Episode 567 | From Developer to CTO to Buying the Company for $1

Rob: Welcome back to Startups For the Rest of Us. I’m Rob Walling. If you read the title of today’s episode and thought that I was getting a little clickbaity, I wasn’t. Today’s literally the story of a developer who got a job at a company. He became CTO over the course of six months and then he bought the company for $1. Later he sold it in 2019. Stick around to hear how he managed to pull that off. It’s a great conversation with Don Pottinger.

The day after this episode airs, I’ll be hosting MicroConf Local in Portland, Oregon. If you’re in the area, I’d love to see you there. Then next week, we’re in Boston, then Austin, Texas, and the week after in Dubrovnik, Croatia. If you’re coming to any of these events, please do come up and say hi. I’d love to meet you.

If you don’t have tickets yet, I believe there are still a few remaining. You can head to microconf.com and click on our events section to figure out how to buy tickets. Again, the MicroConf Locals are one-day events and they’re quite inexpensive. It makes the events really accessible. If you’re in the area, I hope to see you there. With that, let’s dive into my conversation.

Don Pottinger, thanks so much for joining me on the show today.

Don: Thanks for having me, Rob. It’s a great honor.

Rob: You have such a story. Oh, my gosh. Started as a developer, then you became director of engineering, and then the CTO within six months. This is a company you came to work for as an employee, then you later bought the company for $1, and then you grew it and exited a few years later. I don’t think I’ve ever heard a story like this. It’s going to be fun.

Could you give listeners a little bit of background about how you came to work at Kevy? Maybe what attracted you to that. Just get us started on the story because it kind of tells itself from there.

Don: Before I joined Kevy, I was an aspiring developer and aspiring entrepreneur. I had started a company with my younger brother. We both used that as a catalyst for us to learn how to code. He delved into mobile and I went headfirst into web learning Ruby, Rails, and JavaScript. At a certain point, I realized that our growth was stunted because we were self-taught.

I ended up joining a company called Big Nerd Ranch who built apps for clients—both big and small. I was able to learn on the job how to build products. I spent about a couple of years there. I learned a lot through the process. Then I felt like I was ready to make the leap into the startup world, but I wasn’t quite sure how to do it. I wanted to learn from who I considered one of the best in Atlanta at the time.

I interviewed and joined Kevy which was founded by one of the co-founders of Pardot, which was a marketing automation platform that they sold for close to $100 million. When I joined Kevy, my idea was to learn to code, and then eventually hopefully start a company under that same portfolio of companies that Kevy was under. But it went completely different from what I expected.

Rob: Yeah, it’s a good story too. I want to touch on one point that you just made, which was you were self-taught and you wanted to get better, so you got a day job coding 40+ hours a week. I did the exact same thing. I learned to code as a kid on my Apple IIe, BASIC. There was no web at the time. I’m that old, but I graduated from college with a computer engineering degree in electrical engineering and still didn’t know how to code for the web.

It was the late ‘90s and they weren’t teaching that because the academy tends to be (depending on the school) 5, 10, or 15 years behind the actual industry. I graduated and I was an electrician. I was working in construction and I would go to the library and check out books on Perl, PHP, and HTML because I was like, the web is the future, dot-com is happening. I lived in the Bay Area.

I was trying to teach myself. I was doing it nights and weekends, and I just was not making progress. The moment that changed was when I finally applied for a full time job. The same thing, I worked for an agency. We were building websites and web apps. In the first two months, I learned more than I had learned in a year of self-study.

Don: For me, that was a very similar experience. I went to Georgia Tech. I studied electrical and computer engineering there. My favorite classes were the programming classes, but it was C, C++.

Rob: Java, if you’re lucky.

Don: Yeah, Java. There weren’t things that at the time, you could easily take and build for the web. So I initially started with PHP on my own, basically taking what little code I could find on the internet and doing a hatchet job on it to make it do what I wanted it to do. But it wasn’t until I came across Rails and Michael Hartl’s Ruby on Rails course, which I’m sure many people have taken, where I built a Twitter clone.

