How Three Serial Entrepreneurs Went From Side Project to Scale to Sale

How Three Serial Entrepreneurs Went From Side Project to Scale to Sale

It’s a good time to be a bootstrapped SaaS Founder, and it’s not unusual to meet serial entrepreneurs in my line of work — one of the main reasons bootstrapped Founders sell to SureSwift is because they have another project they want to work on. It is pretty unusual to meet a group of three bootstrapped Co-Founders, though.

Mike Machado, Brett Owens, and Carson Gross are the founding team behind LeadDyno, and they leveraged their diverse set of talents over the course of nearly a decade to build this powerhouse of a product in the affiliate marketing space.

I got to chat with the trio recently about the story behind building LeadDyno, all the way up through their decision to sell the business.

An interview with LeadDyno Founders, Mike Machado, Carson Gross, and Brett Owens

Tell us a bit about your background. How did you all meet, and how did LeadDyno become a business?

Brett and Carson were actually working together on a different project when I first met them. And I was working on my own startup along with Matt, who works for SureSwift now. We all got to know each other around the local entrepreneurial circles in Sacramento. As we got to know each other better, the opportunity came up to start a new project.

It was something that Carson and Brett wanted to build, but rather than build it as an internal project Carson really championed the idea of starting it as a new entity. Matt and I were winding down our startup, so it was perfect timing.

Yeah, Brett and I wanted to build out software for a reseller/affiliate program and I said, “Hey, we might as well build this as an external system, and maybe we can sell it to other people, too — who knows.”

I also really wanted to work with Mike as an engineer because I thought he had a really good skill set and I like that collaborative aspect.

The idea of it being a three-person startup was definitely intriguing to me, too. Most of the startups I’d worked on before were just two people. So, the fact that Carson and I were both developers, and having that second engineering mind on the product at the very early stages was something that was really interesting to me. That was a big part of what made me want to take the leap to join them.

The full background is that a Co-Founder and I founded that original company, Chrometa , in 2008 and then maybe around 2011 we started having conversations about resellers, like Carson mentioned.

We were in the legal software industry. And the customers we were trying to tap into were solo and small firm attorneys. They were all not only running the same software they had been since the 90s, but they would also listen to this old-school reseller model.

Imagine a lawyer’s office in a shopping strip mall in Nebraska (or wherever), and there’s an IT person who will physically go into that office and tell them what software to run. We wanted that IT guy to tell them to run our software. We knew it wasn’t as simple as getting a website up to acquire subscribers — we really needed a boots on the ground approach.

So the question became, how do we do that? How do we get these established resellers who are making money selling their existing products to sell ours? How do we incentivize them? That’s when we knew we needed a reseller/affiliate program.

And then I guess fortunately for us we were all stubborn software guys. We could have just gone out and bought something, but Carson and I checked out the landscape and just didn’t find anything we cared for much, so we decided to build it ourselves.

How did the product evolve over time?

Well, initially Chrometa, and the startup I had that was going to be a customer of LeadDyno were really what drove the feature set. We had this initial vision that software and SaaS would be big for us, but when the rubber hit the road, we found there was a better market fit in the e-commerce world.

Well, I want to throw in here — I think you may have been early, not wrong, when it comes to affiliate marketing for software. I’ve had a couple conversations recently where people are sort of realizing that all the headaches that come with a traditional reseller relationship are no longer worth the hassle. So from my personal perspective, part of the excitement about LeadDyno is that I think affiliate marketing is continuing to become more and more mainstream as a marketing channel.

Yeah, for sure. We basically reacted to what was driving revenue immediately. For us, it was a no-brainer to at least build out the initial feature set for e-commerce, and then there was some more development to do in that space once we started getting that product-market fit signal. But absolutely — I definitely see that SaaS could be a big part of it going forward. That was always the vision.

What did that discovery phase look like? You built something for a certain type of customer that looked a lot like your own business. But then you wound up discovering maybe e-comm was the bigger market, and those customers had different needs. What was the point when you started noticing that, or what were you looking at to get those signals?

That discovery really came from working with marketplaces. One of the first marketplaces that we integrated with was Salesforce, because initially we were looking for marketplaces where SaaS people lived.

As part of that research on what marketplaces were out there, we came across Shopify, which was pretty new at the time. We looked at what we could build on their API. And since we were already doing integrations to other third-party platforms and marketplaces, we said, ‘Hey, why not?’

But that’s what really started to move the needle and Shopify started really eclipsing all of the signups from the other platforms. That really cemented the idea of e-commerce, but it also really cemented the idea of building for marketplaces. Then we started looking at BigCommerce and all the different e-commerce platforms that we integrate with now.

Do you think having three Co-Founders lent itself to being able to do that? Working across multiple APIs for all those integrations definitely adds some complexity.

For sure. Having that product-market fit signal was great for the company. And it really led me to focus on additional integrations, Brett took the lead on the relationship side of that, and Carson took on the hardcore algorithmic architecture of the affiliate compensation models.

So Brett would reach out to the new marketplaces that we were exploring. And then Carson, and I could focus on the technology and the actual implementation of it. It was a great multi-pronged approach. Carson and I could focus on the tech side, and Brett could focus on the relationships and the product side.

Was there a specific moment where you realized that you had built something that could be big? What were your early goals?

Personally, my first goal was just to finally work on one of my own startups full-time. I’d started a number of businesses over the years and I’d always let my business partners take the full-time role first. I’d also always maintained other contracts and income sources. So, I was really ready to just focus on one thing.

How long was it from launch to where you are all working full time on the product?

We all did it at different times. I was one of the earlier ones — for me, I think it was about two and a half, three years. So it took awhile to reach that goal.

And how about for you, Brett? Were your goals the same — to work on it full time?

Brett :
Focus was a definite thing, because I had two startups and I was bouncing between the two. On the LeadDyno side, my initial goal was to get to market as soon as we could. And we did a really good job there. I think sometimes startups spend too much time on the details. We got the LLC going in December 2012. And we had something out to market around mid-2013, with a few paying customers.

An interview with bootstrapped founders of LeadDyno

Customers don’t know how new you are, or how many other people are using the tool. But we literally still had watermarks on the stock photos on our website, and I think one of our earliest customers sniffed that out. There’s just a huge value in getting there and getting established and being a part of the market, though. Once you’re there, then everything else makes a lot more sense for the product decisions that you’re trying to make.

So, for me that was the first big thing — just get to market.

Then it became — can we get some better economics? We knew there were established competitors in the space charging up in the multi $100 range for plans. In the early days we used traffic as a proxy for willingness to pay, and we felt like if we could get to a $70 or so average price point, everything would fall into place.

You just have to kind of feel your way through that stage. It was my second time through, so I knew I just needed to take it one step at a time and get the model established, then get the marketing working, then figure out what channels people were coming in through.

Well you definitely got established. By the time you sold to us this year, you had a team of eight that moved over to SureSwift. I was curious what hiring looked like for you over the years and what it took to build that team? And then on the flip side, how did that impact your decision to sell and your conversations around selling?

I wouldn’t say we should write any books on hiring. We built a really good team, but we kind of fell into it. I can’t say there was any rhyme or reason, and a lot of it was just the chaotic emergence of a good team.

The one thing I do think that we did a good job of is that all three of us felt that we were going to stay a Founder-only company, so we knew we were going to stick to a contractor model. But we still really wanted to treat people right and pay well. We wanted to keep equity with the Founders, though. We were just hesitant to make that move to where we would become a company that needed an HR department. There are good things and bad things about the model we used. You end up paying a little bit more for your team — at least in cash — but it did give us a lot more flexibility and it made the exit a lot cleaner.

For the first four to five years of the business, Carson was the CEO and I was the CTO, and we ended up switching roles some years back. So, for the early days I don’t have the perspective he had, but hiring has always been a challenge.

I can tell you that it’s always one of those things where you try to find that talent early on, and then you have to try to balance compensation with growth. But in terms of the acquisition, one of the challenges was trying to feel that we were making a good decision for the team and that they were all going to have the opportunity to continue on with the product. Knowing that was your goal certainly made it easier.

And did you ever consider raising money vs. selling? I was curious, because starting to scale a team is often a decision point, and you’d already done a good amount of work there.

We did look at raising a little bit in the early days, but not too seriously. And I know you always hear about success bias, but I just think bootstrapping makes a lot of sense. As a Founder it gives you the opportunity to grow and optimize the way you want to.

An interview with the bootstrapped founders of LeadDyno

Tell me about deciding to sell — what did that decision and conversation between the three of you look like?

I don’t want to speak for Brett and Carson, but I’m more of an early-stage guy. So going on seven or eight years into the business, I was starting to think about the next thing. And then I think we all had different ideas of where we wanted to take the company. Rather than trying to tug each other in any particular direction, the simpler solution was to sell. Those two things are what really drove the decision for me.

Yeah, I had similar sentiments and when Mike met Chris from your team and introduced us, it just seemed like a no brainer. That was the best-case scenario from my standpoint — being able to sell but get the company in good hands.

