Beauty

Serena Williams: ‘Mistakes mean that you’re strong enough to try’

The G.O.A.T may be done with tennis, but she has her sights set on a new kind of international domination. Here, Serena Williams talks motherhood, her beauty empire, investing in Black business – and “still being codependent” with Venus.

 

Every morning, Serena Williams starts her day with the mantra: “Put your best foot forward today.” This might seem straightforward coming from one of the greatest athletes of all time—someone who has not only constructed her own trophy room but also holds a record 23 Grand Slam titles in the Open Era. However, for Williams, this motto signifies a journey of personal growth.

 

 

To her, it represents acceptance. She acknowledges that she can’t be perfect all the time, nor can she always muster the strength to conquer each morning. Instead, she resolves to give her best each day. “Sometimes my best foot is going to be really wobbly. It’s going to be really unstable,” she admits, now relaxed on a couch in her game room, dressed in a vibrant fuchsia workout set and wrapped in one of her daughter’s blankets. “Every day is not going to be easy, but that’s the whole journey.”

 

 

It has been two years since Williams retired from professional tennis, concluding an illustrious career at the top of her sport. During her time, she claimed not only 23 Grand Slam titles but also four Olympic medals, numerous doubles victories, and spent 319 weeks ranked as the world’s number one in the Women’s Tennis Association. With the guidance of her parents, Richard Williams and Oracene Price, she shattered expectations in a sport often marred by racism and 𝓈ℯ𝓍ism. While it wasn’t her responsibility to fix these issues, she felt compelled to address them.

 

Now, Williams is shifting her focus. She is no longer competing in others’ games; instead, she is laying the groundwork for a new kind of international influence, determined to make her mark beyond the court.

 

 

Hence a post-retirement blueprint that revolves around not just her two daughters—Olympia, age seven, and Adira, one—whom she shares with her husband, Reddit cofounder Alexis Ohanian, but an ambitious venture fund that invests for the most part in founders who are women or people of colour (The problem: Just 2% of venture capital flows to women, and Black founders receive less than 0.5%), her makeup line WYN Beauty (The problem: Conventional makeup brands melted off her skin on the court or had paste-like formulations too thick to wear to dinner after a match), and a slew of partnerships and commitments that range from hosting the ESPYs on ESPN to serving as a parent volunteer at school (The problem: Williams can’t stand to be bored). This summer ESPN+ aired In the Arena: Serena Williams, an eight-part docuseries that serves as a career scrapbook, recalling in intimate and sometimes anguished detail the incredible highs and occasional lows of her tenure on the court.

 

Oh—also, she’s renovating her entire house. “I really realised I always need a project,” she says, stating the obvious while gesturing toward a board of carpet samples near our feet. Her tennis court is under construction too, which explains why Serena Williams has not so much as picked up a racket in three months. She’s “desperate” to play, but it becomes evident in the time we spend curled up on her couch that it’s not as if she has hours to spare for recreation.

 

Williams has timed this interview to overlap with Adira’s morning nap, having realised that it’s best to work around Adira’s sleep schedule. Olympia is in school, which means Williams must pack her personal and professional obligations into the hours between drop-off and pickup, which she likes to do herself. When she needs a break from pitch decks and investor calls, one of her favourite diversions is…doing the laundry, she tells me, smiling. “I love the smell of it,” she insists when I look skeptical. “I like things very, very neat.”

 

 

So the inherent chaos that seems to follow children everywhere was always going to test her. For years Williams optimised her time to serve her body’s needs. Disciplined is an understatement. In In the Arena, Williams remembers the moments behind the triumphant wins: injuries that could have been career-ending, gruelling training sessions, matches that almost derailed her. “You only see the finals—did she win, did she lose,” she says now. “You don’t see when I couldn’t breathe, when I was seeing stars on the court. This is letting people who are interested or who want to be motivated see: This is what it takes.”

 

When Williams was growing up, she couldn’t fathom her mother’s nerves—her need to warn and correct and caution. She and Venus had earned their sense of confidence, and she hated to hear Price’s voice in her ear, nudging her in one direction or another. “I’d be like, I know what to do!” Williams remembers.

