different than the typical C-corp setup. Again, I want to reiterate that not only am I not a lawyer or an accountant, but there are just a lot of pros and cons to these things. If there were one right answer, then everyone would choose to do that. It just depends on the situation and the specifics of the type of company you’re trying to build and how you’re building it. If it’s going to be profitable in the short-term versus long-term, and how you want to structure things for yourself.
Lastly, let’s talk about profit sharing. What’s nice about profit sharing is if you don’t ever plan on selling or having liquidity events, then money and profit distribution make sense. It’s what real businesses are built on. Real businesses sell real products to real customers. To me, again, it makes sense to share those in some form or fashion that the employees and the team members who are building that company with you get to share in some form or fashion.
One drawback to profit-sharing that you don’t see with the other approaches is that if an employee leaves, they don’t take the profit-sharing with them. It ends when their tenure with your company ends. It’s not like having equity or stock options where you can hold onto these things for a future gain. I left that credit card company two, three years before it went public. But I had that lasting piece of equity that I had exercised. It’s maybe not as ideal for employees who want to leave, which works as an incentive to keep them there but can also be a bummer for folks when they leave.
One thing I would think about if I were structuring profit sharing is to make it a pool, not a committed percentage to an individual. That’s a mistake you can make with an early employee is to say, oh, you get 1%, 2%, or 3% of profits. I would think more about, hey, let’s have a 10% profit sharing pool, and all key employees share in that, or all employees share in that.
Such that as you add more people, obviously, that first employee’s percentage of the whole chunk will go down. But ideally, the company should be growing, and these individuals should be contributing to that. If you’re going to do profit sharing, you probably want to stay away from being a C-corp because that’s going to give you double taxation, so you’re going to want to be in a pass-through entity.
Again, I mentioned Trends.vc at the top of the show, but there’s a really good report that Dru put together over there talking about the ins and outs of profit sharing. The best article I’ve ever seen written on profit sharing is from Peldi Guilizzoni. He wrote about the profit-sharing that he designed for Balsamiq. We’ll link that up in the show notes. But he basically said, they started off with a 10% pool—10% of the profits. I believe each quarter was distributed, and then he moved that to 15% at a certain point, years into the company. Now he’s up to 20%. I love that range right there. That feels really solid to me. To be honest, that 10%-15% stock option pool is also the standard size that a Silicon Valley startup would have.
That number does ring in that zone that I feel personally comfortable with. From Peldi’s article, one thing he talks about is they do quarterly distributions, which is probably what I would do if I was going to do it because if you do monthly, it’s too often. It’s just too much paperwork. If you do yearly, then people wait around and it’s bonus season. People will stay past that mark.
If they’re unhappy, they collect the profit sharing for the year, and then they take off. I don’t like that gap. It should be 3 or 6 months tops. But Peldi says, “Our quarterly bonus program allocates 20% of profits to full-time employees: 25% is split equally and 75% is split based on seniority, then it’s all weighed by the cost of living in each location.”
That’s how he structures it, and I do like that there’s a part split equally. There’s a part split by seniority. I have also heard of folks doing it based on the amount of salary people make, and then not having that cost of living of your location factor in because that’s already factored in.
One thing I would stay away from personally is using performance evaluations as some type of thing that affects profit sharing. That can be dangerous as different managers across a company might rate people differently. Basically, you should have A-players on your team, and if not, then they need to be let go in essence. If someone is performing at a subpar rate, then you need to be addressing that rather than essentially docking a bonus because there’s a lot of ways that this can backfire. Personally, I would not be including employee performance as a part of the criteria.
One drawback of profit sharing is that it’s really always taxed as income. It’s a big hit. If you’re talking about, you’re in the 33%, 35%, or 40% tax bracket, and you get a chunk every 3 months in essence, that’s a big difference versus if you were drawing out dividends. I guess through a C-corp, you’d pay double tax on it anyway. Or if you had a stock that you were able to sell, that long-term cap gains is a really big difference, and it can make a really big difference in the tax bill. But that is what it is.
Profit-sharing is cash. It’s a short-term motivator. I shouldn’t say short-term because it can motivate people over the long-term, but it really does allow employees to focus on not only growing the top line but potentially looking at reducing expenses, which the profit is obviously the revenue minus expenses.
I do think that a lot of folks in your company can impact the net profit that it has. If they’re thinking about their share of that, it does a pretty good job of aligning those incentives in a way that perhaps stock options are pretty nebulous.
Why is the stock worth more? Well, it’s typically worth more when someone buys the company or when you raise that next funding round. Is me saving $2000 a month on our AWS bill going to really impact the value of my stock options? It’s very unlikely versus profit sharing. You can see the money hit the Excel spreadsheet, the Google Doc, and you could see how it could literally trickle down to not only the company’s bottom line, but then to your own.
Some companies have folks vest into profit sharing or not be eligible for the first 6 or 12 months. I don’t think that’s unreasonable much in the same way that many companies have a waiting period to get on health insurance or to start a 401(k). This is another perk that makes sure the person’s a fit for the team, that the team is a fit for the person, and then evaluate getting them set up with all of the benefits.
These days, if I was going to evaluate these approaches for my own SaaS startup, I would think about whether I was going to be able to run it profitably. Obviously, profit sharing might be the choice then. Think about whether I was going to grow this and sell it, or have a liquidity event at some point. Then obviously, stock options might be a better opportunity.
Again, I think bonuses can be useful in the early days, but personally, they’re a little too arbitrary and can create a little bit too much chaos or just reinventing the wheel syndrome every year to personally be my favorite for having to run it long-term. And then equity, obviously, I mentioned, if it’s founder-level folks, then you can talk about that. But there are a lot of complexities there—taxable events, K-1s, and all that—that I don’t think scales to a full workforce.
Thanks again for joining me this week as I talked through different ways to incentivize your team members. If you have thoughts or comments on this episode, please give me a shout out on Twitter, @robwalling and @startupspod. I will talk to you again in your earbuds next Tuesday morning.
If you’re thinking about whether as a bootstrapped or mostly bootstrap startup founder, whether to set up a profit-sharing plan to offer stock options to do equity grants or to just pay bonuses or other ways to incentivize your team members, that’s what I’ll really be working through today.
First, I got a couple of the best podcast reviews I think we’ve ever had. The first one is from BrettxKelly via Apple Podcast, and he said, “Rob is the Chuck Norris of bootstrap founders. Thanks for all you do, Rob.” I really appreciate that, Bret. I appreciate the sentiment and the creativity of it.
The other one, the subject line is, “The podcast that changed my life. This podcast was instrumental in my journey from a blah day job to a successful tech founder. Rob and Mike for the first 450 episodes (or so) bring useful, actionable advice every week. I also really appreciate the honest delivery with none of the radio DJ sliminess that so many podcasts seem to embrace.”
Thank you so much for those reviews, and if you haven’t left us a five-star review in Apple podcast, Stitcher, Spotify, or wherever you partake of this show, I would really appreciate it because it definitely helps keep us motivated and it helps bring more listeners to the show.
Next, I wanted to mention hey.com. I’ve mentioned in the past that Basecamp is a headline partner with MicroConf and in partnership with MicroConf, I have had a few Basecamp ads on the show. We are switching those up, and are now for hey.com. If you’re listening to this podcast, you may have heard of it.
If you go to hey.com, you’ll essentially see that the folks at Basecamp have created an entirely new email service, and they say it’s “email’s new heyday. Email sucked for years. Not anymore — we fixed it. HEY’s fresh approach transforms email into something you want to use, not something you’re forced to deal with.”
Hey allows you to screen your emails like you screen calls. You can fix bad subject lines without busting threads, easily find your most important emails every time you log in. They have a built-in reply later workflow that was built from the ground up, and they block email tracking pixels among many, many other things.
I know many of you listeners are already using hey.com, but if you have not checked it out, head over to hey.com and you can try it free. Thanks to Basecamp and Hey for supporting independent startups, MicroConf, and Startups For The Rest of Us.
Let’s dive into our topic for today. As I said at the top of the show, I’m going to be talking through profit sharing, stock options, and equity. I touched on bonuses real quick just as a side note because it occurred to me as I was writing this outline that I should probably address that.
I had this conversation a bunch of times in the past three, four months, and have sent out a bunch of thoughts via email to folks. And I realized, if I just gathered those thoughts, put the bullets on paper, and talked it through that I can probably create, hopefully, an evergreen resource for folks who are thinking about motivating their team members.
I should be really clear that I’m not a lawyer, I’m not an accountant. Do not consider this legal tax advice or any kind of tax advice other than things I have learned from my own experience dealing with these types of incentive programs.
I’d also like to point out that I actually had a conversation with Dru from Trends.vc. If you haven’t checked out Trends.vc, Dru is putting out two reports a month on different trends he’s seeing in the startup space, the bootstrapping space, and he’s creating insightful reports and thoroughly thought out reports. I believe the reports are $20 each if you want to buy the paid version. Each one has a free version, or you can just subscribe for a nominal fee per year. I’m a premium subscriber.
He and I had a conversation a couple of weeks ago when he was preparing his report on profit sharing. If you haven’t checked that out, head to Trends.vc and you can pay a one-off $20 to read his report that’s focused on profit sharing. But today I’m going to be talking about profit sharing, stock options, equity, and touch a little bit on bonuses.
Let’s start with this first question of, I have one, five, ten team members. Why should I give them anything beyond just a salary or their hourly rate anyway? The idea is to align incentives. It’s to motivate people, not just by giving them amazing work to do every day, but to give them a financial incentive to really stick around.
Some people look at it as a retention incentive to not go elsewhere if they can do the same work and make more money. Others look at it as a way to make people just enjoy their jobs more or want to work a little harder and put in some extra hours because they feel like they can make a difference.
There’s a lot of different ways to do it, and of course, this is not a requirement. Giving bonuses or profit-sharing isn’t a requirement, but I personally feel like if your team is cohesive and is working hard to get the same end goal and you are creating profit, creating value, creating wealth. To me, it does feel right (in some way) to share that with your team members.
The first question of why not just give bonuses? Well, you can, and maybe in the early days, that’s something to think about. The big downside to that is oftentimes, bonus programs are pretty arbitrary. You’ve really just had to make a call and say you get a few thousand, here you get $5000, you get two weeks of pay at the end of the year or whatever.
It can feel a little squishy if you try to do this overtime for many years. People can feel like they get left out or they play favorites. Or if they talk among one another, they can feel like perhaps you’re giving more money to someone who doesn’t deserve it. You also don’t want to reinvent the wheel every year. You don’t want to have to reevaluate every year who gets how much bonus and why. As I said, it can feel or even be arbitrary.
In addition, there have been lawsuits from employees of companies where they’re given bonuses every year and they come to count on those bonuses as part of their income and the employees won. I believe this was in California many years ago, so even using the word bonus can be dangerous if you do it year in, year out.
If I were a brand new startup, I had one or two employees, and I wasn’t able to give a bonus one year or maybe two before I got something really structured in place, that’s probably okay. It’s a risk tolerance thing, but it can be dangerous long-term in terms of people to become reliant on it. And if there’s no formula (so to speak) of how to calculate that, which is what profit sharing and the others give you a formula or it’s a set thing that you don’t have to keep rethinking about and reinventing.
Lastly, bonuses are tough because incentives aren’t exactly aligned, are they? Something about profit sharing that’s nice is if the company doesn’t churn a profit that year, people don’t get the profit sharing. Whereas if a company doesn’t turn a profit and you don’t give bonuses, people can be really angry, and they can blame management or their owners. Or they can say it’s mismanagement, and you spent too much money on whatever thing that they don’t like. Therefore, we didn’t get bonuses because we didn’t get a profit.
Bonuses, I think, have a time and place. I think these days, profit sharing or stock options are actually probably better ways to go.
The second thing I want to touch on is equity, and I’m going through this almost in a reverse order of which I think you shouldn’t do. The reason equity is tough, meaning if you just give 1% of your company to the first employee or 3% to the CEO you bring in. Equity grants are not stock options. These are equity grants where you are literally giving a portion of the company. They are taxable on the current value of the company.
While that can be arbitrary, if you have a company—SaaS companies that are doing millions in revenue and you’re trying to give someone 1% of it, the IRS is not going to believe you when they file that the value of that 1% is $1000. You can have serious taxable events if you are given a substantial amount of equity or even an insubstantial amount (to be honest) if the company is large enough.
Now, I will say, if you run a services business, oftentimes—if you run an accounting firm or a legal firm—those can tend to have buy-ins, whereas you come up to become a partner, they value the business. They say, okay, you need to buy 5% or 10% of this business, and you have to buy-in that amount over the course of years. The partners are (in essence) taking that money out.
That’s not a taxable event for the person buying in, that’s different. It’s not an equity grant, that’s just buying into a business, and that is a model. Professional services usually use that model. I’m not talking about that, I’m talking about you’re running a SaaS company and you’re considering just granting equity to someone.
Aside from it being a taxable event based on the current value of the company. Assuming you are running a pass-through entity like an LLC in the United States, if you give someone equity, they now get a K-1 at the end of each year, which makes their taxes more complicated. And if they have never dealt with a K-1, they’re maybe going to want to hire an accountant to do it.
You can imagine this isn’t a big deal if it’s two founders of a company, but what if it’s 20 or 30 employees that you want to incentivize? You’ve suddenly complicated everyone’s taxes. That’s not an ideal outcome.
Another thing to think about is whether you are an LLC or a Corp, you need to have restricted units that vest over time. This would be, even with an equity grant, I wouldn’t tend to just give someone 1% or 3% right at the start. Typically, you have a four-year vesting period, and there’s an initial one-year cliff where they have to work for a year before they get any of the equity. And at that point, they get 25% and then vest it over the three years. That’s the most common approach. Obviously, talk to a lawyer to get specifics.
The interesting part about equity is it does make profit-sharing easy because if someone owns 5% equity and you take out a distribution, then they get 5% of that distribution. It’s simple. It’s tried and true. Equity has been around for hundreds and hundreds of years. It is simple in that respect, but honestly, there can be a danger too.
Let’s say you have an LLC. It makes $500,000 in profit that year, and you’ve given 1% equity to a key employee. Even if you haven’t’ pulled money out, it’s still in the LLC bank account. They get a K-1 for 1% of that $500,000, which will only be $500,000. But in essence, they would then have an income tax bill of $5,000 even though no money came out of it.
Equity makes things complicated. I’ll just put it that way. Know what you’re getting into. To me, equity is for founding employee type folks. If you have co-founders, you know what you are getting into. Straight equity with some vesting is something that a lot of us do. That’s how it’s normally done. But for employee incentives and aligning incentives, I don’t think personally it’s the best way to go.
One last note, if you hold equity for less than a year, it’s short term capital gains. And if you hold it longer for a year, then it’s long term capital gains. That’s one of the best parts of it is if you do have an exit, whether you sell your shares or whether the whole company gets acquired, you do get that nice capital gains treatment. Instead of essentially paying income tax levels on it, you pay 15% or 20%. There’s a much nicer basis there or there’s a much nicer tax outcome. Those are my thoughts on equity incentives.
Let’s move on to stock options, which are the standard Silicon Valley way to motivate folks above and beyond their salary. A stock option is just an option to purchase stock in the company. It’s a specific amount. You’ll say you have 10,000 options. It means you have an option to purchase 10,000 shares at a particular price called the strike price, and that’s set each year by a company’s filing with the IRS.
That strike price is usually quite a bit less than their last funding round. It doesn’t always wind up being that way, but what they say is, okay, you’re starting with us today. Here’s 10,000 options. You have to work for a year. […] Work a year, then you get $2500. And then each month after that, you get essentially 1/36 of the remaining amount up to four years. They typically give you another big chunk of options to keep you retained so you’re always working to just build that up.
A lot of folks don’t exercise their options. They just keep them around, and as long as you’re working at the company, you can just wait until there’s a liquidity event. Of course, the downside of that is paying short-term capital gains on it.
The good news about stock options is there are no capital gains to worry about. If you grant someone options, there’s no real value to them because essentially there’s an option to purchase at the price the company was worth when you’re given the option, so that’s not a taxable event. And they don’t receive a K-1 that complements their taxes, since they’re just an option to buy a share in the future.
It’s actually not owning equity, and there’s no profit sharing unless you would execute the option. They’re designed to payout if you have a liquidity event like going public or being acquired. I guess if you had options in an LLC, it wouldn’t be called stock because there’s no stock in an LLC but unit options, and then you exercise holding those. In theory, if the LLC took a dividend or distribution, you could get that. It’s a very uncommon scenario, and I don’t think people would typically go for that.
The other interesting thing about options is there’s usually this exercise window where if you leave the company and you haven’t exercised any of your options, you usually have about three months. And if you don’t buy the options, they just revert back to the company and you get nothing. I don’t really like that. I actually disagree with that. I don’t think it’s super ethical. I feel like that window should be much, much longer—one, two, three years—and there is a push for that to get longer because it kind of screws employees.
You think about an employee who comes in and they’re going to get 10,000 shares at a $2 strike price. That’s $20,000 worth of options. They work for the company for the full four years, and then they leave. They have this $20,000 that they could purchase. Maybe they don’t have that much in cash, or maybe it’s not a gamble that they can make at that time. But maybe the company sells or goes public a year or two later at $10 a share.
It’s a big gamble for some people to make, and I feel like having a longer time to evaluate that and a longer time to be able to purchase options feels to me like a better way to do it, a more fair way to do it.
The last thing before I tell you my own story about an experience with stock options is that if you exercise your options, you pay the money, then you own the stock in essence. Usually, it’s restricted stock, but it depends on if the company is private. It often has restrictions that you can’t sell it for a certain time.
But if the company is private, then you are typically just holding stock that you can’t sell. If they’re public, you can typically execute and then sell the same day or the same week. You then pay short-term capital gains on any gains that you get. You pay income tax. What I have heard about are folks who have enough money that they’ll exercise them. Hold them for a year, hope that the stock is still higher than when they exercise, and then you get long-term capital gains treatment on that.
My own story with stock options is back in probably about 15 years ago, I was a lead developer and a technical lead for an early prepaid credit card company in LA. We got options and I worked there—I got X thousand options granted, and I only stayed there for 2 years before I went out on my own.
I got half the options that were granted, and when I left, I had to make the decision within 60 or 90 days. Do I buy these? I did, I bought them all. I wound up spending under about $10,000, which is quite a bit of money for me at the time. I figured, hey, it’s a gamble. Maybe it’ll turn out.
Within a year or two of leaving, they raised another round of funding. They didn’t go public, but they allowed people who owned stock to sell a certain percentage of it. I don’t believe I sold any in that offering, but I did sell a little later for about half of it for 10X gain, and then another half for between 10X and 20X gain. It was several hundred thousand dollars, which was obviously really nice at that point in my life. We used a big chunk of it as a down payment on a house, then a chunk of it to fix the roof on the said house, and fix a bunch of other stuff that was broken. Don’t get me started on homeownership. But all in all, it was a good outcome.
If I had stuck around another 2 years I could have made double the money. But I’ve always thought, those were the years that I really cranked up on entrepreneurship. I started writing my book. I built the Micropreneur Academy. It was some early-day stuff. There were a lot of opportunity costs that probably wouldn’t have been worth it.
But my experience with stock options is that one experience. They did later go public, and I actually sold the last of my shares after they went public. My experience, of course, was positive. The reality is in almost all cases, there is no liquidity […]. Most startups fail. Most venture-funded startups fail, and so most venture-funded stock options really aren’t worth it. They just aren’t worth the money, aren’t worth the paper they’re printed on (so to speak).
That’s the reality of gambling on startups. We know that as founders. That it’s dangerous and that it comes with risk. I think it’s harder as an employee when you have so much less control over the company and over the success of it. But these are your choices that you have to make as an employee.
Now, as a founder, as a CEO, if you’re going the Silicon Valley route, you’re raising a big round of venture funding, and you’re doing the Delaware C-corp, stock options are the standard way. If you did anything else, people would look at you funny. I think with bootstrap startups, you can do this.
I think a big question is stock options typically aren’t worth much unless you plan to have a liquidity event, and that doesn’t mean sell or go public necessarily. You can sell shares on a secondary market. Future employees can buy them back. Founders can buy them. There can be some type of liquidity events that can happen. You could take just a minority investment even at some point if you wanted to provide liquidity for employees with a stock option pool.
The bottom line is most startups and most SaaS apps do sell at some point. The vast majority, they do sell within whatever timeframe we could define, 7-10 years. There are very few bootstrappers who are still running the same SaaS product that they were running 10 years ago. That is a reality to think about is there may likely be a liquidity event even if you don’t particularly plan on it today.
I think stock options are a reasonable choice. I hate to even make a recommendation for or against. I think they’re a longer-term play for sure because they do require that liquidity to be worth anything versus profit-sharing, which is more short-term cash out of the business type approach.
But frankly, if you’re not going to pull cash out of the business, if you’re in a high growth market—I think about when we were growing Drip—we weren’t pulling cash out of the business. If we had implemented profit sharing, people would have wanted us to become profitable. The goal at that point was not to be profitable yet, it was to keep growing. In that sense, I think a better motivating or incentive alignment would have been through the use of stock options, even though that can feel weird.
I think about an LLC having stock options, and it’s totally possible to set up a structure like that, but it can feel a little different than the typical C-corp setup. Again, I want to reiterate that not only am I not a lawyer or an accountant, but there are just a lot of pros and cons to these things. If there were one right answer, then everyone would choose to do that. It just depends on the situation and the specifics of the type of company you’re trying to build and how you’re building it. If it’s going to be profitable in the short-term versus long-term, and how you want to structure things for yourself.
Lastly, let’s talk about profit sharing. What’s nice about profit sharing is if you don’t ever plan on selling or having liquidity events, then money and profit distribution make sense. It’s what real businesses are built on. Real businesses sell real products to real customers. To me, again, it makes sense to share those in some form or fashion that the employees and the team members who are building that company with you get to share in some form or fashion.
One drawback to profit-sharing that you don’t see with the other approaches is that if an employee leaves, they don’t take the profit-sharing with them. It ends when their tenure with your company ends. It’s not like having equity or stock options where you can hold onto these things for a future gain. I left that credit card company two, three years before it went public. But I had that lasting piece of equity that I had exercised. It’s maybe not as ideal for employees who want to leave, which works as an incentive to keep them there but can also be a bummer for folks when they leave.
One thing I would think about if I were structuring profit sharing is to make it a pool, not a committed percentage to an individual. That’s a mistake you can make with an early employee is to say, oh, you get 1%, 2%, or 3% of profits. I would think more about, hey, let’s have a 10% profit sharing pool, and all key employees share in that, or all employees share in that.
Such that as you add more people, obviously, that first employee’s percentage of the whole chunk will go down. But ideally, the company should be growing, and these individuals should be contributing to that. If you’re going to do profit sharing, you probably want to stay away from being a C-corp because that’s going to give you double taxation, so you’re going to want to be in a pass-through entity.
Again, I mentioned Trends.vc at the top of the show, but there’s a really good report that Dru put together over there talking about the ins and outs of profit sharing. The best article I’ve ever seen written on profit sharing is from Peldi Guilizzoni. He wrote about the profit-sharing that he designed for Balsamiq. We’ll link that up in the show notes. But he basically said, they started off with a 10% pool—10% of the profits. I believe each quarter was distributed, and then he moved that to 15% at a certain point, years into the company. Now he’s up to 20%. I love that range right there. That feels really solid to me. To be honest, that 10%-15% stock option pool is also the standard size that a Silicon Valley startup would have.
That number does ring in that zone that I feel personally comfortable with. From Peldi’s article, one thing he talks about is they do quarterly distributions, which is probably what I would do if I was going to do it because if you do monthly, it’s too often. It’s just too much paperwork. If you do yearly, then people wait around and it’s bonus season. People will stay past that mark.
If they’re unhappy, they collect the profit sharing for the year, and then they take off. I don’t like that gap. It should be 3 or 6 months tops. But Peldi says, “Our quarterly bonus program allocates 20% of profits to full-time employees: 25% is split equally and 75% is split based on seniority, then it’s all weighed by the cost of living in each location.”
That’s how he structures it, and I do like that there’s a part split equally. There’s a part split by seniority. I have also heard of folks doing it based on the amount of salary people make, and then not having that cost of living of your location factor in because that’s already factored in.
One thing I would stay away from personally is using performance evaluations as some type of thing that affects profit sharing. That can be dangerous as different managers across a company might rate people differently. Basically, you should have A-players on your team, and if not, then they need to be let go in essence. If someone is performing at a subpar rate, then you need to be addressing that rather than essentially docking a bonus because there’s a lot of ways that this can backfire. Personally, I would not be including employee performance as a part of the criteria.
One drawback of profit sharing is that it’s really always taxed as income. It’s a big hit. If you’re talking about, you’re in the 33%, 35%, or 40% tax bracket, and you get a chunk every 3 months in essence, that’s a big difference versus if you were drawing out dividends. I guess through a C-corp, you’d pay double tax on it anyway. Or if you had a stock that you were able to sell, that long-term cap gains is a really big difference, and it can make a really big difference in the tax bill. But that is what it is.
Profit-sharing is cash. It’s a short-term motivator. I shouldn’t say short-term because it can motivate people over the long-term, but it really does allow employees to focus on not only growing the top line but potentially looking at reducing expenses, which the profit is obviously the revenue minus expenses.
I do think that a lot of folks in your company can impact the net profit that it has. If they’re thinking about their share of that, it does a pretty good job of aligning those incentives in a way that perhaps stock options are pretty nebulous.
Why is the stock worth more? Well, it’s typically worth more when someone buys the company or when you raise that next funding round. Is me saving $2000 a month on our AWS bill going to really impact the value of my stock options? It’s very unlikely versus profit sharing. You can see the money hit the Excel spreadsheet, the Google Doc, and you could see how it could literally trickle down to not only the company’s bottom line, but then to your own.
Some companies have folks vest into profit sharing or not be eligible for the first 6 or 12 months. I don’t think that’s unreasonable much in the same way that many companies have a waiting period to get on health insurance or to start a 401(k). This is another perk that makes sure the person’s a fit for the team, that the team is a fit for the person, and then evaluate getting them set up with all of the benefits.
These days, if I was going to evaluate these approaches for my own SaaS startup, I would think about whether I was going to be able to run it profitably. Obviously, profit sharing might be the choice then. Think about whether I was going to grow this and sell it, or have a liquidity event at some point. Then obviously, stock options might be a better opportunity.
Again, I think bonuses can be useful in the early days, but personally, they’re a little too arbitrary and can create a little bit too much chaos or just reinventing the wheel syndrome every year to personally be my favorite for having to run it long-term. And then equity, obviously, I mentioned, if it’s founder-level folks, then you can talk about that. But there are a lot of complexities there—taxable events, K-1s, and all that—that I don’t think scales to a full workforce.
Thanks again for joining me this week as I talked through different ways to incentivize your team members. If you have thoughts or comments on this episode, please give me a shout out on Twitter, @robwalling and @startupspod. I will talk to you again in your earbuds next Tuesday morning.
Episode 518 | A Live LinkedIn Ads Consult with Anthony Blatner and Scatterspoke
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Episode 518 of Startups For the Rest of Us is an experimental format where Anthony Blatner, a LinkedIn expert, live consults with John Samuelson, a B2B SaaS founder on advertising a SaaS business on LinkedIn.
There’s a wealth of knowledge in today’s episode so if you are considering or have thought about LinkedIn ads, this episode is worth a listen. We’d love your feedback on this new format. Was it helpful? Let us know in the comments or on Twitter (@startupspod)!
[BONUS] Download a LinkedIn campaign brief PDF developed during this episode
The topics we cover
[04:29] Should a B2B SaaS founder consider LinkedIn?
[07:33] Scatterspoke’s ideal customer profile
[13:12] Ideal company size for Scatterspoke
[21:16] Looking at adds other companies are running
[24:43] Putting this together into a campaign
[30:36] Audience size and example ads
[36:19] Setting a budget for ads
[22:59] Free trials on LinkedIn
Links from the show
- Episode 517 | Married Co-founders Who Turned a Free Tool Into a Fast-Growing SaaS Product
- 2021 State of Independent SaaS Survey
- Modern Media
- Scatterspoke
- Scatterspoke,Modern Media | Twitter
- Scatterspoke,Modern Media | Website
- Anthony Blatner | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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Rob: Welcome to this week’s episode of Startups for the Rest of Us. I am your host, Rob Walling. As you all know, each week on the show we cover topics related to building and growing startups using an ambitious yet sustainable approach. This is episode 518 and today is an experimental format. It’s a format I don’t believe—if I recall—we’ve never done but it’s more than 10 years, so you can’t quote me on that.
In essence, we get about 20 cold emails and pitches a week for guests and potential guests wanting to come on the show. In my memory is that we have had exactly zero of those cold pitches on this podcast. It’s just too overwhelming to go through them and frankly, most of them are so far off-topic that it’s just a sea of conversations that would not be relevant to the Startups for the Rest of Us audience.
This week may mark the first time that I’ve ever had someone on who has cold emailed. This is a LinkedIn ads expert named Anthony Blatner. In fact, he didn’t cold email. He called, LinkedIn outreached me, and the reason I was intrigued is, I like talking to specialists in their areas, so Facebook ad experts, Google ad experts, LinkedIn ad experts. Someone who really knows their space, knows how to engineer it, and do it well. I’m always intrigued by their knowledge. I started talking with Anthony a little bit. I actually listened to a couple of other podcasts that he was on and realized he knows what he’s talking about. He actually runs an agency called ModernMedia, it’s at modernmedia.io.
As I started thinking about it, I thought I could bring him on and have the same general conversation that he might have on any other podcast where I say, who do LinkedIn ads work for and how should you target them. General question number three. We could run through it and that would be a fine interview. But I started thinking, what if I brought a startup founder on the show who might be considering doing LinkedIn ads or is going to be doing LinkedIn ads soon? And had Anthony basically do a live back-and-forth conversation, almost like a real client consultation. That’s what I did.
I reached out to a few founders I know and as luck would have it, John Samuelson, a co-founder of ScatterSpoke, which is the company that I interviewed last week. I interviewed John and his wife, Colleen, about them starting ScatterSpoke, which is an online agile retrospective tool. We got to talk through their story last week and then he was available to do this. He had considered LinkedIn ads and it just seemed like it made a ton of sense to just piggyback this week’s episode with last week’s.
Today, we’re going to hear from Anthony Blatner and John Samuelson. Anthony is going to give John advice on LinkedIn ads. Not just advice, he goes through the step-by-step process that he uses to onboard clients and ask him about the roles that you want to target, to get an idea of audience size, and to get an idea what you should give them because sending them to a free trial, as Anthony says, is not usually the way to go. There’s a wealth of knowledge in today’s episode.
If you are considering or have thought about LinkedIn ads, I do think it’s well worth listening to hear Anthony’s process. This is someone who does this day in and day out with clients. He obviously lives and breathes this ecosystem and he’s focused on it. There’s just a lot of knowledge being shared on the show today.
Before we dive in, the second annual State of Independent SaaS Survey went live last week. You can head to stateofindiesaas.com to take the survey if you are a SaaS founder with at least $1 in monthly recurring revenue. We would love to hear from you. Filling out the survey not only gives back to the community because we create the 70+ page glossy report that we passed out last year, but you get the marketing bonus chapter if you complete the survey.
The survey is taking between six and eight minutes this year. We’ve streamlined it just a bit. I would really appreciate you checking it out. We already have hundreds and hundreds of responses and we’re looking to beat last year, which I believe is just shy of about 1600 responses. So, stateofindiesaas.com. With that, let’s dive into my conversation about LinkedIn ads with Anthony Blatner and John Samuelson.
Gentlemen, thank you so much for joining me on the show today.
Anthony: Hey, thanks for having me. Glad to be here.
John: Likewise.
Rob: Listeners, who tuned into last week’s episode, they already have quite a bit of background on ScatterSpoke. I think we’ll update them on that in just a second. I think I wanted to start off Anthony with a question for you for a B2B SaaS founder who might be listening to this. Who really has that high-level question of should I even consider LinkedIn? What needs to be in place for LinkedIn to potentially be a viable channel for a B2B SaaS founder?
Anthony: A couple of pieces that you want to have before you go use LinkedIn. LinkedIn’s a great channel for professional targeting, to be able to get in front of B2B companies. LinkedIn does tend to be a more expensive channel to use. You want to make sure you have your different pieces online before you go use LinkedIn and you pay those higher prices for their advertising.
A couple of things that we usually look for or recommend to use LinkedIn is, first of all, having your LTV be around 10,000 or above to start. LinkedIn’s a more expensive channel, so when your LTVs are above 10,000, then the math gets easier. If it’s below 10,000, it can still work but you’ll need to have to gather pieces of your sales process really tuned in to make sure you’re maximizing that.
The second thing you want to have is a specific target market, a specific target customer profile that you can target. Some companies out there might serve every professional or they might be for every business owner. When you have an extremely broad audience, then honestly, other channels might be cheaper and better for you. LinkedIn is awesome when you need to target a niche decision-maker at scale because that’s what LinkedIn has. It’s like those job titles, those industries, those company sizes. They just can’t get anywhere else. Having a niche ideal customer profile is important.
Thirdly, is having your sales process dialed in. Like I said, LinkedIn’s at the more expensive channel to use, it’s a great place for starting a conversation, and for a lot of people, it’s the only place you’re going to be able to go find your target customer. Because it is more expensive, you want to have your sales process tuned in. As we generate leads for you, you can then go work those leads and turn those leads into customers.
Ben: The way I thought about it is Google searches, and frankly, whatever being searched is good […] they’re about intent. It’s about someone needing to do something now. They’re searching for red Nike shoes or they’re searching for how to make a pumpkin pie. Whereas Facebook tends to be about interests. It’s more about who they are and what they’re interested in. I had thought and I have not really run LinkedIn ads before, but I had assumed that LinkedIn would be based on company type, employer size, and role, most focused on the role of the individual. Does that sound relatively accurate?
Anthony: Yeah, that is accurate. Most of our campaigns do use that company and professional targeting—what’s the role somebody has and then what type of company or industry are they in. That’s the data that nobody else has that LinkedIn does have. We always say, LinkedIn’s one of the first places people update when they change roles or change jobs. It’s usually pretty up-to-date, pretty accurate info.
There are some other targeting options outside of those that we do use that are useful to say, who do we want to target but then also what does this person interested in so that we can find those people that are a good fit and are interested in our offering.
Rob: Sounds good. Let’s dig in. John, you haven’t had much of a chance yet to speak. But folks who listened to last week’s episode already know something about ScatterSpoke. Do you want to just give the 30-second rundown of what ScatterSpoke is? Then, we’ll hand it off to Anthony to run with this
John: Absolutely. ScatterSpoke is an online agile retrospective tool. It was born out of playing around. You can get that story from last week’s episode. Essentially, it allows you to have remote distribution, or you can use in the same room, agile retrospective in some analytics and tools around it.
Anthony: Got you. I listened to a little bit of the episode and took a look at the site and all that. The one thing that I remember that you’re talking about in the last episode was your different customer segments and that you have three different tiers of those customer segments. Let’s start with that. Let’s start with talking about who your ideal target customers are, and then tell me about those three different segments that you have.
John: The baseline is the people that are in there using it, like on a team of engineers, developers, Scrum Masters, maybe product managers to some degree. Those would be on the team level of people using it. As you run up the gamut, you have engineering managers and directors of an engineer might use it.
One of our things that separates us as a tool is we have this feature called scaled retrospectives. If you’re a big company and you have 10 different teams, we can break those into, we call them programs. It’s a safe term. We’ll actually talk about that (I hope) in a few minutes. It’s a way you can roll up information from teams into a next block and then maybe the director only has to look at this program level retrospective. Those are our segments at the moment.
Anthony: Those are two good segments. One is engineers. You mentioned developers, people participating in these retrospectives, the Scrum Masters were probably running them, and then the product managers who are also involved with maybe running those meetings as well. That’s number one. And then number two would be more of the leadership around the engineering capacity. Is that right?
John: Yeah, that’s exactly right.
Anthony: Those are two good segments. Let’s start by breaking down different aspects of this audience. I’ll take some notes as we go and I’ll try to help size up the audience. One big thing when we approach LinkedIn is looking at what’s the size of the adjustable target market out there. Maybe some different things I’ll help advise on is how much to break down the audience into different segments so that we can split-test things when you launch a campaign, then at what points do we want to put together different audiences or how to mix and match those.
To start, are you guys starting in the US primarily or are you guys involved in other countries?
John: I’d say 70% of our traffic is US-based. We do have a pretty strong usage in Europe as well. I don’t know if we’re calling England in Europe anymore but a lot of people in England. I won’t really focus on them as much. The US is the bread and butter for sure. Not much for Asian countries.
Anthony: Sounds good. Knowing what I know about retrospectives and you mentioned engineering and developers, talking about industries that you commonly serve, is it largely the software development industry?
John: Almost entirely. Although one of our bigger clients is actually in oil and gas. Oil and gas company of that size, like a worldwide company. They obviously have dev teams too. I would say the majority of them are some very tech-heavy focused company, yes.
Anthony: On LinkedIn, a lot of companies in the tech, in the software space, a lot of them will categorize themselves as software companies, but then also, a lot of them categorize themselves as the industry that they serve. Just a random example, maybe there are some that are software companies, but they serve the oil and gas industry. They probably categorize themselves as that.
My follow-up question is, oil and gas can be one. Are there any other trends of industries that you see a lot of?
John: Honestly, no. It’s all over the place. From top Silicon Valley household names you would recognize, to healthcare, education. Universities have looked at us. If you have a development team—a lot of companies do now—you’re fair game. I know that’s very wide, but we haven’t really seen a very strong niche.
Anthony: Okay. Commonly, when we have an industry like this, what we’ll do is we’ll do one campaign or one split test that targets just the computer software industry, and then we’ll have one that targets everybody but the computer software industry. We can see those metrics side by side and how it’s performing.
Also wondering—just I think about it—do you ever partner or do you think it’s a possibility or good option to partner with another agile training organization out there? A lot like consulting companies that do stuff like this? Do you ever partner with those companies?
John: We’ve gone down that road a couple of times. Nothing’s really stuck. My wife who co-founded this with me, that’s how we got in the door almost everywhere. She’d be on training assignments at whatever company and be like, oh, by the way, we have this retro tool. It’s definitely a very good way for us to get in. But we haven’t had that much look at getting other consultants to do it.
Anthony: We’ll put that down as an idea, but my hunch for you guys, probably going to start with a split test of one targeting the computer software industry and then the other targeting all the other industry people so you can see those metrics side by side.
Next is talking about the size of the companies that are the best fit. I know you have different plans based on the number of users and stuff. Where do you see your sweet spot being?
John: In terms of the size of the company, this is actually something that I was hoping to pick your brain about. There’s a thing in the agile space, like a framework called SAFe. It stands for Scaled Agile Framework. It’s a very niche part of the agile industry and it’s designed for really large companies. It’s a way for you to scale your agile process from 100 dev teams or 50 dev teams, and it’s very methodical in how it all rolls up. Some of our best enterprise clients implement SAFe.
To do SAFe costs a boatload of money. But obviously, these companies are invested in agile and they’re invested in scaling their agile. One of our sweet spots for tools is this scaled concept. Most companies (I think) that are doing SAFe, they’re literally like Fortune 500 companies. They’re really big. They have 50 dev teams or something.
Anthony: Got it. That’s good to know. Somebody who’s using SAFe means that they’re probably a good prospect for you guys.
John: Absolutely, yeah.
Anthony: I’m taking a quick look here. Doesn’t look like there’s a lot of groups on LinkedIn that are about SAFe and scaled agile.
John: You would search for SAFe program consultant would be a title or role, or agile program manager. Those are key roles. If somebody has that role at a company, you know they’re deep in SAFe.
Anthony: Okay. People using scaled agile, I see there’s a lot of groups around that. That could be a good targeting to layer on top. Back to the company size factor, LinkedIn has different levels of companies you can target. As far as the number of employees that are there. What do you see as your sweet spot being is the best company size to target?
John: I think that most of our customers are probably between 50 and 200 employees. They’re not going to have huge engineering organizations at that size. They would probably be on our cheaper plans. If we’re just talking about where the most for our customers fall, it’s probably there. Our most profitable customers, though, are in thousands of employees.
Anthony: I remember in the last episode, you were talking about enterprise companies. One of those, like Fortune 500 size companies with thousands or even tens of thousands of employees?
John: Yeah. Those guys, when they buy licenses, they’re buying between 1000 and 3000 user licenses.
Anthony: We’ll break down both of those in a second. Next is getting into some of the job titles that we could target. On LinkedIn, we can either do job functions or we could do job titles. Under functions, for example, we have project management functions. The two that I think would be good for you are program and project management and then product management. Those people probably have people who are running projects, probably managing this process. But as far as specific job titles go, you mentioned the SAFe consultant as one. What would be some other job titles that’d be a good fit?
John: In the SAFe role, there’s (I will say) a release train engineer. That’s a very SAFe-specific thing. I had mentioned agile program managers. Those are the really SAFe-heavy things within SAFe or within any of this industry though, I mean software engineer. On the product side, I’m not sure as much. Oftentimes, smaller companies’ product managers often double as a Scrum Master. That could work, but I won’t favor that side. If you’re a company and you have someone that’s a dedicated Scrum Master, you probably care about agile, so you probably would care about us.
Anthony: Yes. I do see, there’s a Scrum Master title on LinkedIn. We can definitely target that. Product, people are likely good, but they might not always be the ones managing this process?
John: Yeah. In general, they might not be inside of engineering. I would do an engineering manager over a product manager just because I think they’re closer to the team that’s actually using our tool.
Anthony: Okay. There is an engineering function on LinkedIn. That could be another broad category to use. How about what are some other titles that are maybe specific to this process or to agile that you commonly see?
John: Agile coach, again, Scrum Master, you could be Kanban, insert something afterward. I don’t know if you can look for certifications on LinkedIn. Is that something you can target?
Anthony: There are skills, which often do match up as certifications.
John: Even developers oftentimes will take a Scrum class or some kind of agile training class and they put it on there. That’s the little gamut there. I’d say, software engineers, engineering managers, Scrum masters, agile coaches, those are definitely the bread and butter of the people that are actually using it often.
Anthony: Okay. As far as the two segments here, it sounds like one is like the engineers themselves. They are a good candidate because they’re in the process, and then the other would be like the managers of that process. About how far up the chain would you want to go?
John: This is a question I would have for you. In terms of purchasing power, most software engineers are not the person that can swipe the credit card. Engineering managers can, but we see it sometimes usually goes up to directors of engineering that are usually like, yup, I approve because they’re usually on a budget. Up above that, I don’t think it makes sense. I don’t think I would target anything with a C in front of it. But vice president of engineering, director of engineering, that’s probably as high as I go in the engineering segment.
Anthony: Next is talking about maybe more of those certifications and those different skills that people could have. I did find a number of them on LinkedIn beforehand. Before I dive into what I already found, tell me a little bit about what are some of those certifications?
