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Fortune

Eva Roytburg

The 'PayPal Mafia' built a $1.5 billion fintech pioneer. The company they left behind is struggling

PayPal Fortune David Sacks David Marcus Elon Musk Jawed Karim LinkedIn Peter Thiel Reid Hoffman Tesla Inc.

(Credit: Robyn Twomey for Fortune)

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.”

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