I had no idea what I was doing at the time, but I learned a lot just by typing in the commands. Eventually, when I started building my own things, going back to that tutorial, and seeing how they recommended to do certain things. Of course, RailsCasts during that period as well were big. That really helped me get in the door at my job because I joined a company that was a Ruby boutique firm.

They were looking for junior developers. They really wanted to learn. I was able to surround myself with very talented and senior engineers that taught me how to take what I’ve been doing on nights and weekends and turn it into—I considered myself a craftsperson at the time.

Rob: That’s a great part of the story (I think) just what the web has done for learning technical skills. Because again, I graduated in 1998 from college and there was one website that had tutorials on how to program. You just couldn’t find them. So when I say I went to the library, no, I literally drove my car. I got a dead tree book. It’s so cool that you had podcasts and videocasts. You can learn incredible amounts. I think it’s done wonders for development and entrepreneurship.

Don: If you’re lucky, you have a mentor. I was lucky that I had a mentor that had been building a company. He told me, hey, stop what you’re doing, go learn Ruby on Rails and see where that takes you from there. To this day, I credit that person for starting me on a journey that I never would have imagined over 10 years ago now.

Rob: So you applied and you got a job at Kevy in December of 2014. At the time, Kevy was competing with Zapier, is that right?

Don: Yeah. These were early days. Zapier and Kevy were competitors in, what I would consider, sending data from point A to point B. I think where Kevy was focused is that they had a lot of ecommerce companies that were trying to send data from their ecommerce platform to a CRM or to their marketing automation platform. At the time, they were getting customers, but they were also losing customers. They were really concerned about the churn. I think after I joined in late 2014, they decided in early 2015 that they wanted to pivot.

Rob: Got it. How big was the team at that time?

Don: The team grew to about (I would say) 20 or 25 at that time.

Rob: And when you joined?

Don: When I joined, it was about that big and we hired several salespeople after me.

Rob: They kind of connected the Zapier approach isn’t working because churn’s too high. Talk me through the pivot, I know that was early 2015. Is the pivot what led you to go from software engineer to director of engineering to CTO within six months?

Don: Yeah. I guess if there’s one thing about startups is that things change very quickly. In this case, the pivot led to the departure of the most senior engineer at Kevy. There were a few other engineers. I was one of them. At the time, I felt very confident that I could build a Greenfield project. I could take something and start from scratch, design it, and build it.

With that opportunity of the pivot where we had to build an entirely new platform, and in this case, we were focused on the ecommerce companies that were our customers, building a platform that allowed them to market directly to their customers in one place. I felt confident that I could do that. With that, I became the director of engineering. I was doing that for a few months before there was a leadership shakeup, and I became the CTO about a few months after that.

Rob: How did that feel as someone who—I mean, you’ve been coding for a couple of years at that time professionally? That feels like a big responsibility to be a CTO to a startup earlier in your career.

Don: Yeah, it was. I made a pivot myself into software development. Coming out of college, I was a consultant. I worked at Accenture and another mid-size consulting firm for a few years. Development wasn’t the first thing I did. I was comfortable talking to teammates, potential customers. I felt like I could do sales. I felt like I was at a point where I had been building on my skills to be multifaceted in a way that really benefits you as an entrepreneur.

It felt really quick. It felt really fast, but I also felt like this is exactly why I joined Kevy in the first place was to get an opportunity to lead a company. Was I ready? Yes and no. I learned a lot through the process. It’s not great when you have to let go of teammates, or when you’re trying to sell or you’re losing new customers, and going through all that pain and trying to raise money. But it really was an experience that I wouldn’t trade for anything in the world.

Rob: The beauty and the curse of startups is that things change so quickly. There’s that upward mobility or just the mobility within an org that can happen. Obviously, those circumstances where it was not good, sometimes it’s layoffs or whatever. But if you go work for a Fortune 1000 company, the odds of you moving from a software engineer to a director to some C-level is never going to happen.

I understand that it’s different to be a C-level at Target or Best Buy than it is at Kevy when it shrinks down. There is a difference. I’m not trying to equate them. But I do recall also working at a small consulting firm that is a small startup myself and feeling like I was given all these amazing tasks instead of being a little cog in a wheel. That I was actually given a lot more responsibility to just go do it because there were five of us or whatever. Then with Kevy, with the product pivot, was there also a round of layoffs? Did it go from 20, 25 down or did you keep everybody, all the employees?

