Jesse Robbins
Hi, I'm Jesse Robbins. Today I focus on investing in and advising founders building AI developer tools and infrastructure. I think of this as turning startups into the operating systems for entire industries.
Before that I cofounded Chef and the DevOps movement. Building Chef on Apache 2.0 was controversial at the time. Leading investors told Adam Jacob and me that you "can't build a venture funded business on Apache 2.0" (won't call them out by name now :-). We were fortunate to get advice directly from Brian Behlendorf and encouragement from Nat Torkington. Adam captured the decision at the time, down to our use of standard Apache CLAs, which, hard to believe now, was controversial too.
Before that I was Amazon's "Master of Disaster," responsible for keeping every site that carried the Amazon brand online. Adapting the Incident Command System I had learned as a volunteer firefighter and EMT, I built three connected practices as one body of work: modern incident management, and what we now call site reliability engineering and chaos engineering. I created GameDay, the deliberately-breaking-production drill, which is the most visible and entertaining. Netflix named their adapted version Chaos Engineering, which expanded it as a professional and technical practice and improved on the name. I cofounded O'Reilly's Velocity Conference with Steve Souders to share this work.
Open source is still the most powerful force in IT, and community is a superpower.
I cofounded Orion Labs, and I've invested in and advised companies including PagerDuty, Instacart, Fastly, LaunchDarkly, and Tailscale.
The thing I keep coming back to: AI agents are just another kind of developer, and delegation is becoming the new automation.
Building & on boards
Cofounded Chef and Orion Labs. On the board at Memgraph, Sanity, Continue, Recce, Mobot, Musical AI, Particle, and Colimit.
Open source
Projects I contribute to as a credited contributor:
- maclocal-api — Apple Vision OCR, on-device speech and TTS, and embeddings APIs for local models on macOS. Swift
- sandvault — sandboxing AI agents in isolated macOS accounts, plus the
/svClaude Code skill. Shell - msgvault — offline search and AI query over a lifetime of email and chat, on DuckDB. Go
- a14y — an agent-readability scorecard for the web. JS
I also maintain a fork of eg4_web_monitor with AC couple energy registers over Modbus and Home Assistant sensors for EG4 inverters.
Open-source talks
- VC perspectives on open source funding, with Erica Brescia CNCF
- What open source licensing means for the next generation of OSS businesses — a DevGuild panel I moderated Heavybit
- How breaking production on purpose became chaos engineering YouTube
- Where DevOps came from, and where it goes next InfoQ
- Changing engineering culture from the inside YouTube
- Opening the first Velocity, with Steve Souders YouTube
My take: how open source works as a business strategy.
Selected writing & talks
- GameDay and chaos engineering jesserobbins.com
- Resilience Engineering: Learning to Embrace Failure ACM Queue
- How DevOps actually started jesserobbins.com
- Hacking culture: how change actually spreads in engineering orgs InfoQ
- What I built at Amazon jesserobbins.com
- Why operations became a competitive advantage ThoughtWorks
- Good fences make good agents: sandboxing AI agents Lab