September 3, 2026 • 47 mins
As the U.S. Open gets underway in New York City, the tennis world is abuzz to see the Williams sisters back on the court. Serena Williams’ return to the Open’s doubles tournament got us thinking back to an earlier episode of The Deal, recorded shortly after her retirement from the sport when she had moved on to the world of finance and started her own venture capital firm, Serena Ventures. We revisit that conversation, with Williams telling the hosts how she thinks about the “business of Serena” both on and off the court.
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Speaker 1 (00:02):
Bloomberg Audio Studios. Podcasts. Radio. News. Welcome back to The Deal.
I'm Jason Kelly.
Speaker 2 (00:14):
And today, a very special episode, a rerun of our
2024 conversation with none other than.
Speaker 1 (00:20):
Serena Williams, the GOAT.
Speaker 2 (00:22):
It's a fascinating time to re-listen to this because she's
back in the world of tennis as a player. She's
playing doubles this week with her sister Venus back at
Arthur Ashe Stadium, back at the Billie Jean King Tennis
Center here in New York City.
Speaker 1 (00:39):
It's the most wonderful time of the year.
Speaker 2 (00:41):
And Serena's getting back to tennis in sort of an
unexpected way. In the intervening years, she's only built her
business portfolio more and more I actually got a chance
to catch up with her again earlier this year at
the Milken Conference out in Los Angeles, and her ambition
remains massive when it comes to business. As I thought
(01:02):
back on this conversation that Alex and I had a
couple years ago, it was fascinating to hear Serena talk
about the early business decisions she made, many of them
that her father, Richard Williams, he really put a lot
of responsibility on her shoulders at a very young age.
She tells a great story, which you'll hear in this
(01:22):
episode about her earliest endorsement deal with Puma literally being
at the table and the conversations that ensued there. And
she's only taken it higher and higher from there. So
a great time now that Serena is back in our
lives in a tennis sense to relisten to this conversation.
Speaker 1 (01:39):
On the deal. All right. So please introduce yourself.
Speaker 3 (01:54):
All right. Well, that's I never really get asked that.
I mean, you asked me to come here. So, you know,
I'm Serena. I like to go by Serena. And what
else am I going to say that's really putting me
on the spot?
Speaker 1 (02:09):
How do you how do you describe yourself these days?
Speaker 3 (02:11):
How do I describe myself? I describe myself first as
a mom. I'm a mom. I'm a businesswoman and I'm
a free spirit. We'll go with that.
Speaker 1 (02:20):
You know, this this notion of.
Speaker 2 (02:22):
Reflecting on what you did as an athlete, as you
look back, you know, half a billion dollars in earnings
over the course of your career, how does that feel
as you embark even further on your business career, that
sort of financial success in sports?
Speaker 1 (02:39):
Yeah.
Speaker 3 (02:39):
You know, when I started tennis, first of all, I'm
from Compton, California, and I remember playing on these courts
and you know, my life was great. I never felt
like I needed anything, you know? And so for me,
money was never a motivation. I remember when I first
started back in the day, they used to write out
checks after you won your tournament and I would always
(03:01):
forget to get the checks. So at the end of
the year, they would always have to say, Serena, we
have all these checks for you. I'm like, oh my God.
Speaker 1 (03:07):
So it was never- You would literally forget to pick
up the check?
Speaker 3 (03:09):
Literally. And at the time I had an accountant who
would be like, Serena, like, they've sent me all these
checks that you would forget to get from the tournaments.
And so... So with that being said, that was never
my motivation, to be honest, for my motivation and looking
at the success that I had financially was never my
starting point. My starting point was always like, I just
(03:30):
want to win championships and I want to have fun
and I want to be a great tennis player. And
quite frankly, I just wanted to win a grand slam.
And I honestly, for me, everything else was a bonus.
And obviously it's great. Like, you know, I really, everything
that I have, believe me, I worked really hard for it.
Nothing really came for free and nothing came easy. Like
I think everything, was super hard working for me. But
(03:51):
it is cool to look back and see the success
that I've had financially, but also multiplying that now and
trying to expand that. And then again, just considering like,
what does that mean for me going forward?
Speaker 4 (04:04):
So Serena, when we were thinking about this show, I
started thinking about people that I like, respect, admire in
the world of sports, in the world of business. And
we had a business call recently and I said, would
you come on our show?
Speaker 1 (04:15):
Yeah.
Speaker 4 (04:16):
But I'm interested to know what motivates you today.
Speaker 3 (04:20):
When you're used to being a champion, you're used to winning.
And so that's something that I'm always motivated by is success.
And what is success? I think success is different for
a lot of people. And I think that's one thing
that I think a lot of people get wrong about.
For me, success right now is having great investments. I
think a lot of people's success is being a mom,
(04:42):
which is super successful for me because that's something that
I've always wanted to do in my life. Or maybe
it's getting an A on your grades or whatever that is.
So I think for me, the motivation is definitely success.
Speaker 4 (04:54):
Both of us played for a couple of decades, right?
Very public. Me more domestically, you more around the world.
But what's interesting is, Jason, you mentioned half a billion dollars.
you know, for me, it was about the same thing,
but 90% of my money came from playing baseball on
the field with you is exact opposite with yours is marketing.
(05:14):
How do you think about the impact that you've made,
not only to all your partners, but how the ripple
effect around the world of the business of Serena?
Speaker 3 (05:22):
Yeah, it's so different, right? I think it's really interesting
how I learned early on that your paycheck from tennis,
maybe that's why I forgot them, should be your smallest earning.
That's what my dad always told me growing up. So
I always thought, okay, well, you know, partnering with the
right people and also deciding who do you really want
(05:43):
to partner with? Because for me, it's also about being
very authentic with those partnerships, not necessarily partnering with a
company that, either doesn't believe in what you're doing or
you don't really use and utilize. So I think throughout
my whole career, I wanted to make sure that those
partnerships are very authentic. They spoke to me and they also,
(06:03):
you know, gave back in some sort of way, shape
or form.
Speaker 1 (06:07):
So fair to say your earliest business advice came from
your dad?
Speaker 3 (06:11):
Most of my business advice came from my dad early on.
He is incredibly, incredibly smart. I think he is way
before his time, everything that he did. I think even
when it came to marketing us as tennis players, tennis
is a very expensive sport and you can't make it
from Compton. But I think it was his marketing that
got us that attention, that garnered those press articles that
(06:33):
had reporters coming out or else we would have a
very difficult time getting out of that in order to
make it. But because of the way he thought about
it and because of the way the social media wasn't
a thing back then. So because of the way he
was getting that attention and it was able to push
us up to the top. Obviously our wins counted as well,
which helped keep us up there in the early ages,
(06:55):
like around the junior stage. But he always was way
ahead of his time when it came to marketing and
advice and business advice. And early on, he was like,
you know what, you're going to manage your own money.
Like literally, my first checks from whether it was Puma,
like I got these huge checks. He's like, you figure
it out. And so we had to figure it out.
(07:15):
I'm literally living at his house in the bedroom next
to Venus.
Speaker 4 (07:20):
How old are you at this point?
Speaker 3 (07:21):
I was 16.
Speaker 4 (07:22):
Wow.
Speaker 3 (07:22):
And he's like, you know, most parents, you know, they
take your money and they take something. But, you know,
he's like, you figure it out. And so I remember
having to figure that out and having to learn how
to manage from a very early age and not get
crazy with it. And so he he empowered us to
do that.
Speaker 2 (07:41):
You've said that wasn't as much about the money. It
was about validation and putting you in a position to
be in control in a way that you weren't before.
Speaker 1 (07:50):
Take us back to that moment. That's a fascinating deal.
Speaker 3 (07:53):
Puma is an incredibly fascinating deal. My dad negotiated everything.
And I have to say, Puma was probably about the
money a little bit for me. It was a lot
of money. I remember I was 16 years old. I
had an opportunity to be with other companies, but they passed.
And so... There was this deal that Reebok wanted to
do with me and Venus combined. And my dad and
(08:15):
my team was like, we're not going to do this.
We're not going to package Serena with Venus because she's
going to be amazing. Thank God that we didn't do that.
So we went to L.A. Arnon Milshan at the time
was one of the biggest shareholders in Puma. We're all
in Hollywood. He also is like New Regency and was
producing all these films. We're in this Hollywood studio, walking
(08:38):
in the hallway, all these famous movies like Pretty Woman
and all these posters are on the wall. And we
sit in this conference room and we negotiate. And it's
like literally midnight. I'm 16. My dad's negotiating. They're going
back and forth. And he wants me there for the
whole time to make sure I know everything.
Speaker 1 (08:55):
What to do in the future. You're literally falling asleep
at the table.
Speaker 3 (08:58):
I pass out. I'm not falling asleep. I pass out
at some point.
Speaker 4 (09:02):
Wow.
Speaker 3 (09:02):
You know, I eventually wake up and they're still at
it and I'm just so upset. But what a learning experience.
I learned so much from that experience. And ever since then,
I'm usually behind the scenes. I don't do the negotiating,
but I actually am behind the scenes. But no one
really knows that it's actually me. It was my agent
or whoever. If they get a deal, they come to
(09:24):
me and they say, what do you want to do?
And I tell them exactly what to do.
Speaker 1 (09:27):
Yeah.
Speaker 3 (09:27):
They obviously deliver the message, but it's super connected. We
have such a great relationship when it comes to negotiating.
They really trust my advice and my vision and where
to go with it. And it all started at such
a young age. But I also learned from that to
ask for equity because I didn't at that time, which
I probably should have. And then I ran into Arnon
a couple of years ago and he's like, yeah, you
(09:48):
should have did equity. I'm like, thanks, Arnon.
Speaker 4 (09:51):
I was 16.
Speaker 3 (09:52):
You know, you should have said it. And he's like,
no way. I'm like, okay. But it was... Also a
really good opportunity to see how you can amplify a
complete brand and what, you know, I was able to
help amplify that brand a lot.
Speaker 1 (10:05):
Because there was a little bit of risk on both sides.
Speaker 3 (10:08):
It was.
Speaker 1 (10:08):
It was.
Speaker 3 (10:09):
I was the younger sister at the time. No one,
you know, understood that You could have siblings that play
sport and they can both be great. And at that point,
it was always just one or the other. And so
Venus was an amazing athlete. And so it was like,
you know, they can't be possibly be another one. So
it was a big chance for Puma. But also I was,
(10:29):
you know, doing really amazing things and winning. And I
won a Grand Slam less than a year later. after signing.
Speaker 1 (10:35):
So not a lot of risk for them, not a lot.
Speaker 3 (10:37):
Of risk for them really. But, uh, and I think
they saw that it was a lot of potential and
they saw it early on.
Speaker 4 (10:44):
I remember, I don't know a lot about tennis, you know, Well, good.
Speaker 3 (10:49):
Because I don't know a lot about baseball. I know that.
I already know that.
Speaker 4 (10:52):
But we already know this. This is more for the audience.
But one of the things, I remember when I was
like 25, 26, I always used to remember you, not
for your great plays, but for your fashion.
Speaker 1 (11:02):
Oh, yes.
Speaker 4 (11:03):
And I just thought, like, I wanted to see what
Serena was wearing that day. Really? Awesome. Yeah, with her
skirt or her dress and what Puma is. And I
just thought that, and then the Anna Wintour connection, what
is it about fashion that, motivates you because you've always
been on point.
Speaker 3 (11:17):
So you know my mom used to sew our outfits
when we were younger and i remember some of our
earliest tournament outfits my mom used to make and so
she would be cutting patterns and at the time they're
called these vogue patterns out And she would put them
together and she would sew our tennis outfits or some
other school outfits or whatever. That's always been a natural
(11:37):
attachment to fashion. And eventually I learned how to sew
and how to make things from old socks. And then
eventually I'll use old clothes when I was literally living
in Compton and just learned how to do the craft. Right.
