Centre court tricks for the boardroom

MARIA SHARAPOVA: I think handling disappointment and the emotions are quite similar. Business, it’s more mental than physical, but you give so much for an outcome that wasn’t up to your standards, and so, that’s really deflating. I feel like I have a good understanding of investing your time into something that has no guarantees of results. You can put in hours and hours. You can have all the talent, but until you get there and you do it, no one’s giving it to you.

BOB SAFIAN: That’s Maria Sharapova, the iconic women’s tennis champion, five time Grand Slam winner, and the world’s highest paid female athlete for a decade. Since hanging up her rackets, Maria has leaned into business as an investor, an entrepreneur, and as host of a new podcast appropriately named, Pretty Tough. Sports analogies are rampant in business, but I wanted to hear from Maria firsthand about how the mix of both intense planning and instinctive reaction that’s essential to success on the court translates in today’s chaotic and unpredictable business environment. Maria takes us inside her on-the-job business training and shares where sport and business really do collide right now, and where they don’t. It’s a fun back and forth, so let’s get to it. I’m Bob Safian, and this is Rapid Response.

[THEME MUSIC]

I’m Bob Safian. I’m here with Maria Sharapova. Maria, great to chat with you.

SHARAPOVA: Thanks for having me on. I’m a huge fan of your work.

SAFIAN: Well, so first of all, I want to welcome you to the community of podcast hosts. I understand you’re launching your own show, “Pretty Tough,” conversations with high achieving women in all fields. Are you excited? Are you nervous? Do you get nervous?

SHARAPOVA: Definitely. I get nervous. Yes. I’ve been working on the concept of “Pretty Tough.” It’s been several years since I left the sport of tennis, traveled a little bit, had a son who’s 3 1/2 now, and slowly have been working on this concept around the meaning of a pretty tough woman, playing into duality of being gritty and strong and persevering, but also having a side that is soft, that is motherly, and allowing women to be both without putting a filter on it.

SAFIAN: The end of the Ice Queen, I’m sure you’d love that label.

SHARAPOVA: I played into it pretty well with that fist pump.

Copy LinkThe business of professional tennis

SAFIAN: It’s true. Well, listen, one of the reasons I wanted to talk with you, many successful celebrities, athletes, actors, musicians, they don’t want to talk about the business of themselves, of their brand. They want to talk about their craft or their art, but it’s very much a business too. Did you always get that?

SHARAPOVA: Well, sport is a business. Walking through the tunnel of the US Open, the door opens and that is your platform. That’s win or lose. The check gets bigger, the check gets smaller. The more you win, the more opportunities you have to say yes. There’s also amazing lessons because the more chances you get to say no, the better opportunities come about. But I don’t think I realized it. I moved to the States as a young girl. I don’t think I really acknowledged the full picture, the 360 approach to being an athlete. I had my head down. I had horseblinders on for a majority of my career where all that mattered was the ball and the result. I was, from the moment I woke up.

But I also, as I started making a little money and recognized that, okay, now I’m supported. My family’s supported. My team is supported. I can hire a physio now. Maybe now I don’t need that immediate check. Maybe I can actually invest in a company that perhaps 3, 5, 10 years down the line, I’ll see something in return. The mindset shifts.

SAFIAN: You were so young when you first had success even. You won Wimbledon in 2004, first of 5 Grand Slams. You were 17. At that point, do you remember how strategic you were about brand alignment? Were you even making the decisions?

SHARAPOVA: I was from the first day. After that victory, I remember getting out of the car to the Wimbledon Ball and my manager, who’s still my manager till this day, he looks over and he’s like, “There’s not a camera lens that you will not love this evening. You make the most out of this opportunity tonight.” A week later, I’m back in California and I’m training for seven hours a day, but in that moment, maximize the potential.

Within that week, I took a few days off. I flew to Portland. I resigned my Nike deal. My dad told me to get in the room, and there may be things you don’t know. There are certain elements of the deal that you’re not going to be familiar with, but you know what? This is your future. This is your money and you need to be in that room. He gave me… I was a teenager. I’m 17 years old. What do I know about money? But for him to say, “Just be there, and someone in the room, the C-suite individuals that will be talking this big game, they’re going to see your face and it’s going to be a little tougher to bring the deal lower to you.”

