Why I Left My Job as Principal Engineer at a $100M Startup

I built the software organization at a $100M startup. Then, I left to build online.

Zero To One

When I joined the company (SaaS + AI + Embedded), we had less than 10 employees, no software product, and no revenue. I was drawn to the challenge of building a team and product from a blank slate.

Over the next 5 years, I built our software product from scratch. We won a big customer, and raised a Series B.

Then we raised a Series C, and it was time to grow. I hired three teams of engineers, until the software organization I led was larger than the entire company had been at the time I joined.

What Now?

While I had succeeded at what I set out to accomplish, I missed the early days. There were no cards or stand-ups - you just build or the company dies.

I took some time to revist a side project - a 3D sandbox game using WebGPU, and written in Rust. I became completely absorbed by it, and was back to clocking 14 hour coding sessions. It was refreshing to build something from scratch, rather than iterating on an existing solution.

However, I knew leaving my job to build this game was risky. It might take a year or more to build something that was actually fun to play, and even then I still might not attract any users.

I could join another early stage startup, but that would also be risky, and in five years I'd be back to the same place.

I wanted the kind of diversification VCs have - exposure to many small bets. And I needed a fast iteration cycle, so I could learn quickly and have more chances to succeed.

The Plan

Over the years, I've built up a collection of ideas for small projects.

My current plan is to build a series of them, starting by solving my own problems. Then, as I learn, increase in scope and complexity.

I'm sure this approach will evolve over time, but I'm excited for the road ahead :)

If you'd like to follow along, I'll be sharing what I learn both here and on Twitter: