Category:The PayPal Mafia
The PayPal Mafia is the name journalists and business writers gave to the founders and early executives of PayPal who left after the company was sold in 2002 and went on to start, fund or run a large share of the companies that followed. It is one of the few employer cohorts with a name that stuck, and this category collects the people it refers to. The roster splits cleanly in two: the 1998 to 2002 founding group, and a later set of chief executives who ran the payments company itself long after the founders had gone.
Background
PayPal was assembled out of two startups. Peter Thiel and Max Levchin founded the cryptography and payments company Confinity in 1998, with Luke Nosek and Ken Howery among the earliest people involved; Elon Musk founded the online bank X.com at around the same time, and the two merged. Thiel ran the combined company as chief executive, Roelof Botha served as chief financial officer and took it public in 2002, and Howery had held the finance role before him. eBay acquired the company later that same year, and the founding group left within a short window of one another.
That last detail is what makes this cohort different from an ordinary employer roster. Most large companies release their alumni gradually, a few at a time, across decades. PayPal released its senior people almost simultaneously, at a moment when they were in their late twenties and early thirties, with liquidity from the sale and existing working relationships with one another. The result was a network that reappeared as co-founders, board members and first-check investors in each other's next companies, which is what the nickname is actually describing.
The term itself is contested in the way most press coinages are. It flattens a fairly wide group of people into a single unit and implies more coordination than a set of overlapping cap tables really involves. It is used here because it is the name the record uses.
The founding cohort
Peter Thiel went from PayPal to being the first outside investor in Facebook in 2004, co-founded the data analytics company Palantir Technologies in 2003, and started the venture firm Founders Fund in 2005. Ken Howery co-founded Founders Fund with him and later entered diplomacy. Max Levchin, the company's chief technology officer, founded the consumer lending company Affirm. Luke Nosek, born in Tarnów, moved into venture investing. Roelof Botha went to Sequoia Capital and served as its managing partner from 2022 to 2025.
David Sacks was chief operating officer and ran product; he founded the enterprise social network Yammer, sold it to Microsoft in 2012, served as interim chief executive of Zenefits during a regulatory crisis, and later advised the federal government on technology policy. Keith Rabois became a managing director at Khosla Ventures. Jeremy Stoppelman left to co-found Yelp in 2004 and has run it ever since. Scott Banister, who had been working in internet marketing and search since the mid-1990s, became an angel investor.
Read as a group, the pattern is investing rather than operating. Of the founding cohort here, more went into venture capital than into running companies, and several did both in sequence. That is the mechanism the nickname points at: not a set of people who built one thing together, but a set of people who kept funding one another afterwards.
The other PayPal roster
A second and quite separate group in this category never overlapped with the first. These are the executives who ran the payments company in its later, public-market life, and their careers move in the opposite direction, out of PayPal and into the chief executive seat at other large listed companies.
Dan Schulman led PayPal for years and now runs Verizon. Alex Chriss succeeded him in September 2023 and served until February 2026, when Enrique Lores moved across from the chief executive role at HP to replace him. Bill Ready left to run Pinterest in 2022. Scott Thompson held senior roles at PayPal and eBay before a brief and contested tenure as chief executive of Yahoo in 2012, which ended over inaccuracies in his stated academic credentials. Carmine Di Sibio went on to serve as global chairman and chief executive of EY from 2019 to 2024.
Keeping these two groups distinct matters for anyone using this category as a research starting point. The founders are a venture capital network. The later executives are a professional management pipeline. They share an employer and almost nothing else, and merging them produces a misleading picture of both.
See also
This category currently contains no pages or media.