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?
When I was playing my sport, the idea of learning something new — of challenging myself, of putting myself in the position of coming out on top when I feel these pressure moments — was actually when I performed my best. You have to figure it out in the moment. You try to learn as much as you can, and you become a sponge. Sport taught me how to handle those situations.
So when I made the bigger transition, I really enjoyed knowing that I wasn’t great at this one thing. When I had a year and a half off from the game, I took a few courses at Harvard Business School and was never so intimidated in my life. I was intimidated to raise my hand and ask a question, because I didn’t know a lot of the answers. But once I got comfortable not being the smartest one in the room, the fact that I was learning and growing was so fulfilling.
Your answer challenges an assumption that was built into my question. I was thinking of tennis as a space that you’d mastered, but you thought of it as a place of constant challenges, where you learned that you thrive in moments of uncertainty. That’s a powerful thing to know about yourself.
Yeah. As I stepped away from the game, so many friends would tell me, “You’re going to be even more successful in business than you were in your sport.” And I’d say, “How do you know?” It took me over 25 years to get to that level in one sport. A majority of those years were practicing on the back courts where no one was watching, where I had failed so many times, and I was just trying to find my way with different people, with different coaches, with different methods. It’s the only way to get to success.
So when I start this new chapter, there are questions I have to answer myself. Am I being realistic? Do I want to be involved? But I’m intrigued.
I like that feeling of uncertainty.
Whenever people transition from one career to another, they tend to discover skills they had no idea were transferrable. Have you found any others — like, maybe the focus that athletics requires?
It’s an interesting subject. When I opened the gate to a tennis court and I walked in, I was in my zone. No matter how many great or bad things were happening with me or around me, no matter how successful or how down I was, everything went out, and I would just focus on the ball with my team.
There’s nothing quite like that now. So I give myself time — whether going outside and being in nature, or spending an hour doing certain things — to remind myself of my passion and drive and focus. It transitions me into a mindset that I bring into my meetings. I become a clearer thinker. If I get on an investor call, I’m kind, but I’m tough! This is business, and you’re there to get an investment.
You’re pitching investors with the founders you work with, but you’re also an investor yourself. So let’s talk about that from both sides. First, when you go into pitch meetings with founders,