I had gone through the sale roadshow process a little bit with my first company, and back then I was playing the role Mike did this time around — taking the calls. Those calls ranged from people you’re comfortable selling to, to people you’re terrified of selling to where you can tell they’re just going to take as much cash flow as they can get, but the product and the team are going to be in trouble. So that was my main concern with selling this time as well.

I was probably the least motivated to sell since I really like the idea of a cash-flow based company, but I also understood that it’s just different when you hit a certain point where the technology is mature. It’s a different company at that point than it is at the earlier stages. And if the other Founders want to exit, it’s probably time.

I was very happy to find out that SureSwift had done this before, and no one else we talked to had the engineering infrastructure that you had.

So for me personally, it was a best-case scenario too for an acquisition by someone who isn’t just going to ride it into the ground and extract as much money as they can. They’re actually going to take it and try to grow it.

It sounds like you all got aligned before talking to us, which we always think is really important in a situation where there’s more than one Founder — the sale process just can’t run smoothly if you haven’t had those conversations.

Yeah, we had the luxury (if you can call it that) of going through a couple sale/acquisition attempts before this, but we were all fairly aligned on what we wanted so I think that that certainly made it a cleaner, easier process.

One process thing that surprised me that I think is worth mentioning is that Mike went through the MicroAcquire marketplace for the sale, and that just worked out so well. I’m a technical guy, and I just kind of expected that to not work, but I was pleasantly surprised by how well it did work, and it really provided a much higher-quality acquirer.

Yeah, I was initially concerned that maybe we were a little too big for a marketplace sale, but I actually reached out to Andrew Gazdecki (the Founder of MicroAcquire) directly to get his input. He was able to point us to other listings that were a similar size and who’d had success, so that’s what convinced us to go forward with it, and I’m glad we did.

Carson, I know the most about what you’ve been up to since you’ve been working with us briefly to roll out your passion project, htmx, out to more of our products. But what about you, Brett and Mike? What’s next for each of you?

I’ve always been fascinated with finance and cryptocurrencies and blockchain stuff. So I’m doing a little bit of investing and playing in the crypto world, and then I also have some ideas for a new project around some of the new business structures that are starting to evolve out of the crypto world called the decentralized autonomous organization. It’s a new concept around business formation that really fascinates me, so I’m going to spend the next six months or so exploring possible projects in that space.

I actually already have another project going in an adjacent space — it was something we had kicked around doing with LeadDyno for years — it’s an affiliate network where we connect merchants with affiliates in their space, and it’s called Afluencer.

With the new project, we’re building a stable of influencers, especially people in a specialized niche — for example, someone in the U.S. with 10,000 or more followers who has a skincare focus, their engagement rate is above 2%, and they’re on TikTok and YouTube.

E-commerce brands are all looking for ways to get out, be visible, and get more coverage right now — especially on social media. (We all know Google and Facebook are doing really well on their ads by their earnings, but it’s really expensive to run ads there.)

So we’ve got that built out both from a platform technology standpoint, but then also the influencer database. Right now we have an app in the Shopify store and a web app and we’re building up both sides, so it’s interesting. It’s different from the early days of LeadDyno because when you have a SaaS tool you can just sell the tool, and if you only have two customers they don’t know they’re the only two.

But if you have a network it’s really obvious if there’s nobody in it. So you try to balance both sides of the network and make sure everyone’s engaged and having someone to talk to. We also have a lot of LeadDyno links from brands in there too, so there is a little bit of that overlap, which is cool.

Want to hear more from these Founders?

How the founders of LeadDyno bootstrapped their SaaS from side project to scale to sale

Interested in selling your SaaS?

If you’re thinking about selling your SaaS we’d love to be on your radar and answer any questions you might have about valuations or our process. Get in touch.

This Data-Obsessed SaaS Founder Achieved His First Exit Just Two Years After Launching His Shopify App

This Data-Obsessed SaaS Founder Achieved His First Exit Just Two Years After Launching His Shopify App

Many of the Founders we buy SaaS products from are selling because they already have another business they want to work on, so in my line of work I meet a lot of serial entrepreneurs. While GrowthHero Founder Mike Janeczek says he doesn’t have the next idea yet, I’d bet good money on reading another exit story about him in the future.

Mike has a unique blend of development skills and business acumen. Rather than approaching a startup with the typical idea > build an MVP > find product/market fit, he flipped the approach and set out to look for product/market fit on the Shopify platform before writing a single-line of code.

Nothing in business is a sure bet, but building your MVP based on a big data set and thorough research will definitely improve your odds of success.

I had the pleasure of chatting with Mike recently to go back over his story of founding and growing GrowthHero, and to talk about why he ultimately decided to sell the business to SureSwift.

An interview with GrowthHero Founder, Mike Janeczek

It’s nice to get to chat with you again. Could you tell our readers about your background and the story of building GrowthHero?

For me, building GrowthHero wasn’t a typical startup story where you say “Hey, I have this idea, and I’m going to try to build it.” It was more going in reverse — I knew I wanted to start my own thing and it made sense to build my own Shopify app because I had some experience working on apps for that platform as a developer.

So I did a ton of research on Shopify app categories and what was popular, and then I’d dive into what competitors were doing and where I felt like there were gaps or a niche that I could fill. I kind of had a formula in my head for figuring out how big a market there might be for a category based on reviews and some rough metrics like that.

Eventually all of that research led me to affiliate marketing, and I just thought there was an opportunity to fill that need and build something really great around it. That “something” turned into GrowthHero.

What attracted you to building GrowthHero on the Shopify platform vs. another eCommerce system, or just building a platform agnostic affiliate marketing app?

I had ​​learned about Shopify, their API, and their customers from previous work. In terms of eCommerce, I just think their app marketplace is valued higher than others. I’ve seen apps come out for a platform like WooCommerce with a $40 price tag, and people just don’t want to pay for it — they want it for free.

But in the Shopify ecosystem it’s very standard to add apps and add-ons to your store that you pay for monthly. If the app does something specific that people need, and it makes more money for their store, they value it and they’ll pay for it.

I think for people who can’t — or don’t want to — do their own development, Shopify’s a great system because there are a lot of solid developers building apps for it, and Shopify’s been very supportive of those app developers because they know it adds value to their platform. It’s really a win for everyone.

I love that research and data-driven approach to building a company. You’re right — so many people start a business and then go out and look for a market — and you looked for the market and then built the business.

One thing I remember hearing from Chris, our VP of Acquisitions, was that he asked how you track churn — which is not easy in Shopify — and you pulled this very methodical, systematic view of all the data.

So clearly with all this research and data tracking you wanted to start a business that would bring in revenue. But did you have a specific goal in mind when you started the app? When did you realize it could turn into something big?

Well even after all that research, I knew that a big percentage of startups that are built are dead before they even get started. So my first goal was just not to do that. I didn’t want to spend half a year developing something and then find out nobody wants to use it. I wanted to build pretty quickly, and get some traffic and some real users to make sure I was building a product they wanted.

GrowthHero Founder, Mike Janeczek shares his story of growing and selling his Shopify app in two years

I think that’s something I really want to share with other developers out there, because so many programmers are so focused on the code and improving the code. And yeah, that’s fun. But if you want to build a business, you really want to get those first 10 customers who are paying 20 bucks or something for your product. Because even if you’re just making $200 a month, you have a real business and real people’s feedback to help you build it and improve it. You’re not just sitting around refactoring code no one is using.

GrowthHero Founder, Mike Janeczek shares his story of growing and selling his Shopify app in just two years

So my early expectation for growth was just to build something that actually made some decent profit. And then it was, “Hey, now this can pay for my flat.” And then it was like, “Now maybe I can quit my job.” And then it was like “Maybe I can make more with this than I ever did with my job.”

You’re a bit of an outlier for a bootstrapped founder when it comes to your pricing plans, I think you’re actually the first bootstrapped Founder I’ve seen with a double-digit starting plan — your plans started at $39.99. Tell me about your pricing strategy and how it evolved? Was it hard to set a value and was that a process you stressed over at all?

When I launched, I honestly just looked at what other apps were out there for affiliate marketing and made sure I was competitive or at least in line with those. That’s the reality when you launch a new business — if there’s competition, you’re going to look at them and do something pretty similar for pricing.

As time went on though, I was doing everything on my own and I found that the number of leads coming in were driving more technical support requests than I really had time to manage.

And on Shopify lead quality can be all over the place. You can get a request for a ton of support and customization for a no- or low-revenue store that may only be around for a few months, and then you have these big brands doing hundreds of thousands in revenue who are going to be around for a long time.

Of course you want to provide great service to everyone, but it just doesn’t make sense to put a ton of time into a customer who’ll never convert to paid, or who’ll churn after one month.

So at a certain point I just decided that adding $10 to each pricing plan would lower the number of leads and technical requests I was handling to what I could manage and I’d be able to keep my revenue per install metrics steady.

Customer reviews are so important — especially on Shopify. Was your app rating or your number of reviews something you were focused on, or did that happen pretty organically?

I didn’t have any magic way of generating reviews. On Shopify I’d just noticed that something like 90% of the reviews on apps happen after someone gets help from support, so I focused on doing a good job on those early support requests.

