In 2007, Fortune journal reimagined a traditional mafia scene with a Silicon Valley twist: 13 male founders and early staff of PayPal, all lengthy gone from the corporate, posed at a San Francisco café with slicked-back hair, poker chips and dozens of whiskey glasses. The group included a few of the most recognizable names in at present’s tech scene, like Elon Musk, Peter Thiel and Reid Hoffman. The journal dubbed them the “PayPal mafia,” not for his or her time on the fintech firm, however for his or her outsized impression on Silicon Valley by means of the businesses they launched afterward.
PayPal went public in early 2002 and was acquired by eBay for $1.5 billion the identical 12 months. Most of its early staff left the corporate after the acquisition. They went on to discovered YouTube, SpaceX and LinkedIn, amongst different legendary names in Silicon Valley. Nevertheless, like their cinematic namesake, the group hasn’t prevented controversy. These former colleagues have constructed billion-dollar companies whereas additionally discovering themselves within the crosshairs of public criticism.
As an illustration, Thiel has confronted controversy over his political affiliations and, most notably, for funding Hulk Hogan’s 2012 lawsuit in opposition to Gawker Media with $10 million — a case that in the end drove the web media firm out of business. Musk has additionally confronted criticism for his takeover of Twitter and his prior position within the Trump administration, the place he led widespread federal worker firings.
Right here’s what they’re as much as lately:
Peter Thiel: enterprise capitalist
Peter Thiel, Max Levchin and Luke Nosek based PayPal in 1998, initially as a software program safety firm. After merging with Elon Musk’s X.com (unrelated to the social media platform he owns at present), PayPal shifted its focus to digital funds.
Thiel served as CEO from 1998 till 2002, leaving after the corporate was bought to eBay. He then co-founded Palantir Applied sciences, a serious U.S. authorities contractor offering knowledge analytics providers. The corporate now has a market capitalization of $439 billion.
Thiel is often known as a prolific angel investor. He co-founded Clarium Capital, Founders Fund, Valar Ventures and Mithril Capital. In 2004, Thiel grew to become Fb’s first exterior investor after buying a ten.2 % stake within the firm for $500,000.
Thiel is among the many many former PayPal staff who’ve entered political and high-profile public arenas. An lively donor to the Republican Celebration, Thiel supported Donald Trump’s 2016 presidential marketing campaign however withheld donations through the 2024 election. He’s additionally credited with serving to JD Vance attain the Vice Presidential ticket.
Elon Musk: entrepreneur, the world’s richest particular person
Elon Musk briefly served as PayPal’s CEO earlier than being ousted by the board in 2000. He went on to construct some of the influential portfolios in know-how, spanning electrical automobiles, house exploration, social media and A.I.
Musk based SpaceX in 2002 and has led Tesla since 2008. He additionally based Neuralink and The Boring Firm, increasing his attain into brain-computer interfaces and infrastructure. In 2022, Musk gained world consideration for buying Twitter for $44 billion, later rebranding it as X.
His ties to A.I. run deep: Musk co-founded OpenAI with Sam Altman in 2015 however left in 2018 over strategic disagreements. In 2023, he returned to the sphere by launching xAI, a analysis enterprise targeted on constructing A.I. that’s extra comprehensible for people.
At present, Musk is the richest particular person on this planet, with an estimated web price of $400 billion. He’s additionally maybe the one PayPal alumnus to ascend into direct political affect. In the course of the Trump administration, he led the Division of Authorities Effectivity (DOGE)—a reputation shared together with his cryptocurrency enterprise—earlier than stepping down in Might after clashing publicly with the President.
Max Levchin: pc scientist
- Place at PayPal: co-founder, chief know-how officer from 1998 to 2002
- Corporations later based: Affirm
- Web price: $1.8 billion
As PayPal’s chief know-how officer, Max Levchin helped lead the corporate’s anti-fraud efforts by co-creating the Gausebeck-Levchin check—the inspiration for the broadly used CAPTCHA safety software. After leaving PayPal, he launched the media-sharing platform Slide in 2004, which was acquired by Google in 2010. Levchin briefly served as Google’s vp of engineering till Slide was shut down the next 12 months.
In 2012, he co-founded Affirm, a number one “purchase now, pay later” (BNPL) firm, the place he continues to function CEO. At present, Affirm has a market capitalization of $27.5 billion, with 21.9 million customers and greater than 350,000 service provider companions on its platform.
Levchin has additionally held board positions at Yahoo and Yelp. In 2015, he grew to become the primary Silicon Valley govt appointed to the U.S. Client Monetary Safety Bureau’s advisory board, emphasizing the significance of collaboration between corporations and regulators.
Reid Hoffman: entrepreneur, investor
- Place at PayPal: chief working officer
- Corporations later based: LinkedIn, Greylock Companions
- Web price: $2.5 billion
Earlier than becoming a member of PayPal, Hoffman labored as a senior person expertise architect at Apple, contributing to the corporate’s on-line social community eWorld. He later grew to become director of product administration at Fujitsu. After his on-line relationship startup, SocialNet, folded, Hoffman joined PayPal in 2000 as chief working officer.
In 2003, he co-founded the profession networking website LinkedIn. Following Microsoft’s $26.2 billion acquisition of LinkedIn in 2017, Hoffman joined Microsoft’s board, a transfer that drastically elevated his wealth.
Through the years, Hoffman has served on the boards of Airbnb and OpenAI, the place he was additionally an early investor. By way of the enterprise capital agency Greylock Companions, he has backed dozens of A.I. startups. In 2022, he co-founded Inflection AI with Mustafa Suleyman, who now serves as CEO. Earlier this 12 months, he teamed up with most cancers researcher Siddhartha Mukherjee to launch Manas AI, a startup targeted on drug discovery.
