May 2, 2024 • 49 mins
Serena Williams revolutionized tennis—that much is unquestioned. With her sister and fellow superstar Venus beside her and father Richard behind them both, Williams went on to transform the way the world looks at tennis stars. Having now put her racket down, she has moved on to the world of finance and started her own venture capital firm, Serena Ventures. But this time, she’s doing it all on her own. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, Williams explains just how these early financial lessons formed the basis of success in her second act.
In tennis, Williams is widely regarded as the greatest of all time. In business, she exudes similar ambition for her growing business empire. Williams says she’s built a team that she trusts while staying intimately involved with every major decision. Diving into the details is something she’s known for—Williams was literally at the table for her first big shoe endorsement deal, with Puma.
Serena Ventures has invested in more than 20 companies in its first fund, and that’s in addition to the dozens of angel investments Williams has made. She’s also focused much of the firm’s energy on investing in companies run by traditionally underrepresented founders, especially women and people of color. (Only 2% of venture capital goes to companies led solely by women, while just 1% goes to firms with Black founders.)
You can also watch The Deal on Bloomberg Originals, YouTube or Bloomberg TV.
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Episode Transcript
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Speaker 1 (00:03):
Bloomberg Audio Studios, podcasts, radio news.
Speaker 2 (00:14):
It's a competition. I loved it.
Speaker 3 (00:16):
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. Like if I want to start
a business and my name isn't Serena Williams, I'm gonna
(00:37):
have to take something out of my house.
Speaker 2 (00:39):
I'm gonna have to go to the bank, like I'm
just gonna not be able to get VC money. But
we're changing that.
Speaker 4 (00:48):
All right, Alex Serena Williams the goat. I mean, it
doesn't get any better than her when it comes to
a professional athlete but also a fascinating business person. You
guys know each other like you've got to know each other,
especially as retired athletes, right, I.
Speaker 5 (01:06):
Mean, we know each other very well, and the irony
is very little to do with baseball or tennis. I
know Serena as an investor. She's been investing since twenty thirteen,
and she's passionate and she's good and she's as discipline
and she has big, big plans which you'll hear about.
Speaker 2 (01:22):
Yeah.
Speaker 4 (01:22):
I mean what I took away from this, probably more
than anything, was how early on she was identifying business
and even this notion her father essentially saying the majority
of your money you're going to.
Speaker 2 (01:35):
Make off the court.
Speaker 4 (01:37):
She has a great bit that I won't spoil about
the checks from the tournaments, but you know this notion
that she identified early on that there were opportunities fashion
certainly being one of them.
Speaker 2 (01:49):
But then how she became an investor is so interesting,
it really is. I know her well and I was
surprised on how much she opened up. Yeah, but there's
no doubt that she has the same discipline and passion
for investing yeah, as she did for being to go
in tennis.
Speaker 4 (02:04):
And let's keep in mind this is a career during
which she earned almost half a billion dollars. One of
her earliest deals is with Puma, and one of the
things that that does for her is it unlocks her
potential when it comes to fashion, because all of a sudden,
she's helping design her own outfits and we know the
cultural impact what she wore had.
Speaker 5 (02:27):
And I felt that in real time, the impact that
she made. I also thought it was really interesting mister Williams,
her father and what impact he had not only a
great inspiration person for her, but a great teacher in
life for both girls well.
Speaker 4 (02:40):
And also the idea that her father, who really set
it all up for them, then essentially said, you manage
your own money, figure it out. And so clearly that
was something that drove her to make a lot of
these key decisions. And then as she's going on in
her career going to Silicon Valley standing investing, and this
(03:03):
is something you guys get into and swap notes on
understanding brands. Bloom is one thing, Nike is a whole
different thing. You both have a relationship with that company.
And so her awareness of the power of brands and
the power of her own brand.
Speaker 5 (03:18):
This is truly a business story. I mean, the father
is like a great founder. Yes, he was a great visionary,
he was a great marketer.
Speaker 2 (03:25):
It was brilliant.
Speaker 5 (03:33):
On this episode of the Deal, Serena Williams, all right,
so please introduce yourself.
Speaker 3 (03:48):
All right, Well that's I never really get asked that,
but I mean you asked me to come here, so
I know I'm Serena.
Speaker 2 (03:56):
I like to go by Serena and what else?
Speaker 3 (04:00):
So am I gonna say? That's really putting me on
the spot.
Speaker 2 (04:02):
How do you how do you describe yourself these days?
Speaker 3 (04:04):
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.
Speaker 2 (04:12):
We'll go with that. You know, this notion of 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 3 (04:32):
Yeah, 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
(04:53):
after you won your tournament, and I would always forget
to get the checks.
Speaker 2 (04:56):
So at the end of the year they.
Speaker 3 (04:57):
Would always have to say, so we have all these
checks for you.
Speaker 2 (04:59):
I'm like, oh my god, So it was you would
literally forget to pick up the checksually, and.
Speaker 3 (05:04):
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 want to win championships and
(05:26):
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.
Speaker 2 (05:33):
And obviously it's great.
Speaker 3 (05:34):
Like you know, I really everything that I have, Believe me,
I worked really hard for nothing really came for free,
and nothing came easy. Like I think everything was super
hard working for me. But 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
(05:56):
me going forward?
Speaker 5 (05:58):
So, Serena, when we were thinking about this show, so
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 2 (06:09):
Yeah, but I'm.
Speaker 6 (06:10):
Interested to know what motivates you today when you're used
to being a champion, used to winning, and so that's
something that I'm always motivated by is success and what
a success.
Speaker 3 (06:23):
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. For me, success right now
is having great investments. I think a lot of people's
success is being a mom or 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
(06:43):
for me, the motivation is definitely success.
Speaker 5 (06:47):
Both of us played for a couple 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 ninety
percent of my money came from playing baseball on the
field with you is ecxact opposite.
Speaker 2 (07:05):
With YOURSS marketing?
Speaker 5 (07:06):
Yeah, 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 2 (07:16):
Yeah, it's so different, right.
Speaker 3 (07:18):
I think it's really interesting how I learned early on
that your paycheck from tennis maybe that's why I forgot them.
It should be your small should be your smallest earning.
Oh that's 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
to partner with, because for me, it's also about being
(07:39):
very authentic with those partnerships, not necessarily partnering with a
company that either doesn't believe in what you're doing.
Speaker 2 (07:47):
Or you don't really use and utilize.
Speaker 3 (07:50):
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 you know, gave back in
some sort.
Speaker 2 (07:59):
Of way, shape or form. So fair to say your
earliest business advice came from your dad. Most of my.
Speaker 3 (08:05):
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 had reporters coming out
(08:28):
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 social media wasn't a thing back then, So
because of the way he was getting that attention, it
was able to push ups, push us up.
Speaker 2 (08:43):
To the top.
Speaker 3 (08:44):
Obviously, our wins counted as well, which helped keep us
up there in the early ages, 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 he my first
checks from whether it was Puma, Like I got these
(09:06):
huge checks. He's like, you figure it out.
Speaker 2 (09:08):
And so we had to figure it out.
Speaker 3 (09:09):
And I'm literally living at his house in the bedroom.
Speaker 2 (09:12):
And next time, how old are you at this? I
was sixteen?
Speaker 3 (09:15):
Wow, And he's like, you know, most parents, you know,
they take your money and oh 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.
Speaker 2 (09:33):
Us to do that. You've said that wasn't as much
about the money.
Speaker 4 (09:37):
It was about validation and putting you in a position
to be in control in a way that you weren't before.
Speaker 2 (09:44):
Take us back to that mode. That's a fascinating deal.
Speaker 3 (09:47):
Puma is an incredibly fascinating deal. My dad negotiate everything,
and I have to say Puma was probably about the
money a little bit forgetting and I was like, it
was a lot of money. I remember I was sixteen
years old. I had an opportunity to be with other
companies but they passed.
Speaker 2 (10:01):
So there was this deal that Reebok.
Speaker 3 (10:04):
Wanted to do with me and Venus combined, and my
dad and 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. Yeah, So we went to la Arnan.
Milshan at the time was one of the biggest shareholders
in Puma. They were all in Hollywood, like he also
(10:25):
is like New Regency and owns all these it was
producing all these films. We're in this Hollywood studio, walking
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 sixteen. My dad's negotiating. They're going
back and forth, and he wants me there for the
(10:46):
whole time to make sure I know.
Speaker 2 (10:49):
What to do in the future. You're literally falling asleep
at the table. I pass out. I'm not following asleep.
I pass out at some point. Wow, you know.
Speaker 3 (10:56):
I eventually wake up and they're still at it, and
I'm just so upset.
Speaker 2 (11:00):
But what a learning experience.
Speaker 3 (11:02):
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
me and they say, what do you want to do?
And I tell them exactly what to do, but they
obviously deliver the message, but it's super connected. We have
(11:25):
such a great relationship when it comes to negotiating. They
really trust my advice and my vision and where to
go with it. And all start at such a young age.
But I also learned from that task for Equity because
I didn't at that time, which I.
Speaker 2 (11:37):
Probably should have.
Speaker 3 (11:39):
And then I ran into our non year a couple
of years ago and he's like, yeah, you should have
did equity. I'm like, thanks, are not you know you
should have said it. It'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 2 (11:59):
Because there was a little bit of risk on both sides.
Speaker 3 (12:01):
It was it was 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, you know, doing really amazing things
(12:24):
at winning and I won a Grand Slam less than
a year later after signing, So not a lot of
risk for them, not a lot of risks really, but
and I think they saw that it was a lot
of potential.
Speaker 2 (12:36):
Yeah, they saw it early on.
Speaker 5 (12:38):
I remember, I don't know a lot about tennis, you know,
but what I do good because I.
Speaker 2 (12:43):
Don't know a lot about baseball.
Speaker 5 (12:44):
I know that, I know that, but we already know this.
This is more for the audience. But one of the
things I remember when I was like twenty five twenty six,
I always used to remember you not for your great plays,
but for your fashion. Oh yeah, And I just thought,
like I wanted to see what Serena was wearing a
yet dresser and what pumas And I just thought that,
and then the winter connection. What is it about fashion
(13:08):
that motivates you? Because you've always been on point?
Speaker 3 (13:11):
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
(13:31):
attachment to fashion. And eventually I learned how to sew
and how to make things from old socks, and then
eventually I would use old clothes when I was literally
living in Compton and just learned how to do the
craft right.
Speaker 2 (13:43):
And that's kind of how it started.
Speaker 3 (13:46):
And eventually I went to fashion school, which is a
whole story in its own.
Speaker 2 (13:49):
I feel like I have a zillion stories.
Speaker 4 (13:52):
We're here for them, but how much times us as
you are, it.
Speaker 3 (13:58):
Was gonna have to be like a two part session.
And so then yeah, so eventually I went to fashion school.
And then one thing I did love and when I
first came out with Pumas, that gave me like a
lot of opportunities to design some of the stuff that
I was wearing, or at least say like this is.
Speaker 2 (14:14):
What I want to wear. And I knew that.
Speaker 3 (14:16):
Listen, I don't look like everyone else out here, I
don't play like everyone else, and I'm different.
Speaker 2 (14:21):
It's clear that I'm different.
Speaker 3 (14:23):
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,
and so Puma understood that, and then that kind of
started the craze. And obviously Nike came on right after
and just amplified at times a zillion, which made it
even more cool. Which made me wear like a jean
skirt in New York, which was kind of one of
(14:45):
my favorite oullis. I was insane. I still can't believe
when I did that.
Speaker 2 (14:48):
Yeah, I should have won that year. But anyway, but.
Speaker 4 (14:51):
Let's talk about some of those specific fashion choices. The
one that I think so many people remember is the catsuit.
Speaker 2 (14:58):
The catsue was legendary, So.
Speaker 4 (15:00):
Like, take us back to that moment, like that choice,
Like what does that feel like when.
Speaker 2 (15:05):
You put that on?
Speaker 4 (15:06):
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 (15:12):
Absolutely, So that choice was definitely a Puma designer and
she was like, we want you to do this cat
suit and I was like, whoa, this is crazy, this
is so cool. So the US 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 cat suit, which if you look at the Open
(15:33):
in that year, I think it was two thousand and two.
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 catsuit.
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 asked
(15:54):
a few girls in the locker room what they think,
and they're like, oh.
Speaker 2 (15:57):
That's crazy. You can't wear that. You can't wear that.
Speaker 3 (15:59):
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 cat suit on, I zipped it up,
and I just walked out.
Speaker 2 (16:08):
It was just like, oh my god. And then it
was just it was no looking back after that.
Speaker 4 (16:12):
Really, So did it feel as no important in the moment?
It didn't know Okay, you didn't know because that changed
me everything.
Speaker 3 (16:20):
I always say, that's how that's when I got famous.
Wasn't the six Grand slams I won before that?
Speaker 2 (16:27):
It was a cat suit? Yeah, I mean I was
pretty young.
Speaker 3 (16:30):
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,
not every woman, but a lot of women at that
time had a different type.
Speaker 2 (16:44):
Of figure than I did. And so I was really different.
Speaker 3 (16:47):
I was basically a lone soldier and 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.
Speaker 2 (16:57):
And so it was.
Speaker 3 (16:59):
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, right right.
Speaker 5 (17:10):
You looked amazing, Okay, I remember, I mean at that
time it was no Instagram, but you broke the internet.
Speaker 2 (17:16):
It was Google everywhere.
Speaker 5 (17:17):
And I remember a lot of my teammates and buddies
from back home sending me the picture saying, look how
fly she looks?
Speaker 2 (17:22):
Right?
Speaker 5 (17:22):
But in baseball, Jason it sounds like it's the same
thing in tennis, where you look good.
Speaker 2 (17:27):
You feel good, absolutely good.
Speaker 5 (17:29):
Yeah, and I love that because that's exactly how I
felt as a player.
Speaker 4 (17:33):
Absolutely, But I think we shouldn't underestimate the cultural power
that that moment had.
Speaker 3 (17:41):
And it crossed so many people that weren't watching tennis, right,
people outside that were okay, maybe incompetent because we were
from there, but like every neighborhood at that point was
watching it. But it just crossed all borders and many
people from all walks of life want and just kind
of watched tennis. And it was just like being that
cultural person to bring in people that don't normally watch
(18:06):
the sport. Again, 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 of myself and my sister, It all start at
these moments. It's crazy to think about I've never even
voiced this stuff, like, oh my god.
Speaker 2 (18:23):
But that, I mean, it changes the business of tennis. Absolutely,
also changes the business of Serena, right, 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, that the impact you were having off the.
Speaker 4 (18:40):
Court just becomes magnified. To your point, what does it
feel like as that is starting to take root.
Speaker 3 (18:48):
It definitely feels different as that starts to take place.
There were more contracts and more deals coming in and
more time.
Speaker 2 (18:56):
But that's what it is about.
Speaker 3 (18:58):
Right Again, I'm thinking I was when I was really young,
that you make your money off the court ten it
should be your smallest check in our sport at that time,
and so I'm thinking, okay, this is again, this is
what my dad was talking about, like how did he
know 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 I want to
(19:20):
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.
Speaker 2 (19:26):
Impact off the court?
Speaker 3 (19:27):
Yeah, because it was always about having a plan B,
even though I didn't necessarily need it, but it was
just something etched in my head my dad. You could fall,
anything could 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, Okay, well,
this is something that I can kind of do in
(19:48):
the future.
Speaker 2 (19:52):
Coming up.
Speaker 4 (19:52):
Serena talks about how she got into investing, how she
signed with Nike, and how she met and works with
her husband, Alexi so Henian.
Speaker 5 (20:12):
I remember a story with Phil Knight. And I was
with Nike ever since I was seventeen years old, and
we had kN Griffith Junior and 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 Griffy. And at that time we had Jordan, we
had Griffy and that was the gold standard.
Speaker 2 (20:32):
And I'll never forget.
Speaker 5 (20:32):
We went to breakfast on a Saturday morning 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 rewrite
your contract. And I said, well, define a big market.
He said, New York, La Chicago. I said, okay. The
(20:53):
day I got where, George Steiermanter called me and traded
me to New York. I got a call from Phil
Knight and he said gay on wow and because of
his loyalty, no contract, just a handshake. I've been with
Nika since. I've never worn another shoe. But when I
got to New York, I sends things were different, the impact,
all the opportunities that came. When did you feel that
(21:15):
things were different and that whatever brand you went with
actually had a riple effect not only domestically but around
the world.
Speaker 3 (21:21):
Yeah, I think things got really different. I do remember,
actually now that you mentioned, I actually forgot about the
Seattle Mariners.
Speaker 2 (21:30):
Yeah, here you go. She's a baseball ye.
Speaker 3 (21:33):
Right, Yeah, 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 cat suit, and not because of the catsuit.