And that's kind of how it started. And eventually I
went to fashion school, which is a whole story in
its own. I feel like I have a zillion stories, but.
Speaker 1 (11:58):
We're here for them, by the way.
Speaker 3 (12:01):
How much time do we have?
Speaker 1 (12:02):
As much as you want.
Speaker 3 (12:04):
It was going to have to be like a two-part session.
Speaker 4 (12:06):
There you go.
Speaker 3 (12:06):
And so then, yeah, so eventually I went to fashion
school and then One thing I did love when I
first came out with Puma is they gave me like
a lot of opportunities to design some of the stuff
that I was wearing or at least say like, this
is what I want to wear. And I knew that, listen,
I don't look like everyone else out here. I don't
play like everyone else. And I'm different. It's clear that
(12:28):
I'm different. I am a black girl and I'm playing tennis.
And so I need to stand out. I don't want
to wear the same kind of outfits that everyone else
was wearing because And so Puma understood that. And then
that kind of started the craze. And obviously Nike came
on right after and just amplified it times a zillion,
which made it even more cool, like which made me
wear like a jean skirt in New York, which was
(12:51):
kind of one of my favorite outfits. It was insane.
I still can't believe I did that. Yeah. I should
have won that year. But anyway.
Speaker 2 (12:57):
But let's talk about some of those specific fashion choices.
The one that I think so many people remember is
the catsuit.
Speaker 3 (13:04):
The catsuit was legendary. Yeah.
Speaker 2 (13:06):
And so like, take us back to that moment, like
that choice. Like, how does that feel? Like when you
put that on, because you have said, I love this
quote from you. It says, when there was an edge
to how I look, there was an edge to my game.
Speaker 3 (13:19):
Absolutely. So that choice was definitely a Puma designer. And
she was like, we want you to do this catsuit.
And I was like, whoa, this is crazy. This is
so cool. So the U.S. Open came and I put
it on. I was like, I'm not doing this. And
I took it off. I was like, I can't do this.
I can't do this. And so I had a second
outfit in case I didn't want to wear the catsuit,
which if you look at the Open in that year,
(13:40):
I think it was 2002, I actually wore the second
outfit in the second round. But I was like, no,
I can't do that anymore. I need to wear that.
I need to own this cat suit. I need to
own it. So, yeah, it was just a really wild experience.
But anyway, I took it off and I was like,
I can't do this. And I'm like, I need to
focus on my game, not on my outfit as I'm
walking out on the court. And I'm asked a few
(14:01):
girls in the locker room what they think. And they're like, oh,
that's crazy. You can't wear that. You can't wear that.
And I'm like, oh, I know. I know. And for
whatever reason, right before walk off, I just changed really fast.
I threw the catsuit on. I zipped it up and
I just walked out. It was like, oh, my God.
And then it was just it was no looking back
after that, really.
Speaker 1 (14:19):
So did it feel interesting? as important in the moment.
Speaker 4 (14:23):
It didn't.
Speaker 3 (14:23):
Okay.
Speaker 1 (14:24):
You didn't know.
Speaker 3 (14:27):
I always say that's how, that's when I got famous.
It wasn't the six grand slams I won before that.
It was a catsuit.
Speaker 1 (14:34):
Yeah.
Speaker 3 (14:35):
I mean, I was pretty young and, and again, there
was not a lot of stuff around body positivity at
that time for a body. They looked like mine in
sport because every woman at that time was Not every woman,
but a lot of women at that time had a
different type of figure than I did. And so I
was really different. I was basically a lone soldier and
(14:56):
it was just me. And even my sister looked like
the typical athlete that was just amazing and long and lean.
And I was just totally different. Yeah. And so it
was without knowing it was really leaning into that. And,
and again, I didn't know I was just doing it.
And then it was a lot of memes, even before
memes were memes.
Speaker 4 (15:17):
You looked amazing.
Speaker 3 (15:18):
Okay.
Speaker 4 (15:18):
I remember, I mean, at that time it was no Instagram,
but you broke the internet. It was Google everywhere. And
I remember a lot of my teammates and buddies from
back home sending me the picture saying, look how fly
she looks.
Speaker 5 (15:28):
Right.
Speaker 4 (15:28):
But in baseball, Jason, it sounds like it's the same
thing in tennis where you look good. You feel good.
Speaker 3 (15:34):
Absolutely.
Speaker 4 (15:35):
You play good.
Speaker 1 (15:35):
Yeah.
Speaker 4 (15:36):
And I love that because that's exactly how I felt
as a player.
Speaker 3 (15:40):
Absolutely.
Speaker 1 (15:41):
But I think we shouldn't underestimate the cultural power that
that moment had.
Speaker 3 (15:48):
And it crossed so many people that weren't watching tennis.
Speaker 1 (15:52):
Right.
Speaker 3 (15:52):
People outside that were OK, maybe in Compton because we
were from there, but like every neighborhood at that point.
But it just crossed all borders and it made people
from all walks of life want to just kind of
watch tennis. And it was just like being that cultural
person to bring in people that don't normally watch the sport. Again,
(16:13):
I didn't understand at the time, but seeing later on
and even the people that started playing tennis after that
and the people that are currently playing because tennis of
myself and my sister, it all started at these moments.
It's crazy to think about. I've never even voiced this stuff. Like,
oh my God.
Speaker 1 (16:30):
But that, I mean, it changes the business of tennis.
Speaker 3 (16:33):
Absolutely.
Speaker 1 (16:34):
Also changes the business of Serena, right?
Speaker 2 (16:36):
I mean, it elevates you because again, I feel like
we need to keep stating, it's a given what you
were doing on the court, but the impact you were
having off the court just becomes magnified to your point.
What does it feel like as that is starting to
take root?
Speaker 3 (16:54):
It definitely feels different as that starts to take place.
There were more contracts and more deals coming in and
more time. But that's what it is about, right? Again,
I'm thinking I was told when I was really young
that you make your money off the court. Tennis should
be your smallest check in our sport at that time.
And so... I'm thinking, okay, this is, again, this is
(17:16):
what my dad was talking about. Like, how did he know?
And so, and then it was also leaning into these
designs even more after the cat suit. It was even
more about leaning into that and how will I want
to make my impact? I think that's about the time
I started going to fashion school and trying to understand
how did I want to make my impact off the court?
Because it was always about having a plan B, even
(17:37):
though I didn't necessarily need it, but it was just
something etched in my head. My dad- You could fall.
Anything can happen. You could break your ankle. You have
to have something to fall back on. And so all
these moments in the back of my mind are like, OK, well,
this is something that I can kind of do in
the future.
Speaker 2 (17:58):
Coming up, Serena talks about how she got into investing,
how she signed with Nike and how she met and
works with her husband, Alexis Ohanian.
Speaker 4 (18:19):
I remember a story with Phil Knight. And I was
with Nike ever since I was 17 years old. And
we had Ken Griffey Jr. on our team. And at
the time, he was like the Michael Jordan. And I
was telling Uncle Phil, like, I want my own shoe,
like Griffey. And at that time, we had Jordan, we
had Griffey, and that was the gold standard. And I'll
never forget, we went to breakfast on a Saturday morning
(18:42):
in Beverly Hills. And I said, Phil, when am I
going to get my own shoe? And he says, Alex...
If you get to a primary market, at the time
I was in Seattle, I would redo your deal and
I'd rewrite your contract. And I said, well, define a
big market. He said, New York, LA, Chicago. I said, okay.
The day I got where George Steinbrenner called me and
traded me to New York, I got a call from
(19:04):
Phil Knight and he said, game on. And because of
his loyalty, no contract, just a handshake. I've been with
Nike ever since. I've never worn another shoe. But when
I got to New York, I sensed things were different.
the impact, all the opportunities that came. When did you
feel that things were different and that whatever brand you
went with actually had a ripple effect, not only domestically,
(19:26):
but around the world?
Speaker 3 (19:27):
Yeah, I think things got really different. I, I do remember, actually,
now that you mentioned it, I actually forgot about the
Seattle Mariners.
Speaker 4 (19:36):
Yeah, there you go.
Speaker 1 (19:37):
She's a baseball expert. It happened right here.
Speaker 3 (19:40):
But I definitely remember you more in New York and
how that that whole world kind of exploded after that.
But for me, I feel like everything changed after that
catsuit and not because of the catsuit. I think it
was me winning the French Open, Wimbledon and the U.S.
Open in the same year. It has been years and
(20:01):
years and years since anyone had done that. and winning
those three Grand Slams in a row. And I have
to say, at the time, there was so many great
tennis players. There was Lindsay Davenport, there was Martina Hingis,
there was Venus Williams, there was Monica Sellis. And to
dominate at that time with Everyone that was so great
was just unheard of. And so I think winning that U.S.
(20:24):
Open just solidified everything and the outfit. And it was like, well,
this kid is amazing. How do I change that? How
do I say, OK, tennis is great, but how do
I extend that and how do I expand that outside
of tennis? Just understanding that. pop culture and then get
invited to different things. And I would be like, oh, wow,
(20:45):
I'm at the Laureus Awards or I'm here and I'm
actually winning these awards. And, you know, except for the
one in LA, I'm still bitter about it. I'm not
competitive at all.
Speaker 2 (20:56):
The winning and losing thing is definitely not.
Speaker 3 (21:00):
Doesn't play with me at all.
Speaker 1 (21:03):
And so how do you take advantage of that?
Speaker 2 (21:04):
Like, what's the process by which, I mean, you've been
with Jill for a long time, Jill Smollard.
Speaker 1 (21:08):
Are the conversations different? Are your ambitions growing?
Speaker 2 (21:12):
Like how do you activate that moment where you are
blowing up even more?
Speaker 3 (21:17):
Well, Jill has been amazing. I feel like leaning into
having someone, a woman in that position, I think quite frankly,
maybe things would have been different if I had a guy,
like maybe I would have had an extra deal or two,
but it was really about leaning in into having a
woman on my team. Interesting. owning that. We got ours
(21:40):
when the time was due, when the time was ready,
but it was sometimes where we had to fight a
little bit extra. It's really just about really empowering not
only yourself, but people around you and your team as well.
Jill works at WME, amazing agent there. I don't even
like that word actually, but I don't know. I haven't
been able to find a different word for that.
Speaker 4 (21:59):
She's like your partner.
Speaker 3 (22:00):
Exactly. Like a partner.
Speaker 4 (22:02):
And how long have you guys been?
Speaker 3 (22:04):
Oh, since 2000. That's incredible. Yeah. It's been an incredibly
long time, but it really was important to be able
to expand and really start to think about what other,
what other things can you touch? What other things can
you do and how to go about doing that? So
then you have to work from a plan. And then
I would have a list. Like I want to be with,
at the time I wasn't with Gatorade. And I was like,
(22:25):
my lifelong dream was to be with Gatorade because I
remember walking around the corner from my tennis court, not
my tennis court, the community court in Compton. We would
walk to the convenience store and my dad would buy
one Gatorade in a can and we would all have
to share it. And it was like, I've always loved that.
And I've always loved that story. And I've always loved Gatorade. And,
(22:47):
and I would always see the mic. I want to
be like mic commercials. And I was like, I want that.
And so I would always, we would always come together
and say, what are some things that you want to
do in a corporate, if it was corporate, what corporate
companies you want to be with?
Speaker 1 (22:59):
And does that resonate with you?
Speaker 2 (23:00):
I mean, because I'm sitting between these two very deliberate
business people who have caught into this from an early,
I mean, do you remember identifying brands that you wanted
to be with?
Speaker 1 (23:11):
Because it sounds like you had a literal list.
Speaker 4 (23:14):
I mean, for me, Gatorade is another one because I
believe I was, I won the Gatorade player of the
year in high school. And I was like, oh my God,
that's so cool. That's the first big award that I
won nationally. And of course, I want to be like,
my campaign was huge. It still is to this day.
