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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 just, 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 like there, 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 and 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. I'm Bob Safian. I'm here with Maria Sharapova. Maria, great to chat with you.
Maria Sharapova
Thanks for having me on. I'm a huge fan of your work.
Bob 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?
Maria Sharapova
Oh, 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, but traveled a little bit, had a son who's three and a half now, and slowly have been working on this concept around the meaning of a pretty tough woman. You know, playing into duality of being gritty and strong and persevering, but also having a side that is soft, that is motherly and. And allowing women to be both without putting a filter on it.
Bob Safian
The. The end of the Ice Queen. I'm sure you love that label, right?
Maria Sharapova
I mean, I played into it pretty well with that fist bump.
Bob Safian
It's true. 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, like, they want to talk about their craft or their art. But it's very much a business, too. Did you, did you always get that?
Maria Sharapova
Well, sport is a business. Walking through the tunnel of, of the US Open, you know, the, the door opens and that is your platform. That's, you know, win or lose, the check gets bigger, the check gets smaller, you know, and the more you win, the more opportunities you have to say yes. And it's also, I mean, amazing lessons because the more, the more that, the more chances you get to say no, the better opportunities come about. But I don't think I realized it. I, you know, I moved to the States as a young girl. I don't think I really acknowledged what, like the full picture, the 360 approach to being an athlete. I was. So I had My head down. I mean, I had horse blinders on for a majority of my career where all that mattered is 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, now I'm supported, my family's supported, my team is supported. I can, you know, I can hire a physio now. Oh, maybe now I, I don't need that immediate check. Maybe I can actually invest in a company that perhaps, you know, three, five, ten years down the line. I'll see something, you know, in return. So the mindset shifts.
Bob Safian
You were so young when you, you know, first had success even. I mean, you won Wimbledon in 2004, first of five Grand Slams. You were 17 at that point. Do you remember how strategic you were about sort of brand alignment? Were you even making the decisions?
Maria Sharapova
I was from the first day. I mean, I remember 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 is not a camera lens that you will not love this evening. Like, you make the most out of this opportunity tonight, right? A week later, I'm back in California and I'm training for six, seven hours a day. But in that moment, maximize the potential within that week. You know, I took a few days off. I, 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, you know, 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. So he gave me, you know, I was, I was a teenager. I'm 17 years old. What do I know about money? But for him to say, just be there, you know, and someone in the room, the C suite, individuals that will be, you know, talking this big game, they're going to see your face and it's going to be a little tougher, you know, to bring the deal lower to you. So I remember being in that room, just being like amazed by some of the zeros they were discussing. Right after that, I signed my first, like, non sport deal with Motorola. They were just coming out with the Razer 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, just wait. You take this one, people Will see your face, will know your name, and that will grow into bigger things. So that was a really great lesson.
Bob Safian
I mean, it's, it's so interesting because you, you put so much time and from an early age sort of into the tennis, into, you know, what gets you this attention. And then when the attention comes, it's like you have to learn that business piece of it on the fly a little bit, right? Like it comes at you, but you don't, you know, and, and 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 kind of work.
Maria Sharapova
No, the next day, I mean, 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, are training. You know, the world is an end to watch this, this big moment in your life. And although you have to appreciate it and take it in, you can't believe the h. You have to get back on the horse and train and get better because they're, you know, people will now know your game and your name and they'll want to beat you even, even more. But back to business as, As a young 20 year old, I mean, you realize as a female, you're not playing till, until you're 60, right? Or retirement. You're, you're there until perhaps, I mean, 35, at your very best. And so 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 start a family, whether it's because I lose interest, the time will come. And so that business frame of mind, I loved every meeting that I got to participate in. And so I learned through people in boardrooms, I learned from not knowing, I learned from asking questions.
Bob Safian
For a lot of athletes and celebrities, their business is endorsements. I mean, that's sort of as far as they go. You've pushed farther as an investor, as an entrepreneur, and as a strategic business leader. I mean, 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 kind of pressure? Like how, how do you see your role on the board?
