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

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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