CEO Series: Serena Williams, Serena Ventures

SW (clip):

*Kendrick Lamar’s Superbowl performance* 

Man. I did not like that at Wimbledon. Oh, I would have been fire... It was all love. 

Introduction (clip):

“The gold medal goes to Serena Williams and it only took a little over one hour. Serena Williams, winner of the open title, the most in the open era.”

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In September 2022, Serena Williams announced her retirement from professional tennis, concluding a career that included 23 Grand Slam titles and four Olympic gold medals. 

Serena Williams' dominance on the tennis court is undeniable, but her true legacy extends far beyond Grand Slam titles. She is, without question, the most consequential athlete of the 21st century—not just for what she achieved in sport, but for the barriers she shattered off the court.

SW (clip):

I just want to start investing in different things and trying to see, okay, what is 2.0? I love my career, I love my tennis career. But where was the next step for Serena?

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Serena was reported by Forbes to be worth more than $340 million — but here’s where it gets interesting. Only about $95 million of that came from her tennis wins. Serena along with her older sister Venus, broke into a country-club sport where resistance to two Black girls from Compton was baked into its very DNA; AND beyond that, she had successfully built the business of Serena.

SW (clip):

Being a professional athlete is truly a dream come true. And I was lucky enough to do it with my family. My dad was my coach. My sister was my partner. It all went so well that they made a movie about it.

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While much has been written about her, including a beautiful film, King Richard, capturing her journey, meeting her in person at INBOUND last year gave me a deeper perspective on Serena as a brand and business leader. 

And as we celebrate Black Excellence this month, she’s the perfect feature for this month’s Billion Dollar Moves CEO Series, where we explore the strategic moves behind her empire.

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First, a quick refresher: how did this Compton raised Black woman become the GOAT in a historically affluent, overwhelmingly white sport?

Serena Williams was born in Saginaw, Michigan, to Richard Williams and Oracene Price. She grew up with several half-siblings from her parents' previous marriages but shared a unique bond with her only full sibling, Venus Williams.

The story goes that Richard Williams, after watching Virginia Ruzici play tennis, was so inspired that he decided then and there that his two daughters would become professional tennis players. 

Richard Williams (Clip):

I watched a tennis match on TV, and it was giving this young lady $40,000 because she won a tournament. And I figured since I work the 52,000 all year and this girl make $40,000 for day and I knew I was in the wrong business.

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With no prior experience in the sport, he meticulously studied the game, wrote a 78-page plan for their success, and took it upon himself to train them.

From the age of four, Serena and Venus practiced relentlessly on the public courts of Compton, California—many of which were dominated by gangs. Richard believed that exposing them to adversity early on would build the mental and physical toughness they needed to dominate on the court. Through discipline, resilience, and an unshakable belief in their potential, he shaped two of the greatest athletes the world has ever seen. 

Venus Williams (Clip):

We didn't go to school parties and all that stuff. But somehow I don't feel like I've missed out. I mean, there's probably a few things I wanted to go to, but I figured I wasn't going to go, so I didn't ask. And anyway, most of the time I was at practice. 

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When Serena and Venus turned professional at 14 years old, they took the tennis world by storm. Venus blazed the trail, but when Serena arrived, she overwhelmed the courts with her thundering strength and a playing style that overpowered opponents. 

Her explosive serves, blistering groundstrokes, and sheer physical dominance ushered in a new era of women’s tennis—one where power, speed, and mental fortitude became just as critical as finesse. The rest as we know is history.

Clip:

She's amassed 23 Grand Slam singles titles, 16 Grand Slam doubles titles, four Olympic gold medals, 843 match wins, 319 weeks at world number one and over $93 million in prize money. She's the most decorated tennis player and one of the greatest athletes ever to walk the earth.

Key Takeaway #1: Owning Who You Are, Your Trajectory &  Staying The Course

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Even though the Williams sisters revolutionized tennis and brought the sport to a completely new audience, their arrival was hardly met with open arms by the predominantly white and traditional tennis community of the 1990s. Their aggressive playing style—characterized by blistering serves and unrelenting power—was unlike anything women’s tennis had seen before. 