But for me, it was Nike. Nike to me was
the ultimate North Star because Michael Jordan wore it, right?
And we all want to be like those. I looked
(23:36):
up to Michael and Magic and Bird.
Speaker 3 (23:38):
Everyone looked up to Michael. A girl, a guy, whatever.
Speaker 4 (23:42):
Who did you look up to? Who inspired you?
Speaker 3 (23:45):
When it came to branding Michael, Michael Jordan, I think
he really was able to do branding in a different way.
And the aplomb that he has walking around is just
second to none. Tennis wise, I was actually inspired by
Monica Settles. I just liked her. I thought she was
really cool. And I liked how she grunt. I do
(24:08):
have a question.
Speaker 4 (24:08):
Was there a call where Jill called you and she said, hi, Serena,
we got this company and this is what they're willing
to pay you. And you said, what? they're willing to
pay me that much i've had moments like that but
i'm wondering if you ever had a moment like.
Speaker 3 (24:21):
That yes i've definitely had that and i'm like let's
start at yes but let's not seem desperate let's let's
wait at least at least an hour now let's wait
at least a few days to call him back.
Speaker 2 (24:34):
But And so let's talk about Nike for a second,
because obviously Puma does one thing.
Speaker 1 (24:40):
But as you've alluded to, Nike does something altogether.
Speaker 3 (24:44):
Absolutely.
Speaker 1 (24:45):
What was that negotiation?
Speaker 2 (24:46):
Like, what do you remember about sort of getting into
business with them?
Speaker 3 (24:51):
So I just remember I wanted to be with Nike.
I had always wanted to be with Nike from day one,
even before signing with Puma. I was wearing Nike just
because I would buy it. And then I would just,
you know, hopefully like sending some messages like, I'm your girl,
I'm your girl. Like, you know, hello. So that was
always a company that I've wanted to be with. I
(25:13):
think they have an opportunity to market, especially at the time.
It's just like, you know, if you want to be
the best, then you have to wear Nike. That was
seared in my mind. I wanted to be the best.
And I think the best They had the best stuff.
They had the best marketing. They had an opportunity to
put you, as we talked briefly, globally. And because tennis
(25:35):
is not just in the United States. It's Australia. It's England.
It's Italy. It's China. It's literally everywhere on the globe.
And I can think of just a handful of companies
that can reach that far. And so for me, I
wanted to reach that far and I wanted to be
with a company that could amplify that. And I'm not
necessarily amplifying them. I wanted them to amplify me.
Speaker 2 (25:56):
You talked about this moment in tennis that I want
to dwell on for a second, because you're right. There
are a lot of great players, but you very quickly
just overcome all of them. You did something market and
notable for the business of tennis, for viewership, for attendance,
for branding off the court. Was that apparent to you
(26:17):
at the time? Or is it only apparent in retrospect?
Speaker 3 (26:21):
No, it was very apparent because you would see matches.
If I wasn't at a tournament or Venus wasn't at
a tournament, the attendance was just different. And years that
I was injured....
Speaker 4 (26:34):
Oh, God.
Speaker 3 (26:36):
Or years that... Stay professional, Serena. Don't say that. Years
that I was injured or years that, you know... I
didn't play. You could just see the difference of, you know,
people that are, were attending the matches or viewers.
Speaker 2 (26:54):
The U S open is my favorite tennis tournament. It
is the most electric setting. And then it's like the
wattage is turned up when you walk out.
Speaker 1 (27:02):
That's just, again, that's factual. I have to say you
feel that.
Speaker 3 (27:06):
And I took on a lot of that pressure as
the years continued after 10 years, you know, I would
feel that pressure of like, okay, it's, is Serena going
to be in New York? And, you know, it's, it was,
it was like a, not the, not the Serena open,
but it was still like a lot of attention on,
(27:28):
you know, myself. Right. And Venus too, but it was
a lot of attention on me.
Speaker 2 (27:33):
Because the numbers are one thing and the numbers are great,
but what's the Serena effect on Serena? You know, like
that pressure in the, in the sense of, you know,
that if you show up, that's, better for tennis. That's
better for the owner of the tournament.
Speaker 3 (27:48):
I don't think that I try to always remain humble.
And I don't, I didn't go in the tournament thinking
that the US Open is still going on and I'm
not playing sadly, but, and it's still going to be
there with or without me. So I always had that
view and I always knew that. But at the same time,
I also did know that for this amount of time
(28:09):
however that's going to be it's going to be super
amplified and it's not easy but you do walk in
with your chest a little farther out in your head
a little higher because also you are a target you
know everyone right at the end of the day isn't
really happy that you're on the front page of all
these papers right and you know they're just like they
they want that and a part of me is like,
(28:31):
take it because it's a lot, it's a lot of
pressure and it's a lot to hold when you lose
is losing is way bigger news than winning. Like if
I want to match, it's almost last page and yeah.
But if it's, if I lose, it's like front center.
So you don't want that story. And so having a
lot of that pressure is definitely not fun, but it's
also a privilege, you know? And I think it's, I
(28:55):
would definitely prefer that pressure than not being If that
makes sense.
Speaker 4 (28:59):
Yeah.
Speaker 1 (29:00):
Pressure is a privilege. It's right there, right when you
walk out on the court, right?
Speaker 4 (29:03):
It is. Wow. It is.
Speaker 3 (29:03):
New York is your favorite tournament.
Speaker 2 (29:05):
Wow.
Speaker 4 (29:06):
But Jace, I want to segue to business because I
was on a call with Serena early on and I
was like, wow, I wasn't expecting that. And not because...
I had a judgment.
Speaker 3 (29:18):
Hey, wait a minute. No, I'll tell you why.
Speaker 4 (29:19):
I'll tell you why. Because the questions you were asking
were so thorough. You had done your due diligence. You
were asking things about, it has to fit with my brand.
And I knew you would know all the numbers, but
I didn't know how authentic you were going to be
and how sincerely, deeply in the weeds you would be.
Speaker 3 (29:37):
Too deep in the weeds we decided, right? Too much.
Speaker 4 (29:42):
But where does that come from? Is it from your
playing days? Attention to detail?
Speaker 3 (29:48):
I feel like, yeah, I'm super attention to detail. I
feel like I've always excelled at education and I love learning.
And so Yeah. So for me, when it comes to
my business, and like I said, I think we decided
I was too much in the weeds. And like literally
what he's talking about, like being on calls with founders
(30:09):
and actually helping founders understand like why their business isn't
working and why it's not successful. Or, you know, like
literally on every call, if we have calls every six weeks,
I own that company. So yeah. not own the company,
but I'm the representative for the company for my firm
as SV CERN Ventures. And so I'm like literally on
the calls. I'm literally helping them understand how their fundraise,
(30:29):
I'm looking at their decks. And so it's a lot.
So I decided, okay, that's too much. I can't go
on like this, but I truly love investing. And that's
one thing that I kind of fell in love with
from tennis. I would see these sponsors because tennis is
all sponsor based. And I would see like some of
these sponsors come up, but I'm like, well, I have
(30:51):
some little cash. Like, how did I not invest in Facebook?
How did I invest in Airbnb? Or how did I
miss Google? Or like, you know, all these companies. I
don't know if you've ever thought of that, but I'm like.
Speaker 4 (31:01):
I missed a bunch.
Speaker 3 (31:02):
How? Like, why? And I started to ask these questions. Like,
why am I out here breaking my neck? and sweating
when I could have invested in these companies and I
could still be doing the same thing, but I wouldn't
have to be such dire. I've got to win the
US Open this year. I've got to pay these bills.
(31:22):
So I literally would be on the court looking at
these sponsors thinking, how did I miss this? And so
I started asking questions and I went to, at the time,
San Francisco, Silicon area. Back then it was a super
boys club.
Speaker 5 (31:35):
Yeah.
Speaker 3 (31:36):
And I would ask questions. I remember even just sitting
in Pinterest at the time one day and just learning
from the founder there and just being a sponge and
just trying to understand the business, understand investing, understand all
this stuff a little bit more. And that's kind of
how it all started.
Speaker 2 (31:54):
Unfortunately, to your point about the Bay Area and underrepresentation,
still there. 2% of VC funding goes to women, even
fewer when you start to go to other categories of underrepresentation.
Was that part of the DNA of Serena Ventress from
the beginning?
Speaker 1 (32:13):
How did that all?
Speaker 3 (32:15):
Another story, if you guys want to hear it. We're
literally here for your story. So I started investing and
then I somehow got into early stage investing. I didn't
realize that. It was called early stage. I just liked
companies that were starting and then I liked growing them.
One of them was Masterclass. I remember meeting the guys.
(32:37):
David is one of the founders and it was a
room about this size, but this is all they had
and they didn't have anything else. And this is where
Masterclass was. And I fell in love with the concept.
I fell in love with what they were doing. And
I was like, I want to be a part of this.
And so it was just finding several different companies like that.
Then Masterclass obviously became Masterclass. And one day I was
(32:58):
at a conference at JP Morgan and Jamie Dimon was
on stage and he was talking to this woman named
Karen Seidman Becker. But she's on stage and she's talking
about women and VC and how women get less than 2%
of all VC money. And I'm thinking- She misspoke. That's
so embarrassing. Like, I'm embarrassed for her.
Speaker 1 (33:19):
Right, right, right, right.
Speaker 3 (33:20):
But that's how people should think about it. But this
is genuine. My genuine thoughts is that she misspoke. So
me being me, after she was done, I go up
to her and I'm like, hi, yeah, I'm Serena. And
then I'm like, well, you've said something on stage. And
I don't know if you meant to say this or
if you said the number wrong, but... something about 2%,
less than 2%. And she was like, you know, Karen.
(33:42):
So she's like the woman I dream of being. And
she's just like, tells me everything. And she just, Gives
me all this amazing information in the span of 10 minutes.
And I'm like, I didn't know. And so that's how
Serene Adventures happened. From that moment forward, I was like,
I need to start an investment company and I'm not
(34:02):
going to be able to change it. But the platform
can help other people talk about it and change it.
And so that's when from that point. three years before
I actually raised a fund. So I worked on doing
more deals. I ended up getting about 16 unicorns in
my portfolio. So that way I would have a good
track record because I knew it wouldn't be probably easy
for us to raise a fund first go around. Yeah.
(34:24):
Until you get to know me and you get to
know the story and you get to know all the
investments that I had done. And that's what happened.
Speaker 4 (34:42):
So Serena, as I hear you speaking, I can't help
but think about like when I transitioned from baseball to
business and it's quite daunting. And I know for me,
there was some imposter syndrome, but we're both former athletes.
I'm a man of color. You're a woman of color.
As you enter the world of capital raising, which is
very difficult, especially when you haven't had the track record
(35:03):
early on. How did that make you feel when you
went to LPs, potential LPs, to raise capital?
Speaker 3 (35:09):
It's a competition. I loved it. It's what I... It
gave me energy. It gives me life in telling my story.
And also, this isn't about me and it's not about
me raising capital. We are investing in women. We are
investing in people of color like that. Two percent is women,
people of color, women of color is less than a fraction. Right.
(35:31):
Like if I want to start a business and my
name isn't Serena Williams, I'm going to have to take
something out on my house. I'm going to have to
go to the bank like it's not I'm not going
to be I'm just going to not be able to
get VC money. But we're changing that. And we don't
only invest in women. We don't only invest in people
of color. But we're putting that on a platform. Our
portfolio right now as it stands is 68% women or
(35:51):
person of color. And that is unheard of in the
VC world. And so for me, it's all about diversity
and bringing everyone together. We invest in literally everyone. We
don't care what you look like. But we hear your
story if you're a woman. We hear your story if
you're a person of color. And a lot of people
that look like me don't even get their story heard.