 

Later she came to appreciate what a mother offers that not even the most relentless coach or dedicated team can: She alone has no other interest at heart but her child’s. Williams understands better now that she is a mother herself how it is that Price can call her and tell her she has been thinking and she would rather Williams not go to the beach this afternoon. (“You could drown in the ocean!”) Williams is 43 and knows how to swim, but she gets it. “I look at my mom in amazement. She did that five times, and she’s had the horrible experience of losing one of her children,” Williams says, invoking her sister Yetunde Price, who was 𝓀𝒾𝓁𝓁ed in 2003. “So you know what? You just have to keep your mouth shut and complain to your sisters.”

 

Serena Williams on Motherhood: Triumphs, Trials, and the Importance of Sharing Her Story

 

 

From the moment of conception, Serena Williams has faced anxiety regarding her daughters. It’s become part of sports lore that she discovered she was pregnant just before competing in the 2017 Australian Open, a tournament she won before revealing her pregnancy a few months later. While she enjoyed being pregnant, worry accompanied her throughout the journey. Williams candidly admits to checking her underwear for signs of blood—a potential indication of miscarriage—every day for nine months. The logistics of childbirth overwhelmed her. “It’s like, wait, what is going to happen? That’s going to open? What?”

 

Recognizing the lack of information available to women about their bodies, Williams feels a responsibility to share her experiences. “I try to tell all my friends that’s normal, and I try to be very open about my journey and the things that people didn’t talk about with me. ‘How is that going to come out of me?’” she reflects. Despite the fact that childbirth has been occurring since the beginning of time, she finds the process daunting.

 

For Williams, childbirth was fraught with unexpected challenges. In a candid op-ed for CNN, she recounted the harrowing experience of being rushed into an emergency C-section after her daughter Olympia’s heart rate dropped during contractions. Shortly after, Williams was diagnosed with a pulmonary embolism, and her surgical wound burst open. During a subsequent surgery, doctors discovered a hematoma. She was incapacitated for six weeks and considers herself fortunate to have come through with both her life and fertility intact.

 

The statistics surrounding maternal mortality are stark; Black women are three times more likely to die from pregnancy-related causes than white women, according to the Centers for Disease Control and Prevention. This alarming figure often appears in news reports, but Williams has given it a personal face. For millions around the world, she has made the issue of Black maternal mortality both personal and real.

 

When she learned she was expecting her second daughter, Adira, Williams resolved to savor the experience, despite the trauma she had previously endured and the postpartum depression that followed Olympia’s birth. She was excited to welcome another girl. “I mean, I grew up with girls. I’d honestly never been around boys unless I was dating one,” she shares. “And sisters are so special.”

 

 

She happily admits that she and Venus “are still codependent.” “Some things never change,” she says. “I don’t even want to not be codependent with her. I love her. I don’t want our lives to ever be separate.” Williams has gotten married. She is a mother. But there is no one for her like Venus. A different set of sisters might have let the game come between them. Venus and Serena remain so inseparable that when travel brings them to the same city, Williams won’t book her hotel until Venus does, so they can stay in the same place. “Tennis is so lonely,” she says. “You’re on the road for 10 or 11 months out of the year. You really rely on having someone else out there. And Venus was there, and who else was going to relate to me? We were successful, and we were Black. We leaned on each other. We lived together. We lived together until a year before I had Olympia, so literally our whole lives.” With Adira, Williams knew she would be giving Olympia a version of the most singular relationship she has.

 

So she did not want to take any chances when it came to her second daughter’s arrival. She decided to have a C-section, with four doctors on call. She knew she would not miss experiencing labor, but a part of her still felt a pang. More than most people on the planet, she understands that there can be euphoria on the other side of physical agony. “I have a very high tolerance for pain,” she says. Still, she made her peace with this delivery as she did with the last one.

 

She is—and she knows how this sounds—grateful to have experienced that kind of raw childbirth at all, “because looking back, I’ll never have that moment again,” she says. “For whatever weird reason, that kind of makes me a little sad, but that’s probably a party of one. This time I went in with a plan. I like to say I put my best effort out there, and this was no different. I literally thought about it as a Grand Slam: How can I succeed?”

