Venture capitalist and member of the legendary PayPal Mafia. After PayPal he became COO of Yammer, which was later acquired by Microsoft. He invested early in companies such as Airbnb, Slack, and Twitter. Known for pointed political commentary: conservative, libertarian, and often provocative.

Since January 2025 he has served as AI & Crypto Czar in the Trump administration, a newly created role intended to coordinate the U.S. regulatory approach to AI and cryptocurrencies.

He is also one of the hosts of the All In Podcast.