I think it was me winning the French Open, Wimbledon
and the US opened in the same year. It's been
(21:54):
years and 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 sells
and to dominate at that time with everyone that was
so great was just unheard of. And so I think
(22:17):
winning that US Open just solidified everything and the outfit
and it.
Speaker 2 (22:21):
Was like, well, this, this, this, this kid is amazing.
How do I change that?
Speaker 3 (22:26):
How do I say, Okay, 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, I'm at the Larius Awards or I'm here
and I'm actually winning these awards and you know, except
for the one, and I'm still bitter about I'm not
(22:49):
competitive at all, definitely not.
Speaker 2 (22:53):
It doesn't play with me at all. And so how
do you take advantage of that?
Speaker 4 (22:58):
Like what's the process by which means you've been with
Jill for a long time, Jill Smuller, are the conversations different?
Speaker 2 (23:04):
Are your ambitions growing? Like?
Speaker 4 (23:06):
How do you activate that moment where you are blowing
up even more?
Speaker 3 (23:11):
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
(23:33):
got ours 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's works at w ME. 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.
Speaker 2 (23:53):
Really.
Speaker 3 (23:53):
I think your partner exactly like a partner. And how
long have you guys been, Oh, since two thousand, that's
in question. 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,
(24:15):
like I want to be with At the time, I
wasn't with Gatorade, and I was like, my lifelong.
Speaker 2 (24:20):
Dream was to be with Gatorade. Because I remember.
Speaker 3 (24:23):
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.
Speaker 2 (24:40):
And I would always.
Speaker 3 (24:41):
See the mic I want to be like Mike 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 corporate?
Speaker 2 (24:51):
If it was corporate with corporate companies you want to
be with? And does that resonate with you?
Speaker 4 (24:54):
I mean, because I'm sitting between these two very deliberate
business people who have cott into this from an early
I mean, do you remember identifying brands that you wanted.
Speaker 2 (25:04):
To be with? Because it sounds like you had a
literal list.
Speaker 5 (25:07):
I mean, for me, Gatoray 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
want 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' woard right and
(25:27):
we all want to be like those. I looked up
to Michael and Magic and Bird.
Speaker 2 (25:32):
Everyone looked up to Michael, A girl, a guy, whatever.
Who did you look up to? Who inspired you when
it came to branding? Michael Michael Jordan.
Speaker 3 (25:43):
I think he really was able to do branding in
a different way, and the plumb that he has walking
around is just second to none tennis wise. I was
actually inspired by Monica Sellis.
Speaker 2 (25:53):
I just liked her.
Speaker 3 (25:55):
I thought she was really cool and I liked how
she grunts.
Speaker 2 (26:01):
I do have a question.
Speaker 5 (26:02):
Was there a call where Joe called you and she said, I, 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
more than if you had a moment.
Speaker 3 (26:15):
I guess 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 4 (26:30):
And so let's talk about Nike for a second, because
obviously Puma does one thing, as you've alluded to, Nike
does something altogether. Absolutely, what was that negotiation, Like, what
do you remember about sort of getting into business with them?
Speaker 3 (26:45):
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
(27:06):
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 talk briefly globally, and because tennis
(27:29):
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 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 (27:49):
You talked about this moment in tennis that I want
to dwell in.
Speaker 4 (27:52):
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 at the time
(28:12):
or is it only apparent in retrospect.
Speaker 3 (28:15):
No, it was very apparent, Yeah, 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, oh God, or years that stay
professionals arena don't say that years that I was injured,
(28:38):
or years that you know, I didn't play. You could
just see the difference of you know, people that were
attending the matches or viewers.
Speaker 4 (28:47):
The US 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 2 (28:56):
That's just again, that's factual. I have to say.
Speaker 3 (28:59):
You feel that I took on a lot of that
pressure as the years continued. After ten years, you know,
I would feel that pressure of like, okay, it's it's
Serena going to be in New York and right it's
it was. It was like not the not the Serena Open,
but it was still like a lot of attention on
(29:22):
you know, myself, right, and Venus too, But it was
a lot of attention on.
Speaker 4 (29:26):
Me because the numbers are one thing, and the numbers
are great, but what's the Serene effect on Serena? You know,
like that pressure then in the in the sense of
you know that if you show up, that's better for tennis,
that's better for the the owner of the tournament.
Speaker 2 (29:42):
I think that I try to always remain humble.
Speaker 3 (29:45):
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, however,
that's going to be, it's going to be super amp
fire and it's not easy, but you do walk in
(30:07):
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,
and you know, they're just like they want that, And
a part of me is like, take it, because it's
a lot of pressure and it's a lot to hold
(30:28):
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
(30:48):
it's I would definitely prefer that pressure then not, if
that makes sense.
Speaker 2 (30:53):
Yeah, pressure is a privilege. It's right there right when
you walk out of the cot.
Speaker 3 (30:56):
Wow, it is your New York is your favorite turn.
Speaker 2 (30:59):
Wow.
Speaker 5 (31:00):
But Jayson, I want to segue to business because I
wasn't a call with Serena early on, and I was like, wow,
I wasn't expecting that, And not because I had a judgment.
Speaker 2 (31:12):
You know, I'll tell you why. I'll tell you why
because the.
Speaker 5 (31:14):
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. Where too much? But where
(31:37):
does that come from? Is it from your playing days?
Asenially details?
Speaker 3 (31:41):
I feel like, yeah, I'm super tending 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 are you talking about? Like being on calls with
(32:02):
founders 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 not own the company,
but I'm the representative for the company from my firms
as sv CER and Adventures, and so I'm like literally
on the calls. I'm literally helping them understand how their fundraise.
(32:23):
I'm looking at their decks and so it's a lot.
Speaker 2 (32:26):
So I decide, Okay, that's too much. I can't go
on like this.
Speaker 3 (32:30):
But I truly love investing yea, 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 some little cash, Like
how did I not invest in Facebook?
Speaker 2 (32:48):
How I invest in airbnber? How did I miss.
Speaker 3 (32:51):
Google or like you know, all these companies. I don't
know if you ever thought of that, but I'm.
Speaker 2 (32:54):
Like, I missed a bunch, how like why?
Speaker 3 (32:57):
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.
Speaker 2 (33:10):
I've got to win us this year. I've got a
padies bills.
Speaker 3 (33:16):
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 2 (33:29):
Yeah, and I would ask questions.
Speaker 3 (33:31):
I remember even just sitting in Pinterest at the time
one day and just learning from the founder there and
just just just being a sponge and just trying to
understand the business, understand stand investing, understand all this stuff
a little bit more.
Speaker 2 (33:46):
And that's kind of how it all started.
Speaker 4 (33:48):
Unfortunately, to your point about the Bay Area and underrepresentation
still there. Oh is it two percent of VC funding
less goes to women, you know, even fewer when you
when you start to go to other categoryories of underrepresentation?
Was that part of the DNA of Serena Ventures from
the beginning?
Speaker 2 (34:07):
How did that all?
Speaker 3 (34:08):
Another story? If you guys want to hear it.
Speaker 2 (34:10):
So I started, We're literally here for your stories.
Speaker 3 (34:16):
So I started investing, and then I somehow got into
early stage investing.
Speaker 2 (34:20):
I didn't realize that it was called early stage.
Speaker 3 (34:23):
I just liked companies that were starting, and then I
liked growing them. One of them was Masterclass. I remember
meeting the guys. 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 felt loved what they were doing
and I was like, I want to be a pier
(34:44):
of this. And so it was just finding several different
companies like that in Masterclass obviously became Masterclass.
Speaker 2 (34:50):
Ye.
Speaker 3 (34:50):
And one day I was at a conference at JP
Morgan and Jamie Diamond was on stage and he was
talking to this woman named Karen Sideman Becker. But she's
on stage and she's talking about women and VC and
how women get less than two percent of all VC money.
But I'm thinking, she misspoke. That's so embarrassing, Like I'm embarrassed.
Speaker 2 (35:12):
For her, right right, right.
Speaker 3 (35:14):
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 can said the number wrong, but something about
two percent less than two percent, And she was like,
(35:35):
you know, Karen, so she's like the woman I dream
of being, and she's just like she just tells me everything,
and she just gives me all this amazing information the
span of ten minutes, and I'm like, I didn't know.
And so that's how Stain Adventures happened from that moment before,
and I was like, I need to start an investment
(35:55):
company and I'm not 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, ended up getting about sixteen
unicorns and 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.
Speaker 2 (36:16):
Fund first go around.
