Wow. I mean, if you read what she's written, if you see interviews with her,
like '04 is when it all just takes off for her. 17 years Old. But here she is at 17
wins her first Wimbledon, the competition with another icon. Yeah.
in, in Williams. The fathers coming together. I know. And my favorite part is,
I mean, it's like a movie. Her kind of going up the steps.
I know. Trying to find her father
father's trying to find her. Yeah. And you're a father. I
mean, it is just that to me is just awesome. And so from a business perspective, that changes everything too, because she gets the Motorola
deal all of a sudden. She's one of the most famous
athletes in the planet. I, I have to say, I'm
really excited for you guys to compare notes because this
timing, 2004 stuff going on with you at that Moment too. It did. Which, we'll talk
about it with her a little bit. I've been involved in a few business calls with her in meetings. But she has like the perfect brand. I mean, this is before social media. I, I'm really wanting to dig
into her business ventures because I know she's
going about it the same way. Exactly. And this is, it's
sort of a cornerstone of, I feel like all of our
conversations is, so this happens. How do you actually translate
that to business success, which she's done, but not everybody does. No. And she's making it look easy. I mean, she's hit bullseye in
more ways in one. Absolutely. This is very fancy for a podcast. Alright, so officially
like introduce yourself. Wow.
Yeah. I'm Maria Sharapova. I am a five time grand slam champion and I'm now a mother and entrepreneur and just a curious human being. Yeah. So we have so
many things that we want to talk to you about. And I read your book and I, I have to say like, it
really is like lodged in me. Like sort of your, That's a big compliment. Well, I mean, it, I think
it's your willingness to kind of go there, you know? And I think the, the sort of rawness and the vulnerability you, you show in, in telling that story. I mean, I do wonder like
going all the way back, like, when did you know, and
you've written about this? Like when did you know that
you had something special? I don't think I ever
allowed myself to accept or to realize that I,
I had something special because the, the moment that
you think you have it down or you know too much,
or you know everything and you consider yourself the
best internally, maybe the outside world can, but internally is, in my
opinion, is a time that you have to be very careful about because you start believing in the hype and you start hyping your own self up. And then you're living
up to these unprecedented expectations. And I don't know if they're
ever going to be met. You know, Maria, I'm such a big fan of everything you've done off the court. Obviously the five grand slams
and what you're doing now. It takes so much courage to do that. But going back to the early days building what Jason just asked, you
know, I come from two parents that are immigrants
from Dominican Republic, very modest beginnings. And there was always a
sense of imposter syndrome. And I think that was my gift
and my curse. Right? It led me to a great career, but it also led me to
a one year suspension that was very hard on me. Did you ever feel coming up a little bit of an imposter syndrome? Or did you feel like you
belonged from day one? I knew that what I
was doing was different to other families, to other children. I knew that I had a different path and I, and I was living almost, I
mean, it was a dream and, but I had a very clear vision. And so did my mother and my
father, my father particularly. 'cause he was my coach for many years. And it was, you know, his big goal. I was too young to really
have those big goals. But as I followed the, this
road that he, you know, paved for me, I realized very much that this dream was becoming a reality. That, you know, you had a choice to make every single day when
you wake up to be the best. And I was given an, an
incredible gift of, you know, having a strong mind of
persistence of focus. And I was talented, but I wasn't like as physically
strong as other children. And I love this idea of being different. And I accepted that I didn't
have a typical upbringing, that I was an immigrant, that
I came to the United States as a young girl and I didn't
feel like I always belonged. But I found that as a gift. I didn't find that as a disadvantage. But just following up on
that, I remember the first time that I traveled to Texas
and I was 15 years old and I wore the US uniform
representing the US and the US Olympic teams. And I looked around the room
and I was a rising junior. Everyone was a rising
senior in the summertime. And I said, wait a minute. I'm, I'm as good as everybody here. And I'm a year younger. I
was the only underclassmen. That was the first time that I go, I can go big if I really focus. What was that moment
for you that you said, I can be something special? So You see, it's funny
because you, you, you give me that example in that story. And I, there's not one that
I particularly look back to because after a victory or after beating someone
that was older than I was, or a boy that, you know, was stronger and, and you know, perhaps
had a, a better talent or was just physically better
at the sport, I still knew that I had to wake up and
keep doing it tomorrow and prove myself again and go to another tournament
over the weekend in the middle of nowhere in the, you
know, dumps of Florida and figure out a way to win. And so I, I think it was
just this reality element that kept coming back to me. Like I came from, you know, as you have from very humble beginnings. And I was never afraid to go back, but I dreamed of the best I dreamed of holding the biggest trophy. But I also, in, in this other
context, I, if I went back to what I had before, I didn't,
I didn't think badly of it. Like the, the foundation that my parents had built
back home in Russia. They were both, you
know, my mother was very young, she was still in university. But my, my dad had a decent job. He wasn't making a lot of money. And the, and the United
States considered no money. But overall, like I had
a great environment, I had a healthy environment,
I had food on the table, I had great loving parents. And so if those were the
conditions that I had to go back to, I was okay with. And, and perhaps that is
what gave me the confidence to just keep going. Yeah. And just keep striving
for better and better. And hey, if the top didn't
happen to what I envisioned, then it was okay to go back
to those humble beginnings. So you've mentioned your
parents a couple times and you know, when we think
about the, the concept of The Deal, the sort of
unifying principle of all that, your earliest partnership is your dad. Yeah In terms of like you unwitting, But it wasn't a choice. It wasn't a choice. Right, exactly. And I'm Okay with it.
