Winning sometimes feels different. [Video]

Tennis legend and venture capital investor Serena Williams took to the stage with business partner Allison Rappaport Stillman this week at TechCrunch disablednoting that winning feels different on VC-land than it does on the tennis court.

Usually when you invest in early stage as we are, first and foremost, you don’t get 100% winners,” Williams told the audience.

“Sometimes winning isn’t about owning a unicorn or a $500 million business,” she added. “Sometimes winning looks different, but you know what winning looks like to me – so I’m still working on that balance, that you can’t pick winners 100%.”

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

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

Williams recently retired From tennis, she got into VC with Stillman, who worked for JP Morgan and Goldman Sachs earlier in her career. Although many athletes have dabbled in venture capital in recent years, Williams’ connections to technology and VCs are particularly long-standing. Started Serena Ventures in 2014, she is married to Alexis Ohanian, co-founder of Reddit, who is also an investor. It’s a remarkably difficult VC natural views For now, however, it seems Williams hasn’t been intimidated by the venture capital long game, with returns sometimes taking decades.

“It took me 17 years to win my first major, so I can wait, I’m good at waiting,” Williams said. “Impatient.”

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

“We can’t have a venture capital firm and never have a foot in Web3 because it’s the future but we also want to make sure we’re thoughtful about the process,” Williams said.

For Williams and Stillman, there were also deals that got away. Those missed investments include the passenger carrier that Williams declined to name and grocery delivery startup Instacart, which could be set to go public in Expected future.

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

Serena Ventures co-founders and directors Allison Rappaport Stillman and Serena Williams speak on stage during TechCrunch Disrupt 2022 on October 19, 2022 (Photo by Kimberly White/Getty Images for TechCrunch)

Serena Ventures co-founders and directors Allison Rappaport Stillman and Serena Williams speak on stage 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, revealing that first fundraising wasn’t necessarily easy. From the start, the two wanted to approach venture capital with an eye on diversity.

“We have gone really, really hard to include people who look like us, look like the people we serve,” Stillman said. “We made strategic decisions about how we thought about the size of the check, and who to let in because we wanted to open that door… So, it took us a little bit longer, but we’re really proud of it. We love it when we have our LP [limited partner] The events we watch are people who are like our team, who are 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 have to keep growing with every quarter,” Williams said.

Allie Garfinkle is a senior technical reporter at Yahoo Finance. Follow her on Twitter at Tweet embed.

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