John: Scrum Master is the big one, there’s a Kanban certification, there’s a SAFe certification. Those are very targeted types of skills that you can get certified and a lot of companies will pay for their employees to get them.
Anthony: Got it. I do see the scaled agile skill there. Some other ones I see that I found are related to agile, sprint planning as one, Scrum, there is one for retros and retrospectives. People who are doing that at their jobs are probably listing down in their profile. Another question is the different software that you guys integrate with. I think I saw a couple of project management systems. What tools do you guys work alongside?
John: We have integrations, Atlassian, Jira, Trello. Those are the currently active project management tools. If you’re using something like Asana or Rally is really big at big companies. If you’re doing that using those tools, likely you’re doing agile, likely you care about retrospectives.
Anthony: Got it. Those tools are also good candidates if you are using Asana and Rally.
John: Honestly, anything that’s a developer toolchain set as well. That’s actually on our road map to add some of the integrations with GitHub, GitLab. I would rank those slightly lower than the project management stuff, but those definitely work as well.
Anthony: We can even add different groupings of these together. We can do people who have these agile skills, maybe it’s the SAFe framework certification and they have agile skills. Then also, we end that with the tools that they’re using—Jira, Slack, or Trello. And then we’re getting closer to the people who are the best fit for you guys. People who are experienced in agile, who are doing agile, and also using the tools you integrate with, those are probably the best ones to target.
John: Yup, that makes sense.
Anthony: One thing that we can do out there is look out what ads other people are running. Here’s a little tip. If you go to any LinkedIn page—they actually just moved this button—go to the home section and you scroll down just a little bit to see their newsfeed. There’s a little button that says posts and like different things that they could be posting, and then there’s an ads button next to it. If you click on that, you can see the ads being run by any page.
One thing that we do a lot is go look at competitors in any market and see what ads that their competitors are running, it’s usually a good place to get inspiration to see if there are any trends that you see in their ads, what’s the offer, what are they promoting, what’s the angles that they’re taking, and then what’s the imagery that they’re using. And some of these tools you integrate with could be good prospects to just go check other ads too.
Who would you say are some competitors or similar offerings out there in the market?
John: The big one that comes to mind is a company called Retrium. They do a lot of ad spend marketing on Google. I’ve never seen them on LinkedIn, but they could be on there. Another one would be Parable. To be honest with you, there’s not really a lot of other ones. Those are probably the two bigger ones. That’s not true. Things like Miro, which are huge, have tried to do little niche side products off their main product. I don’t think they would be spending money on advertising for retros. That’s what comes to mind.
Anthony: I’m looking at Retrium right now. It looks like they have a webinar about anti-patterns and then a lot of their ads are also around as a free trial to sign up to get started. It’s also a good sign when you see your competitors using ads on LinkedIn. That could be an indicator that they’re having success with it.
One thing, general LinkedIn recommendation, is you do see a lot of people out there that will advertise directly for a free trial, schedule now, or sign up now. On LinkedIn, you’re usually paying for every click. As soon as somebody clicks on your ad, you’ve paid for that click whether they sign up or not. We generally see that those are lower converting offers because they’re very direct. Someone needs to know enough about you to be willing to sign up. We see that those offers can be a lot more expensive to get people to sign up for.
Usually, what we do is use a content-focused offer to get somebody to sign up. That starts the conversation, then they’re in your sales or marketing funnel, and then you continue to nurture them from there. Maybe you reach out to them afterward and schedule a meeting. Most of our campaigns on LinkedIn tend to be content-focused, but there’s a lot of strategy around what that piece of content is. You want to (in a way) qualify your prospect a little bit. If they’re signing up for this piece of content, then they’re interested in what it is that you do.
Different things that work well are stuff like blogs, turning them into PDFs, white papers, checklists, stuff like that. I saw you have a good amount of content on your website. I’m wondering, what are the best pieces of content that you guys have and if any of those blog posts are getting a lot of traffic. Wondering about the content that you guys have.
John: Narrowing back to the SAFe thing, SAFe is all about scaling agile. If we can show them content around how we can scale your retrospectives, I think that’s awesome synergy for them. We’re about to release all-new marketing material. When we have a page dedicated to scaling retrospectives and also scaled analytics, that’s what comes to my mind right away.
Anthony: We’re getting a lot of the pieces here. Now, we’re going to start putting this together into what a campaign can look like. Next is thinking about what the funnel is. There’s somebody that’s going to go on to become a customer of yours. I’ve seen your website and it looks like they can sign up right there. What else I see is there’s a schedule a demo button. When somebody signs up on your website or if you ever have somebody reach out to you and say they’re interested, tell me a little bit about what your sales process looks like.
John: To be honest with you, we are just starting to really come up with our marketing and sales process. Traditionally, it looks like they come to our site, they may be play around with it, they have questions, they book a demo or they chat with us through Intercom or write on our support tickets. We handle it from there. When we release all these new marketing stuff, it’s going to be maybe more traditional. If we already use the scaled stuff content as an example, we’d have a special landing page for scaled. You can put in an email address to learn more about scaled agile retrospectives.
Honestly, hopefully, they’ll sign up. Actually, I think Rob might kill me because we talked about this a long time ago. Our schedule a demo button still goes directly to us without qualifying them, really. It hasn’t been that crazy of a problem. I would either want their email address or for them to schedule a demo as a goal (I guess) from an ad, but I don’t have enough experience with these types of marketing ad funnels to really speak beyond that. That’s what I think would be a goal.
Anthony: Right now, if somebody hits schedule a demo, then they get in touch with you. You guys get on that call, have a quick demo. If they’re interested they sign up from there?
John: Yeah. That’s exactly right.
Anthony: Okay. Sounds good. Next is starting to put some of these pieces together. As I said, if you go direct without scheduling a demo on LinkedIn, most people out there haven’t heard about you. Most companies in general out there, if you’re not a mainstream company or a well-known brand, people haven’t heard about you. If you put schedule a demo in that first ad, people just don’t know enough to be qualified to sign up. Someone might submit that form but might not really know exactly what you do, could be a little confused, or they think of something else.
We see that people that sign up for that usually, it’s a much lower conversion rate. You’re paying a lot more for each lead. The leads that you get usually aren’t great because they just don’t know enough yet. Going content-focused, content first, the more educational route, using these lead magnets is a good way to get people to sign up and positioning it so it qualifies the person as they sign up.
When you use LinkedIn’s targeting so that these are good leads that are coming through because they are only targeting companies up to a certain size, people with these specific job titles, and then positioning the content as something for SAFe would be a great piece of content to have.
There are different levels of content and usually, we see that white papers, guides, and checklists often do the best. Quick and easy downloadables, something that someone can learn something about you. We see that quick and easy downloadables get the highest conversion rate because somebody can download it quickly, read it, and learn a little bit about you. You started the conversation with them and then you can reach out to them afterward via email to set up that follow-up call.
Not everyone will take that step, not right away, but part of the sales process that I mentioned having honed in is you want to have some kind of follow-up email sequence out there, some Drip campaign that when somebody signs up and says they’re interested, and they’ve downloaded the piece of content. Maybe you have a weekly email or a monthly email that goes out, maybe with more content about SAFe, you can alternate videos of your platform or information about your platform, and then you can include little offers in there, too. Like here’s the next step, schedule a demo, or start for free—I see you have here—so having that follow-up sales process is important. Thinking about what that content offer is going to be, yeah, I think something like SAFe could be a good piece of content.
John: I have actually another question around that. If we have an ad and we say, here’s this great piece of content, come and download it. That takes them to a landing page of ours where they can do that. Is the entire goal for them to download or do whatever that content thing is, should we not even put a sign-up now button somewhere on there that’s like a different call to action? Or do you focus to just get them the content right then and then nurture them through email?
Anthony: Good question. Yes. In the funnel, you do want to offer them that next step or at least show them what that next step is going to be. The first goal is yes, get them to that landing page, that they can download the content and read it. Them reading that content is what warms them up to your brand. They see your logo, but more importantly, they learn about ScatterSpoke and they learn what it is you do. At the end of your PDF, you might have a little blurb about ScatterSpoke and click here to learn more. But on that landing page, you want them to learn a little bit, you want them to read that lead magnet, and then usually, maybe lower on the page, maybe on the side there, we’ll have a little button and then indicate like, hey, if you’re interested in getting ScatterSpoke to help you with this problem, to help you with scaled agile, then click here to schedule that demo.
Oftentimes in our funnels, there’s a lot of tools out there that are like scheduling widgets you can use and you can embed those right in your landing pages. Maybe somebody clicks that button and they said, okay, I am interested to learn more, or I want to try this tool out. I’m going to sign up for this scaled agile stuff and they click that button, it can go on to book a call with you.
John: Got you. That makes sense. You can do both, but the primary focus should probably be on the content, that you can still try to lure them further down the funnel.
Anthony: Yeah. Them consuming that content is what is going to educate them and warm them up to your brand. You do have a competitor out there. If they didn’t read that PDF, then they don’t know what makes you different from Retrium. Them reading your scaled agile piece of content in your lead magnet, you’ll want to teach them something, but then also weave in how ScatterSpoke helps you achieve that goal. Through them reading that, they’ve learned more and they know more about ScatterSpoke.
John: Makes sense.
Anthony: Next is talking about what some of the ads could look like. I have a couple of audience sizes here based on the different titles and stuff you’ve given me. If we were targeting the computer software industry and if we were targeting engineering and project management type of roles—C or the VP levels—and using these different skills, it looks like that’s about 20,000–30,000 people in that audience, maybe bigger, maybe smaller if we add or remove some of these piece of skills that we talked about. But that’s what we want to see is we want to see at least 20,000 people in that audience. That might not sound huge, but that’s still a lot of people out there.
If you use an audience that’s smaller than that on LinkedIn, you might just have some deliverability issues, trouble getting in front of people, but having a 20,000–30,000 audience is a good size. If you go on LinkedIn and you have a massive audience of a million people, then you want to start segmenting that down into different sub-audiences that you can split test.
For the other side of things, if we were to target other industries outside of computer software, that’s a lot of industries out there. Looks like that audience is about 60,000–80,000 people. This one is taking all those agile skills and then also ending that with a different tool that it could be using. This is probably a pretty good audience for you, too.
That’s the first thing we want to look at is what’s the size of the audience that we can be targeting on LinkedIn. Our usual target is somewhere between 20,000–80,000 people. If it’s under 20,000 that might be a little small. If it’s over 80,000 people, then usually we have the opportunity to get more targeted in it.
Next is talking about what some of these ads could look like. If we were doing a scaled agile framework PDF, the question for you is what are some of the main pain points that one of these Scrum Masters has approaching scaled agile.
John: What we’re trying to do in our tool is oftentimes teams will complain about the same thing for months and months and months, and it doesn’t really ever leave the team. One of the things we’re trying to solve with this scaled idea is to elevate them to more leaders in the company. What we’re trying to solve and the pain point specifically is to get things off the team level and into a leadership level in a formal process or […] way so that they know what’s happening on the teams. Otherwise, they’d often get lost and it just remains as the problem for long periods of time.
Anthony: Got it. The problem there is that things are getting lost?
John: Yeah, or they’re just never solving the problem. They’re just like, oh, it’s out of our control. We can’t change some fundamental company things so we should just never tell anybody about it. But I think leaders often do want to know about that stuff still. If they don’t feel like there’s a way to talk to the senior leaders in a company, then they’re never going to tell them. We’re offering in a way to make a tidy inbox of problems and concerns from teams up to higher-up leaders at a company.
Anthony: Okay. The last piece here is what some of your ad copy could look like. Maybe, you’d say for your scaled agile PDF here, your ad copy to the engineers, maybe you’d say, having trouble submitting your retrospective feedback? Download this scaled agile guide to learn how to better manage your retrospectives for your company.
We also find like throwing stats in there can also be really powerful. I saw in your website, there’s mentioning about wasting time, stuff like that. Different angles you could take is are you wasting time in retrospectives and not getting anything done? Are you having trouble getting in touch with higher leadership? And then throwing in the stat saying, the average sprint team wasted 30 hours. Download this ultimate guide to scaled agile to learn more.
Somebody who signs up for that using our LinkedIn targeting, we can know that these are engineers using these tools […] agile and likely having this problem or interested in the solution that you have. That’s probably a good candidate for you. Just an example of some plausible ad copy.
Maybe another cool thing I could probably do after is send this over to you, maybe package it all up, send it over, maybe put together an image or two, what it could look like along with some of the audience targeting stuff that we talked about, put it on a package and then send it over. That might be a good wrap up of everything that we talked about.
John: Yeah. The examples you just gave are spot on and would totally work. We pretty much narrowed it down to what would get these SAFe guys moving, honestly. They’ll love all this stuff. I’m actually curious, though. Two things that we’re talking about along the way. We have one audience size of 20,000 or 30,000 people. One audience size that was much bigger, like 80,000 people. Who should I spend money on first?
Anthony: That question I’ll turn back to you. I would turn back to you and ask who’s the more important prospect for you?
John: I think it’s hard to know who’s going to pull out the credit card at the end of the day. I guess, is there a way to say, I want to spend 60% of the budget on that group and 40% of the budget on that group on LinkedIn?
Anthony: Yup. What we would do is set up separate campaigns to split test them and then each campaign is its own audience. We’d basically split test your audiences and then you allocate a specific budget to each campaign so we could do it. Yeah, we can do 60% to one audience and then 40% to another. Usually, when we launch campaigns, we always have at least two audiences. We have a measuring stick so that we can compare them. The different levels of split test we usually set up are at least two audiences, at least two lead magnets, and then several ads for them.
John: Probably a lot of companies in my position would want to know this. Everything we just talked about, what’s the right size budget to think about? If you go to an ad company (and I have) then you’re like, what should we start with? Well, you should do a $5000 minimum. Other people have said, you can probably get early results for $500–$1000. How should we think about setting a budget for something like this?
Anthony: LinkedIn is a more expensive channel. I usually recommend the minimum for each campaign is about $2000, and then the minimum amount per campaign level is about $1000. Then you can be sure you’re getting at least enough clicks in that you’re getting enough data to make a decision based off of. For here, if we were doing these two audiences for you, I’d recommend $1000 over a month period for each audience and then $2000 total.
John: Okay, got you. We’re a small, mostly bootstrap company. Obviously, these things are really important to us. What’s a normal clickthrough rate, just to put in perspective?
Anthony: Normal clickthrough rate, the LinkedIn average is about 0.4. Anything above that and your ads will actually benefit going in the auction. You’ll get cheaper ad costs. 0.4 is actually relatively low. We like to say you want to shoot for usually around like a 0.75 or so. That’s a good CTR that we look for.
At the end of the day, we don’t look at CTR a ton because on LinkedIn you’re usually paying for every click. Whether or not something clicks, you only pay when somebody clicks. Having a little CTR rate doesn’t usually hurt you unless you’re below that 0.4 level. We don’t look at CTR a ton, but we look at what’s the CPC that you’re paying.
John: Right, but it just helps me ballpark. I can take the number of people that might view it, just start to do basic math, and maybe estimate what CPC would look like. Okay, that’s all really, really handy. This has been awesome.
Rob: Anthony, if you do want to package that up and send it over, I might love to pull maybe just a couple of pieces out of it, put it in either our show notes directly, or maybe as a PDF people can download. Just hearing it all on the show is super informative, but then being able to even see what you’re talking about could be helpful for listeners too.
Anthony: Yeah, definitely. I’ve been trying to do my best to articulate the different job titles and copy and stuff, but it’s totally different seeing it done in writing.
Rob: I know. To call out for the listeners, you would ask, can we do a screen share. I know that would be ideal, but it’s just so many of our listeners are going to be audio-only that I felt like it would leave a lot of people out. If they need that visual element, we’ll be sure to include that in the show notes.
If you would like to keep up with Anthony, you can head to modernmedia.io, or head to LinkedIn where he has a prominent profile—more than 500 connections. I was going to make a joke and say, and Anthony has no LinkedIn profile.
Anthony: That would be funny, though.
Rob: I don’t know if people might have a dry sense of humor, maybe. Wouldn’t have worked. John as well, you are @scatterspoke on Twitter. Gentlemen, thank you so much for joining me today.
Anthony: It was fun. Thanks for having me.
John: That’s right.
Rob: Thanks again to Anthony and John for joining me on the show today. Again, check out stateofindiesaas.com if you are a SaaS founder and are willing to provide anonymized data to really help educate us all on this whole independent SaaS movement. The non-venture track bootstrap or mostly bootstrapped SaaS founders the more data we can get, the more knowledge that we have and can share with one another. Thanks so much for listening and I will see you again next Tuesday morning.
In essence, we get about 20 cold emails and pitches a week for guests and potential guests wanting to come on the show. In my memory is that we have had exactly zero of those cold pitches on this podcast. It’s just too overwhelming to go through them and frankly, most of them are so far off-topic that it’s just a sea of conversations that would not be relevant to the Startups for the Rest of Us audience.
This week may mark the first time that I’ve ever had someone on who has cold emailed. This is a LinkedIn ads expert named Anthony Blatner. In fact, he didn’t cold email. He called, LinkedIn outreached me, and the reason I was intrigued is, I like talking to specialists in their areas, so Facebook ad experts, Google ad experts, LinkedIn ad experts. Someone who really knows their space, knows how to engineer it, and do it well. I’m always intrigued by their knowledge. I started talking with Anthony a little bit. I actually listened to a couple of other podcasts that he was on and realized he knows what he’s talking about. He actually runs an agency called ModernMedia, it’s at modernmedia.io.
As I started thinking about it, I thought I could bring him on and have the same general conversation that he might have on any other podcast where I say, who do LinkedIn ads work for and how should you target them. General question number three. We could run through it and that would be a fine interview. But I started thinking, what if I brought a startup founder on the show who might be considering doing LinkedIn ads or is going to be doing LinkedIn ads soon? And had Anthony basically do a live back-and-forth conversation, almost like a real client consultation. That’s what I did.
I reached out to a few founders I know and as luck would have it, John Samuelson, a co-founder of ScatterSpoke, which is the company that I interviewed last week. I interviewed John and his wife, Colleen, about them starting ScatterSpoke, which is an online agile retrospective tool. We got to talk through their story last week and then he was available to do this. He had considered LinkedIn ads and it just seemed like it made a ton of sense to just piggyback this week’s episode with last week’s.
Today, we’re going to hear from Anthony Blatner and John Samuelson. Anthony is going to give John advice on LinkedIn ads. Not just advice, he goes through the step-by-step process that he uses to onboard clients and ask him about the roles that you want to target, to get an idea of audience size, and to get an idea what you should give them because sending them to a free trial, as Anthony says, is not usually the way to go. There’s a wealth of knowledge in today’s episode.
If you are considering or have thought about LinkedIn ads, I do think it’s well worth listening to hear Anthony’s process. This is someone who does this day in and day out with clients. He obviously lives and breathes this ecosystem and he’s focused on it. There’s just a lot of knowledge being shared on the show today.
Before we dive in, the second annual State of Independent SaaS Survey went live last week. You can head to stateofindiesaas.com to take the survey if you are a SaaS founder with at least $1 in monthly recurring revenue. We would love to hear from you. Filling out the survey not only gives back to the community because we create the 70+ page glossy report that we passed out last year, but you get the marketing bonus chapter if you complete the survey.
The survey is taking between six and eight minutes this year. We’ve streamlined it just a bit. I would really appreciate you checking it out. We already have hundreds and hundreds of responses and we’re looking to beat last year, which I believe is just shy of about 1600 responses. So, stateofindiesaas.com. With that, let’s dive into my conversation about LinkedIn ads with Anthony Blatner and John Samuelson.
Gentlemen, thank you so much for joining me on the show today.
Anthony: Hey, thanks for having me. Glad to be here.
John: Likewise.
Rob: Listeners, who tuned into last week’s episode, they already have quite a bit of background on ScatterSpoke. I think we’ll update them on that in just a second. I think I wanted to start off Anthony with a question for you for a B2B SaaS founder who might be listening to this. Who really has that high-level question of should I even consider LinkedIn? What needs to be in place for LinkedIn to potentially be a viable channel for a B2B SaaS founder?
Anthony: A couple of pieces that you want to have before you go use LinkedIn. LinkedIn’s a great channel for professional targeting, to be able to get in front of B2B companies. LinkedIn does tend to be a more expensive channel to use. You want to make sure you have your different pieces online before you go use LinkedIn and you pay those higher prices for their advertising.
A couple of things that we usually look for or recommend to use LinkedIn is, first of all, having your LTV be around 10,000 or above to start. LinkedIn’s a more expensive channel, so when your LTVs are above 10,000, then the math gets easier. If it’s below 10,000, it can still work but you’ll need to have to gather pieces of your sales process really tuned in to make sure you’re maximizing that.
The second thing you want to have is a specific target market, a specific target customer profile that you can target. Some companies out there might serve every professional or they might be for every business owner. When you have an extremely broad audience, then honestly, other channels might be cheaper and better for you. LinkedIn is awesome when you need to target a niche decision-maker at scale because that’s what LinkedIn has. It’s like those job titles, those industries, those company sizes. They just can’t get anywhere else. Having a niche ideal customer profile is important.
Thirdly, is having your sales process dialed in. Like I said, LinkedIn’s at the more expensive channel to use, it’s a great place for starting a conversation, and for a lot of people, it’s the only place you’re going to be able to go find your target customer. Because it is more expensive, you want to have your sales process tuned in. As we generate leads for you, you can then go work those leads and turn those leads into customers.
Ben: The way I thought about it is Google searches, and frankly, whatever being searched is good […] they’re about intent. It’s about someone needing to do something now. They’re searching for red Nike shoes or they’re searching for how to make a pumpkin pie. Whereas Facebook tends to be about interests. It’s more about who they are and what they’re interested in. I had thought and I have not really run LinkedIn ads before, but I had assumed that LinkedIn would be based on company type, employer size, and role, most focused on the role of the individual. Does that sound relatively accurate?
Anthony: Yeah, that is accurate. Most of our campaigns do use that company and professional targeting—what’s the role somebody has and then what type of company or industry are they in. That’s the data that nobody else has that LinkedIn does have. We always say, LinkedIn’s one of the first places people update when they change roles or change jobs. It’s usually pretty up-to-date, pretty accurate info.
There are some other targeting options outside of those that we do use that are useful to say, who do we want to target but then also what does this person interested in so that we can find those people that are a good fit and are interested in our offering.
Rob: Sounds good. Let’s dig in. John, you haven’t had much of a chance yet to speak. But folks who listened to last week’s episode already know something about ScatterSpoke. Do you want to just give the 30-second rundown of what ScatterSpoke is? Then, we’ll hand it off to Anthony to run with this
John: Absolutely. ScatterSpoke is an online agile retrospective tool. It was born out of playing around. You can get that story from last week’s episode. Essentially, it allows you to have remote distribution, or you can use in the same room, agile retrospective in some analytics and tools around it.
Anthony: Got you. I listened to a little bit of the episode and took a look at the site and all that. The one thing that I remember that you’re talking about in the last episode was your different customer segments and that you have three different tiers of those customer segments. Let’s start with that. Let’s start with talking about who your ideal target customers are, and then tell me about those three different segments that you have.
John: The baseline is the people that are in there using it, like on a team of engineers, developers, Scrum Masters, maybe product managers to some degree. Those would be on the team level of people using it. As you run up the gamut, you have engineering managers and directors of an engineer might use it.
One of our things that separates us as a tool is we have this feature called scaled retrospectives. If you’re a big company and you have 10 different teams, we can break those into, we call them programs. It’s a safe term. We’ll actually talk about that (I hope) in a few minutes. It’s a way you can roll up information from teams into a next block and then maybe the director only has to look at this program level retrospective. Those are our segments at the moment.
Anthony: Those are two good segments. One is engineers. You mentioned developers, people participating in these retrospectives, the Scrum Masters were probably running them, and then the product managers who are also involved with maybe running those meetings as well. That’s number one. And then number two would be more of the leadership around the engineering capacity. Is that right?
John: Yeah, that’s exactly right.
Anthony: Those are two good segments. Let’s start by breaking down different aspects of this audience. I’ll take some notes as we go and I’ll try to help size up the audience. One big thing when we approach LinkedIn is looking at what’s the size of the adjustable target market out there. Maybe some different things I’ll help advise on is how much to break down the audience into different segments so that we can split-test things when you launch a campaign, then at what points do we want to put together different audiences or how to mix and match those.
To start, are you guys starting in the US primarily or are you guys involved in other countries?
John: I’d say 70% of our traffic is US-based. We do have a pretty strong usage in Europe as well. I don’t know if we’re calling England in Europe anymore but a lot of people in England. I won’t really focus on them as much. The US is the bread and butter for sure. Not much for Asian countries.
Anthony: Sounds good. Knowing what I know about retrospectives and you mentioned engineering and developers, talking about industries that you commonly serve, is it largely the software development industry?
John: Almost entirely. Although one of our bigger clients is actually in oil and gas. Oil and gas company of that size, like a worldwide company. They obviously have dev teams too. I would say the majority of them are some very tech-heavy focused company, yes.
Anthony: On LinkedIn, a lot of companies in the tech, in the software space, a lot of them will categorize themselves as software companies, but then also, a lot of them categorize themselves as the industry that they serve. Just a random example, maybe there are some that are software companies, but they serve the oil and gas industry. They probably categorize themselves as that.
My follow-up question is, oil and gas can be one. Are there any other trends of industries that you see a lot of?
John: Honestly, no. It’s all over the place. From top Silicon Valley household names you would recognize, to healthcare, education. Universities have looked at us. If you have a development team—a lot of companies do now—you’re fair game. I know that’s very wide, but we haven’t really seen a very strong niche.
Anthony: Okay. Commonly, when we have an industry like this, what we’ll do is we’ll do one campaign or one split test that targets just the computer software industry, and then we’ll have one that targets everybody but the computer software industry. We can see those metrics side by side and how it’s performing.
Also wondering—just I think about it—do you ever partner or do you think it’s a possibility or good option to partner with another agile training organization out there? A lot like consulting companies that do stuff like this? Do you ever partner with those companies?
John: We’ve gone down that road a couple of times. Nothing’s really stuck. My wife who co-founded this with me, that’s how we got in the door almost everywhere. She’d be on training assignments at whatever company and be like, oh, by the way, we have this retro tool. It’s definitely a very good way for us to get in. But we haven’t had that much look at getting other consultants to do it.
Anthony: We’ll put that down as an idea, but my hunch for you guys, probably going to start with a split test of one targeting the computer software industry and then the other targeting all the other industry people so you can see those metrics side by side.
Next is talking about the size of the companies that are the best fit. I know you have different plans based on the number of users and stuff. Where do you see your sweet spot being?
John: In terms of the size of the company, this is actually something that I was hoping to pick your brain about. There’s a thing in the agile space, like a framework called SAFe. It stands for Scaled Agile Framework. It’s a very niche part of the agile industry and it’s designed for really large companies. It’s a way for you to scale your agile process from 100 dev teams or 50 dev teams, and it’s very methodical in how it all rolls up. Some of our best enterprise clients implement SAFe.
To do SAFe costs a boatload of money. But obviously, these companies are invested in agile and they’re invested in scaling their agile. One of our sweet spots for tools is this scaled concept. Most companies (I think) that are doing SAFe, they’re literally like Fortune 500 companies. They’re really big. They have 50 dev teams or something.
Anthony: Got it. That’s good to know. Somebody who’s using SAFe means that they’re probably a good prospect for you guys.
John: Absolutely, yeah.
Anthony: I’m taking a quick look here. Doesn’t look like there’s a lot of groups on LinkedIn that are about SAFe and scaled agile.
John: You would search for SAFe program consultant would be a title or role, or agile program manager. Those are key roles. If somebody has that role at a company, you know they’re deep in SAFe.
Anthony: Okay. People using scaled agile, I see there’s a lot of groups around that. That could be a good targeting to layer on top. Back to the company size factor, LinkedIn has different levels of companies you can target. As far as the number of employees that are there. What do you see as your sweet spot being is the best company size to target?
John: I think that most of our customers are probably between 50 and 200 employees. They’re not going to have huge engineering organizations at that size. They would probably be on our cheaper plans. If we’re just talking about where the most for our customers fall, it’s probably there. Our most profitable customers, though, are in thousands of employees.
Anthony: I remember in the last episode, you were talking about enterprise companies. One of those, like Fortune 500 size companies with thousands or even tens of thousands of employees?
John: Yeah. Those guys, when they buy licenses, they’re buying between 1000 and 3000 user licenses.
Anthony: We’ll break down both of those in a second. Next is getting into some of the job titles that we could target. On LinkedIn, we can either do job functions or we could do job titles. Under functions, for example, we have project management functions. The two that I think would be good for you are program and project management and then product management. Those people probably have people who are running projects, probably managing this process. But as far as specific job titles go, you mentioned the SAFe consultant as one. What would be some other job titles that’d be a good fit?
John: In the SAFe role, there’s (I will say) a release train engineer. That’s a very SAFe-specific thing. I had mentioned agile program managers. Those are the really SAFe-heavy things within SAFe or within any of this industry though, I mean software engineer. On the product side, I’m not sure as much. Oftentimes, smaller companies’ product managers often double as a Scrum Master. That could work, but I won’t favor that side. If you’re a company and you have someone that’s a dedicated Scrum Master, you probably care about agile, so you probably would care about us.
Anthony: Yes. I do see, there’s a Scrum Master title on LinkedIn. We can definitely target that. Product, people are likely good, but they might not always be the ones managing this process?
John: Yeah. In general, they might not be inside of engineering. I would do an engineering manager over a product manager just because I think they’re closer to the team that’s actually using our tool.
Anthony: Okay. There is an engineering function on LinkedIn. That could be another broad category to use. How about what are some other titles that are maybe specific to this process or to agile that you commonly see?
John: Agile coach, again, Scrum Master, you could be Kanban, insert something afterward. I don’t know if you can look for certifications on LinkedIn. Is that something you can target?
Anthony: There are skills, which often do match up as certifications.
John: Even developers oftentimes will take a Scrum class or some kind of agile training class and they put it on there. That’s the little gamut there. I’d say, software engineers, engineering managers, Scrum masters, agile coaches, those are definitely the bread and butter of the people that are actually using it often.
Anthony: Okay. As far as the two segments here, it sounds like one is like the engineers themselves. They are a good candidate because they’re in the process, and then the other would be like the managers of that process. About how far up the chain would you want to go?
John: This is a question I would have for you. In terms of purchasing power, most software engineers are not the person that can swipe the credit card. Engineering managers can, but we see it sometimes usually goes up to directors of engineering that are usually like, yup, I approve because they’re usually on a budget. Up above that, I don’t think it makes sense. I don’t think I would target anything with a C in front of it. But vice president of engineering, director of engineering, that’s probably as high as I go in the engineering segment.
Anthony: Next is talking about maybe more of those certifications and those different skills that people could have. I did find a number of them on LinkedIn beforehand. Before I dive into what I already found, tell me a little bit about what are some of those certifications?
John: Scrum Master is the big one, there’s a Kanban certification, there’s a SAFe certification. Those are very targeted types of skills that you can get certified and a lot of companies will pay for their employees to get them.
Anthony: Got it. I do see the scaled agile skill there. Some other ones I see that I found are related to agile, sprint planning as one, Scrum, there is one for retros and retrospectives. People who are doing that at their jobs are probably listing down in their profile. Another question is the different software that you guys integrate with. I think I saw a couple of project management systems. What tools do you guys work alongside?
John: We have integrations, Atlassian, Jira, Trello. Those are the currently active project management tools. If you’re using something like Asana or Rally is really big at big companies. If you’re doing that using those tools, likely you’re doing agile, likely you care about retrospectives.
Anthony: Got it. Those tools are also good candidates if you are using Asana and Rally.
John: Honestly, anything that’s a developer toolchain set as well. That’s actually on our road map to add some of the integrations with GitHub, GitLab. I would rank those slightly lower than the project management stuff, but those definitely work as well.
Anthony: We can even add different groupings of these together. We can do people who have these agile skills, maybe it’s the SAFe framework certification and they have agile skills. Then also, we end that with the tools that they’re using—Jira, Slack, or Trello. And then we’re getting closer to the people who are the best fit for you guys. People who are experienced in agile, who are doing agile, and also using the tools you integrate with, those are probably the best ones to target.
John: Yup, that makes sense.
Anthony: One thing that we can do out there is look out what ads other people are running. Here’s a little tip. If you go to any LinkedIn page—they actually just moved this button—go to the home section and you scroll down just a little bit to see their newsfeed. There’s a little button that says posts and like different things that they could be posting, and then there’s an ads button next to it. If you click on that, you can see the ads being run by any page.
One thing that we do a lot is go look at competitors in any market and see what ads that their competitors are running, it’s usually a good place to get inspiration to see if there are any trends that you see in their ads, what’s the offer, what are they promoting, what’s the angles that they’re taking, and then what’s the imagery that they’re using. And some of these tools you integrate with could be good prospects to just go check other ads too.
Who would you say are some competitors or similar offerings out there in the market?
John: The big one that comes to mind is a company called Retrium. They do a lot of ad spend marketing on Google. I’ve never seen them on LinkedIn, but they could be on there. Another one would be Parable. To be honest with you, there’s not really a lot of other ones. Those are probably the two bigger ones. That’s not true. Things like Miro, which are huge, have tried to do little niche side products off their main product. I don’t think they would be spending money on advertising for retros. That’s what comes to mind.
Anthony: I’m looking at Retrium right now. It looks like they have a webinar about anti-patterns and then a lot of their ads are also around as a free trial to sign up to get started. It’s also a good sign when you see your competitors using ads on LinkedIn. That could be an indicator that they’re having success with it.
One thing, general LinkedIn recommendation, is you do see a lot of people out there that will advertise directly for a free trial, schedule now, or sign up now. On LinkedIn, you’re usually paying for every click. As soon as somebody clicks on your ad, you’ve paid for that click whether they sign up or not. We generally see that those are lower converting offers because they’re very direct. Someone needs to know enough about you to be willing to sign up. We see that those offers can be a lot more expensive to get people to sign up for.
Usually, what we do is use a content-focused offer to get somebody to sign up. That starts the conversation, then they’re in your sales or marketing funnel, and then you continue to nurture them from there. Maybe you reach out to them afterward and schedule a meeting. Most of our campaigns on LinkedIn tend to be content-focused, but there’s a lot of strategy around what that piece of content is. You want to (in a way) qualify your prospect a little bit. If they’re signing up for this piece of content, then they’re interested in what it is that you do.
Different things that work well are stuff like blogs, turning them into PDFs, white papers, checklists, stuff like that. I saw you have a good amount of content on your website. I’m wondering, what are the best pieces of content that you guys have and if any of those blog posts are getting a lot of traffic. Wondering about the content that you guys have.
John: Narrowing back to the SAFe thing, SAFe is all about scaling agile. If we can show them content around how we can scale your retrospectives, I think that’s awesome synergy for them. We’re about to release all-new marketing material. When we have a page dedicated to scaling retrospectives and also scaled analytics, that’s what comes to my mind right away.
Anthony: We’re getting a lot of the pieces here. Now, we’re going to start putting this together into what a campaign can look like. Next is thinking about what the funnel is. There’s somebody that’s going to go on to become a customer of yours. I’ve seen your website and it looks like they can sign up right there. What else I see is there’s a schedule a demo button. When somebody signs up on your website or if you ever have somebody reach out to you and say they’re interested, tell me a little bit about what your sales process looks like.
John: To be honest with you, we are just starting to really come up with our marketing and sales process. Traditionally, it looks like they come to our site, they may be play around with it, they have questions, they book a demo or they chat with us through Intercom or write on our support tickets. We handle it from there. When we release all these new marketing stuff, it’s going to be maybe more traditional. If we already use the scaled stuff content as an example, we’d have a special landing page for scaled. You can put in an email address to learn more about scaled agile retrospectives.
Honestly, hopefully, they’ll sign up. Actually, I think Rob might kill me because we talked about this a long time ago. Our schedule a demo button still goes directly to us without qualifying them, really. It hasn’t been that crazy of a problem. I would either want their email address or for them to schedule a demo as a goal (I guess) from an ad, but I don’t have enough experience with these types of marketing ad funnels to really speak beyond that. That’s what I think would be a goal.
Anthony: Right now, if somebody hits schedule a demo, then they get in touch with you. You guys get on that call, have a quick demo. If they’re interested they sign up from there?
John: Yeah. That’s exactly right.
Anthony: Okay. Sounds good. Next is starting to put some of these pieces together. As I said, if you go direct without scheduling a demo on LinkedIn, most people out there haven’t heard about you. Most companies in general out there, if you’re not a mainstream company or a well-known brand, people haven’t heard about you. If you put schedule a demo in that first ad, people just don’t know enough to be qualified to sign up. Someone might submit that form but might not really know exactly what you do, could be a little confused, or they think of something else.
We see that people that sign up for that usually, it’s a much lower conversion rate. You’re paying a lot more for each lead. The leads that you get usually aren’t great because they just don’t know enough yet. Going content-focused, content first, the more educational route, using these lead magnets is a good way to get people to sign up and positioning it so it qualifies the person as they sign up.
When you use LinkedIn’s targeting so that these are good leads that are coming through because they are only targeting companies up to a certain size, people with these specific job titles, and then positioning the content as something for SAFe would be a great piece of content to have.
There are different levels of content and usually, we see that white papers, guides, and checklists often do the best. Quick and easy downloadables, something that someone can learn something about you. We see that quick and easy downloadables get the highest conversion rate because somebody can download it quickly, read it, and learn a little bit about you. You started the conversation with them and then you can reach out to them afterward via email to set up that follow-up call.
Not everyone will take that step, not right away, but part of the sales process that I mentioned having honed in is you want to have some kind of follow-up email sequence out there, some Drip campaign that when somebody signs up and says they’re interested, and they’ve downloaded the piece of content. Maybe you have a weekly email or a monthly email that goes out, maybe with more content about SAFe, you can alternate videos of your platform or information about your platform, and then you can include little offers in there, too. Like here’s the next step, schedule a demo, or start for free—I see you have here—so having that follow-up sales process is important. Thinking about what that content offer is going to be, yeah, I think something like SAFe could be a good piece of content.
John: I have actually another question around that. If we have an ad and we say, here’s this great piece of content, come and download it. That takes them to a landing page of ours where they can do that. Is the entire goal for them to download or do whatever that content thing is, should we not even put a sign-up now button somewhere on there that’s like a different call to action? Or do you focus to just get them the content right then and then nurture them through email?
Anthony: Good question. Yes. In the funnel, you do want to offer them that next step or at least show them what that next step is going to be. The first goal is yes, get them to that landing page, that they can download the content and read it. Them reading that content is what warms them up to your brand. They see your logo, but more importantly, they learn about ScatterSpoke and they learn what it is you do. At the end of your PDF, you might have a little blurb about ScatterSpoke and click here to learn more. But on that landing page, you want them to learn a little bit, you want them to read that lead magnet, and then usually, maybe lower on the page, maybe on the side there, we’ll have a little button and then indicate like, hey, if you’re interested in getting ScatterSpoke to help you with this problem, to help you with scaled agile, then click here to schedule that demo.
Oftentimes in our funnels, there’s a lot of tools out there that are like scheduling widgets you can use and you can embed those right in your landing pages. Maybe somebody clicks that button and they said, okay, I am interested to learn more, or I want to try this tool out. I’m going to sign up for this scaled agile stuff and they click that button, it can go on to book a call with you.
John: Got you. That makes sense. You can do both, but the primary focus should probably be on the content, that you can still try to lure them further down the funnel.
Anthony: Yeah. Them consuming that content is what is going to educate them and warm them up to your brand. You do have a competitor out there. If they didn’t read that PDF, then they don’t know what makes you different from Retrium. Them reading your scaled agile piece of content in your lead magnet, you’ll want to teach them something, but then also weave in how ScatterSpoke helps you achieve that goal. Through them reading that, they’ve learned more and they know more about ScatterSpoke.
John: Makes sense.
Anthony: Next is talking about what some of the ads could look like. I have a couple of audience sizes here based on the different titles and stuff you’ve given me. If we were targeting the computer software industry and if we were targeting engineering and project management type of roles—C or the VP levels—and using these different skills, it looks like that’s about 20,000–30,000 people in that audience, maybe bigger, maybe smaller if we add or remove some of these piece of skills that we talked about. But that’s what we want to see is we want to see at least 20,000 people in that audience. That might not sound huge, but that’s still a lot of people out there.
If you use an audience that’s smaller than that on LinkedIn, you might just have some deliverability issues, trouble getting in front of people, but having a 20,000–30,000 audience is a good size. If you go on LinkedIn and you have a massive audience of a million people, then you want to start segmenting that down into different sub-audiences that you can split test.
For the other side of things, if we were to target other industries outside of computer software, that’s a lot of industries out there. Looks like that audience is about 60,000–80,000 people. This one is taking all those agile skills and then also ending that with a different tool that it could be using. This is probably a pretty good audience for you, too.
That’s the first thing we want to look at is what’s the size of the audience that we can be targeting on LinkedIn. Our usual target is somewhere between 20,000–80,000 people. If it’s under 20,000 that might be a little small. If it’s over 80,000 people, then usually we have the opportunity to get more targeted in it.
Next is talking about what some of these ads could look like. If we were doing a scaled agile framework PDF, the question for you is what are some of the main pain points that one of these Scrum Masters has approaching scaled agile.
John: What we’re trying to do in our tool is oftentimes teams will complain about the same thing for months and months and months, and it doesn’t really ever leave the team. One of the things we’re trying to solve with this scaled idea is to elevate them to more leaders in the company. What we’re trying to solve and the pain point specifically is to get things off the team level and into a leadership level in a formal process or […] way so that they know what’s happening on the teams. Otherwise, they’d often get lost and it just remains as the problem for long periods of time.
Anthony: Got it. The problem there is that things are getting lost?
John: Yeah, or they’re just never solving the problem. They’re just like, oh, it’s out of our control. We can’t change some fundamental company things so we should just never tell anybody about it. But I think leaders often do want to know about that stuff still. If they don’t feel like there’s a way to talk to the senior leaders in a company, then they’re never going to tell them. We’re offering in a way to make a tidy inbox of problems and concerns from teams up to higher-up leaders at a company.
Anthony: Okay. The last piece here is what some of your ad copy could look like. Maybe, you’d say for your scaled agile PDF here, your ad copy to the engineers, maybe you’d say, having trouble submitting your retrospective feedback? Download this scaled agile guide to learn how to better manage your retrospectives for your company.
We also find like throwing stats in there can also be really powerful. I saw in your website, there’s mentioning about wasting time, stuff like that. Different angles you could take is are you wasting time in retrospectives and not getting anything done? Are you having trouble getting in touch with higher leadership? And then throwing in the stat saying, the average sprint team wasted 30 hours. Download this ultimate guide to scaled agile to learn more.
Somebody who signs up for that using our LinkedIn targeting, we can know that these are engineers using these tools […] agile and likely having this problem or interested in the solution that you have. That’s probably a good candidate for you. Just an example of some plausible ad copy.
