The long-time managing director of billionaire entrepreneur Peter Thiel’s family office, Thiel Capital, is also behind Arizona’s largest venture fund, AZ-VC
About seven years ago, the identity of a mysterious diner who made news for leaving generous tips between $1,000 to $5,000 at restaurants was finally revealed. His name was Jack Selby, and he started his anonymous surprises in 2013—four years before he got found out.
If Selby’s name sounds familiar for other reasons, it’s because he is a member of the famous “PayPal mafia”, a group of former founders and early employees of the fintech company who have gone on to start their own successful businesses. Said people include Tesla’s Elon Musk, LinkedIn’s Reid Hoffman, YouTube’s Steve Chen, and billionaire entrepreneur Peter Thiel, with whom Selby continues working closely today.
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In 2002, after PayPal was acquired by eBay, Selby and Thiel co-founded the macro hedge fund Clarium Capital Management. Selby now heads Thiel’s Los Angeles-based family office, Thiel Capital, from his home in Arizona, where he also runs AZ-VC, the venture capital firm he started in 2021.
His $110 million venture fund is currently Arizona’s largest, writing checks between $2 million to $5 million to growth-stage startups.
Outside of investing, Selby has an equally colourful life as an independent producer with credits in films like Memory (2023) starring Jessica Chastain, His Three Daughters (2023) starring Elizabeth Olsen and Bernie (2011) starring Matthew McConaughey. As a student, he attended Hamilton College, a liberal arts school in New York. There, he met Thomas Tull, who would go on to start film production giant Legendary Entertainment. Tull would bring Selby onto several film and documentary projects. In 2014, Selby alongside Duncan Montgomery started the production company, High Frequency Entertainment.
During a private event at the Singapore office of Vertex Ventures Southeast Asia and India, Selby shared pearls of wisdom on his investment journey, approach and perception of the future. Here are some of the key takeaways.
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On how people’s career aspirations have changed
“When I graduated from college in 1996, all my friends wanted to work at Goldman Sachs, be a derivatives trader and [the like]. Today, years after the financial crisis, everybody wants to be an entrepreneur. And I think the societal value of everyone wanting [this] is great because it creates jobs and products.”
But the glamour of entrepreneurship is overblown
“It’s almost become like a game show. It’s like when I get on the escalator, I get off at the top and the confetti and balloons will drop, and I’m going to become a billionaire. I won the game. But that’s not how it works. Being an entrepreneur is not [like being on] an escalator. Some people don’t have the temperament to deal with near-death experiences.”
Although, if you’re in it, you might as well go big
“One of my favourite phrases, which I borrow from a buddy who’s a partner at Greylock [Partners], is you have to have equal parts grit and grandiosity. Grit is obvious. Grandiosity is that if you’re going to go through this crazy amount of work, working 24/7 for multiple years, you might as well be rewarded for it.”
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On when the next PayPal will emerge
“It’s at the bottom of the cycle, when the cycle starts to turn. But it’s also really hard, so people just need to be eyes wide open about the reality.”
