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Serena Williams on being a VC: 'Sometimes winning looks different'

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Serena Williams on being a VC: 'Sometimes winning looks different'

Alexandra Garfinkle
·Senior Reporter
Sun, October 23, 2022, 4:29 AM·3 min read

Serena Williams, tennis legend and venture-capital investor, took the stage with business partner Alison Rapaport Stillman this week at TechCrunch Disrupt, noting that winning looks different in VC-land than it does on the tennis court.

"Usually when you're investing as early stage as we are, seed and pre-seed, you don't get 100% winners," Williams told the audience.

"Sometimes winning isn't about having a unicorn or a $500 million company," she added. "Sometimes winning looks different, but you know how winning looks for me— so I'm still working on understanding that balance, that you can't pick 100% winners."

Serena Williams speaks onstage during TechCrunch Disrupt 2022 on October 19, 2022. (Photo by Kimberly White/Getty Images for TechCrunch)
Serena Williams speaks onstage during TechCrunch Disrupt 2022 on October 19, 2022. (Photo by Kimberly White/Getty Images for TechCrunch)

Williams recently retired from tennis, going all in on VC with Stillman, who worked at J.P. Morgan and Goldman Sachs earlier in her career. Though many athletes have gotten into VC in recent years, Williams's connections to tech and VC are particularly long-standing. She started Serena Ventures in 2014, and she's married to Reddit co-founder Alexis Ohanian, who's also an investor. It's a notably difficult VC landscape right now, but Williams appears to be undaunted by the long game that is VC, where returns sometimes take decades.

"It did take me 17 years to win my first Grand Slam, so I can wait, I'm good at waiting," said Williams. "I'm patient."

Serena Ventures' portfolio currently includes direct-to-consumer wig customization platform Parfait, fashion supply chain software-maker Calico, and customer service software provider Chatdesk. Williams and Stillman highlighted their focus on Web3, where they've already made investments like Nestcoin, which seeks to make cryptocurrency more accessible.

"We can't have a VC company and not have a foot in Web3 at all, because it is the future but we also want to make sure we're thoughtful about the process," said Williams.

For Williams and Stillman, there have also been deals that got away. Those missed investments include a ride-hailing company that Williams declined to name and grocery delivery startup Instacart, which could be set to IPO in the foreseeable future.


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