I remember being in that room just being amazed by some of the zeros they were discussing. Right after that, I signed my first non-sport deal with Motorola. They were just coming out with the Razor phone. It wasn’t a big check, but the opportunity was big because I was going to be on billboards all over the world. My manager, he’s like, “Just wait. You take this one, people will see your face, will know your name, and that will grow into bigger things.” That was a really great lesson.

SAFIAN: It’s so interesting because you put so much time and from an early age into the tennis, into what gets you this attention. Then when the attention comes, it’s like you have to learn that business piece of it on the fly a little bit. It comes at you, but you don’t… The things that maybe from the outside look like it’s fun, like you get to be celebrating winning Wimbledon. It’s not fun. It’s just a different work.

SHARAPOVA: No. The next day, you’re focused on winning the next one, which is the US Open. There’s only a certain amount of time that you’re really allowed to think about your success, which in some ways is sad. But while you’re holding the trophy, all the other opponents are training. The world doesn’t end to watch this big moment in your life. Although you have to appreciate it and take it in, you can’t believe the hype. You have to get back on the horse and train and get better because people will now know your game and your name, and they’ll want to beat you even more.

But back to business as a young 20-year-old, you realize as a female, you’re not playing until you’re 60 or retired. You’re there until perhaps, 35 at your very best. In my early 20s, I recognize that there will be an end, and whether that’s at the end is because of an injury, whether that’s because I want to start a family, whether it’s because I lose interest, the time will come. That business frame of mind, I loved every meeting that I got to participate in. I learned through people in boardrooms. I learned from not knowing. I learned from asking questions.

Copy LinkLearning to think beyond endorsements

SAFIAN: For a lot of athletes and celebrities, their business is endorsements. That’s as far as they go. You’ve pushed farther as an investor, as an entrepreneur, and as a strategic business leader. You’re on the board of luxury fashion house, Moncler, a public company valued at more than $16 billion. Is being on a board a different pressure? How do you see your role on the board?

SHARAPOVA: Well, it’s a different type of intensity. Every meeting is like a UN meeting. They’re done in Italian because it’s an Italian public trading company. Every time you speak, there’s a similar microphone like this. You press a button, it’s your time to speak. There’s a little bit of a delay. The one thing that you really miss is the sense of a match point like in sport, where there’s this tension. You’re constantly under a little tension. When you finish something that you’ve held this tension in, there’s nothing really like it.

There’s nothing that really gets your juices flowing, and being in that boardroom was one of the first times where I was like, “Wow. I’m in unfamiliar territory. I like this feeling of having to show up and having to prove something.” Not for everyone, but for myself, I took it as an opportunity to learn. Sitting in a room with Remo Ruffini, talking about a potential succession plan, talking about the evolution of business. Moncler is a seasonal business that’s mostly focused on the winter months. How do you become a company that’s not just relevant for 70% of the time, but for 95% of the time? I learn. I love it, and I get to be in a room with smart people.

SAFIAN: You always had a reputation on the court as being a killer competitor. Are you as competitive about business in the same way?

SHARAPOVA: I don’t think I’m as aggressive. I don’t pump my fist as often, but I have a competitive nature. I love teamwork. I love the idea of having a goal and everyone having different perspectives, and aligning on a same goal. Even though I played an individual sport, team was everything to me. Getting off the court, having a crap performance and acknowledging that we just lost as a team. There are those moments that they were tough parts of my career, but I really miss them.

SAFIAN: You’ve got an investment portfolio, BetterUp, Therabody, Supergoop. You’ve also been an entrepreneur. I know you launched a premium candy brand, Sugarpova, which unfortunately, didn’t work out well and shuttered in 2021. What lessons have you learned from leading a start-up, from investing in start-ups?

SHARAPOVA: I had Sugarpova for over 10 years while I was playing and got it profitable after several years. It was an MBA on the job, ultimately. Going into it, I didn’t know what a P&L was. I didn’t know what a strategic marketing plan was. Do you sell at a savings store, or do you sell premium? Are you scaling a product that costs $5? How are you doing it but maintaining its quality? That was incredibly valuable and something that I now get to think about as I invest in companies.

