Future Hall of Fame wide receiver Larry Fitzgerald said he always expected to be coached. Just not by a Wall Street banker. So when Frank Bisignano—then a senior JPMorgan Chase & Co. executive and now CEO of Fiserv—pushed a twentysomething Fitzgerald to think about life beyond the National Football League, it changed his trajectory.

That led to a series of internships between football seasons, touching on everything from venture capital to real estate and mezzanine financing. Fitzgerald played football for more than a decade after his run-in with Bisignano, spending his entire pro career with the Arizona Cardinals. But thanks in part to that first internship (at JPMorgan), he’s since invested in more than 160 companies, ranging from tech firms to an Indian cricket team. One of his breakthrough business moments came in 2020, when he joined the board of Dick’s Sporting Goods Inc., a publicly traded retailer that now has a market capitalization of about $16 billion.

Arguably among Fitzgerald’s most interesting deals is one tied to his oldest passion: chess. He started playing as a kid, an effort by his parents to focus a restless young mind. His public affinity for the game led to a meeting with Danny Rensch, the “chief chess officer” of Chess.com. Fitzgerald invested in the company and played in a celebrity tournament. He even allowed Chess.com to create a bot trained on his previous matches.

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