paypal-mafia
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David Sacks
David Sacks is a South African-born Silicon Valley operator turned venture capitalist and political power broker. He was PayPal's first product leader and COO, founded and sold Yammer to Microsoft for $1.2 billion, rescued Zenefits as interim CEO, and co-founded Craft Ventures, which manages billions in assets. He is a co-host of the chart-topping All-In podcast and served as the first White House AI and Crypto Czar in the second Trump administration before stepping aside in March 2026.
Jeremy Stoppelman
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.'
Roelof Botha
Roelof Frederik Botha is a South African-American venture capitalist and former Managing Partner of Sequoia Capital, one of the world's most storied VC firms. Grandson of South African foreign minister Pik Botha, he rose from PayPal CFO at age 28 - overseeing the company's IPO and $1.5B sale to eBay - to become one of Silicon Valley's most celebrated investors. He wrote the original investment memo for YouTube when the company had 3 employees and a valuation of $11.5M; Google bought it 14 months later for $1.65B. Over two decades at Sequoia, he backed YouTube, Instagram, Block (Square), MongoDB, Unity, Natera, and dozens more, generating over $50 billion in returns for limited partners. He stepped down as Sequoia's Senior Steward in November 2025.
Peter Thiel
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
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.
Luke Nosek
Luke Nosek is a Polish-American entrepreneur and venture capitalist who co-founded PayPal, where he served as VP of Marketing and Strategy. He later co-founded Founders Fund with Peter Thiel and Ken Howery, before launching Gigafund in 2017, a venture firm focused on transformative technologies. As the first institutional investor in SpaceX and board member since 2008, Nosek has championed ambitious, decades-long investments in space exploration, AI, and frontier technologies, embodying a contrarian approach to venture capital that prioritizes world-changing impact over short-term returns.
Keith Rabois
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
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
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.
Scott Banister
Scott Banister is a serial entrepreneur and prolific angel investor who co-founded IronPort Systems (acquired by Cisco for $830M), was the first outside investor in PayPal, and is credited by insiders with conceiving the paid keyword search advertising model that spawned the entire Google AdWords ecosystem. With 100+ investments spanning Uber, SpaceX, DeepMind, Facebook, and Affirm - most at seed stage - he is one of the most consequential yet least-known members of the PayPal Mafia.