Maybe another cool thing I could probably do after is send this over to you, maybe package it all up, send it over, maybe put together an image or two, what it could look like along with some of the audience targeting stuff that we talked about, put it on a package and then send it over. That might be a good wrap up of everything that we talked about.
John: Yeah. The examples you just gave are spot on and would totally work. We pretty much narrowed it down to what would get these SAFe guys moving, honestly. They’ll love all this stuff. I’m actually curious, though. Two things that we’re talking about along the way. We have one audience size of 20,000 or 30,000 people. One audience size that was much bigger, like 80,000 people. Who should I spend money on first?
Anthony: That question I’ll turn back to you. I would turn back to you and ask who’s the more important prospect for you?
John: I think it’s hard to know who’s going to pull out the credit card at the end of the day. I guess, is there a way to say, I want to spend 60% of the budget on that group and 40% of the budget on that group on LinkedIn?
Anthony: Yup. What we would do is set up separate campaigns to split test them and then each campaign is its own audience. We’d basically split test your audiences and then you allocate a specific budget to each campaign so we could do it. Yeah, we can do 60% to one audience and then 40% to another. Usually, when we launch campaigns, we always have at least two audiences. We have a measuring stick so that we can compare them. The different levels of split test we usually set up are at least two audiences, at least two lead magnets, and then several ads for them.
John: Probably a lot of companies in my position would want to know this. Everything we just talked about, what’s the right size budget to think about? If you go to an ad company (and I have) then you’re like, what should we start with? Well, you should do a $5000 minimum. Other people have said, you can probably get early results for $500–$1000. How should we think about setting a budget for something like this?
Anthony: LinkedIn is a more expensive channel. I usually recommend the minimum for each campaign is about $2000, and then the minimum amount per campaign level is about $1000. Then you can be sure you’re getting at least enough clicks in that you’re getting enough data to make a decision based off of. For here, if we were doing these two audiences for you, I’d recommend $1000 over a month period for each audience and then $2000 total.
John: Okay, got you. We’re a small, mostly bootstrap company. Obviously, these things are really important to us. What’s a normal clickthrough rate, just to put in perspective?
Anthony: Normal clickthrough rate, the LinkedIn average is about 0.4. Anything above that and your ads will actually benefit going in the auction. You’ll get cheaper ad costs. 0.4 is actually relatively low. We like to say you want to shoot for usually around like a 0.75 or so. That’s a good CTR that we look for.
At the end of the day, we don’t look at CTR a ton because on LinkedIn you’re usually paying for every click. Whether or not something clicks, you only pay when somebody clicks. Having a little CTR rate doesn’t usually hurt you unless you’re below that 0.4 level. We don’t look at CTR a ton, but we look at what’s the CPC that you’re paying.
John: Right, but it just helps me ballpark. I can take the number of people that might view it, just start to do basic math, and maybe estimate what CPC would look like. Okay, that’s all really, really handy. This has been awesome.
Rob: Anthony, if you do want to package that up and send it over, I might love to pull maybe just a couple of pieces out of it, put it in either our show notes directly, or maybe as a PDF people can download. Just hearing it all on the show is super informative, but then being able to even see what you’re talking about could be helpful for listeners too.
Anthony: Yeah, definitely. I’ve been trying to do my best to articulate the different job titles and copy and stuff, but it’s totally different seeing it done in writing.
Rob: I know. To call out for the listeners, you would ask, can we do a screen share. I know that would be ideal, but it’s just so many of our listeners are going to be audio-only that I felt like it would leave a lot of people out. If they need that visual element, we’ll be sure to include that in the show notes.
If you would like to keep up with Anthony, you can head to modernmedia.io, or head to LinkedIn where he has a prominent profile—more than 500 connections. I was going to make a joke and say, and Anthony has no LinkedIn profile.
Anthony: That would be funny, though.
Rob: I don’t know if people might have a dry sense of humor, maybe. Wouldn’t have worked. John as well, you are @scatterspoke on Twitter. Gentlemen, thank you so much for joining me today.
Anthony: It was fun. Thanks for having me.
John: That’s right.
Rob: Thanks again to Anthony and John for joining me on the show today. Again, check out stateofindiesaas.com if you are a SaaS founder and are willing to provide anonymized data to really help educate us all on this whole independent SaaS movement. The non-venture track bootstrap or mostly bootstrapped SaaS founders the more data we can get, the more knowledge that we have and can share with one another. Thanks so much for listening and I will see you again next Tuesday morning.
Episode 517 | Married Co-founders Who Turned a Free Tool Into a Fast-Growing SaaS Product
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We’re joined in this episode by the founding team of Scatterspoke, John Samuelson and Colleen Johnson.
What started as a lark to learn new technology has now turned into a successful business with more than $12k MRR. In this episode, we learn how they turned a side project into a successful fulltime business.
The topics we cover
[02:09] The launch story behind Scatterspoke
[10:02] Shifting to enterprise customers
[16:17] The toll of working fulltime while trying to bootstrap Scatterspoke
[18:01] Hiring out for development
[26:00] Free plan and raising prices
Links from the show
- Scatterspoke | Twitter
- Scatterspoke | Website
- Colleen Johnson | Twitter
Rob: Welcome to this week’s episode of Startups For the Rest of Us. I’m your host, Rob Walling. This week, I sat down with the founding team of ScatterSpoke, John and Colleen. I like their story of how it started almost as a lark—something to learn some new technology, and it’s a hobby that turned into a business. Now, a pretty successful business.
By the time this goes live, they should be at or above $12,000 a month in MRR—to give you some type of scope of where they’re at—and they’re growing pretty quickly, in the 10% per month range. From my observation, they’ve hit product-market fit, and they are getting towards that point of escape velocity working diligently towards it.
I hope you enjoy my conversation today with John Samuelson and Colleen Johnson, the co-founders of ScatterSpoke. John and Colleen, thank you so much for joining me on the show.
Colleen: Thanks for having us, Rob.
Rob: Yeah. It’s great to chat with you again. I know we did a MicroConf On Air a few weeks back, but for folks who didn’t see that, they certainly heard about ScatterSpoke in the intro of this episode. Or they may have also heard that you are in TinySeed batch two. ScatterSpoke, your h1 on your website is, it’s time to have a smarter retrospective. We are improving the way teams improve, and you’re focused on helping people have better retros.
This is an Agile software development methodology. You guys have been working on this for several years now. It’s 3 or 3 ½ years ago, by now.
Colleen: Yeah. It’s definitely ebbed and flowed for us. I think we actually bought the domain name in 2015, and then really threw some stuff together and didn’t do anything with it for probably two years. It’s been around for a while, but not in the shape and form that it is today. That was a big relaunch effort that we did in 2018 to really build it into the tool than it is today. Where you register, invite your team members, and can buy an upgraded plan with more features. None of that was there for the first three years of us just squatting on the domain name basically.
Rob: Right. I have a few notes from your TinySeed application, and also for memory was that the first year, year and a half, it was a tool that was up there for free. There were no accounts. It was just a really super basic thing, but then you added the analytics to it and noticed that, hey, people are actually using this thing. Maybe we could launch a business around it.
John: Yeah, that’s exactly right. I built it to learn new technologies. I’ve always been a Java developer, and I wanted to learn this new thing called Node.js. That’s what started it all. We just put it online. You could go to it and basically press a button, share a link, and a million people could use it. That would probably crash our server, but that’s exactly how it started.
Rob: You built this tool because Colleen is well-known in the space, right? She has this personal brand in Agile space, and you’ve done a lot of speaking, writing, and are considered an influencer.
Colleen: Yeah. I’ve been in the software industry for about 20 years and in the Agile space for about half of that. It really helped me fill an immediate need I had in consulting when teams would either cancel a retro because somebody was out or not be able to have the retro because not everybody was in the same location.
We combined John’s interest in learning some new technology with an immediate need I had. It was great because I was able to really take it with me. Not just to clients, but also in the training sessions, large conferences. We were able to run retros after conferences or public speaking events. We were starting to get a lot of traction really organically without ever spending any money on marketing, and then also getting lots of feedback organically.
Rob: Was that essentially how you got early customers and did early customer development was just by going to these events speaking and having people use it, try it out, and give you feedback?
Colleen: Definitely. It was probably—for the first two years—how we were getting customers and users, and it was how we were getting feedback. And then when we added the ability to register an account, once John dug into our Google Analytics and was like, holy […]. There’s a lot of people using this.
We set up the ability to have a user account and then added Drift to the site. That was another chained point for us where we started to get real-time feedback on where people were getting stuck, where they had questions about the tool or were requesting features that we didn’t have yet.
Rob: Yeah, that’s cool. It’s always fun to hear. It truly is like a maker story where John wants to learn new technology. Colleen has experienced in this space or in this niche and is a bit of an influencer there. You sound like you maybe build it on a whim a little bit or like, hey, this is going to be a fun lark, a fun little project. You put it up for a year, year and a half, and really don’t even have the ability to register for an account. But then there’s just so much usage.
It’s that free tool. Some people go open source to the business route, but you just went literally like the free tool to the business path.
Colleen: I think, in some ways, being a maker project hurt us early on. John was excited to try out the new technology, and I was so close to the teams using it that every time we heard feedback about the simplest thing, we tried to go implement that or change something pretty dramatic in the tool.
We were almost being, in some ways, maybe too reactive or too close to what we were building. I think it took us a while to start to take a step back and say, how do these things help drive business and help us look at this more as a business instead of just a hobby or a pet project?
Rob: Yeah. There’s something I wrote about in my first book and I called it project/product confusion where developers do this especially. I did this in the early days where I would have this great idea for this project. It’s a web app that organizes my audible library, or it keeps me in touch with any author who I enter into the system, I suddenly get an update when they publish a new book, or just whatever.
It’s an interesting idea for a project, but turning that into a product that actually makes money and enough money that it’s worth spending time on is a huge, huge difference, and the maker in me always wanted to make cool stuff. In fact, I made a bunch of cool stuff, but I always thought they would become revenue-generating products, and that was a big mistake.
I was a little bit delusional, I think, in thinking those could be that. I could totally see how building this, it sounds like you almost erred on the other side where you built this free tool to learn new technology and because you happen to be in the space, and then didn’t necessarily think of it as much of a business as perhaps you could have.
Judging by your progress to date, it’s obvious that this can be a successful revenue-generating profitable business. If you’re going into that with that maker creator mindset, it’s not that you can’t do that. Have I seen many 6-figure SaaS businesses built with that? absolutely.
Have I seen many 7-figure SaaS businesses built with that mindset? A lot fewer, and probably 0 8-figure businesses that I think about. If you truly want to make stuff, awesome. That’s how when I started out, it was just like, I want to build cool […], I want people to use it, and I want to be able to live off the revenue. If that’s all you need, that’s great. I got up to about $120,000, $150,000 a year in revenue, and that was amazing.
But when I wanted to shift gears and get up to take that next step and be like, hey, I want to build a 7-figure or multiple 7-figure business, I do think you have to start maybe shifting the mindset a little bit.
You told me before we hit record that you were focused on the small Agile teams. But then enterprises would come and they would ask for features that you weren’t necessarily thinking about or that interested in building. But you did make the shift and decide to build those things for those larger teams.
You want to talk me a little bit through how that process went and why you decided to go down that road instead of just keeping it as a true, hey, I’m a maker and this is my vision and I’m going to build the product that I want, even if it does hurt our growth (in essence).
John: After that first year of launch, when we decided to make it a business, and we weren’t certainly focused on smaller teams, it was a brutal year. People had never given us that much authentic feedback about what sucks or what wasn’t working. It was hard. There were a lot of bugs to get through, and that was one thing. But people can be ruthless, and it cuts you deep.
Actually, we were getting to the point where we were like, you know what? Let’s go back to the maker mindset because this is just not fun or have it be more of a passive business. Out of nowhere, a giant enterprise deal showed up, and they were very interested in some contingencies of we want these 10 features. If you build these 10 features, we’ll sign a deal.
We looked at them, and we’re like, we’ll make these our own, and these wouldn’t be our first choice of what to do, but we did it. That’s when the light bulb went off. I think big enterprises are where all the money is at for us, and most of these come with some custom features. We got to get good with wanting to build those, and it’s been a game-changer ever since.
Rob: Yeah. This was about a year and a half ago in early-2019. You mentioned that you had been grinding it out for so long on the side and that you were considering, should we even do this? It’s not making enough money to make it worth it. And then this enterprise comes along and it’s that realization.
I think so many entrepreneurs—especially developers—see the model of the Basecamps and the Mailchimps where it’s like, hey, I can build the product for $10 a month or $30 a month. I can do the SMB—the Small Business thing, the self-service, and that’s the business that I want to build because I’ve seen that model. It sounds like fun. I don’t have to do high touch sales and deal with these big enterprises with the six months sales cycles, the security reviews, and all of that.
While that is totally possible., it is not actually the optimal way—in my experience—to build a big business quickly. Really, if you look at more of the SaaSter model, which is going after the big-ticket Fortune 1000 or the Fortune 5000, it’s the high touch sales, and it’s big contract values. That tends to get you there faster.
Even I would propose—as good as or better than that—is this model that I think several folks in the TinySeed batches have, and you guys have it as well. This dual funnel is what I’ve been calling it where you do have that high-end enterprise funnel. You do have folks coming in paying (let’s say) tens of thousands a year is how I think about an enterprise sale.
But you also have this nice influx of folks on the lower end, small teams. Maybe it’s a free plan. Maybe it’s the $10, $50, or $100 a month plan that you get a lot of volumes through and that tends to be a lot lower touch, but you get a lot of users and therefore you get that brand momentum. Because the more users you have there, oftentimes, there’s more word of mouth that then can lead to the enterprise funnel.
Have you guys ever thought about this in terms of that like, hey, we have two really different funnels? Do you handle those differently in terms of how much touch, how much onboarding, and perhaps how much support do you offer the two types of customers?
Colleen: Yeah. I think the concept, in general, has been pretty new for us in the last year, but definitely eye-opening in the sense that there’s value in both. Like you said, the overhead to get those small teams in the system and onboard is really low. It’s self sign up. they pick their subscription, invite their team, and there’s usually not a whole lot of overhead for us. Versus, like you said, those big enterprises can take up to six months to go through a security review, legal back and forth on contracts, and then add-in.
John said those custom feature requests and our time to get them in is quite a bit longer. But usually, once we have them, their contracts are anywhere from a year to three years, or maybe longer. There’s value in both of those channels for us because the one that requires more time obviously pulls us away from doing a lot of other stuff.
I think the other thing is, in some ways, that the middle tier like you described is a little bit of a gateway drug for some of these other organizations where they want to test it out, maybe in a pocket of an organization that’s a huge company. They might use the team subscription plan or a business subscription plan to try some of the features out before going to the enterprise.
That’s also been a nice funnel for us of people coming in and trying some of the stuff out before jumping all the way to enterprise. I think we found a couple of different channels or combinations of good paths through those different offerings.
John: I’ll just add to that too. Something that surprised me a bit, like I mentioned, we built a bunch of custom features for that big enterprise client. Those features now work for all of our small teams just as well. We built these enterprise-grade features for these guys and a lot of them, and it’s actually helped the smaller end funnel a lot.
Rob: How has it helped them?
John: A good example, in our tool, we have something called facilitators control. In the beginning, we were just like, this should be a democracy. Everybody should just be able to do whatever. Everybody can have controls to take over the retro. This big enterprise said, no, no. We want somebody to be in charge.
They run the meeting, and we don’t force that to happen. You can do either or, but it turns out these smaller teams also like that to have a facilitator to take charge of a meeting. We were of the opinion that it should be a democracy, not have a hierarchical role set. It’s actually a blessing that we made that because it’s definitely helped us out on both ends of the funnel.
Colleen: Yeah. I think we figured out a way to do it to still support that model. Like John said, to make it optional so that the functionality is there if you want to use it, but it’s not a requirement. That’s a path we did with a lot of what we offer in the tool. The functionality is there if you want it, but also, if you don’t want to use it, you don’t have to.
None of it is forced, and I think that’s something we learned throughout this process too that the more we could make self-service inside the tool, the more we’d be able to serve both of those different client paths.
Rob: That’s an elegant balance to strike because, oftentimes, enterprises want large, clunky things. They want a ton of settings. They want checkboxes everywhere. If you want an easy to use self-service tool, you don’t want 50 checkboxes in your settings. You tend to want to be a little more opinionated in your software.
If you’ve been able to strike a balance with that and be able to have the enterprise features help the smaller teams and potentially vice versa, that’s a really nice way to go. Because the fear is always that you’re almost like building two products in one and it becomes Frankenstein. It’s like our enterprise customers want all this crap, and our small teams want all this stuff. We have to build them into the same product, but it should maybe be two different products really. If you’re able to strike that balance, that’s a really nice way to go.
Colleen: I think the only thing we’ve ever really said no to, from a large enterprise request, is our tool is completely anonymous. We did that by design to create safety in your answers and being able to be really honest with your feedback that you’re providing to your team. If you want to put your name on it, great, but we’ve had requests from small businesses and large businesses to go back and either toggle that on and off.
We even had one request one time where somebody was like, I need you to tell me who wrote this exact card. We were like, no. I’d say that’s the only thing that we’ve really pushed back on from a feature perspective just because it was so core to how we wanted the tool to function that we weren’t willing to bake that in for any contract.
Rob: Yeah. That makes a lot of sense. I’m thinking back to your timeline, you think early-2019, you’re questioning, was this the right thing to do to double down on this business? You get this enterprise customer or prospect who says, hey, build these 10 things and we’ll pay you a lot of money (in essence).
You said yes to it, you built it, and you got them onboarded. But at that point, you’re still not making enough to quit the day job. I’m curious, John, during that year, because you applied to TinySeed in November 2019. Somewhere between early 2019 and getting funded from TinySeed, which I guess was just about a year.
I think we funded in February or March of this year. So it’s been about a year that you’re toiling away. You guys are married. You have small kids. You were basically working all nights and weekends, right? How did that take its toll on you, your mental health, and your marriage? However, you want to describe it. I’m just going to make the assumption that this was not an easy time for you, and I’m curious. There’s got to be folks in the audience who that resonates with.
John: The biggest thing for me is I can work long hours. I can work hard. That’s just part of who I am, but it’s more of a guilt problem to me. What I mean by that is if I’m not at my W-2 job, I’m at home, it’s a Saturday, and I take four hours to go to the park with the kids. I mean, that’s four hours that I should or could be working, and then it’s the opposite is true too.
If I spent those four hours on a Saturday working instead of being with my family, I feel guilty the other way. I feel like the deck stacked against you. You feel guilty no matter what you do. It’s like I have to make this business happen, and I also need to be a good father and husband. That’s by far, in my opinion, the worst part of it. It’s not working long hours. We can get through that. It’s guilt.
Rob: Yeah. Colleen, do you have any additional thoughts on that?
Colleen: Yeah. I mean, I would totally agree. I think the hard part is finding that balance. We’re always trying to teach our kids to work hard, play hard mentality too, but it’s that making space for the play hard. It’s easy when you have the day job or the W-2 job, and this becomes a night and weekend project to feel like there’s never time to enjoy it or never time to play.
I think taking the TinySeed investment and being able to go full-time on this really changed the course of that for us. Although, COVID definitely threw a little bump in the road.
Rob: For real. I was going to ask about that later, but let’s talk about it now. You mentioned offline to me, one of the most painful parts of the recent couple of years is you finally get to the point you’re having enough success, you applied to TinySeed, you get the funding, you’re able to quit the day job, and then really focus on ScatterSpoke, and then COVID hits.
All this happened. Now all your kids are at home, so you don’t actually have all the time, or perhaps all the mental bandwidth. Maybe like me, because I have three kids that are here at home, I’m working at home during the day and I’m feeling a little guilty that I’m not with my kids, which isn’t okay. I should have some time to work and feel okay about it.
I just love to hear more of your thoughts on that whole experience and on how that felt and how you guys have dealt with that.
John: I quit my day job in early-February 2019. I love the company I was at, so it was a hard departure in general. But the day I quit, the next few weeks—I think I said something like this to you before. I felt like the king. I was getting all this time to do all of this work every day, and it was awesome. It felt like the needle moved very quickly from where we had been. And then all of a sudden COVID hit, and all of the kids are at home. I don’t want to equate this to having a job, but it’s a job. Well, all the kids are at home, you’re making lunches, and chasing a two-year-old everywhere.
It was very quickly like that flame, that spark that I had from finally getting there, which in a lot of ways was like the first big goal to quit your day job. It’s like I made it. A month goes by and then it just gets ripped away by COVID. I’m not mad. In a lot of ways, this is the best time of our lives where we spend so much time with our kids, but it sucked. It’s like going back to having a job again. It was very rough.
Rob: Yeah, it sounds like. Just to clarify, you said you quit your job in February of 2019 but it was 2020? Within a month the lockdown started.
John: Exactly.
Rob: Something that we had also talked about. I know that at a certain point—this is before quitting your job—you had tried to hire out some of the development because you just couldn’t keep up with feature requests as often happens. You guys started with a free tool, and then even once you started charging—had a free plan. So you have a lot of users in there asking for features.
I think you made a mistake that I made as well. I think a lot of us do is hiring friends. Instead of going to Upwork or going whatever we’re going to do outsourcing to maybe it’s offshore, maybe it’s not, but it’s finding people where you can have a single relationship with them. Hey, I’m the employer, in essence, and you’re the contractor. When you hire friends, you have a dual-relationship, and that makes things complicated. You want to talk to people through your experience with that.
John: Yeah. I think as engineers, over the years, not even our project, but I’ve been in other people’s projects where it’s like, hey, we should totally build a thing. You do that, and they usually don’t go anywhere. When I had ScatterSpoke going on—this happened a few times. I tried paying my friends. I tried just like let’s do a trial period and if this works out, maybe we can talk about equity.
Really what happens is that you get all excited, you sit down, and you have like one great meeting where you’re like, all right, you’re going to do this. I’m going to do that. And then the week starts piling up and they slowly are not doing anything. There’s just not a lot of accountability because they’re your friends. Often friends in professional settings, like at your day job.
It’s hard to really come down on them because of that. At the end of it, I usually would just cut ties with them and say, look, this just isn’t working out. It’s not a big deal. Let’s just move on. I’ve changed that to hiring people I don’t know, and specifically hiring people, not in the US. I have a whole rant about that, but I’ve found developers in Europe especially just seemed to not be so whiny just to put it bluntly. I’m a US developer. I can say these things.
Rob: I was whining when I was a US developer too. I’ll admit it.
John: We all are. We all get so used to these tech startups. Everybody in the company treats you differently because you’re the tech guy, you know how to do all this. It’s a whole other thing, but anyway, our business changed. This was actually one of the good things about COVID.
When I started slowing down, not having more time, that’s when I found an offshore developer that really worked. You could give them your requirements, and they just were pretty self-sufficient, get the stuff done. You tell him when you want it done, and it was done by then.
Rob: That’s cool. It doesn’t always work out that way, of course, but it’s nice that you either got lucky, interviewed well, or whatever, and were able to turn that corner. Because I think, as a developer, outsourcing development can be a real challenge because I’m going to put this in quotes, “No one can ever write code as good as I can.”
This is the internal monologue of every developer ever. It is nice that you’re able to essentially get parts of that off your plate. Do you still write much code in the product, or are you just doing more technical direction at this point?
John: I do both, but I do the stuff that’s hard or tricky. We’re working on some more pricing stuff right now. I do all that stuff. I just don’t trust yet somebody else to do that. But in general, like, hey, go build these screens to do this other thing. It’s fine. They can go do that, and honestly, you got to let go at some point.
You cannot hold everybody to your standards. At the end of the day and after being an engineer for many years, it doesn’t matter. If the buttons work, there are so many big systems built with duct tape, and they work. You got to get over that as a technical founder.
Rob: Yeah, I agree. That was when I started becoming much more effective as a business owner when I learned that too, and it took me many years. It took me too long. It took me five, six years of running software projects and products. And I was still mingling in the code, still making tweaks, and eventually, I became more valuable to the companies once I outsourced my own development.
As we move towards wrapping up, I wanted to get into your free plan and raising prices once you got into TinySeed. I’m curious, Colleen, do you remember when the two of you—for folks, TinySeed, obviously, a startup accelerator for SaaS companies. You apply and then you do Zoom calls with myself, Einar, Tracy, and sometimes other folks to find out more about you and your company. We ask questions and all this stuff.
I remember, I think Einar may have talked to John, and one of the things Einar said is ScatterSpoke is awesome. They have a free plan. I’m not sure that’s a good idea. I think the pricing is messed up in essence—isn’t accurate, which is very, very common. I think most of us, probably, 70% of founders who haven’t given a lot of thought to the pricing, have screwed it up in some way or another in their product.
But then, when I was on a call with the two of you and I started digging into the numbers of like, whether the free plan converts? What’s your pricing? Do you remember one of the early things I said about the free plan? Do you remember what my general sentiment was?
Colleen: I don’t remember.
John: No.
Rob: Okay. Which is fine, it was like nine months ago. I don’t expect you to. My first thought was you need to kill the free plan. It just didn’t make sense. The numbers didn’t make sense to me. That’s not a blanket statement of free plans don’t work because that’s not true. We see free plans work, and it wasn’t a blanket statement of this will never work, but it was a first instinct of like, wow, you have that many people using it. So few are converting, and maybe it’s too permissive, which I think you guys actually knew that as we were talking.
That was something that you have since done. At this point, you have a free trial, but you can’t sign up for a free plan anymore.
Colleen: Yeah. We’re in the process right now of killing that, actually. We redid our pricing tiers first and gave everybody some grandfathered users and options with those new pricing tiers. We’re about to roll out what will essentially kill the free tier, and it was hard. I mean, it’s still a little hard for me to let go of it, and I think it’s back to being, in some ways, too close to our user base.
I feel like we built this off of people getting to try it, people who knew me, and attended my classes, workshops, or whatever being that user base. I feel like I lured them in and then now I’m like, no, you can’t use it anymore. But I think we have reached maturity as a business that it isn’t a hobby and it isn’t a free tool. We know the value is there, and that people are willing to pay for it. It’s time to grow up.
Rob: Yeah. I like that you said that it’s hard because it is. I think there is a common conversation in the MicroConf community of, hey, charge more, raise prices, and everybody’s undercharging. Most of the time, that’s honestly true, especially if you’ve never really raised prices or never looked at your pricing. That discounts the emotional side of things, both the relationship you have with your users and also the fear.
Raising prices is really scary. Killing free plans is really scary. Adding or removing a credit card before a free trial is really scary. I’ve done all of those things. Every time I’m like, I don’t know if this is going to work. If it doesn’t, maybe I’m going to make a bunch of people mad, and am I going to kill my business with this?
That is something we’ve done pretty intentionally in the first month or two of TinySeed of the batch is to say, hey, who here thinks they have a pricing issue? Again, it’s typically 70% of batch two raised their hand in the Zoom call, but then it’s to help folks think through, not only how they can actually change it mechanically and logistically, but how to deal with the emotion of that. How to convince people, hey, if this doesn’t work, it’s pretty easy to roll back. This is not an undoable decision.
Given how large of a lever—I keep saying pricing is the number one lever in any business. Especially in SaaS, where it’s recurring, pricing is your number one lever. It’s the easiest thing to change and to double growth overnight. Everything else requires more customers, requires more features, or requires something else. But just to change a number on a page and in your Stripe account and have it suddenly change it is a big deal. It deserves a lot more thought I think than most founders think.
All of that is to say how did you deal with, get through, or push through that emotional resistance? Whether it’s the fear or whether it’s just a nagging doubt of like, maybe we shouldn’t be doing this. I’m curious how you pushed through that in order to make such a drastic change.
Colleen: Honestly, once you see that Stripe account number go up and up and you see those trails convert, it’s pretty easy to support it. I think that was proof for me. I think you’re still offering. To me, we built this tool to help teams and to make this easier. I felt like I was taking that away from them by removing the free tier, but I think what you see, as you go down this path, is the value is still there. You’re just asking them to pay to get that value.
Once we start to see all the conversions, and honestly, like new enterprise contracts coming in now, I think it really just supports that the value is something worth paying for.
Rob: Awesome. We’re out of time. Thank you so much, John and Colleen, for joining me today. If folks want to keep up with you on Twitter, you’re @ScatterSpoke, and Colleen, you are @scrumhive. I like that. That’s a cool Agile Twitter handle. And then, of course, scatterspoke.com. If folks want to check out what you’ve been working on and potentially check out for doing their retrospectives. Thank you guys so much for joining me on Startups For the Rest of Us.
John: Thanks, Rob.
Rob: Thanks again to John and Colleen for joining me on the show today. If you’re interested in potentially joining TinySeed batch three, head over to tinyseed.com and get your name on our email list. I believe we’ll be opening applications again here in the next four or five months.
In addition, if you are an accredited investor and you’re interested in investing in early-stage B2B SaaS companies like ScatterSpoke and other TinySeed companies that you’ve heard on this podcast, head to tinyseed.com/thesis. You can see our unique investment thesis that we have at TinySeed, why we believe that B2B SaaS is an amazing investment, and to be able to basically index across hundreds of these SaaS companies and diversify investment is a solid way to go. You can learn more about that, tinyseed.com/thesis. Thank you so much for joining me this week. I’ll see you again next Tuesday morning.
By the time this goes live, they should be at or above $12,000 a month in MRR—to give you some type of scope of where they’re at—and they’re growing pretty quickly, in the 10% per month range. From my observation, they’ve hit product-market fit, and they are getting towards that point of escape velocity working diligently towards it.
I hope you enjoy my conversation today with John Samuelson and Colleen Johnson, the co-founders of ScatterSpoke. John and Colleen, thank you so much for joining me on the show.
Colleen: Thanks for having us, Rob.
Rob: Yeah. It’s great to chat with you again. I know we did a MicroConf On Air a few weeks back, but for folks who didn’t see that, they certainly heard about ScatterSpoke in the intro of this episode. Or they may have also heard that you are in TinySeed batch two. ScatterSpoke, your h1 on your website is, it’s time to have a smarter retrospective. We are improving the way teams improve, and you’re focused on helping people have better retros.
This is an Agile software development methodology. You guys have been working on this for several years now. It’s 3 or 3 ½ years ago, by now.
Colleen: Yeah. It’s definitely ebbed and flowed for us. I think we actually bought the domain name in 2015, and then really threw some stuff together and didn’t do anything with it for probably two years. It’s been around for a while, but not in the shape and form that it is today. That was a big relaunch effort that we did in 2018 to really build it into the tool than it is today. Where you register, invite your team members, and can buy an upgraded plan with more features. None of that was there for the first three years of us just squatting on the domain name basically.
Rob: Right. I have a few notes from your TinySeed application, and also for memory was that the first year, year and a half, it was a tool that was up there for free. There were no accounts. It was just a really super basic thing, but then you added the analytics to it and noticed that, hey, people are actually using this thing. Maybe we could launch a business around it.
John: Yeah, that’s exactly right. I built it to learn new technologies. I’ve always been a Java developer, and I wanted to learn this new thing called Node.js. That’s what started it all. We just put it online. You could go to it and basically press a button, share a link, and a million people could use it. That would probably crash our server, but that’s exactly how it started.
Rob: You built this tool because Colleen is well-known in the space, right? She has this personal brand in Agile space, and you’ve done a lot of speaking, writing, and are considered an influencer.
Colleen: Yeah. I’ve been in the software industry for about 20 years and in the Agile space for about half of that. It really helped me fill an immediate need I had in consulting when teams would either cancel a retro because somebody was out or not be able to have the retro because not everybody was in the same location.
We combined John’s interest in learning some new technology with an immediate need I had. It was great because I was able to really take it with me. Not just to clients, but also in the training sessions, large conferences. We were able to run retros after conferences or public speaking events. We were starting to get a lot of traction really organically without ever spending any money on marketing, and then also getting lots of feedback organically.
Rob: Was that essentially how you got early customers and did early customer development was just by going to these events speaking and having people use it, try it out, and give you feedback?
Colleen: Definitely. It was probably—for the first two years—how we were getting customers and users, and it was how we were getting feedback. And then when we added the ability to register an account, once John dug into our Google Analytics and was like, holy […]. There’s a lot of people using this.
We set up the ability to have a user account and then added Drift to the site. That was another chained point for us where we started to get real-time feedback on where people were getting stuck, where they had questions about the tool or were requesting features that we didn’t have yet.
Rob: Yeah, that’s cool. It’s always fun to hear. It truly is like a maker story where John wants to learn new technology. Colleen has experienced in this space or in this niche and is a bit of an influencer there. You sound like you maybe build it on a whim a little bit or like, hey, this is going to be a fun lark, a fun little project. You put it up for a year, year and a half, and really don’t even have the ability to register for an account. But then there’s just so much usage.
It’s that free tool. Some people go open source to the business route, but you just went literally like the free tool to the business path.
Colleen: I think, in some ways, being a maker project hurt us early on. John was excited to try out the new technology, and I was so close to the teams using it that every time we heard feedback about the simplest thing, we tried to go implement that or change something pretty dramatic in the tool.
We were almost being, in some ways, maybe too reactive or too close to what we were building. I think it took us a while to start to take a step back and say, how do these things help drive business and help us look at this more as a business instead of just a hobby or a pet project?
Rob: Yeah. There’s something I wrote about in my first book and I called it project/product confusion where developers do this especially. I did this in the early days where I would have this great idea for this project. It’s a web app that organizes my audible library, or it keeps me in touch with any author who I enter into the system, I suddenly get an update when they publish a new book, or just whatever.
It’s an interesting idea for a project, but turning that into a product that actually makes money and enough money that it’s worth spending time on is a huge, huge difference, and the maker in me always wanted to make cool stuff. In fact, I made a bunch of cool stuff, but I always thought they would become revenue-generating products, and that was a big mistake.
I was a little bit delusional, I think, in thinking those could be that. I could totally see how building this, it sounds like you almost erred on the other side where you built this free tool to learn new technology and because you happen to be in the space, and then didn’t necessarily think of it as much of a business as perhaps you could have.
Judging by your progress to date, it’s obvious that this can be a successful revenue-generating profitable business. If you’re going into that with that maker creator mindset, it’s not that you can’t do that. Have I seen many 6-figure SaaS businesses built with that? absolutely.
Have I seen many 7-figure SaaS businesses built with that mindset? A lot fewer, and probably 0 8-figure businesses that I think about. If you truly want to make stuff, awesome. That’s how when I started out, it was just like, I want to build cool […], I want people to use it, and I want to be able to live off the revenue. If that’s all you need, that’s great. I got up to about $120,000, $150,000 a year in revenue, and that was amazing.
But when I wanted to shift gears and get up to take that next step and be like, hey, I want to build a 7-figure or multiple 7-figure business, I do think you have to start maybe shifting the mindset a little bit.
You told me before we hit record that you were focused on the small Agile teams. But then enterprises would come and they would ask for features that you weren’t necessarily thinking about or that interested in building. But you did make the shift and decide to build those things for those larger teams.
You want to talk me a little bit through how that process went and why you decided to go down that road instead of just keeping it as a true, hey, I’m a maker and this is my vision and I’m going to build the product that I want, even if it does hurt our growth (in essence).
John: After that first year of launch, when we decided to make it a business, and we weren’t certainly focused on smaller teams, it was a brutal year. People had never given us that much authentic feedback about what sucks or what wasn’t working. It was hard. There were a lot of bugs to get through, and that was one thing. But people can be ruthless, and it cuts you deep.
Actually, we were getting to the point where we were like, you know what? Let’s go back to the maker mindset because this is just not fun or have it be more of a passive business. Out of nowhere, a giant enterprise deal showed up, and they were very interested in some contingencies of we want these 10 features. If you build these 10 features, we’ll sign a deal.
We looked at them, and we’re like, we’ll make these our own, and these wouldn’t be our first choice of what to do, but we did it. That’s when the light bulb went off. I think big enterprises are where all the money is at for us, and most of these come with some custom features. We got to get good with wanting to build those, and it’s been a game-changer ever since.
Rob: Yeah. This was about a year and a half ago in early-2019. You mentioned that you had been grinding it out for so long on the side and that you were considering, should we even do this? It’s not making enough money to make it worth it. And then this enterprise comes along and it’s that realization.
I think so many entrepreneurs—especially developers—see the model of the Basecamps and the Mailchimps where it’s like, hey, I can build the product for $10 a month or $30 a month. I can do the SMB—the Small Business thing, the self-service, and that’s the business that I want to build because I’ve seen that model. It sounds like fun. I don’t have to do high touch sales and deal with these big enterprises with the six months sales cycles, the security reviews, and all of that.
While that is totally possible., it is not actually the optimal way—in my experience—to build a big business quickly. Really, if you look at more of the SaaSter model, which is going after the big-ticket Fortune 1000 or the Fortune 5000, it’s the high touch sales, and it’s big contract values. That tends to get you there faster.
Even I would propose—as good as or better than that—is this model that I think several folks in the TinySeed batches have, and you guys have it as well. This dual funnel is what I’ve been calling it where you do have that high-end enterprise funnel. You do have folks coming in paying (let’s say) tens of thousands a year is how I think about an enterprise sale.
But you also have this nice influx of folks on the lower end, small teams. Maybe it’s a free plan. Maybe it’s the $10, $50, or $100 a month plan that you get a lot of volumes through and that tends to be a lot lower touch, but you get a lot of users and therefore you get that brand momentum. Because the more users you have there, oftentimes, there’s more word of mouth that then can lead to the enterprise funnel.
Have you guys ever thought about this in terms of that like, hey, we have two really different funnels? Do you handle those differently in terms of how much touch, how much onboarding, and perhaps how much support do you offer the two types of customers?
Colleen: Yeah. I think the concept, in general, has been pretty new for us in the last year, but definitely eye-opening in the sense that there’s value in both. Like you said, the overhead to get those small teams in the system and onboard is really low. It’s self sign up. they pick their subscription, invite their team, and there’s usually not a whole lot of overhead for us. Versus, like you said, those big enterprises can take up to six months to go through a security review, legal back and forth on contracts, and then add-in.
John said those custom feature requests and our time to get them in is quite a bit longer. But usually, once we have them, their contracts are anywhere from a year to three years, or maybe longer. There’s value in both of those channels for us because the one that requires more time obviously pulls us away from doing a lot of other stuff.
I think the other thing is, in some ways, that the middle tier like you described is a little bit of a gateway drug for some of these other organizations where they want to test it out, maybe in a pocket of an organization that’s a huge company. They might use the team subscription plan or a business subscription plan to try some of the features out before going to the enterprise.
That’s also been a nice funnel for us of people coming in and trying some of the stuff out before jumping all the way to enterprise. I think we found a couple of different channels or combinations of good paths through those different offerings.
John: I’ll just add to that too. Something that surprised me a bit, like I mentioned, we built a bunch of custom features for that big enterprise client. Those features now work for all of our small teams just as well. We built these enterprise-grade features for these guys and a lot of them, and it’s actually helped the smaller end funnel a lot.
Rob: How has it helped them?
John: A good example, in our tool, we have something called facilitators control. In the beginning, we were just like, this should be a democracy. Everybody should just be able to do whatever. Everybody can have controls to take over the retro. This big enterprise said, no, no. We want somebody to be in charge.
They run the meeting, and we don’t force that to happen. You can do either or, but it turns out these smaller teams also like that to have a facilitator to take charge of a meeting. We were of the opinion that it should be a democracy, not have a hierarchical role set. It’s actually a blessing that we made that because it’s definitely helped us out on both ends of the funnel.
Colleen: Yeah. I think we figured out a way to do it to still support that model. Like John said, to make it optional so that the functionality is there if you want to use it, but it’s not a requirement. That’s a path we did with a lot of what we offer in the tool. The functionality is there if you want it, but also, if you don’t want to use it, you don’t have to.
None of it is forced, and I think that’s something we learned throughout this process too that the more we could make self-service inside the tool, the more we’d be able to serve both of those different client paths.
Rob: That’s an elegant balance to strike because, oftentimes, enterprises want large, clunky things. They want a ton of settings. They want checkboxes everywhere. If you want an easy to use self-service tool, you don’t want 50 checkboxes in your settings. You tend to want to be a little more opinionated in your software.
If you’ve been able to strike a balance with that and be able to have the enterprise features help the smaller teams and potentially vice versa, that’s a really nice way to go. Because the fear is always that you’re almost like building two products in one and it becomes Frankenstein. It’s like our enterprise customers want all this crap, and our small teams want all this stuff. We have to build them into the same product, but it should maybe be two different products really. If you’re able to strike that balance, that’s a really nice way to go.
Colleen: I think the only thing we’ve ever really said no to, from a large enterprise request, is our tool is completely anonymous. We did that by design to create safety in your answers and being able to be really honest with your feedback that you’re providing to your team. If you want to put your name on it, great, but we’ve had requests from small businesses and large businesses to go back and either toggle that on and off.
We even had one request one time where somebody was like, I need you to tell me who wrote this exact card. We were like, no. I’d say that’s the only thing that we’ve really pushed back on from a feature perspective just because it was so core to how we wanted the tool to function that we weren’t willing to bake that in for any contract.
Rob: Yeah. That makes a lot of sense. I’m thinking back to your timeline, you think early-2019, you’re questioning, was this the right thing to do to double down on this business? You get this enterprise customer or prospect who says, hey, build these 10 things and we’ll pay you a lot of money (in essence).
You said yes to it, you built it, and you got them onboarded. But at that point, you’re still not making enough to quit the day job. I’m curious, John, during that year, because you applied to TinySeed in November 2019. Somewhere between early 2019 and getting funded from TinySeed, which I guess was just about a year.
I think we funded in February or March of this year. So it’s been about a year that you’re toiling away. You guys are married. You have small kids. You were basically working all nights and weekends, right? How did that take its toll on you, your mental health, and your marriage? However, you want to describe it. I’m just going to make the assumption that this was not an easy time for you, and I’m curious. There’s got to be folks in the audience who that resonates with.
John: The biggest thing for me is I can work long hours. I can work hard. That’s just part of who I am, but it’s more of a guilt problem to me. What I mean by that is if I’m not at my W-2 job, I’m at home, it’s a Saturday, and I take four hours to go to the park with the kids. I mean, that’s four hours that I should or could be working, and then it’s the opposite is true too.
If I spent those four hours on a Saturday working instead of being with my family, I feel guilty the other way. I feel like the deck stacked against you. You feel guilty no matter what you do. It’s like I have to make this business happen, and I also need to be a good father and husband. That’s by far, in my opinion, the worst part of it. It’s not working long hours. We can get through that. It’s guilt.
Rob: Yeah. Colleen, do you have any additional thoughts on that?
Colleen: Yeah. I mean, I would totally agree. I think the hard part is finding that balance. We’re always trying to teach our kids to work hard, play hard mentality too, but it’s that making space for the play hard. It’s easy when you have the day job or the W-2 job, and this becomes a night and weekend project to feel like there’s never time to enjoy it or never time to play.
I think taking the TinySeed investment and being able to go full-time on this really changed the course of that for us. Although, COVID definitely threw a little bump in the road.
