Re-Run: Serena Williams Wants to Conquer Wall Street

19:56He said, New York, LA, Chicago. I said, okay. The day I got where George Steinmetter called me and traded me to New York, I got a call from Phil Knight and he said, game on. And because of his loyalty, no contract, just a handshake. I've been with Nike ever since. I've never worn another shoe. But when I got to New York, I sensed things were different. The impact, all the opportunities that came, when did you feel that things were different and that whatever brand you went with actually had a ripple effect, not only domestically, but around the world?

20:28Serena Williams:Yeah, I think things got really different. I do remember, actually, now that you mentioned it, I actually forgot about the Seattle Mariners. Yeah, there you go. She's a baseball expert. It happened right here. Yeah. But I definitely remember you more in New York and how that whole world kind of exploded after that. but for me I feel like everything changed after that catsuit and not because of the catsuit I think it was me winning the French Open, Wimbledon and the US Open 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 many great tennis players there was Lindsey Davenport, there was Martina Hingis there was Venus Williams, there was Monica Seles and to dominate at that time with Everyone that was so great was just unheard of.

21:22Serena Williams:And so I think winning that U.S. Open just solidified everything and the outfit. And it was like, well, this kid is amazing. How do I change that? How do I say, OK, tennis is great, but how do I extend that and how do I expand that outside of tennis? Just understanding that pop culture and then get invited to different things. that I would be like, oh, wow, I'm at the Laureus Awards, or I'm here, and I'm actually winning these awards. And, you know, except for the one that I lost, I'm still bitter. I'm not competitive at all. The winning and losing thing is definitely not. Doesn't play with me at all.

22:02And so how do you take advantage of that? Like, what's the process by which, I mean, you've been with Jill for a long time, Jill Smollard. Are the conversations different? Are your ambitions growing? Like, how do you activate that moment where you are blowing up even more?

22:17Serena Williams: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. Maybe I would have had an extra deal or two, but it was really about leaning in into having a woman on my team and owning that. We got ours when the time was due, when the time was ready, but it was some times where we had to fight a little bit extra. It's really just about really empowering not only yourself, but people around you and your team as well. Jill works at WME, amazing agent there. I don't even like that word, actually, but I don't know.

22:58Serena Williams:I haven't been able to find a different word for that. She's like your partner. Exactly, like a partner. And how long have you guys been? Oh, since 2000. That's incredible. Yeah, it's been an incredibly long time. But it really was important to be able to expand and really start to think about what other 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.

23:34Serena Williams: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, and I would always see the mic. I want to be like, mic commercials. And I was like, I want that. And so I would always, we would always come together and say, what are some things that you want to do in a corporate, if it was corporate, what corporate companies you want to be with? And does that resonate with you? I mean, Because I'm sitting between these two very deliberate business people who have caught into this from an early.

24:08I 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, Gatorade is another one because I believe I was I won the Gatorade Player of the Year in high school. And I was like, oh, my God, that's so cool. That's the first big award that I won nationally. And of course, I want to be like my campaign was huge. It still is to this day. But for me, it was Nike. Nike to me was the ultimate North Star because Michael Jordan wore it, right? And we all want to be like those. I looked up to Michael and Magic and Bird. Everyone looked up to Michael.

24:39Serena Williams: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 aplomb that he has walking around is just second to none. Tennis-wise, I was actually inspired by Monica Settlers. I just liked her. I thought she was really cool. And I liked how she grunt. I do have a question. Was there a call where Jill called you and she said, all right, Serena, we got this company, and this is what they're willing to pay you. And you said, what? They're willing to pay me that much? I've had moments like that, but I'm wondering if you ever had a moment like that.

25:21Serena Williams:Yes, I've definitely had that. And I'm like, let's start at yes. But let's not seem desperate. Let's wait 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. But as you've alluded to, Nike does something altogether different. 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.

26:03Serena Williams: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 the best, then you have to wear Nike. That was seared in my mind. I wanted to be the best. And I think the best, they had the best stuff. They had the best marketing. They had an opportunity to put you, as we talked briefly, globally. And because tennis is not just in the United States, it's Australia, it's England, it's Italy, it's China.

26:39Serena Williams:It's literally everywhere on the globe. And I can think of just a handful of companies that can reach that far. And so for me, I wanted to reach that far and I wanted to be with a company that could amplify that. And I'm not necessarily amplifying them. I wanted them to amplify me. You talked about this moment in tennis that I want to dwell on for a second, because you're right. There are a lot of great players, but you very quickly just overcome all of them. You did something marked 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?

27:21Serena Williams:No, it was very apparent because you would see matches if I wasn't at a tournament or Venus wasn't at a tournament. The attendance was just different. And years that I was injured, oh god or um years that stay professional serena don't say that years that i was injured or years that you know i didn't play you could just see the difference of you know people that are were attending the matches or viewers the u.s open is my favorite tennis tournament it is the most electric setting and then it's like the wattage is turned up when you walk out. That's just, again, that's factual. I have to say you feel that.

