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The “PayPal Mafia” is teaming up once again at Peter Thiel’s Founders Fund

More turnover in the upper ranks of an industry that has had a ton recently.

Khosla Ventures partner Keith Rabois.
Khosla Ventures partner Keith Rabois.
Steve Jennings / Getty Images for TechCrunch

Keith Rabois — one of the more prominent investors in Silicon Valley, and a close friend of Peter Thiel’s since they were a pair of controversial conservatives together as undergrads at Stanford — is teaming up again with his old friend.

Rabois is joining Thiel’s venture capital firm, Founders Fund, as its newest general partner. It’s a major addition for the VC firm, which is a top performer but has seen a coincidentally high number of departures from its upper ranks in recent years. In fact, the entire venture industry has seen a ton of turnover recently.

Rabois and Thiel are also two of the industry’s most prominent political conservatives. Thiel’s support for Donald Trump in 2016 became a flashpoint in the debate over the last few years about the relationship between Silicon Valley and the Republican Party.

Rabois — even at his old firm, Khosla Ventures — has always been a part of the extended Thiel orbit, but this move has a bit of “getting the band back together” about it. He told Recode it was the “most professionally difficult decision I’ve ever made in my life.”

“It moved from something that was a 5 to 10 percent probability to something that became real over the last couple of weeks,” Rabois told Recode. “I’ve learned more from Peter than anybody else in my career, and I probably quote something from Peter every single week of my life.”

Here’s Thiel: “Keith is a great investor, a successful founder, and an extremely talented operating executive. Any one of those is hard to pull off; Keith has mastered all three. If you’re a founder, he’s exactly who you want on your side.”

Unafraid to mix it up on Twitter — where he has become one of the industry’s loudest and most interesting voices — Rabois has had a colorful past: At Khosla since 2013, he was previously the chief operating officer at Jack Dorsey’s payments company, Square, but left following a sexual harassment claim from a coworker. (Rabois denied any wrongdoing.) He previously held senior roles at LinkedIn and PayPal, working alongside Thiel in what would later be known as the PayPal Mafia.

The news was first reported by Axios.

Here’s Rabois’s recent interview on an episode of Recode Decode.

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