Andy Roddick's Long Game

The retired tennis champ has bounded into angel investing. He's had plenty of wins—and some interesting losses, too.

- BY TOM FOSTER

One night in May 2020, Andy Roddick found himself on a Zoom doing what so many did at the height of the pandemic: catching up with friends, kicking around half-serious ideas, and, in his words, “finding the bottom of a bottle of wine.”

At some point, Roddick asked the group, “What’s getting expedited in your world because of all this?” One friend, an orthopedic surgeon, started explaining how he was diagnosing injuries over FaceTime. Roddick pressed him. Was it actually effective? Yes, the doctor said. He could diagnose 90 percent of his patients remotely with the right motion tests.

The next morning, Roddick called him back, sober this time. Was anyone building a diagnostic tool for remote musculoskeletal care? No. Roddick picked up the phone again, this time to call a tech entrepreneur friend, and ViewFi, a sports medicine telehealth startup, began to take shape.

Roddick retired from tennis more than a decade ago, and since then the former No. 1 player in the world has redefined himself as a founder, investor, podcast host, and philanthropist.

As an angel investor, he has done more than 40 deals, and his eclectic portfolio runs the gamut from real estate to cookie delivery to media to telehealth. Through the Andy Roddick Foundation, he has raised nearly $40 million to fund afterschool activities for low-income kids. The business lessons he’s learned along the way cover a similarly wide range, as he shared recently from his home in Charlotte, North Carolina.