Copy LinkHow early sacrifice shaped Maria Sharapova’s discipline

SAFIAN: You mentioned your son, Theo, and how young you were when you moved to the States to train. You were five, not really, not much older than he is. Your dad was with you, but your mom wasn’t able to join for two years. Do you reflect on the choices your parents made?

SHARAPOVA: Well, when you’re six years old, your parents are making choices for you. We can make that clear. But ultimately, if things don’t go well, it’s not like where you came from of what you had wasn’t good enough. It’s just you have an opportunity and a little bit of hope that maybe there is a chance to become great at something, and perhaps, that’s going to college. That’s not necessarily number one in the world. I think when we think of success, ultimately, we go to the very top. We think of, “Oh, winning a Grand Slam.” But I don’t ever remember thinking that that… I know that that existed, but I didn’t really understand the magnitude of what that victory is, or what it meant to others.

All I knew is that I loved playing the sport. I was the first one in line. Every weekend I played a different tournament in Florida. Someone I’d lose to one weekend, the next weekend, I’d play them again and beat them and like, wow. How incredible that within six days I improved. Those little things encouraged me. They kept me up at night because I wanted to be better. I think those were all the signs that both of my parents saw and said, “Wow. She loves this thing.”

SAFIAN: You were the highest paid female athlete in the world for a decade plus. In a lot of ways, you set the blueprint for athletes that followed. Much is changing right now, so fast. Social media has such a role. Women’s sports outside of tennis is getting a lot more attention. Do you look at the blueprint for female athletes differently? Is that blueprint in flux in some ways?

SHARAPOVA: Well, there’s never been a playbook. If there was, I think it’s certainly being rewritten right now for female athletes. I think there’s positives to it. There’s also negatives. I think it’s easy to get distracted in the world where there are more opportunities to make money and there are more opportunities to take advantage of a successful career, whether you are a Grand Slam champion, or whether you are a college player. I remember great financial deals that I had to say no to, because I knew that they would take up, well, one, too much of my time saying yes to incredible events that at the time as a young girl might seem really fun and interesting, but you also know that you got to be on the other side of the world competing in Asia or Europe. There are a lot of sharks out there, and you have to find the right people.

SAFIAN: Saying no to potential opportunities is an essential part of business success to focus on what matters most as a wise colleague once told me, “Bob, we can do anything. We just can’t do everything.” What are the toughest trade-offs that Maria’s struggled with, and is failure really a good learning experience? We’ll talk about that and more after the break. Stay with us.

[AD BREAK]

Before the break, tennis icon Maria Sharapova shared her in the-moment business training from Nike’s negotiating table to her now shuttered candy brand. Now, we talk about the mental side of business and sports, what’s similar, what’s different, plus what she’s learned from Actress Zoe Saldana, and whether anything in business really matches the intensity of center court. Let’s jump back in.

Copy LinkWhy style and routine can strengthen performance

We talked about Moncler. You are a sports fashion icon. What was so important to you about fashion? On the court, off the court?

SHARAPOVA: Well, fashion on the court was a huge part of an athlete’s identity. In my career over 15, 20 years, I worked with many different teams within Nike and were always striving to create unique looks, making sure that I was comfortable on court. How do you make it exciting? Wearing shorts, that was shocking for many. Having a tuxedo jacket. All those little fun bits, it’s your armor. It’s your uniform. It’s how you show up. The feeling of putting on a dress in the locker room and knowing that there are a few eyes on you. I love the element of surprise and doing something different. I love being different. I loved wearing something that others weren’t. If everyone was wearing black, I wanted to wear red. I wanted to stand out because you don’t always have to follow the pack, and you will be respected for it.

SAFIAN: That uniform, that armor it sounds like was also a support for the mental part of the game. You thought about yourself the right way when you were going into battle.