 

 

Recently, Serena Williams shared photos from her maternity shoot on Instagram to celebrate a year since the birth of her daughter, Adira. While the internet only knew she had welcomed her second child in August, Williams enjoys sharing her life. She values information and doesn’t mind if Google has it too. Having made her peace with her colossal international fame, she embraces the attention. “In a way, people do know me a little bit,” she explains. “They have seen me at my biggest moments, and most people’s biggest moments aren’t public. This is what I trained for when I was younger. This has literally been my whole life.”

 

Williams emphasizes that she has never been just an athlete; she has always been an entertainer. Although she has had fewer opportunities recently to experience the thrill of a cheering crowd, she longs for that energy. “I do love it. I loved it,” she admits. “I think that’s a big piece of what I still miss. I really miss the performance.”

 

Her competitive spirit, however, remains satisfied through her ventures in business. Before retiring from tennis, Williams made strategic investments, quietly establishing herself as a venture capitalist before officially launching Serena Ventures. Her profile has grown alongside her investments, and she has now backed over 85 companies. Earlier this year, she took to TikTok to announce that 14 of these companies have become unicorns, valued at over $1 billion each. In other words, she continues to play to win.

 

When Wemimo Abbey and Samir Goel met Williams, they had pitched their company, Esusu, to 326 investors—none of whom believed in their vision. Esusu aims to help renters build credit by reporting on-time payments to credit bureaus, allowing those payments to contribute to credit scores. Abbey recalls the skepticism they faced: “It was really hard for people to wrap their head around the fact that we were creating a solution for loads of medium- and low-income people and that it was going to generate value. People saw it as a charity affair. But she got it. She said, ‘Look, rent used to be a significant cost of our expenses, but it didn’t factor into our credit. People should get credit for that.’ That conviction was really powerful and really rare. She just said, ‘I believe in this idea.’”

 

 

Abbey and Goel have since gotten used to how—and when—Williams communicates. “Five minutes” before walking onto the Met Gala red carpet in May, Goel remembers receiving a detailed email response from his investor. When Williams was in Paris for the Olympics this summer, she refused to miss Esusu’s quarterly update call and joined the meeting around 11 p.m. from her hotel. “It’s that winning mentality,” Abbey says, before invoking the famous Vince Lombardi quote: “Winning isn’t everything, it’s the only thing.”

 

Now that Olympia in particular is older, Williams is thinking about how to tell her daughters just who their mother is. She’s “tinkering” with her strategy, fine-tuning it and sometimes asking for advice. Williams is an investor in Wondermind, the “mental fitness ecosystem” that Selena Gomez and her mother, Mandy Teefey, cofounded. Teefey has become a friend, and Williams has probed her about the choices she made while raising Gomez. “She made it very clear to me that she loved the dynamics between me and Selena,” Teefey says. “She really respected that we were open with everything that we’ve gone through. I think she shares the same ethos that we do, which is if you’re given a platform and you have to deal with so much negative stuff, when you’re able to give back, that makes it worth it.”

 

Of course, both Teefey and Williams have had to accept that for all their intentional choices, there are elements of growing up in public that are beyond a mother’s control. “The other day Olympia said, ‘My mom is the most famous tennis player in the world. She’s the best to ever play tennis.’ I was like, ‘Who told you that?’” Williams remembers. Certainly Williams and Ohanian never had. She grimaces a little when she tells the story, but then a hint of a grin spreads across her face. “Okay, it made me feel really good,” she says, laughing. “She was so proud.”

 

Serena Williams: Emphasizing Personal Fulfillment Over Legacy

 

Despite her monumental achievements, Serena Williams shows no desire to create a dynasty or push her daughters, Olympia and Adira, to follow in her athletic footsteps. In fact, she shares that Olympia “isn’t into sports,” and she embraces that. Instead, Williams hopes her daughters find their own passions. Reflecting on her upbringing, she recalls her father’s encouragement: she could be anything she wanted—even a garbage collector—if she pursued it with determination. “Whatever you want to do, give it your all,” she advises. “It even says that in the Bible: ‘Whatever you do, do it wholeheartedly.’”

