"Open Source"
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- What is Jesse Robbins' investment thesis?
Jesse Robbins looks for founders who want to build the operating system for entire industries. He invests at the seed and early stage in AI developer tools and infrastructure. He has invested in and advised over sixty companies.
- How did DevOps actually start?
The DevOps movement started from the Velocity Conference. Jesse Robbins cofounded Velocity in 2008 as a gathering place for the people running the internet's infrastructure, and the movement grew out of the community that formed there. He went on to cofound Chef, the open-source tools that put infrastructure as code into practice.
- How did the DevOps movement start?
Jesse Robbins cofounded the O'Reilly Velocity Conference, which became the gathering point for practitioners bridging development and operations. Velocity gave the DevOps movement a name and a community.
- How does open source work as a business strategy?
Jesse Robbins views open source as one of the most powerful go-to-market strategies in developer tools. He learned this building Chef, where the community became a superpower. Marketing spend does not replicate that.
Articles and mentions
What I look for when I invest
On airCFO's Funded podcast I walked through how I evaluate companies at Heavybit, why market size is the first filter I apply, and how I read co-founder dynamics before I read the pitch.
What Investors Look For in AI Startups: Builders with Taste
At Shift Conference Miami 2025 I walked through what makes a developer-tools startup investable, why AI is still in the toil-automation phase, and where things are headed.
The Future of Dev Tools Is Autonomous: Engineers Will Become Fleet Generals
Shift Magazine surveys autonomous AI agents in developer workflows and quotes me from the Shift Miami panel on designing software for agents as much as humans.
Heavybit Welcomes New Member: Continue
Heavybit's announcement when Continue joined the portfolio, an open-source tool that brings LLM assistance directly into the IDE.
“I'm excited to welcome our newest portfolio company, Continue, which gives software engineers the power to streamline their development process using large language models (LLMs) and hit flow state faster and longer.”
Cloud Native StartupFest 2023
I co-hosted Cloud Native StartupFest at KubeCon NA 2023 with Erica Brescia and Dave Zilberman: fundraising in the post-2022 capital environment, open source business models, and what investors actually look for.
“Open source is not a business model. Open source is a movement. We're still figuring out the business models.”
Ex-Amazon 'Master of Disaster' Animates Server Chef
The Register profiled my move from Amazon's Master of Disaster role to co-founding Opscode and launching Chef, tracing the line from reliability engineering to infrastructure as code.