Serena Williams – A New Baseline
Fast Company|Winter 2020/2021
Whether she wins that 24th Grand Slam singles title or not, tennis star and venture investor Serena Williams is working tirelessly to keep her career in play,
By Nicole Laporte. Photographs by Djeneba Aduayom

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 co-founder 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 like 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 the 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.

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

"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.

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 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 IPObound 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.”

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