But it wasn’t just their dominance on the court that unsettled the establishment; it was their entire presence. 

From the beaded braids in their hair to their unapologetic confidence, from their electrifying outfits to the raw intensity of their game, Serena and Venus defied every convention. They were loud, they were bold, and they didn’t conform to the unspoken etiquette of the sport. Critics dismissed their style as brash, commentators scrutinized their every move, and the sisters often faced racial undertones in the backlash they received. 

But rather than shrink under the weight of the criticism, they leaned into it—forcing the sport to evolve and proving that greatness could not be confined to tradition.

A competitor once said “You can hear them and it’s just annoying, things flying around in their hair”

Competitor (Clip):

Well, you can hear them and you can. You can see them a little bit. I mean, you know, fortunately, you know, you learn to play the ball, but I'm not going to say it was a total distraction, but it is a little annoying maybe. It's just things flying in the air that you're not supposed to be seeing.

SW (Clip):

No, I shouldn't have to change for any other circumstance. I like my hair.

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Things came to a head in 2001 at Indian Wells, one of the most controversial moments in the Williams sisters' careers. In a highly anticipated semifinal match, Venus Williams withdrew just minutes before she was set to face Serena due to a knee injury. The sudden withdrawal fueled speculation that their father, Richard Williams, was orchestrating match outcomes between his daughters, feeding into the long-standing conspiracy that their matches were "fixed."

When Serena stepped onto the court for the final against Kim Clijsters, she was met with a hostile and venomous crowd. Boos echoed through the stadium, not just at Serena, but also at her father and Venus, who watched from the stands. The atmosphere was toxic—many in the predominantly white audience weren’t just angry about the withdrawal, but about the Williams sisters' growing dominance in the sport. As Richard later recounted, he and Venus even heard racial slurs hurled at them from the stands.

SW(Clip):

I remember the whole stadium was 99% white people, and they were all booing and it was racial slurs used. It was loud too. I was like, this echo, echo was so loud I could feel it in my chest. 

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Despite the hostility, Serena showed incredible mental resilience, battling through the jeers to win the title in three sets. But the scars of that day ran deep. The Williams family boycotted Indian Wells for 14 years, with Serena not returning until 2015, and Venus following suit in 2016.

The 2001 Indian Wells final wasn’t just a moment of controversy—it was a glaring reminder of the resistance the Williams sisters faced as two Black women breaking barriers in a historically exclusive sport. But in true Serena fashion, she let her racquet do the talking, proving once again that no amount of hate could shake her greatness.

SW (Clips):

Don't want to see a woman and someone of color? Great. (Tennis ball hitting; shouting) 

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In 2015, she again played at Indian Wells, Serena Williams helped raise money for the Equal Justice Initiative, a nonprofit dedicated to racial justice and fighting mass incarceration. Talk about punching back!

One of Serena’s greatest strengths is her authenticity. Whether she’s battling on the court, advocating for equity, or building a business, she remains unapologetically herself.

SW (Clip):

My dad always told me this, you know, he always said, in order for you to learn to get better and to improve, you have to know your history. You have to know your past. You have to know where you're from, or you're not going to be your best self. 

We want to inspire people because like I said, at the end of the day, we work and are always happy and grateful for everything that we had.

I'm still training, so like so many hours a day. But that is what's most important to us, is that, okay, there's no one else is going to be easier. It's not about me and my career. It's just about, you know, for me more what I do off the court. Tennis is like this for me. And life is so much bigger. 

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Serena once said: “You are one person; who you are in business should reflect who you are in life.”

Here’s my takeaway in all of this: Beyond the obvious resilience, it’s clear that Serena is who she is and makes no apologies. She built her career—and her empire—on her own terms, refusing to conform to outdated expectations. She has never hidden her ambition, never softened her message to make others comfortable. That authenticity has made her one of the most trusted and influential voices in sports, business, and beyond.

