Maria Sharapova’s Superpower

“The one thing that you build as an athlete is a lot of confidence, and with confidence, it very easily can turn into ego,” Ms. Sharapova said. “Then it becomes really difficult to ask questions and acknowledge that you are not an expert. But you can never lose sight of the fact that something that you are so deeply great at will come to an end, and sometimes that means failing in other things to figure out what else you are passionate about.”

A brief flirtation with designing a collection for Cole Haan in 2009 taught her that. When she told Ms. Wintour about it, she said, Ms. Wintour raised an eyebrow and told her she’d better be sure about it because “you only get one chance.”

“People questioned whether I had the authority to lean into design in that way,” Ms. Sharapova said. “I had the one platform, which was tennis, and it wasn’t clear people thought I could do anything else. But a little competitive voice in me said, ‘Well, let me show you.’ I like leaning into the pressure. If you don’t feel that there’s something on the line, then what are you working toward?”

The Scariest Choice

When Ms. Sharapova was a Tiffany ambassador, she got to meet Frank Gehry, who taught her something about perspective. She recalled that they were talking about a jewelry collaboration he did with the company. “He’s like: ‘You know that Tiffany collection I did? They say they are hearts, but I look at them, and I’m thinking they might be butts.’”

She had started a candy brand, Sugarpova, in 2012, but closed it in 2021. Since then, she has largely focused on being an investor and strategic adviser to companies that sell consumer products, especially in the wellness space. She currently has a portfolio of about 11, including Cofertility, an egg-sharing fertility company; Therabody, the company that makes Theragun massage tools; and Supergoop, the skin-care line.

Of all her post-tennis pursuits, the one that scared her most was joining the Moncler board. “I was really hesitant to take that role,” she said — and not because Moncler is a winter sports brand. “It was very intimidating,” she said. “You’re sitting in a room, navigating a billion-dollar public company in real time. During meetings, there are proper microphones with an interpreter, and in order to speak, you have to press a button. It’s not like: ‘Oh, hey, here’s my thought. I have an opinion.’”

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