Serena Williams may have retired in 2022 from a record-breaking professional tennis career that catapulted her to global fame, but her post-tournament life keeps her as professionally engaged as ever, albeit in a different field.
Williams, 43, is the founder of Serena Ventures, a venture capital fund that invests in early-stage companies, particularly those founded by women and minorities. Established in 2017, when Williams was at the height of his career, the company has raised $111 million for its inaugural fund and has invested in more than 60 brands.
Serena Ventures is made up of a team of seven people, including Williams, and backs companies that positively impact “the everyday lives of everyday people,” she said.
Among them are Parfait, a black-owned brand that uses AI (artificial intelligence) and facial recognition to create custom wigs and hair extensions, and Halp, a company that helps students navigate the process of studying abroad and make it more accessible.
Serena Ventures is also involved with media and entertainment brand Boss Beauty and Wile, a line of herbal supplements for women over 40.
In addition to her investment fund, Williams’ professional activities include Wyn Beauty by Serena Williams, a makeup line with products made with vegan ingredients and few chemicals. She also has memberships in sports teams, including, according to her, the Miami Dolphins.
In her conversation on the DealBook Summit 2024 main stage with event founder Andrew Ross Sorkin, Williams spoke about her competitive nature and her family relationships. She said that although her father, Richard Williams, could be perceived as tough, her mother, Oracene Price, was “much tougher”.
“So my dad was actually super kind and would always say, ‘Are you okay? Do you need a break? Let’s take a break,'” Williams told Sorkin.
She also shared that she lived with her sister and tennis competitor Venus Williams until she married Reddit co-founder Alexis Ohanian in 2017, and that she and Ohanian keep their investments separate. But she noted, “he’s a wonderful investor.”
Williams spoke with The New York Times shortly before taking the stage at the Summit.
The interview, also conducted via email, has been edited and condensed.
Why are you interested in investing? And why focus on early-stage companies?
Many people don’t know that I’ve been investing for 15 years. It was natural.
I started thinking about what will shape our world, be it through transportation, technology, consumer goods. Whatever it was, I wanted to be part of that transformation. I want to invest in B2B companies [business-to-business] and learn how you could invest in early-stage companies early and reap a big payoff. I didn’t know all the jargon at the time. I didn’t know this was called early stage investing and that it was a thing. I didn’t know venture capital was a thing. But it’s something that attracted me because I’m a curious person.
How did you learn the basics?
I went to Silicon Valley and sat in different offices. I would call CEOs and ask if I could spend a few days with them and ask them questions. At Pinterest in particular, I knew one of the guys on the board, and he understood that I had a lot of questions. It was cool to go to companies like this and learn.
Eventually, I started joining boards: Survey Monkey, Poshmark. Poshmark was a great opportunity to learn the ins and outs of taking a company public. I expanded my horizons with the vision of wanting to be a better investor, doing this in the long term and building a team. This was before I had a team.
Luckily, because of my hard work in tennis, I have had different opportunities to go to companies and talk to the Sheryl Sandbergs of the world.
Investing at an early stage offers a greater reward but also a greater risk. Have you ever been afraid of risks?
For me, this is the hardest part. I love winning and succeeding, but in the early stage, 70% or 80% of the businesses you invest in fail. I don’t like it. Having to accept this is difficult for me.
If one of our companies doesn’t do well, it’s heartbreaking. Often, they don’t do well simply because they can’t raise funds. Unfortunately, you see this happening a lot with companies led by women or people of color. They have a great product, but difficulty getting past the initial stage.
It all comes down to marketing and how people will learn about your product.
How do you find companies to invest in?
We received many proposals. We love business-to-business investing and still have our focus on consumers. We found it through word of mouth. Sometimes you get the best deals from founders of other VC firms. In venture capital, 90% of the game is relationships and connections — maintaining those connections by having constant calls with people at other companies and asking them what they’re doing and sharing what we’re doing.
We want to operate like a venture capital firm with our sleeves rolled up, where people want to see Serena Ventures on their cap table and know that we can bring different things.
One example is Rebelstork. They work with open boxes of items — their focus is babies. Let’s say someone receives a gift that’s a crib, and they don’t want or need it, so they return it to the retailer. The retailer throws this crib in the landfill because they have to do so due to policy. The founder [Emily Hosie] is taking these open boxes and selling them at a lower price, which helps mothers and with pollution. This aligns with our thesis of solving big problems for everyday people.
What other ventures have resonated with you?
There is a company called Esusu. If you pay rent, it doesn’t help your credit score. How do you get a mortgage without a credit score? My mother, after all these years of paying rent, never improved her credit scores. If you are a tenant and pay rent on the Esusu platform, you can build credit. Even I, who won Grand Slams, had to take on debt to get credit.
The company helps tenants and landlords because if you’re a tenant, you’ll get paid on time, and if you’re a landlord, you’re encouraged to build your credit.
What have you learned from your endeavors?
I learned about the non-financial investments that are so important. Beyond funding, it’s about opening doors for founders to create opportunities. Whether it’s making a connection with a major retailer, offering executive coaching, or bringing exposure to the companies we invest in, there’s more to Serena Ventures than quantitative investing.
What’s the best investment advice you’ve received, and what advice do you have for aspiring investors?
Do your due diligence and don’t rely on someone else. I do this with every company.
I invest in early-stage companies, and many of these [investimentos] do not return. When I invest, I think I’m not going to see this again, so the best advice I would give is to invest in companies that you believe in and expect to invest money that you won’t see back.
Tell me about Wyn Beauty. What was the impetus to start? What business lessons did you learn and how did you develop the name and packaging?
I started Wyn Beauty because I have always believed that beauty should be for everyone and that performance beauty is essential to living a confident life. I spent my career pushing my body, and I realized that the beauty products I used didn’t always meet my needs. Wyn Beauty answers. It is created for individuals like me who are constantly on the move.
Our chartreuse packaging is a reference to the tennis ball, which is a reference to my victories on the court, a mindset we want to bring to our products and the experiences you have when using them.
With Wyn Beauty, I learned that building a business requires patience and resilience — it doesn’t always mean instant success. You have to be willing to change direction when things don’t go as planned.
I’ve learned to trust my instincts in any venture or brand I’m championing. As an athlete, I’ve had to make quick decisions under pressure, and in business I’ve found that trusting yourself, even when there’s uncertainty, is crucial to making bold moves that pay off.
