
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
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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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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.
TinySeed Tales S2E8 | Upmarket Starts to Pay Off

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Brian & Scottie Elliott are the husband & wife co-founders of Gather, an interior design project management app.
Last time we spoke, they were bouncing back from the initial shock of the COVID-19 crisis with the potential to sign two large enterprise deals that could help them out with an ongoing cash crunch.
In this episode, Rob talks with them about customer-funded development, always following up when doing outbound sales, and restarting a productized service.
The topics we cover
[01:14] Status on large enterprise deals
- One closed, one did not.
- The first touch with them was almost a year.
- They had a software proprietary software that they built internally and have been actively seeking a new tool
- Custom data migration and storage and it was also a bunch of custom development
- Win-win they got what they wanted and we got some new cool features
- Big win, I would say, to get paid, to build a feature that you expect other customers to be able to use.
- Optimistic that maybe we can sort of like build the product that we want by closing these sorts of deals and move into the hospitality world
- Referred to as customer-funded development
[06:51] Obstacles remain for moving upmarket
- Outbound is not going as well as it used to.
- Inbound has been fine. It’s a little down this month over the previous.
- Always be following up.
- Never letting go until you’re explicitly told to go away.
- Making sure you never lose track of someone is like a huge win.
[10:03] Moving past uncertainty
- There is still uncertainty. I think there’s always that whether there’s a pandemic or not. When you’re first getting started and plugging along, there’s always that kind of like tension, wondering how this month is going to be.
- We have plenty of signals that people are willing to pay us quite a bit more than they were paying us.
- When we started there, we were charging $29 or $39 a month, which in retrospect is just, you know, terrifying that we were priced that low.
- If we can get to that traction where, you know, we are selling 10 new customers per month at the price points that we’re doing right now like it’s a game-changer.
[13:49] Restarting a services venture
- Brian and Scotty decided to dip their toes into the world of services with a virtual coordinator that would complement their software.
- The idea was to bring in some high-value clients and make some extra cash. And although they had to shelve it due to the COVID crisis, there’s been some renewed interest.
- Initially, we thought of the services side as a way to get some revenue fast.
- This is pretty high touch services but finding a team to help with the services side. And then of course we’d be using the software. To also manage the services, which could potentially drive some of the features that we build for the software.
- The most important piece and that is going to be the process of setting up SOP and figuring out how I can best. Manage the services side.
[19:23] Last week of TinySeed Tales
- So much knowledge gained and relationships built. It was a great year.
- I think not being able to meet in person in the year together feels like it’s still, like, there’s no closure.
- It does feel just sort of finished, not finished.
Links from the show
- Gather | Website
- Brian Elliott | Twitter
Thanks for listening to another episode of TinySeed Tales. If you haven’t already, be sure to check out Season 1 of TinySeed Tales where we follow the Saas journey with Craig Hewitt of Castos.
Episode 520 | Why a Million Dollar Agency Quit It All and Moved to SaaS

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
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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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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.
TinySeed Tales S2E7 | A Global Pandemic

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Brian & Scottie Elliott are the husband & wife co-founders of Gather, an interior design project management app.
Today’s episode was recorded after the COVID-19 shelter in place orders went into effect. We talk with Brian and Scottie about how the pandemic has affected Gather as well as their life beyond the scope of their business.
The topics we cover
[01:10] How the pandemic has affected their lives beyond the scope of their business.
- Brian and Scottie live in Mexico
- Living in almost what feels like two worlds here. The ex-pat community is very tuned into what’s happening in the US and sheltering in place
[03:11] Current financial situation
- Our situation hasn’t changed financially. I think that at the time we had hopes that we could raise some money or at least get alone. We’re not even pursuing that at this point
- We’re certainly used to bootstrapping and feeling that stress and coming up with interesting solutions to our cash problems.
[05:57] High point or biggest wins since the last episode
- We have had a couple of requests for enterprise plans, one existing customer that has a lot of data that they need to be migrated over and they have a custom feature that they want
- Then a new customer who has a custom feature in data migration.
- It’s unexpected. Feasibly you think they’re going to cut back expenses, but larger deals are coming your way.
- The churn that we have had has been largely solo designers and smaller firms
- One of the things of going upmarket, the typical pattern is there price sensitive, they churn less.
- We’ve had a lot of inbound interest and a lot of them are saying things like now that we’re home working remotely, we’re sort of investigating better ways to work online
[09:21] Impacts from the COVID-19 crisis and biggest setbacks so far
- Across the portfolio of companies that are part of TinySeed, there is about 15% that are having real struggles with the impact of the pandemic on the industry they serve. Another 70% are waiting to see what happens, perhaps cutting back on expenses and generally seeing a growth plateau. Then, there’s the 15% of companies for whom remote work is a boon and their growth is accelerating faster than ever.
- Gather has had to cut their developer contract in half
- Big features are kind of on hold for a little while
- Staying focused has just been difficult
[13:54] Fears and hopes for the future
- I think my biggest fear is that the trend that we’ve seen this month as being a big uptick in sales and opportunities is just a flash in the pan.
- In different times, we might be able to pivot if we needed to, but because of our financial situation it’s going to be hard for us to pivot out of it
- Looking forward to seeing how these enterprise deals play out
- Trying to figure out ways that we could get customers to pay for some of the features that we’d like to build
Links from the show
- Gather | Website
- Brian Elliott | Twitter
Thanks for listening to another episode of TinySeed Tales. If you haven’t already, be sure to check out Season 1 of TinySeed Tales where we follow the Saas journey with Craig Hewitt of Castos.
Episode 519 | Profit Sharing, Stock Options, and Equity (A Rob Solo Adventure)

