Serena Williams Wants to Conquer Wall Street

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It's a competition. I loved it.

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 have to take something out of my house.

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.

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.

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.

Yeah.

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.

Make off the court.

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.

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.

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.

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.

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 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.

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.

It was brilliant.

On this episode of the Deal, Serena Williams, all right, so please introduce yourself.

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.

I like to go by Serena and what else?

So am I gonna say? That's really putting me on the spot.

How do you how do you describe yourself these days?

How do I describe myself? I describe myself first as a mom. I'm a mom, I'm a businesswoman, and I'm a free spirit.

We'll go with that. 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.

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 after you won your tournament, and I would always forget to get the checks.

So at the end of the year they.

Would always have to say, so we have all these checks for you.

I'm like, oh my god, So it was you would literally forget to pick up the checksually, and.

At the time I had an accountant who would be like, Serena, like they've sent me all these checks that you would forget to get from the tournaments. And so so with that being said, that was never my motivation. To be honest, for my motivation and looking at the success that I

And obviously it's great.

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 me going forward?

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?

Yeah, but I'm.

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.

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 for me, the motivation is definitely success.

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.

With YOURSS marketing?

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.

Yeah, it's so different, right.

I think it's really interesting how I learned early on that your paycheck from tennis maybe that's why I forgot them. It should be your small should be your smallest earning.

Or you don't really use and utilize.

So I think throughout my whole career, I wanted to make sure that those partnerships are very authentic. They spoke to me, and they also you know, gave back in some sort.

Of way, shape or form. So fair to say your earliest business advice came from your dad. Most of my.

Business advice came from my dad early on. He is incredibly, incredibly smart. I think he is way before his time. Everything that he did, I think even when it came to marketing us as tennis players. Tennis is a very expensive sport and you can't make it from Compton. But I think it was his marketing that got us that attention, that garnered those press articles that had reporters coming out or else we would have a very difficult time getting

To the top.

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 huge checks. He's like, you figure it out.

And so we had to figure it out.

And I'm literally living at his house in the bedroom.

And next time, how old are you at this? I was sixteen?

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.

Us to do that. You've said that wasn't as much about the money.

It was about validation and putting you in a position to be in control in a way that you weren't before.

Take us back to that mode. That's a fascinating deal.

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.

So there was this deal that Reebok.

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 is like New Regency and owns all these it was

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.

I eventually wake up and they're still at it, and I'm just so upset.

But what a learning experience.

I learned so much from that experience, and ever since then, I'm usually behind the scenes. I don't do the negotiating, but I actually am behind the scenes, but no one really knows that it's actually me. It was my agent or whoever. If they get a deal, they come to 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

Probably should have.

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.

Because there was a little bit of risk on both sides.

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.

Yeah, they saw it early on.

I remember, I don't know a lot about tennis, you know, but what I do good because I.

Don't know a lot about baseball.

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 that motivates you? Because you've always been on point?

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

And that's kind of how it started.

And eventually I went to fashion school, which is a whole story in its own.

I feel like I have a zillion stories.

We're here for them, but how much times us as you are, it.

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.

What I want to wear. And I knew that.

Listen, I don't look like everyone else out here, I don't play like everyone else, and I'm different.

It's clear that I'm different.

I am a black girl and I'm playing tennis, and so I need to stand out. I don't want to wear the same kind of outfits that everyone else was wearing, 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 my favorite oullis. I was insane. I still can't believe when I did that.

Yeah, I should have won that year. But anyway, but.

Let's talk about some of those specific fashion choices. The one that I think so many people remember is the catsuit.

The catsue was legendary, So.

Like, take us back to that moment, like that choice, Like what does that feel like when.

You put that on?

Because you have said I love this quote from you. It says when there was an edge to how I look, there was an edge to my game.

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 in that year, I think it was two thousand and two.

That's crazy. You can't wear that. You can't wear that.

And I'm like, oh, I know, I know. And for whatever reason, right before walk off, I just changed really fast. I threw the cat suit on, I zipped it up, and I just walked out.

It was just like, oh my god. And then it was just it was no looking back after that.

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.

I always say, that's how that's when I got famous. Wasn't the six Grand slams I won before that?

It was a cat suit? Yeah, I mean I was pretty young.

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.

Of figure than I did. And so I was really different.

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.

And so it was.

