Three years ago I was given an unexpected choice — shut down my side project in order to keep my job, or leave and go full-time on it.
As a senior in college, 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 micro businesses since middle school, I liked the idea of continuing to do my own thing. But I didn't believe it was possible to start something that would cover post-grad living expenses — my biggest success until that 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 employee #2 at tastytrade's new venture, Small Exchange. It was the perfect 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 Carnegie Mellon. 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 became serious, working nights and weekends until Apr 2018, when things unexpectedly changed.
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 lasted for a few days.
Soon after launching the landing page, I get called to a private room with the CTO of tastytrade. It became 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 shook me. I got 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. Plus the thought that I may lose the effort Piyush and I had put into Wingman so far. This unexpected intensity broke me into tears.
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 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 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 felt like the decision was not risky, in terms of the potential to experience 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 memorable day. 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. "Why are so many people 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 seeing the practical possibility of making 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 deeply fulfilling. 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 moved 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 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 profit 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 signed 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 ($4k/mo), 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 effortless, but something that breaks the linear relationship between time and reward (the requirement for wealth).
I got lucky being so naive about the difficulty of starting and growing a B2C 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 for 20-somethings who want to work for themselves but doubt it's possible. For me, it took learning web development, deep knowledge about options trading (scratching my own itch), well-planned personal finance (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.