Three years ago I was given an unexpected choice. I could shut down my side project to keep my first job out of school, or leave and go full-time on it.
As a senior in college, I faced the dread of knowing that I needed to find the companies I wanted to work for, apply, and hopefully secure an offer at the start of the school year.
Having run my own tiny businesses since middle school, I felt no desire to work for someone. But I had no belief it was possible to start something that would cover post-grad living expenses — my biggest success until this point was running a duct tape wallet business that made $15k over two years. My expenses aren't that lean.
The only possibility I entertained was to continue working for the company I had been interning at for a little over a year. So, that's what I did.
I joined as full-time employee #2 at tastytrade's new venture, Small Exchange. It was an amazing opportunity to see how veteran entrepreneurs would start an ambitious new business, from the start.
In the meantime, I was building Wingman with my friend Piyush at CMU. We both happened to graduate a semester early in Dec 2017 and moved out to Chicago in Jan 2018, where we both had our first jobs (at separate companies). The Wingman journey suddenly became serious, working nights and weekends until Apr 2018, when things took a turn.
As our excitement was ramping and our patience running out, we launched a landing page to invite people to sign up for early access. It went well! Got around 250 signups in the first couple days thanks to my 1,000-follower Twitter account.
That excitement was about to get slammed into the ground.
Days after launching the landing page, I get called to a private room with the CTO of tastytrade. It became instantly clear that he was not happy with Wingman being a commercial project, as it could be a conflict of interest with tastytrade, given the overlap in customer base and proximity to product efforts at tastyworks (a subsidiary I didn't work at).
To put it kindly, he was inappropriately furious, which was a shock to me. I had gotten approval to work on this from tastytrade leadership as a side business and put it in my employment contract to be clear on ownership.
The hardest part was realizing I had become a villain in the mind of a leader of an organization I had built so much goodwill and trust with over a couple years, and enjoyed working for. That, plus the thought that I may lose the tremendous effort Piyush and I had put into Wingman so far. This unexpected intensity resulted in heavy crying and slight trauma — I don't recommend.
Either I shut down Wingman to continue working at Small Exchange, or I leave and work on Wingman full-time with $0 in revenue, only having onboarded a couple test users.
On my walking commute home that same day, I knew the answer, and it was easy. I called up Piyush, and then my parents, to explain the situation and my thoughts.
It was time to make the jump.
I didn't expect to work for myself until I was at least 26 or so, assuming the need to build up years worth of experience first ("put in my time").
Fortunately, I had been into FIRE and saved 60% of my after-tax salary for 6 months. My apartment lease in Chicago was up in Feb 2019. I knew exactly how much I spent each month all-in and could make it until Feb just on the money I had saved from working. I also had a lot of savings before this, which made the financial part a non-issue.
The worst case was that Wingman flops and I would've enjoyed a taste of freedom and learned enough web development to get a developer job, which would pay more than I was previously making anyway.
I had no responsibilities and didn't feel like the decision was risky, in terms of potentially experiencing meaningful loss.
My last day was May 11, 2018. Now I'm on my own.
That was a Friday, and the next Monday was a day to remember. I walked to the Apple store to reset my computer and recall a funny feeling seeing so many people walking around town in the middle of the day. "What do these people do such that they can be out during the day? Don't they have jobs?" It was a kind of obvious realization that there is a lifestyle outside of the 9-5 day job.
Even though Wingman hadn't even launched yet, it felt like I had escaped the day job cycle, never to return. And after freeing my mind up to the practical possibility that I could make it on my own, it became a lot more realistic to imagine earning enough to live, given some useful skills and time.
The 100% ownership over my time, where I could go for walks, run errands, hang out at a bookstore, or do absolutely nothing, was an amazing feeling. The next six months was filled with learning, introspection, aloneness, and calmness.
Though Wingman was built and had people using it, it was far from paying the bills. So in November 2018, I started working part-time on The TIE with Josh as a potential way to keep the dream alive.
The skills I had picked up over the year were directly applicable to The TIE, and then of course I learned even more from The TIE that I was able to bring back to Wingman.
In Jan 2019, I move home with my parents in New York to buy me some more time to see Wingman grow and for The TIE to start earning money. I ended up living at home for nine months before moving to Austin. Even though I could afford to live on my own from savings, there was no point in staying in Chicago and then no point in paying for a NYC apartment. At least now I could work with Josh in person, as he was living at home in NY too.
This turned out to be a great move, as it was enough time to see Wingman creep up to rent money, while shifting my full-time focus to The TIE hoping that would start to generate revenue. Seeing that growth and knowing I'll be fine even if I had to do some freelancing (backup plan), I ended up moving to Austin in Oct 2019.
I was able to live pretty lean in Austin and Wingman was growing about 10% each month consistently. My share of the revenue reached my living expenses in Q1 2020. That was a cool moment, even though objectively it was hardly any money. But making $24k on my own felt much sweeter than a $70k job salary.
The TIE got its first deal in Mar 2020 as well, and even though I didn't end up taking any salary until July 2020, I knew I'd be fine. I felt like I pulled off the jump from job to independence.
Once the salary started from The TIE, the combination of my earnings from the two exceeded the tastytrade salary that I left. The guys at Tropical MBA promote the idea of the 1,000 Day Rule, which is how long you should expect it to take to replace the salary you left. On July 7, 2021 (Day 787) I declared victory. Though, this was just finding the starting line.
When you're on your own, it becomes obvious how quickly uncapped upside can grow. There's no more waiting for a boss to approve a salary bump, hoping for a moderate bonus, or reaching a cap on commission. When the revenue of a SaaS product is growing 10% month over month (~doubling every 7 months) without doing anything other than customer support, and the profit margin is over 90%, the work pays off — it becomes an asset. Far from a walk in the park, but something that breaks the linear relationship between time and reward (the requirement for wealth).
This said, I got lucky being so naive about the difficulty of starting and growing a SaaS business — it's probably not the smartest business to start off with. It's a very slow ramp up to revenue, highly competitive, and is a never-ending wheel of customer support, bug fixing, and feature requests.
I would instead highly recommend reading Nathan Barry's strong articulation of a more gradual, higher probability path to succeeding on your own: The ladders of wealth creation.
To round out the story, we just sold Wingman in Mar 2021 and The TIE is up to 20 full-time employees and growing, which is hard to believe.
I wrote this with the 20-something in mind who wants to work for themselves but doubts it's possible. For me, it took learning web development, deep knowledge about options trading (scratching my own itch), well-planned personal finances (safety net), getting started, and unreasonable perseverance. Even if you don't nail the first idea, it'll bridge you to the next one. All that matters is covering your living expenses and then you're on your way.