Of all the gear that Serena Williams relies on to keep her playing at the top of her game, the piece of equipment she might value most is Toggl, an app that helps track her time, breaking down what percentage of each day goes to the three things that consume her most: her family, her businesses, and, of course, tennis.
“It’s really good for me, because at the end of the day I can say how much time I spent” on each area of her life “and how it adds up,” she says. Williams tweaks her schedule based on the Toggl data, especially if it shows that she has not been spending ample time with her 3-year-old daughter, Olympia.
“I want my percentage with my daughter to be a lot.”
Williams is a self-proclaimed tech junkie, whose digital obsession has only deepened since she tied the knot with Reddit cofounder and venture capitalist Alexis Ohanian in 2017—their engagement was fittingly announced on Reddit. When it comes to cool apps, “I have a cheat sheet because my husband is in this business,” she says with coy understatement, as though Ohanian were some IT guy. The ones she checks in with most regularly are Zero, to track her eating schedule (she fasts intermittently, typically not eating until noon), and the ubiquitous work mainstays Slack and Zoom. She’s beaming in today via the latter from her home in West Palm Beach, Florida, dressed in a plain black T-shirt with her thinly braided hair pulled loosely back. As she changes from one pair of stylish, black-framed glasses to another in order to better see the screen, she comes across more as a bookish editor than someone routinely called, without any hedging or qualification, the greatest tennis player of all time.
Williams, 39, is one Grand Slam singles title shy of matching the record set by any man or woman—24—held by Margaret Court since 1973. Winning a 24th title, she says, is “quite frankly the only reason I’m still playing.” But on this October afternoon, with towering Florida palm trees visible through the window behind her, Williams isn’t in competition mode. After making it to the semifinals of the U.S. Open in August, where she and her family underwent daily COVID-19 tests, she proceeded to the French Open. Then, early on in the tournament, she dropped out due to an Achilles’ heel injury and is now channeling her superhuman energy into other areas of her Toggl pie chart.
One of the largest wedges is devoted to Serena Ventures, a venture fund she founded in 2014 that invests in companies primarily founded by women, people of color, and other entrepreneurs who traditionally have not been heard—or funded—by Silicon Valley. Every week or so, she reaches out to one of the 60-plus founders, asking things like, “How do we build the brand?” and “What can I do?” she says.
Other slices are devoted to what she calls her “S umbrella,” a constellation of personal brands comprising an eponymous, ethically sourced jewelry line and S by Serena, her three-year-old, affordable-clothing company designed for women of all shapes—Williams renamed plus sizes to “great” sizes. She’s involved on a granular level, sketching garments (on Pinterest boards that she’s had to make private because “I was starting to get a lot of followers”), weighing in on packaging design, and debating the merits of hero designs versus GIFs on the web page. She is also working with the Hollywood talent agency and media conglomerate WME to launch a multimedia company.
As always with Williams, her pursuits are tightly wrapped up in her own narrative and brand, one that the world has been aware of since she and her sister Venus disrupted the lily-white world of tennis more than two decades ago, smashing its culture and expectations to bits. She won the 2017 Australian Open while pregnant—a typical, Williams-style feat. (A day after delivering Olympia, her C-section incision burst due to coughing caused by blood clots that had formed in the arteries in her lungs; she was dangerously close to death.) When she showed up to the 2018 Grand Slam tournament rocking a black compression catsuit, French Open officials deemed the ensemble “inappropriate.” She responded by showing up next in a black frilly tutu and fishnet tights. Williams uses her unique position as a powerful, self-made Black woman to address racism and sexism—she’s been a vocal advocate for pay equity in tennis—and has always made a point of being self-defined. Yet her business forays, while thoughtful and strategic, are in some ways restrained. With Serena Ventures, for example, she’s not throwing money at the next big IPO-bound startup but making long-term investments toward a more equitable future.
Creating change is time-consuming. When asked how this week’s breakdown is looking on Toggl, her face relaxes, and she gives a sly chuckle. “I’m loving it, because I don’t have to work out.”
