The Story

From the iPhone launch to two exits โ€” the short version.

My Silicon Valley career started while I was a Computer Science student at Brown University. I was leaving class from the Computer Science building when someone from Apple offered me an interview. It was a woman from the WebKit team. Normally I would've already been out the door, skateboarding back to my dormitory, but not this time. This was Apple. I took the impromptu interview where she grilled me on a whiteboard coding string manipulation algorithms in C. At the end of the interview I thanked her, and got back on my skateboard to head home.

My phone rang while crossing Thayer Street. It was the woman from the WebKit team. She offered me an internship at Apple.

And so it began — a surreal time in my life where bumping into Steve Jobs was something that regularly happened. When almost all of my meals were eaten at Infinite Loop in Cupertino. When secrecy was mandatory.

Jason at work

I joined Apple fulltime after graduating from Brown. From there I was eventually recruited by legendary venture capitalist Tim Draper to CTO my first startup. That company ended up getting acquired by Coinbase. Since then, my journey has taken me through endless adventures in the tech industry, with my most recent startup exiting to Krea.

Now I run Hermetic Ventures โ€” a boutique venture builder โ€” and I write about what it takes to build and run agentic systems in production. The next chapter is ExpertFounder: helping technical founders cross the gap I've crossed twice.