The other things I’d say about reviews are that they’re a great place to research your competitors and it’s worth tagging or categorizing all of your own feedback and reviews to help develop your product roadmap.

On the competitor front, I checked 1-star reviews for everything in GrowthHero’s category, and you can really get some insight from those on what not to do or what to improve in your own app.

For GrowthHero, any time I got feedback I’d log it and tag it on a Trello board so if I had time to build a new feature, I could go check how many customers had mentioned it. So I had a high level of detail on why customers had uninstalled — like I would know that seven people had uninstalled because there was no multi-level marketing feature — so when we built that I could contact them and say “hey, this is now available.”

I think that’s especially important in the early stages when you have a pretty basic MVP and you’re figuring out how to improve the product and make it more competitive.

So is that how you built your whole product roadmap?

That was a part of it, but being totally honest, sometimes consumers want something that they don’t actually need, or they think they want something but they really need something else.

So again, there’s no magic way of doing it. But it does help to know the things that a lot of people want, and if it’s easy to build, you can just ship it.

Something else I think it’s worth mentioning specifically for other Shopify developers is that the customers on that platform love to have features around their brand, like changing the colors and adding their own logo. So if you’re working on the Shopify platform, that’s definitely something to consider adding to your app/roadmap.

Talk to me about hiring. You had a couple of part-time team members who joined the SureSwift team. When did you know it was time to make your first hire, and what was your hiring process like?

Yeah, once we grew I figured since I’m a developer, my time was best spent on development. So I made an investment and hired a couple students who were studying IT to work on the support team.

They were both remote and a support role is a great remote job, because as long as someone can respond within your response time goals they can have a really flexible schedule and work from anywhere.

Their IT focus in their studies was also great for all of us. For me, it meant they understood enough about some of the technical requests, and for them it meant they got to learn some basic HTML styling and javascript and gain experience.

So basically when I hired them I started breaking things down into two categories of tickets. If something was really critical or really technical, I worked on it. All the basic onboarding and styling stuff I had them handle.

Tell me about selling the business. I think we actually reached out to you first. Did you know anything about SureSwift, or had you ever thought about selling before we contacted you? What was your first thought when we reached out?

Yeah, Chris reached out, and I actually didn’t respond at first. I was following this guide called “23 rules to run a software startup with minimum hassle.” And one of the steps basically said “no acquisitions talks — if you’re growing, you’re good.”

But I wound up changing my mind on that part, because as a solo entrepreneur, and someone with a background as a developer, all the stuff related to being a CEO — managing people, hiring people — that was something I just didn’t enjoy doing and I realized I didn’t want to do it.

So really my options were to keep it small enough that I could run it on my own and not do those things, or I could sell it to someone who has a team and wants to do those things to grow it.

Chris wound up reaching back out again a few months later and I decided to get back to him, and we just went from there.

Yeah, we hear that theme a lot, actually. I think there are a lot of people who hit that point where they realize the work that it’s going to take to keep growing their business is different than the work it took to build it, and they don’t actually like doing that type of work.

Yeah, and the truth is that by selling now I moved the risk of growing it to you. And that’s okay because you’re a bigger company, so that risk is smaller for you than it was for me as a solo Founder.

That’s totally true, and a great point. I know you’re probably focused on the transition and I’m guessing that’s taking up most of your mental space, but do you have any immediate plans for what’s next?

I have no idea right now to be totally honest! I’m researching my options, and thinking about what to do next and how to invest some of the money from the sale into something new with decent year-to-year profit — I’m not sure about another business yet though.

This Data-Obsessed SaaS Founder Achieved His First Exit Just Two Years After Launching His Shopify App

Weighing Opportunity: Bootstrapped Founder Sells Successful SaaS Side Hustle to Focus Full-Time on Second Startup

Weighing Opportunity: Bootstrapped Founder Sells Successful SaaS Side Hustle to Focus Full-Time on Second Startup

Ben Latz is a self-described finance nerd who fell for software. (I can relate: My first job was teaching high school Math, and I really love a good spreadsheet.)

He also caught the entrepreneurial bug early on, and the combination of those three passions — finance, software, and business — led him to starting Wingman with Piyush Puri shortly before they graduated from Carnegie Mellon in 2017.

In late 2018, he also teamed up with a friend from high school to work on The TIE, a startup in the crypto currency data niche, where he’s currently a Co-Founder and Chief Product Officer.

As often happens when a Founder is working on multiple businesses at the same time, Ben realized that The TIE had a much greater potential market and upside.

Wingman on the other hand, was fairly easy to run and bringing in revenue, but answering support tickets at 11:00 at night after a full day was draining.

So Ben started to think about selling and suddenly we were aware of Wingman and saw a potential fit after both seeing it listed on MicroAcquire and getting a heads-up from Nathan Latka, who knew both of us.

The rest of the story got written very quickly. We had acquired Tradervue in 2020, and had hired an amazing team to run the trade journaling software and replace solo Founder, Greg Reinacker.

One of the Product Managers we had hired to manage Tradervue was an options-focused trader himself, and Ben had already recruited a software engineer from his customer base who was interested in joining the SureSwift team.

Ben liked that we had a team ready to go who would understand his customers and what he had built. We loved how well Wingman filled a specific SaaS niche, its stats, and its well-designed interface.

An Interview with Wingman Co-Founder, Ben Latz

Ben, you graduated in 2017 from Carnegie Mellon and since then you’ve been working on not one, but two successful startups. That’s beyond impressive. Tell us more about yourself — when did you get the entrepreneurial bug?

I’ve had the bug since middle school. I got my start selling candy. And later I hopped into Amazon Affiliates for e-commerce (I had no idea what I was doing). Then I ran a pretty successful business selling custom duct tape wallets for a couple years and went to a couple summer entrepreneurship programs in high school.

It was really in college when I got interested in trading. And I wasn’t running a business at the time. But whenever I wasn’t running something, I was always trying to think of what to build next.

Throughout college I got into options trading and that community. And because I wanted to analyze how I was doing, I made a custom spreadsheet to track my trading. It became very clear after engaging in the community that everyone runs into this problem.

I had foundational exposure to programming at Carnegie Mellon, because everyone has to take a programming class in freshman year, regardless of the school that you’re in. And I had the inclination that what I was doing with my spreadsheets was something that should be automated, because it was really structured.

So it was as simple as thinking, “Hey, this seems like it could be automated.” I didn’t know how to make it a web app. But I knew that it could be done. And I thought maybe I could charge a monthly subscription. I didn’t even know what SaaS was or how hard it would be.

Then in my final year of college, I teamed up with my close friend Piyush, who was studying Information Systems, so he knew how to build web apps and fortunately had the excitement to not only build it from scratch, but the patience to teach me Ruby on Rails for me to contribute. So together, we built Wingman starting in our senior year, and we both graduated a semester early.

That was at the end of 2017. After that we both moved up to Chicago to start our full time jobs, and we worked on Wingman every night and weekend.

I left my full-time job after six months in order to launch Wingman, and months later it was humming along but far from paying my bills. I had a good friend, Josh, who I met at a Babson summer entrepreneurship program for high schoolers. In 2018, he also started his company and later needed help with product and development, which I could help with thanks to the skills I learned from Wingman.

Josh is someone with very big ambition and he’s a bigger thinker than I am in terms of opportunity. So I joined him part-time at the end of 2018. Soon after, I moved back to NY and it quickly turned into full-time.

So that’s how I got my hands full with two things at the same time and I was able to balance them for a while.

When did you realize for both businesses that they could take off? And when did you have that moment where you realized that one was going to require your full-time focus?

Wingman was sort of a success out of the gate, because our initial goals for it were pretty small. It was really just, “Wouldn’t it be cool if we could pay our living expenses with it and get another experience under our belts?”

Ben Latz, founder of bootstrapped SaaS, Wingman, on selling the business.

Piyush and I didn’t show up on nights and weekends to chase a big MRR or an exit, but rather to gain the confidence and practical experience that comes with building a product and running a business.

The early goal was to get to $5,000 a month so we could leave our day jobs. But really from the start, I knew it solved the problem. People were using it, even though it was the most janky user experience, because the page refreshed every time you clicked any button. “If you’re not embarrassed by the first version, you’re launching too late…” so they say.

It was in 2019 that we rebuilt the site to be a lot faster and more enjoyable to use, because I significantly improved my web development through better practices and learning Vue.js. And the word of mouth really started picking up after that rebuild. I started to see all these trials come in, without me posting on Twitter, or doing any marketing.

I think that’s when we realized that, sure, it may take a while, but it’s very clear that this is something that people are going to start adopting.

And then for The TIE, I started working on that full-time in early 2019. I’d moved back to New York, and Josh was there as well, so I’d work out of our two-person office. And then working on Wingman was extra time needed on top of that. So I was always thinking about them or working on them pretty much all day.

We knew that the opportunity in the crypto industry was huge, but it took us awhile to get our first dollar. Then all of a sudden we started doing deals where one deal would be bigger than Wingman’s revenue. And that made the decision to put my focus on The TIE pretty clear, even though Wingman offered an easier lifestyle.