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
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
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.
TinySeed Tales S2E6 | Best Growth Month Ever

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Brian & Scottie Elliott are the husband & wife co-founders of Gather, an interior design project management app.
On this episode, Brian and Scottie share with us an update on their unexpected MRR growth, the psychology of raising prices, and the difficulty of making decisions amidst a mountain of unknowns.
The topics we cover
01:07] Update on MRR growth since we last spoke
- Had a goal to grow a thousand dollars of MRR in a single month.
- Trailing 30 days is like $1,006.
- MRR is currently $8,200.
- Get caught up in the day to day to actually celebrate. Is good for us to stop and recognize that we have made a lot of progress.
- We’re still burning more cash than we’re making.
[03:53] Closing a large 20-person enterprise deal
- They did do a trial.
- Then they bumped up to an enterprise plan.
- You can have your sights set on a goal and before long you might achieve it. But that’s not the end of your journey. You’re onto the next hurdle.
- This is one of the things I’ve found so difficult about starting this kind of company, your to do list is never clear and things don’t end until you put someone in charge of the company or you sell it.
[05:47] Raising prices, again.
- We’ve even raised twice.
- Don’t get a lot of price objections.
- We have had to reject our previous customer avatar.
- Lower prices send a bad signal to them.
- The psychology of pricing, both at the founder level and also at the buyer level.
- This is a tried and true SaaS playbook. You start at the bottom of the market because you don’t have a brand and no one’s heard of you and your product is really early, and you don’t have the features that you need. You price yourself pretty low. You get a little bit of ttraction, use that to make a better product. You’ll find your positioning. You learn more about the market, and then you just go up, up, up from there.
- Lower price points, higher churn.
- A lot of people don’t realize product market fit is not just building a product that people want and are willing to pay for. It’s also having a good idea about your positioning and pricing and some idea of channels where you can reach future customers.
- You’re making a lot of decisions quickly with incomplete information and you only know which ones work in retrospect.
[12:21] Biggest wins so far and looking to the future
- In the beginning it felt a little bit scary and unknown when we were leaving, seeing the small teams.
- Biggest win: validating with these larger teams.
- Biggest win: we are selling into the kinds of firms that we hypothesized we could sell into.
- Doing these sales over the last couple of months has just taught me how to sell.
[15:33] Biggest fear right now
- That we’re going to run out of money.
- It’s scary to see the bank account dwindle.
- Just figuring out how we can keep going and keep growing and even accelerate growth.
- How are we going to cross this bridge? Because we can see the green pastures on the other side.
- Navigating a world that I don’t quite understand yet should be the title and subtitle and every subheading of being an entrepreneur.
- I’m most excited to see how we deal with this cash crunch that we’re heading into.
Links from the show
- Gather | Website
- Brian Elliott | Twitter
Thanks for listening to another episode of TinySeed Tales. If you haven’t already, be sure to check out Season 1 of TinySeed Tales where we follow the Saas journey with Craig Hewitt of Castos.
Episode 518 | A Live LinkedIn Ads Consult with Anthony Blatner and Scatterspoke

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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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.
TinySeed Tales S2E5 | The Gamble of Raising Prices