Maria Sharapova
It's a different type of intensity. I mean, every meeting is like a UN meeting. They're done in Italian because it's an Italian public trading company. So every time you speak, I mean, 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. And the one thing I, I really like that you really miss is the sense of, like a match point. Like in sport, you. 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 like, 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. I mean, you know, sitting in a room with Rama Ruffini talking about, you know, a potential succession plan, talking about the evolution of business. You know, Montclair is a seasonal business that's mostly focused on the winter months. Right. How do you become a company that's not just relevant for 70% of the time, but for like 95% of the time? So it's. I learn, I love it, and I get to be in a room with smart people.
Bob Safian
You always had a reputation on the court as being a kind of a killer competitor. Are you as competitive about business in the same way?
Maria Sharapova
I. I don't think I'm as aggressive. I'm. I don't pump my fist as often, but I have a competitive nature. I love, I love teamwork. I love the idea of. Of having a goal and, and everyone having different perspectives and aligning on the same goal. Even though I played an individual sport, team was. Was everything to me. Right. Getting off the court, having a crap performance and like, acknowledging as a team, like, there are those moments that they were tough parts of my career, but I. I really miss them.
Bob Safian
You've got an investment portfolio better up therabody Supergoop. You've also been an entrepreneur. I know you launched a premium candy brand, Sugar Pova, which unfortunately didn't work out well and shuttered in 2021. What lessons have you learned from. From leading a startup? From investing in startups.
Maria Sharapova
I had Sugar Pova for over 10 years while I was playing and got it profitable after several years. It was an MBA on the job ultimately. I mean, I. Going into it, I didn't know what a P L was. I didn't know, you 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, as I invest in companies.
Bob Safian
Mentioned your son, Theo, and, and you know how young you were when you, when you moved to the States to, to train. You were, you were five. Not really, not, not much older than he is. Your dad was with you, but your mom wasn't able to join for like two years. Do you reflect on the choices your parents made?
Maria Sharapova
Well, when you're six years old, your parents are making choices for you. Let's 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. You know, that's not necessarily number one in the world. So kind of, I think when we think of success, we ultimately, we go to the very top, right? We think of, oh, you know, winning a Grand Slam. But I, I don't ever remember, like, 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, like, I want. Every weekend I played a different tournament in Florida, you know, someone I'd lose to one weekend, the next weekend I'd play them again and beat them. And like, wow, I mean, how incredible that within six days I improved. So those little things, like, encouraged me. They kept me, you know, they kept me up at night because I wanted to be better. And I think those are all, those were all the signs that, you know, both of my parents saw and said, wow, you know, she, like, loves this thing.
Bob Safian
You were the highest paid female athlete in the world for like a decade plus. And in a lot of ways, you sort of set the blueprint for athletes that followed. So 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? Like, is that blueprint in flux in some ways?
Maria Sharapova
Well, there's never been a playbook, and 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, you know, great financial deals that I had to say no to, you know, 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 know, 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.
Bob 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. So 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.
Jeff Berman
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Jeff Berman
If you're a regular here, you already know that the best business lessons aren't hypothetical, they are proven. That's why I love the Business History podcast. The show unpacks the real decisions and turning points that have shaped iconic companies, from the long history of humans trying to cheat death and sell the solution to the surprising origins of prediction markets. Hosts Jacob Goldstein and Robert Smith dig beneath the surface of how business really works and how much further back it goes than you might expect. Find business History wherever you get your podcasts or watch it on YouTube.
Bob Safian
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. We talked about Moncler. You are a sports fashion icon. What was so important to you about fashion on the court, off the court?
Maria Sharapova
Well, fashion on the court was a huge part of an athlete's identity. In my career over 15, you know, 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? How do you, you know, wearing shorts like that was shocking for many. You know, having a tuxedo jacket. So all those little fun bits, I mean, it's your armor, it's your uniform. It's how you showing up. You know, 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 right. 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.
Bob Safian
And that, that uniform, that armor, it sounds like, was also a support for the, the mental part of the game. So you thought about yourself the right way when you were, when you were going into battle.
Maria 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, you know, of starting your day with focusing on yourself, strong body, strong mind, all those things flow into life. You know, 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. And a lot of times it's when I ended up doing my best work.
