Serena Williams on winning in business

Transcript from https://podmenti.com/t/10ca7a7021da64d6

The 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, state planners, investment specialists, all coordinated by a dedicated wealth manager who sees your full financial picture and keeps every piece working together.
Proactive tax efficiency, state strategy, investments all under one roof.
Creative planning where wealth works together.
Learn more at creative planning dot com slash masters of scale.
Hey 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 Masad, 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 masters of scale dot com slash apply twenty six.
That's mastersofscom slash apply.
Twenty six.
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, 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.
That's Serena Williams, global icon tennis champion, and a rising force in the world of venture investing. I sat down with Serena at the Record 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 Ro, the rebranding of her business as Starfire Ventures, and how she balances work and family.
What's motivating what she calls her sporadic return to tennis.
It'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 Safe and I'm here with uh Serena Williams. Serena, uh great to be able to chat with you today.
It's so good to chat with you, Bob. We first met uh long ago when I was the editor of Fast Company spoke at an event alongside uh then Nike CEO Mark Parker, and I remember um
Walking backstage with you and you had these
Incredible heels on.
Yeah, you were already plenty taller than me without the heels, but you had the incredible heels. And I kept thinking like that's gotta be.
Risky. That's gotta be dangerous. Like I'm not a I'm not a professional athlete. I like to take the risk.
You're known for your sense of of
Culture and fashion and also, of course, is a a tremendous uh athlete. Um fewer people know about uh Serena Ventures. Starfire Ventures. Starfire Ventures. Yeah, so we've just rebranded ourselves and now um 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 want it 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 gonna live on? Surely in a different way. You know what? It's gonna live on in a different way. I think it just gives us some freedom to do so much more. And
We kept the S V so it's still SV, because we also internally always say SV.
So Starfire
Has y I mean you've backed something like sixteen
Yeah. Unicorn. So do do you have a uh an overarching philosophy as an investor, or is it more
sort of intuitive, instinctive. Oh, I it's a little bit of both, but it's absolutely on I would say 90% of uh uh
philosophy and then we do do need some instinct, right?
I do a lot on Instinct, but I think my um
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 Mar Parker, you quipped that one day you would be the CEO of Nike. Um Did I say that? You did. So crazy. You did. So uh operating a brand is is no longer your your aspiration. You like being an investor more. I wouldn't write that off.
Um
I wouldn't write that off, but
I I could not live in Portland, so I think I may have spoken to some. Um yeah, that's the weather there's not to your s southern Florida. Sun I mean yes. Yes. And I yeah, no.
But you one key word that you said was quip, so
Clearly wasn't serious about that.
Investing you feel like is is that
more sort of in keeping with your with your spirit, with your goals than than being an operator.
I've loved that for years and oh my gosh.
I think my first investment was like fourteen, fifteen years ago. Now we're institutionalized with into s institutionalized investors on our cap table. Um
And it's it's
It's a lot of work. Uh but it's also rewarding when you see good results. So y you uh today we're at the Recit's Catalyst program in Florida. You're the inaugural uh entrepreneur in residence. Yes. Um mentor a group of founders.
Who who are here. You've said being a a mentor helps you as much as it helps them. Are there 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 um people. And it is
It's so feel good.
Yeah.
W every now and then you'll get a company in the portfolio, like one in our portfolio is E Suzu that
Does feel good.
Does do good.
And it's still a unicorn. Like those are amazing, but realistically those
Aren't you don't do you don't see those every single day.
We wanna win, we wanna make money for our LPs, but at the same time, it's so good to be a part of something like Record Catalyst just
So exciting to be a part of a bigger story.
And helping people.
You mentioned that Recett's got an emphasis on underrepresented founders.
Seventy percent or something of your portfolio is women or people of color as 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? It's a broader imperative. We
see different companies at most
people don't get to see'cause they don't open the doors.
So our team and the way we we we the way I've hired our team, a lot of more women do feel comfortable come coming to us. And by the way, a lot of those companies are doing very well. Yes, 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 um for us it's
It's not we invest in everyone. We invest in people that look like you. We invest in people who look like me. It's just that we do see a lot of
women and a lot of underrepresented founders.
'Cause they have
they know that we'll hear their story. And we don't invest in them all by no means. We we only investing in winners. If you're we don't feel the company's not gonna return our fund, we're not gonna invest in them. And that's just how we look at it. Um 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 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
There's opportunity there because other
investors maybe aren't opening are aren't open to the to these
To these kinds of founders. It'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, um, and how to be on those cap tables as well.
You've had um some tough moments yourself as an as an entrepreneur S by Serena isn't around anymore. When beauty, which you you launch with all to sort of
Didn't get traction.
How do you advise
uh other entrepreneurs about the trouble spots. I mean you
Certainly I've always had to overcome trouble spots in your tennis. How do you how do you advise him about that?
S spy is a choice, and when I made the decision to pause
Because not all money is good money.
Uhhuh. 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 and everything that I said would happen happened and I was like okay this
is not what I want. I'm gonna take this off the market for now.
Um 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 who who you're putting on your cap table.
You know.
You can't be an entrepreneur or a business person.
Yeah, like nobody wins all the time, right? I mean, it's mini grand songs. Yeah, yeah. Right?
But you always learn from that. And then 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 I don't know whether it's the right term, but like you sort of have to expect that you're gonna fail sometimes. Like
You don't want to be going on. That's the right term. Um, but I understand what you're saying. Yeah right? It's like it's not expecting the fail, but