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On Episode 5 of TinySeed Tales, we learn about the success of their recent outbound email campaign. We also hear about their progress with raising their prices and transitioning away from Gather’s solo pricing tier.
The topics we cover
[02:00] Checking in on the past few weeks
- A little bit of an emotional roller coaster
- We have definitely made some inroads with teams
- We haven’t had the growth that we were hoping for
- Feeling a a little anxious about how it’s all gonna play out.
- There’s a time here where it’s very uncertain because you’re kind of leaving the solo practitioners behind, but you haven’t quite reached product market fit.
- There’s also a little bit of insecurity with the product
- It’s a huge mind shift all together selling into these teams
- We were hoping for more of a spike and it’s just been this slow, steady growth, which is not bad. It’s growing as usual, but that’s not helpful when you had to take all this risk
[05:51] Patience can be dangerous
- Going forward Gather will be dropping their solar plan altogether.
- Half of their signups in the last month have come from their new cold email outreach campaign that’s focused on larger teams.
- Had success from a customer development standpoint early on in the product before we ever even built anything. Brian was emailing tons of people and talking to them as much as I could
- We actually had quite a bit of traffic last month but the conversion rate was half what we usually have, so it just speaks to the fact that we aren’t speaking to the right people right now.
[07:31] Yet another pricing increase
- Currently they offer a tier at $99 a month and one at $159 a month, as well as a custom enterprise plan. That’s way up from $39 a month, which was their lowest price plan when they joined TinySeed.
- My feeling is that price is not really an objection when we’re selling to new people
- It’ll be interesting to see, you know, if we do start getting price objections from at least the solo people, we kind of predict that we will.
- Next month we’re planning on doing another potentially really big price jump.
- Raising prices is increasing the speed of learning and if it works, although it’s a big gamble, the payoff is pretty
- In order to keep this up, like we would eventually need to hire some sales reps and some account executive types.
- But when we move into this double triple price thing, you know, like into the, let’s say $250 average revenue per customer, Then the whole model shifts and changes and it looks way more interesting.
[15:19] High points from last week
- We did have to literally within five minutes of each other team annual signups. Both of them were from our cold email outreach and they had both had demos and that felt really good
- We had an existing customer that’s requested pricing for 20 teammates, so we provided a custom quote for them. But if they do decide to go ahead and sign on that, that will become our single largest customer, both in number of users in revenue as well.
Links from the show
- Gather | Website
- Brian Elliott | Twitter
Episode 517 | Married Co-founders Who Turned a Free Tool Into a Fast-Growing SaaS Product

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
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.
TinySeed Tales S2E4 | Being Married and Being Co-Founders

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Brian & Scottie Elliott are the husband & wife co-founders of Gather, an interior design project management app.
Today we’re going to dive into the stress that comes with entrepreneurship and how it shows up in their personal lives. Moving up from one customer segment to another is hard. Each customer segment is like an Island with a body of water between them. They’re crossing that body of water from servicing one and two-person teams to serving larger architecture firms with 20 person teams. We hear how they are managing this difficult and stressful moment both as co-founders and as married partners.
The topics we cover
[01:40] Leveraging testimonials when moving upmarket
- It’s an approach you should explore as early as possible when trying to move into a new segment of the market
- One of the reasons why trials are kind of a little bit lower this month is because some of the traffic that we’ve been getting is probably more geared towards the residential side and they’re seeing this new messaging.
- You have two islands and a body of water in between them and its messaging and sales process and pricing and positioning and all that around going after one person, two-person teams versus a 10 person team and those are the two different islands.
[06:09] Cold email experiments to attract larger teams
- Averaging 12-15 demos per week (initial goal was to get to 10)
- Finding one repeatable channel at this stage is huge
- Cold email has been the channel that has worked the best for Brian & Scottie
- Most businesses that start B2C end up transitioning to B2B and end up raising prices. Means less churn, fewer flakes for demos, better conversion.’
- Demo to trial isn’t as high as they’d like it to be.
- One reason for this could be due to the longer sales process
[11:27] Cashflow management
- We had a really good month last month — the best month we’ve ever had.
- The biggest stress is just around the channels that we’re investing in and wondering if they are going to perform like we want them to.
- These are challenges with going upmarket. First, you have to figure out if you have product-market fit with teams. Then you have to find a channel or two that work. If the channel works, do the people stick around and can you find enough people who sign up and stick around? Can you find them fast enough with the channels you have such that you don’t run out of cash
- At the current burn rate we have about 6 months cash in the bank
- If pushed, would consider debt-equity or debt financing as a fallback option
- Founders do all sorts of things to maintain their runway, including credit card debt, personal loans, raising funding, even borrowing from their 401k. But with each of these, you have to weigh the risks to the business, as well as your personal financial situation.
[18:09] Dealing with stress as entrepreneurs and a married couple
- The situation causes us to feel a little bit on edge and we have no one else to take it out on.
- Now we’re being much more conscious of our personal spending ad so I think that has also manifested itself just a little bit in some additional stress because we’re really tracking all of our expenses really tightly and we’re making sure that we don’t spend foolishly.
- No silver bullet for stress, but certainly meditation, exercise, and being aware that you are stressed.
- Even though there is this sort of stress and there’s sort of some existential risks to this experiment that we’re running, it also feels aligned with where we want to go as a family and as an exit plan from work life at some point.
Links from the show
- Default Alive
- Equity Financing vs. Debt Financing: What’s the difference?
- Gather | Website
- Brian Elliott | Twitter
Thanks for listening to another episode of TinySeed Tales. If you haven’t already, be sure to check out Season 1 of TinySeed Tales where we follow the Saas journey with Craig Hewitt of Castos.