This is the story of why I left a few million in unvested stock options to be a full-time indie hacker.
Almost 3 years ago, I joined a tiny startup that has since become a multibillion-dollar juggernaut.
When I first joined, I fell in love with making stuff that grew the business and made customers happy. It was my dream job. Every day was different, each experiment worked differently. It was, quite honestly, the best dopamine.
The next opportunity became hiring and managing. It was a new challenge. I was building society-approved career momentum. More dopamine.
As the novelty wore off, I came to the realization that I wasn’t interested in the next level up. Being a Director/VP is gratifying in theory, but not so much up close. I lost interest in the game.
Still, it was hard disentangling my identity from being an early employee at a successful company. I felt massive FOMO.
If you’re on a rocket ship, why would you jump out mid-flight? Yet somewhere along the way, our paths had already quietly diverged.
The company has grown 20X in size since I joined. Whenever that happens, you end up doing multiple tours of duty. You take on different missions based on the company’s needs. And you hope dearly that you scale with the company, which is corporate speak for growing the scope of your contributions proportionally.
For the most part, I was scaling. But the journey that was once an exciting adventure turned into an exhausting slog in my final months. A new revelation began to dawn on me: I wanted to build freely, and on my own terms. Even if it meant making less money, and taking on more personal risk. Working at a startup is hard enough without feeling like your heart's not in it.
A steady paycheck and a lot of unvested stock options is hard to turn down though. When you get good at trading your time for money, it’s hard to imagine replacing it with something else. I narrowly escaped this trap by reminding myself that it’s always worth trading money I have today for something I would regret at the end of my life.
I used to think a career meant working at a company. Then I learned you can start a company. Now I believe a career is simply about making something people want, and capturing some of that value.
Why trade time for money when you can trade value for money? The internet has massively expanded the spectrum of possible careers — a generational shift that remains highly under-appreciated.
Even so, I’m still terrified to embark on this third act. Act 1 was learning to analyze businesses as a consultant. Act 2 was learning to operate a business as a PM. Act 3, I hope, is learning to bootstrap a business.
I’ve never identified as an entrepreneur. Is building a business a learnable skill? Stay tuned.
The first idea I’m playing with is around productizing my experience. Setting metrics, building products, and storytelling are valuable skills. It’s taken me years to learn, and they tend to be gated behind the walls of select places. I plan to build in public, and teach everything I know.
New to this community, but grateful it exists!
You can read my full story here, including learnings on money and startups: https://productlessons.substack.com/p/this-is-my-stop