Rob: For real. I was going to ask about that later, but let’s talk about it now. You mentioned offline to me, one of the most painful parts of the recent couple of years is you finally get to the point you’re having enough success, you applied to TinySeed, you get the funding, you’re able to quit the day job, and then really focus on ScatterSpoke, and then COVID hits.
All this happened. Now all your kids are at home, so you don’t actually have all the time, or perhaps all the mental bandwidth. Maybe like me, because I have three kids that are here at home, I’m working at home during the day and I’m feeling a little guilty that I’m not with my kids, which isn’t okay. I should have some time to work and feel okay about it.
I just love to hear more of your thoughts on that whole experience and on how that felt and how you guys have dealt with that.
John: I quit my day job in early-February 2019. I love the company I was at, so it was a hard departure in general. But the day I quit, the next few weeks—I think I said something like this to you before. I felt like the king. I was getting all this time to do all of this work every day, and it was awesome. It felt like the needle moved very quickly from where we had been. And then all of a sudden COVID hit, and all of the kids are at home. I don’t want to equate this to having a job, but it’s a job. Well, all the kids are at home, you’re making lunches, and chasing a two-year-old everywhere.
It was very quickly like that flame, that spark that I had from finally getting there, which in a lot of ways was like the first big goal to quit your day job. It’s like I made it. A month goes by and then it just gets ripped away by COVID. I’m not mad. In a lot of ways, this is the best time of our lives where we spend so much time with our kids, but it sucked. It’s like going back to having a job again. It was very rough.
Rob: Yeah, it sounds like. Just to clarify, you said you quit your job in February of 2019 but it was 2020? Within a month the lockdown started.
John: Exactly.
Rob: Something that we had also talked about. I know that at a certain point—this is before quitting your job—you had tried to hire out some of the development because you just couldn’t keep up with feature requests as often happens. You guys started with a free tool, and then even once you started charging—had a free plan. So you have a lot of users in there asking for features.
I think you made a mistake that I made as well. I think a lot of us do is hiring friends. Instead of going to Upwork or going whatever we’re going to do outsourcing to maybe it’s offshore, maybe it’s not, but it’s finding people where you can have a single relationship with them. Hey, I’m the employer, in essence, and you’re the contractor. When you hire friends, you have a dual-relationship, and that makes things complicated. You want to talk to people through your experience with that.
John: Yeah. I think as engineers, over the years, not even our project, but I’ve been in other people’s projects where it’s like, hey, we should totally build a thing. You do that, and they usually don’t go anywhere. When I had ScatterSpoke going on—this happened a few times. I tried paying my friends. I tried just like let’s do a trial period and if this works out, maybe we can talk about equity.
Really what happens is that you get all excited, you sit down, and you have like one great meeting where you’re like, all right, you’re going to do this. I’m going to do that. And then the week starts piling up and they slowly are not doing anything. There’s just not a lot of accountability because they’re your friends. Often friends in professional settings, like at your day job.
It’s hard to really come down on them because of that. At the end of it, I usually would just cut ties with them and say, look, this just isn’t working out. It’s not a big deal. Let’s just move on. I’ve changed that to hiring people I don’t know, and specifically hiring people, not in the US. I have a whole rant about that, but I’ve found developers in Europe especially just seemed to not be so whiny just to put it bluntly. I’m a US developer. I can say these things.
Rob: I was whining when I was a US developer too. I’ll admit it.
John: We all are. We all get so used to these tech startups. Everybody in the company treats you differently because you’re the tech guy, you know how to do all this. It’s a whole other thing, but anyway, our business changed. This was actually one of the good things about COVID.
When I started slowing down, not having more time, that’s when I found an offshore developer that really worked. You could give them your requirements, and they just were pretty self-sufficient, get the stuff done. You tell him when you want it done, and it was done by then.
Rob: That’s cool. It doesn’t always work out that way, of course, but it’s nice that you either got lucky, interviewed well, or whatever, and were able to turn that corner. Because I think, as a developer, outsourcing development can be a real challenge because I’m going to put this in quotes, “No one can ever write code as good as I can.”
This is the internal monologue of every developer ever. It is nice that you’re able to essentially get parts of that off your plate. Do you still write much code in the product, or are you just doing more technical direction at this point?
John: I do both, but I do the stuff that’s hard or tricky. We’re working on some more pricing stuff right now. I do all that stuff. I just don’t trust yet somebody else to do that. But in general, like, hey, go build these screens to do this other thing. It’s fine. They can go do that, and honestly, you got to let go at some point.
You cannot hold everybody to your standards. At the end of the day and after being an engineer for many years, it doesn’t matter. If the buttons work, there are so many big systems built with duct tape, and they work. You got to get over that as a technical founder.
Rob: Yeah, I agree. That was when I started becoming much more effective as a business owner when I learned that too, and it took me many years. It took me too long. It took me five, six years of running software projects and products. And I was still mingling in the code, still making tweaks, and eventually, I became more valuable to the companies once I outsourced my own development.
As we move towards wrapping up, I wanted to get into your free plan and raising prices once you got into TinySeed. I’m curious, Colleen, do you remember when the two of you—for folks, TinySeed, obviously, a startup accelerator for SaaS companies. You apply and then you do Zoom calls with myself, Einar, Tracy, and sometimes other folks to find out more about you and your company. We ask questions and all this stuff.
I remember, I think Einar may have talked to John, and one of the things Einar said is ScatterSpoke is awesome. They have a free plan. I’m not sure that’s a good idea. I think the pricing is messed up in essence—isn’t accurate, which is very, very common. I think most of us, probably, 70% of founders who haven’t given a lot of thought to the pricing, have screwed it up in some way or another in their product.
But then, when I was on a call with the two of you and I started digging into the numbers of like, whether the free plan converts? What’s your pricing? Do you remember one of the early things I said about the free plan? Do you remember what my general sentiment was?
Colleen: I don’t remember.
John: No.
Rob: Okay. Which is fine, it was like nine months ago. I don’t expect you to. My first thought was you need to kill the free plan. It just didn’t make sense. The numbers didn’t make sense to me. That’s not a blanket statement of free plans don’t work because that’s not true. We see free plans work, and it wasn’t a blanket statement of this will never work, but it was a first instinct of like, wow, you have that many people using it. So few are converting, and maybe it’s too permissive, which I think you guys actually knew that as we were talking.
That was something that you have since done. At this point, you have a free trial, but you can’t sign up for a free plan anymore.
Colleen: Yeah. We’re in the process right now of killing that, actually. We redid our pricing tiers first and gave everybody some grandfathered users and options with those new pricing tiers. We’re about to roll out what will essentially kill the free tier, and it was hard. I mean, it’s still a little hard for me to let go of it, and I think it’s back to being, in some ways, too close to our user base.
I feel like we built this off of people getting to try it, people who knew me, and attended my classes, workshops, or whatever being that user base. I feel like I lured them in and then now I’m like, no, you can’t use it anymore. But I think we have reached maturity as a business that it isn’t a hobby and it isn’t a free tool. We know the value is there, and that people are willing to pay for it. It’s time to grow up.
Rob: Yeah. I like that you said that it’s hard because it is. I think there is a common conversation in the MicroConf community of, hey, charge more, raise prices, and everybody’s undercharging. Most of the time, that’s honestly true, especially if you’ve never really raised prices or never looked at your pricing. That discounts the emotional side of things, both the relationship you have with your users and also the fear.
Raising prices is really scary. Killing free plans is really scary. Adding or removing a credit card before a free trial is really scary. I’ve done all of those things. Every time I’m like, I don’t know if this is going to work. If it doesn’t, maybe I’m going to make a bunch of people mad, and am I going to kill my business with this?
That is something we’ve done pretty intentionally in the first month or two of TinySeed of the batch is to say, hey, who here thinks they have a pricing issue? Again, it’s typically 70% of batch two raised their hand in the Zoom call, but then it’s to help folks think through, not only how they can actually change it mechanically and logistically, but how to deal with the emotion of that. How to convince people, hey, if this doesn’t work, it’s pretty easy to roll back. This is not an undoable decision.
Given how large of a lever—I keep saying pricing is the number one lever in any business. Especially in SaaS, where it’s recurring, pricing is your number one lever. It’s the easiest thing to change and to double growth overnight. Everything else requires more customers, requires more features, or requires something else. But just to change a number on a page and in your Stripe account and have it suddenly change it is a big deal. It deserves a lot more thought I think than most founders think.
All of that is to say how did you deal with, get through, or push through that emotional resistance? Whether it’s the fear or whether it’s just a nagging doubt of like, maybe we shouldn’t be doing this. I’m curious how you pushed through that in order to make such a drastic change.
Colleen: Honestly, once you see that Stripe account number go up and up and you see those trails convert, it’s pretty easy to support it. I think that was proof for me. I think you’re still offering. To me, we built this tool to help teams and to make this easier. I felt like I was taking that away from them by removing the free tier, but I think what you see, as you go down this path, is the value is still there. You’re just asking them to pay to get that value.
Once we start to see all the conversions, and honestly, like new enterprise contracts coming in now, I think it really just supports that the value is something worth paying for.
Rob: Awesome. We’re out of time. Thank you so much, John and Colleen, for joining me today. If folks want to keep up with you on Twitter, you’re @ScatterSpoke, and Colleen, you are @scrumhive. I like that. That’s a cool Agile Twitter handle. And then, of course, scatterspoke.com. If folks want to check out what you’ve been working on and potentially check out for doing their retrospectives. Thank you guys so much for joining me on Startups For the Rest of Us.
John: Thanks, Rob.
Rob: Thanks again to John and Colleen for joining me on the show today. If you’re interested in potentially joining TinySeed batch three, head over to tinyseed.com and get your name on our email list. I believe we’ll be opening applications again here in the next four or five months.
In addition, if you are an accredited investor and you’re interested in investing in early-stage B2B SaaS companies like ScatterSpoke and other TinySeed companies that you’ve heard on this podcast, head to tinyseed.com/thesis. You can see our unique investment thesis that we have at TinySeed, why we believe that B2B SaaS is an amazing investment, and to be able to basically index across hundreds of these SaaS companies and diversify investment is a solid way to go. You can learn more about that, tinyseed.com/thesis. Thank you so much for joining me this week. I’ll see you again next Tuesday morning.
Episode 516 | When to Re-write Your SaaS Codebase
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Matt Wensing returns for his third appearance on the podcast. He is the founder of Summit and was in TinySeed Batch 1.
We dive into Matt’s decision-making process for re-writing the entire codebase. We talk about choosing the right features to build, talking to your customers, starting with a blank slate vs templates, and much more.
The topics we cover
[06:48] How to handle customers that are not engaging
[11:35] Figuring out the right features to build
[19:24] Making the decision to re-write the codebase
[31:27] The value of forecasting
[33:18] Designing a sparse SaaS homepage
Links from the show
- Out of Beta
- Things You Should Never Do, Part I
- Episode 450 | Founder Hotseat: Matt Wensing of SimSaaS on Making Consistent, Needle-Moving Progress
- Episode 491 | Hard Lessons Learned, Reaching High-Touch Prospects, Finding Advisors, and More Listener Questions
- Episode 489 | 15 Years to a SaaS Exit (Plus Why Forecasting is Crucial)
- Summit | Twitter
- Summit | Website
- Matt Wensing | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify | Stitcher
Rob: This is Startups For The Rest Of Us episode 516. Thanks for joining me this week. As you know, every week on this show, we cover topics related to building and growing ambitious startups. But they’re ambitious yet sustainable. They’re startups that live within our life and help us help our employees, our customers, and other people who are involved. These are obviously not nonprofits, but they’re not the typical Silicon Valley startups where people are sacrificing their freedom, purpose, and relationships in order to build these companies and where fundraising can be a goal in itself.
We want to build real businesses with real customers who pay us real money. And we want to do it in a meticulous and disciplined way, in a repeatable fashion to where we could build many, many businesses in the same fashion. We don’t want to rely so much on luck like a lot of the big venture fund companies do.
This week, I’m talking with a returning guest, Matt Wensing, about when to rewrite your SaaS codebase. It’s something that he has just spent the last three or four months doing. But before we dive into that, I want to cover two talking points.
First is, you might be noticing that my co-host Emeritus Mike Taber has not been on the show in quite some time. I believe it’s been about three months. Mike and I have been chatting via email and text, and we even did a phone call today. He has stuff that’s going on that he really isn’t able to talk about in public. He has things going on that are interesting and are very likely to push his business forward in interesting ways. But when you can’t talk about it in public, it doesn’t make for an interesting podcast.
He’s still working on Bluetick. I do want to get an update from him on that and everything else that’s going on. But we both agreed that for now, he should hang tight and he’s going to let me know when the things that he is working on can essentially be discussed on the show. Then I’ll have Mike back on the show like we’ve been doing for the past year or so.
The other thing I wanted to mention is that a couple of weeks ago with TinySeed, we launched our investment pieces moving forward. It’s for fun too and beyond. But the idea is that we believe investing broadly into the earliest stages of B2B SaaS companies, and specifically, it’s the B2B SaaS companies who are not necessarily reliant on traditional venture capital racket. It’s the Startups For The Rest Of Us, the MicroConf type companies. But we believe this can provide amazing returns for investors and thus allows us to raise more money and help more campiness.
There’s this huge gap in the funding market that’s why we launched TinySeed back in 2018. That’s why we’re continuing to double down in this space, as I have been for 15 years with the blog, more than a decade with the podcast, and 9 years (almost going on 10) here with MicroConf. But it’s to help more founders get there faster. Some founders get tremendous value out of a free podcast. Some get value out of a $20 book or $10 ebook. And some get value out of attending in-person events, meeting people, hearing tactics and tips, and building relationships. Others do want to take that other step of hey, here’s some funding; here’s a batch approach; and here’s a network, mentorship, and all that.
There are many different paths for folks to get there. I think about it as being bootstrapped, almost bootstrapped, or mostly bootstrapped as I’ve heard Craig Hewitt throughout on his podcast a few times. But the idea is there’s this huge gap between raising millions or tens of millions in funding and going after that unicorn exit. The companies that we talk about on this podcast and that are part of the MicroConf community of building these ambitious yet sane startups.
If you are an investor, if you’re credited, or you fit the definition of a US accredited investor—you do not have to live in the US—I encourage you to check out tinyseed.com/thesis. Because we have a bunch of data that we have crunched and spent weeks and weeks writing this massive report. It’s an investment memo that has become our investment thesis. We have essentially been proving that out with our first two batches, and we’re in the process of raising Fund 2, so that we can continue to help, support, mentor, guide, and fund hundreds and hundreds more independent SaaS companies. Again, that’s tinyseed.com/thesis.
If you decide to invest, you’ll be joining folks like Dharmesh Shah—co-founder of HubSpot, Rand Fishkin—founder of SparkToro, Steli Efti—co-founder of close.com, and Patrick McKenzie—who many of you know as patio11 on the internet.
As I mentioned earlier, today, I’m talking with Matt Wensing. He’s the founder of Summit. He’s been on the show a couple of times. I believe this is his third appearance. He is the co-host of the Out of Beta podcast. Man, I talk about a bunch of stuff about what he’s been up to in the past six, seven months since he was last on the show.
One of the topics we do dig into is why he decided to rewrite his entire codebase—whether that was worth it, things he might do differently in the future, and how he made that decision. We also cover how he’s getting growth, how he has been doing customer development. Just all kinds of stuff. It’s a great conversation. I hope you enjoy it. Let’s dive in.
Matt Wensing, thank you so much for joining me on the show again.
Matt: Mr. Walling, thanks for having me.
Rob: Absolutely, man. It’s good to have you back. As some folks may remember, you were on the podcast back in March, episode 489—15 Years to a SaaS Exit (Plus Why Forecasting is Crucial). In that episode, we talked through the building and growing Riskpulse and then selling it back in 2019 for a very nice exit. And then we talked—towards the end of that episode—about Summit, which is the SaaS app—the startup that you’ve been working on now for a year and a half?
Matt: Yeah. That’s about right.
Rob: You’re part of TinySeed Batch 1. Your h1 is tell your forecasting spreadsheet you’re never getting back together. Design your business with someone instead. You’re about forecasting. We talked in the last episode about how if you go into a Baremetrics, ChartMogul, or ProfitWell it is everything up until today. It’s your backward-looking metrics. Those are obviously very important to be looking at. Summit takes it from there, and then you’re going to extrapolate ahead using—we talked about Monte Carlo very lightly. But it’s just simulations and things like, hey, this is where you’re headed based on where you’ve come from.
Is that a pretty good assessment so far?
Matt: That is excellent.
Rob: Awesome. Folks may recognize your voice—co-host of the Out of Beta podcast with our mutual friend Peter, Suhm. I guess you’re @mattwensing on Twitter.
Matt: That’s right. You can find me there. I tweet way too much. But you can help me do that even more.
Rob: Indeed. Go follow Matt to encourage him to spend more time on Twitter and less time working on his company. Several interesting things I want to dig into today. I think we’re going to talk some point about your homepage at Summit. It’s at usesummit.com, and folks can check it out. It’s very sparse. It’s a headline, a tagline, and then buttons and that’s it. It’s not the typical SaaS homepage.
But before we dive into that, I want to go from where we left off back in March in the sense that you were in early access. You had a few customers paying you something. You did not have the traction that you wanted, but you were moving in that direction. You had people coming in, signing up for trials, and connecting their metrics. It didn’t seem like things were working in the sense that you weren’t growing month over month the way that you might expect.
People were trying it out and again, wiring up metrics, but they weren’t sticking around. Most people weren’t paying. The majority of people were not getting the value out of it. Talk to me about where you were because a lot of folks listening to this episode have been in that position or are in that position now. Where they’ve built something, and they know there is something there. It’s not just a complete failure. People are intrigued by it and they try it out, but they don’t stick around. They don’t pay. I just want to hear mentally where you were and what that looked like from your perspective as a founder.
Matt: Yeah. We can definitely relive that. It’s funny, it didn’t feel like a pain when I was there because some things were good. I was getting feedback from people that really, frankly, loved the app, but they just weren’t enough of them. Just to jump ahead to what I learned and then we could talk about how I missed it and then how I finally realized it. Maybe I got the target persona wrong. I didn’t know that I got it wrong. Actually, the target persona was actually the later stage. It’s a bit of concrete terms.
I launched the Summit as an app called SimSaaS. I was thinking, let me help the very, very early stage founder figure out how to do a forecast without the use of something like Google Sheets. I’m going to bring a load of technology to bear on it and make it just a killer app where you could just enter 20 numbers and hit a big button (literally) and get an answer. It did that. It delivered on that promise. For the users, the earliest stage founders that had nothing, nothing at all—no spreadsheet—just thoughts and ideas. It worked.
The problem was something happens as time goes by. Those founders grow up, their businesses mature, and their needs evolve—that’s one part. The other part is they get used to the app as it is, and then just like with every other app, they want more. The app as it was yesterday—even for those happy users—once they are happy, that’s great. Jeff Bezos calls it that wonderful human discontent or something. People are always coming back for what’s the new thing, how can I do more stuff with this, or can it also do that.
I was building up two things. One was this eroding usage that wasn’t going away. Even my free retention—because it was a premium product—wasn’t good. I didn’t like the direction it was going. People would have these experiences, but then they weren’t engaging frequently enough to turn them into a paying customer. But the other part was even the people that loved it had a wish list of things that would really get them excited and really push them over the line. Maybe even turn them into a paying customer.
I’m a one man team—I shouldn’t say that actually anymore. I’m a one man team currently with a handful of contractors. That just put me at a crossroads of I’ve got this codebase that I’ve been working on for a year. It’s a core and then there’s a front-end and a back-end (let’s call it that). The back-end is really unique, really hard to build, the kind of thing you hope you never have to do again. The front-end was like bootstrap and pretty basic components and tools. I tried to pick colors, but it wasn’t amazing. It was good enough.
I just hit this crossroads though. To your question, where have I gone wrong in terms of why can’t I keep these people around, and why can’t I fully satisfy their wish list? Maybe not 100% because I think that’s almost impossible. Why is it increasingly hard to build the next thing that somebody asks me for, and what does that mean for my business? Those were the questions I was facing in February and March.
Rob: It was pretty obvious to you just that people were not engaging and not paying. It’s never obvious what you do then. It’s never obvious what you build. How did you get to that point? I guess that end of the story is that you have a lot more traction now, growth has started kicking up, and people are getting value out of it. Here we are in August six months later. We know that you made a good decision. You changed the product enough that you do have traction now. How did you figure out what to build? Was it conversations with the customers or something else?
Matt: Yeah. I was thinking about this. We’re always looking, as founders, for validation. I know I am. I think most of us are. When people say things that are complementary, they just tend to really put wind in our sails (pick your metaphor). It feels great and you remember those things. There’s a bit of a bias towards the evidence that you’re on the right track. But then, as I said, there was this mounting evidence that I wasn’t on the right track like something was wrong.
I really said I’ve got to start piecing together the consistent story that I’m hearing from the users that I really want to have. Whether it’s people that are on the verge, but the app just isn’t good enough, or maybe they’re people who love the app and then fell out of love with it because it wasn’t good enough. A deep look or maybe a scary look at that evidence and that feedback and saying, what product do these people actually need?
A little bit of context is helpful, and this sounds a little counter-intuitive. I was able to raise another round of funding right around the same timeframe—February. It was based on the traction that I had with the first version of the product. Again, what investors were seeing, what I was seeing was there is clearly a demand for this. People are paying. You are getting users. They’re coming in. Something’s not quite right, but at least the kindling is there.
I think you and Einar, when you invested through TinySeed, were really betting on me as a person and a proof of concept. I think these people were saying, proof of concept has proven out, hasn’t quite figured out the customer yet—the monetization yet, but were willing to bet that Matt’s on to something. I think it’s important to say that that way in March frankly as the world was shutting down to say, wow, I’ve got 12 months plus of runway suddenly where I don’t have to worry about revenue. I’ve got a bunch of data from customers. Now is not the time to do incremental stuff. Or better said, now is an opportunity to do something big.
If I’m going to do something big now, making big changes now, and then seeing how that goes over the next 12 months is better than, oh, I’ll make incremental changes the next 9 months. Burn through a bunch of this new runway, and then find out that I needed to make big changes. I chose to flip it around and say, let me really go back to basics and build against the feedback that I’m getting from this user, this user, and these users because that’s the market I want. Those are the people I want to satisfy.
It’s just being deliberate about who I wanted to please and then being honest that it wasn’t good enough for them. The third factor—which I think is the most important in deciding to do the rewrite—was I’ve got the time. I potentially have the focus because suddenly the world shut down. If I can figure out how to work at home with four kids and a family all stuffed into this house together, then maybe I can basically chain myself to my desk for the next 60 days and do something big. Take a big risk.
Rob: It sounds like you were listening to customers. Would you say it was a job to be done? That in your head, the job of Summit is to do X. That you found that you had built it to do the wrong job? Does that metaphor work?
Matt: Yeah. Actually, I like it. I can use that as a start. I thought my hypothesis was that the job of Summit was to create a forecast for people. If you don’t have a forecast, you’re going to hit that button after putting in a few numbers and you’re going to get a forecast. In terms of a vending machine approach where you punch the Coke button and out comes a Coke. It worked.
The problem was, it would come out and people were like, oh, well, I really like Diet, I like Cherry, or I want mine with a splash of orange. I took a step back and I said, what are these people actually saying? Because you can go a little crazy as a founder when you get feedback of okay, I need to build a citrus flavor dispenser feature onto this. And then these people could be happy.
But what I found was that the things they wanted have nothing in common. What they had in common was they all wanted something else. If you think about that, the North Star became flexible. Like, oh, oh my. I have built a very inflexible vending machine. You come here, if you want A4, A5, you’re good. I can’t do anything else for you. These are your only two choices. The reason that I had to go so deep in terms of rewriting the product was I realized that I was competing against Microsoft Excel—and many of us are.
The difficult thing about competing against a spreadsheet—and probably other products like that—is that a spreadsheet is just endlessly flexible. There’s nothing you can’t do in a spreadsheet. They were coming to me with that same mentality of I’m not used to being constrained like this. I need to be able to copy this thing, add this thing, and do this thing. That need for flexibility, the job to be done was to provide them with a flexible canvas (if you will) or flexible blank space. That’s what I had to do for people.
Once I realized that. I was like, okay, the current version of Summit is not that. I started by ripping the front off the vending machine and saying, grab whatever you need. It’s all open season. And then I just kept going. It’s like a house remodeling project. Sometimes you don’t know when to stop. You just keep going and going and going.
I remember I got to the point where I had rewritten the front-end. I live-tweeted this. I worked in public to do this piece. I rewrote the front-end, but the back-end wasn’t different. I remember pausing and asking myself, okay, the front-end is a lot more flexible. You can click a lot more things and rearrange things. It’s a dashboard tool that’s a lot more modern. Is that all that they needed?
Kind of had this moment where you’re standing at that river and I just went for it. I said, no, actually, I think they need the back-end calculations to also be much more flexible. I basically open that up as well now. With the current version of Summit, not only is the front-end a more flexible, adjustable kind of workspace. The back-end also is just endlessly customizable. That was it. That was the breakthrough that I needed, not to say it wasn’t scary.
Rob: That was the thing. I’ll say there is a rule of thumb of perhaps it’s a yellow or red flag when a developer says we need to rewrite the whole codebase. It’s always, well, of course, we always want to rewrite the whole codebase because either someone else wrote it and it’s not as good as the code that I’m going to write. Or I wrote it a year or two ago. I was learning this stuff. It’s pretty crappy. I think I feel like that about most projects that I code. I want to rewrite them. It’s like, oh, there’s all these hacks and stuff.
Even going back to probably 15, 20 years, there was an essay by Joel Spolsky on the Joel on Software blog. It’s like never rewrite your codebase and this and that. It’s not never, but I always push back. I’m 35 Angel and TinySeed investments in, and I’ve had at least 4 or 5 of the startups that I advise or interact with, say, we need to rewrite our codebase. Every time I really push on it. How do you know? Why? Oh, you got a new CTO. Yeah, not a surprise. He wants to rewrite the codebase. Oh, he wants to change frameworks too, keep the same language? Yeah, of course he does because that’s his favorite framework. It’s this and that.
Sometimes it is the right decision, but it really needs to be thought through carefully. You and I may have had that conversation. I don’t even recall, to be honest. Did you put a ton of time into thinking of do I really want to do this? Because if I recall, it was about 60 days, 70 days of effort. Did you just say, you know what, I have the time. I’m just not going to think that much about it. I’m just going to crank through and do this.
Matt: Yeah. I’ve got good friends and mentors and definitely heard that feedback. I think you might have sent me an email saying, just in general, that’s not a good idea, but I trust you. There was definitely that voice on my shoulder. What was hard for me to communicate—because I’m a 1.75 person crew, let’s just say 1 man crew—at the time is we all wear many hats as founders. Especially in the early days, you wear all the hats.
The hat I was wearing when I said I wanted to do the rewrite, I’ve got a geek in me. Don’t get me wrong, but it wasn’t the inner geek saying, oh man, I want this to be faster, better, or a new framework. It wasn’t the shiny object syndrome developer in me. It really was the business strategist, the founder that said, I want a product that I can be proud of. That when I do a demo, I’m looking forward to those demos. I know people are going to be happy instead of knowing that they’re going to say, oh, well, I need these six things. I need to satisfy this need in the market that’s being expressed by these people.
It was really a lot more of—it sounds weird, but it was—the sales and marketing-driven decision to say I’m not doing this for performance’s sake to eke out another 10%. I’m not even doing this for the framework’s sake. I’m doing this so that when I do a demo with somebody, it blows them away, and they buy the thing. I’ve lived in that situation before—doing sales of things where there’s just all these shortcomings. You don’t always have to go back and rewrite things. Sometimes you just need to tell the customer, hey, sorry. It’s just not a good fit for you right now. It’s on the road map. We’ll let you know when we get to it.
But I made the executive decision—as you have the luxury of doing in the early days—to say, no, I’m the CEO and founder. There’s enough evidence here coming from my inner salesperson to say, this is not just the right product. We need to rewrite it. It was my inner CEO going, hey, developer Matt. Guess what you’re going to do. You’ve got a job to do. You better roll up your sleeves and learn Vue.js, Hasura, and a whole bunch of new tech because you’re going to want to do all these things.
Of course, I let myself have fun. Don’t get me wrong. It was a blast. I really felt like I was hiring my developer self to do a job. Not my developer was like, oh, I have an idea. We should do this. I think that just comes through experience. Not to say I’m perfect, but you got to be really honest with yourself about where your motivation is coming from to do something like that.
Rob: That’s a really good point for folks to think about. If you’re a single founder, a two-founder team and you are thinking about rewriting, put on your sales and marketing hat, put on your CEO hat, not your CTO or developer hat. Not that there’s never a reason. You can have a code that is so bad that you can’t add features and it takes you a month to do a day’s worth of work or whatever. Of course, that happens, but it’s a lot less frequent than developers tend to make it out to be. Knowing that it came from that sales and marketing perspective. It truly was almost needed to be a different product. Summit 2.0 is really, really different from Summit 1.0.
Matt: Yeah, completely. You can actually build Summit 1.0 using Summit 2.0. If that doesn’t bend people’s minds. Summit 1.0 was just one template now in the new world. One other thing is that the CTO did speak up a little bit in that time. The one thing I told Peter this on the podcast was, I want to build this in a way where if it is successful, I can hire developers to help me get it on the next level and the next level. Because the first version was one of those things where I got to build this thing by hook or crook. It doesn’t matter what the code looks like. Just get the date on the screen, try to sell some subscriptions, and test the interest.
With this one, I said, I have a pretty good feeling this is going to be well-received. Let me take a little bit longer, maybe two, three, four, five weeks longer. Which is, again, doubling the timeframe but I’ve got the time. Let me make sure that what I come out with is something where I can at least turn to a skilled dev and say, hey, the market likes this. Can you take over these parts now? Because this is the foundation. This is not a throwaway, basically. That was maybe a concise way to say. My inner CTO was like, don’t have it be thrown away. If we’re going to do this, at least do it in a way where we don’t have to scrap it again because we don’t want to do this again.
I did follow that. I think that’s worked out pretty well, fortunately. I’ve had other developers contribute since then. It’s moving faster now because of that.
Rob: That’s really nice. How long did the rewrite take you?
Matt: I think 70 days of coding. Essentially with the commit and push every day.
Rob: Oh wow. That’s a great way to do it.
Matt: Yeah. It was very consistent. Actually, that was fun. You can look at my GitHub or I can at least look at my GitHub repost. You can see where my consistent deployments or pushes died off and I became very sporadic in terms of my product progress with the first version. Because I was hitting these walls to do the next feature. It just required a bigger effort, a bigger effort, and a bigger effort.
I was like, okay, time to brew the coffee and crank out this feature. It’s going to be super hard to do, and I would get these bursts of productivity. With the new one, it’s actually nice to see a quantitative self. You can see, hey, look at that. Every day, something new—a little bit better, a little bit better. That also helped me know that I was on the right track. It wasn’t halfway across, but still, nothing delivered that kind of project.
Rob: I’m looking at your revenue graph. As I mentioned earlier, you’re a TinySeed batch one company, so I have access to that kind of stuff. There is a really noticeable uptick in your MRR. Of course, I’m trying to scroll through it now. It looks like from June to July, your revenue ticked up. You’re still early stage (so folks know). But there was a doubling or something of MRR, and then it went up another whatever. Is that because of V2? Is this rewrite instantly resonated with people that noticeably?
Matt: Yeah. I think the short answer is yes, but I’ll qualify that by saying, I took it then to the customers that I was essentially targeting with this rewrite. I took it to them basically as soon as it was ready and I said, aha. Here is the flexibility you’ve been asking for. Here is the tool. I know it’s not done yet, it’s not 100%, so I want your list. But if you agree this is on the right track, I would love your support. I would love you to buy into it because I think this is what you’ve been looking for. I was successful in those sales, which felt great. Obviously, that was a huge validation.
It wasn’t really the numbers, so much as saying, wow, out of these three or four companies or founders that are in my sweet spot—the ones I really want to please—they bought. That was huge. Who knows? With the old version, I’m sure I would’ve sold some subscriptions as well. But again, back to the personas, it would have been to these people. It would have been to those other people. That was not what I ultimately wanted to do.
Rob: Right. Now, I logged into a brand-new Summit account. The first thing that pops up, it says, welcome to Summit, the software to replace your financial spreadsheet. And then you have three different pre-built models. You have self-service SaaS, early-stage SaaS, sales-driven SaaS, and then you have upload your own model.
I’m guessing that in Summit V1, one of these models was the default and you were limited with assumptions in there versus this is a meta-level where it’s a much more of an Excel. I can build whatever I want.
Matt: Yeah. It really is. It’s more like maybe a Lego bucket at this point where you can build a model, build your house. Here are all the pieces. Here’re the building blocks. The first version was more like, here’s a Lego kit. It only builds this kind of house. I hope that you live in a ranch home, and you can adjust a few things about it. How big is your garage, and how big is this. You can make some changes, but it wasn’t the kind of thing like, here’s a bucket of parts. That bucket of parts approach is where what the screen you’re looking at right now is essentially saying, here are five kits. You can pick one or three kits and you can pick one.
That’s nice too because you gave me some really good feedback. That wasn’t always there. That wasn’t actually there at the very beginning of the relaunch. What you said, and I think it ran through is, oh man, a blank slate is just really tough. This is interesting to go through. I pushed back on that at first. I remembered getting your email and thinking, I don’t know if he gets it yet. There’s all this flexibility now. I don’t want to preload stuff. That takes it away.
A lot of people face this blank slate problem with the SaaS app is what do I fill it with? I was worried that if I automatically put in a bunch of building blocks, you would come to that same conclusion of like, oh, look at that. This isn’t for me because this is assuming that I’ve got a sales team, or this is assuming that I’m self-service or whatever.
It’s really silly. But I just remembered back to Microsoft Excel, for example, or Microsoft Word, and what happens when you load up those applications? You get hit with this screen and it says, are you trying to do an invoice? Are you trying to do a short story or an essay? It has all these templates.
I just had this mental breakthrough of like, oh yeah, duh. I can just show them a list of options and they can pick one. That then gives me the best of both worlds. If you want a blank slate, man, you can have it. But if you’re an early-stage founder, and you see early-stage SaaS in there, you can just click it. Then, hopefully, that gets you started faster.
Rob: The beauty of that is not even that you have to use it as is, but when you click it, it prepopulates a bunch of stuff and I then I can go tweak it. That’s what we learned when we’re building Drip was you have this workflow builder. Which is this visual designer and you can do if then else statements. It’s […] complete language in this visual builder for email. People were the experts, the power users, the Bren and Duns loved it.
Everyone below that level—even mid-level marketers—were like, I don’t know what to do first. What should I do? It wasn’t until we got the blueprints built and you could just one-click import a blueprint that we really started getting the mid-level and lower end marketers. I think that’s probably where my feedback came from is having built a similar engine that Derrick and I knew the workflow builder is incredibly powerful. So cool when we launched it. Quickly, all those questions of oh, what should I do? It was like, I guess we got to show you some guidance.
Matt: Yeah, absolutely. That’s my job now. This is kind of a retrospective. There is a group of users of the first product that I essentially alienated. They came to the new one and basically said, what have you done? You took away the one I liked, and you replaced it with this power tool. I don’t know what to do. It was pretty painful to hear. It’s nothing more satisfying as a product person and to hear that somebody loved the thing you made. But I wasn’t going to keep that around.
What I’m trying to do now is through Looms, education, those templates, and blueprints, I’m just building up a community. I really do want to work backward now and say, you can still use this. There’s going to be some learning. This is now more like a Drip or that kind of power tool. You have to decide that you want to be good at this and learn a new skill to an extent, but it’s still better than Excel. You’re going to like it more than Excel, but there is a learning curve. That’s fine. That appeals to me. Frankly, I really enjoy the subject so much that I enjoy teaching people how to use it.
Rob: That makes a lot of sense. We talked last time about the value of forecasting in SaaS in terms of when to use cases, fundraising, to see when your money’s going to run out. But if you’re a bootstrapper—which you most likely are listening to this—show hiring is a big one. Ad budgets, like, hey, ads are starting to work. Can I throw $5,000, $10,000 a month at it? Or will I run out of cash just because of my LTV pans out? If it takes me six months to get paid back, I need X amount of cash.
Yeah, you could model that in Excel, but this is going to take everything into account. There’s ad spend, there’s any of those big decisions around spending money in a way that is complicated and can put you in a cash crunch.
Matt: Yeah. What’s nice about a model approach instead of a spreadsheet is you set a founder in front of a spreadsheet and you say, put your business in here. There’s an immediate thought of okay, I need a revenue row, I guess, and I also need an expenses row. And then I need this, I need that. They start to fill out that classic spreadsheet template view of the month over a month like what you see in QuickBooks.
What’s interesting about this, and I’m still flushing this out, but I’m really just asking you to tell me about your business. Tell me what your revenue plans are, what your acquisitions channels are, and what your team looks like. Founders are really good at that. You can just ask a founder like, how do you acquire your customers? Oh, we have Google Ads spent. Cool, let me capture that real quick, done.
The hope is that it’s really a more natural way to capture business is this model. Where to sketch your home on a piece of paper on a napkin is easier than necessarily going through and saying what are all the dimensions and all these different things. Which people can seize up. That’s the test right now is to see how many folks can come to this and essentially describe their businesses and get out something that is really useful in making decisions.
Rob: As we move towards wrapping up, we got to talk about this homepage because it is one of the most compact, sparse. I think there is a total of 15, 16 words on it, not including your copyright at the bottom. It’s your logo. It’s a picture of a hummingbird, which is pretty cool. Then it’s, tell your forecasting spreadsheet you’re never getting back together. Design your business with Summit instead. There’s a button to create a free account. There’s a button to sign in.
I have seen creative SaaS homepages. Obviously, the standard one with pricing on it, or maybe that’s another link. There’s a top nav, which you don’t have. You have no footer. I once did a long-form sales page. The Drip homepage was a long-form sales page for quite some time, but I’m not sure that I have seen one like this. I’m curious if you have inspiration, or if you just did it on a whim. The real question is, is it working, or do you know yet?
Matt: Yeah. That was definitely done because I needed a homepage. I was launching a new thing. It was a complete rewriting, including the marketing site. I just needed to get something out there that had those buttons. To be perfectly honest, what’s the minimum? It’s probably an h1, h2, login, and sign up buttons. That’s what it is. I have not prioritized adding to that for a couple of reasons.
One is, I’m still figuring out what Summit is. Not to be totally metaphysical, but what is this thing? I have a little bit of a concern that if I flush that out with a lot of words, first of all, that’s changing. I’m still figuring it out. Second of all, I got to update and maintain that stuff. There’s a bit of a liability that goes along with adding more words to that homepage.
The second part of it, which I will defend for different reasons. Maybe I’m just defending past actions because I have convenient data. But it’s working well enough. Through that homepage, it depends on the day, but I’m getting anywhere from—on a very, very slow day, maybe it’s a Sunday holiday or something like that—2-3 sign-ups. On a busy day, 10, 12, 15, 20 sign-ups through that page. That tells me something. It tells me that those are high intent people. They just wanted to get in and check it out.
I think, for now, honestly, I don’t feel ready to convince more people—people that are on the fence where they’re like, I don’t know if I need to tell my forecasting spreadsheet goodbye. I’m pretty happy with it, I don’t have a forecasting spreadsheet, or I don’t have any context. Those people, I’ll lure them in, I’ll bring them in, and tractor beam them in eventually. But for now, I like knowing that the people that get into the product are there because they’re motivated, what they did see resonated with them, or they heard about it some other way. That’s good enough for now because the feedback I get from those 5, 6, or 10 sign-ups per day is a good signal.
For what it’s worth, I actually think that’s about to end. I’m not hearing a lot of new things these days from these sign-ups. I think it’s really natural to go back to that homepage and say, jeez, Matt. You could probably widen your funnel here if you just helped a few more people realize that oh, that’s what this does. I see this as an opportunity. I haven’t prioritized widening the top of the funnel yet. But I will. I definitely will.
I’m actually investing a pretty good amount of time in business development and partnerships for Q3 and Q4 to give a lot more people to that homepage. I fully intend to give them a little bit more insight into what it is.
Rob: No. That makes sense. I think there is a certain benefit to simplicity, especially in the short term. That’s cool to hear that’s your thought process and that is what you’re experiencing. I certainly can attest to I had a tool. I ran a SaaS up before Drip called HitTail, and it’s a long tail SEO keyword tool that plugged into your Google webmaster tool or something. And it pulled out the search console—they kept changing the name of it. But it would pull out keywords that you should rank high for based on your content and based on how people are finding you. But you weren’t ranking high enough. You were on the second page of Google. It would suggest them as things to beef up to get to the first page.
The way that I sold it, and I found that it really resonated, was a curiosity headline of how the tool works. It’s analyzed over a billion keywords in its lifetime across thousands and thousands of websites. It will suggest the keywords that you should be ranking for but aren’t. It didn’t go into how it did it. Once you got in the tool, you can figure out what it was doing. But it was really a curiosity play of this is the job it does, these are the testimonials, and these people are saying it works.
When you first arrived at the site, people would have skepticism. Does this thing actually work? Is it worth the money? Is it going to waste my time and all that? But that curiosity play was enough to get a lot of sign-ups—really high trials to paid conversion rate. I can imagine with you this headline, like you said, if someone came here totally cold, and they don’t really know what this is, or they don’t have the context in, I’m not sure it’s enough to draw them in. As you said, if you’re into forecasting and you really don’t like the spreadsheet, the headline captures it, and that’s enough. That is an interesting approach in this early stage.
Matt: Yeah. I felt a little bit more justified when Hiten Shah, who’s a TinySeed mentor, came and shared with the group. He’s now running usefyi.com or FYI. That was my inspiration for this. If he can get away with it, and it’s literally just an h1 and then a button. I don’t know how that’s going for him, what his plans are, I’m not speaking to that. But I saw it and said, okay, here’s a guy who knows a thing or two about heatmaps, homepages, and actions.
The one thing that resonated with me or I took away from that was what’s the thing you want them to do when they’re here? With his, it’s sign in with Google. With mine, it’s I want you to create an account. It was just a great point of man, if you know the next action you want them to take, maybe it’s okay to just start by focusing on that.
Rob: All right. Before you launch an app, if you put up a landing page and drive traffic to where, or whatever, it’s very simple that landing page. Typically, it’s a headline, a short description, and an email caption format. That’s the standard format of it. You can get those to convert really high—10%, 20%, 30% of visitors. If they’re targeted, you have a good headline, and good curiosity created out of that, you can land a lot of folks.
I think there is something to that simplicity. My guess is with Hiten’s, he’s not doing something if it’s not working. I’m guessing that’s a pretty, pretty decent approach. Sir, thank you so much for coming back on Startups For The Rest Of Us. As I said at the top of the show, you are @mattwensing on Twitter and usesummit.com if folks want to check out what you’ve been up to and potentially forecast their SaaS with V2.
