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
- Stay on Top of Your SaaS Metrics: Know What to Measure to Maintain Sustainable Growth – Craig Hewitt
- The 2020 State of Independent SaaS
- Indie Founder Bootcamp
- Castos Production (formerly Podcast Motor)
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
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!
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.
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.