It's expecting challenges, maybe? Expect there to be a lot of chall tough challenges. And not being stopped by them when it happens. Yes, and not being stopped by them and expecting it. If your knee hurts, you you know, sometimes you can't do what you want to do, but that doesn't mean you're never gonna do it again. You're never gonna do it again. You know what I mean? I don't know what I'm sure what we're talking about.
I'm not sure what in the world they're talking about either, but No, I um so this this records catalyst, it's focused on founders in the health and wellness space. Yeah. I mean your
Your portfolio has included
Several health and wellness firms.
If I have this right ritual factor, we'll perform.
I know you're a you're you've been a spokesperson for Roe, who's CEO, Zach Ratano's 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 what why is it a focus area for you?
Yeah, I mean we all need it.
And um I think that it 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, but 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 helps. Sure. Yes. Oh my goodness, 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 ta on the ground.
And that's fifty percent 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 is traditionally been forgotten.
Me 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. I I I mentioned your your work with Roe.
Mm-hmm. Did you have any s second thoughts about being a face for GLP ones?
Um, not at all. Not at all. I feel like and the more we do research on GLP ones 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, and when we f when I first started Ro, 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 one, 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 g with with that. I 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 that I won't say that it helps with, but those studies are coming out soon that is helping with those things too. Yeah. Yeah, no, it's it's like a miracle in in so many ways. 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 known Zach as well for many years. Um my husband
did his round many years ago before they became Roe. They were actually a different company at the time and he invest 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 um so we have a long history there.
You mentioned that your your husband initially connected you, uh, Alexis Ohanian, who co founded Reddit. He's also an early stage.
investor uh in seven seven six and he f helped helped to found uh initialized capital.
How much do you two talk about investing?
We don't talk a lot about investing. He is um
We liked he as he says, we keep it church and state at home. You know, we he's so busy. A lot of people he
He works probably twenty hours a day, maybe more.
Um
So he's just a workaholic, which is great.
And so I'd like to sac leave our other time for just other things. Yeah, I was curious'cause 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 segregated, yeah. 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.
I'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.
When you've built substantial wealth through your business, it's often tied up in a single equity position.
The upside is real, but so is the risk, and knowing when to act isn't always obvious.
Creative planning works with business owners to build a strategy around concentrated equity.
When to diversify, how to manage tax risk, and how to protect what you've spent years building.
Creative planning where wealth works together.
Lear more at creative plating dot com slash masters of scale.
Humans will never be more intelligent than AI.
There can be two types of companies.
Those are great at AI and those that went out of business because they weren't. How do we build a future?
That is human centered.
I'm Rana El Calyubi.
On my podcast Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone.
Every week, I sit down with the pioneers shaping our future. And we take you behind the scenes of the AI that's transforming our lives.
Find pioneers of AI wherever you tune in.
Hey listeners, Bob here. If you listen to Rapid Response on Masters of Scale, you may be missing half the show.
Because every Friday we release a second rapid response exclusively in the Rapid Response feed. The guests and topics are just as compelling and timely from Ford CEO to NASA's administrator to the lessons from The Devil Wears Prada. It takes about
10 seconds to find, just search rapid response wherever you listen to podcasts and hit follow to make sure you never miss an episode.
I hope to see you there.
Before 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 over the years.
To what extent was that a training ground for you as as an investor? Not just Nike specifically, but but overall sort of
Trying to decide which brands to work with and Well Nike was always on my list. Um
I remember I even wore Nike before I was signed with them because I was trying to hint, hint.
Um
You know, I definitely wanted to be with them. And now I'm with them in a different way, in a bigger in a bigger way. When when you're deciding
Uh for a brand that you're gonna do work with uh 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 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. But now to answer your question, yes, uh 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? Like and I I always like to do things that are authentic to me,'cause otherwise I just feel like
It's just not gonna be real.
Mm-hmm. And I don't like that.
You've also invested in
Uh
Professional sports, women's professional sports uh particularly helping to launch.
LA's Angel City and the NWSL. You're now doing the same for the WMBA's uh Toronto Tempo.
You helped
Redefine
Women's tennis as a business. Does it surprise you that it's taking
so long to get to parity in in some of these other sports.
Well, you know, I was on a panel the other day and we s talked about how it usually is like a thirty years.
women's basketball we're at that we're literally at that thirty year mark from when the WMB started and you're really now we're seeing the fruit 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 Jin King and then thirty years later it became tennis.
And so I was like oh
You know, that that's interesting. And so, um
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 the these teams I mean, you 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
How to make that.
That leap now.
Yeah, um no, although
You said it. I didn't.
They should. I feel like there's a lot.
the things that I can advise.
Mm. Is it right? Who knows, but usually what I say happens. What would you tell them?
Um
I'm not gonna get into that. Um, because I would like for them to come to me for advice or I can go to them.
Fair enough. Fair enough. So you you've got your investing work as
S V and your brand deals and you've got your husband and you've got your your daughters.
And amid all that, you're returning to professional tennis.
Very, very sporadically. Very sporadically. Maybe maybe I'm here, maybe I'm there, who knows? Very sporadically. How do you
Decide.

