Not having a chance to invest in major players in tech ultimately catapulted Serena Williams into the investment ring.
During an interview on Bloomberg’s “The Deal,” Williams recalls a time in her tennis journey when she could have faced less pressure to win on the court if she had placed dollars in companies such as Facebook, Airbnb and Google — all companies valued at more than $100 billion today.
“Tennis is all sponsor based, and I would see like some of these sponsors come up, but I’m like, ‘Well I have some little cash, like how did I not invest in Facebook? How can I invest in Airbnb or how did I miss Google? Or like, you know, all these companies,'” Williams said on “The Deal.” “And I started to ask these questions like, ‘Why am I out here breaking my neck and sweating when I could have invested in these companies and I could still be doing the same thing, but it wouldn’t have to be such dire needs, ‘I’ve gotta win this U.S. Open this year. I’ve gotta pay these bills.’ So, I literally would be on the court looking at these sponsors thinking, ‘how did I miss this?'”

Williams would take greater initiative and venture to Silicon Valley, California, with a curious mind. She educated herself in the area, which she describes as a “super boys’ club” and would pick the brains of one of the founders of Pinterest.
“I remember even just sitting in Pinterest at the time one day and just learning from the founder there and just being a sponge and just trying to understand the business, understand investing, understand all this stuff a little bit more. And that’s kind of how it all started,” she said.
Williams would find a fascination in early-stage startups, although at the time she didn’t know that’s what they were.
“I didn’t realize that it was called early stage. I just liked companies that were starting, and then I liked growing them,” she explained.
Among those early-stage investments was Masterclass, which was created by a small group in a San Francisco, CA, garage. The edtech startup was valued at $2.75 billion in 2021, as previously reported by CNBC.
In 2014, Williams established Serena Ventures, alongside Alison Rapaport Stillman. The venture capital firm empowers women and underrepresented founders, including fintech company Esusu, which reached a $1 billion valuation in 2022, per TechCrunch.
Serena Ventures’ portfolio companies also include Parfait, Karat, and Calico, among others.
“Our portfolio right now as it stands is 68% women or persons of color, and that is unheard of in the VC world,” Williams mentioned to Bloomberg. “And so for me it’s all about diversity and bringing everyone together. We invest in literally everyone. We don’t care what you look like, but we hear your story.” 
Williams says since her start in investing, she has continued to land more deals and has added 16 unicorns to her personal portfolio over time. This positioned her to be in better standing to launch a fund.
“I worked on doing more deals, ended up getting about 16 unicorns in my portfolio,” Williams said. “So that way I would have a good track record, ’cause I knew it wouldn’t be probably easy for us to raise a fund first go-around.”
As AFROTECH™ previously mentioned, Serena Ventures’ inaugural fund was announced in 2022 to support early-stage startups and totaled $111 million.