Hey, I get it. Sometimes it makes sense to take the risk for the bigger opportunity. You’ve made a lot of decisions that I think many Founders can take years to get to. You hired really early for being a bootstrapper, bringing on someone to take over some work on support. Tell me more about that.

I actually first tried to hire one of my best friends who’s an options trader to help me with support tickets. He was also starting his own business, and we both came to a very quick conclusion that it was not worth his time to onboard and learn all the ins and outs to provide good support.

A few weeks later, John had signed up as a customer. And he reached out asking how he could support the community — if there was a public GitHub, what he could do to contribute, etc.

I said, “Well, it’s funny you asked, because it would be great to have someone help me with all these support emails.” At that point I was feeling tired of wanting to go to sleep at 11pm just to have to pull up Wingman’s inbox and answer 10 or 15 emails. After doing that every day for three years, it weighs on you.

So it was a jackpot to find someone who actually wanted to do support, and was also a Ruby developer who understood options. That’s a very hard combination to find.

It was very easy to onboard him to be part-time. We agreed to an hour a day, because that’s all I really needed. So it was low-cost relative to the revenue. And it took away the one bottleneck that I felt. It was a no-brainer to give it a shot.

But, I also knew that it would be a waste if I just had him answer tickets. So from the start, we were focusing way more on basically treating him as if he was buying Wingman and documenting what he would need to know to be able to take over.

I knew I’d rather have him produce helpful assets than just answer support emails. So he wrote help articles, and started documenting the code base and infrastructure.

I think a lot of people don’t realize how much work it is to transition the business to get it ready to sell — you were smart about getting ready by hiring. And then you don’t get to just walk away and hand over the keys. Or you could, but that would be a bad outcome. So I really appreciate the work you put in to make it a success.

Were you always building Wingman with a mind to sell? Or was there a specific moment where it just became clear that an exit would be something you would want?

You know, we didn’t think we would actually really ever sell it. It was just too easy to run. Until it wasn’t.

Ben Latz on selling his Fintech SaaS, Wingman.

We had explored the idea about a year ago, I guess around when COVID started. I was burned out and The TIE was also overwhelming, even though we were still in early-revenue days.

So it wasn’t really the game plan to sell. It just sort of happened. There was a tipping point, and I was starting to value my time and energy more and realizing that I can’t do everything.

Once you did decide, I know you had options for buyers. How was that process for you of fielding offers? And why were we the lucky winners?

Yeah, so just as an experiment, we listed on MicroAcquire. Andrew’s a cool guy, and I thought it was a great marketplace. So we just listed it to see what interest we would get.

We got a decent amount of inbound, as the revenue was meaningful but still accessible for buyers. One of the first buyers with interest seemed very serious. He was an individual, but a really sharp guy and we felt good about it. So we were moving along with that, and received an offer from him.

But I decided to text Nathan Latka because I’d been on his podcast and knew about his experience selling one of his companies. I just asked for his advice on handling my situation, because we weren’t sure if we were selling it short .

He made the intro to you guys, and Chris reached out. And that’s how things got started.

The biggest filter (and I was upfront about this with people) was you really had to actually understand options. Wingman’s not really something that you can operate without that domain knowledge. So it was really good to hear that you guys already had people on your team that had that, and another acquisition in a similar space.

And of course, just the fact of working with a fund who does this all the time with standard procedures and a reputation on the line. It’s a lot easier to feel good about that vs. an individual you just met for the first time who’s just doing personal capital and a loan.

I also had a brief conversation with Tyler Tringas (I’m an LP in Earnest), who’d sold to you guys and he had really good things to say so that also really helped.

Oh, nice. We’re LPs in Earnest, too, I didn’t even realize we had that connection. SaaS is such a small world.

What are you hoping for with Wingman now that it’s found a new home with us?

My hope from the start was just to build something that solved the problem options traders faced, and it’s done that for a few years. I think it could be well-positioned as the highest quality tracker in the industry, for options traders.

As long as it continues serving customers well and it does as well as you guys want it to, I’m happy. I don’t have ego tied up in how big it gets.

I wanted to ask you about the crypto space too, because I talk a lot about trying to professionalize the SaaS buying space, and it feels like you guys are trying to do something similar in crypto with The TIE, and it’s another young market. What’s your perspective on that?

Both of us and our other Co-Founding advisors are all from a traditional finance background. So it was really just, “Okay, how do we take pieces that we know work in that industry and bring it over because they’re gonna need that infrastructure at some point.”

But the industry is changing every week. So the challenge is committing to something that is going to be needed through the changing market while still keeping up and not losing focus.

So we’ve really stuck to what type of data we can do differently that we know no one else is really going to do well. We’ve seen a lot of data companies go out of business because they focused on one type of data set that wasn’t commercially viable in the market. So we’ve always tried to stick to what we do differently, and then just form great long-term relationships.

It’s a tough industry. But over the past six months, the tide has risen so much that everyone is doing better. And there’s so much opportunity now that we just keep hiring because there’s just more and more that we could do.

I think the best way to survive is having those deep relationships though, and to work with other companies and lift each other up as the industry grows.

So in your blog, I noticed you were kind of into the FIRE movement and, and living frugally. And I was wondering how that impacts how you approach an exit, and also just if you felt like that allowed you to go out on your own so early?

I think for personal finance it’s important to go to one extreme, and then come back a little bit. I was really into FIRE in college. But being a business owner is very different for the concept of FIRE than being an employee, because employees usually have no upside other than investing all their money in the stock market. And that’s fine. But as a business owner, you can create so much more upside.

So, it helped that I was able to live very lean when I needed to. And, you know, part of that is carried over to not needing much. But I’m looser with expenses nowadays.

If something can make my life easier, or do something quicker or better, I buy without thinking about it nearly as much as I used to.

Obviously, the acquisition has helped. But I’d already been transitioning to more of a business owner’s mindset from FIRE, where you can not need that much, but focus more on building upside, as opposed to incrementally saving a few thousand extra dollars a year, which doesn’t move the needle.

In terms of starting my own business, when I was at my first job, I was saving 60% of my salary. I knew that the amount I’d saved up in six months would carry me through the next eight months or so of living expenses. And that made it a no-brainer to leave and just see what happens. Because the worst case was, I’d get better at web development, and then if the business failed I’d get a developer job.

You sound like somebody who’s very good at having an idea and then kind of testing it out and validating it and going back to adjust. Is that part of your process that’s conscious or is that just something that comes naturally?

When it comes to my life path, I’m in a position to make choices that may seem risky. Even though I’m an analytical person, I don’t obsess over optimizations anymore. Most decisions can be undone, and when they can’t, I’m more careful. Things seem to work out in their own interesting ways even when they appear to fail at first, which makes it easier to go with my intuition.

Bootstrapped Founders Sells SaaS to focus on second startup

Selling into Growth:  After Departing from a VC-backed path, This Solo Founder Built a SaaS to Scratch an Itch, Grew it to 100k+ Users, Then Sold on the Upswing

Selling into Growth: After Departing from a VC-backed path, This Solo Founder Built a SaaS to Scratch an Itch, Grew it to 100k+ Users, Then Sold on the Upswing

After exiting NewsGator, an earlier startup, Greg Reinacker was ready for something new, and he started trading. After trying many trading styles, he soon found the hardest part of trading for him was not the numbers, but the emotional side. He needed a way to efficiently keep his trading journal, and also objectively analyze his performance, and no tools existed that he found suitable. So he started building one and Tradervue was born. Unlike the venture-backed NewsGator, he kept Tradervue intentionally smaller and product-focused. It’s been just him since the beginning. Growing Tradervue to serve 100,000+ traders, Greg followed his intuition and then sold into the momentum.

Recently we sat down with Greg to talk about how his past tech company experience informed his approach to Tradervue, how building a product for himself turned into something more, and how he knew it was time to sell.

An Interview with Greg Reinacker

You’ve got a super interesting background. Talk to me about how you went from getting a degree in Electrical Engineering at CU Boulder to founding your first tech company, NewsGator?

Ha! Yeah, there was a little bit in between that.

My first job after graduating from Boulder was in microelectronics and firmware design at NCR microelectronics, which later morphed into application development, which was an adventure and totally not what I thought I was going to be doing.

I actually started my first company while I was still working at NCR. This was back in the day when you’d write a shareware application, upload it on an FTP site, and hope people would somehow find it. I ended up selling that first business to a coworker of mine.

After NCR I ended up going to a consulting company where I did training and custom development.

From there, I went out on my own, consulting. This was back in 2000-ish, and a friend of mine turned me on to blogging and RSS. As I started using an RSS reader, it occurred to me, “you know, I should be able to get all my RSS feeds in Outlook” (that’s what I was using for email at the time).

I wound up building a prototype, and I posted about it on my blog and said, “Hey, what do you guys think?” I got a ton of feedback overnight, saying, “Please, please build this!” That was encouraging, so I started building, turned it into a product and started to sell it. And NewsGator was born.