28:06Serena Williams:And I took on a lot of that pressure as the years continued after 10 years, you know, I would feel that pressure of like, okay, it's, is Serena going to be in New York? And, you know, it's, it was, it was like a, not the, not the Serena open, but it was still like a lot of attention on, 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 Serena effect on Serena? You know, like that pressure that 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.

28:48Serena Williams:I don't think that I try to always remain humble. I don't, I didn't go in the tournament thinking that the U.S. 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 amplified. And it's not easy, but you do walk in with your chest a little farther out and your head a little higher because also you are a target. You know, everyone at the end of the day isn't really happy that you're on the front page of all these papers.

29:25Serena Williams: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 when you lose, losing is way bigger news than winning. Like if I want a match, it's almost last page. And yeah, but if I lose, it's like front and center. So you don't want that story. And so having a lot of that pressure is definitely not fun, But it's also a privilege, you know, and I think it's I would definitely prefer that pressure than not. That makes sense. Yeah. Pressure is a privilege. It's right there, right when you walk out. Wow. It is your New York is your favorite.

30:05Serena Williams:Wow. But Jace, I want to say it's a business because I was on a call with Serena early on and I was like, wow, I wasn't expecting that. And not because I had a judgment. Hey, wait a minute. No, 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. Yeah. Too deep in the weeds, we decided, right? It was too much. But where does that come from?

30:44Is it from your playing days, attention to detail?

30:47Serena Williams:I feel like, yeah, I'm super attention to detail. I feel like I've always excelled at education and I love learning. And so, yeah. So for me, when it comes to my business, and like I said, I think we decided I was too much in the weeds. And like literally what he's talking about, like being on calls with founders 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, we have calls every six weeks. I own that company. So not own the company, but I'm the representative for the company for my firm, SV Cernad Ventures.

31:25Serena Williams:And so I'm like literally on the calls. I'm literally helping them understand how they fundraise. I'm looking at their decks. And so it's a lot. So I just like, OK, that's too much. I can't go on like this. But I truly love investing. And that's one thing that I kind of fell in love with from tennis. I would see these sponsors because tennis is all sponsor based. And I would see like some of these sponsors come up. But I'm like, well, I have some little cash. Like, how did I not invest in Facebook? How did I invest in Airbnb or how did I miss Google or like, you know, all these companies? I don't know if you ever thought of that, but I'm like.

32:01Serena Williams: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 needs. I've got to win the US Open this year. I've got to pay these 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 investing, understand all this stuff a little bit more.

32:52Serena Williams:And that's kind of how it all started. Unfortunately, to your point about the Bay Area and underrepresentation, still there. What is it? Two percent of VC funding less goes to women, you know, even fewer when you when you start to go to other categories 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. Yes, yes. We're literally here for your story. So I started investing and then I somehow got into early stage investing. I didn't realize that it was called early stage. I just liked companies that were starting and then I liked growing them.

33:34Serena Williams: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 fell in love with what they were doing. And I was like, I want to be a part of this. And so it was just finding several different companies like that. Then Masterclass obviously became Masterclass. And one day I was at a conference at JP Morgan and Jamie Dimon was on stage and he was talking to this woman named Karen Seidman Becker, but she's on stage and she's talking about women and VC and how women get less than 2 % of all VC money.

34:15Serena Williams:And I'm thinking, she misspoke. That's so embarrassing. Like I'm embarrassed for her. 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 set the number wrong, but something about 2%, less than 2%. And she was like, you know, Karen. So she's like the woman I dream of being. And she's just like, tells me everything. And she just gives me all this amazing information in the span of 10 minutes.

34:53Serena Williams:And I'm like, I didn't know. And so that's how Sooner Adventures happened from that moment forward. I was like, I need to start an investment 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. I ended up getting about 16 unicorns in my portfolio. So that way I would have a good track record because I knew it wouldn't be probably easy for us to raise a fund first go around. Yeah. Until you get to know me and you get to know the story and you get to know all the investments that I had done.

35:29Serena Williams:And that's what happened.

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36:11So 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. How did that make you feel when you went to LPs, potential LPs to raise capital?

36:39Serena Williams:It's a competition. I loved it. It's what I, it gave me energy. It gives me life in telling my story. And also it 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 2 % 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 going to have to take something out on my house. I'm going to have to go to the bank. Like it's not, I'm not going to be, I'm just going to not be able to get VC money, but we're changing that. And we don't only invest in women.

37:15Serena Williams:We don't only invest in people of color, but we're putting that on a platform. Our portfolio right now, as it stands is 68 % women 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 hear your story of your 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 story, if they pass, they pass, but at least you get them thinking, you get them hearing, And maybe they'll invest in another fund that is doing the same thing.

37:51Serena Williams:Maybe that has been around a little bit longer with the track record, a little bit longer. But they'll come around to us at some point. And that's kind of how I feel. But I love talking to LPs and just getting that story told on a platform that a lot of people don't have. And so that is, it's super amazing for us. 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.

38:30Serena Williams: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 I'm not going to change. I am taking a step back. I'm taking your advice. Like, oh, my goodness, already done. But the impact will always be there and the impact will continue to be there. And I look forward to that. 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 Alexis too, about, you know, these two entities, these two business entities sort of coming together.

