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‘Sometimes winning looks different’ [Video]

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)

Williams recently retired from tennis, going all in on VC with Stillman, who worked at JP 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. “Eager.”

Serena Ventures’ portfolio currently includes direct-to-consumer wig customization platform Perfect, 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.

“We saw Instacart, but it was a little bit too late for us, and that was another one where there really was still a lot of room for growth,” said Stillman. “We could have made an exception there, but it was their Series B… that would have been a nice one to get into.”

Serena Ventures founding and managing partners Alison Rapaport Stillman and Serena Williams speak onstage during TechCrunch Disrupt 2022 on October 19, 2022. (Photo by Kimberly White/Getty Images for TechCrunch)

Serena Ventures founding and managing partners Alison Rapaport Stillman and Serena Williams speak onstage during TechCrunch Disrupt 2022 on October 19, 2022. (Photo by Kimberly White/Getty Images for TechCrunch)

Serena Ventures’ approach to diversity

Williams and Stillman founded Serena Ventures in 2014, and revealed that the first fundraise wasn’t necessarily easy. From the beginning, the two wanted to approach VC with a focus on diversity.

“We made a really big effort to include people who looked like us, looked like the people we’re serving,” said Stillman. “We made strategic decisions about how we thought about check size, and who we let in because we wanted to open up that door… So, it took us a little longer, but we’re really proud of that. We love that when we have our LP [limited partner] events that we’re seeing people who look like our team, look like our founders.”

Currently, 40% of Serena Ventures LPs are women and people of color.

“I want everyone to win, at least everyone we invest in and we’ve got to really continue to grow with every quarter,” said Williams.

Allie Garfinkle is a Senior Tech Reporter at Yahoo Finance. Follow her on Twitter at @agarfinks.

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