Jeremy Stoppelman is the co-founder and CEO of Yelp, the local reviews platform he built after getting the flu in 2004 and being unable to find a doctor online. A PayPal Mafia veteran who rose to VP of Engineering before dropping out of Harvard Business School, Stoppelman turned a $1M seed check from Max Levchin into a public company with 308 million reviews and $1.4 billion in annual revenue. He has spent two decades fighting Google's search monopoly, championing remote work and YIMBY housing policy, and writing Yelp reviews under the username 'Big Papa.'
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.
Jawed Karim is the co-founder of YouTube and the man behind the internet's most historically significant 19 seconds of footage — 'Me at the zoo,' uploaded on April 23, 2005. Born in East Germany to a Bangladeshi father and German mother, Karim built YouTube's anti-fraud infrastructure at PayPal alongside Chad Hurley and Steve Chen before pivoting to change how humanity watches video. After Google acquired YouTube for $1.65 billion in 2006, Karim quietly enrolled at Stanford, co-founded early-stage fund Y Ventures, and became one of Airbnb's first investors. He communicates publicly almost exclusively through the description box of his single YouTube video.
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.
Reid Hoffman co-founded LinkedIn, helped build PayPal, seeded Facebook, and has been quietly central to almost every major tech breakout of the last 25 years. A philosopher-turned-venture-capitalist who popularized 'blitzscaling,' he is now betting big on AI — co-founding Inflection AI, launching Manas AI for drug discovery, hosting two podcasts, and writing bestsellers with GPT-4 as co-author.
Max Levchin is a Ukrainian-American tech entrepreneur and co-founder of PayPal, where he served as CTO and helped build one of the world's first large-scale digital payment systems. He later founded Slide (acquired by Google for $182M), Glow (women's health app, 25M users), and most prominently Affirm - the publicly traded buy-now-pay-later leader with $3.22B in FY2025 revenue. Levchin is also a cryptography advocate (creator of the Levchin Prize), early Yelp investor and chairman, and co-founder of SciFi VC with his wife Nellie.