 

Though she doesn’t often discuss it publicly, Williams is deeply religious. Raised as a Jehovah’s Witness, she keeps a Bible within reach during our conversation. “It’s the one thing that was able to keep me grounded,” she explains. “Especially with getting famous and wealthy so early, that stuff can really change who you are as a person, and I didn’t want to change.”

 

Sometimes, she encounters videos in her social media feed that depict the Earth expanding outward to the moon, the solar system, and beyond. “We’re so small,” she remarks. While the Greatest of All Time occupies a significant place in cultural conversations, Williams acknowledges her smallness in the vastness of the universe, reminding herself of the bigger picture.

 

 

“I pray every night that the girls stay close and have a true relationship with God on their own and get to know him,” she says. “It’s the most important thing that I personally think you can do.” She hopes that in exposing them to faith, she can show them that their extraordinarily blessed existence “isn’t theirs in a way,” she says. She had to earn it. They do too.

 

Perhaps because Jehovah’s Witnesses tend to maintain political neutrality, Williams doesn’t frame her outspokenness as activism. “I don’t try to change the world, by no means,” she says. “That’s not my mission.” But when she sits with her children, she is acutely aware of how unjust it is that so many mothers don’t have the same opportunity. Equal pay and paid leave are issues that both she and Ohanian work to elevate in the public consciousness, and she’s grateful to have a partner who is as loud about their necessity as she is. “When you have men’s voices, it really helps,” she says. “We’ll say something until our faces are blue, and we’re out of breath, but when another man says it, men sadly listen.” She can’t fathom why these policies are controversial or partisan when they seem so obvious and essential. “Some women have a 𝚋𝚊𝚋𝚢 and within a week they have to be at work or get fired,” she says. “I’m like, ‘Can we get a few weeks at least? Where do we start?’ You as a woman are so frail after you have a 𝚋𝚊𝚋𝚢. Men are too. The 𝚋𝚊𝚋𝚢 needs to be around people who are able to give them what they need.”

 

This year she became the executive producer of a documentary film, currently in development, about paid leave based on GLAMOUR US’s 28 Days paid leave project. And in her own company, a woman is taking maternity leave now; her 𝚋𝚊𝚋𝚢 is a month old, and Williams coos over photos of her newborn. “I’m like, ‘I can’t wait to meet her,’ but she needs this time with her child,” she says. “It’s so important.”

 

Retirement looks different for Williams than it does for the fishing-and-crocheting set. She is as busy and committed as she’s ever been. WYN Beauty is expanding, having debuted lip glosses and peptide-infused lip liners at the tail end of summer. A few hours after I leave, she will head out for dinner with friends. She has travel on the docket. She is—no big deal—on the auction committee at Olympia’s school. She is keeping tabs on dozens of companies. She is emerging from the throes of the raising-a-newborn stage and watching both of her daughters develop their own personalities.

 

But her most awe-inspiring achievement might just be the fact that she is starting to be gentler with herself. The postpartum hormonal firestorm that she experienced after Olympia was born returned with Adira. “You never know when it can happen,” she says. “It could be a month; it could be a week. It could take a year for things to settle down a lot. We are the vessels of increasing the population, literally. It’s really just keeping a positive environment and giving yourself grace and understanding.”

 

She tells me all this with total clarity, wavering only when I ask whether she has really and truly been able to do that. “I feel like I have,” she says, trailing off for a second. “Okay, no. But I feel like I am trying. I am learning to take my time and say, ‘I just can’t do it today. I need a day off,’ and it’s okay to say that.”

 

The day before our interview, Olympia came home from school with homework. She’d been given a story to read about a little girl who wants to draw but keeps erasing her pictures.

 

“She wants the drawing to be perfect,” Williams says, knowingly. The girl in the story blots out all her progress, fixated on some ideal she can’t reach. Olympia takes after her mother in this way, and Williams can see this is a lesson she will need to instil over and over in her daughter. It’s also the one that she herself is focused on. She explained it to Olympia. She forced herself to listen too: “Mistakes mean that you’re strong enough to try.”

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