“I Hired People I Could Lose With”

Maria Sharapova’sapproach to business and sports is the same: Losing leads to winning.

- JASON FEIFER

When Maria Sharapova was a global tennis star, she was bombarded with new fitness gadgets, trackers, monitors, and more. “I was like a guinea pig,” she says. She took advantage by trying as many as she could. When she retired from the game in February 2020, she wanted to help promising startups build the next generation of those tools—and due to the pandemic, that work began mostly over Zoom. “I got in front of my computer and tried to meet as many founders as I could,” she says. “I wanted to listen to their stories, hear about their inventions, and see how and where I could help.”

While she intimately understood the fitness world and had brand-building experience through her premium candy company, Sugarpova, she was less practiced as an investor and a strategic adviser— which excited her. After all, tennis taught her that while preparation is important, some things can only be learned by doing. “I think it’s OK, and absolutely human, to know your strengths and weaknesses,” she says. “Ask questions and understand that you don’t know everything.” Today her portfolio includes Bala (which she invested in during a guest appearance on Shark Tank), Tonal, The Skills, Naked Retail, and Therabody. Here, she discusses the power of adversity, and what an investor like her really wants.

Entrepreneurs often put themselves in situations in which they have no history or mastery, and now you’re doing that, too. What has the transition been like?