NewsGator grew really fast, and you took the venture capital path with that business. What were your big takeaways from that experience, and how did it influence your approach when you started Tradervue?

Yeah, about two years after I launched, it was me and one other guy, and we did our first round of venture capital. And the rest was the story of a venture-backed company: Raising tens of millions of dollars and growing very, very fast.

At our peak, I think we grew to 120 people or so. After about 10 years of doing that, I decided that the company was really doing fine without me, and I felt like it was time to move on and find the next thing.

The venture-backed path is just a whole different world — the pressures you feel are much different. And I mean, our investors were great. I talk to our lead investor who started the very first round regularly and had no regrets along the way.

But it’s just a different trajectory for a company.

Bootstrapping a company myself, if we got to say, $100,000 in revenue or something like that, then I could have done things differently and backed off my time, and been happy with things at a certain rate of growth. In a VC-backed situation, that’s just never going to happen.

Greg Reinacker, founder of Tradervue on building a SaaS to exit

On Tradervue, building solo meant I had the freedom to build the product I wanted, and the product I thought should be in the market, regardless of how long it took to become successful. That patience isn’t always an option in a situation with outside funding.

Tell me more about building Tradervue. It was a personal project that turned into a business, right?

When I left Newsgator, I decided to take up trading. My philosophy was, “I’m an engineer, right? How hard can this whole trading thing be?”

Well, it turns out the hard part of trading isn’t the engineering and math part. It was trying to find what worked for me, what matched my personality, and the whole emotional side.

You might start a position and have it move against you, and you must have a mindset where that’s either okay, or you need to to snap those positions off and take your quick losses. You have to train yourself to do that.

During that process, one of my goals was to have a way to objectively analyze my performance. Sure, your broker will tell you whether or not you’ve made money that year. But what I really wanted was to be able to dive down deeper to figure out what was working and what wasn’t. That was the start of Tradervue.

So when you built this, you built it for yourself. But I’m sure there were times where you were spending all your time on Tradervue and didn’t really have time for trading, or were you always doing both? How did you balance those two things? Did you eventually move away from day trading and focus more on the company?

It was definitely more of the latter, moving away from day trading and focusing on the company. I think being a successful day trader is a full-time job in itself. It requires preparation before the market opens, lots of time while the market is open, and a bunch of work after the close.

I did that for a solid year, met a lot of people, and got a good feel for what would work for me and what wouldn’t. I knew I needed a tool like Tradervue, so 90 percent of my focus started going towards that. And then in terms of my own trades, I started to slowly migrate to different trading methodologies that required less time. But I tell you what, I am absolutely a better developer than I am a trader. And Tradervue is more than happy to back up that statement and slap me in the face with it!

Ha, so it’s good that you figured that out and shifted your focus?

Yeah, exactly. One of the things I was doing was aggressively trading around the price action after earnings announcements. Apple might announce their earnings, and I might trade them the following morning. I thought I was a genius at this, and I would have told anybody that’s where I made all my money.

And then I looked at Tradervue after getting the data in and realized I’m not making any money doing that after all.

There were a few things like that. I’d be emotionally excited enough that I’d convince myself I was really good at them, but Tradervue would show me that wasn’t the case.

Did you have any idea it would turn into a tool tens of thousands of people would use? When did you first realize it could take off?

I’m not sure there was a specific moment. I just grew it, and I did everything wrong, intentionally. They say, “Don’t just build a product and hope people come.” You’ve got to get out there and drum up all this demand first, and then build a minimal version of your product and give it to all that demand and see if it works.

I just didn’t buy into that. At Newsgator, after we started growing, a big part of my job was being on the road all the time, drumming up awareness and demand at conferences. I liked it at first, but after four out of five consecutive weeks on the road, it got to a point where I just hated it. After that, I spent like seven years in a row without getting on a plane.

So when I started Tradervue, I didn’t want to do those things. I wanted to do the parts that were fun for me. If it turned into a great business, that would be awesome. If it didn’t, that was okay, too. I was just finding the next thing for myself.

Bootstrapped SaaS founder sells trading software business

So I started out to build this product that I thought would work for me. That was my original intent — just build something for me, because I had this need. And, as many entrepreneurs do, I somehow got distracted during that process and built something for everyone.

When I did the very first launch, I think there were three or four people I was actively talking to that I had met through trading. We all traded in similar ways, and I was bouncing things off them and getting feedback. That’s how the business really started.

I spent the first six months or so giving it away for free. Which was the opposite of NewsGator. It’s kind of funny, I did everything exactly backward. When I launched NewsGator, I charged upfront – there was nothing free available. But that was a product with mass-market potential, so I grew it in a way that forced it to grow pretty slowly.

Fast forward to the Tradervue days and I launched the product as completely free. In hindsight, it wasn’t necessarily the smartest thing to do. It’s a much smaller niche market, so charging for it made a lot more sense. It took me six months to figure that out.

Bootstrapped SaaS founder sells trading software company

You kept Tradervue a solo project for years. Was that intentional after growing so big so quickly with NewsGator? Did it make the decision to sell it more difficult? How did you evaluate buyers?

Looking back on the early NewsGator days, I found that a lot of the parts that I liked the most were from when we were really small — five people or less. When you’re small you can turn on a dime and do whatever you think you should do for the product. There aren’t all these competing interests and different things to worry about.

When I started Tradervue, I wanted to focus on the parts that I find fun – doing the development and building the product – not being on the road all the time or managing a team. Those aren’t my favorite things.

So I focused on the things I liked and kept it small, intentionally. It’s been just me since the beginning.

As for selling it, it’s sort of twofold. For one, I’ve been doing it for a long time and it feels like it’s time to go find the next thing for me, whatever that is. Also, there was a massive amount of growth over the last six to 12 months. As a momentum trader will tell you, you want to sell into momentum.

Bootstrapped SaaS founder on selling into momentum

Obviously, a private company is a little different than a stock, but intuitively, it makes sense to me to sell into momentum, when things are going great. That doesn’t mean it was an easy decision. Things were doing great. It was a one-person company growing to where it was making a bunch of money, but I really felt like it was the right time.

What are you hoping for with Tradervue as it’s found a new home at SureSwift — if you could look into the future, what would you want to see?

I think from launch through today, Tradervue has filled a niche that’s really necessary. Active professional traders (and developing traders) need this kind of tool. We do things in a way that’s designed for a very active trader.

That’s who the product was designed for because that was the guy I was trying to be when I was building it. I think moving forward, I would love for it to expand its functionality, but keep its focus on the really active trader.

As an example, maybe that means expanding the different dimensions against which you might measure your performance — fundamental data as well as technical data and things like that.

Talk to me about being in tech in Denver. I’m in the Twin Cities, and I’d say we’re both in places with a growing reputation for tech startups, but that wasn’t the case for years. Do you feel like that’s changing? Did you ever feel like it was a disadvantage in those earlier days?

It’s kind of funny, right? You hear a lot about that. All the people in the Valley will tell you (especially like 20 years ago) that if you’re not in the Valley, you don’t exist and it doesn’t matter what you’re doing.

That came up when we were fundraising for NewsGator. We had done the first round with Mobius Venture Capital, which was right up the road in Boulder. But after that, we were out in the Valley raising subsequent rounds. There was definitely some of the “Why aren’t you out here?”

Over the years there’s been a great startup community built in the Denver/Boulder area, which has grown like gangbusters. As a result, not only is there a ton of startup activity, which is awesome, but larger tech companies are swooping in trying to take advantage of the talent that’s here. So the Amazons or Googles of the world will build a facility here. It’s become a really great place to build a tech company.

Right. Now the pendulum is coming the other way. There’s a guy that moved down the block from me that has worked for LinkedIn for 10 years. As soon as the job went remote, he’s like, “Alright, we’re leaving. I don’t want to pay San Francisco/Silicon Valley rates for my rent. So yeah, I can live anywhere now.”

Yeah. It’s a really interesting time. I think a lot of companies that normally wouldn’t have even thought of going remote, have to do it. Charles Schwab is right outside my window. Apparently, they didn’t allow anybody to work from home. And now ever since April or May, I look at their parking lot and there’s maybe 40 cars in a lot for thousands. It’s quite striking what’s happened.

Yeah, it’s gonna be interesting to see whether it sticks, or people go back to the office, or go hybrid.

I know you’re a gadget guy and a car guy — what’s your current tech set up at home? Best and worst products you’ve tried out this year?

Ha, well — being a company of one, and this being early in the transition, that’s my focus right now. But with my tech setup, I’m totally an Apple guy recently. I’ve got an iMac Pro, which is a fantastic computer, and there are iPhones and iPads all over the house. It’s kind of a thing.

I’m also super into cars, and motorcycles recently. So that’s fun. I’ve become a Tesla guy.

I saw on Twitter recently that you had backed the Tesla out of the driveway without being in it.

Yeah, it’s always fun to try out what it will do.

You’re also a crazy productive guy. What’s your routine look like? How did you stay motivated as a solo founder for so many years?