David Sacks: investor, White Home A.I. and Crypto Czar
- Place at PayPal: chief working officer from 1999 to 2002
- Corporations later based: Craft Ventures
- Web price: $200 million
Since leaving PayPal, David Sacks has constructed a profession spanning movie, tech, investing and politics. In 2005, he produced and financed a political satire that earned two Golden Globe nominations. The next 12 months, he based Geni.com, a genealogy-focused social community that later spun off Yammer, one of many earliest enterprise social networking platforms. He went on to co-found Craft Ventures, the startup Glue, and the podcast platform Callin.
At present, Sacks serves because the White Home’s Particular Advisor for A.I. and Crypto, a task created by the Trump administration to information coverage on synthetic intelligence and cryptocurrency.
Jeremy Stoppelman: engineer, Yelp CEO
- Place at PayPal: vp of engineering
- Corporations later based: Yelp
- Web price: $100 million
Jeremy Stoppelman joined Musk’s X.com in 1999 and have become vp of engineering after its transition to PayPal. In 2004, he co-founded Yelp, the place he has served as CEO ever since. Below his management, the corporate turned down a 2010 acquisition provide from Google and went public two years later. Stoppelman’s web price is estimated at greater than $100 million.
Ken Howery: investor, U.S. ambassador
- Place at PayPal: chief monetary officer from 1998 to 2002
- Corporations later based: Founders Fund
- Web price: estimated $1.5 billion
Ken Howery served as PayPal’s chief monetary officer from 1998 to 2002. After PayPal’s sale to eBay, he grew to become eBay’s director of company growth till 2003. He later joined Peter Thiel at Clarium Capital as vp of personal fairness and went on to co-found Founders Fund as a companion. Past investing, he’s a member of the Explorers Membership, a nonprofit devoted to scientific exploration, and an advisor to Kiva, the micro-lending nonprofit based by former PayPal colleague Premal Shah.
Howery can be among the many former PayPal executives who’ve moved into politics. He has donated a minimum of $1 million to Donald Trump’s marketing campaign by means of Elon Musk’s political motion committee. Throughout Trump’s first time period, Howery was appointed U.S. ambassador to Sweden and at present serves because the U.S. ambassador to Denmark.
Roeloth Botha: enterprise capitalist
Roelof Botha joined PayPal as director of company growth shortly earlier than graduating from Stanford College. He later grew to become vp of finance and went on to function chief monetary officer till the corporate’s acquisition by eBay.
After leaving PayPal, Botha joined Sequoia Capital, the place he oversaw investments in YouTube and Instagram. He at the moment sits on the boards of MongoDB, Evernote, Chook, Natera, Sq., Unity and Xoom.
Russel Simmons: entrepreneur
- Place at PayPal: software program architect from 1998 to 2003
- Corporations later based: Yelp, Learnirvana
Russel Simmons helped design PayPal’s fee system as a software program architect. After leaving the corporate, he and fellow PayPal alum Jeremy Stoppelman got down to construct a platform for restaurant opinions. With a $1 million funding from Max Levchin, they launched Yelp in July 2004. Simmons served as chief know-how officer till his departure in 2010. On the time, Yelp stated he would stay a “important” shareholder, although the dimensions of his stake—and whether or not he nonetheless holds it—stays unclear.
In 2014, Simmons co-founded Learnirvana, an internet studying platform.
Andrew McCormack: entrepreneur
- Place at PayPal: assistant to Thiel from July 2001 to November 2002
- Corporations later based: Valar Ventures
Andrew McCormack started his profession as an assistant to Peter Thiel at PayPal and adopted him into subsequent ventures. From November 2002 to April 2003, he oversaw operations at Thiel’s hedge fund, Clarium Capital.
In 2010, McCormack co-founded Valar Ventures with Thiel and James Fitzgerald, specializing in fintech investments. He stays a normal companion on the agency.
Luke Nosek: investor
- Place at PayPal: co-founder and vp of selling and technique from 1998 to 2002
- Corporations later based: Founders Fund, Gigafund
In 2005, Luke Nosek joined Peter Thiel and Ken Howery to launch Founders Fund, a San Francisco–primarily based enterprise capital agency that has backed corporations corresponding to Airbnb, Lyft and SpaceX. Whereas his actual web price is unclear, Nosek has made substantial investments by means of his enterprise corporations. At Founders Fund, he led one of many agency’s earliest main offers with a $20 million funding in SpaceX, later serving on its board.
In 2017, Nosek left to co-found Gigafund, which went on to take a position $1 billion in SpaceX, in line with the corporate. He additionally sits on the board of ResearchGate.
Premal Shah: entrepreneur
- Place at Paypal: product supervisor
- Corporations later based: Kiva
Three years after leaving PayPal, Premal Shah co-founded Kiva, a nonprofit that gives loans to entrepreneurs in underserved communities worldwide. He additionally serves on the boards of different nonprofits, together with the Heart for Humane Know-how, the Change.org Basis, Watsi and VolunteerMatch.
Keith Rabois: investor
- Place at PayPal: govt vp of enterprise growth
After leaving his govt position at PayPal, Keith Rabois grew to become an lively investor, backing corporations together with Slide, YouTube and Palantir. He additionally invested in LinkedIn, the place he served as vp of enterprise and company growth, and Sq., the place he was chief working officer.
Rabois joined enterprise capital agency Khosla Ventures from 2013 to 2019 and was a companion at Founders Fund from 2019 to 2024.