And so when you do go to these LPs and
you genuinely tell them the story, if they pass, they pass.
(36:15):
But at least you get them thinking. You get them hearing.
And maybe they'll invest in another fund that is doing
the same thing. Maybe that has been around a little
bit longer with a track record a little bit longer.
But they'll come around to us at some point. And
that's kind of how I feel. But I love talking
to LPs and just getting that story told on a
platform that a lot of people don't have. And so
that is, it's super amazing for us.
Speaker 2 (36:36):
The barriers you and your sister and your dad broke
down when it came to tennis, does it feel like
there's a parallel to what you're trying to do in business?
Speaker 3 (36:45):
It does. And I don't want it to be. You know,
my daughter wants to do a sport and I'm like,
you have to do a sport that's, you're not breaking
down barriers because mom has already done that. And You
don't need to do that. And so somehow I find
myself in a similar story without trying. I think eventually
you're just drawn to, you know, whatever you're drawn to.
(37:10):
And without me realizing it, I was always drawn to
this space and it put me here and I'm not
going to change. I am taking a step back. I'm
taking your advice like, oh, my goodness, already done. But
the impact will always be there and the impact will
continue to be there. And I look forward to that.
Speaker 2 (37:28):
Your dad was a partner. Your sister was a partner
and now Alexis is clearly a life partner, but also
I'm fascinated. And I think Alex is too about, you know,
these two entities, these two business entities sort of coming together.
And I wonder, because it's apparent to us as we
look at it, the influence you've had on each other
(37:50):
in terms of investments, what do you think your influence
has been on him?
Speaker 3 (37:55):
Well, I think my influence on him is just, he,
really wants that success. He really wants to be seen
as that best investor. And he is, he's such a
great investor. And I'm like, you already have that, but
he wants it to be even more amplified. And also
(38:17):
just explaining to him and just giving him my insights
of you know, how to play the game. Because you
have to be able to play the game, whether you're
investing or whether you are in sport. It's who plays
the game the best. And some of the greatest businessmen
and investors play the game better than someone who actually
might be better and smarter. And with him, we met
(38:40):
because we were talking about investments all these years ago.
Speaker 1 (38:42):
That's how you met?
Speaker 3 (38:43):
That's how we met. Yeah.
Speaker 1 (38:45):
Oh, you got to tell us that story.
Speaker 3 (38:47):
Okay. You asked. I told you I have a lot
of stories. So I was in Italy at a tournament
and I'd been in Europe for a few weeks at
that point. And then when you hear an American accent,
when you haven't heard it for a few weeks, it's
like refreshing. And so all week at this particular hotel
we were staying at, There is these American people that
(39:08):
were here for a tech conference. And so anyway, so
fast forward to a couple of days later, I have
a match that day. I'm so focused when I play
a match. Like I literally would never leave the room.
I would watch film all day and I would be
in my room and it was a night match. And
night matches are extremely stressful for me mentally because I'm
having to be in the room from like until 6 p.m.
or 5 p.m. So I'm like, I don't want to
(39:31):
be in the room till 5 p.m. today for my chance.
I was like, I just can't do this today. I
just can't. So I left. to go downstairs at breakfast.
Now this is crazy. Like, come on. I mean, I
literally would even eat breakfast in my room. I would
never be seen. I was a ghost. So I went
to have breakfast.
Speaker 5 (39:46):
Woo.
Speaker 4 (39:47):
Wow.
Speaker 3 (39:48):
That's such a big thing. What it was in my world.
So I went downstairs and that was late for breakfast.
I didn't go downstairs to 11 cause I was just
fighting with myself. If I was like, I should be,
I should be studying. That's how hard I was on myself.
So I went down late, breakfast was closed and they
sent me to a different restaurant across the way, which
had like a pool and, And so I went to
this other restaurant with this massive pool. There's all these
(40:10):
chairs and there's all these tables and there's this pool
and there's another side of the pool, there's chairs. And
so we're the only people. It's me, Jill, and my
assistant at the time. And he was Australian. That's going
to come back too. So we sit down, the only
people there, and we order our breakfast and we're just
talking and laughing. This guy walks in with a computer
and he sits down right next to us at the
(40:31):
table right next to us. And I'm like, so upset.
I'm like, do you see how big this area is?
Speaker 1 (40:39):
Are you kidding me?
Speaker 3 (40:41):
Like, do I look, does it look like we want
people next to us? Like it's huge. And I'm like,
oh my goodness. So my assistant at the time, his
name was Zane. He's like, hello, mate. There's a awful accent.
Ozzy accent is the worst. There's a rat over there.
And He's saying that there's a rat. There's a rat.
(41:01):
Because we're trying to get him to go away. And
then he looks up and he's like, is there really
a rat? Is there really a rat? Because I'm from
Brooklyn and I'm not afraid of rats. And I was like, oh,
you're from Brooklyn. So that's how we started talking. And
then so he said, I was like, what are you
(41:22):
here for? And he's like, oh, I'm here for the conference. Like, oh, cool.
Were you here to see? And he's like, I'm not
seeing anybody. I'm speaking. I mean, I'm like, OK, this
guy has. Excuse me. And anyway, we started talking about
he did read it and he started read it. And then,
of course, I hadn't heard of it. But, you know,
now you get to know me. I'm like, I don't
hear of anything.
Speaker 4 (41:41):
Right, right, right. But what's interesting about this, like, Jace,
I've been in a lot of calls and Zooms with
Serena and a lot of calls with Alexis. And by
the way, they're both so different, but they complement each
other so well. And they'll never mention they're each other's partners.
They keep it so professional in their lane. But then
when they come together, they're really magical.
Speaker 3 (41:59):
They keep it very church and state. Yeah. Yeah.
Speaker 1 (42:01):
So what have you learned from him as an investor?
Speaker 3 (42:04):
We keep it very church and state. But I do
go to him for advice. I'm like, OK, so what
do you think about this? And how do you build
these deals? I always pick his brain when it comes
on building a team. I think he builds incredible teams
and also always pick his brain on when it comes
to early stage investments in terms of sectors. Like what's
(42:24):
going to be another sector that's going to be exciting,
whether it's AI or he's probably already invested in companies
way before that sector is even popular, which is honestly incredible.
Speaker 2 (42:33):
I will say one of my favorite stories, because, you know,
we followed sports very closely, was your influence on the
Angel City investment, which as at least as it's been
told or as he's told it.
Speaker 1 (42:45):
Olympia was, you know, getting into playing soccer.
Speaker 3 (42:48):
So this is a false story. Yeah. But let's correct. Yes.
Let's correct it.
Speaker 1 (42:52):
OK.
Speaker 4 (42:53):
OK.
Speaker 3 (42:53):
I'm not a pro. So I'm like pro tennis. So
the fact that Olympia was playing soccer, I was already
salty about. I think he kind of did that deal
to make me mad because I'm like, let's do something
in tennis because obviously let's amplify tennis.
Speaker 4 (43:09):
Right.
Speaker 3 (43:09):
But that's that's the real story.
Speaker 2 (43:10):
But the part of the story that I love is
that and you tell us whether this is true or not.
is that the baseline should be you need to do
something for equal pay in sports.
Speaker 1 (43:20):
Is that right?
Speaker 3 (43:21):
You remember earlier I said that I don't want Olympia
to do what I had to fight for for equal
pay because I already did that through tennis. And for
years I missed out on equal pay because I'm fighting
for equal pay. And I think it's I think what
they're doing in soccer is amazing. But I think it's
disgusting that they get paid so little money. It's just
(43:41):
it's not even a conversation to me. It's not even close.
I actually watch soccer and I love women's soccer. I
watch women's soccer. And the fact that so many people
watch women's soccer and then they're getting paid, it's like
what they're getting paid is upsetting. So I love that
Alexis did that deal. And I think what he did
was really amazing there. But I was pushing for Tennessee.
Speaker 1 (44:03):
I was like, no, let's just go for tennis.
Speaker 3 (44:05):
But I did win because Olympia does not like soccer anymore.
Speaker 4 (44:08):
Oh, is that right?
Speaker 3 (44:09):
Well, for now, she changed her mind a lot. She
does like tennis a little bit more now. So I'm like, yes. Yeah.
Speaker 1 (44:14):
Listen, I think you can have some good influence there.
Speaker 4 (44:16):
So Serena, you're a few years into retirement. How do
you measure winning today?
Speaker 3 (44:22):
So for me, winning today is getting a deal. Right
now we have a deal on our table and we're
trying to win it. And there's a lot of other VC,
big VC companies that want to be in it. And
so that's a win for me. It's like, how do
I figure out a way to win this deal? And
so that's what we're working on. And I'm super excited.
I feel like we're getting close and I've heard rumors
that we might get it. So I'm like, yes, we
(44:44):
got to win today.
Speaker 4 (44:45):
So Jay, so many times I get calls from founders
And they're saying, Serena Ventures is in. And I call
Serena's like, we're not quite in yet.
Speaker 1 (44:52):
I'm guessing people like to wave that around.
Speaker 3 (44:55):
Exactly.
Speaker 4 (44:56):
We usually have millions of people wanting to be like you.
But in this case, I'll say billions of young people
that want to be like you. If someone is watching
or listening and they want to be the next Serena Williams,
what advice would you give them?
Speaker 3 (45:09):
Oh, easy. It goes back to the very simple advice
of work hard. Nothing... And, you know, nothing takes place
of hard work. Like I was telling the story about
me in Rome and how like going to breakfast was
a thing because that's how hard I worked. It doesn't
come easy. And I work for everything, whether it was
winning championships or whether it's being an investor. I went
(45:30):
to San Francisco and I worked hard there. I had
to fight my way to even get there. figure out
a way to get idea of what these investments are like.
So it's really just about hard work. It's no way
around it. You can't go around. You can't go, you
have to go right through it. And then everything will
fall into place. Love that.
Speaker 1 (45:49):
This has been great. We could talk to you all
day and have fun and have fun. Are you, are
you having fun?
Speaker 3 (45:55):
I am.
Speaker 2 (45:55):
Yeah.
Speaker 5 (45:56):
Yeah.
Speaker 3 (45:56):
I think, I think it's important to have fun, but
I think it's important also to take a moment and
just look up at the sky and give grace or
look at a tree and say, I'm here. I'm alive today.
And I've been doing that lately. And that has made
me just appreciate just being around. And that makes my
day even better. So it's something new. I'm trying. Sorry.
(46:17):
I'm just trying to tell you guys.
Speaker 4 (46:19):
Gratitude is very powerful.
Speaker 3 (46:20):
It is.
Speaker 4 (46:21):
Thank you. This has been awesome.
Speaker 3 (46:22):
Awesome. Thank you. Thanks for having me.
Speaker 5 (46:33):
The Deal is a production from Bloomberg Podcasts and Bloomberg Originals.
The Deal is hosted by Alex Rodriguez and Jason Kelly.
Our producers are Victor Riveas and Lizzie Phillip. Our story
editor is Siddhartha Mahanta. Our assistant producer is Stacey Wong.
Blake Maples is our sound engineer. Rubab Shakir is our
(46:54):
creative director. Art direction is from Jacqueline Kessler. Original music
by Blake Maples. Casting by Dave Warren. Our managing editor
is David Ravella. Our executive producers are Sage Bauman, Jason Kelly,
Adam Kamisky, Brendan Newnham, Kelly LaFerriere, Ashley Honig, Trey Shallowhorn,
(47:16):
Kyle Kramer, and Andrew Barden. Additional support from Rachel Scaramuzino,
Elena Sosangelis, Vanessa Perdomo, and Anna Masarakis. David Dominguez is
our director of photography. Our camera operators are Sage Passetti
and Angela Reyes-Lata. Our gaffer is Pfeiffer Higgins and our
grip is Courtney Poyser. Katia Vinoy is our video editor.
