What I've built and invested in
I cofounded Chef, the open-source infrastructure automation platform adopted by Facebook, Google, Apple, and IBM. Chef was acquired for over $220 million. I was founding CEO, and the company’s success was built by thousands of incredible people. The engineers, contributors, and community members who made infrastructure as code a reality.
I cofounded Orion Labs in 2013, a real-time AI voice platform for frontline teams. The idea came from my background as a firefighter. On a fire scene, you can’t type. You can’t swipe. You need voice-first computing that works in noisy, high-pressure environments with zero margin for error. Orion built that infrastructure and anticipated many of the agentic AI patterns now emerging across the industry.
Before all of that, I was Amazon’s Master of Disaster, where I created the Incident Management program and the GameDay practice that pioneered chaos engineering. That work, and the communities I helped build around it, became the foundation of the DevOps movement.
My personal and firm portfolio includes over sixty companies. I invest in this category because I have lived it.
Nineteen portfolio companies are valued at $500M or more. Five went public: PagerDuty, Instacart, Fastly, Caribou Biosciences, and Zymergen. Fourteen are private companies valued at $500M or more, including Snyk, Figure AI, Shield AI, LaunchDarkly, Sanity, Tailscale, Axiom Space, Netlify, Blockdaemon, Eight Sleep, Honor, Firefly, Kentik, and CircleCI. Nine were acquired, including Chef, Conjur (by CyberArk), Particle (by Qualcomm), TruSTAR (by Splunk), and Anchor (by Infoblox). I was an early advisor to Fastly, PagerDuty, and Instacart before their IPOs.
The active portfolio spans AI developer tools, infrastructure, defense, robotics, biotech, and fintech. I sit on the boards of Continue, Musical AI, Colimit, Memgraph, Vibrant Labs, Sanity, Recce, and Mobot. Investments include Snyk, Tailscale, LaunchDarkly, CircleCI, Netlify, Gradle, Groundcover, Figure AI, Shield AI, Epirus, Axiom Space, and Radian Aerospace.
Business Insider named me one of the 30 most successful early-stage startup investors in the world.
The pattern across all of it: I build the tools, then build the communities and movements around them. The tools mattered. The movements they created mattered more.
Further reading
- 30 Most Successful Early-Stage Investors — Business Insider, 2024
- Jesse Robbins on the NYSE Floor — NYSE, 2019