how to spend your time.
Um
I'm a very organized person. I'm an A type personality. My m most of my time is with Starfire, Serena Adventures.
Um
That's where I spend ninety percent 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 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, though it was great. Um
I loved it. I do I still do try to volunteer. In fact this year I want to volunteer for the dance.
'Cause I do have a dance background, believe it or not, and
I would love to offer
Some help.
I I think I may have seen some videos of you dancing. I think I may have may have seen it. Just because I love that part of the world. Um but yeah, so but now with my partner at S V, 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. Um
Antennas, which has been really fun.
And um so it's it's good to have those opportunities again'cause she's amazing. She's she's like
She's uh she's the Serena Williams of V C. So I love that she's on our team. And Beth Beth Ferrer, 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 Windows, I was like, listen, I'm willing to put this in.
A hour here, two hours there, and that's that.
Uhhuh. 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 I
It would have worked if my knee didn't

Um but I had fun and
Um
Yeah, it was
Putting boundaries'cause I'm a mom now and I think more than anything my kids need me.
Mm well, 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. Mm.
Yeah. I mean but I was thinking of the the the Recitts 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. Discipline and boundaries, I think. Like listen.
Like I have boundary. 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. So you're setting those priorities.
I
Talked on the podcast recently with uh Maria Sharipova 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 wanna compete again at
You know with everything else going on in your life, or is it is it for you? Is it for your
Daughters? Like what what's that? I'm going to say it's more for my kids more than anything. Um To show them that you can mostly even for Olympia'cause she's eight and the other one's only two.
Um
Adira's only two.
Um
But it's nice for them both get'cause it but Adir is like she's incredibly
wickedly smart. So she even says, I'm gonna play tennis like Mama even before I played
at Wimbledon. So she gets it. Um, but it's nice for them to have that opportunity. And I can still play. I retired because I wanted to have children, many children.
Um, then I had a deer and I was like, um So we had a lot of fun. Um but it was Ninety two is 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, the 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, very few stories, but
There's so many other stories where it didn't happen overnight and people work you have to work hard and you have to put in the time every single day. It's 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.

Well, 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, and 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.
I'm Bob Safian.
Thanks for listening.
Rapid response is a wait what original. I'm Bob Safian, our executive producer is Eve Tro.
Our senior producer is Alex Morris, and our associate producer is Masha Makutonina.
Mixing and Mastering by Aaron Bastanelli and Brian Pugh.
Our theme music is by Ryan Holiday.
Our head of podcasts is Letal Malad.
For more, visit rapidresponsshow.com.