Speaker 3 (36:17):
Yeah, until you get to know me and you get
to know the story, and you need to know all
the investments that I had done.
Speaker 2 (36:23):
And that's what happened.
Speaker 5 (36:24):
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.
Speaker 2 (36:35):
But we're both former athletes.
Speaker 5 (36:37):
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
early on.
Speaker 2 (36:47):
Yep, how did that make.
Speaker 5 (36:48):
You feel when you went to LP's potential piece to
raise capital.
Speaker 2 (36:52):
It's a competition. I loved it.
Speaker 3 (36:54):
It's what I It gave me energy. It gives me
life in telling me n 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, Like, if
(37:14):
I want to start a business and my name isn't
Serena Williams, I'm gonna have to take something out of
my house.
Speaker 2 (37:19):
I'm gonna have to go to the bank.
Speaker 3 (37:20):
Like it's not I'm not gonna be I'm just gonna
not be able to get VC money.
Speaker 2 (37:24):
But we're changing that.
Speaker 3 (37:26):
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 as
sixty eight percent women are 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
(37:46):
hear your story if you're a personal 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 a story, if
they pass, they pass, but at least you get them
thinking to get them here, and maybe they'll invest in
another fund that is doing the same thing, maybe that
has been around a little bit longer, with the track
record a little bit longer, but they'll come.
Speaker 2 (38:07):
Around to us at some point. And that's kind of
how I feel.
Speaker 3 (38:09):
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 4 (38:19):
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 2 (38:28):
It does, and I don't want it to be.
Speaker 3 (38:32):
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, and without me realizing it, I was always
(38:55):
drawn to this space and it put me here and
I'm not going to change. I am get a step
back up 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 4 (39:10):
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
(39:33):
in terms of investments, What do you think your influence
has been on him?
Speaker 3 (39:38):
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.
Speaker 2 (39:59):
And also just.
Speaker 3 (40:02):
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 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
(40:22):
because we were talking about investments all these years ago.
Speaker 2 (40:25):
That's how you met, That's how we met. Yeah, we
just got to tell us that story.
Speaker 3 (40:29):
Okay, you asked, you know, 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 where you were staying at, there is these American
(40:50):
people that were here for a tech conference. And so anyway,
so fast forward to a couple days later, I have
a match that day, and 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 six
(41:10):
pm or five pm. So I'm like, I don't want
to be in the room till five pm today for
by chance.
Speaker 2 (41:16):
So I was like, I just can't do this today.
I just can't.
Speaker 3 (41:18):
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.
Speaker 2 (41:24):
I would never be seen. I was a ghost.
Speaker 3 (41:26):
So I went to have breakfast. Who wow, 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 eleven because 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
(41:48):
had like a pool, and so I went to this
other restaurant with this massive pool. There's all these chairs
and there's all these tables, and there's this pool and
there's an other side of the pool there's chairs.
Speaker 2 (41:57):
And so we're the only people.
Speaker 3 (41:59):
It's me, Jill and my assistant at the time, and
he was Australian that's going.
Speaker 2 (42:03):
To come back to.
Speaker 3 (42:04):
So we sit down the only people there, and we
order our breakfast and we're just talking and laughing and
this guy walks in with the computer and he sits
down right next to us, at the table, right next
to us, and I'm like so upset. I'm like, do
you see how big this area is? B like, do
I look? Does it look like we want people next
(42:26):
to us?
Speaker 2 (42:27):
Like? It's huge?
Speaker 3 (42:29):
And I'm like, oh my goodness. So my assistant at
the time his name was Zane. He's like, and it
there's a allfl accent. I'll see, access is the worst.
And there's a rat over there, and he's saying that
there's a rat. There's a rat, because we're trying to
get him to go away.
Speaker 2 (42:46):
Oh my god.
Speaker 3 (42:47):
And then he looks up and he's like, is there
really a rat?
Speaker 2 (42:55):
And he's is it really a rat?
Speaker 3 (42:56):
Because I'm from Brooklyn and I'm not afraid of rats.
And I was like, oh, you're for Brooklyn. So that's
how we started talking. And then so he said, I
was like, what are you here for? And he's like, oh,
I'm here for the conference. It's like, oh, cool, who
are you here to see? And he's like, oh, I'm
not seeing anybody. I'm speaking. I mean, I'm like, okay,
this guy has excuse me. And anyway, he started talking
(43:17):
about he did read it, and he started read it
and then of course I hadn't heard of it.
Speaker 2 (43:21):
But you know, now you get to know me. I'm like,
I don't hear of anything.
Speaker 5 (43:24):
It's right, right, right, But what's interesting about this? Like Jace,
I've been in a lot of calls in zooms with
Serena and a lot of calls with Alexis. And by
the way, they're both so different, but they compliment 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.
Speaker 2 (43:41):
They keep it a very church and state.
Speaker 4 (43:42):
Yeah yeah, so what if you've learned from him as
an investor, we keep it very church and state.
Speaker 3 (43:48):
But I do go to him for advice. I'm like, okay,
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 I always pick his brain on
when it comes to early stage investments in terms of sectors,
like what's going to be another sector that's going to
be exciting, whether it's AI or He's probably already invested
(44:11):
in companies way before that sector is even popular, which
is honestly incredible.
Speaker 4 (44:16):
I will say one of my favorite stories, because you
know we followed sports very closely, was your influence on
me angel City investment, which, as at least as it's
been told her as he's told it, Olympia was, you know,
getting into playing soccer.
Speaker 3 (44:31):
So this is a false story. Yeah, but let's correct.
Speaker 2 (44:34):
Yes, let's correct it.
Speaker 3 (44:35):
Okay, Okay, I'm not a pro, so I'm like pro tennis.
So the fact that Olympia was playing soccer, I was
already salty about that. I think he kind of did
that deal to make me mad because I'm like, let's
do something in tennis. Yeah, because obviously let's amplify tennis, right,
But that's that's the real.
Speaker 4 (44:53):
But the part of the story that I love is that,
and you tell us whether this is true or not,
is that the east line should.
Speaker 2 (45:00):
Be you need to do something for equal pay in sports.
Is that right?
Speaker 3 (45:04):
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 it's
(45:24):
not even a conversation to me, it's not even close.
I actually watched soccer, and I love women's soccer. I
watched 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 tennis.
Speaker 2 (45:45):
I was like, no, but I did win.
Speaker 3 (45:49):
Because Olympia does not like soccer anymore.
Speaker 2 (45:51):
Oh is that right?
Speaker 3 (45:52):
Well, for now she changes their mind a lot. She
does like tennis a little bit more now, So I'm like.
Speaker 2 (45:56):
Yes, yeah, listen, I think you can have influence.
Speaker 5 (45:59):
There were a few years into retirement. How do you
measure winning today?
Speaker 3 (46:05):
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 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.
Speaker 2 (46:25):
So I'm like, yes, we got to win into so Jay.
Speaker 5 (46:28):
So many times I get calls from founders and they're
seeing serenadventures in and I call Serena's like, we're not
quite in.
Speaker 2 (46:33):
Yet, guessing people like to wave that out exactly. Yeah.
Speaker 5 (46:39):
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 2 (46:51):
Oh easy.
Speaker 3 (46:53):
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 to San Francisco
(47:14):
and I worked hard there. I had to fight my
way to even figure out a way to get the
idea of what these investments are like. So it's really
just about hard work. It's nowhere around it. You can't
go around, you can't go you have to go right
through it, and then everything have fall into place.
Speaker 2 (47:30):
Love that this has been great fun and have fun.
Are you having fun? I am yeah. Yeah.
Speaker 3 (47:39):
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.
Speaker 2 (47:50):
And I've been doing that lately and that has made.
Speaker 3 (47:52):
Me just appreciate just being around and that makes my
day even better.
Speaker 2 (47:58):
So it's something new. I'm trying. Sorry, I'm just tired
to tell you.
Speaker 5 (48:01):
Gratitude is very powerful, right it is? Thank you, this
has been awesome, awesome, thank you, thanks for having me that.
Speaker 1 (48:16):
The Deal is a production from Blueberg Podcasts and Bloomberg Originals.
The Deals hosted by Alex Rodriguez and Jason Kelly. Our
producers are Victor Veyaz and Lizzie Phillip. Our story editor
is Sidartha Mahonta. Our assistant producer is Stacy Wong. Blake
Maples is our sound engineer. Rubob Shakir is our creative director.