“Olympia’s asleep right now, or else she would be here,” Williams says over Zoom. She seems relieved by this, a feeling any working parent of young children would understand. Earlier in the day, while talking to one of her venture fund founders, she played Legos with Olympia at the dining room table. “I felt like she needed extra time [with me],” Williams says of her daughter. “Tomorrow she can come to my office, but today I was in her office.”
Williams’s life rarely aligns like this. There are the Zoom calls “where there are 20 eyeballs on Serena, and she’ll slide some nail polish over to Olympia so she can paint her nails while Serena very coolly answers a question about an opportunity,” says Chidinma Asonye, COO of S by Serena. Olympia is a regular at investment committee meetings for Serena Ventures, and at one pre-pandemic meeting at Nike, which has long sponsored Williams, Williams fille was seated in the middle of the conference table in a baby seat “like she was the CEO,” jokes Jill Smoller, Williams’s longtime agent at WME Sports. Things don’t always go completely smoothly, such as the time Williams was filming an InstagramTV beauty routine and Olympia discovered her lipstick collection.
When Williams is training for tournaments, she’ll grind it out on the court from 9 a.m. until 1 p.m. During that window, everyone around her knows she’s off-limits. “Morning time is tennis time,” Williams says, simply. “Afternoon time is business time. I’m really, really organized with my time.”
This discipline extends to meetings, which “she joins on time or a minute before,” says Asonye. “She is going to beat you to the dial-in.” Often, Asonye continues, she’ll text, “ ’I’m on my way home, I’m running three minutes late.’ If she’s going to be [even] three minutes late, she’s going to give you a heads-up.”
Leading a business and parenting are both endeavors that require a high level of communication and juggling others’ needs. Tennis, meanwhile, is a solo sport where the focus can only be on two things: that little yellow ball and the person on the other side of the net. Williams gets consumed by it.
“When Serena is training, that’s all she’s thinking about,” says Smoller. When she loses a big match, it’s a major blow and she can “get very dark and down on herself and wants time alone.” But Williams can no longer check out as she mentally resets after a loss. “She always shows up for her baby,” Smoller says. “She doesn’t have that luxury to disappear, because she’s a mom.”
“Life moves,” Williams says. “If you’re not moving, Olympia’s making you move.”
Williams has spent a good chunk of her life in the ready position, a fact that primed her to be flexible in business. When she was dreaming up her S by Serena line, for example, she was forced to pivot even before the company’s 2018 launch, when several major retailers turned down the idea of partnering with her on it.
“They weren’t interested,” she says. “A lot of celebrities were coming out with a lot of different brands at the time, and I don’t know if they were successful. Or maybe they just didn’t want me, I don’t know.”
For advice, Williams turned to Vogue editor-in-chief and Condé Nast artistic director Anna Wintour, a friend and mentor since Williams was 16. Wintour recalls telling her, “You can just go direct to consumer.” Wintour says the advice was logical, seeing as Williams “is in direct communication with her customer. So often the success of a designer is about how they connect with the person who’s actually buying their clothes. And Serena has that ability.”
The company debuted with the campaign “What Is Your S?,” which was an invitation for consumers, including Williams’s millions of social media followers, to share personal experiences and perhaps purchase an S logo pin or T-shirt. Williams defined her own S’s as “strength,” “survive,” and “sometimes just overall being strong.”
“From day one,” she says, S by Serena “has been about community and not about money. Obviously, we do need to stay afloat, but we also want our customers to be happy when they’re wearing our clothes.” Indeed, S by Serena, based in New York City, is a lean operation, with fewer than two dozen employees, some of whom are freelancers. When COVID-19 hit last spring, Williams was forced to rely on her agility. She opted not to apply for a PPP loan (“other companies needed it way more than us”) and cut back on spending. The company also used fabric from in-stock items to make masks—with the S logo, of course—and they quickly became a best seller.
“Retail’s the last business, quite frankly, that you wanted to be in when this happened,” Williams says. But “you can’t give up, and you have to think of a second way.”
