How Serena Williams brings her killer instinct to early-stage investing • ProWellTech

In a move that broke the hearts of many a tennis fan around the world, Serena Williams recently announced that she would stop playing professional tennis. But today onstage in front of a packed auditorium at ProWellTech Disrupt, she reminded us that while she brings that competitive mindset to running Serena Ventures, an early-stage VC firm, she says that her professional mindset is “quite the opposite” of her investor persona.

“I think that’s a different Serena. I’m very serene,” she says. “I’m the one that brings that very calm disposition.”

Just don’t mistake that tranquility for passivity. Williams still brings her killer instinct to investing out of her fund, along with her general founding partner, Alison Rapaport Stillman.

She also makes diversity a non-negotiable. About 40% of her LPs are women and people of color, something that is practically unheard of in the venture industry. Williams also invests — in the pre-seed, seed and Series A stages — with the mindset that financial inclusion is far more than a buzzword.

“We spend a lot of our time in consumer-facing technology because we want to build products for the communities we want to serve…” she said. “We spend a lot of time on gender and racial equity within the healthcare system, mental health and wellness. These are problems that are facing every community, but especially facing women and people of color, there’s not enough tools and services there for them. So that’s something we’re really focused on.”

Beyond that, Williams prides herself on authenticity and passion and, unsurprisingly, those are characteristics that she looks for in founders, too. According to Stillman, one of Williams’ biggest strengths is being able to read people with just one meeting — being able to tell if a founder really quickly is someone she wants to get to know better, or not.

One of the questions she asks potential portfolio companies is are they operating because “it’s a white space” or are they doing it “because it’s something near and dear to you.”

“I’ve found that usually when it’s near and dear to you, and there’s a space available for it — that’s the winning combo,” Williams said. “But if you’re doing it just because you see it’s a great opportunity, then no matter how big and open it is, it is generally never as good as someone that really has something that they’re actually passionate about.”

“We like to keep things very authentic,” she insisted. “SV has its own brand. We’re not going to do something that’s not authentic to us or something we don’t believe in.”

She also is curious about more than a founder’s previous successes. She wants to know what founders have not been successful at.

“That shows me that when times get tough, you know what’s coming and you know what to expect and failure is great,” Williams added. “I think it’s a great opportunity to learn and I don’t even like the word failure. I feel like it should be called: ‘I had an opportunity to learn’, that’s what it should be called to me because I feel like that really creates the very next best thing.”

For the unacquainted, Williams’ husband is venture capitalist Alexis Ohanian — founder of 776 and former co-founder of Reddit. Despite having done a couple of deals together in the past, Williams said the couple doesn’t talk about business at all at home and they work to “stay in their own lanes.”

“We are both so competitive,” she said. “I’m internally so competitive. You can’t read my face if inside I’m screaming and dying. We don’t want that so we keep it very separate.”

Speaking of past investments, Williams and Stillman do have a regret or two.

Early on in her investing career, Williams says she passed on a French startup because she “just didn’t have the infrastructure or the time.”

While she wouldn’t name the startup, she did say it was “before people were doing rideshares.”

But just the fact she saw its potential is validation for Williams: that her instincts were right. Stillman also says the firm passed on investing in the Series B round for delivery giant Instacart — which is now on the verge of going public — because it was a bit late stage for them.

“There was still a lot of room for growth, though,” she laughs.