And you're okay with that I was lucky.
And so as, as you come of age, I mean, even as you get to be, you know,
even 10, 11 years old, 11 years old, you know, you
signed with Nike, I believe you are at a very young age in
a business partnership Yeah
With, with your dad. How did that feel and what were sort of the
undercurrents of that? Yeah. Well, I'm an only
child and was, and still am. And so I built this very
strong bond with my parents. They were both very young. My father, you know, enjoyed sport. He loved sport, he played hockey. That was a big sport in Russia. He thought he was some tremendous athlete. I kept telling him he wasn't that good. And I still do till this day,
my mother, she would take me to the ballet no matter what city I was in and just helped me grow beside
everything else but sport. And so they had these very
different gifts that they, that they helped, you
know, instill in me and, and shaped me in many ways. And I think that grounding
element of those partnerships, like I would go to the tennis court and I would be around my dad and, and of course I negotiate
with him whether I was there, you know, I'd start my
practice with serving for 45 minutes or I'd end it. Like I had a preference
and he had his preference. And you know, it'd be a little bit of a negotiation no
matter how young I was. Right.
Like I'd find my way to, you know, give an opinion and then I'd come home and, you know, my mom had my schoolwork in front of me and she made sure that
I ate the right things and that I stretched, you
know, before I went to sleep. 'cause she thought that would
help me grow. She was right. Because I'm much taller than my parents. Right, exactly. You were hanging from a bar though at some point. I was hanging from a bar. Yeah.
And then I had to stretch right before going to sleep. 'cause she said when you go to sleep, that's when you elongate, that's when your body recovers. And it needs to be nice
and loose. So here we are. And the biggest business
decision your parents make is for you and your dad to
come to the United States. I mean, we talk a lot about risk when it comes to business. That's a huge bet.
Huge risk on you at age five. You know, you get a little bit of encouragement from
Martina Navratilova. You and you've talked about how, you know, there are these key moments
that you look back on that are clearly catalytic in
your, in your progression and, and in your success. Yeah.
But that is a massive risk that you must look back on and think, "Wow." Yeah. My father and I were
breaking rules in the public tennis courts from the first
day we arrived in Miami. And I remember we arrived, someone was supposed to meet us, they didn't, we happened
to, to stay with a family, sharing a hotel room. And the next morning my
dad said, let's wake up. We gotta go find a
court, a tennis court. And we just happened to
go around Collins Avenue and then found some private court that he jumped the fence on. And here we were, open the
gate from the back practicing. So those are like the
recollections of arriving to the United States of America. Finding your way, finding your path. And there are many times where
it could have gone wrong, but your, your determination
and you know, outside voices and there are many people
along those paths that, that help shape you
know, your, your future. So Maria, when I hear you
talk about your father, I, I can't help to think about, you know, my dad leaving my family, my mother, my brother, my sister, and kind of left the four of us behind. And my mother went on to take two jobs. And I always thought, I think
about the gift of your father and the curse of my father
leaving us, there's both sides. Right. Part of him leaving was I had nobody to kick me in the butt. I had to do it myself. And
I knew early on that I had to be the provider for my family. Probably when I was around 11 or 12. I hear all the good,
any challenges of having that first partnership
be with your father? You can't just fire your
father. He can't fire you. I mean, it's blood. Yeah.
Any challenges along the way? Yeah. As a, as a young girl,
I mean, he, he would cut my, you know, my hair and,
and it would be wonky and I would not appreciate it. And neither did my mom.
'cause she was away for the first two years.
