Peter Andreas Thiel (born October 11, 1967 in Frankfurt, West Germany) is one of the most consequential and controversial figures in the history of technology and venture capital. A Stanford philosophy graduate and law school alumnus, Thiel co-founded PayPal in 1998, pioneering online digital payments before selling it to eBay for $1.5 billion in 2002. He then made what became arguably the greatest angel investment in tech history — a $500,000 bet on a 19-year-old Mark Zuckerberg's Facebook in 2004 that ultimately returned over $1 billion. In 2003 he co-founded Palantir Technologies (now valued at over $400 billion), and in 2005 he launched Founders Fund, a venture capital firm managing approximately $17 billion that was among the first institutional investors in SpaceX, Palantir, Stripe, Airbnb, and Spotify. Thiel's 2014 book Zero to One became a defining text on startup theory, articulating his core belief that genuine innovation is far more valuable than incremental improvement. A self-described libertarian, Thiel surprised Silicon Valley when he endorsed Donald Trump at the 2016 Republican National Convention. He is also known for secretly funding Hulk Hogan's lawsuit that bankrupted Gawker Media after the outlet outed him as gay. Through the Thiel Fellowship, which awards $250,000 to young people who skip or defer college, he has championed entrepreneurship over credentialism — producing billionaire alumni including Ethereum's Vitalik Buterin and Figma's Dylan Field. As of December 2025, Thiel's net worth is estimated at $27.5 billion.
Oren Zeev is an Israeli-American billionaire venture capitalist and the most successful solo general partner in VC history. Operating entirely alone from Cafe Venetia in Palo Alto - no partners, no office, no employees - he manages $2.5B+ in assets under management across 9 funds. His concentrated, conviction-driven approach has delivered ~100% IRR since 2008, with landmark investments in Navan (TripActions), Tipalti, Houzz, Chegg, and Next Insurance. His $50,000 'relationship check' in Navan's founders before they had even incorporated the company eventually became a $1B+ payday when Navan IPO'd in October 2025.
Keith Rabois is a PayPal Mafia veteran, co-founder of Opendoor, and Managing Director at Khosla Ventures whose career spans law clerk, corporate attorney, political adviser, and now one of Silicon Valley's most prolific — and outspoken — investors. He is the first institutional backer of DoorDash, Affirm, and Faire, made early bets on Stripe, YouTube, and Airbnb, and brought the iBuyer model to residential real estate before moving to Miami and catalyzing one of the biggest tech migration waves in recent memory.