Talking With Serena Williams: Her Brand; Her VC Company

(L. to r.) Guru Gowrappan, CEO, Verizon Media; Serena Williams; and Julia Boorstin, Entertainment & Media correspondent, CNBC. Credit: AWNewYork/Shutterstock

When Serena Williams begins to figure out the next steps for her clothing brand, she asks her self one question, then acts on the answer. “I always ask myself, ‘What do the best do?’,” she said. “And then I do that and then try to do it a little bit better,” she says.

Olympic tennis athlete and entrepreneur, Williams spoke with Guru Gowrappan, CEO OF Verizon Media, and Julia Boorstin, CNBC’s entertainment and media correspondent, at this week’s annual New York Advertising Week Conference. She opened up about her retirement from tennis (“in 20 years or so,” she joked), her role as chair of Verizon’s board of advisors, her clothing company and venture firm, and… strollers!

Williams’ initial foray into entrepreneurship resulted from her passion for fashion. She showcased her clothing brand, “S,” at New York Fashion Week earlier this month.

“When I first started, I wanted to be more of a brick and mortar store and have people see the fabrics and feel them. But as I got more involved in technology—and my husband’s in tech—I definitely wanted to go D2C, cut out the middleman, and cut down on prices for customers,” she explained.

Williams has been described as fearless, but she contends that fearlessness is more about being brave. To illustrate, she revealed that she was not 100 percent sure about going into the venture capital business, but did so anyway. Established quietly in 2014, her firm, Serena Ventures,” to date has made 30 investments.

She delayed announcing the launch of the firm. “I wanted to have a great portfolio,” she explained. “We really try to invest in companies that have a self-belief. Also, you have to trust your instinct. If they don’t seem reputable or as if they’re just in it for a quick turnaround… then we understand that they might not be the company that we want to invest in.”

Williams’ mentors also advised her to come up with a motto or plan to guide her investment decisions. “I realized I’m interested in technology, but I’m also more interested in founders,” she admitted.

As a venture capitalist, she has become better acquainted with the challenges women in business face, she says, and noted, “I realized that less than two percent of female founders were getting funded, which I thought was staggering.”

That made her take a second look at her own portfolio and implement changes. “We have new rules. I just want to make sure we look at everyone and give everyone opportunity, but we really focus on female founders,” she said.

The company offers more than just funding. “Lately, I realized, as someone who wants to invest money, you also have to invest into the company. If the company is going to be successful, they’re going to need your support. I try to get involved and give tons of feedback,” Williams remarked.

Even when she passes on funding a company, Williams still tries to help the business get off the ground. “We don’t invest in all the companies, but I have a platform where I can say, ‘This is a great company, I can introduce them to other amazing VC firms that might like the idea or have that funding to finance.’”

Williams, who married Alexis Ohanian, a tech entrepreneur, investor, and co-founder of  Reddit, the online social news aggregator and discussion platform, also spoke about her doubts when she first joined the board of Survey Monkey, which creates online surveys for free. “When I first got on that board, I was literally like a deer in headlights, I had to go back and learn so many concepts and ideas and ask questions. Eventually, I was able to offer a lot of input on that board,” she confessed.

And there’s her love affair with Colugo strollers. She explained: “Colugo is all about design…I just throw my baby in, and I’m like. ‘this is so much better than the other stroller that I hated with all my heart.’ … I don’t have to be a rocket scientist to open this stroller. I wasn’t feeling really smart with some of these strollers.”