Tennis-wise, I have to give him so much credit. I mean, he was in his early
thirties with $700 in, in his back pocket of his Levi's. He was trying to find any kind of job that would help support, you know, string my next racket
for my next tournament. So I don't, you know, the greatest gift that he gave me was acknowledging that at some point he
will have to step back. And for a father in sport,
particularly in tennis, as a father of a, of a girl that's won grand slams with him, is a very tough acceptance to have. We had, I, I did that after my third grand slam
at the Australian Open. I wanted to have that independency and, and it was more for me than anything else. It was not about money, it
was not about victories. It was just this little, little bird, this little instinct of mine that said, you
know what, this is time. I won my third grand slam
at the Australian Open. And I, I drafted a Now, now I'm scared for you, Maria. Is is that conversation happened on text, on phone in person? Oh that's where I was getting to. Okay, good. Now I'm excited
to hear this. This is nervous. I drafted a really
good email. Oh, okay, okay, okay. I just thought I was gonna
do this much better on email and
craft my thoughts better. And, and I did. And I, I don't, I couldn't look at him in
the face while saying that, but I also knew that
he knew it was coming. He just didn't think it was gonna happen after I just won my third grand slam. Yeah. Yeah. It's a, it's a tough one. But, but you have to like rip
that bandaid, you know, as, as someone that was in
my twenties, I was ready. It had been a partnership
for, you know, over 20 years and it was time to do it on my own And to do it after a third grand slam. Yeah. So much better than
after a terrible defeat. Right? Yeah. Which is what happens most of the time. Right, exactly. Yeah. Well, and and it was interesting too because you, you essentially kind of turned his own logic on him right? Because he had been
pretty robust in, in terms of like turning over your
team pretty consistently. Yeah. You know, firing
coaches along the way just to make sure you kept
it fresh. Is that fair? Yeah. I mean, I I
never really fired him. He was still very much
involved. Yeah. Right. I guess the only thing that, and and when you say fire,
like you evolve, right? And, and that's
one of the, the hardest, the challenges that I find now
is like, what you needed two, three years ago perhaps is not
what you need for the future. And like, how
do you make that change and acknowledge that this person was right for you at this time, but is
no longer right for you and, and for your own future
and perhaps not for theirs. And that conversation is one
of the most difficult ones that you have in business. 'cause team is everything. And if you don't see and feel that your team
is moving with you toward that one direction and, and the fact that he just
was able to step back and say, "Hey, you do this." I mean, he was still very much involved. He'd call all the coaches and
speak to them after matches. He's always the first person I call as, it wasn't like I went to
my coach, I call my dad. Yeah, right. You know,
Like, you have that, you have that partnership and relationship. He knows you better than anyone. And I, and I respected that and I always respected his opinion. So speaking of building
your team, I mean, one of the catalytic moments clearly too is IMG because that sets you, it feels like on a
completely new path or it sort of helps set the direction. Yeah. My father and I arrived to the IMG Academy on a Greyhound bus in the middle of the night. We didn't know if it was open or not, but it was the only time that the bus came to Bradenton, Florida. And we knocked on the door, the receptionist said, "You're crazy. Come back at 6:00 AM when
our front office opens." So we went to a motel,
came back in the morning and they put me in my, my
father said, we don't have a, I just brought my, my daughter from Russia and she's talented and I'd like, I'd like
for her to practice here. And I'm sure they looked
at him with eyes wide open and said, "This guy's nuts." And so let's, let's
bring them in for the day and then try to get rid of them later. They put me in a group and the coach that was
running the group said, Hey, called Nick Bollettieri right away I went to see Nick within hours. And Nick called IMG and
that's how it spiraled. Wow.
Within 24 hours. And how old were you then?
I was seven, six and a half. And then it, I mean, it takes a couple twists and turns though. Oh, many You end up at a different Yeah. Academy because Bollettieri is like, this isn't working after, Oh, Bollettieri was a, it
was a sports factory, right? Like if you want individual
training where you come in and there's one person looking after you for six hours a day, that's most likely not gonna happen. But it was also a time where
we needed an investment. We needed money in order
to go and, and train. I mean, you know, it, this tennis is a very expensive sport. You need to invest so much capital and with absolutely no guarantees. And so IMG put the first check in and I think that was the
last time that I like, felt really awful about
owing money to someone. Mm. Like I've never, So how does that work
IMG, invest in you? How do they get their
return on their capital? So once you make a little
bit of cash, then you return with a certain interest. And I hated that feeling. I
mean, the feeling, feeling of Really?
Oh, Yes. Why, why do you think that is? I just, even now, like
anytime I'm in business and, and I do deals or even buying a house, like the idea of borrowing someone's money and then owing it to them is
like, I don't know if it's because of the past and that
I needed that money in order to survive in, in, in the sport. It like left a really, like,
I don't know, this feeling of I never wanna be in that position. Oh, wow.
Yeah. And so I, I can't get too
far along I, I want to get to sort of your success on,
on the court in a second, but from a business perspective, you know, every athlete's dream or many athletes' dream
is to sign with Nike. You do that at 11.? Are you conscious at that point I don't really it wasn't
like a big deal to me because I didn't recognize
what that even means. To me, that meant that I
could have free tennis skirts. Right.
And that was fantastic. During the time I won Wimbledon, I was on a very small mediocre
Nike contract as a teenager. And after I won, they very
sweetly flew us up to Portland and gave us the whole, you
know, shebang experience. And that to me was like, That was the moment, That was the moment, yeah. Where I realized that, okay,
I had done something special. Well, let's talk about that
because Wimbledon... winning Wimbledon the first time,
I think it's safe to say literally changes everything. I mean, it changes your Nike deal. It also brings Motorola
in. Tell us about that. The business of Maria
Sharapova totally changes When you, when you frame it
that way, I'm like thinking, wow, that is so big. But like, when you're a 17-year-old girl, you don't look at it that way. Because if you think that wow,
everything now has changed. How do you go, how do you
wake up at 6:00 AM put on your training gear when it's
like freezing outside and go and hit a hundred serves
and with a cold shoulder. Like where's the
motivation gonna come from? So if I can be honest, I never
allowed myself to feel that that change or that shift has happened because you constantly
have to find those moments of inspiration to keep going. And they're not...