You know, I’m not sure exactly, routine-wise. If I get myself excited about something, I can obsess about it for an unlimited amount of time, so there’s no real ‘secret,’ that’s how I stay motivated. Over the days of building Tradervue, I think a lot of it was watching it grow, watching people use it, and hearing people say, “this product really made a change in my trading, and that’s made a change in my life.” I love to hear that sort of thing.

Any sense of what’s next on the horizon for you?

You know, when I left NewsGator, I told anyone who would listen that I had absolutely no interest in starting another tech company. And yeah, after this one, I don’t know. I’m still interested in the trading community. I feel like I get them, and I could imagine doing something there.

If I was to do something not in that community, I have literally no inkling of what that might be. But my last two companies, I had no inkling until about three months before I did them. Right now I’m not in a rush to make any decisions. In fact, it might be good to try not to decide anything big for a little while. It’s kind of a big deal selling your company when you’re the only person running it!

Two Seasoned Entrepreneurs on Product/Founder Fit, Switching Gears, and Why Self-Awareness Is a Business Skill

Two Seasoned Entrepreneurs on Product/Founder Fit, Switching Gears, and Why Self-Awareness Is a Business Skill

When we acquired the Cross Sell Shopify app, the product hit all of our typical buying criteria. It’s a well-built SaaS product that customers love with a history of growth and more potential.

Our acquisition story for Cross Sell, however, was a bit different than our usual “founded by bootstrapper, bought by SureSwift.” While Cross Sell was initially founded by a bootstrapper, the product had already been through an acquisition back in 2017.

Over 3 years, its second owners Deven Soni and Ryan Kulp rebuilt and redesigned the app from the ground up, took it to its next growth level, and then decided the time was right for them to sell last year.

I’m thrilled that SureSwift was the “win-win” choice when they reached that decision, and I’m very excited to bring you all this interview with Deven and Ryan, who are both seasoned acquirers, investors, and operators in the SaaS space.

An interview with Deven Soni and Ryan Kulp

Tell us a bit about yourselves — what’s your background, how did you wind up owning Cross Sell?

Ryan: So, I moved to New York City after school in 2013, worked for a Techstars company, and over the next few years, I got more and more connected and involved in tech startups, from freelance marketing to product development.

In 2015/2016, I was working at a venture fund in San Francisco. That’s when I got involved with buying and growing companies of my own. And the following year, I met Deven through a business partner, Justin Mares. And that’s when we bought Cross Sell together.

Deven: On my end, I had a pretty traditional finance background early on. I worked in tech M&A in San Francisco, and eventually joined a venture-funded startup. I sort of married those two worlds together and became a Private Equity and Venture Capital Investor at Goldman Sachs for about two years.

After that, I moved to a fund called Highland Capital Partners in Silicon Valley. Then I realized that this whole time that I was kind of a value investor trapped in a technology investor’s body.

And that’s the reason I started a venture/private equity fund called Wired Investors back in 2014, and we bought about 18 digital businesses over the next 3-4 years. About half of those were SaaS, and the other half were media-based. And that’s where I met Ryan and Justin as well.

I know what we liked about Cross Sell, but what stood out to each of you when you bought it?

Ryan: My business partner Justin and I started looking at the Shopify app store in 2016, and we just started creating our own metrics to watch — like the ratio of installs to reviews, and recency and frequency of reviews, and we started plugging them into this spreadsheet model.

Cross Sell hit all the green lights in terms of those metrics as kind of a remarkable product, without even knowing what it was. It was just like, this app has something going on that other apps don’t. And so we kicked the deal over to Deven and said, “this is the one.”

Deven: Yeah, we were talking about Shopify, then like three days later we started looking at Cross Sell.

Ryan: That’s right. We were very careful about not wanting to waste you or your partners’ time, so before we went in on this Cross Sell deal, it had to be the one. So we moved pretty quickly.

But what stood out to me when I found it was the reviews, of course. Then looking at the product, the design wasn’t great. So maybe to one person, they’d say, “I gotta run away because it looks bad to me.” We had a design competency, so I just saw that as a huge opportunity.

Like, you know, the HGTV shows where they see old carpet, and they say, “Oh, we can rip it up and put in hardwood floors.” That was our same approach, how we found the product and why we were able to move so quickly.

I love that home remodeling reference. Did you both already have the idea of a joint venture in mind? Or was it more we’d like to work together and if the right deal comes along, we’ll figure out the structure and how it works?

Deven: It was more the latter. We had a pretty active pool of investors, and Ryan and Justin had a ton of competency in the Shopify ecosystem. We thought that was an area we wanted to dip our toes into more and learn about, so we kind of just started talking.

And from there it was just literally if we find a good deal to work on together that’s big enough to do some cool stuff with, let’s take a look at it together. And that’s what happened with Cross Sell. It ended up being probably four or five weeks from conversation to close.

And what about your goals while you owned it? Every owner approaches things a little differently than the original founder. Give us a snapshot of what it looked like when you bought it, and what your focus was on.

Ryan: For me, as the operator, I needed it to not be the same type of project as Fomo (another Shopify app I was operating), and other projects where I was doing 2 am tickets, fixing bugs, and things like that.

So from day one, I think before we even closed, I created a Trello board “master plan” for the next two years to do everything from rebuild the app from scratch and redesign it, to doubling or tripling the pricing depending on the legacy user.

And we did get through virtually all of that before we transitioned to you guys. That was a plus, for me. And I think also a plus for the product and the customers because when you’re just starting out going from zero to something, you kind of can’t have a plan because the plan is like, don’t die and do what customers tell you to do.

But I think Cross Sell at that time already had 1600+ customers. I didn’t think it needed this shotgun approach of “let’s just do whatever feels good each month.” I thought it needed more long-term planning.

The previous owners, in my opinion, had optimized for minimizing day-to-day work, which is fine for a side project but doesn’t work as well when you’re trying to grow.

So we focused on improving support, because as the product grows, that need grows, and it makes sense to have a Help Center and things like that.

And then on the product side, we wanted to improve it so dramatically that we would begin to stand out from the crowd of these other competitors in the marketplace.

So we kind of inverted some of the day-to-day strategy and operations from the original founder.

And on the pricing front, a lot of times a founder doesn’t know how great something is that they’ve made because they’re humble. We knew we needed to raise prices, and we knew we needed to bolt on some things to future-proof the product.

I think what we tried to do during our stewardship of the product was try to deliver on the vision that was already there, but that the original founder didn’t want to do or didn’t have the time to do since it was a side project for him and he had several other apps he was working on at the same time.

I’m curious when you bought the original code base, did you just buy the Cross Sell code base? Or did you get a bunch of ‘also ran’ apps that weren’t your top priority and you shut them down?

Ryan: I think we got one or two additional free apps or one that was making like $100 a month or something.

The same thing happened when we bought Fomo (it was called Notify when we bought it). We got an app that made $700 a month and had 800 users and it did scheduled Instagram posts, and of course, later, the Instagram API stopped allowing that.

But in both cases, we didn’t bother dealing with the other app, we just shut it down. Because even if we didn’t know exactly what our goals and tactics would be for the app, we knew we needed to do something different than what the previous person was doing, or the app would have taken off for them already. So if the previous person was managing all these little things, then it’s pretty easy to say, “let’s just not do that.” And then figure out how else we can fill our time, focused on a single product.

I think that’s going to be super interesting to both founders and folks who are doing what you’re doing. That’s a really hard call to make. But sometimes when founders take that sort of studio approach, they don’t realize that maybe they should be letting more go and going all-in on one thing sooner.

Ryan: For sure. That’s hard for a founder to do, especially somebody who wrote all the code and had the idea and thinks of it as something super special. It’s easier to do that coming in from the outside.

So you worked through your master plan — how did you decide it was time to sell vs. mapping out the next two to three years?

Deven: With every business, your growth and revenue charts are not always ‘up and to the right.’ It’s more these step functions, right? You tread along until something comes out — like a strong feature, or maybe the market changes in some way, and you get an uptick. And then you kind of tread water again.

That’s not to say that we were treading water, but I think we did a ton of work under the hood to make the product much stronger. And the overall SaaS market was changing. There are more buyers and sellers out there right now.

So, we thought, we have two decisions in front of us. We can go on for the long haul, which wouldn’t have been a bad decision, but things like expanding to a new channel, like BigCommerce or something, felt a lot like starting from scratch. Our other option was to let someone else carry the torch.

And at the time for us that second option just made sense, but I really deferred to Ryan on whether or not it made sense for him and the product. For us, we were broadly exiting our digital portfolio and thinking more about brick-and-mortar, and Ryan was open to selling at that point as well, so I just kind of ran with it and tried to find a win-win relationship.

Ryan: Yeah, that’s right. I think I would summarize it as steam, you know, you have some limited amount of steam. And every project has a different amount of steam. With Fomo, I ran out of steam three months ago — I’m no longer the CEO there. That was a four-and-a-half-year project for me. Our Micro Acquisitions course, I ran out of steam like nine months ago. So someone else is running that now.

Everything has a different kind of half-life. And what if you push through after you’ve run out of steam?

