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.

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.

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An Interview with Wingman Co-Founder, Ben Latz

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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.

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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?”

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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.

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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.

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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.

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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?

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

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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.

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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 SureSwift 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.

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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.

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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.

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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.

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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.