Don: We had two rounds of layoffs, unfortunately. Once we pivoted, we realized we didn’t need a large sales team because there was no product to sell. We kept a very small sales team. We’re building very quickly trying to get something that the remaining sales team could put in front of customers’ demo and get feedback and hopefully sign some deals. But it came to the point where we realized we still needed a little bit more time.

Probably the best salespeople for our product were going to be us, me as the CTO, and my co-founder the CEO as well. Once we had to make that tough decision, it was really hard to let go of teammates and people that you’ve really grown close to. That was a really hard lesson, that not everything is rosy in a startup.

Rob: Was that one of the hardest pieces for you, the interpersonal? I’m just having to let people go who you knew were doing a good job, but it was just crazy startup circumstances.

Don: Yeah. That was a really hard part. I’m grateful that I’ve maintained relationships with the vast majority of them after that experience, and also the interpersonal relationships of the people that stayed. No one really talks about how challenging that could be sometimes. There can be friction sometimes between engineering and sales where sales are wondering, can we sell something like this, and engineering is like, wait a minute, we haven’t built that yet or it’s going to take time to build that.

That friction existed, also trying to keep the people that you did have from looking at other opportunities because, in a startup, it’s hard to see the forest from the trees when your head’s down working. There can be turnover. We were working in a startup incubation space. There are other startups that are vying for really good talent as well. It’s always easy to look and say, oh, it might be better over there at the other company. That seems to be growing very quickly.

Rob: Yeah. When layoffs happen, recruiters start targeting companies for the people who are remaining. It’s a pretty common practice. It sounds like that was brutal. It wasn’t even a pivot. You literally threw out the codebase and you started essentially from scratch and built a different product, which is I think you already set up a marketing automation platform focused on ecommerce. You and I are both pretty familiar with that.

For folks who haven’t followed my story for a long time, I built Drip, which started as an email service provider. Eventually, it became a marketing automation provider, lightweight marketing automation. When I was running it, it was general-purpose really. It was SaaS, bloggers, and people with email lists. We put a lot of people from MailChimp and then Infusionsoft, and then sold the company in 2016 to Leadpages.

It wasn’t even a pivot. It was focused on ecommerce companies as well. Now competing with the likes of Klaviyo and MailChimp, as you said. MailChimp has really done just a slight focus on that. You mentioned offline that the founder moved essentially to a role as an investor advisor and then a new CEO came in. Did it happen at this point as well, the pivot? It was a massive shake-up. It was like a new company with just a handful of people. You were down to like five employees or something, right?

Don: Yeah. The new CEO was someone at the company that had been promoted into the CEO role. She was a young CEO. I was a young CTO. We were both learning on the fly. Although (I would say) we’re very ambitious and had delusions of grandeur in some respects, we were heads down both working very hard because we thought at the time, this is it, this is our opportunity.

We don’t want to let our team down. We don’t want to let our investors down. We were working nonstop. At that point, I was working—I can’t even remember how many hours, but anytime I was in front of a computer, I was probably coding. I have a family. I have one child at that point. I had two more on the way—twin girls on the way, at the time. It was a very busy period.

Rob: I assume that MRR went to zero or approximately. You must have had enough funding in the bank to float you guys for a year or more. Because I think you said you spent the next 18 months building the product, finding customers, and growing MRR again.

Don: Yeah. If I remember clearly, we got a check of about $300,000 from the investor. It’s like…

Rob: Here’s your shot.

Don: Yeah. Honestly, if you think about it, it should have been reincorporated as a new company. The cap table should have been cleared, which we can talk about the cap table later. But it was essentially a new company with the same name.

Rob: Yeah, let’s talk about the cap table because this winds up screwing you guys. You start making progress, you spend the next 18 months, you get to $250,000 ARR. You build this thing back up to $20,000 a month. You want to go raise funding and you can’t. What happened there?

Don: We would walk into investor meetings and they would be very interested in what we’re doing, the space. We get it to due diligence, and they take a look at the cap table and see that the original founder—along with several other people that were brought onto the company that had left had big chunks of the company—while the CEO and CTO (me) had a very small amount of the company. That raised a lot of questions. That caused a lot of trepidation with investors.