And inspiration to me was not by, you know, signing a contract with Motorola or getting the new
razor phone, even though that was an incredible brand. It was the fact that,
like, now when I went to train in Los Angeles, I stayed in a, in this hotel room in Hermosa
Beach, and I got an upgrade. I had a better room.
And that was exciting. I'm here like freaked out because it is resonating so much. At 17, I was drafted from
Miami to the Seattle Mariners, like all the way across the country. I had to kind of bring out the map and go, where, where exactly is Seattle? Where are you going? Right.
But there's a moment when I signed my contract where
I saw my mom work so hard that I made a promise that
I will buy her a house. I got her a used Mercedes-Benz. I remember one 90 and I promised her
she'll never work again. And she's 87 to this day and she's never worked a day in her life. After my contract. When I
bought my black Cherokee, I gotta tell you, Jeep Cherokee, it was black with a little gold. That was my flex. And I was 17 and I just felt like
the king of the world. Was there ever a little moment where you either got a big check that for a minute you said, okay, I'm gonna enjoy this quietly and then I'm gonna go back to my serves? Yeah, I, I took my mom and two girlfriends to the Caribbean on my first ever vacation Where? I'd never seen, we went to Nevis and it was the closest like
resort, decent resort to, to Sarasota where I was training. And we took five days off and I'd never been on
a vacation in my life. And I left there and I thought, wow, the fact that I could fly my mom,
two of my girlfriends on a private jet to this
place with blue water and Boogie board all day long. Like that was our thing. Yeah. And come home and train the
next day is the greatest, most amazing gift until this day. Like I, that feeling of going away, of disconnecting from the
world of being with my friends and my family and treating to them to this amazing experience
that incorporates travel and wellness. And So this is just post Wimbledon? Yeah.
After that season I was not taking vacations
before that. Right.
Yeah. And and you didn't think you, why weren't you? You just couldn't, I didn't know what that meant. I don't think I ever took
more than a day or two off. But the, the grind of the year, the schedule of playing 17 to 20 tournaments a year, the travel, the media responsibilities,
the brand responsibilities, you need to disconnect from that. So I'm gonna bring you
back to when you were 17, call it a month before you
win your first Wimbledon. What is a day like for
Maria to give us a taste of your work ethic and your schedule? Yeah, so a month before that, Wimbledon was the French Open and we, it was actually
the first grand slam quarter final that I'd been in. So it was a big, it
was a big event for me. It was a big result for me. People expected good things for me. Perhaps not on the clay courts, but it was where I made my mark, where I felt like, wow, okay. I got to the quarter final baby steps and moving in the right direction. And the following week was the, the first warmup tournament
in Birmingham in, in England. And they were showing the
final of the French Open. And I, at the time, I was
sitting in a hotel room with, with a Russian colleague that was also playing the same tournament. And there were two Russians
playing that final at in Paris. And I just watching the TV and knowing that there was
gonna be a Russian woman, like holding that trophy, I,
I wanted, honestly, I just, I wanted it to be me. And I was so upset that it was
happening to somebody else. And, and I remember speaking,
you know, about it with her. It was a colleague named Maria as well. And just telling her
how this should be us. Like we should be in the
final, why are the other, these two girls are in the final. So I already had that
competitive spirit in me and I was training for, for that Wimbledon victory
without even knowing it. Because one of the things that comes through very clearly in, in
sort of learning about you is you are a ferocious competitor. I mean, really, I mean, you would set your sights on somebody. I mean, Serena is obviously sort of like the alpha example of this. Do you still have that feeling
in, in your mind of being so intent on winning? Yeah, if I competed
in the same tournament, no matter if it was a woman or
a man winning that tournament and it wasn't me, like I would
inside, I would feel upset that it wasn't me on the stage. Like I would envision myself being there. And if it didn't happen
to be that tournament, like I would genuinely be upset and eager to get out
on the practice court, whether it was an hour
later or the next morning or like it, it fueled me. Absolutely. So I wanna take you
back just for a second. 'cause you, you mentioned Motorola or you mentioned sort of that
moment of, of winning and, and that it, it didn't resonate with you as much as a competitor. And yet I have to think
you look back on that as a business person
Yeah. and realize that was a massive
moment, Massive
In terms of validating you as a brand. It it, you know, tell us about that. Yeah, I was on, I was on center court after that that win tried to call my mom, she was on a JetBlue flight on her way to New York to actually meet me. 'cause I had some, some things
to do over that weekend. I was late because I
happened to be in the final, she watched me win on the
television mid-flight. I tried to call her. So from center court using it was one of those crap phones. Can't reach her. And then I realized she was on the flight. And then next thing you
know, a week later I have a, a global deal with, with Motorola. And the deal itself
wasn't financially heavy. It was actually, it was, I think it was a few hundred grand a year, perhaps more. But it was such a great brand alignment at the time. They were coming out with their razor phone. Right.
