Serena Williams’ co-investor shares what comes next for the athlete’s venture firm

August 10, 2022, 12:31 PM UTC
GPs Serena Williams and Alison Rapaport Stillman
Managing partner Serena Williams and general partner Alison Rapaport Stillman have backed about 20 companies with Serena Ventures' first fund.
Courtesy of Serena Ventures

Serena Williams made an extraordinarily emotional announcement yesterday: She is stepping away from what has been her whole life’s focus—tennis. And yet, she still showed up to her venture capital firm’s team call that morning.

“I feel like I go to sleep getting messages from her and wake up getting messages from her,” says Alison Rapaport Stillman, who is Serena Ventures’ general partner. “Nothing’s going to replace what tennis was for her, but as she’s thinking about what’s next—it’s exciting to see her as passionate about this as you see her on the court.”

You may not think “venture capitalist” when you first think of Williams, the 23-time Grand Slam champion who has become one of the world’s most famous athletes and role models to women and the Black community. But Williams started angel investing nearly a decade ago and has written checks to 16 startups that are now unicorns (think Impossible Foods or MasterClass). Venture is one of a few areas where Williams plans to spend more of her time on post-tennis: that and being a mom. 

Two years ago, Williams began setting up Serena Ventures’ first fund with Stillman, whom Williams hired in 2018 to invest in startups for her family office. In those first few months, Williams warehoused initial investments until the two of them had raised capital from limited partners. That first fund, backed by LPs including Norwest Venture Partners and Capital G, closed earlier this year at $111 million.

Stillman makes it clear that Williams has never just been a name on the door: She is actively involved.

“People are always surprised to know how in the weeds she is,” Stillman tells me, pointing out that Williams joines every weekly call, takes pitches herself, and that both she and Williams have to vote yes on something before writing a check. 

Now that she is giving up tennis, Williams will be even more involved in the firm’s work and interaction with founders, Stillman says. “That is something that she’s wanted to do for a long time and hasn’t always had the opportunity.” 

A key priority at the firm, and a major reason Stillman started working for Williams in the first place, was her focus on backing women and people of color: 78% of Serena Ventures’ portfolio fits that bill. Serena Ventures backs founders at the earliest stages: With 60% of its investments being in seed, 20% in pre-seed, and 20% in Series A.

Stillman wouldn’t disclose initial investment performance for the fund, but the two of them have backed about 20 companies with that capital and are still making investments with the first fund. Most recently, the firm invested in plant-based supplement company WILE. The firm isn’t ready to go back to market yet with a second fund, Stillman says, though “that is something that we will definitely be doing in the future.” 

The firm has grown to six people—two in operations and four investment professionals, with Williams and Stillman recruiting Pavan Sethi as an associate and Ashelë Woods as an analyst earlier this year. 

“We all in one way or another have often been overlooked and underestimated, and I think that makes us really connected with our founders,” Stillman says of the investment team. She pointed out how Williams had hopped on a call recently with a founder Stillman felt was underpricing her company. “When a founder is able to hear that from someone as inspirational as Serena… It really changed [the founder’s] whole demeanor,” Stillman says. That’s the value Serena Ventures can offer startups, according to Stillman: “A deep understanding of the long and exhausting road it takes to the top, and being able to have that winner’s mentality, to know when to push and when to slow down, and how to keep that longevity so that you don’t burn out.”

Right now, the team is focused on getting its second quarter financials out to LPs, wrapping up due diligence with a potential investment, and going through new deals. As for Williams, she still has one last tournament to finish.

See you tomorrow,

Jessica Mathews
Twitter: @jessicakmathews
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