Especially where we were in Atlanta, they were less inclined to take a chance on a very messy cap table. We would go in and feel very optimistic. A couple of weeks later, there were crickets or it was a no because of the complexities with our cap table, not necessarily what our product was able to do, the customers, and the revenue that we’ve hit.

That was very challenging and also disheartening because it had gotten to the point where like, we’re not sure what to do. Do we go back to our original investor, ask for more funds, and get further diluted, or what? That led to another big shake-up in the company and around the Fall of 2016.

Rob: Before we get to that, I want to call out, we have had multiple companies apply to TinySeed. We get in conversations with them and we make them an offer or we want to make them an offer, but we discover that the founder or founders own a minority share of their own company. Usually, in the cases we’ve seen, they started the company and there was an investor there who put in a small amount of money. Usually, it’s sad. It’s $25,000 or $50,000 and takes 50, 60—just takes way too much of the company.

When there’s nothing there, you can see how that makes logical sense, but it keeps you from ever raising money again. You can never raise money because investors don’t want someone sitting there with the lion’s share of the equity. They want the people doing the work to have that. This is not to say, never raise investment. It’s to say, be careful about your cap table.

The founders, at an early stage company like this raising really a first or second round, pre-seed and accelerator round, a seed round, the founders should own 80%, 90% of the company, between there. If it’s one, three, five, or whatever, they should own that together. It’s something to keep in mind for folks. Especially listeners of this podcast, if you’re a bootstrapper, you’ve never had to think about cap tables because you just always had 100% of it.

The moment that if you do think about raising a small round, be really aware that most—my rule of thumb and I think the general rule of thumb is, in an investment round, you usually sell between 10% and 20% of your company depending on the amount you decide on evaluation. And then you take 10% of that or (again) 20%. It’s pretty rare. I hear someone selling, unless they’re selling their own shares on a secondary, it’s rare someone sells more than 20%. I see you smiling. Do you have more stories?

Don: No. The experience that I went through with Kevy really left a bad taste in my mouth for raising money. I went firmly into, I am going to fully bootstrap everything I do for the rest of my life for a period of time. Only now, the past couple of years to come out of that and feel like it depends. It really depends on who you are, what your goals are.

In my case with Kevy, I didn’t really stand a chance because I owned so little of the company at the time. I just know that being careful and understanding who you’re bringing on as an investor is equally as important as if you decide not to and you want to just continually have a stable business as a bootstrapper.

Rob: You’ve mentioned there was a shake-up in 2016 because you weren’t able to raise funds. What happened there?

Don: Yeah, my CEO just left. To be honest, she had been talking about it for a little while. So it wasn’t a surprise for me, but it was a surprise to our investor. I think it shocked him to the core because he felt like we were on a positive track. He didn’t see that there were any issues outside of continuing to figure out what product-market fit, being heads down on selling, and also raising money.

However, with the departure of the CEO, it left him in a crisis in terms of what to do with the company. That company had been his baby post his acquisition. But I think at that point he was ready to close up shop, let go of the entire team. Before he did that, he asked me what I wanted to do with the company. Did I want to take over the reins? I had to give it some thought, but I think I realized that I would be in a similar situation to the CEO who just left.

I proposed something completely different. I proposed that I would buy the company, the assets from him if he was going to shut it down or if he didn’t want to find a new CEO. He gave it some thought. He agreed to sell it to me for basically nothing—$1, which was just crazy.

Rob: Did this happen in real time? Were you sitting in a room looking at each other with the conversation, or was it back and forth via email that happened over several days?

Don: It was in real time. You can imagine a scene out of a movie. If it was dramatized, that’s how it felt in my mind. We were sitting across from each other. I was really trying to fight for the life of the company.

I’d said please don’t shut it down, you can find a new CEO. He wasn’t convinced. I was like, well, I want to continue working on it. I think I phrased it in a way that looking back now, I don’t know if it came off the right way. I want to do it without you and he did some kind of back of the napkin calculation in his mind of in terms of the company’s growth, what were the expenses, and trying to (I guess) decide what a good asking price would be for the company.

