Maria Sharapova's Winning Secret: 'I Hired People I Could Lose With' The tennis star and entrepreneur explains what it's like to start over professionally and what she looks for in a pitch deck.

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."

Related: Maria Sharapova Built a Business Empire Thanks to Her Winning Team

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.

Related: 5 Steps to Hiring the Right People for Your Business

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,
what have you seen be a difference-maker?

Even if you have a fantastic-looking deck and great numbers, and you're the best of the best on paper, the investors know it's not all perfect. I've been on calls where founders are honest about their disadvantages and some of the qualities they're lacking, and it's almost like they're doing the investors' homework for them. It builds an initial trust. That's important in every type of relationship, personally and professionally.

That's a scary leap of faith — the idea that sharing weaknesses can actually be an asset.

I guess there's a right amount of everything. If your company is particularly strong, you could share your own personal stories of challenges you faced. It's a way to be more personable, more human.

I have a very good understanding of losing and winning, and the feelings that come with that, and doing it in front of hundreds and thousands of eyeballs, and having to face up to it — getting up on the podium and saying, "Today was a tough day, and this is what happened, and this is what I'm going to do to overcome it." There's something valuable about sharing your own personal journey.

Related: 6 Steps for Hiring the Right People to Build Effective Teams

When entrepreneurs pitch you for an investment or a partnership, what catches your interest? And what doesn't?

I feel like presentations and decks are becoming longer and longer. By the time I'm on page 15, I'm like, I don't even know what this business is! Clean, crisp, and short is preferable. But also, I love hearing someone's authentic human story. Don't start with the business. Because when challenges come — which they will — it's not about the business; it's about the person who's handling it.

In my sport, I hired people I could lose with — who I'd be comfortable losing with — because they're who would give me the best support. I mean, they took the losses hard. You want them to take them hard because you want them to be competitive. But if they're people you'd want to be with when you lose, then I'm sure you'll be able to celebrate well with them.

That's powerful to hear, because I would imagine that if somebody has a limited amount of time to pitch someone like you, they might think, Well, she doesn't care about me; she cares about the opportunity, so I'll skip straight to that. But you're saying that's a mistake.

Yeah, absolutely. It's not just about business or dollars.