Serena Williams on winning in business

Introduction to Creative Planning

0:00The very best founders I know are brilliant at building systems. They connect teams, they remove bottlenecks, and they eliminate single points of failure. And yet, when it comes to their own wealth, most are running a disconnected stack. A tax accountant here and a state attorney there, a wealth manager who doesn't talk to either one of them. Creative planning was built to fix exactly that. One integrated team of tax professionals, estate planners, investment specialists, all coordinated by a dedicated wealth manager who sees your full financial picture and keeps every piece working together.

0:39Proactive tax efficiency, estate strategy, investments all under one roof. Creative planning, where wealth works together. Learn more at creativeplanning.com slash mastersofscale.

Masters of Scale Summit

0:52Hey folks, Jeff Berman here. I am thrilled to share some of the new names who will be joining us at this year's Masters of Scale Summit. This may be our biggest stage yet. Reed Hastings, Meredith Whitaker, Van Jones, Amjad Massad, and more will be there with us October 20th through 22nd in San Francisco. If you're building something great or you want to build something great, we want you there with us too. Join us at mastersofscale.com slash apply 26.

1:25That's mastersofscale.com slash apply 26.

Hard Work and Success

1:30The main thing that it takes to succeed over time is just the fact that you can't underestimate the power of hard work. A lot of people think, oh, this company, boom, they're now billions and billions of dollars and it happened overnight. And that may have been the case in very few stories, but there's so many other stories where it didn't happen overnight. You have to work hard and you have to put in the time every single day. Tough days, easy days, you still have to show up.

Interview with Serena Williams

2:03That's Serena Williams, global icon, tennis champion, and a rising force in the world of venture investing. I sat down with Serena at the Wreck-It Catalyst event in Palm Beach, Florida, to talk about what it takes to win as an entrepreneur in today's competitive marketplace and how she's trying to make a difference off the court. We talked about her work with Nike and Rowe, the rebranding of her business as Starfire Ventures, and how she balances work and family, plus what's motivating what she calls her sporadic return to tennis.

2:36It's an engaging back and forth with a few firm volleys and some unexpected slices along the way. So let's get to it. I'm Bob Safian, and this is Rapid Response. I'm Bob Safian. I'm here with Serena Williams. Serena, great to be able to chat with you today. It's so good to chat with you, Bob. We first met long ago when I was the editor of Fast Company. You spoke at an event alongside then Nike CEO Mark Parker.

3:08And I remember walking backstage with you, and you had these incredible heels on. You were already plenty taller than me without the heels, but you had these incredible heels. And I kept thinking, like, that's got to be risky. That's got to be dangerous. Like, I'm not a professional athlete. I like to take the risk. That's why I got into BC. I love risk. You just owned it. You're known for your sense of culture and fashion, and also, of course, is a tremendous athlete. Fewer people know about Serena Ventures, your business and investing arm.

3:40We're now Starfire Ventures. Starfire Ventures. Yeah, so we've just rebranded ourselves. And now, you know what? I felt like Serena Ventures is great, but I wanted it to be bigger than me. And, you know, there's so many amazing people on the team, and there's so much that we do. And I felt like when you have a name to something, it can limit, you know, what you do. And I wanted to live on. You know, I want this to be something that people look at years and years from now and just say that is— You don't think the name Serena's going to live on?

4:10Surely it will. In a different way. You know what? It's going to live on in a different way. I think it just gives us some freedom to do so much more. And we kept the SV, so it's still SV, because we also internally always say SV. So Starfire has—I mean, you've backed something like 16— Yeah, you got it right. —unicorns. So do you have an overarching philosophy as an investor, or is it more sort of intuitive, instinctive? Oh, it's a little bit of both, but it's absolutely, I would say, 90% of philosophy.

4:46And then we do need some instinct, right? I do a lot on instinct, but I think my partner is definitely more, let's follow things to the T, which is great. So we make a really good team in that way. When you and I were on stage with Mark Parker, you quipped that one day you would be the CEO of Nike.

5:07Did I say that? You did. That's so crazy. You did. So operating a big brand is no longer your aspiration? You like being an investor more? I wouldn't write that off. I wouldn't write that off.

5:22I wouldn't write that off, but I could not live in Portland, so I think I may have spoken too soon.