I think he just came to the conclusion that, hey, this is really nothing to me more than a line item in his portfolio. For me, it was life-changing. It all happened in one conversation. After that, we got the paperwork. I took $1, put it in an envelope, walked over to his desk one day, and dropped it off just to make sure that he did receive the dollar for the company.

Rob: The I’s were dotted. It’s like a scene out of an Aaron Sorkin film, man. That’s crazy. Here’s the other thing too. As an investor, he invested in a lot of companies.

Don: Yeah, he did.

Rob: He also probably (for sure) has capital gains that he could then write that off so he could get at least 30% to 40% of it back from the IRS. I’m not saying that’s a good or a bad motivation, but that is why you’ll hear some VCs write off. If you’re familiar with Baremetrics, Stripe Capital or whatever venture arm they had, they just wrote that investment off to nothing. They don’t get it all back, but you basically don’t pay the taxes on equivalent gains. It’s like having a loss in the stock market and again that offsets it.

That makes sense if you got something out of it. I imagine if he’s trying to think he’s like, how much am I going to sell this company to you for? Are you going to take out a loan to buy it? I don’t know if you’re in a cash position to be able to pay $50,000 or $100,000.

Don: I was not. I was looking for jobs at that point. It was something that I had pretty much decided I was willing to walk away from. But when the opportunity came, I decided to take it and it changed the course of my career.

Rob: Absolutely, the course of your life. What a gutsy move to say, I want to do this, but without you. Was that scary? That scares me because I’m not super confrontational and that feels like a very confrontational thing to say.

Don: I’m not confrontational at all. I work very well with others because there’s usually not anything for me to fight about. In this case, I think I felt strongly enough about the company and more so confident in my own abilities because I built it. Almost every line of code that was there was written by me, reviewed by me, or touched by me. I’d been in plenty of sales conversations. I knew how to support the customers.

Because of the revenue that we had, I felt comfortable. It felt like the most comfortable risk I could take at that point because I dreamed of running my own company myself. I de-risked a lot of that for the past 18 months by building it and having someone fund that discovery. It felt almost like a no-brainer to at least give it a shot.

Rob: It was your company in essence. I think you were calling her your co-founder, the CEO, you guys had started a new company that should have had a new cap table to the point you made earlier. I can imagine you had massive ownership over this, mental ownership of it just like, yeah, this is the thing and I can grow it. I hate it when people use the word, it’s my baby. You had spent a lot of time working on it.

Don: You can imagine too, when you go from being an employee to (on paper) being CEO and getting an agreement that says, hey, you have X amount of shares and trying to do the math on what percentage of the company that is, and then realizing that it’s 5%. You’re like, well, I’m putting all of my blood, sweat, and tears for something that I own 5% of. Using terminology like I’m a co-founder was very difficult for me. I had to have people support me and say, yes, you are a co-founder.

A lot of people don’t understand—especially when you’re young and you’re being employed—the courage and the agency it takes to be able to say, yes, you may have funded this company, but I’m building it. So I deserve to be a co-founder, I deserve to own a large enough share of the company. It took me a long time to realize that. I grew into that after the acquisition, realizing that, hey, this is my company too.

Rob: At this point, you own 100% of it. You had revenue at this point, but were you breakeven? Did you need to raise money? You told me offline that you started doing everything yourself— sales, marketing, support, development. Did you have any other team members or were you solo at this point?

Don: At this point, I was solo.

Rob: Wow.

Don: My initial idea was that I was going to just continue growing the company like we were growing previously. I ran into a wall, I ran into, oh, keeping customers is difficult. Acquiring new customers is difficult when you’re all by yourself, and developing the product simultaneously all at the same time was very difficult. I tried to continue working very hard for the first six months after the acquisition and then I hit a wall where I felt burnt out. I had to take a step back and really evaluate, why am I doing this? I have 100% of this company.

Am I trying to make it the next billion-dollar company? If that’s the case, I can’t do it by myself. Am I trying to have a high quality of life? Am I trying to be able to spend as much time as I can with my family, work from anywhere, and have the ultimate flexibility? Because the revenue was more than enough for a solo founder. The expenses were low enough that I was riding on different credits from cloud providers, so I was able to keep expenses pretty low.