Bob 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. Like, I'm just tired. It's not a good day for me.
Maria Sharapova
Looking back, I remember we had like an intense season where it was an Olympic year. So on top of the four Grand Slams, you add the Olympics. And I remember, you know, getting off the court with a silver medal and, and my, my manager at the time was saying, well, what, when do you want to fly to Montreal? Or we had a tournament in Canada. And I was like, wait, we're not going to pull out of that. We're, I'm playing that like next week. We had just come off of Wimbledon and then you had the Olympics and then you're meant to fly to Canada. And so this just, it's, it's almost like a non stop grind. And then you arrive in the city, right? And the city, city hasn't had a tournament in 12 months. So everyone is, you know, all fresh and ready to see you. And you know, you've had, you have a bunch of commitments to the tournament. So yeah, I mean you, but that, that comes down to the team, like managing time when you start a season. I mean, planning that schedule is so important and being ready to pivot when you've had a result that's subpar and that, you know, 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, and you have to write, have the right people to make them with you.
Bob Safian
Failure or disappointment sometimes is endemic. It's endemic in business and in sport, right? As a tennis player, point to point, match to match, you sort of 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? Like, what have you found to be similar and what's different?
Maria Sharapova
I think handling disappointment and the emotions and with which you handle them are quite similar. Right. In business it's more mental than physical, but you give so much for an outcome that that wasn't up to your standards. And so that's just, 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 like there, no one's giving it to you. You know, 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, like 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.
Bob 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. Control and, and I wonder whether there are business lessons that tennis didn't prepare you for.
Maria Sharapova
The only thing in control is your serve because it's the first shot of the point. But everything else is, is, is based on adjusting, is based on pivoting, is based on unfamiliar territory. I mean, and within seven days of a tournament, you can have, it can hail there, it can be sunny. Sometimes you go on the court being prepared to play a two hour match, it's three and a half hours. Your recovery is very different. So the idea of change was always part of my life and my career and always thinking about where I want to peak. Like 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.
Bob Safian
Right.
Maria Sharapova
I don't need to.
Bob Safian
You have to be good enough to get through. You don't have to be at your best.
Maria Sharapova
For that matter, you don't have to be. And that's hard to accept, you know, because we always want the best from us.
Bob Safian
And in some ways you don't want to be because you don't want to expend resources on something that doesn't, shouldn't require those resources. Right. You want to give enough, but not too much.
Maria Sharapova
I always strive for being, you know, 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.
Bob Safian
Since you're talking about on the one hand, sort of the, the mental agility in a game about once the serve starts, like you have to react to what's going around you and, and at the Same time, this sort of prioritizing of, you know, how much do I put into this? Those are very much, you know, big themes in business right now about both dealing with environments that are uncertain and being ruthless about how you. How you, you know, prioritize your resources.
Maria Sharapova
It's all up here, right in our mind of how. Of how we approach it, of how, you know, the mentality that you have when things are not going well. Are you deflated? Are you. You know, like that? The composure that you show on a call, in a meeting, the way that I think of business is like, composure is everything. People see how you feel, how you. You know, how you react. Use your words wisely. You know, no matter who you meet in life, there. 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. So all those little lessons I now
Bob Safian
get to apply and others respond to you based on your composure also, right. Both on the court and in business. And so you're trying to elicit certain kinds of responses from them. Sometimes with your composure, that sounds a lot more complicated.
Maria Sharapova
I was like, there's a net, and I can only take care of, you know, my side of the court. You know, 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. Just practice that I had for 5, 10 seconds just to think, just to be clear, just to kind of be composed about my next decisions.
Bob Safian
And who you're playing against doesn't necessarily matter. I mean, you kind of had a legendary rivalry with Serena. Well, of course, you said, you know, that. That made. That made you better. You felt like it forced to up your game, right?
Maria Sharapova
Of course.
Bob Safian
Yeah.
Maria Sharapova
When I was young, I. 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, you know, people are showcasing your weaknesses. Right.