(48:38):
Our 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 Kamiski,
Brendan Newnam, Kelly Laferrier, Ashley Hoenig, Trey Shallowhorn, Kyle Kramer,
(48:59):
and Andrew Bardon. Additional support from Rachel Scarmazino, Elena Los Angeles,
Vanessa Perdomo and Anna Masarakis. David Dominguez is our director
of photography. Our camera operators are Sage Passetti and Angela
Reyes Latta Our gaffer is Viper Higgins, and our grip
is Courtney Poyser. Katia Vanoy is our video editor. You
(49:24):
can also watch the deal on Bloomberg Originals YouTube and
Bloomberg Television. Thanks for listening.
Bloomberg Audio Studios, podcasts, radio news.
Speaker 2 (00:14):
It's a competition. I loved it.
Speaker 3 (00:16):
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. Like if I want to start
a business and my name isn't Serena Williams, I'm gonna
(00:37):
have to take something out of my house.
Speaker 2 (00:39):
I'm gonna have to go to the bank, like I'm
just gonna not be able to get VC money. But
we're changing that.
Speaker 4 (00:48):
All right, Alex Serena Williams the goat. I mean, it
doesn't get any better than her when it comes to
a professional athlete but also a fascinating business person. You
guys know each other like you've got to know each other,
especially as retired athletes, right, I.
Speaker 5 (01:06):
Mean, we know each other very well, and the irony
is very little to do with baseball or tennis. I
know Serena as an investor. She's been investing since twenty thirteen,
and she's passionate and she's good and she's as discipline
and she has big, big plans which you'll hear about.
Speaker 2 (01:22):
Yeah.
Speaker 4 (01:22):
I mean what I took away from this, probably more
than anything, was how early on she was identifying business
and even this notion her father essentially saying the majority
of your money you're going to.
Speaker 2 (01:35):
Make off the court.
Speaker 4 (01:37):
She has a great bit that I won't spoil about
the checks from the tournaments, but you know this notion
that she identified early on that there were opportunities fashion
certainly being one of them.
Speaker 2 (01:49):
But then how she became an investor is so interesting,
it really is. I know her well and I was
surprised on how much she opened up. Yeah, but there's
no doubt that she has the same discipline and passion
for investing yeah, as she did for being to go
in tennis.
Speaker 4 (02:04):
And let's keep in mind this is a career during
which she earned almost half a billion dollars. One of
her earliest deals is with Puma, and one of the
things that that does for her is it unlocks her
potential when it comes to fashion, because all of a sudden,
she's helping design her own outfits and we know the
cultural impact what she wore had.
Speaker 5 (02:27):
And I felt that in real time, the impact that
she made. I also thought it was really interesting mister Williams,
her father and what impact he had not only a
great inspiration person for her, but a great teacher in
life for both girls well.
Speaker 4 (02:40):
And also the idea that her father, who really set
it all up for them, then essentially said, you manage
your own money, figure it out. And so clearly that
was something that drove her to make a lot of
these key decisions. And then as she's going on in
her career going to Silicon Valley standing investing, and this
(03:03):
is something you guys get into and swap notes on
understanding brands. Bloom is one thing, Nike is a whole
different thing. You both have a relationship with that company.
And so her awareness of the power of brands and
the power of her own brand.
Speaker 5 (03:18):
This is truly a business story. I mean, the father
is like a great founder. Yes, he was a great visionary,
he was a great marketer.
Speaker 2 (03:25):
It was brilliant.
Speaker 5 (03:33):
On this episode of the Deal, Serena Williams, all right,
so please introduce yourself.
Speaker 3 (03:48):
All right, Well that's I never really get asked that,
but I mean you asked me to come here, so
I know I'm Serena.
Speaker 2 (03:56):
I like to go by Serena and what else?
Speaker 3 (04:00):
So am I gonna say? That's really putting me on
the spot.
Speaker 2 (04:02):
How do you how do you describe yourself these days?
Speaker 3 (04:04):
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.
Speaker 2 (04:12):
We'll go with that. You know, this notion of 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 3 (04:32):
Yeah, 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
(04:53):
after you won your tournament, and I would always forget
to get the checks.
Speaker 2 (04:56):
So at the end of the year they.
Speaker 3 (04:57):
Would always have to say, so we have all these
checks for you.
Speaker 2 (04:59):
I'm like, oh my god, So it was you would
literally forget to pick up the checksually, and.
Speaker 3 (05:04):
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 want to win championships and
(05:26):
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.
Speaker 2 (05:33):
And obviously it's great.
Speaker 3 (05:34):
Like you know, I really everything that I have, Believe me,
I worked really hard for nothing really came for free,
and nothing came easy. Like I think everything was super
hard working for me. But 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
(05:56):
me going forward?
Speaker 5 (05:58):
So, Serena, when we were thinking about this show, so
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 2 (06:09):
Yeah, but I'm.
Speaker 6 (06:10):
Interested to know what motivates you today when you're used
to being a champion, used to winning, and so that's
something that I'm always motivated by is success and what
a success.
Speaker 3 (06:23):
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. For me, success right now
is having great investments. I think a lot of people's
success is being a mom or 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
(06:43):
for me, the motivation is definitely success.
Speaker 5 (06:47):
Both of us played for a couple 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 ninety
percent of my money came from playing baseball on the
field with you is ecxact opposite.
Speaker 2 (07:05):
With YOURSS marketing?
Speaker 5 (07:06):
Yeah, 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 2 (07:16):
Yeah, it's so different, right.
Speaker 3 (07:18):
I think it's really interesting how I learned early on
that your paycheck from tennis maybe that's why I forgot them.
It should be your small should be your smallest earning.
Oh that's 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
to partner with, because for me, it's also about being
(07:39):
very authentic with those partnerships, not necessarily partnering with a
company that either doesn't believe in what you're doing.
Speaker 2 (07:47):
Or you don't really use and utilize.
Speaker 3 (07:50):
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 you know, gave back in
some sort.
Speaker 2 (07:59):
Of way, shape or form. So fair to say your
earliest business advice came from your dad. Most of my.
Speaker 3 (08:05):
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 had reporters coming out
(08:28):
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 social media wasn't a thing back then, So
because of the way he was getting that attention, it
was able to push ups, push us up.
Speaker 2 (08:43):
To the top.
Speaker 3 (08:44):
Obviously, our wins counted as well, which helped keep us
up there in the early ages, 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 he my first
checks from whether it was Puma, Like I got these
(09:06):
huge checks. He's like, you figure it out.
Speaker 2 (09:08):
And so we had to figure it out.
Speaker 3 (09:09):
And I'm literally living at his house in the bedroom.
Speaker 2 (09:12):
And next time, how old are you at this? I
was sixteen?
Speaker 3 (09:15):
Wow, And he's like, you know, most parents, you know,
they take your money and oh 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.
Speaker 2 (09:33):
Us to do that. You've said that wasn't as much
about the money.
Speaker 4 (09:37):
It was about validation and putting you in a position
to be in control in a way that you weren't before.
Speaker 2 (09:44):
Take us back to that mode. That's a fascinating deal.
Speaker 3 (09:47):
Puma is an incredibly fascinating deal. My dad negotiate everything,
and I have to say Puma was probably about the
money a little bit forgetting and I was like, it
was a lot of money. I remember I was sixteen
years old. I had an opportunity to be with other
companies but they passed.
Speaker 2 (10:01):
So there was this deal that Reebok.
Speaker 3 (10:04):
Wanted to do with me and Venus combined, and my
dad and 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. Yeah, So we went to la Arnan.
Milshan at the time was one of the biggest shareholders
in Puma. They were all in Hollywood, like he also
(10:25):
is like New Regency and owns all these it was
producing all these films. We're in this Hollywood studio, walking
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 sixteen. My dad's negotiating. They're going
back and forth, and he wants me there for the
(10:46):
whole time to make sure I know.
Speaker 2 (10:49):
What to do in the future. You're literally falling asleep
at the table. I pass out. I'm not following asleep.
I pass out at some point. Wow, you know.
Speaker 3 (10:56):
I eventually wake up and they're still at it, and
I'm just so upset.
Speaker 2 (11:00):
But what a learning experience.
Speaker 3 (11:02):
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
me and they say, what do you want to do?
And I tell them exactly what to do, but they
obviously deliver the message, but it's super connected. We have
(11:25):
such a great relationship when it comes to negotiating. They
really trust my advice and my vision and where to
go with it. And all start at such a young age.
But I also learned from that task for Equity because
I didn't at that time, which I.
Speaker 2 (11:37):
Probably should have.