Key Takeaway #2: Unbreakable Resilience: Rising from Adversity

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By 2002, Serena was at the peak of her powers. She stormed through the tennis world, capturing three consecutive Grand Slam titles—the French Open, Wimbledon, and the U.S. Open—defeating her sister Venus Williams in each final. On July 8, 2002, she ascended to World No. 1 for the first time, dethroning Venus in a moment that felt like a symbolic passing of the torch.

SW (Clip):

Being in Venus Williams’ shadow. You know, my whole life I was fighting for a respect. I always promised myself one day that I wanted to be like her. And you know that I would prove everyone wrong. 

Announcer (Clip):

Well, it seems like forever. She shared everything with her sister, Venus, but now the stage belongs to Serena, the U.S. open champion. 

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At the 2003 Australian Open, Serena once again faced Venus in the final, securing her fourth straight major title and completing what she would later call the "Serena Slam"—holding all four Grand Slam titles simultaneously. A feat accomplished by only a select few in history, this moment solidified Serena as not just a dominant force, but a generational talent rewriting the boundaries of women’s tennis.

But just as she stood at the pinnacle of her career, life dealt her a devastating blow.

SW(Clip):

My oldest sister, Tunde, she always used to tell me. Serena, don't worry. Your day will come and you are going to be bright. And you are going to shine. She was the one that really believed in me. 

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On September 14, 2003, tragedy struck—Serena’s older sister, Yetunde Price, was shot and killed in Compton, California—the very neighborhood where the Williams sisters first honed their craft. Yetunde, a nurse and devoted mother of three, was caught in gang crossfire while sitting in a car with her boyfriend. The loss was more than a family tragedy—it shattered Serena and Venus. Yetunde wasn’t just a sister; she was a confidante, a guiding force, and a steady presence in their lives.

Grieving, physically exhausted, and nursing a lingering knee injury, Serena stepped away from tennis for nearly eight months. She avoided the sport entirely, turning to acting, fashion, and other creative pursuits in an attempt to heal from the trauma.

Her absence was deeply felt. For two years, she had been the sport’s undisputed queen, setting a new standard for power and dominance. Now, tennis moved forward without her— at one point, her ranking falling all the way to 140th in the world.

SW (Clips):

I can't believe I just won three in a row. And everyone's like, oh, you can win four. I'm like, guys, I just won three. That's pretty awesome. For someone my age. So stop putting all this pressure on me. I think it’s bed time…

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But Serena’s story has never been about retreat—it has always been about the comeback. She won Wimbledon 2012 and Olympic gold in London, completing a Career Golden Slam.

By 2013-2015, we saw a winning streak where Serena won 8 major titles in three years, including the 2014–15 Serena Slam, again holding all 4 Grand Slam titles. Her 2015 season was one of the most dominant in history, winning the Australian Open, French Open, and Wimbledon before an emotional loss at the US Open.

Clip:

Oh, can you believe it… Foot foul on the second serve? Gives Clijster two match points. 

Oh Serena Williams was giving it to him… 

She has to be careful.If she gets a warning, it's penalty. Game set match. (crowd booing)

SW (Clip):

So obviously that was my big thing in tennis. Like I never wanted to lose. But unfortunately I think when you do lose you learn some of your biggest lessons. And I kind of every loss that I had, I kind of needed that to actually become Serena Williams or I would have never been this person had I not taken some of those really, really hard falls, and some losses that quite frankly, sucked.

I definitely mope for a little bit. But then I do something about it. When I first started, I used to punish myself, and I would say if I lose, I'm watching the film. And that was very hard, and it was very difficult to watch it go back and to watch the footage of why I lost.

But it also helped me, though, because it was like, A, I never wanted to watch that footage again and B, you have to see why you didn't win. Like with investing, if I do something wrong and I tell my team all the time, like, what if this didn't go well, why didn't it go well? What do we like about it?

What can we learn from this? And so bringing that to this aspect across the board, just like in tennis, I would say, why did I lose and how to not do that again.

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But of course, let's not forget her final battle from 2017 to 2022. In 2017, she won the Australian Open while two months pregnant, a feat unparalleled in sports. Her childbirth, unfortunately, was life threatening due to complications requiring multiple surgeries.