5:30Yeah, that's— The weather there is just not up to your southern Florida. I need sun. I need—yes. Yes. And I know. But one key word that you said was quip, so. It was. I really wasn't serious about that. Investing, you feel like, is that more sort of in keeping with your spirit, with your goals, than being an operator? I've loved that for years. Oh, my gosh. I think my first investment was like 14, 15 years ago. Now we're institutionalized with institutionalized investors on our cap table.

6:04And it's a lot of work, but it's also rewarding when you see good results. So you—today we're at the Reckitts Catalyst program in Florida. You're the inaugural entrepreneur in residence. Yes. Mentoring a group of founders who are here. You've said being a mentor helps you as much as it helps them. Are there things you've learned in the time down here? What I do every day in VC, we don't necessarily see a lot of the companies and a lot of founders like this that are solving so many problems for underrepresented people.

6:42And it is—it's so feel-good, you know. And every now and then you'll get a company in the portfolio, like one in our portfolio is Isuzu, that does feel good, does do good, and is still a unicorn. And like, those are amazing, but realistically, those aren't—you don't see those every single day. We want to win. We want to make money for our LPs. But at the same time, it's so good to be a part of something like Reckitt Catalyst. Just so exciting to be a part of a bigger story and helping people.

7:17You mentioned that Reckitt's got an emphasis on underrepresented founders. At SV, 70% or something of your portfolio is women or people of color as the founders. How much of that is about, like, financial calculation, that there's a particular opportunity because those communities aren't being seen? And how much of it is sort of a broader imperative for you? That's a broader imperative. We see different companies that most people don't get to see because they don't open the doors.

7:48So our team and the way we—the way I've hired our team, a lot of more women do feel comfortable coming to us. And by the way, a lot of those companies are doing very well, you know, right now. And they wouldn't have the opportunity to do well if we didn't—we weren't on their cap table. And so for us, it's not—we invest in everyone. We invest in people that look like you. We invest in people that look like me. It's just that we do see a lot of women and a lot of underrepresented founders because they have—they know that we'll hear their story.

8:26And we don't invest in them all by no means. We're only investing in winners. If you're—we don't feel the company's not going to return our fund, we're not going to invest in them. And that's just how we look at it. This is not philanthropy. This is— No, we don't. This isn't philanthropy. But women aren't doing business on philanthropy. And people of color, we're not doing business. We're doing business to make money. And it's sad, but that's—some people don't understand that. It sounds like there's opportunity there because other investors maybe aren't opening—aren't open to these kinds of founders.

9:02It's not that they're not open to that. I wouldn't necessarily put another investor down. They just subconsciously don't see it. Or they just subconsciously wipe it out. They're just not thinking about it. But we're thinking about everything. We're thinking about the next billion-dollar company, the next trillion-dollar company, and how to be on those cap tables as well. You've had some tough moments yourself as an entrepreneur. S by Serena isn't around anymore. Win Beauty, which you launched with Alta, sort of didn't get traction.

9:35How do you advise other entrepreneurs about the trouble spots? I mean, you certainly have always had to overcome trouble spots in your tennis. How do you advise them about that? S by is a choice. And Win, I made the decision to pause because not all money is good money. And so our investor, great person, by all means, wonderful individual. But a lot of the things that I said as a VC investor wasn't taken.

10:05And everything that I said would happen, happened. And I was like, okay, this is not what I want. I'm going to take this off the market for now and pause. But me, I think when something doesn't work out for you, you are able to sit at places like Wreck-It Catalyst and give great advice to people and let them know that. Really get to know who you're putting on your cap table. You know, you can't be an entrepreneur or a business person. Like, nobody wins all the time, right? I mean, that is the reality of it.

10:36Yeah, yeah. Right? But you always learn from that. And I always say, I don't even like the word failure because I don't feel that anything is a failure as long as you keep trying. And I guess you also have to, I don't know if this is the right term, but like you sort of have to expect that you're going to fail sometimes. Like, you don't want to be going in there. I don't know if that's the right term, but I understand what you're saying, right? It's like, it's not expecting to fail, but it's expecting challenges maybe, expect there to be a lot of tough challenges. And not being stopped by them when it happens.

