Jack Selby

Spear’s Review

There has never been a stronger link between billionaires and Hollywood. Most of the time the former tend not to be the ones who are actually on screen, but there could be a few more exceptions to this rule if Jack Selby gets his way. The investor and former PayPal executive has bought the rights to make a film about the so-called ‘PayPal Mafia’ – the network of nascent tech founders who would go on to shape much of modern Silicon Valley.

‘I just want the story to be told properly,’ Selby has said of the project, notionally titled The Founders. A noble sentiment, perhaps, but one that will inevitably prove to be more complicated given the egos involved. Famous ‘Mafia’ members include Peter Thiel, Elon Musk, Reid Hoffman and David Sacks.

This loose fraternity of tech billionaires has provided occasional snippets of juicy gossip over the years – not least in autumn 2000, when Musk was unceremoniously removed from his original perch at PayPal at the behest of Thiel. Things have stepped up a gear recently, thanks to the ultra-polarised climate of the US election.

After the attempted assassination of Donald Trump in July 2024, both Musk and Sacks made public attacks on their fellow ‘Mafia’ member Hoffman, best known as the founder of LinkedIn, insisting that his generous funding to anti-Trump campaigns and lawsuits had contributed to the climate of violence.

With the film understood to be focusing on the earlier parts of the PayPal mafiosi’s careers, this recent spat is likely not to make the final cut. But the vendetta shows the challenges that may lie ahead for Selby, a hedge fund executive turned budding film-maker, in telling the story. He does at least have some commercial success in Hollywood: one of his first productions, an acclaimed independent film called His Three Daughters, was recently bought by Netflix.

That said, Selby doesn’t look to be leaving his day job any time soon. Having co-founded Clarium Capital with Thiel more than 20 years ago, he now runs Thiel’s family office, Thiel Capital, as well as heading up his own venture capital fund, AZ-VC.