I think in this world, where the reason we have these businesses is to grow them and create jobs, and whatever else, that pushing through after you’ve run out of steam is masochistic. It’s not actually helping anybody. It’s definitely not helping shareholders and partners. And so I think it was the best thing to do for our partners, and for me personally, and I’m really glad it found a new home.

Ryan, you mentioned Fomo, can you give us a quick update on what’s going on there? I think that’s another interesting trend we’re seeing is that people — whether they’re founders who have multiple projects going, or they’re investors/buyers who have a portfolio — are trying to decide how and when to exit one component.

Ryan: Sure. With Fomo, I was working really hard. Basically, that was my full-time thing. And, you know, I got too connected to the growth. I had a good mood if we had an up month and I had a bad mood if we had a down month and I would watch This Is Us for 12 hours. It just got to be a weird relationship with the numbers. And I never thought it would be like that, so I kind of needed to just not do it.

But in terms of more logical reasons, I think there are a few ways to exit a company, right? There’s go public, or sell. There’s shut it down. And then there’s replace yourself.

And I think they could be done in that order, or the opposite order. So many people have tried to go directly to the biggest and the most obvious type of exit, but you kind of need to replace yourself before a good exit can happen, especially for the new owners.

You know, the new owners want to know that the business doesn’t require Ryan Kulp, and Ryan Kulp’s “brand,” and Ryan Kulp’s personal blog newsletter to push things forward.

So for me exiting Fomo a few months ago was a good test of my entrepreneurial chops. Did I create enough systems, enough documentation internally and externally, and enough checks and balances? So far, it’s going well, and they’re still growing. And that’s been a lot more fulfilling to see those monthly stakeholder newsletters where it’s still growing and things are happening when I’m not running it. 

It really kind of came down to ego. And I think a lot of founders — maybe bootstrapped founders especially — have more ego because they kind of deserve it. If you started something and made it happen without investors, you sort of feel like, “I’m a Spartan.” And if you raise money with investors, even if you’re really smart, you feel like well, I owe a lot of people my success. 

And so I think a lot of bootstrapped founders keep pushing through after their time is up because they have that kind of confidence of being a successful bootstrapper. And that’s great. But being self-aware is even greater. 

And for me with Fomo, having that awareness meant knowing I needed to step away. And yeah, it’s been good so far.

Deven, you’re also someone who’s shaken things up throughout your career to find your own version of product/founder fit. Tell me more about moving from the investment side of things to acquisitions?

Deven: I think the reason for the transition was working in finance, you get to meet a lot of companies, and you can see a lot of business models, but it’s transient in nature. You get excited about something, and then you say goodbye and meet the next one.
And even if you’re an investor, that’s the same in some ways — you get the quarterly check-in, and that’s the relationship you have with that business.

I think for me there are many benefits to being an owner of companies, and I think part of that is being able to set more strategic direction, and thinking about capital allocation more precisely.

So those were the main reasons I made the switch. But, you know, in hindsight I wish I had done it earlier. It’s one of those things where I did the day job for probably three or four years longer than I would have if I’d known what the other side looked like.

You made another jump recently — from buying software to buying physical businesses under the Kingmakers name. You provide the systems, but an owner buys in. Is that right? Why the move from digital to physical?

Deven: Yeah, around 2018 or so, we just realized that the process we were using to find digital businesses wasn’t working as well, or the businesses were more expensive. So we decided to try the same kind of strategy of small-cap buyouts with brick-and-mortar businesses under the Kingmakers brand. We bought our first brick-and-mortar business in early 2019, and since then have bought or invested in several more.

We’re focusing on plumbing, roofing, and landscaping — really kind of “boring” businesses that we think have a lot of the same characteristics of digital businesses. So that includes things like low multiples, and you know, not a very liquid market. But they’re also easier to finance, and they’re cheaper. So that’s what we’re doing now.

How is running those businesses the same as running SaaS and software companies and how is it different? Anything universal you’ve noticed?

Deven: I think what’s universal is you’re still gonna get punched in the face a lot, right? Nothing’s easy. It’s just someone else punching you, whether it’s a faceless organization or a human that doesn’t show up to work. I would probably say that on the brick-and-mortar side, it’s more people drama. Someone doesn’t show up for work, or someone shows up to work high, and you have to deal with that. It’s a lot of these personal, visceral kind of human things. And solving for that kind of stuff is tricky, and building a culture in these businesses is just different.

But the nice part about it, the other different thing is every single human on Earth kind of wants what you’re selling, so it’s almost like selling a commodity in a way. It’s not like, you have to try really hard to differentiate your product. It’s more like if you show up, you do a good job, you clean up after yourself, and say “thank you,” you’ve got more business than you can handle, which is a rarity.

So you know, I think the similarity is that there are going to be problems in any business. The difference is the types of problems.

That’s so true — you have to be willing to get your hands dirty running any type of business. Speaking of those common business problems, growth and marketing come up a lot for bootstrappers, so Ryan, I’m curious what are some of the first things you look at there?

Ryan: I think one thing bootstrappers often leave on the table is extracting the amount of value that they’re providing in terms of pricing. You know, I just had lunch with my tutor in Korea yesterday. He was nervous about raising his prices for his online students. And I asked him, “Why? What is the new pricing?” Are you afraid too many people are going to cancel and you haven’t modeled out how many people you can afford to lose?”

He said, “No, no, I’m just nervous about who will be angry. If people cancel, I’m okay with that. I want more time for other projects.”

It turned out he’d raised prices before and when I asked him what happened, he said “Nothing, nobody complained.”

I think this is someone who has kind of the same mindset as the SaaS bootstrapper. He has a good product — it’s kind of premium tutoring, and he charges a lot more than most tutors here in Korea because his English is at such a high level. And he’s raised prices before successfully. But it doesn’t matter. He still has this fear of raising prices, and the emotional backlash that might happen.

So extrapolate that to SaaS founders with hundreds or thousands of customers, they tend to see the value of the product as whatever their first price was. And on the one hand, I mentioned earlier, I think bootstrappers have some ego. But on the other hand, they have blind spots, too.

So they have some ego, that they’re badass, but they have some blind spots that their product is worth it. Because frankly, a lot of bootstrappers start these little niche tool products to compete with someone that they think is too expensive. So what do they do? Their first step is to make their product cheaper than that competitor.

So as a marketer, one thing I look for is whether a product is worth a lot more than they think it is. And it’s not really about my opinion. It’s about their customers, of course. But if I think the answer is yes, then that’s immediately an opportunity to make something bigger without writing a single line of code.

Deven: That’s almost the number one playbook in our businesses, too — we look for plumbers and HVAC technicians that are underpriced because it’s just really easy to change.

So you’ve both moved out of SaaS for right now. Deven, you’ve gone on to a different business segment, and Ryan, you’ve moved to Seoul and you say you’re retired from SaaS. How are those K-pop aspirations going? And are you definitely retired or just taking a break for now?

Ryan: I’d like to think I’m retired from SaaS, not from working. I’m still very interested in acquisition, and entrepreneurship through acquisition — I think there are unlimited benefits there. Right now I’m looking into acquiring two cafes in Korea. But if I do buy a cafe and totally fail at it, I might have a reality check that I should go back where I belong, and then I’ll probably see you guys on another call soon.

The Launch Is Just the Beginning: An Interview with SaaS Business Builder, Moritz Dausinger

The Launch Is Just the Beginning: An Interview with SaaS Business Builder, Moritz Dausinger

Moritz was one of SureSwift’s earliest founders. In 2016 he sold us Mailparser, which automatically extracts data from emails to automate repetitive business and admin tasks. Then in 2018 he sold us its sister startup, Docparser, which extracts data from PDFs. And those two acquisitions weren’t even his first. He’d previously co-founded and sold a SaaS ticketing startup to a Paris competitor.

Selling three businesses could be an easy road to a big ego and retirement for a different kind of person. But Moritz just launched a new startup called Refiner a couple months ago after working on the project for over a year, and he remains as curious, insightful, and humble as ever. 

Recently we caught up to talk about his new project, how he got derailed on the way to launching it, and why he thinks one business success doesn’t guarantee your next.

An Interview with Moritz Dausinger

You’re a pretty popular guy in the bootstrapped SaaS community  — Arvid Kahl and Danielle Simpson who sold us FeedbackPanda last year actually heard about SureSwift from your interview with Indie Hackers — but for people who don’t know you, tell us a bit about yourself. What’s your background? How did you become an entrepreneur?

Thanks for the kind introduction! It’s just amazing how many positive things came out of this one Indie Hackers podcast I did back in 2017. I got to know so many great founders thanks to that, and what I said apparently resonated with quite a few people.

My background is in engineering and after all these years I would still consider myself primarily an engineer. I taught myself coding during high school and since then I’ve built countless small websites and apps. I studied electrical engineering, so I’m basically an auto-didact when it comes to web technologies and entrepreneurship.

I started my career as a research associate in Germany but quickly realized that I actually want to build “real” things instead of staying theoretical. So I took the leap into entrepreneurship and founded my first company together with a friend, building a ticketing software for event organizers. 

