Serena Williams, Eva Longoria, Elisabeth Moss Discuss Business at Milken

Serena Williams' Venture Capital Journey and the Power of Investing

Serena Williams, one of the most iconic athletes in history, has taken her passion for excellence beyond the tennis court. At the Milken Institute conference, she made a bold statement about her work in venture capital, emphasizing that this phase of her career could be even more impactful than her athletic achievements.

During a Q&A session at the Beverly Hilton hotel, Williams spoke about her investment ventures under the Starfire banner. She described how she approached this new chapter with the same discipline and dedication she applied to her tennis career. "This part of my career is going to be much bigger than anything I've ever done before," she said confidently.

Williams started as an angel investor but quickly realized the need for a more structured approach. She spent years building relationships with founders, understanding the ecosystem, and expanding her portfolio. "I spent at least three years of getting to know founders, getting to know people, getting to know companies, investing a lot more, building up my cadence, building up my portfolio," she explained. "And then we launched our first fund with just years of being disciplined, going through the process and understanding what we wanted to do."

VC, according to Williams, is a game of who you know. She emphasized the importance of connections and the power of leveraging her network to support underrepresented founders. "I just wanted to change people writing the checks. I think if the same people are writing the same checks, it's always going to be this circle that continues," she said. "But when you shake that up – setting aside a certain percentage to go to women, to go to underrepresented founders - I feel like it's changing the landscape of the top of the funnel."

The Broader Landscape of Celebrity Investors

Williams was not alone in her venture capital pursuits. Other prominent figures, including Eva Longoria, have also made significant inroads into the world of investing. During a May 6 session, Longoria discussed how she leveraged her personal brand to invest in creative projects and technology-driven companies.

Longoria highlighted the value of trust and influence in the entertainment industry. "If you look at Hollywood and celebrity culture - we're trusted voices within a certain market," she said. "I'm Hispanic. I'm a woman of a certain age, so you might go, ‘That's pretty targeted.' And I probably have a bigger distribution than NBC or ABC – like, I could reach more people."

She also shared a story about her early investment in the "John Wick" franchise. "It was my naivete that allowed me to take that risk. Because it's a very high-risk venture to invest in movies. We don't know what's going to hit," Longoria explained. However, her faith in director Chad Stahelski and writer Derek Kolstad paid off, as the franchise went on to make $1 billion at the box office.

The Intersection of Law, Technology, and Entertainment

Kevin Yorn, Longoria’s longtime lawyer, also shared insights into the evolving landscape of celebrity investing. He highlighted the growing importance of technology and the role of AI in shaping the future of entertainment. "I'm investing in responsible AI," Yorn said. He pointed to the AI-driven audio firm ElevenLabs, where Matthew McConaughey has invested. "We were the first ones to do it with an artist," Yorn added.

Yorn also discussed the value of celebrity personal brands in the consumer goods and retail space. He cited Hailey Bieber's Rhode beauty brand as a prime example. "Everybody knows beauty brands are so hard. They all fail pretty much every single time," he said. However, Bieber's success was due to a combination of trust, quality, and strategic content creation through OBB Media.

Building Trust in Creative Collaborations

Trust was also a central theme in the conversation between Elisabeth Moss and Warren Littlefield. Their partnership on Hulu's "The Handmaid's Tale" and its prequel "The Testaments" showcased the importance of collaboration and mutual respect. "When you're embarking on a project, I think the most important decision - especially as an actor, whether you're a producer or not - is that first decision of who are you getting into bed with," Moss said.

Littlefield emphasized how Moss proved herself as a producer from the start. "You were in pretty much every scene, so the workload that we were putting on your shoulders day and night and on weekends was tremendous," he recalled. Moss's contributions helped shape the Emmy-winning series, which ran for six seasons on Hulu.

The Future of Investing and Innovation

As the conversations at the Milken Institute conference demonstrated, the intersection of sports, entertainment, and technology is creating new opportunities for innovation and investment. From Serena Williams' venture capital efforts to Eva Longoria's strategic investments, these individuals are redefining what it means to be a successful investor in the modern era.

Their stories highlight the importance of trust, vision, and the ability to adapt to changing landscapes. Whether through supporting underrepresented founders, investing in emerging technologies, or building long-term partnerships, these leaders are shaping the future of business and entertainment.

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