Nineteen years ago, in a Fortune cover story that christened the group, the so-called “PayPal Mafia” gathered in San Francisco for a photo shoot. There were gold chains, tracksuits, Maker’s Mark, Sinatra singing through the Wurlitzer. Peter Thiel had a butler, Fortune’s Jeffrey O’Brien discovered—“holy cannoli”—while Max Levchin wore mismatched freebie shorts.
Elon Musk skipped the photo shoot to collect an innovator-of-the-year award, but Reid Hoffman, David Sacks, Roelof Botha, Jeremy Stoppelman, Jawed Karim, Chad Hurley—they were all there or thereabouts, having recently sold PayPal to eBay for $1.5 billion and scattered into dozens of enterprises which Fortune valued at the time to be “worth a total of roughly $30 billion.”
That $30 billion valuation now, of course, feels quaint. The mafia went on to build or fund Facebook, LinkedIn, YouTube, Yelp, Tesla, SpaceX, Palantir, Affirm, and a meaningful slice of the venture capital industry that then bankrolled mostly everything else in Silicon Valley. They produced presidents of companies, elevated a sitting Vice President, and one even became the richest man on Earth.
Meanwhile, the company that made their name keeps faltering towards the point of no return.
The company beat expectations in their first quarter 2026 earnings; $8.4 billion in revenue against $8.05 billion expected and an earnings-per-share of $1.34 against $1.27. Still, the market shoved the stock down about 10%, to about $45.50 a share. PayPal’s new CEO Enrique Lores, in his first earnings call, announced a “strategic reorganization” that sounded involved: a new, three-unit operating model and the now-mandatory pledge of “aggressive adoption of AI.”
But it might be too late for AI to save the stock.
PayPal has suffered as they’ve been losing their share to Apple Pay, Google Pay and Shop Pay over the years. Growth, they announced in Q4, decelerated from 6% all the way down to 1% year-over-year last quarter. David Marcus, PayPal’s former president, spoke up for the first time in 12 years in February to say that the company had “lost its mojo.”
Arguably, the mojo left in 2002, when a deal with eBay closed and Thiel walked out the same day. Soon, the group of workaholic introverts who slept under their desks and dropped out of PhD programs to run the company all followed; Sacks, who left to eventually become the “AI czar” for the White House, Hoffman to start Linkedin, Hurley and Karim for Youtube, and Musk for SpaceX and Tesla (He was dramatically pushed out earlier).
They were product people running a product company, and what replaced them, eventually, was finance people who were best at optimizing, and bet on pure volume. PayPal acquired Braintree (whose former CEO, Brian Johnson, is now infamous for his biohacking efforts) in 2013 and built it into a gigantic, unbranded processor behind Uber, Airbnb, and a long list of other companies, whose checkout pages don’t reference PayPal at all. So even as total payment volume kept going up with these partnerships, the brand-name recognition declined, as did what made PayPal unique in the first place.
This is something the former president acknowledged as one of PayPal’s fatal flaws. Marcus wrote on X it was “a fundamental miscalculation” to optimize for payment volume rather than margin and differentiation.
The numbers speak for themselves. PayPal today is worth about $40 billion. The mafia’s other companies are worth dozens of times that—Tesla and Meta alone are each over a trillion; Palantir is around $400 billion, and LinkedIn sold to Microsoft for $26 billion a decade ago.
The 2007 Fortune piece that named the mafia quoted then-COO David Sacks describing what made the company work in the first place. Prestige there, he said, was measured “by how few people there were above you who could prevent you from doing what you wanted to do.”