How Serena Williams Invests Her Time: A Look At Her Wide-Ranging (Non Tennis) Pursuits
The importance of having a backup plan was drilled into Williams at a young age by her dad, with whom she is still close. Richard Williams, after seeing a tennis player on TV collect $40,000 from a tournament win, decided that he could train his daughters to become stars (he learned to play by watching instructional videos). Yet he always stressed pursuing more than just tennis.
This meant that while Serena and Venus were training on public courts in L.A.’s Compton neighborhood, where Richard would ask local kids to come boo at them in order to teach his daughters how to focus and block out mental (and actual) noise, they also took Spanish and French and weren’t allowed to practice tennis if they didn’t do their homework. “Our bodies are so frail, right? Here today, gone tomorrow—or can’t walk tomorrow. He was always stressing to us: have a plan B.”
Williams studied fashion at the Art Institute of Fort Lauderdale from 2003 to 2005—”in between winning Wimbledons and U.S. Opens,” she says. In 2011, she began taking kinesiology (the study of the mechanics of body movement) and premed classes at UMass Amherst. Her intent was to finish her degree, but she ended up pulling out when she became pregnant with Olympia. She began investing, in 2014, in companies such as Olly, a women’s vitamin and nutrition startup, using her own capital. She had watched tech companies like Google and Facebook grow into juggernauts, and even as a world-famous athlete, she’d felt left out. Why hadn’t she been able, or asked, to invest in them? “That was my thinking,” Williams says. “How do I get in the ‘in’ crowd? . . . I mean, I wasn’t making a billion bucks a week, but I’ve been earning a check since I was 17 and I would have liked to have been able to invest in certain things. How do I get on those cap tables?”
Years later, she extended her thoughts more broadly. What about other women—and people of color—who didn’t have her clout? What were their chances of ever getting in on the next culture-defining, billion-dollar startup, let alone launching their own?
Williams knew the answer would be disheartening, but the numbers she read in 2017 were even grimmer than she’d imagined: firms led by female founders raised only 2% of all venture capital funding. That number inched up to 2.8% in 2019. As for companies led by Black founders, they currently receive less than 1% of venture capital.
Quietly, she partnered with Alison Rapaport, a JPMorgan veteran and Harvard MBA, and began putting seed money into companies such as Nude Barre, which creates color-tone undergarments and hosiery for women of all skin shades, and Billie, which sells shaving products for women at a lower cost than men’s. At the time, Williams was already sitting on the boards of SurveyMonkey and Poshmark, but she feared that her investments would be dismissed as the hobby of yet another celebrity dilettante. “I’m like, you know what? I want to do this seriously,” she says. “I want to build a portfolio. I want you to see what I’ve done, and have that speak for me.” She is deliberate about maintaining professional distance from Ohanian, who as a partner in Initialized Capital invested in such hits as Cruise, Ro, and Instacart. “Sometimes I’ll go, ‘Yeah, I invested in this company,’ ” Williams says. “And he’ll go, ‘You invested in that?’ ”
She and Ohanian “encourage each other, [and] we talk about deals sometimes,” says Rapaport, who was hired after she showed up to an interview with Williams with a bag of tacos. “But most of the time it’s pretty independent. They have different philosophies on what they invest in.”
It wasn’t until Olly was bought by Unilever in 2019—the first of Williams’s portfolio companies to have such an exit—that Williams officially announced Serena Ventures, via Instagram. Soon she made more public moves, investing in the women-swipe-first dating app Bumble not long after she starred in Bumble’s 2019 Super Bowl ad.
“The only time I don’t focus on [investing] is about eight weeks of the year, when I’m in a Grand Slam,” she says. In a Zoom interview conducted last May by her friend and mentor Aryeh Bourkoff, the founder and CEO of boutique investment firm LionTree, Williams said, “I haven’t felt this fire and this excitement since tennis,” in what might be a telling use of the past tense.