SW (Clip):

It was a tough pregnancy, but, you know, I like that. I talked about it. Not knowing how many people it would affect. And a lot of people could relate. So I was glad that I could do that and continue to do that from now going forward.

Obviously, I think my health is probably pretty important too. So, I'll take it one day at a time and see.

I actually feel like I'm doing better because I used to like, train, train, train. Now I train and then I have a time where I cut it off and I spend the rest of day with her. So it's different. Like I'm more serious because I know I have to stop at a certain time. 

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After a year off, she returned in 2018 and made four Grand Slam finals Wimbledon and US open in 2018 and 2019, but fell short of winning. Though she did win another Grand Slam after childbirth, her presence remained a testament to longevity and resilience. Serena didn't win 23 Grand Slam titles because she avoided hardship. She won because she mastered the art of overcoming it. 

Key Takeway 2 is: So many I know that are the most successful arent the smartest nor the most talented; it is that resilience is their ultimate advantage: they can outwork and outlast anyone in the game they play. And for Serena, she learned from adversity, embraced failure, was willing to take a break and returned with greater strength

Key Takeaway #3: The Business of Serena: From Court to Commerce— You Are Your Biggest Product

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While her dominance in sports cemented her as a global icon, it is Serena’s entrepreneurial vision and investment acumen that has been silently shaping industries and redefining leadership. Recall how only $95 million of her current $340 million net worth comes from her tennis wins? Serena has been meticulously building her second act—curating a portfolio that spans venture capital, beauty, and even sports team ownership.

SW (Clip):

I just want to start investing in different things and trying to see, okay, what is 2.0? I love my career, I love my tennis career. But where was the next step for Serena?

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Serena’s passion for fashion is more than a personal interest—it’s a strategic business move. In 2018, she launched S by Serena, a clothing line designed to empower individuals through accessible, inclusive, and stylish fashion. Her brand reflects her own fearless approach to life: bold, unapologetic, and built for winners.

But she didn’t stop there. In the same year, Serena collaborated with Nike and Off-White, where the late visionary Virgil Abloh crafted a collection that blurred the lines between athleticism and high fashion. The partnership, featured in Vogue, wasn’t just about clothing; it was a cultural moment—one that symbolized the fusion of sport, art, and identity.

SW (clip):

It's an incredibly difficult business. And that's what people say, that fashion is hard. You don't really. It's a really difficult to make money in fashion before the first ten years. Really? Or five years. I love a challenge. And it's not just about fashion. The thing is, with s, it's more about a lifestyle.

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Serena Williams understands that wealth isn’t just earned—it’s built. Her investment mindset has led her to stake a claim in industries where few athletes have dared to go.

• Sports Ownership: In 2009, she and her sister Venus Williams became minority owners of the Miami Dolphins, making history as the first African-American women to hold ownership in an NFL franchise. Their presence in the league was more than symbolic; it was a signal of changing tides in sports leadership.

SW (Clip):

You can't enter anything without having a plan, you know? So, so we started, like I said, we start in fashion, and then we're going to go to beauty.

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Always a step ahead, Williams entered the $500 billion beauty industry with WYN Beauty—a brand dedicated to performance-driven, inclusive cosmetics. In parallel, she launched Will Perform, a wellness brand catering to both recovery and everyday self-care, bridging the gap between elite athletes and everyday consumers.

Her journey from tennis prodigy to business mogul isn’t just inspiring—it’s a masterclass in brand evolution and strategic wealth-building. Like her legendary matches, Williams’ entrepreneurial playbook is defined by precision, resilience, and the undeniable will to win.

SW (Clip):

When you're used to being a champion, you're used to winning. And so that's something that I'm always motivated by is success. And what is 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.

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, if you want to be the best, then you have to wear Nike. And I think that that was seared in my mind. I want it 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. Because tennis is not just in the United States, it's Australia, it's England, it's Italy, it's China. It's literally everywhere on the globe. And 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 to them to amplify me. 