Matt: Awesome. Thanks for having me on, Rob.
Rob: Absolutely, man. Thanks. Thanks again to Matt for coming back on the show. If you enjoyed this episode, I really appreciate it if you would check the Startups pod Twitter feed, and you can @ reply because Matt and I both have been mentioned in the tweet that came out this morning or retweet, or whatever. Just let us know any piece of that conversation that you enjoyed or get value out of, and you feel like you’ll take with you as you go ahead in the coming weeks. Thank you so much for listening, and I’ll talk to you again next Tuesday morning.
We want to build real businesses with real customers who pay us real money. And we want to do it in a meticulous and disciplined way, in a repeatable fashion to where we could build many, many businesses in the same fashion. We don’t want to rely so much on luck like a lot of the big venture fund companies do.
This week, I’m talking with a returning guest, Matt Wensing, about when to rewrite your SaaS codebase. It’s something that he has just spent the last three or four months doing. But before we dive into that, I want to cover two talking points.
First is, you might be noticing that my co-host Emeritus Mike Taber has not been on the show in quite some time. I believe it’s been about three months. Mike and I have been chatting via email and text, and we even did a phone call today. He has stuff that’s going on that he really isn’t able to talk about in public. He has things going on that are interesting and are very likely to push his business forward in interesting ways. But when you can’t talk about it in public, it doesn’t make for an interesting podcast.
He’s still working on Bluetick. I do want to get an update from him on that and everything else that’s going on. But we both agreed that for now, he should hang tight and he’s going to let me know when the things that he is working on can essentially be discussed on the show. Then I’ll have Mike back on the show like we’ve been doing for the past year or so.
The other thing I wanted to mention is that a couple of weeks ago with TinySeed, we launched our investment pieces moving forward. It’s for fun too and beyond. But the idea is that we believe investing broadly into the earliest stages of B2B SaaS companies, and specifically, it’s the B2B SaaS companies who are not necessarily reliant on traditional venture capital racket. It’s the Startups For The Rest Of Us, the MicroConf type companies. But we believe this can provide amazing returns for investors and thus allows us to raise more money and help more campiness.
There’s this huge gap in the funding market that’s why we launched TinySeed back in 2018. That’s why we’re continuing to double down in this space, as I have been for 15 years with the blog, more than a decade with the podcast, and 9 years (almost going on 10) here with MicroConf. But it’s to help more founders get there faster. Some founders get tremendous value out of a free podcast. Some get value out of a $20 book or $10 ebook. And some get value out of attending in-person events, meeting people, hearing tactics and tips, and building relationships. Others do want to take that other step of hey, here’s some funding; here’s a batch approach; and here’s a network, mentorship, and all that.
There are many different paths for folks to get there. I think about it as being bootstrapped, almost bootstrapped, or mostly bootstrapped as I’ve heard Craig Hewitt throughout on his podcast a few times. But the idea is there’s this huge gap between raising millions or tens of millions in funding and going after that unicorn exit. The companies that we talk about on this podcast and that are part of the MicroConf community of building these ambitious yet sane startups.
If you are an investor, if you’re credited, or you fit the definition of a US accredited investor—you do not have to live in the US—I encourage you to check out tinyseed.com/thesis. Because we have a bunch of data that we have crunched and spent weeks and weeks writing this massive report. It’s an investment memo that has become our investment thesis. We have essentially been proving that out with our first two batches, and we’re in the process of raising Fund 2, so that we can continue to help, support, mentor, guide, and fund hundreds and hundreds more independent SaaS companies. Again, that’s tinyseed.com/thesis.
If you decide to invest, you’ll be joining folks like Dharmesh Shah—co-founder of HubSpot, Rand Fishkin—founder of SparkToro, Steli Efti—co-founder of close.com, and Patrick McKenzie—who many of you know as patio11 on the internet.
As I mentioned earlier, today, I’m talking with Matt Wensing. He’s the founder of Summit. He’s been on the show a couple of times. I believe this is his third appearance. He is the co-host of the Out of Beta podcast. Man, I talk about a bunch of stuff about what he’s been up to in the past six, seven months since he was last on the show.
One of the topics we do dig into is why he decided to rewrite his entire codebase—whether that was worth it, things he might do differently in the future, and how he made that decision. We also cover how he’s getting growth, how he has been doing customer development. Just all kinds of stuff. It’s a great conversation. I hope you enjoy it. Let’s dive in.
Matt Wensing, thank you so much for joining me on the show again.
Matt: Mr. Walling, thanks for having me.
Rob: Absolutely, man. It’s good to have you back. As some folks may remember, you were on the podcast back in March, episode 489—15 Years to a SaaS Exit (Plus Why Forecasting is Crucial). In that episode, we talked through the building and growing Riskpulse and then selling it back in 2019 for a very nice exit. And then we talked—towards the end of that episode—about Summit, which is the SaaS app—the startup that you’ve been working on now for a year and a half?
Matt: Yeah. That’s about right.
Rob: You’re part of TinySeed Batch 1. Your h1 is tell your forecasting spreadsheet you’re never getting back together. Design your business with someone instead. You’re about forecasting. We talked in the last episode about how if you go into a Baremetrics, ChartMogul, or ProfitWell it is everything up until today. It’s your backward-looking metrics. Those are obviously very important to be looking at. Summit takes it from there, and then you’re going to extrapolate ahead using—we talked about Monte Carlo very lightly. But it’s just simulations and things like, hey, this is where you’re headed based on where you’ve come from.
Is that a pretty good assessment so far?
Matt: That is excellent.
Rob: Awesome. Folks may recognize your voice—co-host of the Out of Beta podcast with our mutual friend Peter, Suhm. I guess you’re @mattwensing on Twitter.
Matt: That’s right. You can find me there. I tweet way too much. But you can help me do that even more.
Rob: Indeed. Go follow Matt to encourage him to spend more time on Twitter and less time working on his company. Several interesting things I want to dig into today. I think we’re going to talk some point about your homepage at Summit. It’s at usesummit.com, and folks can check it out. It’s very sparse. It’s a headline, a tagline, and then buttons and that’s it. It’s not the typical SaaS homepage.
But before we dive into that, I want to go from where we left off back in March in the sense that you were in early access. You had a few customers paying you something. You did not have the traction that you wanted, but you were moving in that direction. You had people coming in, signing up for trials, and connecting their metrics. It didn’t seem like things were working in the sense that you weren’t growing month over month the way that you might expect.
People were trying it out and again, wiring up metrics, but they weren’t sticking around. Most people weren’t paying. The majority of people were not getting the value out of it. Talk to me about where you were because a lot of folks listening to this episode have been in that position or are in that position now. Where they’ve built something, and they know there is something there. It’s not just a complete failure. People are intrigued by it and they try it out, but they don’t stick around. They don’t pay. I just want to hear mentally where you were and what that looked like from your perspective as a founder.
Matt: Yeah. We can definitely relive that. It’s funny, it didn’t feel like a pain when I was there because some things were good. I was getting feedback from people that really, frankly, loved the app, but they just weren’t enough of them. Just to jump ahead to what I learned and then we could talk about how I missed it and then how I finally realized it. Maybe I got the target persona wrong. I didn’t know that I got it wrong. Actually, the target persona was actually the later stage. It’s a bit of concrete terms.
I launched the Summit as an app called SimSaaS. I was thinking, let me help the very, very early stage founder figure out how to do a forecast without the use of something like Google Sheets. I’m going to bring a load of technology to bear on it and make it just a killer app where you could just enter 20 numbers and hit a big button (literally) and get an answer. It did that. It delivered on that promise. For the users, the earliest stage founders that had nothing, nothing at all—no spreadsheet—just thoughts and ideas. It worked.
The problem was something happens as time goes by. Those founders grow up, their businesses mature, and their needs evolve—that’s one part. The other part is they get used to the app as it is, and then just like with every other app, they want more. The app as it was yesterday—even for those happy users—once they are happy, that’s great. Jeff Bezos calls it that wonderful human discontent or something. People are always coming back for what’s the new thing, how can I do more stuff with this, or can it also do that.
I was building up two things. One was this eroding usage that wasn’t going away. Even my free retention—because it was a premium product—wasn’t good. I didn’t like the direction it was going. People would have these experiences, but then they weren’t engaging frequently enough to turn them into a paying customer. But the other part was even the people that loved it had a wish list of things that would really get them excited and really push them over the line. Maybe even turn them into a paying customer.
I’m a one man team—I shouldn’t say that actually anymore. I’m a one man team currently with a handful of contractors. That just put me at a crossroads of I’ve got this codebase that I’ve been working on for a year. It’s a core and then there’s a front-end and a back-end (let’s call it that). The back-end is really unique, really hard to build, the kind of thing you hope you never have to do again. The front-end was like bootstrap and pretty basic components and tools. I tried to pick colors, but it wasn’t amazing. It was good enough.
I just hit this crossroads though. To your question, where have I gone wrong in terms of why can’t I keep these people around, and why can’t I fully satisfy their wish list? Maybe not 100% because I think that’s almost impossible. Why is it increasingly hard to build the next thing that somebody asks me for, and what does that mean for my business? Those were the questions I was facing in February and March.
Rob: It was pretty obvious to you just that people were not engaging and not paying. It’s never obvious what you do then. It’s never obvious what you build. How did you get to that point? I guess that end of the story is that you have a lot more traction now, growth has started kicking up, and people are getting value out of it. Here we are in August six months later. We know that you made a good decision. You changed the product enough that you do have traction now. How did you figure out what to build? Was it conversations with the customers or something else?
Matt: Yeah. I was thinking about this. We’re always looking, as founders, for validation. I know I am. I think most of us are. When people say things that are complementary, they just tend to really put wind in our sails (pick your metaphor). It feels great and you remember those things. There’s a bit of a bias towards the evidence that you’re on the right track. But then, as I said, there was this mounting evidence that I wasn’t on the right track like something was wrong.
I really said I’ve got to start piecing together the consistent story that I’m hearing from the users that I really want to have. Whether it’s people that are on the verge, but the app just isn’t good enough, or maybe they’re people who love the app and then fell out of love with it because it wasn’t good enough. A deep look or maybe a scary look at that evidence and that feedback and saying, what product do these people actually need?
A little bit of context is helpful, and this sounds a little counter-intuitive. I was able to raise another round of funding right around the same timeframe—February. It was based on the traction that I had with the first version of the product. Again, what investors were seeing, what I was seeing was there is clearly a demand for this. People are paying. You are getting users. They’re coming in. Something’s not quite right, but at least the kindling is there.
I think you and Einar, when you invested through TinySeed, were really betting on me as a person and a proof of concept. I think these people were saying, proof of concept has proven out, hasn’t quite figured out the customer yet—the monetization yet, but were willing to bet that Matt’s on to something. I think it’s important to say that that way in March frankly as the world was shutting down to say, wow, I’ve got 12 months plus of runway suddenly where I don’t have to worry about revenue. I’ve got a bunch of data from customers. Now is not the time to do incremental stuff. Or better said, now is an opportunity to do something big.
If I’m going to do something big now, making big changes now, and then seeing how that goes over the next 12 months is better than, oh, I’ll make incremental changes the next 9 months. Burn through a bunch of this new runway, and then find out that I needed to make big changes. I chose to flip it around and say, let me really go back to basics and build against the feedback that I’m getting from this user, this user, and these users because that’s the market I want. Those are the people I want to satisfy.
It’s just being deliberate about who I wanted to please and then being honest that it wasn’t good enough for them. The third factor—which I think is the most important in deciding to do the rewrite—was I’ve got the time. I potentially have the focus because suddenly the world shut down. If I can figure out how to work at home with four kids and a family all stuffed into this house together, then maybe I can basically chain myself to my desk for the next 60 days and do something big. Take a big risk.
Rob: It sounds like you were listening to customers. Would you say it was a job to be done? That in your head, the job of Summit is to do X. That you found that you had built it to do the wrong job? Does that metaphor work?
Matt: Yeah. Actually, I like it. I can use that as a start. I thought my hypothesis was that the job of Summit was to create a forecast for people. If you don’t have a forecast, you’re going to hit that button after putting in a few numbers and you’re going to get a forecast. In terms of a vending machine approach where you punch the Coke button and out comes a Coke. It worked.
The problem was, it would come out and people were like, oh, well, I really like Diet, I like Cherry, or I want mine with a splash of orange. I took a step back and I said, what are these people actually saying? Because you can go a little crazy as a founder when you get feedback of okay, I need to build a citrus flavor dispenser feature onto this. And then these people could be happy.
But what I found was that the things they wanted have nothing in common. What they had in common was they all wanted something else. If you think about that, the North Star became flexible. Like, oh, oh my. I have built a very inflexible vending machine. You come here, if you want A4, A5, you’re good. I can’t do anything else for you. These are your only two choices. The reason that I had to go so deep in terms of rewriting the product was I realized that I was competing against Microsoft Excel—and many of us are.
The difficult thing about competing against a spreadsheet—and probably other products like that—is that a spreadsheet is just endlessly flexible. There’s nothing you can’t do in a spreadsheet. They were coming to me with that same mentality of I’m not used to being constrained like this. I need to be able to copy this thing, add this thing, and do this thing. That need for flexibility, the job to be done was to provide them with a flexible canvas (if you will) or flexible blank space. That’s what I had to do for people.
Once I realized that. I was like, okay, the current version of Summit is not that. I started by ripping the front off the vending machine and saying, grab whatever you need. It’s all open season. And then I just kept going. It’s like a house remodeling project. Sometimes you don’t know when to stop. You just keep going and going and going.
I remember I got to the point where I had rewritten the front-end. I live-tweeted this. I worked in public to do this piece. I rewrote the front-end, but the back-end wasn’t different. I remember pausing and asking myself, okay, the front-end is a lot more flexible. You can click a lot more things and rearrange things. It’s a dashboard tool that’s a lot more modern. Is that all that they needed?
Kind of had this moment where you’re standing at that river and I just went for it. I said, no, actually, I think they need the back-end calculations to also be much more flexible. I basically open that up as well now. With the current version of Summit, not only is the front-end a more flexible, adjustable kind of workspace. The back-end also is just endlessly customizable. That was it. That was the breakthrough that I needed, not to say it wasn’t scary.
Rob: That was the thing. I’ll say there is a rule of thumb of perhaps it’s a yellow or red flag when a developer says we need to rewrite the whole codebase. It’s always, well, of course, we always want to rewrite the whole codebase because either someone else wrote it and it’s not as good as the code that I’m going to write. Or I wrote it a year or two ago. I was learning this stuff. It’s pretty crappy. I think I feel like that about most projects that I code. I want to rewrite them. It’s like, oh, there’s all these hacks and stuff.
Even going back to probably 15, 20 years, there was an essay by Joel Spolsky on the Joel on Software blog. It’s like never rewrite your codebase and this and that. It’s not never, but I always push back. I’m 35 Angel and TinySeed investments in, and I’ve had at least 4 or 5 of the startups that I advise or interact with, say, we need to rewrite our codebase. Every time I really push on it. How do you know? Why? Oh, you got a new CTO. Yeah, not a surprise. He wants to rewrite the codebase. Oh, he wants to change frameworks too, keep the same language? Yeah, of course he does because that’s his favorite framework. It’s this and that.
Sometimes it is the right decision, but it really needs to be thought through carefully. You and I may have had that conversation. I don’t even recall, to be honest. Did you put a ton of time into thinking of do I really want to do this? Because if I recall, it was about 60 days, 70 days of effort. Did you just say, you know what, I have the time. I’m just not going to think that much about it. I’m just going to crank through and do this.
Matt: Yeah. I’ve got good friends and mentors and definitely heard that feedback. I think you might have sent me an email saying, just in general, that’s not a good idea, but I trust you. There was definitely that voice on my shoulder. What was hard for me to communicate—because I’m a 1.75 person crew, let’s just say 1 man crew—at the time is we all wear many hats as founders. Especially in the early days, you wear all the hats.
The hat I was wearing when I said I wanted to do the rewrite, I’ve got a geek in me. Don’t get me wrong, but it wasn’t the inner geek saying, oh man, I want this to be faster, better, or a new framework. It wasn’t the shiny object syndrome developer in me. It really was the business strategist, the founder that said, I want a product that I can be proud of. That when I do a demo, I’m looking forward to those demos. I know people are going to be happy instead of knowing that they’re going to say, oh, well, I need these six things. I need to satisfy this need in the market that’s being expressed by these people.
It was really a lot more of—it sounds weird, but it was—the sales and marketing-driven decision to say I’m not doing this for performance’s sake to eke out another 10%. I’m not even doing this for the framework’s sake. I’m doing this so that when I do a demo with somebody, it blows them away, and they buy the thing. I’ve lived in that situation before—doing sales of things where there’s just all these shortcomings. You don’t always have to go back and rewrite things. Sometimes you just need to tell the customer, hey, sorry. It’s just not a good fit for you right now. It’s on the road map. We’ll let you know when we get to it.
But I made the executive decision—as you have the luxury of doing in the early days—to say, no, I’m the CEO and founder. There’s enough evidence here coming from my inner salesperson to say, this is not just the right product. We need to rewrite it. It was my inner CEO going, hey, developer Matt. Guess what you’re going to do. You’ve got a job to do. You better roll up your sleeves and learn Vue.js, Hasura, and a whole bunch of new tech because you’re going to want to do all these things.
Of course, I let myself have fun. Don’t get me wrong. It was a blast. I really felt like I was hiring my developer self to do a job. Not my developer was like, oh, I have an idea. We should do this. I think that just comes through experience. Not to say I’m perfect, but you got to be really honest with yourself about where your motivation is coming from to do something like that.
Rob: That’s a really good point for folks to think about. If you’re a single founder, a two-founder team and you are thinking about rewriting, put on your sales and marketing hat, put on your CEO hat, not your CTO or developer hat. Not that there’s never a reason. You can have a code that is so bad that you can’t add features and it takes you a month to do a day’s worth of work or whatever. Of course, that happens, but it’s a lot less frequent than developers tend to make it out to be. Knowing that it came from that sales and marketing perspective. It truly was almost needed to be a different product. Summit 2.0 is really, really different from Summit 1.0.
Matt: Yeah, completely. You can actually build Summit 1.0 using Summit 2.0. If that doesn’t bend people’s minds. Summit 1.0 was just one template now in the new world. One other thing is that the CTO did speak up a little bit in that time. The one thing I told Peter this on the podcast was, I want to build this in a way where if it is successful, I can hire developers to help me get it on the next level and the next level. Because the first version was one of those things where I got to build this thing by hook or crook. It doesn’t matter what the code looks like. Just get the date on the screen, try to sell some subscriptions, and test the interest.
With this one, I said, I have a pretty good feeling this is going to be well-received. Let me take a little bit longer, maybe two, three, four, five weeks longer. Which is, again, doubling the timeframe but I’ve got the time. Let me make sure that what I come out with is something where I can at least turn to a skilled dev and say, hey, the market likes this. Can you take over these parts now? Because this is the foundation. This is not a throwaway, basically. That was maybe a concise way to say. My inner CTO was like, don’t have it be thrown away. If we’re going to do this, at least do it in a way where we don’t have to scrap it again because we don’t want to do this again.
I did follow that. I think that’s worked out pretty well, fortunately. I’ve had other developers contribute since then. It’s moving faster now because of that.
Rob: That’s really nice. How long did the rewrite take you?
Matt: I think 70 days of coding. Essentially with the commit and push every day.
Rob: Oh wow. That’s a great way to do it.
Matt: Yeah. It was very consistent. Actually, that was fun. You can look at my GitHub or I can at least look at my GitHub repost. You can see where my consistent deployments or pushes died off and I became very sporadic in terms of my product progress with the first version. Because I was hitting these walls to do the next feature. It just required a bigger effort, a bigger effort, and a bigger effort.
I was like, okay, time to brew the coffee and crank out this feature. It’s going to be super hard to do, and I would get these bursts of productivity. With the new one, it’s actually nice to see a quantitative self. You can see, hey, look at that. Every day, something new—a little bit better, a little bit better. That also helped me know that I was on the right track. It wasn’t halfway across, but still, nothing delivered that kind of project.
Rob: I’m looking at your revenue graph. As I mentioned earlier, you’re a TinySeed batch one company, so I have access to that kind of stuff. There is a really noticeable uptick in your MRR. Of course, I’m trying to scroll through it now. It looks like from June to July, your revenue ticked up. You’re still early stage (so folks know). But there was a doubling or something of MRR, and then it went up another whatever. Is that because of V2? Is this rewrite instantly resonated with people that noticeably?
Matt: Yeah. I think the short answer is yes, but I’ll qualify that by saying, I took it then to the customers that I was essentially targeting with this rewrite. I took it to them basically as soon as it was ready and I said, aha. Here is the flexibility you’ve been asking for. Here is the tool. I know it’s not done yet, it’s not 100%, so I want your list. But if you agree this is on the right track, I would love your support. I would love you to buy into it because I think this is what you’ve been looking for. I was successful in those sales, which felt great. Obviously, that was a huge validation.
It wasn’t really the numbers, so much as saying, wow, out of these three or four companies or founders that are in my sweet spot—the ones I really want to please—they bought. That was huge. Who knows? With the old version, I’m sure I would’ve sold some subscriptions as well. But again, back to the personas, it would have been to these people. It would have been to those other people. That was not what I ultimately wanted to do.
Rob: Right. Now, I logged into a brand-new Summit account. The first thing that pops up, it says, welcome to Summit, the software to replace your financial spreadsheet. And then you have three different pre-built models. You have self-service SaaS, early-stage SaaS, sales-driven SaaS, and then you have upload your own model.
I’m guessing that in Summit V1, one of these models was the default and you were limited with assumptions in there versus this is a meta-level where it’s a much more of an Excel. I can build whatever I want.
Matt: Yeah. It really is. It’s more like maybe a Lego bucket at this point where you can build a model, build your house. Here are all the pieces. Here’re the building blocks. The first version was more like, here’s a Lego kit. It only builds this kind of house. I hope that you live in a ranch home, and you can adjust a few things about it. How big is your garage, and how big is this. You can make some changes, but it wasn’t the kind of thing like, here’s a bucket of parts. That bucket of parts approach is where what the screen you’re looking at right now is essentially saying, here are five kits. You can pick one or three kits and you can pick one.
That’s nice too because you gave me some really good feedback. That wasn’t always there. That wasn’t actually there at the very beginning of the relaunch. What you said, and I think it ran through is, oh man, a blank slate is just really tough. This is interesting to go through. I pushed back on that at first. I remembered getting your email and thinking, I don’t know if he gets it yet. There’s all this flexibility now. I don’t want to preload stuff. That takes it away.
A lot of people face this blank slate problem with the SaaS app is what do I fill it with? I was worried that if I automatically put in a bunch of building blocks, you would come to that same conclusion of like, oh, look at that. This isn’t for me because this is assuming that I’ve got a sales team, or this is assuming that I’m self-service or whatever.
It’s really silly. But I just remembered back to Microsoft Excel, for example, or Microsoft Word, and what happens when you load up those applications? You get hit with this screen and it says, are you trying to do an invoice? Are you trying to do a short story or an essay? It has all these templates.
I just had this mental breakthrough of like, oh yeah, duh. I can just show them a list of options and they can pick one. That then gives me the best of both worlds. If you want a blank slate, man, you can have it. But if you’re an early-stage founder, and you see early-stage SaaS in there, you can just click it. Then, hopefully, that gets you started faster.
Rob: The beauty of that is not even that you have to use it as is, but when you click it, it prepopulates a bunch of stuff and I then I can go tweak it. That’s what we learned when we’re building Drip was you have this workflow builder. Which is this visual designer and you can do if then else statements. It’s […] complete language in this visual builder for email. People were the experts, the power users, the Bren and Duns loved it.
Everyone below that level—even mid-level marketers—were like, I don’t know what to do first. What should I do? It wasn’t until we got the blueprints built and you could just one-click import a blueprint that we really started getting the mid-level and lower end marketers. I think that’s probably where my feedback came from is having built a similar engine that Derrick and I knew the workflow builder is incredibly powerful. So cool when we launched it. Quickly, all those questions of oh, what should I do? It was like, I guess we got to show you some guidance.
Matt: Yeah, absolutely. That’s my job now. This is kind of a retrospective. There is a group of users of the first product that I essentially alienated. They came to the new one and basically said, what have you done? You took away the one I liked, and you replaced it with this power tool. I don’t know what to do. It was pretty painful to hear. It’s nothing more satisfying as a product person and to hear that somebody loved the thing you made. But I wasn’t going to keep that around.
What I’m trying to do now is through Looms, education, those templates, and blueprints, I’m just building up a community. I really do want to work backward now and say, you can still use this. There’s going to be some learning. This is now more like a Drip or that kind of power tool. You have to decide that you want to be good at this and learn a new skill to an extent, but it’s still better than Excel. You’re going to like it more than Excel, but there is a learning curve. That’s fine. That appeals to me. Frankly, I really enjoy the subject so much that I enjoy teaching people how to use it.
Rob: That makes a lot of sense. We talked last time about the value of forecasting in SaaS in terms of when to use cases, fundraising, to see when your money’s going to run out. But if you’re a bootstrapper—which you most likely are listening to this—show hiring is a big one. Ad budgets, like, hey, ads are starting to work. Can I throw $5,000, $10,000 a month at it? Or will I run out of cash just because of my LTV pans out? If it takes me six months to get paid back, I need X amount of cash.
Yeah, you could model that in Excel, but this is going to take everything into account. There’s ad spend, there’s any of those big decisions around spending money in a way that is complicated and can put you in a cash crunch.
Matt: Yeah. What’s nice about a model approach instead of a spreadsheet is you set a founder in front of a spreadsheet and you say, put your business in here. There’s an immediate thought of okay, I need a revenue row, I guess, and I also need an expenses row. And then I need this, I need that. They start to fill out that classic spreadsheet template view of the month over a month like what you see in QuickBooks.
What’s interesting about this, and I’m still flushing this out, but I’m really just asking you to tell me about your business. Tell me what your revenue plans are, what your acquisitions channels are, and what your team looks like. Founders are really good at that. You can just ask a founder like, how do you acquire your customers? Oh, we have Google Ads spent. Cool, let me capture that real quick, done.
The hope is that it’s really a more natural way to capture business is this model. Where to sketch your home on a piece of paper on a napkin is easier than necessarily going through and saying what are all the dimensions and all these different things. Which people can seize up. That’s the test right now is to see how many folks can come to this and essentially describe their businesses and get out something that is really useful in making decisions.
Rob: As we move towards wrapping up, we got to talk about this homepage because it is one of the most compact, sparse. I think there is a total of 15, 16 words on it, not including your copyright at the bottom. It’s your logo. It’s a picture of a hummingbird, which is pretty cool. Then it’s, tell your forecasting spreadsheet you’re never getting back together. Design your business with Summit instead. There’s a button to create a free account. There’s a button to sign in.
I have seen creative SaaS homepages. Obviously, the standard one with pricing on it, or maybe that’s another link. There’s a top nav, which you don’t have. You have no footer. I once did a long-form sales page. The Drip homepage was a long-form sales page for quite some time, but I’m not sure that I have seen one like this. I’m curious if you have inspiration, or if you just did it on a whim. The real question is, is it working, or do you know yet?
Matt: Yeah. That was definitely done because I needed a homepage. I was launching a new thing. It was a complete rewriting, including the marketing site. I just needed to get something out there that had those buttons. To be perfectly honest, what’s the minimum? It’s probably an h1, h2, login, and sign up buttons. That’s what it is. I have not prioritized adding to that for a couple of reasons.
One is, I’m still figuring out what Summit is. Not to be totally metaphysical, but what is this thing? I have a little bit of a concern that if I flush that out with a lot of words, first of all, that’s changing. I’m still figuring it out. Second of all, I got to update and maintain that stuff. There’s a bit of a liability that goes along with adding more words to that homepage.
The second part of it, which I will defend for different reasons. Maybe I’m just defending past actions because I have convenient data. But it’s working well enough. Through that homepage, it depends on the day, but I’m getting anywhere from—on a very, very slow day, maybe it’s a Sunday holiday or something like that—2-3 sign-ups. On a busy day, 10, 12, 15, 20 sign-ups through that page. That tells me something. It tells me that those are high intent people. They just wanted to get in and check it out.
I think, for now, honestly, I don’t feel ready to convince more people—people that are on the fence where they’re like, I don’t know if I need to tell my forecasting spreadsheet goodbye. I’m pretty happy with it, I don’t have a forecasting spreadsheet, or I don’t have any context. Those people, I’ll lure them in, I’ll bring them in, and tractor beam them in eventually. But for now, I like knowing that the people that get into the product are there because they’re motivated, what they did see resonated with them, or they heard about it some other way. That’s good enough for now because the feedback I get from those 5, 6, or 10 sign-ups per day is a good signal.
For what it’s worth, I actually think that’s about to end. I’m not hearing a lot of new things these days from these sign-ups. I think it’s really natural to go back to that homepage and say, jeez, Matt. You could probably widen your funnel here if you just helped a few more people realize that oh, that’s what this does. I see this as an opportunity. I haven’t prioritized widening the top of the funnel yet. But I will. I definitely will.
I’m actually investing a pretty good amount of time in business development and partnerships for Q3 and Q4 to give a lot more people to that homepage. I fully intend to give them a little bit more insight into what it is.
Rob: No. That makes sense. I think there is a certain benefit to simplicity, especially in the short term. That’s cool to hear that’s your thought process and that is what you’re experiencing. I certainly can attest to I had a tool. I ran a SaaS up before Drip called HitTail, and it’s a long tail SEO keyword tool that plugged into your Google webmaster tool or something. And it pulled out the search console—they kept changing the name of it. But it would pull out keywords that you should rank high for based on your content and based on how people are finding you. But you weren’t ranking high enough. You were on the second page of Google. It would suggest them as things to beef up to get to the first page.
The way that I sold it, and I found that it really resonated, was a curiosity headline of how the tool works. It’s analyzed over a billion keywords in its lifetime across thousands and thousands of websites. It will suggest the keywords that you should be ranking for but aren’t. It didn’t go into how it did it. Once you got in the tool, you can figure out what it was doing. But it was really a curiosity play of this is the job it does, these are the testimonials, and these people are saying it works.
When you first arrived at the site, people would have skepticism. Does this thing actually work? Is it worth the money? Is it going to waste my time and all that? But that curiosity play was enough to get a lot of sign-ups—really high trials to paid conversion rate. I can imagine with you this headline, like you said, if someone came here totally cold, and they don’t really know what this is, or they don’t have the context in, I’m not sure it’s enough to draw them in. As you said, if you’re into forecasting and you really don’t like the spreadsheet, the headline captures it, and that’s enough. That is an interesting approach in this early stage.
Matt: Yeah. I felt a little bit more justified when Hiten Shah, who’s a TinySeed mentor, came and shared with the group. He’s now running usefyi.com or FYI. That was my inspiration for this. If he can get away with it, and it’s literally just an h1 and then a button. I don’t know how that’s going for him, what his plans are, I’m not speaking to that. But I saw it and said, okay, here’s a guy who knows a thing or two about heatmaps, homepages, and actions.
The one thing that resonated with me or I took away from that was what’s the thing you want them to do when they’re here? With his, it’s sign in with Google. With mine, it’s I want you to create an account. It was just a great point of man, if you know the next action you want them to take, maybe it’s okay to just start by focusing on that.
Rob: All right. Before you launch an app, if you put up a landing page and drive traffic to where, or whatever, it’s very simple that landing page. Typically, it’s a headline, a short description, and an email caption format. That’s the standard format of it. You can get those to convert really high—10%, 20%, 30% of visitors. If they’re targeted, you have a good headline, and good curiosity created out of that, you can land a lot of folks.
I think there is something to that simplicity. My guess is with Hiten’s, he’s not doing something if it’s not working. I’m guessing that’s a pretty, pretty decent approach. Sir, thank you so much for coming back on Startups For The Rest Of Us. As I said at the top of the show, you are @mattwensing on Twitter and usesummit.com if folks want to check out what you’ve been up to and potentially forecast their SaaS with V2.
Matt: Awesome. Thanks for having me on, Rob.
Rob: Absolutely, man. Thanks. Thanks again to Matt for coming back on the show. If you enjoyed this episode, I really appreciate it if you would check the Startups pod Twitter feed, and you can @ reply because Matt and I both have been mentioned in the tweet that came out this morning or retweet, or whatever. Just let us know any piece of that conversation that you enjoyed or get value out of, and you feel like you’ll take with you as you go ahead in the coming weeks. Thank you so much for listening, and I’ll talk to you again next Tuesday morning.
Episode 515 | Finding a Co-Founder, Getting Better at Sales, and More Listener Questions
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Rob is joined by Anthony Eden from DNSimple as they answer your listener questions.
They cover topics ranging from tax liabilities with contractors, getting feedback on a prototype, and finding a technical cofounder.
If you have questions about starting or scaling a SaaS that you’d like for us to cover, please submit your question for the next episode. We’d love to hear from you!
The topics we cover
[01:26] Tax liabilities and managing international contractors
[10:45] Starting when stair stepping isn’t feasible
[16:38] Getting better at sales as a solo founder
[24:00] Finding a sales/marketing cofounder
[30:28] Getting feedback on a prototype, finding the right developer co-founder, and protecting your startup idea
[40:11] Considering a technical cofounder vs hiring a developer
Links from the show
- Episode 509 | Revisiting the Six Stages of SaaS Growth with DNSimple
- Intellectual Property Agreement
- W-8BEN
- Episode 498 | Selling During a Pandemic with Steli Efti
- The Startup Chat with Steli & Hiten
- Episode 507 | Making Cold Email Work in B2B SaaS
- Indie Hackers
- Activity Messenger
- Jobs to be Done
- DNSimple | Twitter
- DNSimple | Website
- Anthony Eden | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
Subscribe & Review: iTunes | Spotify | Stitcher
Rob: Welcome to this week’s episode of Startups For The Rest of Us. This is Episode 515, and I’m your host, Rob Walling. Every week on this show, we cover topics related to building and growing startups using an ambitious but insane approach. We’re not willing to sacrifice our health or our relationships to grow our companies.
This week we answer listener questions, and I have founder of DNSimple, Anthony Eden, back on the show. We tackle a bunch of questions about stair stepping, about becoming better at sales, and about looking for and finding co-founders. With that, let’s dive right in.
Anthony Eden, sir, thanks so much for coming back on the show.
Anthony: Thanks for having me on again, Rob. Appreciate it.
Rob: As a reminder to folks, you were on episode 509 just about six weeks ago and you are the founder of DNSimple, a bootstrapped business for a decade, 15 employees, multiple millions in revenue, and you are a domain name registrar, and domain management. Is that a relatively accurate picture?
Anthony: Yeah, that’s a pretty good picture, that sums it up.
Rob: Awesome. Today we are going to dive into listener questions as I’ve been letting folks know and our first question is a voicemail from, I’m mispronouncing his name. I think it’s Ges, but it’s like hair. It’s one of those sounds that we don’t make in Western English. So I’ll let him say his name and we’ll roll into that voicemail right now.
Ger: Hi, Rob, this is Ger from Routine Factory again. A while ago, I sent you a question about going international with our SaaS for people with special needs. A few months ago, one of our U.S. customers left us a message that uses Routine Factory for his brother in law and loves the experience. We’ve had some great conversations online and ended up hiring him part time.
A few months later, he’s already helped us by making our international website sound more natural and our social media page is no longer dead in the water. This step does feel right. I’m just wondering if there might be some tax or liability issues that I’m not aware of right now. There’s no paperwork, only an NDA. He sends us weekly payment requests through PayPal.
I’m fully aware that you’re not a lawyer, but your insights are much appreciated. Okay Rob, thank you very much for considering my question and hope to see you in the future.
Rob: Thanks for the question and congrats on moving forward with that. This was just a couple of months ago. Ger had emailed in about expanding into the U.S. from, I believe it might have been the Netherlands or Sweden. It was somewhere where he was trying to figure out if he should go adjacent or try to come to the U.S. So it’s awesome that they were able to move forward.
I will obviously counter it again with this is not legal advice or tax advice and neither Anthony or I are attorneys or CPAs, but Anthony, did you hear the question as they now have one customer in the United States and he’s wondering if there’s tax or liability issues with having this single customer in the U.S.? Is that the question that you hear him asking?
Anthony: It sounds a little bit like that, although what’s interesting is that he was saying he was giving feedback and the person was asking if he’s making a payment request. It wasn’t clear to me whether this person on the other end is actually doing, they said they hired them part time, so in fact, it is somebody who’s working on the product with them a little bit, providing feedback, maybe actually doing some work for them.
I don’t think it’s necessarily just the customer. I think they actually have some sort of a business relationship with this person already.
Rob: Okay, let’s assume that’s the case and that this advisor or contractor, I guess we’ll call him, is a contractor that lives and resides in the US as an international company. What type of stuff should they be thinking about?
Anthony: The biggest thing that you have to start looking at, of course, is you have to consider your local laws and how those are impacted by the foreign laws from wherever this person lives.
For example, one of the big ones that my attorney generally talks a lot about is intellectual property. If you have a developer or a contributor who’s outside of your country or even inside of your country and they’re actually writing code for you, the thing you really need to do is make sure that you get an IP assignment.
That’s before they even start working, you have an agreement written up which states that the work that they’re doing for you is owned by your company, because if you don’t do that, you put yourself at risk in the future of somebody coming back to you and saying well, I did this work for you and I wasn’t compensated fairly so now I feel like you should compensate me and oh, look, you’re very successful, therefore, you should really compensate me heavily.
Essentially, you want to protect yourself by having clear agreements in advance for things like intellectual property. Clear agreements for the mechanism for payment, the number of hours they’re going to be working if it’s a contractor. Again, these are the kinds of things that are a staple of setting up an agreement with a contractor or an employee inside of your country or outside. These are the basics you should do for everyone.
I always recommend hiring a good attorney who’s in your area first, understand what the impacts are in your country, and then if you’re also hiring somebody outside of the country there are attorneys that specialize in this type of thing. Granted, they’re not cheap, but the value in the long run is that you protect yourself from much more significant risks down the line.
Rob: Yeah, I really like the way you’ve called that out. I think that a lot of early stage founders overlook having an IP agreement with every employee, every contractor, anyone who they work with. It’s something that I overlooked in the early days, too, because it’s kind of a pain in the butt.
You want to bring someone on for, let’s say it’s 10 hours a month of work. It’s like, I got to draft this thing up and I got to send it to him on Docsketch or DocuSign or whatever and get him to sign it.
Then what’s interesting is it doesn’t seem worth it in the early days. But here’s what happens if you ever want to sell your company, if you ever want to raise investment, when they get into due diligence, they’re going to ask you and they’re going to make you sign something that says every person who has touched this code or every person who has contributed to this IP I have an agreement with, and then you’re going to have to go back. I actually had to do this twice.
I had to go back to people who hadn’t worked for me in years and say hey, can we basically retroactively sign this? Lucky for me, I had maintained healthy relationships with these people. I have heard it go sideways where someone leaves disgruntled or you fire them. You don’t have the agreement and when you go back to them, they basically shake you down and they say I’ll do it for a price, and you wind up paying. I have multiple founder friends who have had to pay an ex employee to get them to sign an IP agreement so I think that’s a big one and to your point, this is not just for international. This is for local, and this is for contractors, and this is for full time employees.
To any place you’ve worked these days. If you’ve had a full time job in the last decade, you’ve signed an IP agreement because this has become such a big issue.
Anthony: When it comes to things like taxes, that’s a whole nother ball of wax and that’s, for example, if you hire somebody outside the country, you’re essentially going to have to pay them in a full amount and they’re going to be the ones that are going to have to ensure that they report their taxes properly, regardless of how they’re structured. Whether it’s an independent contractor or if they have a small company that they operate under, no matter what, essentially, the foreign entity has to basically do their own taxes.
Again, this should be spelled out clearly in any agreement that you have that essentially you’re paying them and they’re responsible to comply with all their local tax regulations, all of their local laws and things like that.
Rob: Yeah, and the general advice that I hear and see is if at all possible, don’t have international employees. Hire them as contractors.
Now, there are laws around that. That’s the ideal thing, but there are laws. So you have to adhere to those laws. But in general, the startups and the remote companies that I see working, if someone lives in another country, they hire them as a contractor or they hire their company, as you were saying, as a contractor and there’s that agreement that spells that out pretty clearly.
I will say that in the U.S, if I’m a U.S. entity and I have a contractor working in Europe, or Asia, or just any country outside, there is this form that the IRS makes you, or encourages you, wants you to fill out called the W-8BEN. You’re basically reporting on your international contractors and you’re saying it’s this person, and this is their name, and this is where they live, and this is how much I paid them last year. I don’t remember if it’s this how much I paid them or I’m going to pay them or whatever. I don’t know if other countries do that. It seems like a typical kind of US IRS thing.
Anthony: Yeah, we’ve done that. We’ve had to do the same type of thing for each one of our contractors outside the US and I think it’s a very good idea to ensure that you have that documentation in place if you’re a US entity. And then in your local country, you have to figure out what the tax reporting requirements are for basically any entity outside of your country who you’re paying and who’s doing work for you.
Rob: Yeah, these are always hard questions. To be honest, most founders I talked to, either they’re doing it as best they can, some ignore it just altogether, and they just figure they’re small enough to fly under the radar.
Others do the best they can and then there’s others who are super, super Type A about it, and they hire all the lawyers and hire all the CPAs and they know that they’re dialed in. I do think it comes back to risk tolerance and how much you want to walk the line and how far you’re willing to push it, because I do think there’s a lot here.
It’s like with GDPR or one of these other big regulations. If you live in the US, how much do you invest in being exactly letter of the law with GDPR. In a perfect world, you would do everything, dot every i, cross every t. Most small bootstraps in the US are not actually doing that right. They’re kind of doing as much as they need to to feel like they can say hey, I’m compliant and really not much more than that.
Anthony: I can understand that and then you have to ask yourself at what point does not doing this present a greater risk and cost in the long run than doing so? Sure, when you’re a single person and you’re just starting and you maybe have a few customers, okay, maybe it doesn’t make sense, but then maybe you should consider okay, I’m not going to hire somebody who’s outside of my country because the risk is significant enough and I can find somebody in my country who can do a similar job.
But if you can’t, then take a look at the risk. Hire somebody who understands how this works. If they cost you a thousand dollars, if your goal is to make your product work or your business grow, ultimately you’re going to have to decide to invest in some of these legal matters at some point. It’s just a question for you to decide how long you will wait before you do so.
Rob: Thanks for the question, Ger. I hope that was helpful.
Next question is from David. He says, “Hey, Rob loved the podcast. Really appreciate the work you do. I believe I have a very interesting SaaS product that I’m really interested in pursuing. But this is the very first business I’d be building and I’m concerned that I’m biting off more than I can chew. I’m currently employed full time and have taught myself how to program. I don’t feel confident that I have the technical skills to build something of this size.
