The needs of her wildly competitive spirit are more easily met. Williams invested strategically before she retired from tennis and built a quiet reputation as a venture capitalist well before unveiling Serena Ventures, her formal fund. The stakes have grown with her profile. Williams has made bets on more than 85 companies. Earlier this year she took to TikTok to reveal that 14 of them are now unicorns, valued at over $1 billion. In other words, she still plays to win.

When Wemimo Abbey and Samir Goel met Williams, they had pitched their company to 326 investors—and failed to convince any of them that the venture could work. They had founded Esusu—now one of Williams’s unicorns—to help people who rent to build credit, reporting on-time payments to credit bureaus so that the money would count toward scores. “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,” Abbey says. “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.’”

Nanushka dress.

Abbey and Goel have since gotten used to how—and when—Williams communicates. “Five minutes” before Williams was to walk onto the Met Gala red carpet in May, Goel remembers, the entrepreneur received 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.”

Still, Williams seems to have no interest in creating a dynasty or raising Olympia and Adira to follow in her footsteps. Olympia “isn’t into sports,” and that’s fine. Williams would, however, like her daughters to find a calling. Her own father used to tell her she could be a garbage collector if that’s what she wanted, but she better try to be the best garbage collector. “Whatever you want to do, give it your all,” she says now. “It even says that in the Bible. ‘Whatever you do, do it wholeheartedly.’”

She doesn’t often talk about it publicly, but Williams is deeply religious. She was raised as a Jehovah’s Witness and has a Bible within reach on her desk during our conversation. “It’s the one thing that was able to keep me grounded,” she says. “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 a video pops up in her algorithm that shows the planet and expands outward to the moon, the solar system, and beyond. “We’re so small,” she says. The Greatest of All Time may take up a little more cultural real estate than the rest of us, but even Williams is tiny in the grand scheme of the universe.