11:08Yes, and not being stopped by them and expecting. If your knee hurts, you know, sometimes you can't do what you want to do, but that doesn't mean you're never going to do it. You can't do it. And you're never going to do it again. You know what I mean? I don't know what I'm asking. I'm not sure what that question is. I'm not sure what in the world we're talking about either. No, I think, yeah. Um, so this, this record's catalyst, it's focused on founders in the health and wellness space. And hygiene space as well, yes. Yeah, I mean, your, your portfolio has included several health and wellness firms, if I have this right, ritual, factor, will perform.

11:43I know you're a, you've been a spokesperson for Ro, whose CEO, Zach Ritano, has been a guest on the show. And what kind of role do you see for yourself in, in the health space overall? I mean, why, why, why is it the focus area for you? Yeah, I mean, we all need it. And, um, I think that if there's one thing everyone needs is health. Um, also in our current portfolio, we have, uh, Teal Health, which is really specializing in cervical cancer testing at home, which is very uncomfortable when you go to the doctor to do that.

12:13But now you can do it at home. And we're realizing that a lot of women just don't do it because of the circumstances. Midi, Midi Health. Oh, sure. Yes. Oh my goodness. Yes. Yes. Uh, another unicorn. In particular with women's health, I think a lot of that piece of the pie has been left on the, on the ground. And that's 50% of the population. So that's a huge opportunity. Just if you want to think of it in a monetary value, it's huge. But in addition to that, also just helping people is huge and helping women that has traditionally been forgotten.

12:48Me being a woman as well, it's like, obviously I want my health and wellness too. I have two daughters. I want them to have the optimum health and wellness that they can have as well. Um, and how do we, how do we, you know, get there? Um, I, I, I mentioned your, your work with Roe. Did you have any second thoughts about being a face for GLP-1s? Um, not at all. Not at all. I feel like, and the more we do research on GLP-1s and the more people understand it's, I always said it's not, I mean, it is, does help you lose weight, but it is so much more than that, you know?

13:28And when we, when I first started Roe, there was a lot of things that I couldn't say. Like, oh, I can't say that it helps with, you know, other things as well, because it was just like the testing still wasn't out yet. But I'm like, my blood tests are my, my, so are so much better. My heart, like, I didn't even realize that I had an, I could have been a subject for heart disease. But once I started GLP-1, like, my test shows that I'm no longer a candidate for that. And, uh, diabetes and just so many different things. And also inflammation, like it helps with, with that.

14:01I mean, it's just, it's helping in so many different ways that I just felt like, um, and even at the time I didn't know some of that stuff. And some more of the controversial things that I won't say that it helps with, but those studies are coming out soon that it's helping with those things too. Yeah, no, it's, it's like a miracle in so many ways. And for a lot of people. It is. And for a lot of people. And it's just, yeah. So I'm a, I'm a big believer in that. I've known Zach as well for many years. My husband did his round many years ago before they became Roe.

14:33They were actually a different company at the time and he invested in them. He invested in Zach. So I met him eons ago. And so we always, Zach always wanted to work with me and I always wanted to work with Zach because I loved his origin story about how he started Roe. And I remember sitting in our old office and thinking, this is amazing, man. Like one day the stars will align and it happened to align with GLP ones. And so we have a long history there. You mentioned that your, your husband initially connected to you, Alexis Ohanian, who co-founded Reddit.

15:03He's also an early stage investor in 776. And he helped, helped to found initialized capital. How much do you two talk about investing? We don't talk a lot about investing. He is, um, we'd like to, as he says, we keep a church and state at home. You know, we, he's so busy. A lot of people, he, he works probably 20 hours a day, maybe more. Um, so he's just a workaholic, which is great.

15:34And so I was curious, I like to leave our other time for just other things. Yeah. I was curious because I, I, I did a story once with, uh, with, uh, Mark Zuckerberg and his wife Priscilla. And they, they would have like a, a weekly date basically where they would talk business. Oh, nice. Yeah. I don't know whether that's nice or not, but it was, it was their way of sort of segregating it. Yeah. In other words, so that's the time where they talk business. Another time they can just be themselves. They can be themselves. I like that. I never, I never knew that.