Key Takeaway #4: Investing with Purpose

SW (Clip):

I started investing in different companies and diverse, and women and people of color. Back in 2014. But it wasn't the right time to talk about it. I wanted to make sure my portfolio was really good. So when I came out, I had come out with a bang.

I mean, when I play tennis, I try to go out with a really strong, you know, bang. And so that I felt like I want our portfolio at Serena Ventures to be super strong and super powerful. 

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Long before launching Serena Ventures, Serena was already making strategic investments. But it was the stark reality that less than 2% of venture capital funding goes to women that fueled her mission. Determined to change the game, she founded Serena Ventures in 2017 alongside Alison Rapaport Stilman, with a bold vision: to support founders whose ideas and innovations level the playing field for women and people of color.

With a $111 million fund and powerhouse limited partners like Norwest Venture Partners, CapitalG (Alphabet’s growth fund), and LionTree, Serena Ventures operates out of the San Francisco Bay Area, focusing on early-stage investments across consumer products, technology, media, healthcare, e-commerce, and wellness. To date, the firm boasts a diverse portfolio of 85 companies, each a testament to Williams' commitment to rewriting the investment playbook.

SW (Clip):

I started it because, I was at a, I was at a, a seminar and, this, this woman was speaking about how less than 2% of all VC money went to women venture capital, venture capital money went to women and people, and even less one to people of color. 

if you look at our portfolio, it's super diverse. We invest in white men as well because, you know, I'm actually married to a white man. So it's all about having diversity and just enjoying every single pot, you know, and just you just can't pick from one pot is just mixing that all together.

And that's really important for me. And that's something I also want to teach my daughter and teach people that you just it's just better you get better ideas, it’s just always better. So that's kind of how we started when we started this portfolio. And that's the direction we're still going in.

“She’s not just a celebrity investor”

Alex Rodriguez (Clip):

I know Serena as an investor. She's been investing since 2013, and she's passionate and she's good and she's as disciplined. And she has big, big plans…

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At the 2024 DealBook Summit, Williams shared that she and her husband, Reddit co-founder Alexis Ohanian, maintain separate investment portfolios. She also reflected on her 15-year journey as an investor—a natural evolution driven by her curiosity about the forces shaping the future, from transportation and technology to consumer trends. And this needs to be said – 

SW (Clip):

I hate the word celebrity because I consider myself just a normal person and just a person that loves investing.

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For many celebrities, investing is a vanity play—a way to attach their name to a hot startup without truly understanding the intricacies of building a business. The headlines are full of cautionary tales: high-profile names backing overhyped ventures that crash and burn, from ill-fated luxury apps to cryptocurrency disasters. Even Kim Kardashian’s SKKY Partners recently faced a setback, a stark reminder that star power alone doesn’t guarantee success in venture capital.

SW (Clip):

One thing I've learned is that, unless the people writing the checks are making a change, it's never going to make a change. So for me, it was really important to be the person doing the actual investing, the person actually writing the checks because I'm actually going to look at a company that, a Latina female started. Maybe someone else, they might not naturally look at it because they just like, oh, you know, let me just look at this company. So I'm naturally going to look at that. 

So my idea now is to help the people that are writing the checks and have more women and more people of color actually write those checks, so we can build that diversity even more. 

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Serena Williams, however, took a different path. Recognizing that great athletes and great investors don’t always overlap, she made a conscious decision to go beyond the surface-level game. Rather than relying on her brand alone, she immersed herself in Silicon Valley, sitting in on meetings, shadowing CEOs, and learning firsthand from industry leaders. She took board seats at companies like SurveyMonkey and Poshmark, the latter giving her invaluable insight into what it actually takes to take a company public—an experience far beyond just writing a check.

Williams’ approach is a blueprint for how celebrity investors should engage: not as passive participants, but as students of the game. Where others might chase trends, she built expertise, ensuring that when she speaks in the boardroom, she’s not just a famous name in the room—she’s a decision-maker.