I have two kids and a mortgage, so I’m not looking to take really big risks financially. This is a project I’m interested in and wanted to put the time and effort into, but I’m not sure how best to tackle it. I would be willing to consider a partner. Any thoughts?”
The subject line is, “When stair stepping is not feasible?” Anthony, what are your thoughts on this?
Anthony: Well, I mean, the first thing that I get struck by is I haven’t heard anything yet that says tair stepping isn’t feasible. In fact, just because you want to jump to a SaaS which is kind of one of the harder businesses to develop, doesn’t mean that the option isn’t there to stairstep your way to it.
For example, you might have things around your SaaS that are informational that you could start with by creating a product around that. In other words, you don’t have to have the full SaaS. You might be able to create something simple that says here’s these ideas around this SaaS that I built, and for $15, I’ll explain to you how it works with the tools that you have today.
A lot of ways the SaaS is taking some concept that is kind of manual today or maybe lots of different manual or semi automated processes and putting it together into something that works very smoothly for individuals and businesses who don’t want to take all this time to put everything together themselves. But it doesn’t mean there aren’t opportunities to stairstep.
Just taking the subject apart, my feeling is look closely and see, are there other ways to get there, especially if you’re risk averse? I understand that when I was first starting DNSimple, I had triplets. At the time, I think that they were maybe six or maybe seven, something like that, and I had a one year old. I was right there with you and the approach that I took being a technical founder, I was able to work on a lot of it myself. But I still avoided jumping into complete risk by working with a company that had hired me to do other work, and then I carved off the things that were DNSimple in our contract which allowed me to work on both things at the same time.
That was nice because it reduced the risk somewhat, but at the same time gave me the opportunity to focus on developing DNSimple. There are ways to do it where you don’t have to jump into it, feet first into it, and stop the work that you’re doing with your business and take all this financial risk. There are ways to do that, but really without more information on what the product is, without understanding what your background is, how the two are connected, it’s really tough for me to say that you cannot stair step to it.
Rob: Yeah, I’ve felt the same way when I read that. I think creating information around it, I think starting a product service around it, I think building some kind of audience around it, whether it’s through a podcast or a blog or whatever you want to do it, there are ways to do work that doesn’t carry a bunch of risk and kind of test the market a bit.
I think the big question, there’s a couple in my mind. Number one how can you validate this idea without writing any code? Again, without knowing the idea, it’s hard, but is this having to build a landing page, send some traffic to that type of thing? Is this I need to send 100 cold emails a week and start having conversations with HR managers, or construction firm managers, or whatever space that’s in to find out if this is even worth doing?
How can you get in conversations with people who would be potential buyers in order to validate or invalidate your hypothesis? Because all you have right now is an idea and a hypothesis and writing code doesn’t actually solve that or it won’t solve, disprove, or prove your hypothesis for 6, 12, 18 months. How can you prove or disprove it in the next 90 days? Is there a way to build so you can validate it with conversations?
Of course, that doesn’t get you 100%, but maybe that gets you to right now you’re at 10% or 20% based on gut feel. Can conversations get you to 50% or 60% thinking wow, this is pretty good. Can you build an MVP? That is the next step with Excel spreadsheets or with human automation using VAs, or with no code movement, or with just a crappy code MVP or something that maybe gets you to 60%, 70%, 75% that you think it’s going to be worthwhile.
The bottom line is all of this kind of removes risk one piece at a time. It gives you a little bit of confidence and it makes it easier for you to find a co-founder the more validation you have. Because if you go to a developer today and say I have an idea. Want to work for equity? Developers hear that all the time, why would they do that? But if you come and say I have an idea, I have built a no code prototype that I have ten people paying $50 a month for, and I have a waiting list. I’m in conversation with another 50 people.
Now you have something. That’s the way I would think about it, how can you get further down this process of launching this thing into the wild and validating it without spending hundreds of hours to actually code the thing up?
Anthony: Agree with you 100%, Rob. The key of any business is the processes that you’re going to end up building around it, technology or not. Those are the parts that are really interesting and if you can wire that up with something where you’re basically doing things manually in the beginning just to verify, are there customers out there? Do they see the value? How do they translate that value into actual dollars? That’s priceless and you don’t need to start developing a huge entire product in order to do so.
Rob: Yeah, and I do think if it’s SaaS, stair stepping, Anthony and I have named info-products and productized consulting and building an audience is different ways to kind of start the end. There’s also, is there a way to build a WordPress plugin version of this or Shopify plug in version that maybe isn’t SaaS that is dipping that toe in the water and could get you a little bit of exposure, a little bit of revenue, a little bit of experience?
Because, again, when I think of having two kids and a mortgage and trying to build and launch a SaaS on the side when I’m not a developer who I think I can build it, there’s just a lot of hurdles in your way. So I’d encourage you to think creatively about that. I hope that’s helpful for you, David.
Our next question is from Andy and his subject line is, “Becoming better at sales.” He says, “Hey, Rob, I love the show. As an early stage SaaS founder, I’m looking to learn outside of my given skills of product design and programming. I’ve got a newer B2B SaaS product that I’m looking to expand to a wider audience. To do that, I realize becoming better at sales is crucial. So my question is what can a solo founder do to increase their knowledge in the sales aspect of a business? It seems that the tactics of today are extremely different than any just a handful of years ago. Are there courses, books, mentors you would recommend? Is it more of a learning by doing type of skill? I imagine it’s a combination of all those seeking help from someone else. But I’m curious about your take. I should note that I’m also introverted and the art of sales sounds quite scary to me, but I know it’s necessary. So I’m ready to put up or shut up. Thanks for the advice, Andy.” Anthony, what do you think?
Anthony: Andy, I feel your pain. I’m not an introvert, but even I’m sort of afraid of the idea of trying to cold sell somebody, somebody I don’t know that has no knowledge of my product and trying to get out there and sell my product to them. It’s hard. It’s very hard, and frankly, I’m not sure, at least for me, it didn’t work. I’ve tried it before and the idea of pitching somebody who has no idea what I do or what the product does just never was really very useful for me.
On the other hand, building an audience, which is something you said, you want to bring to a wider audience, that’s less about getting out there and necessarily selling, cold selling. It’s more about how do you speak to that audience? How do you write for that audience? Where does that audience, where do they get together on the internet or in real life? And how can you become part of that community and give them the things that they need to get them into sort of into your lead pipe line so that then they get to learn about your product because there’s a genuine need there.
I think a lot of the key to sales is focusing on aligning somebody else’s needs. They need something now with the fact that you have a product that fulfills that need. The first thing I would suggest is there are books out there, there’s lots of courses you can read about sales, but I would say the real thing is to talk to people. You don’t have to go pitch them. You can just talk to them and say, hey, I built this thing and I know you’re in my space. I wonder if you’re interested in doing things like, just have conversations with them and that’s a good starting point from my point of view.
Then the other thing, like I said, is figure out how you can get into communities where multiple people that might be interested in your product congregate and ultimately, it is hard. It’s very hard. It takes a lot to sort of put yourself out there and sell your product, but if you really believe that what you have is going to help them, it’s a lot easier to sell them at that point.
Rob: Yeah, I think that’s a good point. I like to think of selling as the way like my co-founder with TinySeed, says if you’re selling B2B SaaS, especially to more higher priced customers, which if you’re having one-on-one conversations that you should be charging enough to make that worth your while, think of yourself as a high priced consultant who isn’t charging any money, but you’re actually giving people advice that is worth hundreds of dollars an hour because you are the expert in your space.
If you’re talking to a customer, you tend to know more about your competitors and about your own product than anyone else in the conversation as a rule. That mindset, because I’m also introverted. I don’t love selling like it’s just not my strong suit. But that shifted a lot for me and that these conversations are more about finding the right solution rather than forcing something on people.
Obviously there’s cold email where you could cold email someone and then you’re not that warm essentially when they come onto a call and you’re trying to convince them of things. That’s not really what I’m thinking about here. I am thinking more about like inbound lead gen and these are just sales conversations from people who are genuinely trying to educate themselves on your product, on the space and trying to find the best fit.
I remember having conversations with folks as we were growing Drip where I would literally recommend a different tool because they would tell me their use case would start digging in and I would get to the point where you know what? MailChimp is actually a better fit for you. It’s less expensive and you don’t need any automations. Drip is like a Ferrari, but you can totally go with the Nissan or a Toyota. MailChimp is a solid tool and it’s going to do what you want for less money.
That was where I remember feeling a little bit weird about that like, should I be doing that? Am I a bad salesperson? But it was like, no, as the high priced consultant, the high paid consultant who isn’t charging anything, that was the right recommendation.
I think that’s my mental model of it. I think if I were to look at mentors, I would look at two people coming off the top of my head. The first, of course, is Steli Efti. He’s a many time MicroConf speaker. He’s a TinySeed mentor. He’s been on this podcast for at least three times. If you just go to startupsfortherestofus.com and search for his name, and I think we’ll link a few of those up in the show notes and you can hear back.
He’s written a dozen books or ebooks on selling and it’s all focused on B2B SaaS. So that’s someone who I would start with. He also has a podcast called The Startup Chat, where he talks with Hiten Shah a couple of times a week about stuff.
Very good person to be mentored by and again mentored, you don’t ever even need to meet him in person because he has so much content out there, much like some folks who listen to this podcast and email me and be like you’re my favorite mentor. It’s like we’ve never met and I don’t know who you are, but you just talk on the mic enough and people have read the books and stuff. Steli Efti is one.
Then Damian Thompson who was on the show Episode 507, talking about cold email. He is a different style than Steli, but he’s been in B2B software sales for 20, 25 years, and he’s a coach now, a trainer in I think it’s vpsales.co. Again, his approach is a little different with Steli which is why I like it. You get kind of a variety of viewpoints, but he’s another guy that I would be following today. You have other thoughts on this, Anthony?
Anthony: Just the last thing was I want to double down on what you said about a lot of I think how you and I probably think about sales is more dealing with inbounds where people are already interested in what we’re doing and building up that inbound pipeline. The investment that you need to make is really writing good material that gets out there that you can publish and that potentially people will find on search engines or that other people from your customer base will link to in their blog posts or wherever they’re publishing, maybe doing videos and things.
Essentially, you need to think about giving them a hook that gets them inbound, because if they’re coming in, they’re already interested and it makes your job more about figuring out like Rob was saying are we the right tool for you?
And like Rob, I have told people from time to time, I really wish we were the company to help you, but we’re not. Go to this other company, and we have a very small number of companies in the domain space that I would recommend outside of our own company. But I’ve done it before and sometimes that’s the right thing to do because it’s not always a great fit.
I think at Basecamp, they talked about this as well about having sort of a sweet spot for their customers and sometimes customers are either too small or too big to hit that sweet spot, and they’re okay with that. Again, when you accept that, you know your space, that you know where you fit, that you know who your audience is, that you know what your product does, and you know when the fit is good, it makes the selling part a lot easier.
Rob: Thanks for the question, Andy. I hope our thoughts were helpful. Next couple questions are about finding a co-founder and it’s funny how these came in waves. But the first one is from Martin and he says, “Looking for a business co-founder.”
He says, “I discovered your podcast only recently. Indie startups really resonate with me. I’m a misfit and I don’t like playing by the rules set by authority. I’m driven by solving customer problems with code. I’m a technical founder building activitymessenger.com which is an SMS/email marketing platform for Sports and Leisure. Competing against Mailchimp’s constant contact in a niche with two advantages.
The first is I send SMS because millennials don’t read their email. Second is integrated to the registration system because that’s where all the contact information is. Six months in, I have around 10 customers giving me feedback to help me shape the product. It’s pretty sticky and seems to be generating anywhere from $50-$100 MRR per customer.” So he has a $25 monthly fee and then there’s variable bundles of SMS that you purchase. “I’m looking for a business co-founder, someone to take on sales and marketing. Where should I look?” What do you think sir?
Anthony: This one is interesting. I’ve tried to find people who I thought would be a good fit for the sales and marketing of my business and I tried to do this early on. It’s hard to take somebody, especially when you’re really passionate about your product and put them in that position, unless they, too, are very passionate about that product.
The first thing that if I was really going to try to go look for a co-founder, I would look for somebody who is interested in this space, but maybe who doesn’t have the technical depth that you have in it, but really is very interested and can see a future where this will be successful.
Now, since you’re in the center and the sports and leisure space, it may be somebody else who is involved with Sports and Leisure, but maybe who doesn’t have that deep technical knowledge that you do. But they really know sports and leisure. They know how to know that audience. They know how to market to the audience. They know the words that the audience understands, they know how to communicate with them, where they live and where they congregate and so that might be one way to do it.
My guess is there’s probably public bulletin boards for this type of community out there, maybe I’d start by looking through that. I’m going to also offer one other thought for you, which is I don’t know if you necessarily need somebody to be the business side of it. I think that if you’re early on in this, you probably have enough knowledge already of your product and of the space to be able to do a little bit of work to get out there and to make yourself known in those communities. It’s going to take some legwork and it’s going to probably make you uncomfortable, but the value of doing so in the long run, there’s a strong upside. You won’t be losing any value here, at least at the small scale.
Then if you continue to get traction, then you can start thinking okay, now I understand even more about my sales process because I’ve gone through it and now I know do I need somebody to do marketing first? In other words, getting those inbound leads because your product is going to be self-service or do I need somebody to get sales because my customer out there, the sales cycle requires a longer sales cycle. It requires more hands on work with potential customers, but ultimately results in a larger contract size. Well, then you can look for that type of person.
Rob: Yeah, I think that’s really good advice, that’s what I was going to say first off, is maybe check your assumptions on whether you need a co-founder right now and I would question that because the further along you get, the more traction you have, the better off you are to, as you said, figure out exactly what you do need.
The more traction you have, potentially the less of your company you have to to give up. Oftentimes, people will complain about investors investing and taking a portion of their equity. But really the most equity you’ll ever give up is to a co-founder or your other co-founders so I’m not saying not to do it because of that, but I do think that you should definitely ask yourself what exactly do I need from someone and what would that look like?
To answer the actual question, I’m looking for a kind of sales marketing cofounder. A, yes is going to be hard to find someone good who’s not already working on their own thing, but the way that I used to recommend it is to go to in-person events. Of course, that’s not that’s not working right now with COVId. But that will work again in the future so that would be MicroConf or your Indie Hackers meetup or whatever.
I think in your case, I’m curious if there are any of your customers that on the off chance, any of the 10 people already paying you, any of them potentially have time to work on something on the side with you or does their business would it be complementary to them and so strategically they might want to to team up? It’s a long shot, but I would certainly think about that.
Another thing I would look at is MicroConf Connect where we have like around 1500 founders and aspiring founders talking about this type of stuff. Some people I’ve seen post in there looking for co-founders on either side, the technical or the non technical side.
So microconfconnect.com, if you get in there, you can obviously ask around and start to feel out who’s there in the community.
I think participating in Indie Hackers, indiehackers.com, the amazing community run by Courtland Allen. You start to see patterns and figure out who’s doing what in these communities.
Finally, if you’re listening to this and you feel like you could potentially be the sales and marketing co-founder that Martin might be looking for, for data points, he’s in Montreal, Canada, and its activitymessenger.com. If you want to take a look at it, you’re just going to drop me a line at questions@startupsfortherestofus.com and I will forward along any interested parties to Martin.
Not a co-founder matchmaking service, but it would be kind of fun to have a success story. I actually think we’ve had a few of these work out where it’s either a co-founder or it’s like hey, I’m looking for a contractor to do this, and people email it and get them hooked up. So that’s cool.
Anthony: I’ll tell you what, finding the co-founders is, you said it before. I think I’ve heard it on your podcast numerous times which is like marriage, and it really is. It requires some dating in advance that requires getting to know the person, and it’s a very challenging thing. I have no doubt that anybody who’s trying to find especially like a 50/50 co-founder, that’s hard work. That’s hard work to find somebody you don’t know and to build up that level of trust that you can actually be willing to take on such a serious endeavor with them.
Rob: Yeah. I agree. Don’t jump into this lightly, make sure that there’s vesting in place and all of that stuff. I hope that was helpful. Our next question is also about finding a co-founder. This one is about finding a technical co-founder. Actually the subject line is finding the right CTO, Chief Technical Officer and validation.
I’m going to read it as he’s written it, but I would discourage you from thinking, I’m looking for a CTO and more think, hey, I’m looking for a developer, co-founder. There’s some nuance to that with the language but from Nicolas and he says, “Hey, Rob, I’m a huge fan of yours and really appreciate everything you’ve done to help out the startup community. I just graduated from college amid this pandemic, and I’ve been working on a mobile app startup idea with a friend.
We’ve talked to many potential customers to validate the idea, but we haven’t shown them the prototype yet. Do you think we should show each one of them our prototype and change it based on their feedback? How do we determine what we should change and what we shouldn’t?” There’s a whole lot of questions buried in here. I didn’t realize that. Do you have thoughts on that, Anthony?
Anthony: Yeah. Actually, I do have a lot of thoughts. It sounds like the two friends, when they say prototype, I’m assuming that it’s a mockup. They have this mockup that they put together or maybe a prototype with like a no-code tool, but really, there’s a huge difference between those two things.
A prototype is something that actually works to some extent, and that somebody could use it. Whereas a mockup is going to be a non-working just the images of what things are going to look like when that product is built. Given that, let’s just assume for a second when they say prototype, it’s actually something where you can click on things and it goes through and it’s usable.
Yeah, you should absolutely be showing this prototype and getting feedback on it, but at the same time, I don’t know how much you know about jobs to be done over there Rob, but the jobs to be done concept, I really love it. The truth is that every product is helping people do a job or multiple jobs.
You as the two friends who are working on this mobile app, you have to really say what is the job that needs to be done? Ultimately, if you can do that job with that app, and people go, Oh, yeah, I need that. I do this job and that will make my job easier. Even if that job is socializing with friends, taking photos, and whatever it is, there’s still a job to be done.
What I highly recommend is don’t get too wrapped up in showing that prototype, and then somebody says, oh, you should move this button here or this flow is a little wonky or whatever because it’s not really as productive as saying does this solve your problem? Does this help you accomplish the job that you want to be done? If that’s the question that you’re asking if you’re getting good feedback from that perspective, then by all means show it to people.
Rob: Jobs to be done, big fan. We’ve talked about it on the show before, and I make you dead on with that. Whenever I build an app, I always have a vision, and it’s the vision of what the app should do. It’s a job to be done on the app. Sometimes that vision has to wander a little bit like with Drip, where it was just an email capture widget, and then it did some autoresponders, and then suddenly, it’s an ESP, and then it’s marketing automation.
That vision had to change over time, and I think as founders, we have to do that, but I do think that in the early days, it’s really hard. It’s very fragile, that vision of yours. You have to, yes. I would be showing it to people, and if you show it to 10 people, you have to aggregate or average their feedback or figure out which of it is really in line with your ideal customer, or your ideal end-user.
There were times when I had conversations in the early days with very consumer-oriented folks, and they wanted me to launch a mobile app. They were like if you don’t have an iOS and an Android app, then I can’t use Drip and it was like, okay, so we weren’t going to go do that. It wasn’t just because it was a lot of work to do, but it was because they weren’t in our ideal customer wheelhouse.
I think that is one of the hard things as a first-time founder, trying to build something novel from scratch is a real challenge, because you just don’t know when to trust your gut, and when not to. Wish you the best of luck with that. The actual question about the co-founder, Nicholas says, “We’re also having trouble finding the right CTO.” Which again, I would just call the developer, co-founder, or technical co-founder to join us and build it out.
One concern I have is trusting a person without ever meeting them in person, which hey, I do all the time. We fund companies without ever meeting the founders in person and we hire employees and stuff without ever meeting in person. That’s something you’ll just have to get used to over time, but, “How should we approach finding the right CTO? How can we ensure that that person won’t simply build it and disappear with our idea? Thanks so much for everything.” What do you think?
Anthony: Yeah. There’s a lot to pull apart here. Like he said, I definitely think that they should be using the term first developer or whatever you want to say. The reason is CTOs do a very specific job, they run technical organizations, and the skills required to do that are very different than somebody that’s building out the first version of an app.
You want the person that’s going to be like I’m going to put together this first version of this app, I’m going to do it quickly, it’s going to be awesome, it’s just going to work, it’s going to be tested, and you guys are going to be so thrilled about it that you won’t think twice about giving me half of your company because we’re going to make so much together.
Finding that type of person comes down to looking for somebody that is interested in—in the case of developers—building something that aligns with your space. In the case of mobile, you probably want to find somebody who is really interested in building mobile apps, and maybe who has built a couple of them of their own and you maybe want to try to figure out a way you have an idea that you think is valuable.
You have a prototype that you’re working on to get there, coming to them with that, and showing them how that you’re going to be able to exchange this tool for money. That’s the incentive that you want to use to bring on a developer and then you’re going to have to pay them. You need to be ready in some way to say, okay, whether that payment is going to be with the actual exchange of cash, payment through that means if it’s going to be through equity, or whatever it might be.
You need to mentally put in your head what you are willing to pay this person. There are tons of developers out there that will work on contract. Consider also that maybe what you really need is you need to hire an independent, who can take your little prototype to a first real minimum viable product for you.
Again, if you do this like we talked about earlier, make sure you get an intellectual property assignment in place. Make sure that you are clear that you’re paying them for the work that they’re exchanged for and don’t necessarily go in and get that co-founder yet. It may be a little too early. Again, without knowing more, it’s hard for me to tell whether you’re at that stage yet, but there are plenty of options to build it out without necessarily doing it.
If you haven’t tried them yet, there are no code tools out there that you can try. That’s like all the rage now, and all that stands for is essentially, a way that you can put together an app or a website without having to actually write all the code behind it, and it may be good enough to get you to your first version.
Rob: I like it. It’s a big question. If you obviously read at a college, you probably don’t have a budget to pay somebody but that’s the ideal way to do it. It’s contract to hire is how I think about it, and maybe it’s a contract to hire a co-founder or founding engineer or contract to hire a founding engineer.
Where that’s the ideal path to take, because then you can take this really long term view of it, but if not, I mean, the people I know who found technical co-founders after they already have some type of validation or they have prototypes and stuff. They do take a long time, they take months and months to vet the person and they do try to meet them in person at least once, but if you can’t in this time of COVID spend a lot of time on Zoom talking.
They do happy hours in the evening, they get to know the person on a human basis because this isn’t just a work relationship really is, as we say, often it is as much like a marriage as most marriages are. It’s a very intertwined relationship, and once you own a company with someone, there’s a lot of complexity there.
In addition, I would definitely have a vesting of shares such that if you say, all right, come on as co-founder or founding engineer, you get 10%, 20% of this company. They don’t instantly get that so that they can walk away with ownership that is going to vest over several years. Of course, you sign IP agreements, and you sign all the things that the entity owns it.
That’s how you keep someone. You vet someone to try to ensure that they are an ethical human being but then also you sign paperwork that says that if they do take the code and go off, that legally wouldn’t be a good idea for them.
Anthony: Can I just add one more thing to the last question, how do we ensure that person will simply build it and disappear with our idea? If it’s that easy, so if there’s no moat, there’s nothing that you have that’s special about this. Then chances are somebody already has probably built that idea, and somebody probably is out there hustling to do this.
I caution you to think that you have something that is so unique and special, that it hasn’t already been done or isn’t being worked on. Because if you do, then there may be other paths that you want to take as well, and then I would definitely ensure that you have an attorney, that you get all the legal agreements in place, as Rob has said, and make sure that the company, the entity owns that.
That’s the key. If you really have something that is unique and special that has a business behind. Like you’re going to create a business for it then go ahead and take the steps to make that business and assign the IP to that business, including the IP of the things that you work on. That way, you have this entity that is all contained within and it becomes a lot easier to hire and whether that hire is contracting or bringing on a partner and doing equity. You have an entity around which you can do this, but I only suggest that you do that if you really vetted the idea, you have customers lined up, or already have customers that you’re to the point of where you have revenue coming in off of this thing.
Rob: Thanks for the question, Nicolas. I hope that was helpful. One more question for today also on finding a technical co-founder. This is from Alistair, and he says, “A few years ago, I put my own money and my parents’ money into getting my health and safety app developed. I’m not a developer, so to keep costs down, I designed the app myself and I got a developer to make it.
Since then, I’ve mothballed the app, but this year COVID-19 has put my job on thin ice, and it gave me a kick in the backside to get back on it. So I got feedback from some actual customers this time instead of just going out on his own, and he said, with a few tweaks and additions to the concept, I’ve secured 30 customers that want to transfer from the app they currently use to mine.
I vastly improved my UX designing skills and I’m more confident than ever in the idea. The developer built exactly what I told them the first time around, but I’m still not a developer. My question is where do I go from here? Am I being foolish without a technical co-founder with me on this? Making the same mistake twice would really hurt, but I have customers waiting at this time.
I don’t really know where to start with finding a co-founder and the time spent finding one might risk losing these customers. Thanks. I’m a huge fan and dream of the day when I’m in a position to apply for tiny seed funding. Much love, much appreciation for what you do, and thanks, again for your advice.”
I was summarizing his email, but in essence, he had a developer who did some work on it earlier, and it didn’t work out, and he basically feels like he wasted the money early on, so he doesn’t want to make that mistake twice. This feels similar to the prior two questions where someone has done some validation. I think his question is a little different. He’s saying, should I find a technical co-founder?
Anthony: Yeah. He definitely hasn’t jumped to the conclusion that he must find a co-founder, which I like, actually. Especially, since he’s already had enough business acumen and skills to get this developed and he has a product that he can bring customers into. He even said he’s already secured 30 customers that want to transfer from the app they currently use to mine.
Awesome, do that. If you have customers and your app is going to work for them, then help them do the transfer and get them starting to pay for it, and then you can start seeing, okay, now can I grow this? Are there more customers out there? The downside of course to doing this, the risk that you’re taking, is that you validated with these 30 customers, but that’s where it stops.
Now I have a feeling 30 people who are interested in something is a lot more than a lot of companies start with before going out to actually grow, so that’s pretty awesome. I really think that you ought to try to run with this a little bit, and if you had a developer or company that helped build the revised version of this app, and it’s working, then stick with them.
Get those 30 customers in and maybe try to add on 30 more, 60 more, 100 more, or whatever, and then use the money from that to fund further development with this company for a little while longer. It doesn’t seem like you need necessarily a technical co-founder yet, because you seem to have a pretty solid base of knowledge, and you’ve already made some mistakes on your own, so you start already understanding what mistakes not to make again, with regards to developing the product.
You’ll find new ones, don’t worry, but at least you have a starting point, and I think you have enough to go on for me at least. That’s my thought. What do you think, Rob?
Rob: Yeah. I don’t know that I have anything to add to that. Whether they’re the co-founder, and again, I shirk away a little bit from that title in this case, it’s like should they just be a founding engineer, or that you can give someone equity without them being a co-founder. That’s where you have to think about: is this app complicated and is going to need 24/7 support, and it has a lot of moving parts?
It’s going to be hard to scale, there’s going to be performance stuff, and there are a lot of things moving around. I think of like an analytics app or like Drip, which sucked in a bunch of analytics. It’s just a very complicated tool. I think not having a technical co-founder would have been a real challenge there. If it is just a CRUD app, where it’s just create, read, update, delete, and stuff going in and out of some database tables.
I’m not so sure that you necessarily need a co-founder, but having a developer who is reliable who maybe is getting paid a reduced rate and has 10% equity in the company that’s vesting or maybe they’re paid solely in equity, in which case, maybe they get a little more than that. I think you have options here, and again, based on what Anthony said, 30 people willing to switch is a lot.
That shows me that there’s some traction here, and there is an appetite for this. In true early-stage, bootstrap founder status, like I would beg, steal, borrow, scratch, and claw to get those people using your app, and then you take that revenue and you build on it. Use it to find the developer or pay the developer to get the next feature built.
Thanks for the question, Alistair. I hope that was helpful. Wrapping up our mostly co-founder episode, that was fun. If folks want to keep up with you, you are @aeden on Twitter and your anthonyeden.com, as well as obviously, dnsimple.com if folks want to see what you’re up to.
Anthony: Yeah, absolutely. They can reach out to me. I’m happy to answer any other questions if somebody has more. It’s true. This really was the I need a co-founder episode. Hopefully, we were able to help a little bit. I feel like for a lot of folks that if you have something that’s working and you have the confidence to go with it and keep it going, just because the media out there in the startup world says, oh, you need to have a technical founder with a non-technical founder. You don’t have to believe that. If you have enough knowledge to hire the right people to help you out as a contractor, you can get a lot done.
Rob: Indeed. Sir, with the DNSimple, you had mentioned that you guys are about to launch an API of some kind, is that right? You and I were chatting on MicroConf remote last week. Do you want to give people a 30-second rundown of what’s coming up?
Anthony: Okay. The idea is that we want people to be able to build integrations between the services they use in DNSimple and vice versa so that for example, connecting a domain to another service is literally a one-click thing. I don’t want to say too much about it, because it’s been a long time coming, and I have no idea when it’s going to come out, but we’re working really hard to make that one of the key things that we put out there within the next probably 6-12 months.
Honestly, what I want from this more than anything else is making it so that people connect a domain without having to think at all about DNS. That’s the vision that I keep pushing forward, and hopefully, this API will make the development of tools that allow that even easier.
Rob: You already have an API. You were an API first company. I’m looking at dnsimple.com/api, and you can use your API to manage domains and do all types of DNS stuff, but you’re taking it a step further.
Anthony: That’s they can do everything like all of this can essentially be done right now with the API that we have. What is missing from this is the experience where you actually get feedback from all this connectivity, not just when you first set it up, but all along with the life of having that thing connected, and to me, that’s the piece that’s missing.
It’s something I’ve been pushing the team to try to get us moving in that direction. The bottom line is we need to have feedback in the DNSimple application for these connections that we established with these different services, not just when they’re first connected, but throughout the life of it. I’ve been working with the team, and we’re pushing really hard to try to get that implemented, but we have the full API. You can do all kinds of stuff with it today. This just like you were saying takes it another step.
Rob: All right, sir. Well, thanks again for joining me.
Anthony: Thanks so much, Rob. Have a good one.
Rob: Thanks again to Anthony for weighing in and bringing his expertise to the show. I hope you got a lot of value out of that. If you enjoyed this show, feel free to reach out to me @robwalling on Twitter, and he is @aeden. If you have a question for the show for a future Q&A episode, I actually believe we’re running pretty low on questions at this point. Just email them the questions at startupsfortherestofus.com and of course voicemails always go to the top of the stack. Thanks for listening. I’ll see you next time.
This week we answer listener questions, and I have founder of DNSimple, Anthony Eden, back on the show. We tackle a bunch of questions about stair stepping, about becoming better at sales, and about looking for and finding co-founders. With that, let’s dive right in.
Anthony Eden, sir, thanks so much for coming back on the show.
Anthony: Thanks for having me on again, Rob. Appreciate it.
Rob: As a reminder to folks, you were on episode 509 just about six weeks ago and you are the founder of DNSimple, a bootstrapped business for a decade, 15 employees, multiple millions in revenue, and you are a domain name registrar, and domain management. Is that a relatively accurate picture?
Anthony: Yeah, that’s a pretty good picture, that sums it up.
Rob: Awesome. Today we are going to dive into listener questions as I’ve been letting folks know and our first question is a voicemail from, I’m mispronouncing his name. I think it’s Ges, but it’s like hair. It’s one of those sounds that we don’t make in Western English. So I’ll let him say his name and we’ll roll into that voicemail right now.
Ger: Hi, Rob, this is Ger from Routine Factory again. A while ago, I sent you a question about going international with our SaaS for people with special needs. A few months ago, one of our U.S. customers left us a message that uses Routine Factory for his brother in law and loves the experience. We’ve had some great conversations online and ended up hiring him part time.
A few months later, he’s already helped us by making our international website sound more natural and our social media page is no longer dead in the water. This step does feel right. I’m just wondering if there might be some tax or liability issues that I’m not aware of right now. There’s no paperwork, only an NDA. He sends us weekly payment requests through PayPal.
I’m fully aware that you’re not a lawyer, but your insights are much appreciated. Okay Rob, thank you very much for considering my question and hope to see you in the future.
Rob: Thanks for the question and congrats on moving forward with that. This was just a couple of months ago. Ger had emailed in about expanding into the U.S. from, I believe it might have been the Netherlands or Sweden. It was somewhere where he was trying to figure out if he should go adjacent or try to come to the U.S. So it’s awesome that they were able to move forward.
I will obviously counter it again with this is not legal advice or tax advice and neither Anthony or I are attorneys or CPAs, but Anthony, did you hear the question as they now have one customer in the United States and he’s wondering if there’s tax or liability issues with having this single customer in the U.S.? Is that the question that you hear him asking?
Anthony: It sounds a little bit like that, although what’s interesting is that he was saying he was giving feedback and the person was asking if he’s making a payment request. It wasn’t clear to me whether this person on the other end is actually doing, they said they hired them part time, so in fact, it is somebody who’s working on the product with them a little bit, providing feedback, maybe actually doing some work for them.
I don’t think it’s necessarily just the customer. I think they actually have some sort of a business relationship with this person already.
Rob: Okay, let’s assume that’s the case and that this advisor or contractor, I guess we’ll call him, is a contractor that lives and resides in the US as an international company. What type of stuff should they be thinking about?
Anthony: The biggest thing that you have to start looking at, of course, is you have to consider your local laws and how those are impacted by the foreign laws from wherever this person lives.
For example, one of the big ones that my attorney generally talks a lot about is intellectual property. If you have a developer or a contributor who’s outside of your country or even inside of your country and they’re actually writing code for you, the thing you really need to do is make sure that you get an IP assignment.
That’s before they even start working, you have an agreement written up which states that the work that they’re doing for you is owned by your company, because if you don’t do that, you put yourself at risk in the future of somebody coming back to you and saying well, I did this work for you and I wasn’t compensated fairly so now I feel like you should compensate me and oh, look, you’re very successful, therefore, you should really compensate me heavily.
Essentially, you want to protect yourself by having clear agreements in advance for things like intellectual property. Clear agreements for the mechanism for payment, the number of hours they’re going to be working if it’s a contractor. Again, these are the kinds of things that are a staple of setting up an agreement with a contractor or an employee inside of your country or outside. These are the basics you should do for everyone.
I always recommend hiring a good attorney who’s in your area first, understand what the impacts are in your country, and then if you’re also hiring somebody outside of the country there are attorneys that specialize in this type of thing. Granted, they’re not cheap, but the value in the long run is that you protect yourself from much more significant risks down the line.
Rob: Yeah, I really like the way you’ve called that out. I think that a lot of early stage founders overlook having an IP agreement with every employee, every contractor, anyone who they work with. It’s something that I overlooked in the early days, too, because it’s kind of a pain in the butt.
You want to bring someone on for, let’s say it’s 10 hours a month of work. It’s like, I got to draft this thing up and I got to send it to him on Docsketch or DocuSign or whatever and get him to sign it.
Then what’s interesting is it doesn’t seem worth it in the early days. But here’s what happens if you ever want to sell your company, if you ever want to raise investment, when they get into due diligence, they’re going to ask you and they’re going to make you sign something that says every person who has touched this code or every person who has contributed to this IP I have an agreement with, and then you’re going to have to go back. I actually had to do this twice.
I had to go back to people who hadn’t worked for me in years and say hey, can we basically retroactively sign this? Lucky for me, I had maintained healthy relationships with these people. I have heard it go sideways where someone leaves disgruntled or you fire them. You don’t have the agreement and when you go back to them, they basically shake you down and they say I’ll do it for a price, and you wind up paying. I have multiple founder friends who have had to pay an ex employee to get them to sign an IP agreement so I think that’s a big one and to your point, this is not just for international. This is for local, and this is for contractors, and this is for full time employees.
To any place you’ve worked these days. If you’ve had a full time job in the last decade, you’ve signed an IP agreement because this has become such a big issue.
Anthony: When it comes to things like taxes, that’s a whole nother ball of wax and that’s, for example, if you hire somebody outside the country, you’re essentially going to have to pay them in a full amount and they’re going to be the ones that are going to have to ensure that they report their taxes properly, regardless of how they’re structured. Whether it’s an independent contractor or if they have a small company that they operate under, no matter what, essentially, the foreign entity has to basically do their own taxes.
Again, this should be spelled out clearly in any agreement that you have that essentially you’re paying them and they’re responsible to comply with all their local tax regulations, all of their local laws and things like that.
Rob: Yeah, and the general advice that I hear and see is if at all possible, don’t have international employees. Hire them as contractors.
Now, there are laws around that. That’s the ideal thing, but there are laws. So you have to adhere to those laws. But in general, the startups and the remote companies that I see working, if someone lives in another country, they hire them as a contractor or they hire their company, as you were saying, as a contractor and there’s that agreement that spells that out pretty clearly.
I will say that in the U.S, if I’m a U.S. entity and I have a contractor working in Europe, or Asia, or just any country outside, there is this form that the IRS makes you, or encourages you, wants you to fill out called the W-8BEN. You’re basically reporting on your international contractors and you’re saying it’s this person, and this is their name, and this is where they live, and this is how much I paid them last year. I don’t remember if it’s this how much I paid them or I’m going to pay them or whatever. I don’t know if other countries do that. It seems like a typical kind of US IRS thing.
Anthony: Yeah, we’ve done that. We’ve had to do the same type of thing for each one of our contractors outside the US and I think it’s a very good idea to ensure that you have that documentation in place if you’re a US entity. And then in your local country, you have to figure out what the tax reporting requirements are for basically any entity outside of your country who you’re paying and who’s doing work for you.
Rob: Yeah, these are always hard questions. To be honest, most founders I talked to, either they’re doing it as best they can, some ignore it just altogether, and they just figure they’re small enough to fly under the radar.
Others do the best they can and then there’s others who are super, super Type A about it, and they hire all the lawyers and hire all the CPAs and they know that they’re dialed in. I do think it comes back to risk tolerance and how much you want to walk the line and how far you’re willing to push it, because I do think there’s a lot here.
It’s like with GDPR or one of these other big regulations. If you live in the US, how much do you invest in being exactly letter of the law with GDPR. In a perfect world, you would do everything, dot every i, cross every t. Most small bootstraps in the US are not actually doing that right. They’re kind of doing as much as they need to to feel like they can say hey, I’m compliant and really not much more than that.
Anthony: I can understand that and then you have to ask yourself at what point does not doing this present a greater risk and cost in the long run than doing so? Sure, when you’re a single person and you’re just starting and you maybe have a few customers, okay, maybe it doesn’t make sense, but then maybe you should consider okay, I’m not going to hire somebody who’s outside of my country because the risk is significant enough and I can find somebody in my country who can do a similar job.
But if you can’t, then take a look at the risk. Hire somebody who understands how this works. If they cost you a thousand dollars, if your goal is to make your product work or your business grow, ultimately you’re going to have to decide to invest in some of these legal matters at some point. It’s just a question for you to decide how long you will wait before you do so.
Rob: Thanks for the question, Ger. I hope that was helpful.
Next question is from David. He says, “Hey, Rob loved the podcast. Really appreciate the work you do. I believe I have a very interesting SaaS product that I’m really interested in pursuing. But this is the very first business I’d be building and I’m concerned that I’m biting off more than I can chew. I’m currently employed full time and have taught myself how to program. I don’t feel confident that I have the technical skills to build something of this size.
I have two kids and a mortgage, so I’m not looking to take really big risks financially. This is a project I’m interested in and wanted to put the time and effort into, but I’m not sure how best to tackle it. I would be willing to consider a partner. Any thoughts?”
The subject line is, “When stair stepping is not feasible?” Anthony, what are your thoughts on this?
Anthony: Well, I mean, the first thing that I get struck by is I haven’t heard anything yet that says tair stepping isn’t feasible. In fact, just because you want to jump to a SaaS which is kind of one of the harder businesses to develop, doesn’t mean that the option isn’t there to stairstep your way to it.
For example, you might have things around your SaaS that are informational that you could start with by creating a product around that. In other words, you don’t have to have the full SaaS. You might be able to create something simple that says here’s these ideas around this SaaS that I built, and for $15, I’ll explain to you how it works with the tools that you have today.
A lot of ways the SaaS is taking some concept that is kind of manual today or maybe lots of different manual or semi automated processes and putting it together into something that works very smoothly for individuals and businesses who don’t want to take all this time to put everything together themselves. But it doesn’t mean there aren’t opportunities to stairstep.
Just taking the subject apart, my feeling is look closely and see, are there other ways to get there, especially if you’re risk averse? I understand that when I was first starting DNSimple, I had triplets. At the time, I think that they were maybe six or maybe seven, something like that, and I had a one year old. I was right there with you and the approach that I took being a technical founder, I was able to work on a lot of it myself. But I still avoided jumping into complete risk by working with a company that had hired me to do other work, and then I carved off the things that were DNSimple in our contract which allowed me to work on both things at the same time.
That was nice because it reduced the risk somewhat, but at the same time gave me the opportunity to focus on developing DNSimple. There are ways to do it where you don’t have to jump into it, feet first into it, and stop the work that you’re doing with your business and take all this financial risk. There are ways to do that, but really without more information on what the product is, without understanding what your background is, how the two are connected, it’s really tough for me to say that you cannot stair step to it.
Rob: Yeah, I’ve felt the same way when I read that. I think creating information around it, I think starting a product service around it, I think building some kind of audience around it, whether it’s through a podcast or a blog or whatever you want to do it, there are ways to do work that doesn’t carry a bunch of risk and kind of test the market a bit.
I think the big question, there’s a couple in my mind. Number one how can you validate this idea without writing any code? Again, without knowing the idea, it’s hard, but is this having to build a landing page, send some traffic to that type of thing? Is this I need to send 100 cold emails a week and start having conversations with HR managers, or construction firm managers, or whatever space that’s in to find out if this is even worth doing?
How can you get in conversations with people who would be potential buyers in order to validate or invalidate your hypothesis? Because all you have right now is an idea and a hypothesis and writing code doesn’t actually solve that or it won’t solve, disprove, or prove your hypothesis for 6, 12, 18 months. How can you prove or disprove it in the next 90 days? Is there a way to build so you can validate it with conversations?
Of course, that doesn’t get you 100%, but maybe that gets you to right now you’re at 10% or 20% based on gut feel. Can conversations get you to 50% or 60% thinking wow, this is pretty good. Can you build an MVP? That is the next step with Excel spreadsheets or with human automation using VAs, or with no code movement, or with just a crappy code MVP or something that maybe gets you to 60%, 70%, 75% that you think it’s going to be worthwhile.
The bottom line is all of this kind of removes risk one piece at a time. It gives you a little bit of confidence and it makes it easier for you to find a co-founder the more validation you have. Because if you go to a developer today and say I have an idea. Want to work for equity? Developers hear that all the time, why would they do that? But if you come and say I have an idea, I have built a no code prototype that I have ten people paying $50 a month for, and I have a waiting list. I’m in conversation with another 50 people.
Now you have something. That’s the way I would think about it, how can you get further down this process of launching this thing into the wild and validating it without spending hundreds of hours to actually code the thing up?
