Serena Williams wasn’t just a teenage tennis sensation—she was also learning the ropes of business before she could even legally vote. At 16, she was already earning big paychecks from tournaments and sponsorships. However, her father, Richard Williams, ensured she knew how to manage her money. When she was negotiating a massive $13 million deal with Puma, he didn’t just handle the talks himself. Instead, he took her along while negotiating with a major investor and movie producer, Arnon Milchan. Those early lessons stuck with Serena, and today, she’s a powerhouse in venture capitalism. And now she’s revealing how she tackles the business world!

Fast forward to 2025, and Williams is making waves in the business world. Even though she retired from tennis in 2022, her impact didn’t stop at the baseline. At 43, she is the founder of Serena Ventures, a venture capital firm focused on early-stage companies, particularly those led by women and minorities.

At this year’s #UpfrontSummit, the American tennis icon sat down with David Fialkow of General Catalyst to discuss her investment journey. And let’s just say, it’s been a learning curve. “For me, the one thing that I had to kind of wrap my head around and get used to was the fact that you are going to lose a lot,” Serena admitted.

“And it’s like wait, I don’t like that but VC is—and especially because we do early stage—what that really is just about understanding that you’re going to swing and miss even though it might be great. It might be something that’s amazing. You did your due diligence. You did everything you’re supposed to do, and you could definitely miss and so for me, that is the hardest part. The hard work is different, I enjoy that. But the swing and miss is something that I’m still trying to understand,” said Serena.

That’s a mindset shift for a 23-time Grand Slam champion who spent her entire career refusing to lose. But Williams isn’t one to back down from a challenge. Her passion for venture capital started after a J.P. Morgan Chase conference, where she learned a shocking statistic: Less than 2% of all VC money went to women.

In a Vogue essay, she recalled her reaction. “I kind of understood then and there that someone who looks like me needs to start writing the big checks. Sometimes like attracts like.”

Serena Williams took that realization and ran with it. In 2025, Serena Ventures raised $111 million for its inaugural fund and supported over 60 companies in various sectors, such as health, technology, transportation, and sustainable fashion.

Interestingly, her long-time rival, Maria Sharapova, is also an active investor. The Russian star has her own candy company called “Sugarpova” and has also invested in numerous ventures like the tech wellness brand, Therabody, and the Ultimate Fighting Championship (UFC).

But investing in startups isn’t the only game she’s playing. Serena and her husband, Reddit co-founder Alexis Ohanian, are also changing the landscape of women’s sports.

Serena Williams and husband champion women’s sports

In 2020, Alexis Ohanian became a founding investor in Angel City FC, a Los Angeles-based National Women’s Soccer League (NWSL) team. The Williams-Ohanian family, including their daughter Olympia, owns a stake in the club. In 2024, Disney CEO Bob Iger and his wife, Willow Bay, became the team’s majority owners, valuing the franchise at $250 million.

Still, the Ohanian-Williams family didn’t stop there. They set their sights on something bigger.

Ohanian made headlines with his brainchild ATHLOS NYC, a groundbreaking event in women’s sports. The competition boasted a prize pool of at least $500,000, with $60,000 going to the winner, $25,000 for second place, and $10,000 for third. And guess who was the driving force behind his push for equal pay? None other than Serena Williams.

In an interview with CNBC, Ohanian shared the moment that changed his perspective. “Wouldn’t it be great if she played on a national team one day?” Alexis quipped as they watched soccer.

But Serena responded rapidly: “Not until they pay her what she’s worth.” That comment hit home. “And I was like, ‘Touché, okay, challenge accepted.’ And that’s what motivated me to buy a team and help be a part of the change,” Ohanian said.

Serena Williams is no longer dominating the tennis court, but she’s still playing to win. And now, she’s making sure others get their shot, too. What do you think about her impact on business and women’s sports?