“The app sells itself,” says Sherman, who contacted FleetWit founder David Metz a few months ago to profess his love for the platform, from which he’s won $7,000 competing in categories for movies, sports, music, and Harry Potter. “It allows your wit and mind to be developed, and literally put your money where your mouth is.”

For Sherman, who also dabbles in cryptocurrency and tech stocks, his affiliation with FleetWit is a natural way to diversify his portfolio beyond football.

Indeed, Smart Play: Connecting Startups and Sports, a joint event run by the NFL Players Association and Amazon Launchpad, mixed tech start-ups, venture capitalists, and football players at Amazon.com’s headquarters last year in hopes of some corporate matchmaking. (The NFLPA operates a tech accelerator, called One Team Collective, that trades player licensing rights for equity. It has identified artificial intelligence, blockchain, customer experience, Cybersecurity, and consumer product innovation as five key themes in 2018.)

Sherman, who played football at nearby Stanford University, got early exposure to Silicon Valley, sparking his interest.

“I’ve always been interested in tech,” says Fleener, who plays tight end for the New Orleans Saints. He has investments in a few tech start-ups he declined to name.

“I was impressed with the technology” of SyncThink, Fleener says. “They’re doing important work.”