Anthony: Agree with you 100%, Rob. The key of any business is the processes that you’re going to end up building around it, technology or not. Those are the parts that are really interesting and if you can wire that up with something where you’re basically doing things manually in the beginning just to verify, are there customers out there? Do they see the value? How do they translate that value into actual dollars? That’s priceless and you don’t need to start developing a huge entire product in order to do so.
Rob: Yeah, and I do think if it’s SaaS, stair stepping, Anthony and I have named info-products and productized consulting and building an audience is different ways to kind of start the end. There’s also, is there a way to build a WordPress plugin version of this or Shopify plug in version that maybe isn’t SaaS that is dipping that toe in the water and could get you a little bit of exposure, a little bit of revenue, a little bit of experience?
Because, again, when I think of having two kids and a mortgage and trying to build and launch a SaaS on the side when I’m not a developer who I think I can build it, there’s just a lot of hurdles in your way. So I’d encourage you to think creatively about that. I hope that’s helpful for you, David.
Our next question is from Andy and his subject line is, “Becoming better at sales.” He says, “Hey, Rob, I love the show. As an early stage SaaS founder, I’m looking to learn outside of my given skills of product design and programming. I’ve got a newer B2B SaaS product that I’m looking to expand to a wider audience. To do that, I realize becoming better at sales is crucial. So my question is what can a solo founder do to increase their knowledge in the sales aspect of a business? It seems that the tactics of today are extremely different than any just a handful of years ago. Are there courses, books, mentors you would recommend? Is it more of a learning by doing type of skill? I imagine it’s a combination of all those seeking help from someone else. But I’m curious about your take. I should note that I’m also introverted and the art of sales sounds quite scary to me, but I know it’s necessary. So I’m ready to put up or shut up. Thanks for the advice, Andy.” Anthony, what do you think?
Anthony: Andy, I feel your pain. I’m not an introvert, but even I’m sort of afraid of the idea of trying to cold sell somebody, somebody I don’t know that has no knowledge of my product and trying to get out there and sell my product to them. It’s hard. It’s very hard, and frankly, I’m not sure, at least for me, it didn’t work. I’ve tried it before and the idea of pitching somebody who has no idea what I do or what the product does just never was really very useful for me.
On the other hand, building an audience, which is something you said, you want to bring to a wider audience, that’s less about getting out there and necessarily selling, cold selling. It’s more about how do you speak to that audience? How do you write for that audience? Where does that audience, where do they get together on the internet or in real life? And how can you become part of that community and give them the things that they need to get them into sort of into your lead pipe line so that then they get to learn about your product because there’s a genuine need there.
I think a lot of the key to sales is focusing on aligning somebody else’s needs. They need something now with the fact that you have a product that fulfills that need. The first thing I would suggest is there are books out there, there’s lots of courses you can read about sales, but I would say the real thing is to talk to people. You don’t have to go pitch them. You can just talk to them and say, hey, I built this thing and I know you’re in my space. I wonder if you’re interested in doing things like, just have conversations with them and that’s a good starting point from my point of view.
Then the other thing, like I said, is figure out how you can get into communities where multiple people that might be interested in your product congregate and ultimately, it is hard. It’s very hard. It takes a lot to sort of put yourself out there and sell your product, but if you really believe that what you have is going to help them, it’s a lot easier to sell them at that point.
Rob: Yeah, I think that’s a good point. I like to think of selling as the way like my co-founder with TinySeed, says if you’re selling B2B SaaS, especially to more higher priced customers, which if you’re having one-on-one conversations that you should be charging enough to make that worth your while, think of yourself as a high priced consultant who isn’t charging any money, but you’re actually giving people advice that is worth hundreds of dollars an hour because you are the expert in your space.
If you’re talking to a customer, you tend to know more about your competitors and about your own product than anyone else in the conversation as a rule. That mindset, because I’m also introverted. I don’t love selling like it’s just not my strong suit. But that shifted a lot for me and that these conversations are more about finding the right solution rather than forcing something on people.
Obviously there’s cold email where you could cold email someone and then you’re not that warm essentially when they come onto a call and you’re trying to convince them of things. That’s not really what I’m thinking about here. I am thinking more about like inbound lead gen and these are just sales conversations from people who are genuinely trying to educate themselves on your product, on the space and trying to find the best fit.
I remember having conversations with folks as we were growing Drip where I would literally recommend a different tool because they would tell me their use case would start digging in and I would get to the point where you know what? MailChimp is actually a better fit for you. It’s less expensive and you don’t need any automations. Drip is like a Ferrari, but you can totally go with the Nissan or a Toyota. MailChimp is a solid tool and it’s going to do what you want for less money.
That was where I remember feeling a little bit weird about that like, should I be doing that? Am I a bad salesperson? But it was like, no, as the high priced consultant, the high paid consultant who isn’t charging anything, that was the right recommendation.
I think that’s my mental model of it. I think if I were to look at mentors, I would look at two people coming off the top of my head. The first, of course, is Steli Efti. He’s a many time MicroConf speaker. He’s a TinySeed mentor. He’s been on this podcast for at least three times. If you just go to startupsfortherestofus.com and search for his name, and I think we’ll link a few of those up in the show notes and you can hear back.
He’s written a dozen books or ebooks on selling and it’s all focused on B2B SaaS. So that’s someone who I would start with. He also has a podcast called The Startup Chat, where he talks with Hiten Shah a couple of times a week about stuff.
Very good person to be mentored by and again mentored, you don’t ever even need to meet him in person because he has so much content out there, much like some folks who listen to this podcast and email me and be like you’re my favorite mentor. It’s like we’ve never met and I don’t know who you are, but you just talk on the mic enough and people have read the books and stuff. Steli Efti is one.
Then Damian Thompson who was on the show Episode 507, talking about cold email. He is a different style than Steli, but he’s been in B2B software sales for 20, 25 years, and he’s a coach now, a trainer in I think it’s vpsales.co. Again, his approach is a little different with Steli which is why I like it. You get kind of a variety of viewpoints, but he’s another guy that I would be following today. You have other thoughts on this, Anthony?
Anthony: Just the last thing was I want to double down on what you said about a lot of I think how you and I probably think about sales is more dealing with inbounds where people are already interested in what we’re doing and building up that inbound pipeline. The investment that you need to make is really writing good material that gets out there that you can publish and that potentially people will find on search engines or that other people from your customer base will link to in their blog posts or wherever they’re publishing, maybe doing videos and things.
Essentially, you need to think about giving them a hook that gets them inbound, because if they’re coming in, they’re already interested and it makes your job more about figuring out like Rob was saying are we the right tool for you?
And like Rob, I have told people from time to time, I really wish we were the company to help you, but we’re not. Go to this other company, and we have a very small number of companies in the domain space that I would recommend outside of our own company. But I’ve done it before and sometimes that’s the right thing to do because it’s not always a great fit.
I think at Basecamp, they talked about this as well about having sort of a sweet spot for their customers and sometimes customers are either too small or too big to hit that sweet spot, and they’re okay with that. Again, when you accept that, you know your space, that you know where you fit, that you know who your audience is, that you know what your product does, and you know when the fit is good, it makes the selling part a lot easier.
Rob: Thanks for the question, Andy. I hope our thoughts were helpful. Next couple questions are about finding a co-founder and it’s funny how these came in waves. But the first one is from Martin and he says, “Looking for a business co-founder.”
He says, “I discovered your podcast only recently. Indie startups really resonate with me. I’m a misfit and I don’t like playing by the rules set by authority. I’m driven by solving customer problems with code. I’m a technical founder building activitymessenger.com which is an SMS/email marketing platform for Sports and Leisure. Competing against Mailchimp’s constant contact in a niche with two advantages.
The first is I send SMS because millennials don’t read their email. Second is integrated to the registration system because that’s where all the contact information is. Six months in, I have around 10 customers giving me feedback to help me shape the product. It’s pretty sticky and seems to be generating anywhere from $50-$100 MRR per customer.” So he has a $25 monthly fee and then there’s variable bundles of SMS that you purchase. “I’m looking for a business co-founder, someone to take on sales and marketing. Where should I look?” What do you think sir?
Anthony: This one is interesting. I’ve tried to find people who I thought would be a good fit for the sales and marketing of my business and I tried to do this early on. It’s hard to take somebody, especially when you’re really passionate about your product and put them in that position, unless they, too, are very passionate about that product.
The first thing that if I was really going to try to go look for a co-founder, I would look for somebody who is interested in this space, but maybe who doesn’t have the technical depth that you have in it, but really is very interested and can see a future where this will be successful.
Now, since you’re in the center and the sports and leisure space, it may be somebody else who is involved with Sports and Leisure, but maybe who doesn’t have that deep technical knowledge that you do. But they really know sports and leisure. They know how to know that audience. They know how to market to the audience. They know the words that the audience understands, they know how to communicate with them, where they live and where they congregate and so that might be one way to do it.
My guess is there’s probably public bulletin boards for this type of community out there, maybe I’d start by looking through that. I’m going to also offer one other thought for you, which is I don’t know if you necessarily need somebody to be the business side of it. I think that if you’re early on in this, you probably have enough knowledge already of your product and of the space to be able to do a little bit of work to get out there and to make yourself known in those communities. It’s going to take some legwork and it’s going to probably make you uncomfortable, but the value of doing so in the long run, there’s a strong upside. You won’t be losing any value here, at least at the small scale.
Then if you continue to get traction, then you can start thinking okay, now I understand even more about my sales process because I’ve gone through it and now I know do I need somebody to do marketing first? In other words, getting those inbound leads because your product is going to be self-service or do I need somebody to get sales because my customer out there, the sales cycle requires a longer sales cycle. It requires more hands on work with potential customers, but ultimately results in a larger contract size. Well, then you can look for that type of person.
Rob: Yeah, I think that’s really good advice, that’s what I was going to say first off, is maybe check your assumptions on whether you need a co-founder right now and I would question that because the further along you get, the more traction you have, the better off you are to, as you said, figure out exactly what you do need.
The more traction you have, potentially the less of your company you have to to give up. Oftentimes, people will complain about investors investing and taking a portion of their equity. But really the most equity you’ll ever give up is to a co-founder or your other co-founders so I’m not saying not to do it because of that, but I do think that you should definitely ask yourself what exactly do I need from someone and what would that look like?
To answer the actual question, I’m looking for a kind of sales marketing cofounder. A, yes is going to be hard to find someone good who’s not already working on their own thing, but the way that I used to recommend it is to go to in-person events. Of course, that’s not that’s not working right now with COVId. But that will work again in the future so that would be MicroConf or your Indie Hackers meetup or whatever.
I think in your case, I’m curious if there are any of your customers that on the off chance, any of the 10 people already paying you, any of them potentially have time to work on something on the side with you or does their business would it be complementary to them and so strategically they might want to to team up? It’s a long shot, but I would certainly think about that.
Another thing I would look at is MicroConf Connect where we have like around 1500 founders and aspiring founders talking about this type of stuff. Some people I’ve seen post in there looking for co-founders on either side, the technical or the non technical side.
So microconfconnect.com, if you get in there, you can obviously ask around and start to feel out who’s there in the community.
I think participating in Indie Hackers, indiehackers.com, the amazing community run by Courtland Allen. You start to see patterns and figure out who’s doing what in these communities.
Finally, if you’re listening to this and you feel like you could potentially be the sales and marketing co-founder that Martin might be looking for, for data points, he’s in Montreal, Canada, and its activitymessenger.com. If you want to take a look at it, you’re just going to drop me a line at questions@startupsfortherestofus.com and I will forward along any interested parties to Martin.
Not a co-founder matchmaking service, but it would be kind of fun to have a success story. I actually think we’ve had a few of these work out where it’s either a co-founder or it’s like hey, I’m looking for a contractor to do this, and people email it and get them hooked up. So that’s cool.
Anthony: I’ll tell you what, finding the co-founders is, you said it before. I think I’ve heard it on your podcast numerous times which is like marriage, and it really is. It requires some dating in advance that requires getting to know the person, and it’s a very challenging thing. I have no doubt that anybody who’s trying to find especially like a 50/50 co-founder, that’s hard work. That’s hard work to find somebody you don’t know and to build up that level of trust that you can actually be willing to take on such a serious endeavor with them.
Rob: Yeah. I agree. Don’t jump into this lightly, make sure that there’s vesting in place and all of that stuff. I hope that was helpful. Our next question is also about finding a co-founder. This one is about finding a technical co-founder. Actually the subject line is finding the right CTO, Chief Technical Officer and validation.
I’m going to read it as he’s written it, but I would discourage you from thinking, I’m looking for a CTO and more think, hey, I’m looking for a developer, co-founder. There’s some nuance to that with the language but from Nicolas and he says, “Hey, Rob, I’m a huge fan of yours and really appreciate everything you’ve done to help out the startup community. I just graduated from college amid this pandemic, and I’ve been working on a mobile app startup idea with a friend.
We’ve talked to many potential customers to validate the idea, but we haven’t shown them the prototype yet. Do you think we should show each one of them our prototype and change it based on their feedback? How do we determine what we should change and what we shouldn’t?” There’s a whole lot of questions buried in here. I didn’t realize that. Do you have thoughts on that, Anthony?
Anthony: Yeah. Actually, I do have a lot of thoughts. It sounds like the two friends, when they say prototype, I’m assuming that it’s a mockup. They have this mockup that they put together or maybe a prototype with like a no-code tool, but really, there’s a huge difference between those two things.
A prototype is something that actually works to some extent, and that somebody could use it. Whereas a mockup is going to be a non-working just the images of what things are going to look like when that product is built. Given that, let’s just assume for a second when they say prototype, it’s actually something where you can click on things and it goes through and it’s usable.
Yeah, you should absolutely be showing this prototype and getting feedback on it, but at the same time, I don’t know how much you know about jobs to be done over there Rob, but the jobs to be done concept, I really love it. The truth is that every product is helping people do a job or multiple jobs.
You as the two friends who are working on this mobile app, you have to really say what is the job that needs to be done? Ultimately, if you can do that job with that app, and people go, Oh, yeah, I need that. I do this job and that will make my job easier. Even if that job is socializing with friends, taking photos, and whatever it is, there’s still a job to be done.
What I highly recommend is don’t get too wrapped up in showing that prototype, and then somebody says, oh, you should move this button here or this flow is a little wonky or whatever because it’s not really as productive as saying does this solve your problem? Does this help you accomplish the job that you want to be done? If that’s the question that you’re asking if you’re getting good feedback from that perspective, then by all means show it to people.
Rob: Jobs to be done, big fan. We’ve talked about it on the show before, and I make you dead on with that. Whenever I build an app, I always have a vision, and it’s the vision of what the app should do. It’s a job to be done on the app. Sometimes that vision has to wander a little bit like with Drip, where it was just an email capture widget, and then it did some autoresponders, and then suddenly, it’s an ESP, and then it’s marketing automation.
That vision had to change over time, and I think as founders, we have to do that, but I do think that in the early days, it’s really hard. It’s very fragile, that vision of yours. You have to, yes. I would be showing it to people, and if you show it to 10 people, you have to aggregate or average their feedback or figure out which of it is really in line with your ideal customer, or your ideal end-user.
There were times when I had conversations in the early days with very consumer-oriented folks, and they wanted me to launch a mobile app. They were like if you don’t have an iOS and an Android app, then I can’t use Drip and it was like, okay, so we weren’t going to go do that. It wasn’t just because it was a lot of work to do, but it was because they weren’t in our ideal customer wheelhouse.
I think that is one of the hard things as a first-time founder, trying to build something novel from scratch is a real challenge, because you just don’t know when to trust your gut, and when not to. Wish you the best of luck with that. The actual question about the co-founder, Nicholas says, “We’re also having trouble finding the right CTO.” Which again, I would just call the developer, co-founder, or technical co-founder to join us and build it out.
One concern I have is trusting a person without ever meeting them in person, which hey, I do all the time. We fund companies without ever meeting the founders in person and we hire employees and stuff without ever meeting in person. That’s something you’ll just have to get used to over time, but, “How should we approach finding the right CTO? How can we ensure that that person won’t simply build it and disappear with our idea? Thanks so much for everything.” What do you think?
Anthony: Yeah. There’s a lot to pull apart here. Like he said, I definitely think that they should be using the term first developer or whatever you want to say. The reason is CTOs do a very specific job, they run technical organizations, and the skills required to do that are very different than somebody that’s building out the first version of an app.
You want the person that’s going to be like I’m going to put together this first version of this app, I’m going to do it quickly, it’s going to be awesome, it’s just going to work, it’s going to be tested, and you guys are going to be so thrilled about it that you won’t think twice about giving me half of your company because we’re going to make so much together.
Finding that type of person comes down to looking for somebody that is interested in—in the case of developers—building something that aligns with your space. In the case of mobile, you probably want to find somebody who is really interested in building mobile apps, and maybe who has built a couple of them of their own and you maybe want to try to figure out a way you have an idea that you think is valuable.
You have a prototype that you’re working on to get there, coming to them with that, and showing them how that you’re going to be able to exchange this tool for money. That’s the incentive that you want to use to bring on a developer and then you’re going to have to pay them. You need to be ready in some way to say, okay, whether that payment is going to be with the actual exchange of cash, payment through that means if it’s going to be through equity, or whatever it might be.
You need to mentally put in your head what you are willing to pay this person. There are tons of developers out there that will work on contract. Consider also that maybe what you really need is you need to hire an independent, who can take your little prototype to a first real minimum viable product for you.
Again, if you do this like we talked about earlier, make sure you get an intellectual property assignment in place. Make sure that you are clear that you’re paying them for the work that they’re exchanged for and don’t necessarily go in and get that co-founder yet. It may be a little too early. Again, without knowing more, it’s hard for me to tell whether you’re at that stage yet, but there are plenty of options to build it out without necessarily doing it.
If you haven’t tried them yet, there are no code tools out there that you can try. That’s like all the rage now, and all that stands for is essentially, a way that you can put together an app or a website without having to actually write all the code behind it, and it may be good enough to get you to your first version.
Rob: I like it. It’s a big question. If you obviously read at a college, you probably don’t have a budget to pay somebody but that’s the ideal way to do it. It’s contract to hire is how I think about it, and maybe it’s a contract to hire a co-founder or founding engineer or contract to hire a founding engineer.
Where that’s the ideal path to take, because then you can take this really long term view of it, but if not, I mean, the people I know who found technical co-founders after they already have some type of validation or they have prototypes and stuff. They do take a long time, they take months and months to vet the person and they do try to meet them in person at least once, but if you can’t in this time of COVID spend a lot of time on Zoom talking.
They do happy hours in the evening, they get to know the person on a human basis because this isn’t just a work relationship really is, as we say, often it is as much like a marriage as most marriages are. It’s a very intertwined relationship, and once you own a company with someone, there’s a lot of complexity there.
In addition, I would definitely have a vesting of shares such that if you say, all right, come on as co-founder or founding engineer, you get 10%, 20% of this company. They don’t instantly get that so that they can walk away with ownership that is going to vest over several years. Of course, you sign IP agreements, and you sign all the things that the entity owns it.
That’s how you keep someone. You vet someone to try to ensure that they are an ethical human being but then also you sign paperwork that says that if they do take the code and go off, that legally wouldn’t be a good idea for them.
Anthony: Can I just add one more thing to the last question, how do we ensure that person will simply build it and disappear with our idea? If it’s that easy, so if there’s no moat, there’s nothing that you have that’s special about this. Then chances are somebody already has probably built that idea, and somebody probably is out there hustling to do this.
I caution you to think that you have something that is so unique and special, that it hasn’t already been done or isn’t being worked on. Because if you do, then there may be other paths that you want to take as well, and then I would definitely ensure that you have an attorney, that you get all the legal agreements in place, as Rob has said, and make sure that the company, the entity owns that.
That’s the key. If you really have something that is unique and special that has a business behind. Like you’re going to create a business for it then go ahead and take the steps to make that business and assign the IP to that business, including the IP of the things that you work on. That way, you have this entity that is all contained within and it becomes a lot easier to hire and whether that hire is contracting or bringing on a partner and doing equity. You have an entity around which you can do this, but I only suggest that you do that if you really vetted the idea, you have customers lined up, or already have customers that you’re to the point of where you have revenue coming in off of this thing.
Rob: Thanks for the question, Nicolas. I hope that was helpful. One more question for today also on finding a technical co-founder. This is from Alistair, and he says, “A few years ago, I put my own money and my parents’ money into getting my health and safety app developed. I’m not a developer, so to keep costs down, I designed the app myself and I got a developer to make it.
Since then, I’ve mothballed the app, but this year COVID-19 has put my job on thin ice, and it gave me a kick in the backside to get back on it. So I got feedback from some actual customers this time instead of just going out on his own, and he said, with a few tweaks and additions to the concept, I’ve secured 30 customers that want to transfer from the app they currently use to mine.
I vastly improved my UX designing skills and I’m more confident than ever in the idea. The developer built exactly what I told them the first time around, but I’m still not a developer. My question is where do I go from here? Am I being foolish without a technical co-founder with me on this? Making the same mistake twice would really hurt, but I have customers waiting at this time.
I don’t really know where to start with finding a co-founder and the time spent finding one might risk losing these customers. Thanks. I’m a huge fan and dream of the day when I’m in a position to apply for tiny seed funding. Much love, much appreciation for what you do, and thanks, again for your advice.”
I was summarizing his email, but in essence, he had a developer who did some work on it earlier, and it didn’t work out, and he basically feels like he wasted the money early on, so he doesn’t want to make that mistake twice. This feels similar to the prior two questions where someone has done some validation. I think his question is a little different. He’s saying, should I find a technical co-founder?
Anthony: Yeah. He definitely hasn’t jumped to the conclusion that he must find a co-founder, which I like, actually. Especially, since he’s already had enough business acumen and skills to get this developed and he has a product that he can bring customers into. He even said he’s already secured 30 customers that want to transfer from the app they currently use to mine.
Awesome, do that. If you have customers and your app is going to work for them, then help them do the transfer and get them starting to pay for it, and then you can start seeing, okay, now can I grow this? Are there more customers out there? The downside of course to doing this, the risk that you’re taking, is that you validated with these 30 customers, but that’s where it stops.
Now I have a feeling 30 people who are interested in something is a lot more than a lot of companies start with before going out to actually grow, so that’s pretty awesome. I really think that you ought to try to run with this a little bit, and if you had a developer or company that helped build the revised version of this app, and it’s working, then stick with them.
Get those 30 customers in and maybe try to add on 30 more, 60 more, 100 more, or whatever, and then use the money from that to fund further development with this company for a little while longer. It doesn’t seem like you need necessarily a technical co-founder yet, because you seem to have a pretty solid base of knowledge, and you’ve already made some mistakes on your own, so you start already understanding what mistakes not to make again, with regards to developing the product.
You’ll find new ones, don’t worry, but at least you have a starting point, and I think you have enough to go on for me at least. That’s my thought. What do you think, Rob?
Rob: Yeah. I don’t know that I have anything to add to that. Whether they’re the co-founder, and again, I shirk away a little bit from that title in this case, it’s like should they just be a founding engineer, or that you can give someone equity without them being a co-founder. That’s where you have to think about: is this app complicated and is going to need 24/7 support, and it has a lot of moving parts?
It’s going to be hard to scale, there’s going to be performance stuff, and there are a lot of things moving around. I think of like an analytics app or like Drip, which sucked in a bunch of analytics. It’s just a very complicated tool. I think not having a technical co-founder would have been a real challenge there. If it is just a CRUD app, where it’s just create, read, update, delete, and stuff going in and out of some database tables.
I’m not so sure that you necessarily need a co-founder, but having a developer who is reliable who maybe is getting paid a reduced rate and has 10% equity in the company that’s vesting or maybe they’re paid solely in equity, in which case, maybe they get a little more than that. I think you have options here, and again, based on what Anthony said, 30 people willing to switch is a lot.
That shows me that there’s some traction here, and there is an appetite for this. In true early-stage, bootstrap founder status, like I would beg, steal, borrow, scratch, and claw to get those people using your app, and then you take that revenue and you build on it. Use it to find the developer or pay the developer to get the next feature built.
Thanks for the question, Alistair. I hope that was helpful. Wrapping up our mostly co-founder episode, that was fun. If folks want to keep up with you, you are @aeden on Twitter and your anthonyeden.com, as well as obviously, dnsimple.com if folks want to see what you’re up to.
Anthony: Yeah, absolutely. They can reach out to me. I’m happy to answer any other questions if somebody has more. It’s true. This really was the I need a co-founder episode. Hopefully, we were able to help a little bit. I feel like for a lot of folks that if you have something that’s working and you have the confidence to go with it and keep it going, just because the media out there in the startup world says, oh, you need to have a technical founder with a non-technical founder. You don’t have to believe that. If you have enough knowledge to hire the right people to help you out as a contractor, you can get a lot done.
Rob: Indeed. Sir, with the DNSimple, you had mentioned that you guys are about to launch an API of some kind, is that right? You and I were chatting on MicroConf remote last week. Do you want to give people a 30-second rundown of what’s coming up?
Anthony: Okay. The idea is that we want people to be able to build integrations between the services they use in DNSimple and vice versa so that for example, connecting a domain to another service is literally a one-click thing. I don’t want to say too much about it, because it’s been a long time coming, and I have no idea when it’s going to come out, but we’re working really hard to make that one of the key things that we put out there within the next probably 6-12 months.
Honestly, what I want from this more than anything else is making it so that people connect a domain without having to think at all about DNS. That’s the vision that I keep pushing forward, and hopefully, this API will make the development of tools that allow that even easier.
Rob: You already have an API. You were an API first company. I’m looking at dnsimple.com/api, and you can use your API to manage domains and do all types of DNS stuff, but you’re taking it a step further.
Anthony: That’s they can do everything like all of this can essentially be done right now with the API that we have. What is missing from this is the experience where you actually get feedback from all this connectivity, not just when you first set it up, but all along with the life of having that thing connected, and to me, that’s the piece that’s missing.
It’s something I’ve been pushing the team to try to get us moving in that direction. The bottom line is we need to have feedback in the DNSimple application for these connections that we established with these different services, not just when they’re first connected, but throughout the life of it. I’ve been working with the team, and we’re pushing really hard to try to get that implemented, but we have the full API. You can do all kinds of stuff with it today. This just like you were saying takes it another step.
Rob: All right, sir. Well, thanks again for joining me.
Anthony: Thanks so much, Rob. Have a good one.
Rob: Thanks again to Anthony for weighing in and bringing his expertise to the show. I hope you got a lot of value out of that. If you enjoyed this show, feel free to reach out to me @robwalling on Twitter, and he is @aeden. If you have a question for the show for a future Q&A episode, I actually believe we’re running pretty low on questions at this point. Just email them the questions at startupsfortherestofus.com and of course voicemails always go to the top of the stack. Thanks for listening. I’ll see you next time.
Episode 514 | An Inside Look at MicroConf Remote
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Producer Xander Castro has been working on MicroConf since 2014 and is a long-time listener of the show, but this is his first time on the podcast.
On this episode, we take an inside look at MicroConf Remote from a few weeks ago and discuss what worked well, what we’ll do differently next time and the difficulties of translating events from in-person to remote.
The topics we cover
[03:26] Turning to virtual events
[07:38] Stats & production technicalities for MicroConf Remote
[17:12] What worked well: pricing, timezones, and programming
[30:27] Things we learned from our first MicroConf Remote
Links from the show
- MicroConf Remote
- Xander Castro | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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Rob: Welcome to this week’s episode of Startups For the Rest of Us. I’m your host Rob Walling. In this week’s episode, we take an inside look at MicroConf Remote which was the event that we threw two weeks ago, and I bring producer Xander on to the show for the first time ever. He’s a longtime listener of the show, of course, and he’s been working on MicroConf since 2014, but he’s been working full-time on it for about the last year.
Xander has a background in event production. He’s been on the venue side. He’s been involved in events for like a decade. It’s a pretty extensive experience he’s had running events, and he does some pretty amazing things for us. If you’ve ever been to a MicroConf, we often get the question, how big is your staff for running this event?
He’s always like, oh, it’s just me and the founders, and people are like, whoa, because most events when we used to do starter and growth back to back and they’re 450 people there over the course of 4 ½, 5 days. You just have a whole event staff doing things and we really haven’t.
We really are that scrappy. Still continue to be that scrappy bootstrapped MicroConf ethos event and producer Xander is a big part of why we’re able to pull that off. We have a great conversation about MicroConf Remote. There’s a lot of inside baseballs, so if you don’t care about it, that’s fine, too.
We’ll be back next Tuesday morning at the normal time, but we talked about the event, why we wanted to do it, some of the challenges and things we considered. We talked about what worked really well and some things that we would do differently next time. With that, let’s dive into my conversation with producer Xander Castro. Xander Castro, thank you so much for joining me on the show.
Xander: Hey, thanks for having me the first time.
Rob: Indeed, so if you go to startupsfortherestofus.com and you search for the phrase Xander, I believe you’ve been mentioned. You just keep scrolling and scrolling, and there’s the next page. Producer Xander has been mentioned many times on the show, but you have yet to be in a conversation here.
For folks who don’t know, they would have heard a little from your intro button. You’ve been working with us on MicroConf since 2014 if I recall so quite a few events, and then you came on full-time just over a year ago, congratulations. Happy anniversary.
Xander: Well, thank you. It was a fun anniversary, wasn’t it?
Rob: Yeah. You’ve been working with us full-time on MicroConf on the big expansion in 2020. On your one year anniversary, we put on MicroConf Remote, which is what we came to talk about today. I did want to take a step back, though, and comment like 2020, we planned for seven in-person events. We were going from three up to seven, and then we were going to go from zero remote events or virtual events to two, and really, we haven’t done any in-person events.
Xander: No, no. 2020 has really dealt us the hand, everybody has been dealt, pretty much anybody that is producing live events right now is seeing a pretty rough year. There’s a lot going on right now and there’s much more that isn’t going on right now as a result of social distancing, quarantine, and whatnot with COVID-19.
Rob: Yeah. It feels like such an absolute dumpster fire in terms of trying to get people together. I don’t know about you, I want a do over.
Xander: Tell me about it. The live events industry is one that brings in like $6 billion a year annually just in the US. You just imagine all of those different staff members that are not working right now, and it’s just pretty devastating. It’s a rough industry to be in, that’s for sure at this point.
Rob: Yeah. A lot of folks have turned to virtual events, and that’s one thing that I wanted to say right off the bat is like we planned over a year ago to do two virtual events this year. At least two because we did the State of Independent SaaS Livestream back in January, and then we had decided we named it MicroConf Remote. Remember, we’re trying to figure out a name MicroConf, virtual MicroConf digital, MicroConf online, and we just loved Remote because of the idea of remote work.
We announced all of this last December but literally just about a year ago had said we’re going to do this thing. The fact that COVID happened really didn’t change those plans.
Xander: No. Not for MicroConf Remote, that’s for sure. I think we had always had this idea in mind about there was time to create a virtual implementation of what is MicroConf to really create a more accessible event that anybody around the planet would be able to access as they were interested and there weren’t those barriers to entry such as travel, setting aside over three-day plan to get out to a destination to attend a live event.
I think we always knew that creating something that was definitely more accessible to a mass audience was the route that we wanted to take with the remote version of MicroConf, for sure.
Rob: Yeah. We had been talking. You, Mike, and I believe talked about it four or five years ago about trying to do it.
Xander: Like in Barcelona.
Rob: Yeah. It’s been on our mind, but I know that it wasn’t like the highest priority because if you can do in-person events, I mean, personally, I think they’re just, I don’t know, better. I like in-person events because you have to travel. They’re more expensive, there are all these things, but there’s just a value there I think that is pretty much impossible to replicate online, so we had never prioritized it.
With this expansion, we did want to dip our toe in the water and get a little better at it, and so really, as I said, decided to do it last fall. I think we had talked for a while about not making it a replacement for MicroConf because an in-person MicroConf is so unique, and there’s so much about the setup in the hallway track and this and that, that we weren’t trying to replicate it.
We’re trying to do something a little different, and I think that’s a challenge and I think honestly if it hadn’t been for COVID, I think MicroConf Remote would have been even more unique than it was because there wouldn’t have been a bunch of other virtual events around it. We were in essence competing with these other Zoom events, but a lot of other online events, so we had to stand out that much more.
Xander: Definitely. As we were going through the research phase of what it would look like to implement MicroConf Remote back in November or December of 2019, we had done a bunch of customer interviews that focused around what it meant to attend MicroConf and what were the things that were drawing you to our live events. That person to person interaction was one of the high and above elements that people were seeking out when it came to attending MicroConf.
Even as we were in the midst of planning MicroConf Remote, we spent a little bit of time talking about how it wasn’t going to be a live version of MicroConf. I joked around saying that we should just brand it as not MicroConf because it was a unique way to look at what our attendees are constantly seeking, which is that person to person connection.
It’s an industry that few people that are innocent bystanders on the side looking inward don’t really understand the mechanics of starting your own business, doing the daily grind at home, not really being able to get out. A lot of people are starting to understand that more of these days.
I think that one of the things that we consistently try to achieve at our live events is the connection that’s formed in the hallway track. Trying to replicate that in the digital setting, as we’ll talk about a little bit later, is a challenge. It’s not the same type of experience you would see in a live experience when you’re shaking hands with someone which we should talk about. This is probably not going to be something that we’re going to encourage during live events, even when we’re able to get back together, but I think that trying to replicate that was something that took a lot of consideration and something that we were hoping we could emulate for sure.
Rob: We weren’t trying to replicate, we were trying to translate from in-person to online.
Xander: Yeah, absolutely.
Rob: Just to give an overview. We sold just about almost 700 tickets, and so quite a few listeners will probably have bought tickets and may have attended or seen the video. In essence, we decided to do a 5-hour livestream. Parts and parts of it were pre-recorded. We had some people pipe in with quick fixes that were two, three, five minutes.
Sherry and I did founders and cars, not getting coffee, a segment that had to be pre-recorded because we couldn’t do live streaming from a car. But most of it was truly live and whether it was, I interviewed a few people. We had for keynote talks, a lot of Q&A, and live interaction, which again, is one of the benefits of live streaming.
You went all out. You flew into Minneapolis and rented a studio where we had (if I recall) three cameras on me at all times, which was fun, but also like, geez, I can’t even scratch my nose without it having six angles of it.
Xander: You’re going to be caught at every angle.
Rob: Every angle, and then were there like seven people working on it, six- or seven-person crew?
Xander: Four behind the scenes and then we had three that were upfront helping with the filming, lighting, teleprompt, and things like that plus me.
Rob: That’s eight people in just the technical production of it. Of course, I’m up on stage, and then Tracy was doing a bunch of live customer support because when you have that many people attending, at our peak, I believe we had 570 attending the event. That’s just a lot of people doing stuff, so it was a real baller setup.
We kept saying, hey, this is going to be a different event. This is not just a host sitting in his bedroom in front of you. I’m in my bedroom office right now for example, but we didn’t just want that to be people in front of webcams. It gives that live feel to it because I was on different sets.
I was between two different sets, and I was on a talk show. We had like a talk show format, and we had a bunch of different creative elements to try. We knew the content would be startup focused. It’s similar to the content we would have in MicroConf or on this podcast, but with more live interactivity, but you really double down on the creativity of the visual elements to make the experience different for people.
Xander: Yeah. The goal was to really create something that would be considered bingeable. Something that carries you from segment one to segment two, or to keynote speaker, to the Q&A elements. We really wanted to keep things pretty tight in terms of the timeline of presenters, nobody had more than 20 minutes to deliver their own individual element or talk.
We wanted to create that sense of forward momentum, that idea that you’re going to sit down and you’re going to take in five hours of essentially TV. How can we make it so that each element leads into the next but is entertaining enough to really feel like it’s worth spending that much time? When it comes to digital events, even with the 700 some tickets that we sold, seeing that we had 575-ish folks that were on at peak, that’s a pretty significant number of people that are not engaging.
The idea is that you see anywhere from 50%-60% fall off when people purchase tickets to when they actually attend the event when it comes to digital experiences. We wanted to give everyone who chose to tune in a reason to stay versus just presenting the content the way that we had set it up and then distributed.
We wanted to make sure that there were these engaging touchpoints. I will say we recorded almost everything in advance of the event as well, just in case there were catastrophic failures across some of the technology, so we had those backup elements so that we could auto throw to it so nobody would miss anything.
There were some issues with that we’ll talk about in a bit, but there was a lot of thought that went into creating a through-line and the streamline story from the opening of the shows through to the closing Q&A with Jason Fried. I think that there was a lot of thought that went into how to create that line, but we wanted to make sure that it was being presented in a way that copies of people’s attention in-between each of the keynote sessions per se, and that kept it moving forward.
Rob: There’s a point. I think translating an in-person event to an online event, we didn’t just want to put on a MicroConf and have a camera there live streaming it, because we could have done that. We could have either flown speakers in or we could have sent a camera crew to every speakers’ place and just have them sit on a stage and we just don’t think that’s going to work the way that it should. It’s not the optimal translation. As I said earlier, we’re not replicating, we’re translating. We’re trying to adjust it.
Xander: Exactly. As you think about like transcription. These services that are talking about hey, can we get up to 95% accuracy? The translation between a live event and a digital event is not 1:1. There is going to be a fall off in terms of the experience the guests are having.
In theory, the keynotes and the content should be pretty much lined up with the expectations that they have going into the event. But when you go to a live event, you have that interconnectedness to the crowd. You have that sense of energy and that moment where a speaker says one individual thing and everyone’s ears perk up, or there’s a laugh that comes across the crowd. That’s an intangible experience that you really cannot create in a remote or digital setting.
There are some challenges in putting forward content that in a live event, it would originally be meant to be experienced and mass. When you’re presenting into a webcam in front of essentially 1 person, you’re speaking to 1 person, despite the fact that there are 700 some people that have purchased tickets to attend, you really are only speaking to that one individual at any given moment. It is pretty difficult to translate from in-person to live, given that you’re missing that energizing element.
Rob: Yeah. Personally, I’ve had to really work on learning to talk to a camera because obviously I’ve talked to MicroConf for more than a decade now, and I’ve talked on stage to an audience for more than a decade now, and each of those things were terrifying at the start, and I learned to do them and now I feel fine doing them. I feel like I definitely got better over the years at it.
Talking to a camera with no audience or just with the camera people around is way different, and it is hard to bring the energy. It’s hard to not be self-conscious. It’s hard not to stumble. You’re so distracted staring into this lens. You don’t feel like people are there, and it has literally taken me a year.
I think the first decent video we recorded for MicroConf was last October or November and was rough. It took me a bunch of takes and it wasn’t very good, and each one I went back and watched a few of them the other day and it made me feel good. It was like, oh, I am actually better than I used to be.
You’ll feel like your own worst critic. Even when I watch footage of Remote, I’m like, oh, I shouldn’t have done that or I should have said that better. When I go back to 11 months, I’m like, oof, now, I’m doing okay. That’s it. It’s a learned skill and I think it’s tough for presenters if you don’t have a lot of experience with it. It just takes time to get better at that.
Xander: The difference between scripted and prerecorded elements versus the live conversational elements is acting. When you’re in front of a camera and you have a script and there are peaks and valleys in the direction that that script is taking, you have to provide that level of acting and impart a little bit of emotion to it that you normally wouldn’t experience if you’re just having a regular conversation.
The example that I pulled from this was, Rob, we had you recording on the green screen right at the day before the event, and I had asked you to do these like little Peppy, welcome to MicroConf. Let’s get the show started, and we ended up pulling each of those because it just didn’t feel perfect. It didn’t feel as natural as we would want it to. To do a scripted element like that without having it be just this solid piece of content that felt great, you get to edit those types of things out. That’s not to say your energy wasn’t awesome, Rob, but it just didn’t feel like it was that genuine emotional experience that we would be trying to convey. I just scrapped those pieces because it felt like it wasn’t needed in order to advance the show.
It is definitely different. There’s a lot of acting when it comes to presenting to a camera, especially in those pre recorded elements. You want to make sure that the tone that you’re bringing to the expression that you’re delivering is matching up with the words that you’re saying.
Rob: Yeah, it’s weird. You said you’re not saying my energy wasn’t good. I’m saying my energy wasn’t good. I remember being like, this sucks, and I’m trying to pump myself up but I am not to get myself pumped up type of person.
Xander: Welcome to MicroConf. That sounds awful. What’s being fun about that?
Rob: It’s so interesting because when I watch people… We got acquired by LeadPages, they had a full-time videographer and they just cranked out videos and that was it. I would see people be extremely natural in conversation much like you and I are being very natural in our conversation right now.
When we’d watch the video back, it wouldn’t be any good. Like it looked terrible, and then I would watch someone record and I’m like, this guy’s acting. He’s not even talking the way that we do when we normally are hanging around, having a cappuccino, and he’s sitting there. It felt weird in person but on the camera, it felt great, and that’s this weird translation thing until that clicked for me, like I hadn’t realized that that’s what you had to do. The camera just requires a different level of emotion or energy.
To move it along, some things that we considered in terms of remote, obviously, we had to translate it from an in-person event to an online event to figure out what was different. We thought a lot about time zones. We were going to do it at 9:00 AM Central and it wound up being 11:00 AM.
We moved it this way because of California and then we moved it that way because of Europe, and we realized that in Asia it was going to be 2:00 in the morning, Asia and Australia. At a certain point, you just can’t do it perfectly. We actually toyed around with the idea of trying to do 12 hours or trying to do like a 3:00, 3:00, and 3:00 at different times of the day for different things, and realistically, we’re like, look, it’s our first big event like this. Let’s bite off what we can chew and not get too crazy with it.
Xander: Totally, yeah. Choosing time zones as always is a challenge. We see this in MicroConf Connect all the time where we do have a majority of the members of Connect, and really the majority of our audience is US-based. There is an element of needing to cater to the primary source of your audience and produce content in program times that are going to be the most accessible to those folks.
We do want to recognize that our audience is pretty expansive, and so we try to do as much as we can to cater to those individual time zones as much as we possibly can. But when it came to the live implementation of this event, we knew that the core of the audience was going to be coming from the US, and that we could make the recordings of the events available afterward.
If nothing else, we were able to make MicroConf Remote available to anyone to consume at any time. It’s just a matter of when we work in choosing the timeframe for the actual live event, so we just had to keep in mind to who was going to be our largest source of audience, and then what could we do to make sure that they were getting the best out of their experience that we could possibly create.
Rob: Another thing was the ticket price. Five years ago, I remember we were really saying should a virtual MicroConf event, should it be premium, should it be $100 a pop, or should it be trying to get the most people into it, so make it like $5 or $10 a pop. We were back and forth, back and forth, and I was on the charge more camp if I recall.
Then I bounced and said, oh, it should be $10, and then when COVID started we’re like, do we just try to make it free? Well, we can’t really pay for that studio and all of that. There’s quite a bit of expense incurred with it, so then we went to $10, then we went to $99, and then went to $50.
What we wound up I think, it was a cool hybrid, and you basically made the call on this in the end and you were like, look $50, but easy opportunities to get discounts. There was like if you recorded a 60-second intro to you and your founder story, you can get half off. I think if you poked around on the website somewhere, you could get it for like $10. You get like 80% off, and that was a clever way of having options.
