PayPal Mafia

History

Originally, PayPal was a money-transfer service offered by a company called Confinity, which merged with X.com in 1999. X.com was renamed PayPal and purchased by eBay in 2002. PayPal's employees had difficulty adjusting to eBay's more traditional corporate culture, and within four years all but 12 of the first 50 employees had left. They remained connected as social and business acquaintances,{{cite web |title=Max Levchin: The Making of a Tech Mogul |url=https://grainger.illinois.edu/news/features/making-of-max-levchin |website=Grainger College of Engineering |publisher=University of Illinois Urbana-Champaign |date=17 May 2018 |access-date=1 October 2025 |quote=Within four years, all but 12 of the original 50 PayPal employees had left. Levchin and his colleagues remain connected as social and business acquaintances, and a number of them worked together to form new companies in subsequent years.}} and several of them worked together to form new companies and venture firms. This group of PayPal alumni became so prolific that the term PayPal Mafia was coined. The term gained even wider exposure when a 2007 Fortune magazine article featured the group, along with a now-iconic photograph of its members dressed in mafia-style attire, highlighting their influence in Silicon Valley and their role in founding or investing in major technology companies.

Members

People the media calls members of the PayPal Mafia include:

• Peter Thiel, PayPal founder and former CEO. Sometimes called the "don" of the PayPal Mafia, he is a founder of Palantir and chairs its board, a founder of Founders Fund, and the first outside investor in Facebook. In 2025, Thiel and Palantir began collaborating with the Department of Government Efficiency (DOGE) for the second Trump administration.
• Elon Musk, co-founder of Zip2 and founder of X.com (which merged with Confinity to form PayPal), SpaceX, OpenAI, Neuralink, and The Boring Company. He bought a controlling share in Tesla Motors and purchased Twitter (rebranded as X). As of October 2025, he is the wealthiest person on Earth, with a net worth of $750 billion. In 2025, he was a senior advisor to President Donald Trump and head of the Department of Government Efficiency (DOGE).
• David O. Sacks, former PayPal COO who later founded Geni.com and Yammer. In December 2024, President Trump named Sacks the White House AI and crypto czar for the incoming administration.
• Max Levchin, founder and chief technology officer at PayPal, CEO of Affirm, and co-founder of Glow.
• Scott Banister, early advisor and board member at PayPal.
• Roelof Botha, former PayPal CFO who became a partner at the venture capital firm Sequoia Capital.
• Steve Chen, former PayPal engineer who co-founded YouTube.
• Reid Hoffman, former executive vice president who founded LinkedIn and was an early investor in Facebook and Aviary. He sits on the board of Microsoft.
• Ken Howery, former PayPal CFO who became a partner at Founders Fund and served as the US ambassador to Sweden during the first Trump administration and US ambassador to Denmark during the second Trump administration.
• Chad Hurley, former PayPal web designer who co-founded YouTube.
• Eric M. Jackson, who wrote the book The PayPal Wars, became chief executive officer of WND Books, and co-founded CapLinked.
• Jawed Karim, former PayPal engineer who co-founded YouTube. Founder of YVentures.
• Dave McClure, former PayPal marketing director who co-founded 500 Global and became a super angel investor for startup companies.
• Andrew McCormack, founding partner at Valar Ventures.
• Luke Nosek, PayPal co-founder and former vice president of marketing and strategy who became a partner at Founders Fund.
• Keith Rabois, former executive at PayPal who later worked at LinkedIn, Square, Khosla Ventures, and Founders Fund.
• Jack Selby, former vice president of corporate and international development at PayPal who co-founded Clarium Capital with Peter Thiel and is the founder of AZ-VC (formerly invisionAZ Fund), which focuses on Arizona.
• Premal Shah, former product manager at PayPal who became the founding president of Kiva.org. Serves on the Change.org board.
• Russel Simmons, former PayPal engineer who co-founded Yelp.
• Jeremy Stoppelman, former vice president of technology at PayPal who co-founded Yelp.
• Yishan Wong, former engineering manager at PayPal who later worked at Facebook, became the CEO of Reddit, and founded Terraformation Inc.
• Yu Pan was one of the co-founders of PayPal and played a role in designing the company's user interface and user experience. He later became involved in YouTube and co-founded Kiwi Crate, Inc.

Legacy

The PayPal Mafia is sometimes credited with inspiring the reemergence of consumer-focused Internet companies after the dot-com bust of 2001. The PayPal Mafia phenomenon has been compared to the founding of Intel in the late 1960s by engineers who had earlier founded Fairchild Semiconductor after leaving Shockley Semiconductor.

Politics

Some members of the group, such as Thiel, Sacks, and Musk, later expressed libertarian and conservative political views. By contrast, Hoffman has been a top donor to many Democratic Party campaigns and political efforts.

After the 2024 United States presidential election, The Economist wrote that ⁣⁣the PayPal Mafia would "take over America's government" with Trump's reelection. Thiel protégé JD Vance is Trump's Vice President, Musk became head of the new Department of Government Efficiency (DOGE), and Sacks became Trump's advisor on AI and cryptocurrencies. Musk alone donated over $250 million to Trump's 2024 campaign.

References

References

1. (August 2, 2013). "David Sacks". [[Dow Jones & Company]].
2. Harris, Scott Duke. (October 22, 2009). "Scott: PayPal finally poised to enter Web 2.0". [[Bay Area News Group]].
3. (January 26, 2025). "How the roots of the 'PayPal mafia' extend to apartheid South Africa".
4. Helft, Miguel. (October 17, 2006). "It Pays to Have Pals in Silicon Valley". [[The New York Times]].
5. O'Brien, Jeffrey M.. (November 26, 2007). "The PayPal Mafia". [[Fortune (magazine).
6. https://www.generalist.com/p/founders-fund-1
7. Soni, Jimmy. (2022). "The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley". [[Simon & Schuster]].
8. (11 April 2025). "Palantir Is Helping DOGE With a Massive IRS Data Project".
9. Durot, Matt. "Elon Musk Just Became The First Person Ever Worth $500 Billion".
10. (6 December 2024). "Trump Names David Sacks as White House AI and Crypto Czar".
11. (April 1, 2015). "The PayPal Mafia's Golden Touch". [[The New York Times]].
12. (17 November 2022). "Jack Selby of Thiel Capital is using a new VC fund to invest in Arizona startups". TechCrunch.
13. Banks, Marcus. (May 16, 2008). "Nonfiction review: 'Once You're Lucky'". [[Hearst Communications]].
14. Tweney, Dylan. (November 15, 2007). "How PayPal Gave Rise to a Silicon Valley 'Mafia'". [[Condé Nast]].
15. Silverman, Jacob. (October 18, 2022). "The Quiet Political Rise of David Sacks, Silicon Valley's Prophet of Urban Doom".
16. Schleifer, Theodore. (November 27, 2024). "What's a Democratic Billionaire to Do Now?". [[The New York Times]].
17. (December 10, 2024). "The PayPal Mafia is taking over America's government". [[The Economist]].
18. (November 13, 2024). "Elon Musk and Vivek Ramaswamy will lead new 'Department of Government Efficiency' in Trump administration".
19. Canon, Gabrielle. (December 5, 2024). "Trump picks venture capitalist David Sacks as AI and crypto 'czar'". [[The Guardian]].
20. Lim, Clarissa-Jan. (December 6, 2024). "Here's how much money Elon Musk spent to help Trump win the election".