What does it mean to leave a legacy? For Olympic champion Jordan Chiles, the answer isn’t just in the medals or the perfect 10s—it’s about impact, longevity, and staying power. Sound familiar? It should. Because if there’s one name in sports that defines reinvention, it’s Serena Williams. Williams built an empire beyond her 23 Grand Slam titles from the courts of Compton to global boardrooms. And Chiles? She’s watching, learning, and dreaming just as big.
Williams isn’t just a tennis icon, but she has set a blueprint for athletes redefining their careers beyond sport. From investing in startups to owning a piece of an NWSL team, she’s built an empire that stretches far beyond the baseline. And for Jordan Chiles, that’s exactly the kind of legacy she hopes to create.”Business-wise, I have to say Serena Williams,” Chiles said to Forbes when asked about who she looks up to. “Serena Williams, business-wise, she has done so much. And when I mean so much—didn’t she just—yeah, she purchased a team?” she added.
Williams, a part-owner of Toronto’s NWSL expansion team, has continued to make waves long after her legendary tennis career. And for Chiles, that kind of staying power is exactly what she wants for herself.”She’s a part owner of Toronto, and I’m literally like, ‘This lady has done so many amazing things, not just within her career but also with just keeping her name in the loop.’ And I think that’s just so amazing because I want to be able to do that,” Chiles said. “I want to be able to continue on, you know, whenever my career does come to an end and people still know, ‘Oh, Jordan Chiles did this. Jordan Chiles did that.’”
It’s not just about business, though. Williams’s influence on Chiles extends beyond ownership deals and investments—it’s about being a powerhouse both in and out of sport.”So she’s definitely somebody I do look up to from a business standpoint,” Chiles said. “But also as an athlete, you know.”
Chiles, who won a gold medal at the 2024 Paris Olympics, returned to familiar territory—UCLA gymnastics and has set the season on fire, already scoring two perfect 10s. She returned to UCLA for the 2025 season after competing in 2022 and 2023. “I’m a college student now. That’s crazy to say, right?” Chiles laughed. But for her, it’s about growth—not just as an athlete but as a person.
“Yes. But if you think about it—we were just talking about this, right? People were—we were just talking about how Megan, yeah, was a college student. She graduated. How Kendrick—people—that whole picture that went all over Twitter and TikTok, he—you know, getting your degree isn’t going to change who you are, whether you’re a rapper, whether you’re an athlete, whether you’re becoming a doctor, or any of those things. It’s just going to give you more knowledge, and you’re going to retain a lot more things.”
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