I was one of the first few people that ever seen it. I was in all the campaigns with it. And it, it was a smart
move by, by my team and I, because it was taking, you know, it was, it was taking a company that
was about to, to do a lot of many campaigns around a product that I was involved with. And it got me on billboards in
from Tokyo to Seoul to Paris. And it opened up so many more
doors than perhaps a deal that was worth a few million a year. And were you and your team
conscious of that at the time? Absolutely.
Okay. So that, that this had sort of a, and and this is something we've talked about before, you know, sort of this
cultural relevance, right? I mean
Absolutely. It was just like a zeitgeist type of deal. I don't think, well, I mean, you know better than than anyone. You don't take deals just for the money. There's, you have to think of the right positioning in your career. Is it the, is it about the
team? Is it about the founder? Is it about the product? Is it, how are they helping you know, your name and your image? Where are they focused on? Is there a market that you're
particularly interested in? Like, I loved going to, to
Asia and Japan and China. I loved playing there.
I loved my fans there. I had a huge fan base. So, you know, if there was a company that was focused on a particular campaign in that area, then you know, that that
would be something that I'd, I'd be curious about. You know, some are just
like, you see it, you hear it, you smell it, you know, it's a no brainer. And sometimes, you know, Warren
Buffet talks about he knows if he is gonna invest in a founder or CEO in the first five minutes. So Motorola is a no brainer.
Do you do that too? Well, I was gonna tell you about this one. 'cause this Guy Oseary
our mutual friend. You know, one of my biggest
misses of all time was Uber. And I remember I was
living in the West Village and we had just finished
playing the Red Sox and we were having dinner at the Waverly. Now it's past midnight and we're having a couple cocktails and he goes, I have
this investment for you. I want you to look at and I only have $250K for you to invest in. I said, great, great. So
we walk down the street and he presses a button and he sees the car and the car's coming. And I'm like, okay, that's
a great, you're a mentalist. Do do it again. He goes,
okay, I'll erase it. And he does it again. Two minutes a car pulls up, I goes, okay, now I want this investment. And my $250K, I needed to
wire before noon the next day. My business manager was out
on the west coast out in LA. So timing, I missed it. Is he fired? No, he's still with me. Oh ****!
But that $250K, You're loyal. The $250K Maria would've been close to 50 million bucks today. Oh my. But do you think of that,
like, do you think that that was a missed opportunity? Like do you look back and think that's a regret?
Yeah, I do. But my point is, and
this is my question, sometimes the team, the
business manager, the lawyers, there's a lot of handlers that
we have sometimes around us. And I feel like paralysis by analysis, there's sometimes you just
gotta say, kind of screw it. A, have you had misses? And
two, do you sometimes say, you know what guys, team, I appreciate it. There's a Maria's call,
I'm gonna go for it. I see a lot of deal flow and I see many things that could work well and many things that are
not necessarily go well. And sometimes you take chances
and, and you bet on it. But there was one deal actually, Andy Roddick called me up,
not that I wanna blame Andy, but he did call me up. He says there is a, it was
an app, failed app right now at the time it was very similar to what Cameo ended up doing very well. And it, the, the user face
had two different apps. So one for the user and one for for the hotels that was offering these services. And I said to the founder, I said, why can't this just be one
app for the, the people that are providing the
service and for the user? And he said, we just can't do that. And I said, well, okay,
I still believe in you, but I never, I just, I, I thought that was gonna be challenging. And, and I actually
invested quite a bit into it and it, it, it never took off. And that was my first
bit of of technology. And this must have been over 10 years ago. Yeah, there are many of them. But, but you can say
that about so many deals. Like you, you think so
many of them will work and they're so passionate
founders, great backgrounds, you know, they know what they're doing. Here's my money. We have
so many people around us that help guide us and help us. And whether it's assistants or managers, whether
it's a business manager or you know, in in WME or someone else. But at the end of the day,
you control everything. And that's a big lesson
that I've learned is like, if you're passionate about something, if you wanna get
something done, you do it. Don't rely on others. If you need to wire 250 grand
somewhere, you call your bank. Like, and make sure you
have your details. That's right, that's right. But you have to, and and that's, that's a very important lesson because there are so many
middle men in the system and things get lost. I agree. That was a great lesson. Yeah. And I mean, you have been pretty expressive about this
idea of trusting your gut. Hmm. Which, which I would
imagine must come from your just athletic background. I mean, because as much as, you know, baseball does rely on obviously individual achievement. Ultimately you're a part of a team, you're not a part of a team. Like it is you out there.