Without knowing, it was really leaning into that. And and again I didn't know, I was just doing it. And then it was a lot of memes, even before memes were memes, right right.

You looked amazing, Okay, I remember, I mean at that time it was no Instagram, but you broke the internet.

It was Google everywhere.

And I remember a lot of my teammates and buddies from back home sending me the picture saying, look how fly she looks?

Right?

But in baseball, Jason it sounds like it's the same thing in tennis, where you look good.

You feel good, absolutely good.

Yeah, and I love that because that's exactly how I felt as a player.

Absolutely, But I think we shouldn't underestimate the cultural power that that moment had.

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

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.

Court just becomes magnified. To your point, what does it feel like as that is starting to take root.

It definitely feels different as that starts to take place. There were more contracts and more deals coming in and more time.

But that's what it is about.

Right Again, I'm thinking I was 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

Impact off the court?

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 the future.

Coming up.

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.

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.

And I'll never forget.

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 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

Yeah, I think things got really different. I do remember, actually now that you mentioned, I actually forgot about the Seattle Mariners.

Yeah, here you go. She's a baseball ye.

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 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

Was like, well, this, this, this, this kid is amazing. How do I change that?

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 competitive at all, definitely not.

It doesn't play with me at all. And so how do you take advantage of that?

Like what's the process by which means you've been with Jill for a long time, Jill Smuller, are the conversations different?

Are your ambitions growing? Like?

How do you activate that moment where you are blowing up even more?

Well, Jill has been amazing. I feel like leaning into having someone a woman in that position, I think, quite frankly, maybe things would have been different if I had a guy like maybe I would have had an extra deal or two, but it was really about leaning in into having a woman on my team. Interesting owning that we got ours when the time was due, when the time was ready, but it was sometimes where we had to

Really.

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, like I want to be with At the time, I wasn't with Gatorade, and I was like, my lifelong.

Dream was to be with Gatorade. Because I remember.

Walking around the corner from my tennis court, not my tennis court, the community court in Compton. We would walk to the convenience store and my dad would buy one Gatorade in a can and we would all have to share it. And it was like, I've always loved that, and I've always loved that story and I've always loved Gatorade.

And I would always.

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?

If it was corporate with corporate companies you want to be with? And does that resonate with you?

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.

To be with? Because it sounds like you had a literal list.

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 we all want to be like those. I looked up to Michael and Magic and Bird.

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.

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.

I just liked her.

I thought she was really cool and I liked how she grunts.

I do have a question.

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.

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.

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?

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 think they have an opportunity to market especially at the time. It's just like, you know, if you want to be

You talked about this moment in tennis that I want to dwell in.

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 or is it only apparent in retrospect.

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, 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.

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.

That's just again, that's factual. I have to say.

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 you know, myself, right, and Venus too, But it was a lot of attention on.

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.

I think that I try to always remain humble.

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 with your chest a little farther out, in your head

Yeah, pressure is a privilege. It's right there right when you walk out of the cot.

Wow, it is your New York is your favorite turn.

Wow.

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.

You know, I'll tell you why. I'll tell you why because the.

Questions you were asking were so thorough, you had done your due diligence. You were asking things about it has to fit with my brand, And I knew you would know all the numbers, but I didn't know how authentic you were going to be and how sincerely deeply in the weeds you would be. Where too much? But where does that come from? Is it from your playing days? Asenially details?

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 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

So I decide, Okay, that's too much. I can't go on like this.

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?

How I invest in airbnber? How did I miss.

Google or like you know, all these companies. I don't know if you ever thought of that, but I'm.

Like, I missed a bunch, how like why?

And I started to ask these questions, like why am I out here breaking my neck and sweating when I could have invested in these companies and I could still be doing the same thing, but I wouldn't have to be such dire.

I've got to win us this year. I've got a padies bills.

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.

Yeah, and I would ask questions.

I remember even just sitting in Pinterest at the time one day and just learning from the founder there and just just just being a sponge and just trying to understand the business, understand stand investing, understand all this stuff a little bit more.

And that's kind of how it all started.

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?

How did that all?

Another story? If you guys want to hear it.

So I started, We're literally here for your stories.

So I started investing, and then I somehow got into early stage investing.

I didn't realize that it was called early stage.

I just liked companies that were starting, and then I liked growing them. One of them was Masterclass. I remember meeting the guys. 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

Ye.