Rob: You have this amazing lifestyle business’s bootstrapper’s dream at this point, except for your burnout. That was a problem. When you took that step back, I know you mentioned that you’ve been a longtime listener of Startups For the Rest of Us. I want to take a moment to talk about virtual mentorship because you said that Mike and I were chatting together, and me talking about burnout and Drip or whatever it was I was talking about somehow helped you on your journey.

Don: Rob, it was cathartic. After spending the entire day working on Kevy, I would fire up the podcast and listen to you and Mike. Mike’s journey with Bluetick felt like I was in therapy with Mike and you, and your journey with Drip and post-acquisition. I was just listening to every single detail, listening to the intonation in your voice trying to read what you couldn’t say sometimes from that. It was inspiring.

It also felt like I wasn’t alone, which as a solo founder if you’re not really into online communities, it can be challenging. Luckily, I had a support system that was local and then also podcasts that I would listen to like Startups For the Rest of Us. That really helped carry me through.

Rob: That’s great to hear. You’ve heard me say it like, we’ve done the podcast for almost 12 years now for free. That’s one of the big reasons we do it is because we wanted to find others like us and we just want to be able to—it’s not even giving back, it’s just helping other people. The amount of good I think that is put into the world is substantial. It’s so good to hear because you and I, before today, have never met.

We haven’t even barely emailed just to schedule this, and yet I was able to have that impact on you. I hope that those who are listening, we can do that in our own ways. It’s awesome, man. It’s great to hear.

Let’s get back to the story. Now you own the company, you burn out, but then you recover. Where do you go from here? Because in 2019 then, which was a couple of years later (two or three years later) you wind up selling the company. What’s the summary of that in between? Was it more of the same but were you lifestyling? Did you start hiring people? When you sold, were you solo? What are the details there?

Don: It’s a mix of, I was lifestyling almost to a fault in some ways. I think things have grown stagnant. I gravitated toward what was interesting for me to work on like products—I love building. I would let things like marketing, I’ll get to that eventually. When inbound sales would come in, I would do demos, I would follow up, close the deals, and things like that. I brought on different people at different points.

I brought on my salesperson that was working on doing demos, cold outreach, and things like that. It didn’t really work out that well. Then around the tail end, probably about a year before I sold the company, a friend of mine who’s a data scientist was working on a startup. He said, well, you’re a data scientist. I’m sitting on a lot of data right now with Kevy—ecommerce behavioral data. Maybe we can build something of value for the Kevy customers using your artificial intelligence machine learning knowledge.

We started collaborating. We started building new, exciting what we called smart features for Kevy. Things like being able to tell you how effective your email will be based on the subject line. Eventually, the plan was to give you the ability to write your entire email without having to do it yourself based on your previous emails, based on emails that have been effective in the past.

We were building and building and building that. Then I think in December of 2018, my wife shared that she’s pregnant and it’s our fourth child. Up until that point, my wife had been working enough as a nurse practitioner. She’d been working enough to provide health insurance for us so that we didn’t have to worry about (at least that part) me being an entrepreneur. It got to the point where she’s like, well, I think we need to make a change because I don’t want to work full-time anymore. I said, okay. Well, I can at least put out some fillers and see what’s out there.

A friend from Google reached out to me, and I ended up getting a job at Google and running Kevy at the same time. That was in April of 2019. There was a period of time where I decided I wanted to sell Kevy, but I was working out at Google. I got a broker and I was talking to potential acquirers. Some were serious about acquiring, but they wanted me to join as well. I had to share with them that I wasn’t on the table as part of the acquisition.

Then eventually, I found a venture studio that had a SaaS product in a similar space. They were really interested in acquiring it. They had the technical chops to be able to take over the project. They had aspirations for their sales and marketing as well. After due diligence, I ended up closing the deal. I literally signed the papers to sell Kevy in the hospital after my wife gave birth. It was a crazy period there.

