Leaving Stripe

I originally got hooked on programming because I loved the act of creating something from nothing. I soon discovered the deep satisfaction of having others actually use my creations. It didn’t take me long to realize I wanted to build a startup.

Startups #

Throughout college, I tried working on a bunch of startup ideas, none of which went anywhere. From each I learned another thing not to do (“don’t blindly follow someone just because they have an MBA”). I knew I needed to learn more, to find the right collaborators, before I could hope to be successful on my own.

When I met Patrick, John, and Darragh, who were working on a stealth-mode startup called /dev/payments, I knew my search was over. I left school to join their founding team.

Over time, my role evolved as I did whatever was needed to help make the company more successful. About six months ago, I found myself in a strangely luxurious place: I’d successfully removed myself as a critical lynchpin for the company and could craft literally any role I wanted.

But the more that I explored, the more I realized: I was yearning to create something of my own. I’d helped build Stripe from four people in a room to nearly 250 employees across four continents. I’d worked on nearly every part of our business, and I’d seen many of the people I helped support grow into leaders within the company. While there would always be new skills to conquer, I felt I’d topped out the S-curve for what I could learn here about starting a company.

Departing #

Choosing to leave something you love is never easy. In some ways, it would have been easier to have a forcing function: being fired or for the company to have failed or been acquired. But Stripe is doing better than ever, there’s plenty of impactful work to be done, and we’ve successfully built an incredibly thoughtful company that keeps adapting as it grows.

Right now I’m in a rare window. I haven’t yet placed myself in a new critical role, and I’m confident that Stripe is being left in great hands. If I don’t take advantage of this opportunity, I’ll always wonder what could have been. Sam Altman put it well: life is not a dress rehearsal.

Friday will be my last day at Stripe. I’m incredibly grateful for having worked as part of such an amazing group of people (missing them already :/). I’ve learned more from them than I can possibly describe, and I’m looking forward to seeing everything they accomplish from here.

What comes next #

I haven’t decided exactly what I’ll be building (feel free to ping if you want to chat). But for now, I’m looking forward to exploring some ideas I’ve been thinking about for as long as I’ve been programming.