Yeah. And so you, I wonder if
that in part comes from, well it's just me out there, everybody else is sitting in the stands. I have to like, I have to be responsible for whatever happens next. Yeah. There's a lot of
responsibility on yourself. But, and, and so much of it is instinctual and you know, you can have
all the mechanic coaches and the physios and the fitness trainers, but when you're in the
tiebreaker in the third or fifth set, you're not
looking back at stats. You're not thinking of the YouTube videos that your coach showed
you before the match. You're just, you, you're relying
on your body, on your flow, on your mindset to let you get to that match point and win it. Yeah. So, yeah. But, but there is, even
though I didn't have that team environment, I did have a team that I relied on till the very last second until I walked on the court. And, and one of the things I
I miss till this day are those people, you know, that helped me win. That helped me achieve the,
the best things. And yeah, I Maria, I'm gonna talk about you to Jason in front of you. Oh ****. So Jason, I gotta tell you and, and our friends at home that we've had a couple calls on businesses that we were looking to invest, her family office and mine. And we had mutual interest
and we both passed. But I gotta tell you, when
you have such huge stars like Maria, a lot of times you
expect the zoom call maybe for them to come in a little late or maybe to have a couple
handlers or team members. She was the first one on the Zoom call. She was there by herself. She was taking notes, she was
asking the smartest questions. I was blown away. You were so blown away, you didn't call me back for any other deals. Where are those other deals that you want me to look at? That's a good point.
I owe you. I owe you. He owes you multiple deals after. I know he was giving me a
compliment and I shut him down. I'm sorry.
Yeah yeah But I think that's where I think when, when superstars in anything
they do, when they're able to pivot, the one thing
to be careful for is because you were so successful, things can actually go wrong in business. Yeah. And I thought she was a
perfect balance of optimism, but yet, you know, some reservation and the questions that she asked, I was incredibly impressed. And that made me understand
a little bit about your greatness over a 30
minute zoom call. Yeah
Thank you. But I'm a products person. Like, I love, like if
someone says, invest in this, like there's no reason this is gonna fail. I'd be like, send me the product. Here's the address, and don't
contact me for four weeks. I wanna live with it. Interesting.
I wanna breathe it. I wanna try it, I wanna
wear it, whatever it is. Like I want it. And I wanna, and I wanna
give it to my friends and I want them to give me their feedback. I wanna give it to my family
who have different tastes, who have different, you know,
appreciations and aesthetics. And until they tell me that they like it and they're into it, I won't
have a next call with you. One of the things you,
you guys have in common is during your playing
days, you're still like, you're thinking about your business, you're thinking about
your brand increasingly, especially as you go along. And yet at some moment, you're
not on the baseball field. You're not on the tennis
court anymore. No. What is that moment like when, like, what's the first day like when
you wake up after retiring and you sort of have to look
at your next life at You know, age of 30 what, 2, 2, 3, something like that. I, yeah, I remember that that day. Clearly I went skiing and it
was, I was pretty bad at it. I thought I'd have more
coordination than I did, and then I thought I'd get better at it. And then we're all stuck,
stuck at home during Covid and, you know, living a very
different life for, for, for several months. But look in, in all honesty, it's a big, big decision when you,
you decide for yourself, for your team, for your
family, that this is the end. And I was ready, my body was ready. It was challenged for several years. And stubbornness that
once propelled me to, to greatness eventually I
think was getting in the way of, of better things. So I was ready to say that I was ready for the next chapter is an understatement. I was ready to have a family.
I was ready to be a mom. I was in a good place mentally. I had a good outlook on life. But it's not like you just
turn the switch and move on. Like everything that you've built, the great thing about moving
to the next chapter is that you've built a foundation. Now, maybe it's a
completely different world. And I know, you know, we say sport and business, yes, there's
a lot of alignment, but there are many differences. And I couldn't forget the fact that over so many years I built a phenomenal foundation of strength, of resiliency, of focus, of determination, and all these apply to business. So today, you know, I
sit here in this chair and yes, I'm an investor. I'm on several boards, but I also can't take away from the fact that it took me more than 12 years to become great at one thing. And it takes time to build, you know, strength in another arena. So while I do have the
foundation, I'm still growing. I'm still learning. You know, I still wanna be better on my way here. I talked to my mom and she
said, you know, the, the, the educator in her, I
told her this morning, I was going on a podcast. She didn't ask too many questions, but she called me back
'cause I was in the car. And she said, you know,
I just wanna make sure that you're not just
talking about your career, that you have like, other things to offer and other things to say. Like, are you reading enough? She, she actually asked me, are you reading enough? Really?
On my way here. Yeah. So that I would have
other things, you know, to say beyond just sport. I was like, mom, yes, I'm,
I'm actually listening to the All In podcast
while I'm on my way here. Like, I'm still curious.