A Portfolio that Speaks Volumes

📊 85+ portfolio companies across multiple industries
🚀 53% female-founded businesses
📈 76% led by Black, Latino, or other underrepresented entrepreneurs
🦄 14 companies have reached unicorn status to date ($1B+ valuation)

These aren’t just numbers—they’re a blueprint for systemic change. Serena Ventures is breaking down barriers, ensuring capital flows to those historically excluded from the table. The firm has backed market disruptors well before they hit the mainstream, including:

• MasterClass – The edtech powerhouse valued at $2.75 billion (CNBC, 2021)
• Impossible Foods – A leader in plant-based meat alternatives
• Noom – A revolutionary weight-loss app powered by behavioral science
• Karat – A platform helping companies hire elite engineering talent
• Tonal – A smart home gym system, where Serena Ventures played a key role in its $45 million Series C funding in 2019

SW (Clip):

We don't want to check a box. We just want to be able to impact that life.

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Serena’s approach to investing embodies true leadership—recognizing opportunities where others see obstacles and aligning financial returns with meaningful impact. Her journey proves that success isn’t just about making bold moves—it’s about making the right ones.

And here’s a bonus takeaway, inspired by this year’s Super Bowl halftime show—regardless of where you stand on Kendrick’s performance, my focus was locked on Serena.

Key Takeaway #5: Reclaiming Joy, Redefining Power at your own pace

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When Serena took the Super Bowl stage last week—surrounded by Kendrick Lamar and other unapologetic Black artists—she wasn’t just dancing. She was reclaiming something.

Contrast that with Wimbledon, where she once faced criticism for celebrating too passionately:
At Wimbledon: "Immature and classless," said one commentator. She was even pressured to apologize for celebrating a gold medal.

Clip:

We were at the Olympics and Serena… Serena had just won a gold medal. And when she was on the sidelines, she broke out into a little dance. 

“I'm not sure I've ever seen that from Serena Williams.” 

So the media was like “Serena c-walks after winning gold medal.”

We're not intentionally trying to be like, oh yeah, let's ruffle all the feathers in the tennis world. Like, that's not what's happening. What's really happening is we want to be able to live out loud. 

SW (clip):

*Kendrick Lamar’s Superbowl performance* 

Man. I did not like that at Wimbledon. Oh, I would have been fire... It was all love. 

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At the Super Bowl: She was free. She laughed, she danced, she embraced joy without restraint. And of course gave a hat tip to her Black culture. 

And therein lies the lesson: power isn’t just about dominance. It’s about the freedom to take up space without apology.

This isn’t just about Serena. It’s about every Black woman who has had to shrink themselves to fit into spaces not built for them. Studies show that 79% of Black women feel the need to change their behavior at work to make others comfortable (Catalyst). 54% of Black women leaders feel pressured to modify their communication or appearance (McKinsey). And yet companies with inclusive cultures are 2x more likely to exceed financial targets (Deloitte).

So, here’s the real question: If Serena Williams—23 Grand Slams, a global icon—couldn’t be fully herself at Wimbledon but found that freedom on the Super Bowl stage… how many Black women are still holding back their magic?

How many are still dimming their light?

How many are still dancing smaller than they dream?

In an era where anti-DEI sentiment threatens to stall progress, the need for bold, strategic leadership has never been greater. But here’s the truth: equity and inclusion aren’t just initiatives—they’re the foundation of high-performance teams, resilient businesses, and groundbreaking innovation. The goal isn’t to retreat but to redefine and rebuild. The playbook needs a reset.

And if there’s anyone who knows the power of reinvention, resilience, and betting on the future, it’s Serena Williams.

Let’s recap the Serena Williams Playbook for Billion-Dollar Moves

✅ Stay Authentic – Own your story, don’t shrink yourself.
✅ Bet on Emerging Trends – See potential where others see risk.
✅ Master Resilience – Fail forward, come back stronger.
✅ Champion Diversity – Invest in people, ideas, and industries that others overlook.
✅ Build a Legacy – Success isn’t just about winning—it’s about who you uplift along the way.

Serena Williams didn’t just change tennis—she changed the game everywhere she played.

🔥 How has Serena Williams’ leadership inspired you? What did I miss?