What I've built and invested in

Adam Jacob, Barry Steinglass, Nathan Haneysmith, and I cofounded Chef. We wanted to bring powerful infrastructure automation to the masses and build a core configuration utility for the internet. The custom tools built by Google, Amazon, and a few others were closely guarded secrets. We opened them up to everyone else. Chef let engineering teams define infrastructure as code, writing recipes to configure entire fleets of servers instead of managing them by hand. It was adopted by Facebook, Google, Apple, and IBM. We grew Chef to $75M in revenue and sold it a few years later. I am proud of what we built and the community we helped nurture.

I cofounded Orion Labs in 2013, a real-time voice AI platform for frontline teams. The idea came from my background as a firefighter.

Before all of that, I was Amazon’s Master of Disaster. The role had me on the hook for the availability of every property bearing the Amazon brand, which took me across most of Amazon’s teams and systems. I helped define and deliver Amazon’s shift to always-on architecture and built the GameDay practice. Adapting the Incident Command System I learned as a firefighter, I built three connected practices as one body of work: modern Incident Management, and what we now call Site Reliability Engineering and Chaos Engineering. That work became part of the foundation of the DevOps movement.

I have invested in and advised over sixty companies across AI developer tools, infrastructure, defense, robotics, biotech, and fintech.

Business Insider ranked me #2 on the 2026 Seed 100, its annual list of the most successful seed-stage investors.

Further reading

• Seed 100: The Best Early-Stage Investors of 2026 (#2) — Business Insider, 2026
• 30 Most Successful Early-Stage Investors — Business Insider, 2024
• Jesse Robbins on the NYSE Floor — NYSE, 2024