16:04I'm glad I could share something with Serena that she might find helpful. Her life is so jam packed. It's daunting for even an outsider to grasp it. So how does she divide her time between work, family, and tennis? And does she have any advice about the future of the women's sports business? We'll talk about that and more after the break. Stay with us.

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Brand Endorsements and Women's Sports

18:23Before the break, Serena Williams talked about her investing efforts at Starfire Ventures and what she gets out of being an entrepreneur in residence for Record Catalyst. Now, she talks about how she chooses brand endorsements, her ownership stakes in women's sports teams, and the boundaries she embraces in juggling the demands of her personal and professional life. Plus, why she's returned to tennis on what she calls a sporadic basis. Let's jump back in. Your Nike relationship makes me think about all the different brands that you've worked with

18:57over the years. To what extent was that a training ground for you as an investor? Not just Nike specifically, but overall, sort of trying to decide which brands to work with. Well, Nike was always on my list.

19:13I remember I even wore Nike before I was signed with them because I was trying to hint, hint.

19:20You know, I definitely wanted to be with them. And now I'm with them in a different way, in a bigger way. When you're deciding for a brand that you're going to do work with, do you research them the way you would research an investment? Nowadays, absolutely. And with the Nike days, I didn't. It was just something that was iconic. It was Jordan. It was just something you wanted to be with. And they were really elite. And so I think a lot of athletes at the time felt that way.

19:51But now to answer your question, yes, before I work with anyone, I'm doing so much research. My whole team is doing research about the brand, how it aligns with me. And is it authentic? Do I use it? I always like to do things that are authentic to me. Because otherwise, I just feel like it's just not going to be real. And I don't like that. You've also invested in professional sports, women's professional sports, particularly helping to launch LA's Angel City and the NWSL. You're now doing the same for the WNBA's Toronto Tempo.

20:25You helped redefine women's tennis as a business. Does it surprise you that it's taking so long to get to parity in some of these other sports? Well, you know, I was on a panel the other day and we talked about how usually it's like a 30 years. Women's basketball, we're literally at that 30-year mark from when the WNBA started. And you're really now we're seeing the fruitage of that. And I thought that was a really interesting point because I never thought of it like that. But then I started thinking about tennis and how we had Billie Jean King.

20:55And then 30 years later, it became tennis. And so I was like, oh, you know, that's interesting. And so is there science and is there numbers to back that? I don't know. I'm just telling you. I was on a panel and that's what was said. And I found it interesting. I can imagine that some of these teams, I mean, you were so instrumental in kind of pushing that opportunity open in tennis, you know, to what extent they're coming to you for advice about how to make that leap now.

21:25Yeah, no. Although you said it, I didn't. They should. I feel like there's a lot of things that I can advise. Is it right? Who knows? But usually what I say happens. What would you tell them?

21:43I'm not going to get into that because I would like for them to come to me for advice or I can go to them, give them some advice. Fair enough. Fair enough. So you've got your investing work, SV, and your brand deals, and you've got your husband, and you've got your daughters.

22:04And amid all that, you're returning to professional tennis. Very, very sporadically. Very sporadically. Maybe I'm here. Maybe I'm there. Who knows? Very sporadically. How do you decide how to spend your time?

22:22I'm a very organized person. I'm an A-type personality. Most of my time is with Starfire, Serena Ventures. Um, that's where I spend 90% of my time. Well, outside of my kids, like when I'm not with my children as a mom, I would say most of my time is spent with Ventures, and that's just how. Are you really the school mom for Olympia School? I was when she was in second grade, and I can't believe that was already almost a year and a half ago. I loved being the school mom. That was great. Um, I loved it.

22:53They grow so fast. I still do try to volunteer. In fact, this year I want to volunteer for the dance. Because I do have a dance background, believe it or not, and I would love to offer some help. I think I may have seen some videos of you dancing. I may have seen them. Just because I love that part of the world. Um, but yeah, so, but now with my partner at SV, I have a lot more time to do other things, like be more with my kids and to go back sporadically, every blue moon, you never know,

23:24um, antennas, which has been really fun. Um, and, um, so it's, it's good to have those opportunities again, because she's amazing. She's, she's like, she's, uh, she's the Serena Williams of BC. So I love that she's on our team. And as a, Beth, Beth Frere, so. As a, a type A sort of organized person, do you have a, do you have a structure you use? Like I do, you know, I have a lot, I realize now I have a lot of, um, what's the word I'm looking for, boundaries, time boundaries. And even in training, like when I went back for Wimbledon, I was like, listen, I'm willing

23:56to put this in an hour here, two hours there. And that's that. And what happens, happens. This is what I'm willing to do. I'm not going back out there to win Grand Slams. I have a full-time job. Um, but this is what I'm willing to do. And this is how I'm willing to show up. And, um, it, it would have worked if my knee didn't swell. Um, but I had fun and, um, yeah, it was putting boundaries because I'm a mom now. And I think more than anything, my kids need me.