Speaker 3 (11:39):
And then I ran into our non year a couple
of years ago and he's like, yeah, you should have
did equity. I'm like, thanks, are not you know you
should have said it. It'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 2 (11:59):
Because there was a little bit of risk on both sides.
Speaker 3 (12:01):
It was it was 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, you know, doing really amazing things
(12:24):
at winning and I won a Grand Slam less than
a year later after signing, So not a lot of
risk for them, not a lot of risks really, but
and I think they saw that it was a lot
of potential.
Speaker 2 (12:36):
Yeah, they saw it early on.
Speaker 5 (12:38):
I remember, I don't know a lot about tennis, you know,
but what I do good because I.
Speaker 2 (12:43):
Don't know a lot about baseball.
Speaker 5 (12:44):
I know that, I know that, but we already know this.
This is more for the audience. But one of the
things I remember when I was like twenty five twenty six,
I always used to remember you not for your great plays,
but for your fashion. Oh yeah, And I just thought,
like I wanted to see what Serena was wearing a
yet dresser and what pumas And I just thought that,
and then the winter connection. What is it about fashion
(13:08):
that motivates you? Because you've always been on point?
Speaker 3 (13:11):
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
(13:31):
attachment to fashion. And eventually I learned how to sew
and how to make things from old socks, and then
eventually I would use old clothes when I was literally
living in Compton and just learned how to do the
craft right.
Speaker 2 (13:43):
And that's kind of how it started.
Speaker 3 (13:46):
And eventually I went to fashion school, which is a
whole story in its own.
Speaker 2 (13:49):
I feel like I have a zillion stories.
Speaker 4 (13:52):
We're here for them, but how much times us as
you are, it.
Speaker 3 (13:58):
Was gonna have to be like a two part session.
And so then yeah, so eventually I went to fashion school.
And then one thing I did love and when I
first came out with Pumas, that gave me like a
lot of opportunities to design some of the stuff that
I was wearing, or at least say like this is.
Speaker 2 (14:14):
What I want to wear. And I knew that.
Speaker 3 (14:16):
Listen, I don't look like everyone else out here, I
don't play like everyone else, and I'm different.
Speaker 2 (14:21):
It's clear that I'm different.
Speaker 3 (14:23):
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,
and so Puma understood that, and then that kind of
started the craze. And obviously Nike came on right after
and just amplified at times a zillion, which made it
even more cool. Which made me wear like a jean
skirt in New York, which was kind of one of
(14:45):
my favorite oullis. I was insane. I still can't believe
when I did that.
Speaker 2 (14:48):
Yeah, I should have won that year. But anyway, but.
Speaker 4 (14:51):
Let's talk about some of those specific fashion choices. The
one that I think so many people remember is the catsuit.
Speaker 2 (14:58):
The catsue was legendary, So.
Speaker 4 (15:00):
Like, take us back to that moment, like that choice,
Like what does that feel like when.
Speaker 2 (15:05):
You put that on?
Speaker 4 (15:06):
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 (15:12):
Absolutely, So that choice was definitely a Puma designer and
she was like, we want you to do this cat
suit and I was like, whoa, this is crazy, this
is so cool. So the US 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 cat suit, which if you look at the Open
(15:33):
in that year, I think it was two thousand and two.
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 catsuit.
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 asked
(15:54):
a few girls in the locker room what they think,
and they're like, oh.
Speaker 2 (15:57):
That's crazy. You can't wear that. You can't wear that.
Speaker 3 (15:59):
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 cat suit on, I zipped it up,
and I just walked out.
Speaker 2 (16:08):
It was just like, oh my god. And then it
was just it was no looking back after that.
Speaker 4 (16:12):
Really, So did it feel as no important in the moment?
It didn't know Okay, you didn't know because that changed
me everything.
Speaker 3 (16:20):
I always say, that's how that's when I got famous.
Wasn't the six Grand slams I won before that?
Speaker 2 (16:27):
It was a cat suit? Yeah, I mean I was
pretty young.
Speaker 3 (16:30):
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,
not every woman, but a lot of women at that
time had a different type.
Speaker 2 (16:44):
Of figure than I did. And so I was really different.
Speaker 3 (16:47):
I was basically a lone soldier and 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.
Speaker 2 (16:57):
And so it was.
Speaker 3 (16:59):
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, right right.
Speaker 5 (17:10):
You looked amazing, Okay, I remember, I mean at that
time it was no Instagram, but you broke the internet.
Speaker 2 (17:16):
It was Google everywhere.
Speaker 5 (17:17):
And I remember a lot of my teammates and buddies
from back home sending me the picture saying, look how
fly she looks?
Speaker 2 (17:22):
Right?
Speaker 5 (17:22):
But in baseball, Jason it sounds like it's the same
thing in tennis, where you look good.
Speaker 2 (17:27):
You feel good, absolutely good.
Speaker 5 (17:29):
Yeah, and I love that because that's exactly how I
felt as a player.
Speaker 4 (17:33):
Absolutely, But I think we shouldn't underestimate the cultural power
that that moment had.
Speaker 3 (17:41):
And it crossed so many people that weren't watching tennis, right,
people outside that were okay, maybe incompetent because we were
from there, but like every neighborhood at that point was
watching it. But it just crossed all borders and many
people from all walks of life want and just kind
of watched tennis. And it was just like being that
cultural person to bring in people that don't normally watch
(18:06):
the sport. Again, 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 of myself and my sister, It all start at
these moments. It's crazy to think about I've never even
voiced this stuff, like, oh my god.
Speaker 2 (18:23):
But that, I mean, it changes the business of tennis. Absolutely,
also changes the business of Serena, right, 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, that the impact you were having off the.
Speaker 4 (18:40):
Court just becomes magnified. To your point, what does it
feel like as that is starting to take root.
Speaker 3 (18:48):
It definitely feels different as that starts to take place.
There were more contracts and more deals coming in and
more time.
Speaker 2 (18:56):
But that's what it is about.
Speaker 3 (18:58):
Right Again, I'm thinking I was when I was really young,
that you make your money off the court ten it
should be your smallest check in our sport at that time,
and so I'm thinking, okay, this is again, this is
what my dad was talking about, like how did he
know 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 I want to
(19:20):
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.
Speaker 2 (19:26):
Impact off the court?
Speaker 3 (19:27):
Yeah, because it was always about having a plan B,
even though I didn't necessarily need it, but it was
just something etched in my head my dad. You could fall,
anything could 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, Okay, well,
this is something that I can kind of do in
(19:48):
the future.
Speaker 2 (19:52):
Coming up.
Speaker 4 (19:52):
Serena talks about how she got into investing, how she
signed with Nike, and how she met and works with
her husband, Alexi so Henian.
Speaker 5 (20:12):
I remember a story with Phil Knight. And I was
with Nike ever since I was seventeen years old, and
we had kN Griffith Junior and 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 Griffy. And at that time we had Jordan, we
had Griffy and that was the gold standard.
Speaker 2 (20:32):
And I'll never forget.
Speaker 5 (20:32):
We went to breakfast on a Saturday morning 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 rewrite
your contract. And I said, well, define a big market.
He said, New York, La Chicago. I said, okay. The
(20:53):
day I got where, George Steiermanter called me and traded
me to New York. I got a call from Phil
Knight and he said gay on wow and because of
his loyalty, no contract, just a handshake. I've been with
Nika since. I've never worn another shoe. But when I
got to New York, I sends things were different, the impact,
all the opportunities that came. When did you feel that
(21:15):
things were different and that whatever brand you went with
actually had a riple effect not only domestically but around
the world.
Speaker 3 (21:21):
Yeah, I think things got really different. I do remember,
actually now that you mentioned, I actually forgot about the
Seattle Mariners.
Speaker 2 (21:30):
Yeah, here you go. She's a baseball ye.
Speaker 3 (21:33):
Right, Yeah, 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 cat suit, and not because of the catsuit.
I think it was me winning the French Open, Wimbledon
and the US opened in the same year. It's been
(21:54):
years and 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 sells
and to dominate at that time with everyone that was
so great was just unheard of. And so I think
(22:17):
winning that US Open just solidified everything and the outfit
and it.
Speaker 2 (22:21):
Was like, well, this, this, this, this kid is amazing.
How do I change that?
Speaker 3 (22:26):
How do I say, Okay, 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, I'm at the Larius Awards or I'm here
and I'm actually winning these awards and you know, except
for the one, and I'm still bitter about I'm not
(22:49):
competitive at all, definitely not.