Xander: I will say this. I am a firm believer that remote events should not be charging the same ticket price as live events. I think that the experience is vastly different. I think that the expectations are so easily managed within a virtual event that you should be able to really hone back on some of the fluff that’s associated with your live events that can trim that ticket price down.
The ticket prices do margins on events in general, are so well, that it’s something that you really need to play around with what those ticket levels are going to be. The difference between a digital and a live event in terms of the expense and the overhead that’s connected to those events is so vastly different that there is almost a degree of disingenuousness when you’re choosing to charge the same amount for a digital event as you would for the live version.
It goes back to the idea that MicroConf Remote was never meant to be a replacement for MicroConf Growth, their starter, or one of our live events. It was always meant to be this standalone, lower cost, more easily accessible program. It’s why we didn’t just say, hey, we’re canceling MicroConf Growth Minneapolis and we’re going to turn it into a digital event.
Then a certain view we’re going to get the same value at a $999 ticket price as you are going to get from MicroConf Remote. It didn’t feel right. It doesn’t feel like there is that connection to live and digital events that allow you to charge the same amount of money for that experience.
That was always the plan was to have it be a super low-cost event. We talked about those $10 ranges. We talked about that $50 price point, which is where we ultimately settled on our core pricing. A vast majority of the attendees paid between $10-$25 for their tickets, whether it be through their stories, submissions, or them poking around the website and finding one of those Easter egg discounts that were available.
Those were present throughout the ticket buying experience, and so we wanted to make sure that people could purchase at the level that they felt most comfortable at, while we were still able to make at least the margin that we needed in order to be able to afford to host the event.
Rob: We’re going to now talk about what worked and then things we would improve or do differently next time. We have quite a few of them, so we might need to zip through them pretty quick based on time.
I think the idea of ticket prices and selling tickets kicks us into this first one of what worked is I think we did a good job generating interest in marketing the event. We sold just under 700 tickets, and I was pretty happy with that. I think that tells us that the pricing was probably within the realm of where people expected it to be, and certainly, the biggest MicroConf event prior to this is essentially growth every year, which runs about $275, I believe. Obviously, digital is very different than in-person but still to sell that many tickets and have close to that many showing up in the stream. I consider it a win.
Xander: Yeah. You have that opportunity to sell tickets up until the day before the event. Your ticket sales runway is so different from a live experience where you have to not only buy your tickets, but you have to buy your flights, you have to buy your hotel rooms, all this added expense, and added time that’s needed in order to prepare for those logistics.
We were able to sell those 700 tickets in less than a month and so it felt like it was definitely an interesting prospect when you consider the 6-8 months that you want to have in terms of runway to sell tickets to a live event. This just feels like it’s an easier outlet to be able to increase your event capacity, to be able to welcome more people into the experience. I think that is one of the more unique elements of digital and remote events that worked well for us.
Rob: Something else I think worked is the programming itself, like just the talks, the segues that you had set up, the quick tips, the interviews, and just the actual each of those things. There were like one or two segments, I think they weren’t great. Mike and I are doing the analysis of the slides and stuff. Whose slide is it any way, where we have to do improv? Let’s be honest, Mike and I maybe not the best improv comedians. I mean, but that was like 12 minutes long, and it’s like, okay, we punted on it, but I think overall in general, like the programming itself felt solid to me and the transitions and stuff.
I also felt like we just experimented with formats quite a bit. You had the quick tip, we had keynotes, we had live Q&A, and we had interviews, AMA style. We had Nate Grahek was actually more of a teaching session, we asked him one or two questions and he taught. We had Sherry and I in the car, not getting coffee, like that was just a fun little thing that people commented on. I felt like the experimentation there and the programming itself was a hit.
Xander: Yeah, TV. It goes back to that concept of bingeable TV, like a sketch show, interdimensional cable, or something like the small bits that have nuggets of information that you can pull from them primarily inspirational. I think that that was one of the things we were leaning into with MicroConf Remote is that during COVID, things have just not been exciting, not been great, and there have been a lot of people that have been going through some pretty significant hardships.
We wanted to lean into the inspiration that comes with building SaaS and building these events, and they’re building these products and companies is that there is a light at the midway through the tunnel of building these products, and hopefully, people were able to latch on to some of the more inspirational elements coming from the events to carry them through the end of this year which is going to be just as interesting to see as the next three months to how the rest of 2020 pans out. Hopefully, this event was able to give that level of inspiration that we were trying to achieve.
Rob: Audience engagement, I think was another one. You had both with Q&A where some folks are willing to come on and actually do video questions, which is cool, but there were ample typed questions that I can then read and engage with.
As well as surveys that you had going on during the event, which I think was cool. If you’re watching something and you got bored, there was a way, go and take a survey and then that poll would then appear later in the event.
Xander: Yeah. I think that one of the pieces of feedback we got a lot of, which personally is a really nice piece of feedback in my perspective, is that people weren’t expecting this to be an active engagement event. They were expecting to sit down and just watch or listen to people speaking and the fact that there were a few layers of engagement that they were actually able to participate in. If they were aware of it, it was pretty cool.
I think that is the goal of these types of digital events is you want to recreate some of those elements. You want to do that translation of that in-person event into a live event, and there are only limited opportunities for you to do that, and so I think that people being surprised by some of those elements that we did leverage whether it was the Q&A, the surveying tools, the attempted recreation at the hallway track. I think some things that people could get excited about and could lean into that were different from just a generic digital event experience.
Rob: Another thing I feel like you did a really good job with is more than any other time you headed up finding speakers for this event. One of the goals we always have with MicroConf is to make them as diverse as possible, both racially and just gender-wise just underrepresented people.
Well more in the audience and we want what we can control which is having more of them on stage. I feel like as challenging as it was, I know that you sent a lot of emails and asked a lot of folks and got a lot of nos or no responses. You did a pretty good job of filling out the docket with a relatively balanced stable of speakers.
Xander: Yeah. I will say that the diversity of our speakers and lineups is one of the most important things that I have my radar on as we’re programming this content. It’s something that we’ve talked about since the day that I started working on MicroConf. I know it’s something that was on your radar and something you were planning for since the inception of the event.
I will say that it is one of the most difficult things to ensure as you’re putting together a lineup. You want to make sure that the messaging and the actual content is in line with the expectations of the audience in terms of indie funded bootstrapped founders that have built up products that are primarily SaaS that are reaching a market that is generating XYZ, MRR.
We can find a ton of people within that sphere, but in the process of searching for those folks, I put out 40 different asks that were either rejected, or we just weren’t inlined with the timing of the event, or the goals that that person had when it comes to presenting to an audience.
While the diversity of the lineup I am pretty proud of, it’s never really enough. It’s never enough to just say, hey, here’s what we’ve done and what we’re going to try and continue to do. It’s that active work that goes into finding people that are going to be a match for your values and your mission statement that you’re putting out as an organization, but are also representative of the world at large.
I think it’s so important to make sure that that stage is representative of who we want to be in our audience, and we know that it will never be enough, but if anybody has suggestions for female speakers, speakers of color. Just really anybody that can contribute to the diversity of ideas that are being presented from the MicroConf stage, please send them over to xander@microconf.com.
I’m more than happy to fill those requests and have conversations with anybody that is looking to get into either speaking at events, or that has recommendations for speakers that fit within that sphere.
Rob: Yeah. It’s tough to be in technology because it is so imbalanced. Especially when you get into software, and then you get into SaaS specifically, and it’s something we’ve constantly been putting thought and time into. I love the progress we’ve made over the last decade of having zero underrepresented founders in the first year and then having one the second year and each year.
It’s just a little more and I think these are the types of things that change over the years or decades. Unfortunately, they don’t change overnight but it definitely, I appreciate all the work. I always appreciate all the work you put in. People don’t realize you do 40 asks in order to try to get the best and most diverse lineup and it takes a lot of hustle. It doesn’t just fall in your lap.
I think that rounds out what worked with the event. Obviously, there are more things, but just in the interest of time. We have a few things that I feel like we could improve in future events, given that this was our first time doing essentially, a big online remote event like this. I think the list is good. Like it’s a good amount of learning that we got from these events.
Xander: We learned a ton. That is so true.
Rob: That’s the thing. The first one is just Shindig, which is that the software platform used really didn’t live up to what we needed. It was both in the broadcasting of it. I think you were saying people were like not seeing audio, not seeing video, not seeing this part, and not seeing that part.
Then when people tried to connect in the hallway track where we were trying to connect individuals like that part weren’t necessarily functioning. Of course, you spent dozens of hours evaluating (I don’t know how many tools) six, eight tools across a wide range of technologies, a wide range of prices, and all that stuff.
Everybody promises the world and then you get in and the day off during a livestream, that thing doesn’t work. Someone suggested as well, we could try this on a more local event like try with only 100 people. If we had done that, it probably would have worked just fine, and then when we went to 570 at our peak, it wouldn’t work.
Having an in-between I don’t think actually helps. It fails at a certain point. It’s somewhere between 400 and 600, I think is where things started falling off the bus, and so unless we had that many people, I don’t think because it truly was a scale thing was my understanding.
Xander: I think that there was a bit of a balance there were the issues that we ran into seemed likely we were going to run into those same issues at 100 attendees. The platform itself, at one point, completely locked me out as an admin being able to run the show, being able to upload feeds, being able to manage changes to individual feeds as they were being streamed there.
I will say that the reason that we chose Shindig was the implementation of the networking element. It created this sentiment of being seated at a table with other guests that were in attendance. You can control the number of guests that were seated at each table. That was one of the parameters that we had set for them to only have 10 people per table there were seating up to 30 people at each individual table all the way without following the parameter that we set in the back end.
There were a lot of little bugs and glitches that were peppered throughout the back end of the software that didn’t follow the inputs that we had submitted. This is like any other SaaS product that has a robust back end that it could be adjusted to meet the expectations that you have as a user of that piece of software, but the glitches and the breaks that were happening were based around some of those particular inputs that you had.
There was really very little way to recreate that type of experience ahead of the event as an individual producer. These are things that I am sure that the technology has gotten feedback on prior to, that wasn’t the feedback that I have got when I had talked with them to really investigate whether the platform would be usable for us. It wasn’t in the end of the referral information that I had pulled from some of the industry folks that were using the tool.
The software itself, I can hope that it is moving in a direction that it’s going to solve the problems that it does have in place because if it does, then I think that the concept of the hallway tracker, the networking elements of the event experience would be amazing.
It said that it did the thing that we were looking for in a product. There are tons of them out there. We looked at some of the more enterprise-level like an expo. We looked at livestream. We were considering using just YouTube and Slack which is something we’ll get into a little bit later.
We had to explore to hop in… There were a number of tech products that were doing similar things to different varying degrees of success with their users themselves and Shindig was the platform that had ticked a number of the boxes that we were looking to maximize on, or it ticked a number of the boxes that we were seeking out in a platform. Ultimately, without having 500-700 test cases within an infrastructure, you’re only able to see what it can do under that mass of execution when you have that number of people in a space. It was daunting, I will say that.
Rob: Yeah. Another thing that I feel like we could improve is that we’ve commented on how this event was different or is different than an in-person MicroConf. I’m not sure how much that fully sunk in for me until we were doing it, but I was there. I was like, yeah, this is not a regular MicroConf. I don’t know that we communicated that in crystal clear terms to people.
We got, I believe it was like 70% first-timers who had never been to a MicroConf, which is great. I mean, that’s part of the beauty of remote, but the 30%, who had been to one may have expected this to be like a MicroConf event that was filmed in live stream and that isn’t what this was. We mixed it up. I think setting that expectation next time would probably be beneficial.
Xander: Yeah, I would tend to agree with that.
Rob: The last one you have your pivots, Slack and YouTube. What do you think in there?
Xander: Yeah. In the midst of the show, we ended up just leaning on some of the tools that we have been using for the last four months when some of the videos and audio feeds were going down for individual users. We were streaming our signal out including both the video and the audio streams, but there were points where the screen was blacking out for one of our presenters. There were elements where the audio would cut and it would just be the video.
What we ended up doing is taking the actual stream from that we were patching into Shindig, and we just sent it straight into YouTube. We had our MicroConf Connects channel that was running side by side with a YouTube stream for people that weren’t able to actually use Shindig as a platform.
To be able to make that pivot and to implement these alternative resources in the midst of an event, I think that’s something that you wouldn’t often see at a live event. Either you wouldn’t be able to make that quick switch and have a similar experience in a live event. If you have to change hotels, if you have to change rooms, meeting spaces, and things like that, you would find yourself in a bit of a struggle in order to execute that in a pretty quick turnaround sense. I think that that was something that was successful based on some of the challenges we ran into using Shindig.
Rob: Yeah. Kind of reminds me of a sprinkler going off and having to move for himself. Too soon.
Xander: Yeah. That stuff.
Rob: All right. Well, sir, thanks for coming on and reliving the victories and some of the struggles and things we would do differently next time. It was a heck of an event to mark your one year anniversary working full-time on MicroConf.
Xander: Yeah, it was a good time. It was a struggle. There were some significant pitfalls in that you have to get past those as a producer. Everything is moving so quickly, you’ve got to step past them and move on to the next thing as quickly as you can in order to keep the show running. As they say, the show must go on.
Rob: All right, sir, and if folks want to see what you’re working on, microconf.com, so much of what goes up there is you and if they email support@microconf.com, they can send feedback directly to you.
Xander: Totally.
Rob: All right. Thanks again for coming on the show.
Xander: Thank you so much. It was a pleasure being on for my first time after all these years.
Rob: Awesome. I hope it was interesting for you to hear some of the inside baseballs around MicroConf Remote. Thanks again to producer Xander for joining me on the show. That’s it for this week. Although there will be another episode of TinySeed tales in your earbuds this Thursday morning. I hope you’re enjoying season two so far, so thank you as always for listening to Startups For the Rest of Us, and I will be in your earbuds again next Tuesday morning.
Xander has a background in event production. He’s been on the venue side. He’s been involved in events for like a decade. It’s a pretty extensive experience he’s had running events, and he does some pretty amazing things for us. If you’ve ever been to a MicroConf, we often get the question, how big is your staff for running this event?
He’s always like, oh, it’s just me and the founders, and people are like, whoa, because most events when we used to do starter and growth back to back and they’re 450 people there over the course of 4 ½, 5 days. You just have a whole event staff doing things and we really haven’t.
We really are that scrappy. Still continue to be that scrappy bootstrapped MicroConf ethos event and producer Xander is a big part of why we’re able to pull that off. We have a great conversation about MicroConf Remote. There’s a lot of inside baseballs, so if you don’t care about it, that’s fine, too.
We’ll be back next Tuesday morning at the normal time, but we talked about the event, why we wanted to do it, some of the challenges and things we considered. We talked about what worked really well and some things that we would do differently next time. With that, let’s dive into my conversation with producer Xander Castro. Xander Castro, thank you so much for joining me on the show.
Xander: Hey, thanks for having me the first time.
Rob: Indeed, so if you go to startupsfortherestofus.com and you search for the phrase Xander, I believe you’ve been mentioned. You just keep scrolling and scrolling, and there’s the next page. Producer Xander has been mentioned many times on the show, but you have yet to be in a conversation here.
For folks who don’t know, they would have heard a little from your intro button. You’ve been working with us on MicroConf since 2014 if I recall so quite a few events, and then you came on full-time just over a year ago, congratulations. Happy anniversary.
Xander: Well, thank you. It was a fun anniversary, wasn’t it?
Rob: Yeah. You’ve been working with us full-time on MicroConf on the big expansion in 2020. On your one year anniversary, we put on MicroConf Remote, which is what we came to talk about today. I did want to take a step back, though, and comment like 2020, we planned for seven in-person events. We were going from three up to seven, and then we were going to go from zero remote events or virtual events to two, and really, we haven’t done any in-person events.
Xander: No, no. 2020 has really dealt us the hand, everybody has been dealt, pretty much anybody that is producing live events right now is seeing a pretty rough year. There’s a lot going on right now and there’s much more that isn’t going on right now as a result of social distancing, quarantine, and whatnot with COVID-19.
Rob: Yeah. It feels like such an absolute dumpster fire in terms of trying to get people together. I don’t know about you, I want a do over.
Xander: Tell me about it. The live events industry is one that brings in like $6 billion a year annually just in the US. You just imagine all of those different staff members that are not working right now, and it’s just pretty devastating. It’s a rough industry to be in, that’s for sure at this point.
Rob: Yeah. A lot of folks have turned to virtual events, and that’s one thing that I wanted to say right off the bat is like we planned over a year ago to do two virtual events this year. At least two because we did the State of Independent SaaS Livestream back in January, and then we had decided we named it MicroConf Remote. Remember, we’re trying to figure out a name MicroConf, virtual MicroConf digital, MicroConf online, and we just loved Remote because of the idea of remote work.
We announced all of this last December but literally just about a year ago had said we’re going to do this thing. The fact that COVID happened really didn’t change those plans.
Xander: No. Not for MicroConf Remote, that’s for sure. I think we had always had this idea in mind about there was time to create a virtual implementation of what is MicroConf to really create a more accessible event that anybody around the planet would be able to access as they were interested and there weren’t those barriers to entry such as travel, setting aside over three-day plan to get out to a destination to attend a live event.
I think we always knew that creating something that was definitely more accessible to a mass audience was the route that we wanted to take with the remote version of MicroConf, for sure.
Rob: Yeah. We had been talking. You, Mike, and I believe talked about it four or five years ago about trying to do it.
Xander: Like in Barcelona.
Rob: Yeah. It’s been on our mind, but I know that it wasn’t like the highest priority because if you can do in-person events, I mean, personally, I think they’re just, I don’t know, better. I like in-person events because you have to travel. They’re more expensive, there are all these things, but there’s just a value there I think that is pretty much impossible to replicate online, so we had never prioritized it.
With this expansion, we did want to dip our toe in the water and get a little better at it, and so really, as I said, decided to do it last fall. I think we had talked for a while about not making it a replacement for MicroConf because an in-person MicroConf is so unique, and there’s so much about the setup in the hallway track and this and that, that we weren’t trying to replicate it.
We’re trying to do something a little different, and I think that’s a challenge and I think honestly if it hadn’t been for COVID, I think MicroConf Remote would have been even more unique than it was because there wouldn’t have been a bunch of other virtual events around it. We were in essence competing with these other Zoom events, but a lot of other online events, so we had to stand out that much more.
Xander: Definitely. As we were going through the research phase of what it would look like to implement MicroConf Remote back in November or December of 2019, we had done a bunch of customer interviews that focused around what it meant to attend MicroConf and what were the things that were drawing you to our live events. That person to person interaction was one of the high and above elements that people were seeking out when it came to attending MicroConf.
Even as we were in the midst of planning MicroConf Remote, we spent a little bit of time talking about how it wasn’t going to be a live version of MicroConf. I joked around saying that we should just brand it as not MicroConf because it was a unique way to look at what our attendees are constantly seeking, which is that person to person connection.
It’s an industry that few people that are innocent bystanders on the side looking inward don’t really understand the mechanics of starting your own business, doing the daily grind at home, not really being able to get out. A lot of people are starting to understand that more of these days.
I think that one of the things that we consistently try to achieve at our live events is the connection that’s formed in the hallway track. Trying to replicate that in the digital setting, as we’ll talk about a little bit later, is a challenge. It’s not the same type of experience you would see in a live experience when you’re shaking hands with someone which we should talk about. This is probably not going to be something that we’re going to encourage during live events, even when we’re able to get back together, but I think that trying to replicate that was something that took a lot of consideration and something that we were hoping we could emulate for sure.
Rob: We weren’t trying to replicate, we were trying to translate from in-person to online.
Xander: Yeah, absolutely.
Rob: Just to give an overview. We sold just about almost 700 tickets, and so quite a few listeners will probably have bought tickets and may have attended or seen the video. In essence, we decided to do a 5-hour livestream. Parts and parts of it were pre-recorded. We had some people pipe in with quick fixes that were two, three, five minutes.
Sherry and I did founders and cars, not getting coffee, a segment that had to be pre-recorded because we couldn’t do live streaming from a car. But most of it was truly live and whether it was, I interviewed a few people. We had for keynote talks, a lot of Q&A, and live interaction, which again, is one of the benefits of live streaming.
You went all out. You flew into Minneapolis and rented a studio where we had (if I recall) three cameras on me at all times, which was fun, but also like, geez, I can’t even scratch my nose without it having six angles of it.
Xander: You’re going to be caught at every angle.
Rob: Every angle, and then were there like seven people working on it, six- or seven-person crew?
Xander: Four behind the scenes and then we had three that were upfront helping with the filming, lighting, teleprompt, and things like that plus me.
Rob: That’s eight people in just the technical production of it. Of course, I’m up on stage, and then Tracy was doing a bunch of live customer support because when you have that many people attending, at our peak, I believe we had 570 attending the event. That’s just a lot of people doing stuff, so it was a real baller setup.
We kept saying, hey, this is going to be a different event. This is not just a host sitting in his bedroom in front of you. I’m in my bedroom office right now for example, but we didn’t just want that to be people in front of webcams. It gives that live feel to it because I was on different sets.
I was between two different sets, and I was on a talk show. We had like a talk show format, and we had a bunch of different creative elements to try. We knew the content would be startup focused. It’s similar to the content we would have in MicroConf or on this podcast, but with more live interactivity, but you really double down on the creativity of the visual elements to make the experience different for people.
Xander: Yeah. The goal was to really create something that would be considered bingeable. Something that carries you from segment one to segment two, or to keynote speaker, to the Q&A elements. We really wanted to keep things pretty tight in terms of the timeline of presenters, nobody had more than 20 minutes to deliver their own individual element or talk.
We wanted to create that sense of forward momentum, that idea that you’re going to sit down and you’re going to take in five hours of essentially TV. How can we make it so that each element leads into the next but is entertaining enough to really feel like it’s worth spending that much time? When it comes to digital events, even with the 700 some tickets that we sold, seeing that we had 575-ish folks that were on at peak, that’s a pretty significant number of people that are not engaging.
The idea is that you see anywhere from 50%-60% fall off when people purchase tickets to when they actually attend the event when it comes to digital experiences. We wanted to give everyone who chose to tune in a reason to stay versus just presenting the content the way that we had set it up and then distributed.
We wanted to make sure that there were these engaging touchpoints. I will say we recorded almost everything in advance of the event as well, just in case there were catastrophic failures across some of the technology, so we had those backup elements so that we could auto throw to it so nobody would miss anything.
There were some issues with that we’ll talk about in a bit, but there was a lot of thought that went into creating a through-line and the streamline story from the opening of the shows through to the closing Q&A with Jason Fried. I think that there was a lot of thought that went into how to create that line, but we wanted to make sure that it was being presented in a way that copies of people’s attention in-between each of the keynote sessions per se, and that kept it moving forward.
Rob: There’s a point. I think translating an in-person event to an online event, we didn’t just want to put on a MicroConf and have a camera there live streaming it, because we could have done that. We could have either flown speakers in or we could have sent a camera crew to every speakers’ place and just have them sit on a stage and we just don’t think that’s going to work the way that it should. It’s not the optimal translation. As I said earlier, we’re not replicating, we’re translating. We’re trying to adjust it.
Xander: Exactly. As you think about like transcription. These services that are talking about hey, can we get up to 95% accuracy? The translation between a live event and a digital event is not 1:1. There is going to be a fall off in terms of the experience the guests are having.
In theory, the keynotes and the content should be pretty much lined up with the expectations that they have going into the event. But when you go to a live event, you have that interconnectedness to the crowd. You have that sense of energy and that moment where a speaker says one individual thing and everyone’s ears perk up, or there’s a laugh that comes across the crowd. That’s an intangible experience that you really cannot create in a remote or digital setting.
There are some challenges in putting forward content that in a live event, it would originally be meant to be experienced and mass. When you’re presenting into a webcam in front of essentially 1 person, you’re speaking to 1 person, despite the fact that there are 700 some people that have purchased tickets to attend, you really are only speaking to that one individual at any given moment. It is pretty difficult to translate from in-person to live, given that you’re missing that energizing element.
Rob: Yeah. Personally, I’ve had to really work on learning to talk to a camera because obviously I’ve talked to MicroConf for more than a decade now, and I’ve talked on stage to an audience for more than a decade now, and each of those things were terrifying at the start, and I learned to do them and now I feel fine doing them. I feel like I definitely got better over the years at it.
Talking to a camera with no audience or just with the camera people around is way different, and it is hard to bring the energy. It’s hard to not be self-conscious. It’s hard not to stumble. You’re so distracted staring into this lens. You don’t feel like people are there, and it has literally taken me a year.
I think the first decent video we recorded for MicroConf was last October or November and was rough. It took me a bunch of takes and it wasn’t very good, and each one I went back and watched a few of them the other day and it made me feel good. It was like, oh, I am actually better than I used to be.
You’ll feel like your own worst critic. Even when I watch footage of Remote, I’m like, oh, I shouldn’t have done that or I should have said that better. When I go back to 11 months, I’m like, oof, now, I’m doing okay. That’s it. It’s a learned skill and I think it’s tough for presenters if you don’t have a lot of experience with it. It just takes time to get better at that.
Xander: The difference between scripted and prerecorded elements versus the live conversational elements is acting. When you’re in front of a camera and you have a script and there are peaks and valleys in the direction that that script is taking, you have to provide that level of acting and impart a little bit of emotion to it that you normally wouldn’t experience if you’re just having a regular conversation.
The example that I pulled from this was, Rob, we had you recording on the green screen right at the day before the event, and I had asked you to do these like little Peppy, welcome to MicroConf. Let’s get the show started, and we ended up pulling each of those because it just didn’t feel perfect. It didn’t feel as natural as we would want it to. To do a scripted element like that without having it be just this solid piece of content that felt great, you get to edit those types of things out. That’s not to say your energy wasn’t awesome, Rob, but it just didn’t feel like it was that genuine emotional experience that we would be trying to convey. I just scrapped those pieces because it felt like it wasn’t needed in order to advance the show.
It is definitely different. There’s a lot of acting when it comes to presenting to a camera, especially in those pre recorded elements. You want to make sure that the tone that you’re bringing to the expression that you’re delivering is matching up with the words that you’re saying.
Rob: Yeah, it’s weird. You said you’re not saying my energy wasn’t good. I’m saying my energy wasn’t good. I remember being like, this sucks, and I’m trying to pump myself up but I am not to get myself pumped up type of person.
Xander: Welcome to MicroConf. That sounds awful. What’s being fun about that?
Rob: It’s so interesting because when I watch people… We got acquired by LeadPages, they had a full-time videographer and they just cranked out videos and that was it. I would see people be extremely natural in conversation much like you and I are being very natural in our conversation right now.
When we’d watch the video back, it wouldn’t be any good. Like it looked terrible, and then I would watch someone record and I’m like, this guy’s acting. He’s not even talking the way that we do when we normally are hanging around, having a cappuccino, and he’s sitting there. It felt weird in person but on the camera, it felt great, and that’s this weird translation thing until that clicked for me, like I hadn’t realized that that’s what you had to do. The camera just requires a different level of emotion or energy.
To move it along, some things that we considered in terms of remote, obviously, we had to translate it from an in-person event to an online event to figure out what was different. We thought a lot about time zones. We were going to do it at 9:00 AM Central and it wound up being 11:00 AM.
We moved it this way because of California and then we moved it that way because of Europe, and we realized that in Asia it was going to be 2:00 in the morning, Asia and Australia. At a certain point, you just can’t do it perfectly. We actually toyed around with the idea of trying to do 12 hours or trying to do like a 3:00, 3:00, and 3:00 at different times of the day for different things, and realistically, we’re like, look, it’s our first big event like this. Let’s bite off what we can chew and not get too crazy with it.
Xander: Totally, yeah. Choosing time zones as always is a challenge. We see this in MicroConf Connect all the time where we do have a majority of the members of Connect, and really the majority of our audience is US-based. There is an element of needing to cater to the primary source of your audience and produce content in program times that are going to be the most accessible to those folks.
We do want to recognize that our audience is pretty expansive, and so we try to do as much as we can to cater to those individual time zones as much as we possibly can. But when it came to the live implementation of this event, we knew that the core of the audience was going to be coming from the US, and that we could make the recordings of the events available afterward.
If nothing else, we were able to make MicroConf Remote available to anyone to consume at any time. It’s just a matter of when we work in choosing the timeframe for the actual live event, so we just had to keep in mind to who was going to be our largest source of audience, and then what could we do to make sure that they were getting the best out of their experience that we could possibly create.
Rob: Another thing was the ticket price. Five years ago, I remember we were really saying should a virtual MicroConf event, should it be premium, should it be $100 a pop, or should it be trying to get the most people into it, so make it like $5 or $10 a pop. We were back and forth, back and forth, and I was on the charge more camp if I recall.
Then I bounced and said, oh, it should be $10, and then when COVID started we’re like, do we just try to make it free? Well, we can’t really pay for that studio and all of that. There’s quite a bit of expense incurred with it, so then we went to $10, then we went to $99, and then went to $50.
What we wound up I think, it was a cool hybrid, and you basically made the call on this in the end and you were like, look $50, but easy opportunities to get discounts. There was like if you recorded a 60-second intro to you and your founder story, you can get half off. I think if you poked around on the website somewhere, you could get it for like $10. You get like 80% off, and that was a clever way of having options.
Xander: I will say this. I am a firm believer that remote events should not be charging the same ticket price as live events. I think that the experience is vastly different. I think that the expectations are so easily managed within a virtual event that you should be able to really hone back on some of the fluff that’s associated with your live events that can trim that ticket price down.
The ticket prices do margins on events in general, are so well, that it’s something that you really need to play around with what those ticket levels are going to be. The difference between a digital and a live event in terms of the expense and the overhead that’s connected to those events is so vastly different that there is almost a degree of disingenuousness when you’re choosing to charge the same amount for a digital event as you would for the live version.
It goes back to the idea that MicroConf Remote was never meant to be a replacement for MicroConf Growth, their starter, or one of our live events. It was always meant to be this standalone, lower cost, more easily accessible program. It’s why we didn’t just say, hey, we’re canceling MicroConf Growth Minneapolis and we’re going to turn it into a digital event.
Then a certain view we’re going to get the same value at a $999 ticket price as you are going to get from MicroConf Remote. It didn’t feel right. It doesn’t feel like there is that connection to live and digital events that allow you to charge the same amount of money for that experience.
That was always the plan was to have it be a super low-cost event. We talked about those $10 ranges. We talked about that $50 price point, which is where we ultimately settled on our core pricing. A vast majority of the attendees paid between $10-$25 for their tickets, whether it be through their stories, submissions, or them poking around the website and finding one of those Easter egg discounts that were available.
Those were present throughout the ticket buying experience, and so we wanted to make sure that people could purchase at the level that they felt most comfortable at, while we were still able to make at least the margin that we needed in order to be able to afford to host the event.
Rob: We’re going to now talk about what worked and then things we would improve or do differently next time. We have quite a few of them, so we might need to zip through them pretty quick based on time.
I think the idea of ticket prices and selling tickets kicks us into this first one of what worked is I think we did a good job generating interest in marketing the event. We sold just under 700 tickets, and I was pretty happy with that. I think that tells us that the pricing was probably within the realm of where people expected it to be, and certainly, the biggest MicroConf event prior to this is essentially growth every year, which runs about $275, I believe. Obviously, digital is very different than in-person but still to sell that many tickets and have close to that many showing up in the stream. I consider it a win.
Xander: Yeah. You have that opportunity to sell tickets up until the day before the event. Your ticket sales runway is so different from a live experience where you have to not only buy your tickets, but you have to buy your flights, you have to buy your hotel rooms, all this added expense, and added time that’s needed in order to prepare for those logistics.
We were able to sell those 700 tickets in less than a month and so it felt like it was definitely an interesting prospect when you consider the 6-8 months that you want to have in terms of runway to sell tickets to a live event. This just feels like it’s an easier outlet to be able to increase your event capacity, to be able to welcome more people into the experience. I think that is one of the more unique elements of digital and remote events that worked well for us.
Rob: Something else I think worked is the programming itself, like just the talks, the segues that you had set up, the quick tips, the interviews, and just the actual each of those things. There were like one or two segments, I think they weren’t great. Mike and I are doing the analysis of the slides and stuff. Whose slide is it any way, where we have to do improv? Let’s be honest, Mike and I maybe not the best improv comedians. I mean, but that was like 12 minutes long, and it’s like, okay, we punted on it, but I think overall in general, like the programming itself felt solid to me and the transitions and stuff.
I also felt like we just experimented with formats quite a bit. You had the quick tip, we had keynotes, we had live Q&A, and we had interviews, AMA style. We had Nate Grahek was actually more of a teaching session, we asked him one or two questions and he taught. We had Sherry and I in the car, not getting coffee, like that was just a fun little thing that people commented on. I felt like the experimentation there and the programming itself was a hit.
Xander: Yeah, TV. It goes back to that concept of bingeable TV, like a sketch show, interdimensional cable, or something like the small bits that have nuggets of information that you can pull from them primarily inspirational. I think that that was one of the things we were leaning into with MicroConf Remote is that during COVID, things have just not been exciting, not been great, and there have been a lot of people that have been going through some pretty significant hardships.
We wanted to lean into the inspiration that comes with building SaaS and building these events, and they’re building these products and companies is that there is a light at the midway through the tunnel of building these products, and hopefully, people were able to latch on to some of the more inspirational elements coming from the events to carry them through the end of this year which is going to be just as interesting to see as the next three months to how the rest of 2020 pans out. Hopefully, this event was able to give that level of inspiration that we were trying to achieve.
Rob: Audience engagement, I think was another one. You had both with Q&A where some folks are willing to come on and actually do video questions, which is cool, but there were ample typed questions that I can then read and engage with.
As well as surveys that you had going on during the event, which I think was cool. If you’re watching something and you got bored, there was a way, go and take a survey and then that poll would then appear later in the event.
Xander: Yeah. I think that one of the pieces of feedback we got a lot of, which personally is a really nice piece of feedback in my perspective, is that people weren’t expecting this to be an active engagement event. They were expecting to sit down and just watch or listen to people speaking and the fact that there were a few layers of engagement that they were actually able to participate in. If they were aware of it, it was pretty cool.
I think that is the goal of these types of digital events is you want to recreate some of those elements. You want to do that translation of that in-person event into a live event, and there are only limited opportunities for you to do that, and so I think that people being surprised by some of those elements that we did leverage whether it was the Q&A, the surveying tools, the attempted recreation at the hallway track. I think some things that people could get excited about and could lean into that were different from just a generic digital event experience.
Rob: Another thing I feel like you did a really good job with is more than any other time you headed up finding speakers for this event. One of the goals we always have with MicroConf is to make them as diverse as possible, both racially and just gender-wise just underrepresented people.
Well more in the audience and we want what we can control which is having more of them on stage. I feel like as challenging as it was, I know that you sent a lot of emails and asked a lot of folks and got a lot of nos or no responses. You did a pretty good job of filling out the docket with a relatively balanced stable of speakers.
Xander: Yeah. I will say that the diversity of our speakers and lineups is one of the most important things that I have my radar on as we’re programming this content. It’s something that we’ve talked about since the day that I started working on MicroConf. I know it’s something that was on your radar and something you were planning for since the inception of the event.
I will say that it is one of the most difficult things to ensure as you’re putting together a lineup. You want to make sure that the messaging and the actual content is in line with the expectations of the audience in terms of indie funded bootstrapped founders that have built up products that are primarily SaaS that are reaching a market that is generating XYZ, MRR.
We can find a ton of people within that sphere, but in the process of searching for those folks, I put out 40 different asks that were either rejected, or we just weren’t inlined with the timing of the event, or the goals that that person had when it comes to presenting to an audience.
While the diversity of the lineup I am pretty proud of, it’s never really enough. It’s never enough to just say, hey, here’s what we’ve done and what we’re going to try and continue to do. It’s that active work that goes into finding people that are going to be a match for your values and your mission statement that you’re putting out as an organization, but are also representative of the world at large.
I think it’s so important to make sure that that stage is representative of who we want to be in our audience, and we know that it will never be enough, but if anybody has suggestions for female speakers, speakers of color. Just really anybody that can contribute to the diversity of ideas that are being presented from the MicroConf stage, please send them over to xander@microconf.com.
I’m more than happy to fill those requests and have conversations with anybody that is looking to get into either speaking at events, or that has recommendations for speakers that fit within that sphere.
Rob: Yeah. It’s tough to be in technology because it is so imbalanced. Especially when you get into software, and then you get into SaaS specifically, and it’s something we’ve constantly been putting thought and time into. I love the progress we’ve made over the last decade of having zero underrepresented founders in the first year and then having one the second year and each year.
It’s just a little more and I think these are the types of things that change over the years or decades. Unfortunately, they don’t change overnight but it definitely, I appreciate all the work. I always appreciate all the work you put in. People don’t realize you do 40 asks in order to try to get the best and most diverse lineup and it takes a lot of hustle. It doesn’t just fall in your lap.
I think that rounds out what worked with the event. Obviously, there are more things, but just in the interest of time. We have a few things that I feel like we could improve in future events, given that this was our first time doing essentially, a big online remote event like this. I think the list is good. Like it’s a good amount of learning that we got from these events.
Xander: We learned a ton. That is so true.
Rob: That’s the thing. The first one is just Shindig, which is that the software platform used really didn’t live up to what we needed. It was both in the broadcasting of it. I think you were saying people were like not seeing audio, not seeing video, not seeing this part, and not seeing that part.
Then when people tried to connect in the hallway track where we were trying to connect individuals like that part weren’t necessarily functioning. Of course, you spent dozens of hours evaluating (I don’t know how many tools) six, eight tools across a wide range of technologies, a wide range of prices, and all that stuff.
Everybody promises the world and then you get in and the day off during a livestream, that thing doesn’t work. Someone suggested as well, we could try this on a more local event like try with only 100 people. If we had done that, it probably would have worked just fine, and then when we went to 570 at our peak, it wouldn’t work.
Having an in-between I don’t think actually helps. It fails at a certain point. It’s somewhere between 400 and 600, I think is where things started falling off the bus, and so unless we had that many people, I don’t think because it truly was a scale thing was my understanding.
Xander: I think that there was a bit of a balance there were the issues that we ran into seemed likely we were going to run into those same issues at 100 attendees. The platform itself, at one point, completely locked me out as an admin being able to run the show, being able to upload feeds, being able to manage changes to individual feeds as they were being streamed there.
I will say that the reason that we chose Shindig was the implementation of the networking element. It created this sentiment of being seated at a table with other guests that were in attendance. You can control the number of guests that were seated at each table. That was one of the parameters that we had set for them to only have 10 people per table there were seating up to 30 people at each individual table all the way without following the parameter that we set in the back end.
There were a lot of little bugs and glitches that were peppered throughout the back end of the software that didn’t follow the inputs that we had submitted. This is like any other SaaS product that has a robust back end that it could be adjusted to meet the expectations that you have as a user of that piece of software, but the glitches and the breaks that were happening were based around some of those particular inputs that you had.
There was really very little way to recreate that type of experience ahead of the event as an individual producer. These are things that I am sure that the technology has gotten feedback on prior to, that wasn’t the feedback that I have got when I had talked with them to really investigate whether the platform would be usable for us. It wasn’t in the end of the referral information that I had pulled from some of the industry folks that were using the tool.
The software itself, I can hope that it is moving in a direction that it’s going to solve the problems that it does have in place because if it does, then I think that the concept of the hallway tracker, the networking elements of the event experience would be amazing.
It said that it did the thing that we were looking for in a product. There are tons of them out there. We looked at some of the more enterprise-level like an expo. We looked at livestream. We were considering using just YouTube and Slack which is something we’ll get into a little bit later.
We had to explore to hop in… There were a number of tech products that were doing similar things to different varying degrees of success with their users themselves and Shindig was the platform that had ticked a number of the boxes that we were looking to maximize on, or it ticked a number of the boxes that we were seeking out in a platform. Ultimately, without having 500-700 test cases within an infrastructure, you’re only able to see what it can do under that mass of execution when you have that number of people in a space. It was daunting, I will say that.
Rob: Yeah. Another thing that I feel like we could improve is that we’ve commented on how this event was different or is different than an in-person MicroConf. I’m not sure how much that fully sunk in for me until we were doing it, but I was there. I was like, yeah, this is not a regular MicroConf. I don’t know that we communicated that in crystal clear terms to people.
We got, I believe it was like 70% first-timers who had never been to a MicroConf, which is great. I mean, that’s part of the beauty of remote, but the 30%, who had been to one may have expected this to be like a MicroConf event that was filmed in live stream and that isn’t what this was. We mixed it up. I think setting that expectation next time would probably be beneficial.
Xander: Yeah, I would tend to agree with that.
Rob: The last one you have your pivots, Slack and YouTube. What do you think in there?
Xander: Yeah. In the midst of the show, we ended up just leaning on some of the tools that we have been using for the last four months when some of the videos and audio feeds were going down for individual users. We were streaming our signal out including both the video and the audio streams, but there were points where the screen was blacking out for one of our presenters. There were elements where the audio would cut and it would just be the video.
What we ended up doing is taking the actual stream from that we were patching into Shindig, and we just sent it straight into YouTube. We had our MicroConf Connects channel that was running side by side with a YouTube stream for people that weren’t able to actually use Shindig as a platform.
To be able to make that pivot and to implement these alternative resources in the midst of an event, I think that’s something that you wouldn’t often see at a live event. Either you wouldn’t be able to make that quick switch and have a similar experience in a live event. If you have to change hotels, if you have to change rooms, meeting spaces, and things like that, you would find yourself in a bit of a struggle in order to execute that in a pretty quick turnaround sense. I think that that was something that was successful based on some of the challenges we ran into using Shindig.
Rob: Yeah. Kind of reminds me of a sprinkler going off and having to move for himself. Too soon.
Xander: Yeah. That stuff.
Rob: All right. Well, sir, thanks for coming on and reliving the victories and some of the struggles and things we would do differently next time. It was a heck of an event to mark your one year anniversary working full-time on MicroConf.
Xander: Yeah, it was a good time. It was a struggle. There were some significant pitfalls in that you have to get past those as a producer. Everything is moving so quickly, you’ve got to step past them and move on to the next thing as quickly as you can in order to keep the show running. As they say, the show must go on.
Rob: All right, sir, and if folks want to see what you’re working on, microconf.com, so much of what goes up there is you and if they email support@microconf.com, they can send feedback directly to you.
Xander: Totally.
Rob: All right. Thanks again for coming on the show.
Xander: Thank you so much. It was a pleasure being on for my first time after all these years.
Rob: Awesome. I hope it was interesting for you to hear some of the inside baseballs around MicroConf Remote. Thanks again to producer Xander for joining me on the show. That’s it for this week. Although there will be another episode of TinySeed tales in your earbuds this Thursday morning. I hope you’re enjoying season two so far, so thank you as always for listening to Startups For the Rest of Us, and I will be in your earbuds again next Tuesday morning.