24:28Well, and that, that, that discipline though is, I mean, I imagine it's another. I'm scheduled out. Like I'm like very every I'm scheduled out to the hour. Yeah. I mean, I was thinking of the, the, the Reckitt's, uh, folks who you're, who you're, uh, mentoring sort of teaching them to be disciplined too. I mean, discipline has always been part of your, your life. Yeah, discipline and boundaries, I think. Like, listen, like I have boundaries. This is the time I need to put into my VC. This is the time I need to put in my kids. And those take a lot more than other things.

24:59So you're setting those priorities. I talked on the podcast recently with, uh, Maria Sharapova. And she talked about how the competitiveness of business and sort of being in the boardroom, it kind of taps some of the fire of playing. Um, but then she also said that nothing matches the adrenaline of, of being on the court. And, and I guess I, I wondered whether like, is that part of the reason why you're, you want to compete again at, you know, with everything else going on in your life?

25:30Or is it, is it, is it, is it for you? Is it for your daughters? Like what, what's the. I would say it's more for my kids more than anything. Um. To show them that you can. Mostly even for Olympia because she's eight and the other one's only two. Um, Adira is only two. Um, but it's nice for them both get, but Adira is like, she's incredibly wickedly smart. So she even says, I'm going to play tennis like mama, even before I played at Wimbledon. So she gets it.

26:01Um, but it's nice for them to have that opportunity. And I could still play. I retired because I wanted to have children, many children. Um, then I had Adira and I was like, um, so we had a lot of fun. Um, but it was nice. Maybe two as many. Two as many. Right. And so it was really, it was just, I still had a lot in my, me as you could see. And it was just more of a different decision. So, yeah. Yeah. Yeah. Um, well for, for the listeners to this show, the, the business people, the entrepreneurs,

26:35the investors, do you have any advice for them on how to think about their journey, their, their goals and sort of what it takes to succeed over, over time? You know, what's worthwhile, what you, what you need to do to stay grounded. I think the main thing that it takes to succeed over time is just the fact that you can't underestimate the power of hard work. A lot of people think, oh, this company, boom, they're now billions and billions of dollars and it happened overnight. And that may have been the case in very few stories, but there's so many other stories

27:10where it didn't happen overnight and people work, you have to work hard and you have to put in the time every single day is very redundant. And, um, you know, you just have to show up every day, um, whether it's tough, tough days, easy days, you still have to show up and you can't underestimate the power of hard work.

Conclusion and Final Thoughts

27:30Well, I want to say that I appreciate you showing up for this after what I know has been a very busy day and thanks for doing it. Thank you. It is a little surreal to spend time with Serena. She's very human. And at the same time, she's, you know, Serena. Her ambition is high in business as in tennis, but she's also earned perspective on both fronts. She's using her status to make a positive impact on the world through women's health, women's sports, through mentorship.

28:00And her commitment to her family is real. I saw her check in on her kids before and after our taping. What strikes me most is the balancing act she's engaged in and how hard it is to create time to just be herself. She mentioned wanting to volunteer for her daughter's school dance. I hope she can. All of us need to make space for the things that feed our soul and our heart, whether that's dance or tennis or something else. It gives us the strength to carry through the tougher moments and keep up that hard work.

28:32I'm Bob Safian. Thanks for listening.

28:45Rapid Response is a Wait What original. I'm Bob Safian. Our executive producer is Eve Trow. Our senior producer is Alex Morris. And our associate producer is Masha Makutonina. Mixing and mastering by Aaron Bastinelli and Brian Pugh. Our theme music is by Ryan Holiday. Our head of podcasts is Lital Moolad. For more, visit RapidResponseShow.com.