We were able to bootstrap our company to profitability and got acquired by our competitors in Paris ( After the acquisition, I became their CTO and we spent a couple of amazing years working there. Working in a venture-backed, high-growth startup was a great experience and I learned a ton of things there.

What followed was me becoming a “serial entrepreneur,” even though I don’t like this expression that much. 

During the last five years I bootstrapped two B2B SaaS products – Mailparser and Docparser

I was lucky enough to sell both of them to SureSwift Capital, Mailparser in 2016 and Docparser in 2018. After working with SureSwift for nearly a year it was time for me to start building something new though. In 2019 I started working on a new project (Refiner) which I just launched a couple of weeks ago.

SaaS business builder, Moritz Dausinger, just launched a new bootstrapped startup, Refiner.

That’s interesting, why don’t you like the term “serial entrepreneur?”

I think it’s overused. To me, it implies that you started a lot of businesses, but not necessarily that you had any success with them. So you could constantly be starting projects that never go anywhere, and call yourself a serial entrepreneur.

That’s totally true. Other terms feel like they sell you short though! 

One of the common pieces of business advice I think we’ve all heard is that ‘you should know what problem you’re solving before you build anything.’ Do you agree with that, or do you think you just need a passion for exploring problems until you find one that has a business case? 

Oh yes, I definitely agree with that when it comes to actually coding something. It just makes sense to first validate an idea by interviewing people, building mock-ups, trying to find first customers who are willing to buy even if there is no product etc. … In theory.

To be honest though, it’s not really how I work. 

It’s really difficult for me not to start coding when I’m working on a new idea. For me, building something new is a lot of fun and I’m apparently not disciplined enough to only stick to market research first.

The way I was working in the past looked like this: I had a vague idea of an underserved market or an interesting technical idea. I would then try to build a really reduced first version in a short amount of time and put it online. From then on, I would iterate a lot on the idea based on real user feedback.

When working like this, I think it’s important to have a balance between keeping your ego low and listening to what your early users say, and having your own long-term vision for the product.

I think starting with the right idea is important, but first-time entrepreneurs especially tend to put too much weight on it.

"I think starting with the right idea is important, but first-time entrepreneurs especially tend to put too much weight on it... it's better to assume that you don't know much about the market needs in the beginning of a project, but that you'll become an expert over time." - SaaS Founder, Moritz Dausinger
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I think it’s better to assume that you don’t know much about the market needs in the beginning of a project, but that you’ll become an expert over time. 

In any case, I’m convinced that it’s most important that you are passionate about the project, that you show up every day, iterate, and continuously make small improvements.

Mailparser and Docparser both turned out to have a big business case. Did you ever imagine they would have the success that they have?

Definitely not! Mailparser started as a personal project without any financial goal. I liked the idea from a technical point of view and thought it would be fun to build it. 

However, after launching Mailparser on Hackernews I quickly learned that there was actually a business case for it. I then started to think that Mailparser could become a nice revenue-generating side project. I was basically aiming for “a couple of hundred bucks of passive income” in the beginning.

But after a couple of months I started to realize that what I’d built had a lot of potential. A bit more than one year after launching Mailparser, I went full time on it with the goal of growing it into a real company.

Did you always think you would sell Mailparser and Docparser, or was there a specific metric you wanted to hit, or an “a-ha” moment where you just knew it was time for you to work on something else? Tell me a bit about your thought process when you were deciding to sell. 

When I realized that I was sitting on a project with a lot of potential, I was definitely asking myself questions like how big this could become and what the future could look like.

Pretty early on I started reading about small- to medium-scale SaaS acquisition and thought that it would be an ideal outcome to sell the business one day.

Luckily, Mailparser and Docparser were profitable really early on which allowed me to grow the business on my own terms, knowing that I could sell them one day if it made sense. 

I also never took any external investment and kept all the decision power to myself. Which meant that there was never a moment where I felt pressured to “go big or go home” as is the case for venture backed companies.

A couple of years in, my personal situation changed in a way that it made sense to think about selling at least one of the two products. The risk was also getting bigger — the bigger the businesses got, the more I had to lose.   

With SureSwift, I found the perfect buyer and we agreed on a pretty special deal: You bought Mailparser in an all-cash deal and I kept on growing Docparser. Everyone told me this wouldn’t be possible and I’d have to sell the businesses together. But you got it, and it was always a win-win, “let’s go there together” approach. So I sold Mailparser, and we had a handshake deal that SureSwift would get first refusal if I wanted to sell Docparser later on. Two years later, the business was at a point where a follow-up acquisition made sense for both of us.

Tell us about your new business, Refiner. 

Was Refiner a tool you wished you had when you were running Mailparser and Docparser? How did the idea start, and when did you know it was going to be your next business? 

Refiner is a customer survey tool built specifically for SaaS, eCommerce and membership sites. 

The idea for Refiner was born when I was still in charge of growing Docparser. At Docparser we had a very mixed bag of signups, ranging from people who just wanted to look around, to product managers with a clear purchase intent working at a Fortune 500. 

Furthermore, Docparser supports a variety of use cases and we wanted to make sure to send the right kind information to the users who could benefit from it.

So we needed a simple tool that would allow us to “profile” our users on the fly by asking them simple questions. I looked at existing in-app survey solutions but ended up developing a popup form myself. This is where Refiner was born.

Is there any way that having had those earlier successes made starting a new business harder? How was starting Refiner the same or different from your previous businesses?

Oh well … I have so many thoughts about this that we could probably do another interview. 

There are plenty of things that just get easier the more often you do them. You have a better idea of how long things take, how much work there is to do, and what to expect in the early days.

Being able to properly self-fund Refiner is a great position to be in. I can build Refiner on my own terms, at my own speed, and have the possibility to get outside help whenever needed. It makes things much less stressful.

However… there are also so many things that just keep being really difficult.

Especially the critical things in the beginning like understanding how a market works, what exactly you need to build, etc. stays really, really hard.

Building a bootstrapped SaaS business is a rather long marathon and not a quick sprint.

When I started with Refiner I thought it would be straightforward and easy to build another SaaS. Guess what, I was wrong about that!

I spent the better part of 2019 building something nobody needed. It took me months to realize that I somehow got derailed on the way and admitting it was not easy. 

A couple of months back I decided to scrap most of the code and go back to the initial vision of Refiner. Since then, it’s been on a great trajectory.

I’m a big fan of the author, Seth Godin. He talks a lot about how hard it is for people to “ship” things and consider them done. How do you decide a product is ready for customers to use?

I’m a big believer in “done is better than perfect”. But like most creative professionals, I’m constantly struggling with this. 

On the one hand, I want to ship a beautiful product that I can be proud of. I definitely have the tendency to attach my ego to what I’m building.

On the other hand, I know early feedback is crucial. Especially in B2B SaaS, building the right thing based on customer feedback is more important than tweaking color codes for another week.

My answer to this dilemma is building “small” products in terms of functionality, but always trying to make them look nice with a great UX.

You launched Refiner pretty close to the start of COVID-19. What has it been like starting a new business right now? 

The timing was a bit unfortunate indeed. I wanted to ship Refiner in early March and then reward myself with a trip to FounderSummit in Mexico. 

The launch on ProductHunt went pretty well and I got some great early traction thanks to it. However, a couple of days later things started to get serious around COVID. 

It’s difficult to say how much COVID-19 has impacted the early growth of Refiner as I don’t know what things would have looked like without the crisis. What I can say though is that I’m happy with how things are evolving at the moment. I see a handful of signups each day, receive great feedback on the product and things seem to go in the right direction overall. 

The bigger issue for me is that I have much less time available for work these days. Turns out, keeping two kids entertained all day long is a lot of work.

My to-do list is getting really, really long these days thanks to feedback I’m getting from early adopters. Obviously, I’m looking forward to when I can put in more hours again.

It’s hard to hire when you’re bootstrapping your first company because you’re quite literally taking money out of your own pocket. One of the luxuries of working on your second, third, or fourth business is hiring earlier. What did you learn about hiring from running Mailparser and Docparser that you’ll use (or have used) at Refiner?

I’m in the lucky position that I don’t need to hire a developer to get started with a new project. I really enjoy that part of the work and I think it allows me to create a lot of value early on by myself. As you know, hiring a great engineer is really difficult and also very expensive.

For Refiner I’ll probably use the same hiring approach that worked for me with Mailparser and Docparser: hire slowly and less.

I like to keep my team very small and work with people who are either already very experienced or who can grow into a role and take ownership after a couple of weeks. Personally, I hate micromanaging people and prefer working with people who can work autonomously on a topic. This is especially true for me in a remote setup.

Any closing advice for other founders out there?

One thing I would like to emphasize is that building a business is never easy, even if you’ve done it several times before.

Having the necessary skills to actually build something and be passionate about what you are doing is for sure a prerequisite. But building a SaaS business has also a lot to do with showing up every day, putting in the hours needed, keeping your ego low, and listening to what people say.

It strikes me each time how much work is involved in just launching something. And launch day is when the journey actually just begins. It’s important to keep this in mind. Building a bootstrapped SaaS business is a rather long marathon and not a quick sprint.

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