Don't worry. So, yeah. So think thinking about that, th there's gonna be viewers
that are watch this, that are founders that have a business that their dream would be for Maria to invest in their business. Can you tell us a little bit about how you think about businesses? Which sectors kind of broadly check sizes? How do you think about being
a value add investor? Yeah, One of my first investments, actually the first investment
was into a sunscreen brand called Super Goop. I was a user myself, and
this was 12 years ago. I knocked on the, on
the door of the founder and I said, I love your product. It's the only one I can wear while I play. It doesn't run in my eyes, it doesn't burn my eyes or sting them. Can I please help you out? I don't know what stage you're at. I don't know how young or old you are, but I love what you're doing and from what I've read,
I love your mission. And that was it. And two years ago they
sold 75% of their stake for close to a billion dollars. So it was my first, it was the first time where I didn't take that
paycheck at the beginning. And I said, let me invest,
let me give you my time, my platform, my voice, and help share this message
about preventing skin cancer. And that was a successful example. And there's been, you
know, several others not. So, but the point is, is that it came from loving the product. It came from the mission
that the founder had, that I resonated with, and
the fact that I could help it. Like I was realistic that
I had the right platform and that I had the right usership in order to help them grow. So I think all that was, it
was a good foundation in, in my investment story. And not to say that there's something that I may not be familiar with or that I'm taking a chance on. I, I still should take the call. I still should spend
time with the founders, but ultimately I wanna have
a good feel of what this is. Right? I, I wanna spend time, I wanna have dinner with
these people, right? Like, and I wanna win with
people that know how to lose. Like if you're, I can, you
know, sip champagne or, or you know, buy the glass, whatever it is when you're winning. Like I know what that feeling's like, but when things are not going
well, when you're losing, when you have a losing
streak, can be a year, can be a few years. And who are those people that
in are in that process, right? What's their mentality? How are they helping bring
back, you know, the, the fire and the team and the
product and the branding. So I, I wanna believe in
people that know how to lose and how that will
come up and find ways to win. I mean, one of the things that, that I feel like you're spending more and more time thinking
about too is this notion of, and and certainly this is
something that will resonate with you, Alex, this notion of
high performance, this notion of like, working under pressure. Yes. I mean, I'm, I'm sitting
in between two people who, Who love pressure Who love pressure, I mean,
who like, you know, like beyond thrive on it.
Yeah. How do you translate
that though into a life that doesn't have such clear winning and losing on a like
minute to minute basis? Well, it's, it's acceptance that it's not always going to go well. No matter. You might
have the best intentions, you might have the strongest preparation, the strongest mindset, the best team. I always say you have to be realistic. You, you can be confident, you can be underplaying your results, but you, you still have
to go out and show up. And sometimes it's things
are out of your control. People say certain things,
you don't like it, go home, do your job, keep working,
you'll get the results. So acceptance is one of them. Work ethic, I mean, work
ethic from a young age, understanding that nothing comes easy. You know, I, we both come
from humble backgrounds. And when, you know what
that feels like, I mean, I'm not a big spender. I take like, I know what's in my bank. We go as a, as star athletes, we go through these like moments of,
you know, fame and spending and you kind of lose
track of what you have. I thankfully didn't go in that direction. I was very, you know, had a purpose and how I spent, what I spent, like, I, I counted like little
coins when I was young. And I, yeah, I would still
count them if now we have to do those cyber coins. Turning it on on you. I mean, this whole notion of like pressure to business, I don't know. I mean, you, how do you get that same, You know, it's funny,
you know, the same charge. I think athletes, Maria and I and our colleagues get a bad rap about being bad business people. But I actually think that we have the greatest preparation to be really good at business. If we can check our ego, if
we can surround ourselves with better people than us
that have complimentary set of skills, that have an aligned vision, but the work ethic, the passion, not punching a clock from nine to five, we're just gonna do it till the job is done, even if we have to work around the clock. That is something
that I always underscore because most people
really are, and it's okay. They're not willing to pay that price. So we have a tremendous track record. We're persistent, we're we're resilient. And here's the biggest thing
I think in business is we understand how to deal with turbulence. Yeah.
And public noise. And, and that I think Jason
is one thing that a lot of people can give great advice, but when there's a bad article
about them, I mean, they, they literally melt in
the kitchen. Yeah. I mean there are some,
some significant stats about, you know, whether you
Fortune 500, you know, female CEOs, 80% of them have had high intensity sport background. Right. Whether it's in college, high school, league level. Why is that? Because
of the amazing lessons that you learn along the way. The resiliency. What do
you do under pressure? How do you cope with it? How
do you take care of your body? I mean, like, when you have
a big event, like it's easy for me now to say, oh,
I can go and have dinner and have a big curry, but actually if I really wanna be prepared and for my mind to be fresh,
I'm gonna have a lean dinner. 'cause I wanna wake up and I want my mind to be ready to go. So strong body, strong mind. And those are so many of the lessons that you learn as an athlete.
