NAT FRIEDMAN

Started programming at age 5. Co-founded Ximian in 1999, which built Linux desktop tools — acquired by Novell in 2003.

Became CTO of Xamarin, which was acquired by Microsoft in 2016. Microsoft appointed him CEO of GitHub after the $7.5 billion acquisition in 2018.

Under his leadership, GitHub grew from 31 million to 73 million developers and launched GitHub Copilot — the first mainstream AI coding assistant. Left GitHub in 2021 to focus on investing.

Co-founded AI Grant with Daniel Gross in 2017 — a grant program for open-source AI research that has funded hundreds of projects. Has personally invested in over 100 startups, heavily concentrated in AI, developer tools, and open-source software.

Investors in companies including Exa AI, Perplexity AI, and numerous other AI startups. Known for being incredibly fast at evaluating companies — reportedly makes investment decisions in under 24 hours.

AI Grant (co-founder), GitHub (former CEO), Ximian (co-founder), angel investor in 100+ startups

Velocity investing. Friedman makes investment decisions faster than almost anyone in Silicon Valley — often within hours of meeting a founder.

His thesis: AI will reshape every industry, and the best AI companies will be built by technical founders who ship fast. He prefers companies building infrastructure and tools over applications.

His investments are concentrated in AI and developer tools because those are the domains he knows deeply.

GitHub Copilot. As CEO, Friedman championed the development of AI-powered coding assistance before most people took the idea seriously.

Copilot became GitHub's fastest-growing feature and proved that LLMs could write production code. His angel portfolio is too early to fully evaluate, but investments in companies like Perplexity AI have already shown strong returns.

The opportunity cost of leaving GitHub. As CEO of a platform with 73 million developers, Friedman had enormous influence and a compensation package to match.

Walking away meant leaving guaranteed income for uncertain angel returns. Some of his 100+ investments will inevitably go to zero.

But Friedman explicitly chose optionality over security.

Ship fast, evaluate fast, decide fast. Friedman believes that speed is the most underrated quality in both founders and investors.

"The best founders are the ones who ship something in the first week, not the ones who spend three months on a business plan." He applies the same urgency to investing — slow decision-making kills more deals than bad judgment.

Keeps personal life private. Known for his close collaboration with Daniel Gross — their AI Grant partnership has become one of the most influential funding vehicles in AI research.

MIT (studied computer science). Started open-source software development while still in college.

His technical depth is genuine — he can evaluate AI architecture at the code level, which gives him an edge over non-technical investors.

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