(47:41):
You can also watch The Deal on Bloomberg Originals, YouTube,
and Bloomberg Television.
Speaker 4 (47:46):
Thanks for listening.
Bloomberg Audio Studios. Podcasts. Radio. News. Welcome back to The Deal.
I'm Jason Kelly.
Speaker 2 (00:14):
And today, a very special episode, a rerun of our
2024 conversation with none other than.
Speaker 1 (00:20):
Serena Williams, the GOAT.
Speaker 2 (00:22):
It's a fascinating time to re-listen to this because she's
back in the world of tennis as a player. She's
playing doubles this week with her sister Venus back at
Arthur Ashe Stadium, back at the Billie Jean King Tennis
Center here in New York City.
Speaker 1 (00:39):
It's the most wonderful time of the year.
Speaker 2 (00:41):
And Serena's getting back to tennis in sort of an
unexpected way. In the intervening years, she's only built her
business portfolio more and more I actually got a chance
to catch up with her again earlier this year at
the Milken Conference out in Los Angeles, and her ambition
remains massive when it comes to business. As I thought
(01:02):
back on this conversation that Alex and I had a
couple years ago, it was fascinating to hear Serena talk
about the early business decisions she made, many of them
that her father, Richard Williams, he really put a lot
of responsibility on her shoulders at a very young age.
She tells a great story, which you'll hear in this
(01:22):
episode about her earliest endorsement deal with Puma literally being
at the table and the conversations that ensued there. And
she's only taken it higher and higher from there. So
a great time now that Serena is back in our
lives in a tennis sense to relisten to this conversation.
Speaker 1 (01:39):
On the deal. All right. So please introduce yourself.
Speaker 3 (01:54):
All right. Well, that's I never really get asked that.
I mean, you asked me to come here. So, you know,
I'm Serena. I like to go by Serena. And what
else am I going to say that's really putting me
on the spot?
Speaker 1 (02:09):
How do you how do you describe yourself these days?
Speaker 3 (02:11):
How do I describe myself? I describe myself first as
a mom. I'm a mom. I'm a businesswoman and I'm
a free spirit. We'll go with that.
Speaker 1 (02:20):
You know, this this notion of.
Speaker 2 (02:22):
Reflecting on what you did as an athlete, as you
look back, you know, half a billion dollars in earnings
over the course of your career, how does that feel
as you embark even further on your business career, that
sort of financial success in sports?
Speaker 1 (02:39):
Yeah.
Speaker 3 (02:39):
You know, when I started tennis, first of all, I'm
from Compton, California, and I remember playing on these courts
and you know, my life was great. I never felt
like I needed anything, you know? And so for me,
money was never a motivation. I remember when I first
started back in the day, they used to write out
checks after you won your tournament and I would always
(03:01):
forget to get the checks. So at the end of
the year, they would always have to say, Serena, we
have all these checks for you. I'm like, oh my God.
Speaker 1 (03:07):
So it was never- You would literally forget to pick
up the check?
Speaker 3 (03:09):
Literally. And at the time I had an accountant who
would be like, Serena, like, they've sent me all these
checks that you would forget to get from the tournaments.
And so... So with that being said, that was never
my motivation, to be honest, for my motivation and looking
at the success that I had financially was never my
starting point. My starting point was always like, I just
(03:30):
want to win championships and I want to have fun
and I want to be a great tennis player. And
quite frankly, I just wanted to win a grand slam.
And I honestly, for me, everything else was a bonus.
And obviously it's great. Like, you know, I really, everything
that I have, believe me, I worked really hard for it.
Nothing really came for free and nothing came easy. Like
I think everything, was super hard working for me. But
(03:51):
it is cool to look back and see the success
that I've had financially, but also multiplying that now and
trying to expand that. And then again, just considering like,
what does that mean for me going forward?
Speaker 4 (04:04):
So Serena, when we were thinking about this show, I
started thinking about people that I like, respect, admire in
the world of sports, in the world of business. And
we had a business call recently and I said, would
you come on our show?
Speaker 1 (04:15):
Yeah.
Speaker 4 (04:16):
But I'm interested to know what motivates you today.
Speaker 3 (04:20):
When you're used to being a champion, you're used to winning.
And so that's something that I'm always motivated by is success.
And what is success? I think success is different for
a lot of people. And I think that's one thing
that I think a lot of people get wrong about.
For me, success right now is having great investments. I
think a lot of people's success is being a mom,
(04:42):
which is super successful for me because that's something that
I've always wanted to do in my life. Or maybe
it's getting an A on your grades or whatever that is.
So I think for me, the motivation is definitely success.
Speaker 4 (04:54):
Both of us played for a couple of decades, right?
Very public. Me more domestically, you more around the world.
But what's interesting is, Jason, you mentioned half a billion dollars.
you know, for me, it was about the same thing,
but 90% of my money came from playing baseball on
the field with you is exact opposite with yours is marketing.
(05:14):
How do you think about the impact that you've made,
not only to all your partners, but how the ripple
effect around the world of the business of Serena?
Speaker 3 (05:22):
Yeah, it's so different, right? I think it's really interesting
how I learned early on that your paycheck from tennis,
maybe that's why I forgot them, should be your smallest earning.
That's what my dad always told me growing up. So
I always thought, okay, well, you know, partnering with the
right people and also deciding who do you really want
(05:43):
to partner with? Because for me, it's also about being
very authentic with those partnerships, not necessarily partnering with a
company that, either doesn't believe in what you're doing or
you don't really use and utilize. So I think throughout
my whole career, I wanted to make sure that those
partnerships are very authentic. They spoke to me and they also,
(06:03):
you know, gave back in some sort of way, shape
or form.
Speaker 1 (06:07):
So fair to say your earliest business advice came from
your dad?
Speaker 3 (06:11):
Most of my business advice came from my dad early on.
He is incredibly, incredibly smart. I think he is way
before his time, everything that he did. I think even
when it came to marketing us as tennis players, tennis
is a very expensive sport and you can't make it
from Compton. But I think it was his marketing that
got us that attention, that garnered those press articles that
(06:33):
had reporters coming out or else we would have a
very difficult time getting out of that in order to
make it. But because of the way he thought about
it and because of the way the social media wasn't
a thing back then. So because of the way he
was getting that attention and it was able to push
us up to the top. Obviously our wins counted as well,
which helped keep us up there in the early ages,
(06:55):
like around the junior stage. But he always was way
ahead of his time when it came to marketing and
advice and business advice. And early on, he was like,
you know what, you're going to manage your own money.
Like literally, my first checks from whether it was Puma,
like I got these huge checks. He's like, you figure
it out. And so we had to figure it out.
(07:15):
I'm literally living at his house in the bedroom next
to Venus.
Speaker 4 (07:20):
How old are you at this point?
Speaker 3 (07:21):
I was 16.
Speaker 4 (07:22):
Wow.
Speaker 3 (07:22):
And he's like, you know, most parents, you know, they
take your money and they take something. But, you know,
he's like, you figure it out. And so I remember
having to figure that out and having to learn how
to manage from a very early age and not get
crazy with it. And so he he empowered us to
do that.
Speaker 2 (07:41):
You've said that wasn't as much about the money. It
was about validation and putting you in a position to
be in control in a way that you weren't before.
Speaker 1 (07:50):
Take us back to that moment. That's a fascinating deal.
Speaker 3 (07:53):
Puma is an incredibly fascinating deal. My dad negotiated everything.
And I have to say, Puma was probably about the
money a little bit for me. It was a lot
of money. I remember I was 16 years old. I
had an opportunity to be with other companies, but they passed.
And so... There was this deal that Reebok wanted to
do with me and Venus combined. And my dad and
(08:15):
my team was like, we're not going to do this.
We're not going to package Serena with Venus because she's
going to be amazing. Thank God that we didn't do that.
So we went to L.A. Arnon Milshan at the time
was one of the biggest shareholders in Puma. We're all
in Hollywood. He also is like New Regency and was
producing all these films. We're in this Hollywood studio, walking
(08:38):
in the hallway, all these famous movies like Pretty Woman
and all these posters are on the wall. And we
sit in this conference room and we negotiate. And it's
like literally midnight. I'm 16. My dad's negotiating. They're going
back and forth. And he wants me there for the
whole time to make sure I know everything.
Speaker 1 (08:55):
What to do in the future. You're literally falling asleep
at the table.
Speaker 3 (08:58):
I pass out. I'm not falling asleep. I pass out
at some point.
Speaker 4 (09:02):
Wow.
Speaker 3 (09:02):
You know, I eventually wake up and they're still at
it and I'm just so upset. But what a learning experience.
I learned so much from that experience. And ever since then,
I'm usually behind the scenes. I don't do the negotiating,
but I actually am behind the scenes. But no one
really knows that it's actually me. It was my agent
or whoever. If they get a deal, they come to
(09:24):
me and they say, what do you want to do?
And I tell them exactly what to do.
Speaker 1 (09:27):
Yeah.
Speaker 3 (09:27):
They obviously deliver the message, but it's super connected. We
have such a great relationship when it comes to negotiating.
They really trust my advice and my vision and where
to go with it. And it all started at such
a young age. But I also learned from that to
ask for equity because I didn't at that time, which
I probably should have. And then I ran into Arnon
a couple of years ago and he's like, yeah, you
(09:48):
should have did equity. I'm like, thanks, Arnon.
Speaker 4 (09:51):
I was 16.
Speaker 3 (09:52):
You know, you should have said it. And he's like,
no way. I'm like, okay. But it was... Also a
really good opportunity to see how you can amplify a
complete brand and what, you know, I was able to
help amplify that brand a lot.
Speaker 1 (10:05):
Because there was a little bit of risk on both sides.
Speaker 3 (10:08):
It was.
Speaker 1 (10:08):
It was.
Speaker 3 (10:09):
I was the younger sister at the time. No one,
you know, understood that You could have siblings that play
sport and they can both be great. And at that point,
it was always just one or the other. And so
Venus was an amazing athlete. And so it was like,
you know, they can't be possibly be another one. So
it was a big chance for Puma. But also I was,
(10:29):
you know, doing really amazing things and winning. And I
won a Grand Slam less than a year later. after signing.
Speaker 1 (10:35):
So not a lot of risk for them, not a lot.
Speaker 3 (10:37):
Of risk for them really. But, uh, and I think
they saw that it was a lot of potential and
they saw it early on.
Speaker 4 (10:44):
I remember, I don't know a lot about tennis, you know, Well, good.
Speaker 3 (10:49):
Because I don't know a lot about baseball. I know that.
I already know that.
Speaker 4 (10:52):
But we already know this. This is more for the audience.
But one of the things, I remember when I was
like 25, 26, I always used to remember you, not
for your great plays, but for your fashion.
Speaker 1 (11:02):
Oh, yes.
Speaker 4 (11:03):
And I just thought, like, I wanted to see what
Serena was wearing that day. Really? Awesome. Yeah, with her
skirt or her dress and what Puma is. And I
just thought that, and then the Anna Wintour connection, what
is it about fashion that, motivates you because you've always
been on point.
Speaker 3 (11:17):
So you know my mom used to sew our outfits
when we were younger and i remember some of our
earliest tournament outfits my mom used to make and so
she would be cutting patterns and at the time they're
called these vogue patterns out And she would put them
together and she would sew our tennis outfits or some
other school outfits or whatever. That's always been a natural
(11:37):
attachment to fashion. And eventually I learned how to sew
and how to make things from old socks. And then
eventually I'll use old clothes when I was literally living
in Compton and just learned how to do the craft. Right.
And that's kind of how it started. And eventually I
went to fashion school, which is a whole story in
its own. I feel like I have a zillion stories, but.
Speaker 1 (11:58):
We're here for them, by the way.