SHARAPOVA: Sport teaches you to be selfish, to take care of your body, to take care of your mind. The idea of what is a routine of starting your day with focusing on yourself, strong body, strong mind, all those things flow into life, how you handle challenges. There’s no loss that I look back on and think it didn’t teach me anything. Every loss taught me something. A lot of times, it’s when I ended up doing my best work.

SAFIAN: There are times you’ve got where you’ve got to have felt like, “I just don’t feel like doing this right now. I’m just tight. It’s not a good day for me.”

SHARAPOVA: Looking back, I remember we had an intense season where it was an Olympic year. On top of the four Grand Slams, you add the Olympics. I remember getting off the court with a silver medal and my manager at the time was saying, “Well, when do you want to fly to Montreal?” Or I think we had a tournament in Canada. I was like, “Wait, we’re not going to pull out of that? I’m playing that next week.” We had just come off of Wimbledon and then you had the Olympics, and then you’re meant to fly to Canada. It’s almost like a nonstop grind. Then you arrive in the city, and the city hasn’t had a tournament in 12 months. Everyone is all fresh and ready to see you, and you have a bunch of commitments to the tournament. Yeah.

But that comes down to the team, like managing time. When you start a season, planning that schedule is so important and being ready to pivot when you’ve had a result that’s subpar and that you thought you were going to be toward the end of the tournament, you lose first round, you have to make adjustments to your schedule and you have the right people to make them with you.

Copy LinkWhat sports disappointment teaches about business resilience

SAFIAN: Failure or disappointment sometimes is endemic. It’s endemic in business and in sport. As a tennis player, point to point, match to match. You have to get comfortable with things not going your way sometimes, and you have to be willing to take risks on the fly. Business people talk about sports as an analogy all the time. Do those experiences practically translate into business? What have you found to be similar, and what’s different?

SHARAPOVA: I think handling disappointment and the emotions with which you handle them are quite similar. In business, it’s more mental than physical, but you give so much for an outcome that wasn’t up to your standards. That’s really deflating. I feel like I have a good understanding of investing your time into something that has no guarantees of results. You can put in hours and hours, you can have all the talent, but until you get there and you do it, no one’s giving it to you.

The only time I ever felt that was last year at the Hall of Fame ceremony where my dad turned around to me and said, he’s like, “This is the first time I felt like I’m at a Grand Slam, and I know who wins.” Because every time you get to a tournament and you get to an event, you can be the number one ranked player in the world. You can be as confident all the way up here, but until you go there and until they put the net up and you play the match and you win match point, no one knows who’s going to win.

SAFIAN: Whether you win or you don’t win is in your control to a certain degree, obviously, you’re playing against somebody else, but in business sometimes, there’s so many things that aren’t in your control. I wonder whether there are business lessons that tennis didn’t prepare you for?

SHARAPOVA: The only thing in control is your serve because it’s the first shot of the point, but everything else is based on adjusting, is based on pivoting, is based on unfamiliar territory. Within seven days of a tournament, it can hail, it can be sunny. Sometimes you go on the court being prepared to play a 2-hour match, it’s 3 1/2 hours, your recovery’s very different.

The idea of change was always part of my life and my career, and always thinking about where I want to peak. I want to peak at the majors. I want to peak toward the end of the second week of the major. I don’t want to play my best tennis on a Monday of the first week, and that’s not required. I just want to be better than the person that’s in front of me. I don’t mean my best.

SAFIAN: You don’t have to be good enough to get through. You don’t have to be at your best for that match.

SHARAPOVA: You don’t have to be. That’s hard to accept because we always want the best from ourselves.

SAFIAN: In some ways you don’t want to be because you don’t want to expend resources on something that shouldn’t require those resources. You want to give enough, but not too much.

SHARAPOVA: I always strive for being deliberate about how I played and the choices that I was making on court. My coach would say just like, “Don’t be stupid. It doesn’t have to go into three sets.”

Copy LinkComposure and prioritization as competitive advantages

SAFIAN: You’re talking about, on the one hand, the mental agility in a game about once the serve starts, you have to react to what’s going around you. At the same time, this prioritizing of how much do I put into this? Those are very much big themes in business right now about both dealing with environments that are uncertain, and being ruthless about how you prioritize your resources.