39:14And 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?

39:25Serena Williams: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 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.

40:08Serena Williams: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. Oh, you 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 had been in Europe for a few weeks at that point. And then when you hear an American accent when you haven't heard it for a few weeks, it's like refreshing. And so all week at this particular hotel we were staying at, there was these American 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.

40:44Serena Williams:I'm so focused when I play a match. Like I literally would never leave the room. I would watch film all day and I would be in my room and it was a night match. And night matches are extremely stressful for me mentally because I'm having to be in the room from like until 6 p.m. or 5 p.m. So I'm like, I don't want to be in the room till 5 p.m. today by chance. I was like, I just can't do this today. I just can't. So I left to go downstairs at breakfast. Now, this is crazy. Like, come on. I mean, I literally would even eat breakfast in my room. I would never be seen. I was a ghost. So I went to have breakfast.

41:16Serena Williams:Woo! 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 till 11 because I was just fighting with myself. I was like, 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 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 another side of the pool, there's chairs. And so we're the only people.

41:46Serena Williams:It's me, Jill, and my assistant at the time. And he was Australian. That's going to come back too. So we sit down, the only people there, and we order our breakfast and we're just talking and laughing. This guy walks in with a computer and he sits down right next to us at the table right next to us. And I'm like, so upset. I'm like, do you see how big this area is? Are you kidding me? Like, do I look, does it look like we want people next to us? Like, it's huge. And I'm like, oh, my goodness. So my assistant at the time, his name was Zane. He's like, hello, mate. There's an awful accent. He's like, Aussie accent is the worst.

42:27Serena Williams: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 is it really a rat because i'm from brooklyn and i'm not afraid of rats and i was like oh you're from brooklyn so that's how we started talking and then so he said i was like what are you here for and he's like oh i'm here for the conference i was like oh cool who are you here to see and he's like i'm not seeing anybody i'm speaking i'm you know i'm like okay this guy has excuse me and anyway we see you start talking about he did reddit and he started reddit and then of course i hadn't heard of it but i you know now you get to know me i'm like i don't hear of anything right right right but what's interesting about this like jace i've been in a lot of calls and zooms with serena and a lot of calls with alexis and by the way they're both so different but they complement each other so well and they'll never mention they're they're each other's partners they keep it so professional in their lane yeah but then when they come together they're We keep it very church and state.

43:30Yeah.

43:30Serena Williams:Yeah. So what have you learned from him as an investor? We keep it very church and state. Yeah. 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. He's probably already invested in companies way before that sector is even popular, which is honestly incredible.

44:03I will say one of my favorite stories, because, you know, we follow sports very closely, was your influence on the Angel City investment, which as at least as it's been told or as he's told it, Olympia was, you know, getting into playing soccer. So this is a false story. Oh, it is? Yeah, but let's correct it. Yes, let's correct it. Okay, okay.

44:23Serena Williams:I'm not a pro soccer. 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 because obviously let's amplify tennis. Right. But that's that's the real story. But the part of the story that I love is that and you tell us whether this is true or not, is that the baseline should be you need to do something for equal pay in sports. Is that right? Well, I 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.

44:58Serena Williams: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 actually watch soccer and I love women's soccer. I watch women's soccer. and the fact that so many people watch women's soccer and then they're getting paid it's like what they're getting paid is 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 i was like no let's do something for tennis because the work but i did win because olympia does not like soccer anymore oh is that right well for now she changed her mind a lot she does like tennis a little bit more now so i'm like Yes.

45:43Serena Williams:Yeah. Listen, I think you can have some good influence there. So Serena, you're 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 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 today. So Jay, so many times I get calls from founders and they're saying Serena Ventures is in.

46:19And I call Serena and I'm like, we're not quite in yet. Guessing people like to wave that around. Exactly. 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?

46:38Serena Williams: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 an idea of what these investments are like. So it's really just about hard work. It's no way around it. You can't go around it. You have to go right through it.

47:15Serena Williams:And then everything will fall into place. Love that. This has been great. We could talk to you all day. And have fun. And have fun. Are you having fun? I am. I am. 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 trying to tell you guys something. Gratitude is very powerful. It is. Thank you.

47:52This has been awesome. Awesome. Thank you. Thanks for having me.

48:03The Deal is a production from Bloomberg Podcasts and Bloomberg Originals. The Deal is hosted by Alex Rodriguez and Jason Kelly. Our producers are Victor Reveas and Lizzie Phillip. Our story editor is Siddhartha Mahanta. Our assistant producer is Stacey Wong. Blake Maples is our sound engineer. Rubab Shakir is our creative director. 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 Comiskey, Brendan Newnham, Kelly Laferriere, Ashley Honig, Trey Shallowhorn, Kyle Kramer, and Andrew Barden.

48:49additional support from rachel scarmazino elena susangeles vanessa perdomo and anna mazarakis david dominguez is our director of photography our camera operators are sage passetti and angela reyes lata our gaffer is pfeiffer higgins and our grip is courtney poyser katia vannoy is our video editor you can also watch the deal on bloomberg originals youtube and bloomberg television Thanks for listening.

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