Yeah. I wanna ask one question 'cause I'm sincerely intrigued
by, by your answer here. You know, you talked
about, you know, coming with your father, mom had to stay back, check in IMG in the
middle of the night, motel, and then Wimbledon happens at 17 and your world starts
changing from a global place. Now you're in your mid thirties, right? And you have a little one at home. What is your North star when
you're 45, 50, your next, this, this business career is gonna be much longer than your playing career. You know, God willing, what
does a Wimbledon North Star look like for you in business? Yeah. Well, I don't look so far
ahead. I don't look at 45. I don't look at 50. The biggest difference and, and the biggest shift in my
life is when you have a child, the free time changes. Even when I was at the
top of my sporting career. Like, I had free time to recover, right? To rest my body, to be
curious about other things. Now, as a mother, if I can be honest, when even if you do have free time or you're not in the same city, you're on a trip, you know, a working trip, vacation, whatever it is, your child is not there. You're thinking of your child. Right? You're doing everything you can. So that juggle has
definitely been an adjustment for me. Business wise, there's a platform that I'm working on and developing that will take time. But as I said, I'm not in a rush. And I recognize, I
realize that everything that I've built for my tennis
career was built upon years and years of work and ups and downs and it will in my business career. But I'm, I'm curious, I'm
not afraid to take chances. I'm not afraid to take on roles that might be intimidating. I mean, I'm on the board of Montclair and I sit, you know, in
an Italian conference room with a translator in my ear because it's a officially public trading Italian company. So it has to be done in Italian. And it's intimidating. I mean, some of the figures,
the numbers, the decisions that you are responsible
for in that room are, you know, are high stakes. And so, you know, I feel, I feel like I have responsibility to know what the hell's
going on in that room. And so by doing
that, by putting myself in that situation, you know, gives me a, I'm a little scared. It's new, but I have to be prepare for it. And I love that work. Maria, I've heard you talk
about strategy and vision, and I think we share that in
as athletes, we do always have to have a strategy and a vision. When I thought about life after baseball, one of my north stars, that I would be
embarrassed to tell people, 'cause you're probably
not gonna get there. Right. Your North Star is something that's hard to share. It was team ownership. Right. And I'm having so much
fun with the Timberwolves and now my North star to
bring a world championship with my partner Mark Lore, to Minnesota. Any ambitions? And I see more women now,
which are so exciting, are getting involved in team ownership, WNBA,NBA, football. Any ideas in the future
you'd like to be involved? It's a hot topic, and if I can be completely
honest, I'm not someone that is oriented, my business decisions aren't
oriented on what's hot and what's trendy. There's a lot of talk about
being, you know, a co-owner of a league. I mean, whether it's
pickleball or, or padel or, you know, a female soccer team. I do come from individual
sport background. And so I do believe in the
power of, of an individual and raising and bringing the stories out of these impactful individuals. I've loved the conversations
around powerful females, but I do still think they've
been in the context of, of leagues and media rights and not necessarily what
these athletes are about. So I see my, my involvement
more in the individuals as opposed to the leagues right now. You know, one of the
interesting things as, as we start to wrap up, I would be
remiss if I didn't talk to you or if we didn't ask you about tennis. And I have to say, it was so
cool to see a different side of you in Breakpoint, you know, as sort of a luminary of the sport, kind of. I I mean, if you blinked, you'd miss me. So you must have not blinked
during that show. No, I don't think so. I feel like you popped up at
like very opportune times, but, but I did, you know, in in part because, you know, we did
get a taste of it there. I mean, I did wanna
ask you, I mean, tennis as a business is at
this fascinating moment. It feels like, in terms of, I
mean, you've been a part of, and you've witnessed
generations of tennis players. We are at a generational shift yes. On both the women's and the men's side. You know, there's new
investors coming into the WTA, there's talk of WTA and ATP merging. Yep. Like what, as a business person who has more than a passing interest. In the game of tennis. Like what do you see happening there? The schedule and the system
is still slightly broken. There's so much going on. This season is 10 months out of the year. There's several different
federations involved. There are the grand slams that are not connected to the rest of the tour. There's inequality. I mean, we could spend a whole
nother hour on the state of where the game is, but the bottom line is that
the actual faces and the names and the characters and the athletes that are
coming out from this new generation are spectacular and
they're gonna lead the sport. And that's what, that's what excites me. And, and to break point, it was actually the first tennis interview that I had done since retirement. And so it felt, you
know, tennis was something I, I will always know and I
knew for so many years, but it was nice to have a little bit of a, of a healthy distance from it. And so when I went into this and recording for Breakpoint
it, like it opened up so many, you know, cans from my past and my present and reflection where I felt
like I could commentate on it. But I wasn't like, involved and it felt so good not to
be part of any, of anything of what was going on. And to share my vision. And I think that's what was
reflected in, in what you saw. Yeah. I still don't think
it was as great of a impact to what they did with Formula One. Yeah.
But tennis is a tricky sport to unbox. There's so many layers. And, and that's what I mean
by, you know, the schedule, the equipment, all of
these things are tricky. Their players are hurt
for a lot of the season. You're not, you're at one
of the biggest events, but not all the top talents playing. Like, what are the reasons? So I like to get in before I look at who's
investing in what. All right. Do you have anything else you need to tell us? Oh God. Well, you, you started, you started with a hard ball. I mean, you asked me to
introduce myself. I was like, ****, well
this is not gonna go down. Well, because I wasn't
prepared for that one. What's your question for him? When are you gonna call
me on your next deal? I'm gonna call you. I'm
gonna definitely call you. Yeah, I wanna, I wanna
Yeah, what's the deal I wanna see the, I
wanna see the Rolodex. Yeah. I wanna see what deal
you guys would do together. I'm intrigued by the
I'm intrigued by the platform that you're,
that you're building. I wanna be part of that.
Okay. Wow. Real deal's happening right here on The Deal. We'll come back and
announce something big. Yeah,
Exactly. Just make sure your business manager wires the checks. That's a good point. I wire my own checks now. Okay. Perfect. Lesson learned.
Yes. Exactly, Maria thank you so much. This was fun.
Thank you