Speaker 3 (12:01):
How much time do we have?
Speaker 1 (12:02):
As much as you want.
Speaker 3 (12:04):
It was going to have to be like a two-part session.
Speaker 4 (12:06):
There you go.
Speaker 3 (12:06):
And so then, yeah, so eventually I went to fashion
school and then One thing I did love when I
first came out with Puma is they gave me like
a lot of opportunities to design some of the stuff
that I was wearing or at least say like, this
is what I want to wear. And I knew that, listen,
I don't look like everyone else out here. I don't
play like everyone else. And I'm different. It's clear that
(12:28):
I'm different. I am a black girl and I'm playing tennis.
And so I need to stand out. I don't want
to wear the same kind of outfits that everyone else
was wearing because And so Puma understood that. And then
that kind of started the craze. And obviously Nike came
on right after and just amplified it times a zillion,
which made it even more cool, like which made me
wear like a jean skirt in New York, which was
(12:51):
kind of one of my favorite outfits. It was insane.
I still can't believe I did that. Yeah. I should
have won that year. But anyway.
Speaker 2 (12:57):
But let's talk about some of those specific fashion choices.
The one that I think so many people remember is
the catsuit.
Speaker 3 (13:04):
The catsuit was legendary. Yeah.
Speaker 2 (13:06):
And so like, take us back to that moment, like
that choice. Like, how does that feel? Like when you
put that on, because you have said, I love this
quote from you. It says, when there was an edge
to how I look, there was an edge to my game.
Speaker 3 (13:19):
Absolutely. So that choice was definitely a Puma designer. And
she was like, we want you to do this catsuit.
And I was like, whoa, this is crazy. This is
so cool. So the U.S. Open came and I put
it on. I was like, I'm not doing this. And
I took it off. I was like, I can't do this.
I can't do this. And so I had a second
outfit in case I didn't want to wear the catsuit,
which if you look at the Open in that year,
(13:40):
I think it was 2002, I actually wore the second
outfit in the second round. But I was like, no,
I can't do that anymore. I need to wear that.
I need to own this cat suit. I need to
own it. So, yeah, it was just a really wild experience.
But anyway, I took it off and I was like,
I can't do this. And I'm like, I need to
focus on my game, not on my outfit as I'm
walking out on the court. And I'm asked a few
(14:01):
girls in the locker room what they think. And they're like, oh,
that's crazy. You can't wear that. You can't wear that.
And I'm like, oh, I know. I know. And for
whatever reason, right before walk off, I just changed really fast.
I threw the catsuit on. I zipped it up and
I just walked out. It was like, oh, my God.
And then it was just it was no looking back
after that, really.
Speaker 1 (14:19):
So did it feel interesting? as important in the moment.
Speaker 4 (14:23):
It didn't.
Speaker 3 (14:23):
Okay.
Speaker 1 (14:24):
You didn't know.
Speaker 3 (14:27):
I always say that's how, that's when I got famous.
It wasn't the six grand slams I won before that.
It was a catsuit.
Speaker 1 (14:34):
Yeah.
Speaker 3 (14:35):
I mean, I was pretty young and, and again, there
was not a lot of stuff around body positivity at
that time for a body. They looked like mine in
sport because every woman at that time was Not every woman,
but a lot of women at that time had a
different type of figure than I did. And so I
was really different. I was basically a lone soldier and
(14:56):
it was just me. And even my sister looked like
the typical athlete that was just amazing and long and lean.
And I was just totally different. Yeah. And so it
was without knowing it was really leaning into that. And,
and again, I didn't know I was just doing it.
And then it was a lot of memes, even before
memes were memes.
Speaker 4 (15:17):
You looked amazing.
Speaker 3 (15:18):
Okay.
Speaker 4 (15:18):
I remember, I mean, at that time it was no Instagram,
but you broke the internet. It was Google everywhere. And
I remember a lot of my teammates and buddies from
back home sending me the picture saying, look how fly
she looks.
Speaker 5 (15:28):
Right.
Speaker 4 (15:28):
But in baseball, Jason, it sounds like it's the same
thing in tennis where you look good. You feel good.
Speaker 3 (15:34):
Absolutely.
Speaker 4 (15:35):
You play good.
Speaker 1 (15:35):
Yeah.
Speaker 4 (15:36):
And I love that because that's exactly how I felt
as a player.
Speaker 3 (15:40):
Absolutely.
Speaker 1 (15:41):
But I think we shouldn't underestimate the cultural power that
that moment had.
Speaker 3 (15:48):
And it crossed so many people that weren't watching tennis.
Speaker 1 (15:52):
Right.
Speaker 3 (15:52):
People outside that were OK, maybe in Compton because we
were from there, but like every neighborhood at that point.
But it just crossed all borders and it made people
from all walks of life want to just kind of
watch tennis. And it was just like being that cultural
person to bring in people that don't normally watch the sport. Again,
(16:13):
I didn't understand at the time, but seeing later on
and even the people that started playing tennis after that
and the people that are currently playing because tennis of
myself and my sister, it all started at these moments.
It's crazy to think about. I've never even voiced this stuff. Like,
oh my God.
Speaker 1 (16:30):
But that, I mean, it changes the business of tennis.
Speaker 3 (16:33):
Absolutely.
Speaker 1 (16:34):
Also changes the business of Serena, right?
Speaker 2 (16:36):
I mean, it elevates you because again, I feel like
we need to keep stating, it's a given what you
were doing on the court, but the impact you were
having off the court just becomes magnified to your point.
What does it feel like as that is starting to
take root?
Speaker 3 (16:54):
It definitely feels different as that starts to take place.
There were more contracts and more deals coming in and
more time. But that's what it is about, right? Again,
I'm thinking I was told when I was really young
that you make your money off the court. Tennis should
be your smallest check in our sport at that time.
And so... I'm thinking, okay, this is, again, this is
(17:16):
what my dad was talking about. Like, how did he know?
And so, and then it was also leaning into these
designs even more after the cat suit. It was even
more about leaning into that and how will I want
to make my impact? I think that's about the time
I started going to fashion school and trying to understand
how did I want to make my impact off the court?
Because it was always about having a plan B, even
(17:37):
though I didn't necessarily need it, but it was just
something etched in my head. My dad- You could fall.
Anything can happen. You could break your ankle. You have
to have something to fall back on. And so all
these moments in the back of my mind are like, OK, well,
this is something that I can kind of do in
the future.
Speaker 2 (17:58):
Coming up, Serena talks about how she got into investing,
how she signed with Nike and how she met and
works with her husband, Alexis Ohanian.
Speaker 4 (18:19):
I remember a story with Phil Knight. And I was
with Nike ever since I was 17 years old. And
we had Ken Griffey Jr. on our team. And at
the time, he was like the Michael Jordan. And I
was telling Uncle Phil, like, I want my own shoe,
like Griffey. And at that time, we had Jordan, we
had Griffey, and that was the gold standard. And I'll
never forget, we went to breakfast on a Saturday morning
(18:42):
in Beverly Hills. And I said, Phil, when am I
going to get my own shoe? And he says, Alex...
If you get to a primary market, at the time
I was in Seattle, I would redo your deal and
I'd rewrite your contract. And I said, well, define a
big market. He said, New York, LA, Chicago. I said, okay.
The day I got where George Steinbrenner called me and
traded me to New York, I got a call from
(19:04):
Phil Knight and he said, game on. And because of
his loyalty, no contract, just a handshake. I've been with
Nike ever since. I've never worn another shoe. But when
I got to New York, I sensed things were different.
the impact, all the opportunities that came. When did you
feel that things were different and that whatever brand you
went with actually had a ripple effect, not only domestically,
(19:26):
but around the world?
Speaker 3 (19:27):
Yeah, I think things got really different. I, I do remember, actually,
now that you mentioned it, I actually forgot about the
Seattle Mariners.
Speaker 4 (19:36):
Yeah, there you go.
Speaker 1 (19:37):
She's a baseball expert. It happened right here.
Speaker 3 (19:40):
But I definitely remember you more in New York and
how that that whole world kind of exploded after that.
But for me, I feel like everything changed after that
catsuit and not because of the catsuit. I think it
was me winning the French Open, Wimbledon and the U.S.
Open in the same year. It has been years and
(20:01):
years and years since anyone had done that. and winning
those three Grand Slams in a row. And I have
to say, at the time, there was so many great
tennis players. There was Lindsay Davenport, there was Martina Hingis,
there was Venus Williams, there was Monica Sellis. And to
dominate at that time with Everyone that was so great
was just unheard of. And so I think winning that U.S.
(20:24):
Open just solidified everything and the outfit. And it was like, well,
this kid is amazing. How do I change that? How
do I say, OK, tennis is great, but how do
I extend that and how do I expand that outside
of tennis? Just understanding that. pop culture and then get
invited to different things. And I would be like, oh, wow,
(20:45):
I'm at the Laureus Awards or I'm here and I'm
actually winning these awards. And, you know, except for the
one in LA, I'm still bitter about it. I'm not
competitive at all.
Speaker 2 (20:56):
The winning and losing thing is definitely not.
Speaker 3 (21:00):
Doesn't play with me at all.
Speaker 1 (21:03):
And so how do you take advantage of that?
Speaker 2 (21:04):
Like, what's the process by which, I mean, you've been
with Jill for a long time, Jill Smollard.
Speaker 1 (21:08):
Are the conversations different? Are your ambitions growing?
Speaker 2 (21:12):
Like how do you activate that moment where you are
blowing up even more?
Speaker 3 (21:17):
Well, Jill has been amazing. I feel like leaning into
having someone, a woman in that position, I think quite frankly,
maybe things would have been different if I had a guy,
like maybe I would have had an extra deal or two,
but it was really about leaning in into having a
woman on my team. Interesting. owning that. We got ours
(21:40):
when the time was due, when the time was ready,
but it was sometimes where we had to fight a
little bit extra. It's really just about really empowering not
only yourself, but people around you and your team as well.
Jill works at WME, amazing agent there. I don't even
like that word actually, but I don't know. I haven't
been able to find a different word for that.
Speaker 4 (21:59):
She's like your partner.
Speaker 3 (22:00):
Exactly. Like a partner.
Speaker 4 (22:02):
And how long have you guys been?
Speaker 3 (22:04):
Oh, since 2000. That's incredible. Yeah. It's been an incredibly
long time, but it really was important to be able
to expand and really start to think about what other,
what other things can you touch? What other things can
you do and how to go about doing that? So
then you have to work from a plan. And then
I would have a list. Like I want to be with,
at the time I wasn't with Gatorade. And I was like,
(22:25):
my lifelong dream was to be with Gatorade because I
remember walking around the corner from my tennis court, not
my tennis court, the community court in Compton. We would
walk to the convenience store and my dad would buy
one Gatorade in a can and we would all have
to share it. And it was like, I've always loved that.
And I've always loved that story. And I've always loved Gatorade. And,
(22:47):
and I would always see the mic. I want to
be like mic commercials. And I was like, I want that.
And so I would always, we would always come together
and say, what are some things that you want to
do in a corporate, if it was corporate, what corporate
companies you want to be with?
Speaker 1 (22:59):
And does that resonate with you?
Speaker 2 (23:00):
I mean, because I'm sitting between these two very deliberate
business people who have caught into this from an early,
I mean, do you remember identifying brands that you wanted
to be with?
Speaker 1 (23:11):
Because it sounds like you had a literal list.
Speaker 4 (23:14):
I mean, for me, Gatorade is another one because I
believe I was, I won the Gatorade player of the
year in high school. And I was like, oh my God,
that's so cool. That's the first big award that I
won nationally. And of course, I want to be like,
my campaign was huge. It still is to this day.
But for me, it was Nike. Nike to me was
the ultimate North Star because Michael Jordan wore it, right?
And we all want to be like those. I looked
(23:36):
up to Michael and Magic and Bird.