Williams and her small team—Rapaport and associate Abir Liben—push founders to invest in diverse hires. Diego Saez Gil, the Argentinian cofounder and CEO of Pachama, which uses AI to monitor forest restoration and conservation efforts, says that Serena Ventures “connected me to candidates who represented minority groups. That was important for us. We ended up hiring an incredible engineer who is female, transgender, and Black.”
Rapaport thought she was a high performer until she met Williams. “I was like, Oh, I must be type B. We have the same 24 hours [in a day], but I swear she has more.” Rapaport recalls flying to Florida last February so that she and Williams could meet with a startup founder. “I got to Serena’s house before she got there—she was coming back from tennis.” The next thing she knew, Williams “was sitting in glam, finalizing an endorsement deal she’d done for a migraine medicine, while reading a script for a Stuart Weitzman shoot she was doing the next day.” The footwear brand is just one of more than a dozen companies with which Williams has an endorsement deal.
“When I think of content, I’m not thinking about your regular, 48-minute, episodic shows. I’m thinking of something different.”
Williams is blue-skying ideas for what she’d like to do with a production company that is going through the blueprint process at WME, the media conglomerate. She’s currently talking to agents and executives at the company about the kind of entertainment she’d like to produce. She says she wants it to be “wholesome,” considering she hates watching anything violent herself. The Umbrella Academy, she says, “is as wild as it gets for me.”
Kids programming is also being discussed. As with everything Williams launches nowadays, she’s thinking about ownership: controlling what she creates and being able to put her full self behind it.
When the Black Lives Matter movement started to swell last summer, S by Serena revived its “What is your S?” campaign. On one of her “Serena Saturday” IGTV videos, where Williams shows off the latest designs and chats with her followers, she spoke somberly about her own “S’s” while wearing a black T-shirt that read “Women Who Rise.”
Raised as a Jehovah’s Witness—her two priorities in life remain “God and my family”—Williams doesn’t endorse candidates or even comment on political issues. She even demurs from going too deeply into Black Lives Matter, when pressed. “I just feel like it was—it was always a movement,” she says. “And then, as everything happened with these murders that were filmed—because, let’s be real, this happens more than what was captured on film—people started to, it was a good storm of everything combining,” meaning that the fact that so many people were at home created an opportunity to reflect on the racism in our country. People, she said, “had more time to actually open their eyes.”
Then she stops herself. “Other than that, I really don’t have an answer to that question,” she says, her voice fading.
But it’s clearly something she feels a need to address. During a “Serena Saturday” video at the height of the racial justice protests in June, Williams said, “A lot of people don’t know, my whole life I’d had to deal with so many challenges and had to endure inequality, have had to deal with racism. Unfortunately, it’s become somewhat of a norm for people who have my skin color.”
Ohanian was seated next to her. The couple—he in a black T-shirt and blue sneakers, she in a short purple print dress and bright magenta heels—created a powerful visual that no slogan ever could. Ohanian had just made the bold move of stepping down from the board of Reddit, urging the company to replace him with a Black member. (It did: Y Combinator partner and CEO Michael Seibel.)
Williams says she was surprised when Ohanian first mentioned his plan to her a few weeks earlier. “I wasn’t sure, because I didn’t know where he was going with it,” she says. “I’m like, ‘Wait, what are you doing? Why would you do that?’ That was my initial reaction,” she goes on. “But once he explained himself, I was like, ‘Okay, well come off, now!’ ”
Time she gets up
“Around 7 or 8 a.m. That’s only because Olympia’s awake. I don’t necessarily get out of bed.”
First thing she does in the morning
“I check my phone.”
Productivity apps or tools she uses
“Toggl. Slack. [Fasting app] Zero. Pinterest, lately. And [disposable-camera app] Dispo.”
Last thing she does at night
“I watch TV. [So] the last thing I do is press play on my computer. Yes, I watch TV on my computer now.”
Time she goes to bed
“There’s no time. I don’t sleep a lot. I could go to bed at 11, but go to sleep at 2. I go to bed, but I won’t sleep. I’m just not a good sleeper.”