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.

For her, right right, right.

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

Fund first go around.

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.

And that's what happened.

So, Serena, as I hear you speaking, I can't help but think about like when I transitioned from baseball to business, and it's quite daunting, and I know for me there was some imposter syndrome.

But we're both former athletes.

I'm a man of color, you're a woman of color as you enter the world of capital raising, which is very difficult, especially when you haven't had the track record early on.

Yep, how did that make.

You feel when you went to LP's potential piece to raise capital.

It's a competition. I loved it.

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 I want to start a business and my name isn't Serena Williams, I'm gonna have to take something out of my house.

I'm gonna have to go to the bank.

Like it's not I'm not gonna be I'm just gonna not be able to get VC money.

But we're changing that.

And we don't only invest in women, we don't only invest in people of color. But we're putting that on a platform. Our portfolio right now as it stands 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

Around to us at some point. And that's kind of how I feel.

But I love talking to LPs and just getting that story told on a platform that a lot of people don't have, And so that is it's super amazing for us.

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?

It does, and I don't want it to be.

You know, my daughter wants to do a sport, and I'm like, you have to do a sport that's you're not breaking down barriers because mom has already done that and you don't need to do that. And so somehow I find myself in a similar story without trying. I think eventually you're just drawn to, you know, whatever you're drawn to, and without me realizing it, I was always drawn to this space and it put me here and

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 in terms of investments, What do you think your influence has been on him?

Well, I think my influence on him is just he really wants that success. He really wants to be seen as that best investor, and he is. He's such a great investor, and I'm like, you already have that, but he wants it to be even more amplified.

And also just.

Explaining to him and just giving him my insights of, you know, how to play the game, because you have to be able to play the game, whether you're investing or whether you are in sport. It's 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 because we were talking about investments all these years ago.

That's how you met, That's how we met. Yeah, we just got to tell us that story.

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

So I was like, I just can't do this today. I just can't.

So I left to go downstairs at breakfast. Now this is crazy, like come on, I mean I literally would even eat breakfast in my room.

I would never be seen. I was a ghost.

So I went to have breakfast. 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 had like a pool, and so I went to this

And so we're the only people.

It's me, Jill and my assistant at the time, and he was Australian that's going.

To come back to.

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 to us?

Like? It's huge?

And I'm like, oh my goodness. So my assistant at the time his name was Zane. He's like, 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.

Oh my god.

And then he looks up and he's like, is there really a rat?

And he's is it really a rat?

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 about he did read it, and he started read it and then of course I hadn't heard of it.

But you know, now you get to know me. I'm like, I don't hear of anything.

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.

They keep it a very church and state.

Yeah yeah, so what if you've learned from him as an investor, we keep it very church and state.

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

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.

So this is a false story. Yeah, but let's correct.

Yes, let's correct it.

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.

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.

Be you need to do something for equal pay in sports. Is that right?

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 not even a conversation to me, it's not even close.

I was like, no, but I did win.

Because Olympia does not like soccer anymore.

Oh is that right?

Well, for now she changes their mind a lot. She does like tennis a little bit more now, So I'm like.

Yes, yeah, listen, I think you can have influence.

There were a few years into retirement. How do you measure winning today?

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.

So I'm like, yes, we got to win into so Jay.

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.

Yet, guessing people like to wave that out exactly. Yeah.

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?

Oh easy.

It goes back to the very simple advice of work hard nothing and you know, nothing takes place of hard work. Like I was telling the story about me in Rome and how like going to breakfast was a thing because that's how hard I worked. It doesn't come easy. And I work for everything, whether it was winning championships or whether it's being an investor. I went to San Francisco and I worked hard there. I had to fight my way to even figure out a way to get the

Love that this has been great fun and have fun. Are you having fun? I am yeah. Yeah.

I think it's important to have fun. But I think it's important also to take a moment and just look up at the sky and give grace, or look at a tree and say I'm here, I'm alive today.

And I've been doing that lately and that has made.

Me just appreciate just being around and that makes my day even better.

So it's something new. I'm trying. Sorry, I'm just tired to tell you.

Gratitude is very powerful, right it is? Thank you, this has been awesome, awesome, thank you, thanks for having me that.

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. Our direction is from Jacqueline Kessler. Original music by Blake Maples, casting by Dave Warren. Our managing editor is David Ravella.