Home Venture Capital Thiel Capital’s Jack Selby on venture investing, luck and being ‘second banana’

Thiel Capital’s Jack Selby on venture investing, luck and being ‘second banana’

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Jack Selby speaking with attendees at the 2019 Arizona Technology Innovation Summit at The Duce in Phoenix, Arizona (Photo: Gage Skidmore)

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. 

Read more: Tech legends Steve Chen and Patrick Grove on regrets, survival and founder-market fit

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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