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.[4] 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.[5] They remained connected as social and business acquaintances,[5] 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.[4] The term[6] 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.[7]
Members
People the media calls members of the PayPal Mafia include:[8][6]
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.[15]
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.
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.[18]
Premal Shah, former product manager at PayPal who became the founding president of Kiva.org. Serves on the Change.org board.
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.[19]
Yu Pan was one of the co-founders of PayPal and played a role in designing the company's user interface and user experience.[20] 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.[21] 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.[4] They are discussed in journalist Sarah Lacy's book Once You're Lucky, Twice You're Good.[22] According to Lacy, the selection process and technical learning at PayPal played a role, but the main factor behind their success was the confidence they gained there. Their success has been attributed to their youth; the physical, cultural, and economic infrastructure of Silicon Valley; and the diversity of their skill sets.[4] PayPal's founders encouraged tight social bonds among its employees, and many of them continued to trust and support one another after leaving PayPal.[4] An intensely competitive environment and a shared struggle to keep the company solvent despite many setbacks also contributed to a strong and lasting camaraderie among former employees.[4][23]
Politics
Some members of the group, such as Thiel, Sacks, and Musk, later expressed libertarian and conservative political views.[24] By contrast, Hoffman has been a top donor to many Democratic Party campaigns and political efforts.[25]
12"Max Levchin: The Making of a Tech Mogul". Grainger College of Engineering. University of Illinois Urbana-Champaign. May 17, 2018. Retrieved October 1, 2025. 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.
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