Rob: Sounds insane, man. I was going to say good timing, but probably terrible timing because I imagine that was stressful coming up. The question that I usually ask here is, there’s life-changing money, which to some people oftentimes that’s a few $100,000. Then there’s, never having to work again money, sunset money, which is usually for most people (depending on where you live) at several million dollars. There are in-betweens. How would you describe your exit?

Don: It was life-changing. It’s not never have to work again. But for me letting go was hard because (like you said) it was my baby. I would work on it for the next several years. It may not go anywhere, it may not grow. In some respects, the competition (at the time) like Klaviyo, MailChimp, and other companies had exploded in growth. They had deep pockets. They’ve been working extremely hard on developing and improving their product.

I didn’t have that in me as a solo founder. It was very difficult. It was great timing, and it was also a life-changing amount of money that I earned by signing a piece of paper. It was a life-changing experience to own and run Kevy, but I think it was great to close that chapter so that I can begin a new chapter with new projects and new endeavors.

Rob: And with a new child who is a new project. Four kids, that’s another level, man. You’re a glutton for punishment like most of us. As we move towards wrapping up, I am intrigued because you’ve launched another startup, but it’s a B2C play. It’s called LanguaTalk at languatalk.com. You mentioned to me before I hit the record that it grew very quickly. You launched in January, maybe eight or nine months ago, and you’re already at mid-six-figure ARR with it. What’s the difference there?

Don: There are so many differences. One, I have a committed co-founder who has grown and built a company in this space before. During some of my lonely periods, I would roam Indie Hackers and look at posts. My co-founder, before he was my co-founder, had a post of, hey, I have a business. It pretty much runs itself, so if any other indie hackers who want some help on some marketing, just reach out. I was like, all right, sure, I’ll reach out.

I reached out. He did some work for Kevy and we stayed connected for the next couple of years. After I sold Kevy and I was bored at the day job, just dreaming about what to build next, we reconnected and I said, you know that platform that you’ve built? You’re a great marketer, you know the space very well, but I think I can help you build something that we could grow to even higher heights.

He thought about it and he’s like, are you serious? Shouldn’t you be comfortable and done? Do you have the capacity and the time to do this? I was like, no, I don’t, but I’ll do it. Let’s do it. We started building last year. It took me longer than I expected. I didn’t expect my building skills to atrophy as much, but we launched in January. Because my co-founder had been in the space before, he knew all of the knobs, the marketing, the timing, the ads, and me from the technology side, we had everything buttoned up.

It’s been really amazing to go from literally $0 in revenue to mid-six figures in ARR. It’s really exciting because it’s very early days and we’ve only launched probably about five languages. We’re planning on launching several more in the coming weeks.

Rob: Good for you guys. You don’t know if it’s being a second-time entrepreneur because that’s got to have something to do with it, all the years of struggle. It’s like the Beatles in the Cavern Club for 4 years playing 10-hour sets and stuff. No wonder they got good. You went through a gauntlet, you came out the other side, you sold your company, and now you’re doing it the second time.

I do find that I can get what used to be a day’s work for me—eight hours a day—I can often get that done in one or two now. I’m more efficient, I’m more effective, I’m better at delegating. I’m just more everything. I feel like that happens with a lot of us. Smart folks like yourself are learning.

Don: It does, and I know when to walk away. I think when I was early on in my career, I would sit there in front of the computer banging my head across like, why can’t I fix this bug or why can’t I solve this problem? Now I know that if I walk away, I go to sleep, you can solve things with a fresher mind or you solve things in your sleep as well. You learn through the pain and that muscle memory is still there iIf you decide to go back to it.

Also, I think going with the tide is important. Building a platform that helps people learn languages over tools like Zoom in the midst of a pandemic, I think that timing is important as well. You have to do the work, but I think you also have to pick the right space and also have the right timing too.

Rob: Do you have a website or Twitter that you’d like me to plug?

Don: Of course if you’re interested in learning a language, languatalk.com. My Twitter is @donpottinger, first name and last name.

Rob: Awesome, sir. Thanks so much for coming on the show. Thanks again to Don for coming on the show. Thank you for being a loyal listener and coming back every week. If you’re not already subscribed, please do hit that subscribe button. If you haven’t checked out the MicroConf YouTube channel, that’s something we continue to invest in.

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