Speaker 2 (22:53):
It doesn't play with me at all. And so how
do you take advantage of that?
Speaker 4 (22:58):
Like what's the process by which means you've been with
Jill for a long time, Jill Smuller, are the conversations different?
Speaker 2 (23:04):
Are your ambitions growing? Like?
Speaker 4 (23:06):
How do you activate that moment where you are blowing
up even more?
Speaker 3 (23:11):
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
(23:33):
got ours 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's works at w ME. 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.
Speaker 2 (23:53):
Really.
Speaker 3 (23:53):
I think your partner exactly like a partner. And how
long have you guys been, Oh, since two thousand, that's
in question. 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,
(24:15):
like I want to be with At the time, I
wasn't with Gatorade, and I was like, my lifelong.
Speaker 2 (24:20):
Dream was to be with Gatorade. Because I remember.
Speaker 3 (24:23):
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.
Speaker 2 (24:40):
And I would always.
Speaker 3 (24:41):
See the mic I want to be like Mike 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 corporate?
Speaker 2 (24:51):
If it was corporate with corporate companies you want to
be with? And does that resonate with you?
Speaker 4 (24:54):
I mean, because I'm sitting between these two very deliberate
business people who have cott into this from an early
I mean, do you remember identifying brands that you wanted.
Speaker 2 (25:04):
To be with? Because it sounds like you had a
literal list.
Speaker 5 (25:07):
I mean, for me, Gatoray 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
want 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' woard right and
(25:27):
we all want to be like those. I looked up
to Michael and Magic and Bird.
Speaker 2 (25:32):
Everyone looked up to Michael, A girl, a guy, whatever.
Who did you look up to? Who inspired you when
it came to branding? Michael Michael Jordan.
Speaker 3 (25:43):
I think he really was able to do branding in
a different way, and the plumb that he has walking
around is just second to none tennis wise. I was
actually inspired by Monica Sellis.
Speaker 2 (25:53):
I just liked her.
Speaker 3 (25:55):
I thought she was really cool and I liked how
she grunts.
Speaker 2 (26:01):
I do have a question.
Speaker 5 (26:02):
Was there a call where Joe called you and she said, I, 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
more than if you had a moment.
Speaker 3 (26:15):
I guess 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 4 (26:30):
And so let's talk about Nike for a second, because
obviously Puma does one thing, as you've alluded to, Nike
does something altogether. Absolutely, what was that negotiation, Like, what
do you remember about sort of getting into business with them?
Speaker 3 (26:45):
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
(27:06):
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 talk briefly globally, and because tennis
(27:29):
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 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 (27:49):
You talked about this moment in tennis that I want
to dwell in.
Speaker 4 (27:52):
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 at the time
(28:12):
or is it only apparent in retrospect.
Speaker 3 (28:15):
No, it was very apparent, Yeah, 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, oh God, or years that stay
professionals arena don't say that years that I was injured,
(28:38):
or years that you know, I didn't play. You could
just see the difference of you know, people that were
attending the matches or viewers.
Speaker 4 (28:47):
The US 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 2 (28:56):
That's just again, that's factual. I have to say.
Speaker 3 (28:59):
You feel that I took on a lot of that
pressure as the years continued. After ten years, you know,
I would feel that pressure of like, okay, it's it's
Serena going to be in New York and right it's
it was. It was like not the not the Serena Open,
but it was still like a lot of attention on
(29:22):
you know, myself, right, and Venus too, But it was
a lot of attention on.
Speaker 4 (29:26):
Me because the numbers are one thing, and the numbers
are great, but what's the Serene effect on Serena? You know,
like that pressure then in the in the sense of
you know that if you show up, that's better for tennis,
that's better for the the owner of the tournament.
Speaker 2 (29:42):
I think that I try to always remain humble.
Speaker 3 (29:45):
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, however,
that's going to be, it's going to be super amp
fire and it's not easy, but you do walk in
(30:07):
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,
and you know, they're just like they want that, And
a part of me is like, take it, because it's
a lot of pressure and it's a lot to hold
(30:28):
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
(30:48):
it's I would definitely prefer that pressure then not, if
that makes sense.
Speaker 2 (30:53):
Yeah, pressure is a privilege. It's right there right when
you walk out of the cot.
Speaker 3 (30:56):
Wow, it is your New York is your favorite turn.
Speaker 2 (30:59):
Wow.
Speaker 5 (31:00):
But Jayson, I want to segue to business because I
wasn't a call with Serena early on, and I was like, wow,
I wasn't expecting that, And not because I had a judgment.
Speaker 2 (31:12):
You know, I'll tell you why. I'll tell you why
because the.
Speaker 5 (31:14):
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. Where too much? But where
(31:37):
does that come from? Is it from your playing days?
Asenially details?
Speaker 3 (31:41):
I feel like, yeah, I'm super tending 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 are you talking about? Like being on calls with
(32:02):
founders 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 not own the company,
but I'm the representative for the company from my firms
as sv CER and Adventures, and so I'm like literally
on the calls. I'm literally helping them understand how their fundraise.
(32:23):
I'm looking at their decks and so it's a lot.
Speaker 2 (32:26):
So I decide, Okay, that's too much. I can't go
on like this.
Speaker 3 (32:30):
But I truly love investing yea, 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 some little cash, Like
how did I not invest in Facebook?
Speaker 2 (32:48):
How I invest in airbnber? How did I miss.
Speaker 3 (32:51):
Google or like you know, all these companies. I don't
know if you ever thought of that, but I'm.
Speaker 2 (32:54):
Like, I missed a bunch, how like why?
Speaker 3 (32:57):
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.
Speaker 2 (33:10):
I've got to win us this year. I've got a
padies bills.
Speaker 3 (33:16):
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 2 (33:29):
Yeah, and I would ask questions.
Speaker 3 (33:31):
I remember even just sitting in Pinterest at the time
one day and just learning from the founder there and
just just just being a sponge and just trying to
understand the business, understand stand investing, understand all this stuff
a little bit more.
Speaker 2 (33:46):
And that's kind of how it all started.
Speaker 4 (33:48):
Unfortunately, to your point about the Bay Area and underrepresentation
still there. Oh is it two percent of VC funding
less goes to women, you know, even fewer when you
when you start to go to other categoryories of underrepresentation?
Was that part of the DNA of Serena Ventures from
the beginning?
Speaker 2 (34:07):
How did that all?
Speaker 3 (34:08):
Another story? If you guys want to hear it.
Speaker 2 (34:10):
So I started, We're literally here for your stories.
Speaker 3 (34:16):
So I started investing, and then I somehow got into
early stage investing.
Speaker 2 (34:20):
I didn't realize that it was called early stage.
Speaker 3 (34:23):
I just liked companies that were starting, and then I
liked growing them. One of them was Masterclass. I remember
meeting the guys. 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 felt loved what they were doing
and I was like, I want to be a pier
(34:44):
of this. And so it was just finding several different
companies like that in Masterclass obviously became Masterclass.
Speaker 2 (34:50):
Ye.
Speaker 3 (34:50):
And one day I was at a conference at JP
Morgan and Jamie Diamond was on stage and he was
talking to this woman named Karen Sideman Becker. But she's
on stage and she's talking about women and VC and
how women get less than two percent of all VC money.
But I'm thinking, she misspoke. That's so embarrassing, Like I'm embarrassed.
Speaker 2 (35:12):
For her, right right, right.
Speaker 3 (35:14):
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 can said the number wrong, but something about
two percent less than two percent, And she was like,
(35:35):
you know, Karen, so she's like the woman I dream
of being, and she's just like she just tells me everything,
and she just gives me all this amazing information the
span of ten minutes, and I'm like, I didn't know.
And so that's how Stain Adventures happened from that moment before,
and I was like, I need to start an investment
(35:55):
company and I'm not 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, ended up getting about sixteen
unicorns and 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.
Speaker 2 (36:16):
Fund first go around.
Speaker 3 (36:17):
Yeah, until you get to know me and you get
to know the story, and you need to know all
the investments that I had done.
Speaker 2 (36:23):
And that's what happened.
Speaker 5 (36:24):
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.
Speaker 2 (36:35):
But we're both former athletes.
Speaker 5 (36:37):
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
early on.
Speaker 2 (36:47):
Yep, how did that make.
Speaker 5 (36:48):
You feel when you went to LP's potential piece to
raise capital.
Speaker 2 (36:52):
It's a competition. I loved it.
