Serena Williams delivered a bold statement during a Q&A session about her work in venture capital at the Milken Institute conference.
“This part of my career is going to be much bigger than anything I’ve ever done before,” the tennis great said confidently from the stage at the Beverly Hilton hotel as she discussed her myriad investment ventures that flow through her Starfire banner.
Williams, who has been a trailblazer for female athletes since she was a teenager, discussed her love of investing and the work of nurturing founders and promising ventures in her wide-ranging conversation with Jason Kelly, a Bloomberg News correspondent and host of “The Deal” sports business podcast.
Williams started out as an angel investor. But as she grew to understand the eco-system, she realized she wanted Starfire to play a bigger role. And she approached it like an athlete in training.
“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,” Williams said. “And then we launched our first fund with just years of being disciplined, going through the process and understanding what we wanted to do,” Williams said. “VC is a game of who do you know.”
Williams’ May 5 session was one of several held during Milken’s May 3-6 conference that shed light on how boldface names in Hollywood are using their experience in entertainment and their leverage as celebrities to make serious inroads as investors.
Eva Longoria, the actor/director/producer and co-founder of Hyphenate Media Group, described her journey in placing big bets with capital during a lively conversation with Kevin Yorn, who is her longtime lawyer. Yorn also moonlights as an investor through his Broadlight Capital banner, as he explained i the May 6 session moderated by Rebecca Keegan, senior Hollywood reporter for NBC News.
Another prominent pair spoke about a different kind of investment, one rooted in creative taste and trust, that has established a producing partnership that has yielded two successful TV series to date, with more on the horizon. Warren Littlefield, the veteran producer and longtime NBC executive, and actor/producer/director Elisabeth Moss detailed how they came together as partners on Hulu’s “The Handmaid’s Tale” and its recently launched prequel “The Testaments.”
In her conversation with Kelly, Williams explained that she is motivated by knowing that less than 2% of all VC money flows to female entrepreneurs. And she is excited about the potential to tap into her connections and resources to help grow technology-driven companies with the potential to change the world.
“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,” Williams 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. There’s so many companies in our portfolio that are doing so well because of us, and they’re going to be massive, massive companies because of what we bring to the table.”
Williams is energized by the opportunity to invest in firms that will influence “how we live our lives, how we let our kids live our lives,” she said. “With everything that’s happening in AI today, we need to be looking at these opportunities. We need to make sure that we also are investing in that because this is as big, if not bigger, than the industrial revolution.”
Longoria zeroed in on how she has deftly leveraged the value of her personal brand in a business context during her May 6 session with Yorn and Keegan.
“If you look at Hollywood and celebrity culture — we’re trusted voices within a certain market,” Longoria 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,” Longoria said. “Brands want that end user, and they want the conversion. Because it’s not just about clicks and likes. They want you to convert. How many things did we sell and how many? Or are we exposing a brand, or are we trying to get people to buy something? And so what’s the call to action with these brands?”
Yorn offered his perspective that Longoria was a natural as an investor, as someone who had strong instincts about material and the courage of her convictions. Yorn cited a bit of little-known Hollywood history that Longoria’s firm stepped in with a key source of funding more than a decade ago when the first “John Wick” action film was coming together.
“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.
Fundamentally, Longoria explained that she had faith in director Chad Stahelski and writer Derek Kolstad and their vision for an action movie franchise headed by Keanu Reeves.
“They were young, scrappy and hungry. They had this relentless drive and hunger to make the best action movie anybody’s ever seen. And you go, wow, there was like, no denying that they were going to not fail,” she said. “I didn’t fund the whole movie, but I did [provide] emergency situation funds. And ‘John Wick’ [franchise] went on to make $1 billion at the box office. Again, it was about investing in people who are going to execute what they say they’re going to do.”
For Yorn, being an investor who is exposed to the cutting-edge of tech innovation has had benefits for his day job as an advocate for creative artists. It certainly helped him drive a path-breaking deal recently completed for client Matthew McCounaghey to trademark his distinctive voice and likeness as a guard against AI thievery.
“I’m a protector of intellectual property My goal is to protect someone’s stealing somebody’s voice,” Yorn said. “I’m investing in responsible AI.” On that score, he pointed to the AI-driven audio firm ElevenLabs
“Matthew McConaughey is very into AI, and he and he did invest with ElevenLabs, and he almost insists that he wants to use ElevenLabs with certain things that he’s doing. But at the same time, I’m his lawyer, and I’m going to get yelled at by everyone in Hollywood. ‘What the heck are you doing? You got McConaughey going to ElevenLabs and all of a sudden voice actors are gonna be out of work and all this stuff.’ But the same time I have to look at things like, what’s happening here? This is not going away. We actually trademarked his voice and we also trademarked his likeness. We were the first ones to do it with an artist.”
Yorn also touched on the soaring value of celebrity personal brands in the area of consumer goods and retail extensions. The way that Hailey Bieber’s Rhode beauty brand leverged branded content to build awareness of Rhode is a prime example, as Yorn detailed.
“Everybody knows beauty brands are so hard. They all fail pretty much every single time,” Yorn said.
“We have this person who could be trusted because she represents beauty. And then she had to find the right group to help with making the stuff that people use. It’s got to actually work. But then the third thing was that she was smart enough to connect up with a company called OBB Media. All they do is create content with the storyteller in a way that really resonates with their audience. They just have a special skill,” Yorn said. “So she had three things that were the special sauce — massive social media following and trust, a good operator who helped make the product. And then third, this unbelievable amplification of this amazing group that helped her tell a story. And then it worked.”
The importance of building and maintaining trust in business relaitonships was a key theme for Moss and Littlefield during their May 4 conversation moderated by Cynthia Littleton, co-Editor in Chief of Variety. Moss shared the story of how she asked her talent representatives to “bring me a Warren Littlefield-type” of producer to work with when she first set out to star in and produce “Handmaid’s Tale” for Hulu more than 10 years ago. She was overjoyed when Littlefield himself turned up.
“It’s so much about trust,” Moss said. “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. Who are you going to be standing alongside? Who’s going to be making those 200 decisions that you make when you are preparing for a show?”
Moss detailed the gestures and the decisions small and large that Littlefield and “Handmaid’s Tale” showrunner Bruce Miller made out of respect for her role as a producer. For actors, it can be a fraught process to be taken seriously in a different role behind the camera. Littlefield and Miller made Moss feel like a full partner from the start of the Emmy-winning series that ran for six seasons on Hulu, Moss said.
“There were 100 things they did that first season,” Moss recalled. “I’ve been very spoiled. I know that’s not normal.”
Littlefield told Moss that he recognized from the start she had the makings of a great producer, in part because of how she juggled the competing demands on her time.
“You were in pretty much every scene, so the the workload that we were putting on your shoulders day and night and on weekends was tremendous,” Littlefield recalled. “And yet Lizzie wanted to be in these production meetings. We would shoot two episodes together at a time. We were usually $3 million to $4 million over budget as we were prepping and had to get the budget there. And you were part of the solution, part of the process of saying ‘I wonder if we could combine this, and what if we did this?’ And so it became really clear to us that [Moss’ producing credit] wasn’t just a reward because you were amazing actor in the show. It was because you had producing muscle.”
(Pictured top: Eva Longoria and Kevin Yorn at 2026 Milken Global Conference)
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