Speaker 3 (23:38):
Everyone looked up to Michael. A girl, a guy, whatever.
Speaker 4 (23:42):
Who did you look up to? Who inspired you?
Speaker 3 (23:45):
When it came to branding Michael, Michael Jordan, I think
he really was able to do branding in a different way.
And the aplomb that he has walking around is just
second to none. Tennis wise, I was actually inspired by
Monica Settles. I just liked her. I thought she was
really cool. And I liked how she grunt. I do
(24:08):
have a question.
Speaker 4 (24:08):
Was there a call where Jill called you and she said, hi, Serena,
we got this company and this is what they're willing
to pay you. And you said, what? they're willing to
pay me that much i've had moments like that but
i'm wondering if you ever had a moment like.
Speaker 3 (24:21):
That yes i've definitely had that and i'm like let's
start at yes but let's not seem desperate let's let's
wait at least at least an hour now let's wait
at least a few days to call him back.
Speaker 2 (24:34):
But And so let's talk about Nike for a second,
because obviously Puma does one thing.
Speaker 1 (24:40):
But as you've alluded to, Nike does something altogether.
Speaker 3 (24:44):
Absolutely.
Speaker 1 (24:45):
What was that negotiation?
Speaker 2 (24:46):
Like, what do you remember about sort of getting into
business with them?
Speaker 3 (24:51):
So I just remember I wanted to be with Nike.
I had always wanted to be with Nike from day one,
even before signing with Puma. I was wearing Nike just
because I would buy it. And then I would just,
you know, hopefully like sending some messages like, I'm your girl,
I'm your girl. Like, you know, hello. So that was
always a company that I've wanted to be with. I
(25:13):
think they have an opportunity to market, especially at the time.
It's just like, you know, if you want to be
the best, then you have to wear Nike. That was
seared in my mind. I wanted to be the best.
And I think the best They had the best stuff.
They had the best marketing. They had an opportunity to
put you, as we talked briefly, globally. And because tennis
(25:35):
is not just in the United States. It's Australia. It's England.
It's Italy. It's China. It's literally everywhere on the globe.
And I can think of just a handful of companies
that can reach that far. And so for me, I
wanted to reach that far and I wanted to be
with a company that could amplify that. And I'm not
necessarily amplifying them. I wanted them to amplify me.
Speaker 2 (25:56):
You talked about this moment in tennis that I want
to dwell on for a second, because you're right. There
are a lot of great players, but you very quickly
just overcome all of them. You did something market and
notable for the business of tennis, for viewership, for attendance,
for branding off the court. Was that apparent to you
(26:17):
at the time? Or is it only apparent in retrospect?
Speaker 3 (26:21):
No, it was very apparent because you would see matches.
If I wasn't at a tournament or Venus wasn't at
a tournament, the attendance was just different. And years that
I was injured....
Speaker 4 (26:34):
Oh, God.
Speaker 3 (26:36):
Or years that... Stay professional, Serena. Don't say that. Years
that I was injured or years that, you know... I
didn't play. You could just see the difference of, you know,
people that are, were attending the matches or viewers.
Speaker 2 (26:54):
The U S open is my favorite tennis tournament. It
is the most electric setting. And then it's like the
wattage is turned up when you walk out.
Speaker 1 (27:02):
That's just, again, that's factual. I have to say you
feel that.
Speaker 3 (27:06):
And I took on a lot of that pressure as
the years continued after 10 years, you know, I would
feel that pressure of like, okay, it's, is Serena going
to be in New York? And, you know, it's, it was,
it was like a, not the, not the Serena open,
but it was still like a lot of attention on,
(27:28):
you know, myself. Right. And Venus too, but it was
a lot of attention on me.
Speaker 2 (27:33):
Because the numbers are one thing and the numbers are great,
but what's the Serena effect on Serena? You know, like
that pressure in the, in the sense of, you know,
that if you show up, that's, better for tennis. That's
better for the owner of the tournament.
Speaker 3 (27:48):
I don't think that I try to always remain humble.
And I don't, I didn't go in the tournament thinking
that the US Open is still going on and I'm
not playing sadly, but, and it's still going to be
there with or without me. So I always had that
view and I always knew that. But at the same time,
I also did know that for this amount of time
(28:09):
however that's going to be it's going to be super
amplified and it's not easy but you do walk in
with your chest a little farther out in your head
a little higher because also you are a target you
know everyone right at the end of the day isn't
really happy that you're on the front page of all
these papers right and you know they're just like they
they want that and a part of me is like,
(28:31):
take it because it's a lot, it's a lot of
pressure and it's a lot to hold when you lose
is losing is way bigger news than winning. Like if
I want to match, it's almost last page and yeah.
But if it's, if I lose, it's like front center.
So you don't want that story. And so having a
lot of that pressure is definitely not fun, but it's
also a privilege, you know? And I think it's, I
(28:55):
would definitely prefer that pressure than not being If that
makes sense.
Speaker 4 (28:59):
Yeah.
Speaker 1 (29:00):
Pressure is a privilege. It's right there, right when you
walk out on the court, right?
Speaker 4 (29:03):
It is. Wow. It is.
Speaker 3 (29:03):
New York is your favorite tournament.
Speaker 2 (29:05):
Wow.
Speaker 4 (29:06):
But Jace, I want to segue to business because I
was on a call with Serena early on and I
was like, wow, I wasn't expecting that. And not because...
I had a judgment.
Speaker 3 (29:18):
Hey, wait a minute. No, I'll tell you why.
Speaker 4 (29:19):
I'll tell you why. Because the questions you were asking
were so thorough. You had done your due diligence. You
were asking things about, it has to fit with my brand.
And I knew you would know all the numbers, but
I didn't know how authentic you were going to be
and how sincerely, deeply in the weeds you would be.
Speaker 3 (29:37):
Too deep in the weeds we decided, right? Too much.
Speaker 4 (29:42):
But where does that come from? Is it from your
playing days? Attention to detail?
Speaker 3 (29:48):
I feel like, yeah, I'm super attention to detail. I
feel like I've always excelled at education and I love learning.
And so Yeah. So for me, when it comes to
my business, and like I said, I think we decided
I was too much in the weeds. And like literally
what he's talking about, like being on calls with founders
(30:09):
and actually helping founders understand like why their business isn't
working and why it's not successful. Or, you know, like
literally on every call, if we have calls every six weeks,
I own that company. So yeah. not own the company,
but I'm the representative for the company for my firm
as SV CERN Ventures. And so I'm like literally on
the calls. I'm literally helping them understand how their fundraise,
(30:29):
I'm looking at their decks. And so it's a lot.
So I decided, okay, that's too much. I can't go
on like this, but I truly love investing. And that's
one thing that I kind of fell in love with
from tennis. I would see these sponsors because tennis is
all sponsor based. And I would see like some of
these sponsors come up, but I'm like, well, I have
(30:51):
some little cash. Like, how did I not invest in Facebook?
How did I invest in Airbnb? Or how did I
miss Google? Or like, you know, all these companies. I
don't know if you've ever thought of that, but I'm like.
Speaker 4 (31:01):
I missed a bunch.
Speaker 3 (31:02):
How? Like, why? And I started to ask these questions. Like,
why am I out here breaking my neck? and sweating
when I could have invested in these companies and I
could still be doing the same thing, but I wouldn't
have to be such dire. I've got to win the
US Open this year. I've got to pay these bills.
(31:22):
So I literally would be on the court looking at
these sponsors thinking, how did I miss this? And so
I started asking questions and I went to, at the time,
San Francisco, Silicon area. Back then it was a super
boys club.
Speaker 5 (31:35):
Yeah.
Speaker 3 (31:36):
And I would ask questions. I remember even just sitting
in Pinterest at the time one day and just learning
from the founder there and just being a sponge and
just trying to understand the business, understand investing, understand all
this stuff a little bit more. And that's kind of
how it all started.
Speaker 2 (31:54):
Unfortunately, to your point about the Bay Area and underrepresentation,
still there. 2% of VC funding goes to women, even
fewer when you start to go to other categories of underrepresentation.
Was that part of the DNA of Serena Ventress from
the beginning?
Speaker 1 (32:13):
How did that all?
Speaker 3 (32:15):
Another story, if you guys want to hear it. We're
literally here for your story. So I started investing and
then I somehow got into early stage investing. I didn't
realize that. It was called early stage. I just liked
companies that were starting and then I liked growing them.
One of them was Masterclass. I remember meeting the guys.
(32:37):
David is one of the founders and it was a
room about this size, but this is all they had
and they didn't have anything else. And this is where
Masterclass was. And I fell in love with the concept.
I fell in love with what they were doing. And
I was like, I want to be a part of this.
And so it was just finding several different companies like that.
Then Masterclass obviously became Masterclass. And one day I was
(32:58):
at a conference at JP Morgan and Jamie Dimon was
on stage and he was talking to this woman named
Karen Seidman Becker. But she's on stage and she's talking
about women and VC and how women get less than 2%
of all VC money. And I'm thinking- She misspoke. That's
so embarrassing. Like, I'm embarrassed for her.
Speaker 1 (33:19):
Right, right, right, right.
Speaker 3 (33:20):
But that's how people should think about it. But this
is genuine. My genuine thoughts is that she misspoke. So
me being me, after she was done, I go up
to her and I'm like, hi, yeah, I'm Serena. And
then I'm like, well, you've said something on stage. And
I don't know if you meant to say this or
if you said the number wrong, but... something about 2%,
less than 2%. And she was like, you know, Karen.
(33:42):
So she's like the woman I dream of being. And
she's just like, tells me everything. And she just, Gives
me all this amazing information in the span of 10 minutes.
And I'm like, I didn't know. And so that's how
Serene Adventures happened. From that moment forward, I was like,
I need to start an investment company and I'm not
(34:02):
going to be able to change it. But the platform
can help other people talk about it and change it.
And so that's when from that point. three years before
I actually raised a fund. So I worked on doing
more deals. I ended up getting about 16 unicorns in
my portfolio. So that way I would have a good
track record because I knew it wouldn't be probably easy
for us to raise a fund first go around. Yeah.
(34:24):
Until you get to know me and you get to
know the story and you get to know all the
investments that I had done. And that's what happened.
Speaker 4 (34:42):
So Serena, as I hear you speaking, I can't help
but think about like when I transitioned from baseball to
business and it's quite daunting. And I know for me,
there was some imposter syndrome, but we're both former athletes.
I'm a man of color. You're a woman of color.
As you enter the world of capital raising, which is
very difficult, especially when you haven't had the track record
(35:03):
early on. How did that make you feel when you
went to LPs, potential LPs, to raise capital?
Speaker 3 (35:09):
It's a competition. I loved it. It's what I... It
gave me energy. It gives me life in telling my story.
And also, this isn't about me and it's not about
me raising capital. We are investing in women. We are
investing in people of color like that. Two percent is women,
people of color, women of color is less than a fraction. Right.
(35:31):
Like if I want to start a business and my
name isn't Serena Williams, I'm going to have to take
something out on my house. I'm going to have to
go to the bank like it's not I'm not going
to be I'm just going to not be able to
get VC money. But we're changing that. And we don't
only invest in women. We don't only invest in people
of color. But we're putting that on a platform. Our
portfolio right now as it stands is 68% women or
(35:51):
person of color. And that is unheard of in the
VC world. And so for me, it's all about diversity
and bringing everyone together. We invest in literally everyone. We
don't care what you look like. But we hear your
story if you're a woman. We hear your story if
you're a person of color. And a lot of people
that look like me don't even get their story heard.
And so when you do go to these LPs and
you genuinely tell them the story, if they pass, they pass.
(36:15):
But at least you get them thinking. You get them hearing.
And maybe they'll invest in another fund that is doing
the same thing. Maybe that has been around a little
bit longer with a track record a little bit longer.