Bob Safian
And like with Serena, she's a. She's a business person also. Do you. Do you have a rivalry with her in business like you do in tennis? I mean, I know you know, your relationship is softened, and she surprised you at the tennis hall of Fame induction last summer. But, like, do you push each other on business impact, too?
Maria Sharapova
No, we actually, there's. There's a lot of deal flow amongst us now, which is a lot of fun because we get to see. We get to See a lot of the same or similar business opportunities, and we occasionally run it by one another, so that's been fun.
Bob Safian
For the podcast. Pretty tough. You've started recording some initial guests.
Maria Sharapova
Our first launch guest is Zoe Saldana, who is a friend and someone that I deeply admire. And 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? You know, and having, like, those just honest reflections of life and bravery. I love challenging, like the duality of, you know, you can be at the pinnacle, at your toughest self, but then you come home and, you know, you may have. There's challenges with your kids. You know, there's challenges in your relationship. There's grief, there's. And how do you balance that, right? How do you not apologizing from going through all of these phases in life and being a pretty tough badass?
Bob 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.
Maria 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.
Bob Safian
And 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?
Maria Sharapova
I'd say that that match point feeling is. It's hard to replicate, very hard to replicate, because it's. In the moment, in front of thousands of people. There's just. There's nothing quite like it. Which is the beauty of sports, right? Of seeing. Seeing the sweat and the tears, the emotions, the. The. The pressures. That's why it's so special. There's nothing that could replicate it.
Bob Safian
Maria, this was so great. Thank you so much for joining.
Maria Sharapova
Thanks for the opportunity.
Bob 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. 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.
Maria Sharapova
Humans will never be more intelligent than AI.
Jeff Berman
There's going to be two types of companies.
Bob Safian
Those are great at AI and those
Jeff Berman
that went out of business because they weren't.
Bilt Membership Host
How do we build a future that is human centered?
Rana El Kaliouby
I'm Rana El Kalyubi and on my podcast Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur and investor, I know what it takes to build AI that works for everyone. Every week I sit down with the pioneers shaping our future and we take you behind the scenes of the AI that's transforming our lives. Find Pioneers of AI wherever you tune in.
Bob Safian
Rapid Response is a wait. What? Original. I'm Bob Safian. Our executive producer is Eve Trow. Our producer is Alex Morris. Associate producer is Mashumaku Tonina. Mixing and mastering by Aaron Bastinelli. Our theme music is by Ryan Holiday. Our head of podcasts is Lital Milad. For more, visit rapidresponseshow.com.
Podcast: Masters of Scale
Host: Bob Safian
Guest: Maria Sharapova (Tennis Champion, Investor, Entrepreneur)
Air Date: April 28, 2026
This episode features Maria Sharapova, renowned tennis champion and now a business leader and investor, as she shares how her experiences on the tennis court have shaped her approach to entrepreneurship, boardroom strategy, and leadership. Sharapova draws candid parallels between the “match point” mentalities in sports and business, revealing how resilience, adaptability, and composure transfer from the court to the boardroom. The episode dives deep into her transition from celebrated athlete to investor and entrepreneur, her thoughts on personal branding, handling failure, and the balance between toughness and vulnerability.
On Composure as a Business Skill:
“Composure is everything. People see how you feel, how you react. Use your words wisely.” (26:28)
On Fashion & Brand:
“I loved being different… you’ll be respected for it.” (19:47)
On Handling Failure:
“There’s no loss that I look back on and think it didn’t teach me anything. Every loss taught me something.” (20:56)
On Business Pressures vs. Sports:
“The one thing I… really miss is the sense of like a match point… There’s nothing that really gets your juices flowing [like that].” (10:28)
Maria Sharapova’s transition from champion athlete to entrepreneur and investor is a masterclass in adaptable leadership. Her candid reflections throughout the episode are grounded, generous, and practical for any listener navigating high-performance environments—athletic, business, or otherwise. Sharapova champions the duality of resilience and vulnerability, and her stories on negotiation, failure, and learning by doing bring relatable dimension to the mythology of elite sports and business.
“It’s not about achieving that perfection. It’s about the journey and not having to soften your ambition.” (30:18)