Speaker 3 (36:54):
It's what I It gave me energy. It gives me
life in telling me n 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, Like, if
(37:14):
I want to start a business and my name isn't
Serena Williams, I'm gonna have to take something out of
my house.
Speaker 2 (37:19):
I'm gonna have to go to the bank.
Speaker 3 (37:20):
Like it's not I'm not gonna be I'm just gonna
not be able to get VC money.
Speaker 2 (37:24):
But we're changing that.
Speaker 3 (37:26):
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 as
sixty eight percent women are 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
(37:46):
hear your story if you're a personal 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 a story, if
they pass, they pass, but at least you get them
thinking to get them here, and maybe they'll invest in
another fund that is doing the same thing, maybe that
has been around a little bit longer, with the track
record a little bit longer, but they'll come.
Speaker 2 (38:07):
Around to us at some point. And that's kind of
how I feel.
Speaker 3 (38:09):
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 4 (38:19):
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 2 (38:28):
It does, and I don't want it to be.
Speaker 3 (38:32):
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, and without me realizing it, I was always
(38:55):
drawn to this space and it put me here and
I'm not going to change. I am get a step
back up 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 4 (39:10):
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
(39:33):
in terms of investments, What do you think your influence
has been on him?
Speaker 3 (39:38):
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.
Speaker 2 (39:59):
And also just.
Speaker 3 (40:02):
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 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
(40:22):
because we were talking about investments all these years ago.
Speaker 2 (40:25):
That's how you met, That's how we met. Yeah, we
just got to tell us that story.
Speaker 3 (40:29):
Okay, you asked, you know, 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 where you were staying at, there is these American
(40:50):
people that were here for a tech conference. And so anyway,
so fast forward to a couple days later, I have
a match that day, and 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 six
(41:10):
pm or five pm. So I'm like, I don't want
to be in the room till five pm today for
by chance.
Speaker 2 (41:16):
So I was like, I just can't do this today.
I just can't.
Speaker 3 (41:18):
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.
Speaker 2 (41:24):
I would never be seen. I was a ghost.
Speaker 3 (41:26):
So I went to have breakfast. Who wow, 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 eleven because 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
(41:48):
had like a pool, and so I went to this
other restaurant with this massive pool. There's all these chairs
and there's all these tables, and there's this pool and
there's an other side of the pool there's chairs.
Speaker 2 (41:57):
And so we're the only people.
Speaker 3 (41:59):
It's me, Jill and my assistant at the time, and
he was Australian that's going.
Speaker 2 (42:03):
To come back to.
Speaker 3 (42:04):
So we sit down the only people there, and we
order our breakfast and we're just talking and laughing and
this guy walks in with the computer and he sits
down right next to us, at the table, right next
to us, and I'm like so upset. I'm like, do
you see how big this area is? B like, do
I look? Does it look like we want people next
(42:26):
to us?
Speaker 2 (42:27):
Like? It's huge?
Speaker 3 (42:29):
And I'm like, oh my goodness. So my assistant at
the time his name was Zane. He's like, and it
there's a allfl accent. I'll see, access is the worst.
And there's a rat over there, and he's saying that
there's a rat. There's a rat, because we're trying to
get him to go away.
Speaker 2 (42:46):
Oh my god.
Speaker 3 (42:47):
And then he looks up and he's like, is there
really a rat?
Speaker 2 (42:55):
And he's is it really a rat?
Speaker 3 (42:56):
Because I'm from Brooklyn and I'm not afraid of rats.
And I was like, oh, you're for Brooklyn. So that's
how we started talking. And then so he said, I
was like, what are you here for? And he's like, oh,
I'm here for the conference. It's like, oh, cool, who
are you here to see? And he's like, oh, I'm
not seeing anybody. I'm speaking. I mean, I'm like, okay,
this guy has excuse me. And anyway, he started talking
(43:17):
about he did read it, and he started read it
and then of course I hadn't heard of it.
Speaker 2 (43:21):
But you know, now you get to know me. I'm like,
I don't hear of anything.
Speaker 5 (43:24):
It's right, right, right, But what's interesting about this? Like Jace,
I've been in a lot of calls in zooms with
Serena and a lot of calls with Alexis. And by
the way, they're both so different, but they compliment 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.
Speaker 2 (43:41):
They keep it a very church and state.
Speaker 4 (43:42):
Yeah yeah, so what if you've learned from him as
an investor, we keep it very church and state.
Speaker 3 (43:48):
But I do go to him for advice. I'm like, okay,
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 I always pick his brain on
when it comes to early stage investments in terms of sectors,
like what's going to be another sector that's going to
be exciting, whether it's AI or He's probably already invested
(44:11):
in companies way before that sector is even popular, which
is honestly incredible.
Speaker 4 (44:16):
I will say one of my favorite stories, because you
know we followed sports very closely, was your influence on
me angel City investment, which, as at least as it's
been told her as he's told it, Olympia was, you know,
getting into playing soccer.
Speaker 3 (44:31):
So this is a false story. Yeah, but let's correct.
Speaker 2 (44:34):
Yes, let's correct it.
Speaker 3 (44:35):
Okay, Okay, I'm not a pro, so I'm like pro tennis.
So the fact that Olympia was playing soccer, I was
already salty about that. I think he kind of did
that deal to make me mad because I'm like, let's
do something in tennis. Yeah, because obviously let's amplify tennis, right,
But that's that's the real.
Speaker 4 (44:53):
But the part of the story that I love is that,
and you tell us whether this is true or not,
is that the east line should.
Speaker 2 (45:00):
Be you need to do something for equal pay in sports.
Is that right?
Speaker 3 (45:04):
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 it's
(45:24):
not even a conversation to me, it's not even close.
I actually watched soccer, and I love women's soccer. I
watched 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 tennis.
Speaker 2 (45:45):
I was like, no, but I did win.
Speaker 3 (45:49):
Because Olympia does not like soccer anymore.
Speaker 2 (45:51):
Oh is that right?
Speaker 3 (45:52):
Well, for now she changes their mind a lot. She
does like tennis a little bit more now, So I'm like.
Speaker 2 (45:56):
Yes, yeah, listen, I think you can have influence.
Speaker 5 (45:59):
There were a few years into retirement. How do you
measure winning today?
Speaker 3 (46:05):
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 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.
Speaker 2 (46:25):
So I'm like, yes, we got to win into so Jay.
Speaker 5 (46:28):
So many times I get calls from founders and they're
seeing serenadventures in and I call Serena's like, we're not
quite in.
Speaker 2 (46:33):
Yet, guessing people like to wave that out exactly. Yeah.
Speaker 5 (46:39):
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 2 (46:51):
Oh easy.
Speaker 3 (46:53):
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 to San Francisco
(47:14):
and I worked hard there. I had to fight my
way to even figure out a way to get the
idea of what these investments are like. So it's really
just about hard work. It's nowhere around it. You can't
go around, you can't go you have to go right
through it, and then everything have fall into place.
Speaker 2 (47:30):
Love that this has been great fun and have fun.
Are you having fun? I am yeah. Yeah.
Speaker 3 (47:39):
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.
Speaker 2 (47:50):
And I've been doing that lately and that has made.
Speaker 3 (47:52):
Me just appreciate just being around and that makes my
day even better.
Speaker 2 (47:58):
So it's something new. I'm trying. Sorry, I'm just tired
to tell you.
Speaker 5 (48:01):
Gratitude is very powerful, right it is? Thank you, this
has been awesome, awesome, thank you, thanks for having me that.
Speaker 1 (48:16):
The Deal is a production from Blueberg Podcasts and Bloomberg Originals.
The Deals hosted by Alex Rodriguez and Jason Kelly. Our
producers are Victor Veyaz and Lizzie Phillip. Our story editor
is Sidartha Mahonta. Our assistant producer is Stacy Wong. Blake
Maples is our sound engineer. Rubob Shakir is our creative director.
(48:38):
Our 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 Kamiski,
Brendan Newnam, Kelly Laferrier, Ashley Hoenig, Trey Shallowhorn, Kyle Kramer,
(48:59):
and Andrew Bardon. Additional support from Rachel Scarmazino, Elena Los Angeles,
Vanessa Perdomo and Anna Masarakis. David Dominguez is our director
of photography. Our camera operators are Sage Passetti and Angela
Reyes Latta Our gaffer is Viper Higgins, and our grip
is Courtney Poyser. Katia Vanoy is our video editor. You
(49:24):
can also watch the deal on Bloomberg Originals YouTube and
Bloomberg Television. Thanks for listening.
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