But they'll come around to us at some point. And
that's kind of how I feel. But I love talking
to LPs and just getting that story told on a
platform that a lot of people don't have. And so
that is, it's super amazing for us.
Speaker 2 (36:36):
The barriers you and your sister and your dad broke
down when it came to tennis, does it feel like
there's a parallel to what you're trying to do in business?
Speaker 3 (36:45):
It does. And I don't want it to be. You know,
my daughter wants to do a sport and I'm like,
you have to do a sport that's, you're not breaking
down barriers because mom has already done that. And You
don't need to do that. And so somehow I find
myself in a similar story without trying. I think eventually
you're just drawn to, you know, whatever you're drawn to.
(37:10):
And without me realizing it, I was always drawn to
this space and it put me here and I'm not
going to change. I am taking a step back. I'm
taking your advice like, oh, my goodness, already done. But
the impact will always be there and the impact will
continue to be there. And I look forward to that.
Speaker 2 (37:28):
Your dad was a partner. Your sister was a partner
and now Alexis is clearly a life partner, but also
I'm fascinated. And I think Alex is too about, you know,
these two entities, these two business entities sort of coming together.
And I wonder, because it's apparent to us as we
look at it, the influence you've had on each other
(37:50):
in terms of investments, what do you think your influence
has been on him?
Speaker 3 (37:55):
Well, I think my influence on him is just, he,
really wants that success. He really wants to be seen
as that best investor. And he is, he's such a
great investor. And I'm like, you already have that, but
he wants it to be even more amplified. And also
(38:17):
just explaining to him and just giving him my insights
of you know, how to play the game. Because you
have to be able to play the game, whether you're
investing or whether you are in sport. It's who plays
the game the best. And some of the greatest businessmen
and investors play the game better than someone who actually
might be better and smarter. And with him, we met
(38:40):
because we were talking about investments all these years ago.
Speaker 1 (38:42):
That's how you met?
Speaker 3 (38:43):
That's how we met. Yeah.
Speaker 1 (38:45):
Oh, you got to tell us that story.
Speaker 3 (38:47):
Okay. You asked. I told you I have a lot
of stories. So I was in Italy at a tournament
and I'd been in Europe for a few weeks at
that point. And then when you hear an American accent,
when you haven't heard it for a few weeks, it's
like refreshing. And so all week at this particular hotel
we were staying at, There is these American people that
(39:08):
were here for a tech conference. And so anyway, so
fast forward to a couple of days later, I have
a match that day. I'm so focused when I play
a match. Like I literally would never leave the room.
I would watch film all day and I would be
in my room and it was a night match. And
night matches are extremely stressful for me mentally because I'm
having to be in the room from like until 6 p.m.
or 5 p.m. So I'm like, I don't want to
(39:31):
be in the room till 5 p.m. today for my chance.
I was like, I just can't do this today. I
just can't. So I left. to go downstairs at breakfast.
Now this is crazy. Like, come on. I mean, I
literally would even eat breakfast in my room. I would
never be seen. I was a ghost. So I went
to have breakfast.
Speaker 5 (39:46):
Woo.
Speaker 4 (39:47):
Wow.
Speaker 3 (39:48):
That's such a big thing. What it was in my world.
So I went downstairs and that was late for breakfast.
I didn't go downstairs to 11 cause I was just
fighting with myself. If I was like, I should be,
I should be studying. That's how hard I was on myself.
So I went down late, breakfast was closed and they
sent me to a different restaurant across the way, which
had like a pool and, And so I went to
this other restaurant with this massive pool. There's all these
(40:10):
chairs and there's all these tables and there's this pool
and there's another side of the pool, there's chairs. And
so we're the only people. It's me, Jill, and my
assistant at the time. And he was Australian. That's going
to come back too. So we sit down, the only
people there, and we order our breakfast and we're just
talking and laughing. This guy walks in with a computer
and he sits down right next to us at the
(40:31):
table right next to us. And I'm like, so upset.
I'm like, do you see how big this area is?
Speaker 1 (40:39):
Are you kidding me?
Speaker 3 (40:41):
Like, do I look, does it look like we want
people next to us? Like it's huge. And I'm like,
oh my goodness. So my assistant at the time, his
name was Zane. He's like, hello, mate. There's a awful accent.
Ozzy accent is the worst. There's a rat over there.
And He's saying that there's a rat. There's a rat.
(41:01):
Because we're trying to get him to go away. And
then he looks up and he's like, is there really
a rat? Is there really a rat? Because I'm from
Brooklyn and I'm not afraid of rats. And I was like, oh,
you're from Brooklyn. So that's how we started talking. And
then so he said, I was like, what are you
(41:22):
here for? And he's like, oh, I'm here for the conference. Like, oh, cool.
Were you here to see? And he's like, I'm not
seeing anybody. I'm speaking. I mean, I'm like, OK, this
guy has. Excuse me. And anyway, we started talking about
he did read it and he started read it. And then,
of course, I hadn't heard of it. But, you know,
now you get to know me. I'm like, I don't
hear of anything.
Speaker 4 (41:41):
Right, right, right. But what's interesting about this, like, Jace,
I've been in a lot of calls and Zooms with
Serena and a lot of calls with Alexis. And by
the way, they're both so different, but they complement each
other so well. And they'll never mention they're each other's partners.
They keep it so professional in their lane. But then
when they come together, they're really magical.
Speaker 3 (41:59):
They keep it very church and state. Yeah. Yeah.
Speaker 1 (42:01):
So what have you learned from him as an investor?
Speaker 3 (42:04):
We keep it very church and state. But I do
go to him for advice. I'm like, OK, so what
do you think about this? And how do you build
these deals? I always pick his brain when it comes
on building a team. I think he builds incredible teams
and also always pick his brain on when it comes
to early stage investments in terms of sectors. Like what's
(42:24):
going to be another sector that's going to be exciting,
whether it's AI or he's probably already invested in companies
way before that sector is even popular, which is honestly incredible.
Speaker 2 (42:33):
I will say one of my favorite stories, because, you know,
we followed sports very closely, was your influence on the
Angel City investment, which as at least as it's been
told or as he's told it.
Speaker 1 (42:45):
Olympia was, you know, getting into playing soccer.
Speaker 3 (42:48):
So this is a false story. Yeah. But let's correct. Yes.
Let's correct it.
Speaker 1 (42:52):
OK.
Speaker 4 (42:53):
OK.
Speaker 3 (42:53):
I'm not a pro. So I'm like pro tennis. So
the fact that Olympia was playing soccer, I was already
salty about. I think he kind of did that deal
to make me mad because I'm like, let's do something
in tennis because obviously let's amplify tennis.
Speaker 4 (43:09):
Right.
Speaker 3 (43:09):
But that's that's the real story.
Speaker 2 (43:10):
But the part of the story that I love is
that and you tell us whether this is true or not.
is that the baseline should be you need to do
something for equal pay in sports.
Speaker 1 (43:20):
Is that right?
Speaker 3 (43:21):
You remember earlier I said that I don't want Olympia
to do what I had to fight for for equal
pay because I already did that through tennis. And for
years I missed out on equal pay because I'm fighting
for equal pay. And I think it's I think what
they're doing in soccer is amazing. But I think it's
disgusting that they get paid so little money. It's just
(43:41):
it's not even a conversation to me. It's not even close.
I actually watch soccer and I love women's soccer. I
watch women's soccer. And the fact that so many people
watch women's soccer and then they're getting paid, it's like
what they're getting paid is upsetting. So I love that
Alexis did that deal. And I think what he did
was really amazing there. But I was pushing for Tennessee.
Speaker 1 (44:03):
I was like, no, let's just go for tennis.
Speaker 3 (44:05):
But I did win because Olympia does not like soccer anymore.
Speaker 4 (44:08):
Oh, is that right?
Speaker 3 (44:09):
Well, for now, she changed her mind a lot. She
does like tennis a little bit more now. So I'm like, yes. Yeah.
Speaker 1 (44:14):
Listen, I think you can have some good influence there.
Speaker 4 (44:16):
So Serena, you're a few years into retirement. How do
you measure winning today?
Speaker 3 (44:22):
So for me, winning today is getting a deal. Right
now we have a deal on our table and we're
trying to win it. And there's a lot of other VC,
big VC companies that want to be in it. And
so that's a win for me. It's like, how do
I figure out a way to win this deal? And
so that's what we're working on. And I'm super excited.
I feel like we're getting close and I've heard rumors
that we might get it. So I'm like, yes, we
(44:44):
got to win today.
Speaker 4 (44:45):
So Jay, so many times I get calls from founders
And they're saying, Serena Ventures is in. And I call
Serena's like, we're not quite in yet.
Speaker 1 (44:52):
I'm guessing people like to wave that around.
Speaker 3 (44:55):
Exactly.
Speaker 4 (44:56):
We usually have millions of people wanting to be like you.
But in this case, I'll say billions of young people
that want to be like you. If someone is watching
or listening and they want to be the next Serena Williams,
what advice would you give them?
Speaker 3 (45:09):
Oh, easy. It goes back to the very simple advice
of work hard. Nothing... And, you know, nothing takes place
of hard work. Like I was telling the story about
me in Rome and how like going to breakfast was
a thing because that's how hard I worked. It doesn't
come easy. And I work for everything, whether it was
winning championships or whether it's being an investor. I went
(45:30):
to San Francisco and I worked hard there. I had
to fight my way to even get there. figure out
a way to get idea of what these investments are like.
So it's really just about hard work. It's no way
around it. You can't go around. You can't go, you
have to go right through it. And then everything will
fall into place. Love that.
Speaker 1 (45:49):
This has been great. We could talk to you all
day and have fun and have fun. Are you, are
you having fun?
Speaker 3 (45:55):
I am.
Speaker 2 (45:55):
Yeah.
Speaker 5 (45:56):
Yeah.
Speaker 3 (45:56):
I think, I think it's important to have fun, but
I think it's important also to take a moment and
just look up at the sky and give grace or
look at a tree and say, I'm here. I'm alive today.
And I've been doing that lately. And that has made
me just appreciate just being around. And that makes my
day even better. So it's something new. I'm trying. Sorry.
(46:17):
I'm just trying to tell you guys.
Speaker 4 (46:19):
Gratitude is very powerful.
Speaker 3 (46:20):
It is.
Speaker 4 (46:21):
Thank you. This has been awesome.
Speaker 3 (46:22):
Awesome. Thank you. Thanks for having me.
Speaker 5 (46:33):
The Deal is a production from Bloomberg Podcasts and Bloomberg Originals.
The Deal is hosted by Alex Rodriguez and Jason Kelly.
Our producers are Victor Riveas and Lizzie Phillip. Our story
editor is Siddhartha Mahanta. Our assistant producer is Stacey Wong.
Blake Maples is our sound engineer. Rubab Shakir is our
(46:54):
creative director. Art direction is from Jacqueline Kessler. Original music
by Blake Maples. Casting by Dave Warren. Our managing editor
is David Ravella. Our executive producers are Sage Bauman, Jason Kelly,
Adam Kamisky, Brendan Newnham, Kelly LaFerriere, Ashley Honig, Trey Shallowhorn,
(47:16):
Kyle Kramer, and Andrew Barden. Additional support from Rachel Scaramuzino,
Elena Sosangelis, Vanessa Perdomo, and Anna Masarakis. David Dominguez is
our director of photography. Our camera operators are Sage Passetti
and Angela Reyes-Lata. Our gaffer is Pfeiffer Higgins and our
grip is Courtney Poyser. Katia Vinoy is our video editor.
(47:41):
You can also watch The Deal on Bloomberg Originals, YouTube,
and Bloomberg Television.
Speaker 4 (47:46):
Thanks for listening.
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Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.
The Clay Travis and Buck Sexton Show
The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.