SHARAPOVA: Yeah. It’s all up here in our mind of how we approach it, of the mentality that you have when things are not going well. Are you deflated? The composure that you show on a call in a meeting, the way that I think of business is composure is everything. People see how you feel, how you react, use your words wisely. No matter who you meet in life, there may be a time most likely they will come back in your life. Happens in sport all the time. It happens in business even more frequently. All those little lessons, I now get to apply.

SAFIAN: No, and others respond to you based on your composure also, both on the court and in business. You’re trying to elicit certain kinds of responses from them sometimes with your composure.

SHARAPOVA: That sounds a lot more complicated. I was like, “There’s a net and I can only take care of my side of the court.” That’s why I had a little routine in between every point. I was like, I went back. No matter if I was winning or losing, I would fiddle with my strings. It was a little practice that I had for 5, 10 seconds just to think, just to be clear, just to be composed about my next decisions.

SAFIAN: Who you’re playing against doesn’t necessarily matter? You had a legendary rivalry with Serena.

SHARAPOVA: Well, of course it matters.

SAFIAN: That made you better, you felt like it forced you to up your game.

SHARAPOVA: Of course.

SAFIAN: Yeah.

SHARAPOVA: When I was young, my father made sure that I would always play up in my age group because he didn’t think there were so many… There was as many valuable lessons when you’re beating everyone to when people are showcasing your weaknesses.

SAFIAN: Like with Serena, she’s a business person also. Do you have a rivalry with her in business like you do in tennis? I know your relationship has softened and she surprised you at the Tennis Hall of Fame induction last summer, but do you push each other on business impact too?

SHARAPOVA: No. There’s a lot of deal flow amongst us now, which is a lot of fun, because we get to see a lot of the same or similar business opportunities and we occasionally run it by one another. That’s been fun.

Copy LinkInside Maria Sharapova’s new podcast

SAFIAN: For the podcast, pretty tough. You’ve started recording some initial guests.

SHARAPOVA: Our first launch guest is Zoe Saldana, who is a friend and someone that I deeply admire. To talk through the frustrations and coming up and being a young actress and her young beginnings in Dominican Republic, and then you get to the pinnacle of winning an Oscar, and then it’s like, “Well, now what? Now, where do I go?” Having those just honest reflections of life and bravery, I love challenging the duality of you can be at the pinnacle, at your toughest self, but then you come home and there’s challenges with your kids. There’s challenges in your relationship. There’s grief, and how do you balance that? How do you not apologize for going through all of these phases in life, and being a pretty tough badass?

SAFIAN: I love the name of the show because you want to stay pretty and you want to stay tough, and then you also have to be pretty tough.

SHARAPOVA: It’s not about achieving that perfection. It’s about the journey and not having to, I guess, soften your ambition, acknowledging that that is equally as important as being soft, as being vulnerable.

SAFIAN: That joy, that exalting feeling that we see from athletes when they win a big event or a big tournament, it’s inspiring and it’s infectious and we all want that buzz and that high. Does business success ever give you that same kind of charge?

SHARAPOVA: I’d say that that match point feeling is, it’s very hard to replicate, because it’s in the moment in front of thousands of people. There’s nothing quite like it, which is the beauty of sports, of seeing the sweat and the tears, the emotions, the pressures. That’s why it’s so special. There’s nothing that could replicate it.

SAFIAN: Maria, this was so great. Thank you so much for joining.

SHARAPOVA: Thanks for the opportunity.

SAFIAN: I remember watching Maria when she first came onto the tennis scene and admiring how composed she seemed, no matter what came her way. Her focus on composure as a critical business skill is especially true when so much is moving around these days. To become unsettled and panicky doesn’t help our teams or ourselves. At the same time, I keep coming back to Maria’s observation that you can’t plan out a tennis match. That once the serve is played, you need to rely on instinct and reaction.

All the training we do, whether on the court or in our businesses, it’s about building the muscle memory to act with confidence, whatever situation is presented. That’s what enables us to stay in the game, whatever life spins our way. I’m Bob Safian. Thanks for listening.