Serena Williams made a striking declaration during a Q&A session on her venture capital endeavors 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 icon asserted confidently from the stage at the Beverly Hilton hotel while discussing her various investment projects under her Starfire banner.
Williams, a pioneering figure for female athletes since her teenage years, expressed her passion for investing and supporting founders and promising ventures in her conversation with Jason Kelly, a Bloomberg News correspondent and host of “The Deal” sports business podcast.
Initially an angel investor, Williams realized the potential for her Starfire ventures to have a greater impact as she learned more about the ecosystem. She approached this venture like an athlete in training.
“I spent at least three years getting to know founders, people, and companies, investing more, building up my cadence, building up my portfolio,” Williams explained. “Then we launched our first fund after years of disciplined effort, understanding what we wanted to do,” she said. “VC is a game of who you know.”
On May 5, Williams participated in one of several sessions during Milken’s May 3-6 conference that highlighted how notable figures in Hollywood are leveraging their entertainment experience and celebrity status to make significant strides as investors.
Eva Longoria, an actor, director, and producer, and co-founder of Hyphenate Media Group, shared her experience in making substantial investments during a lively discussion with Kevin Yorn, her longtime lawyer. Yorn, who also invests through Broadlight Capital, explained in the May 6 session moderated by Rebecca Keegan, senior Hollywood reporter for NBC News.
Another notable duo discussed a different kind of investment, one rooted in creative vision and trust, which has led to a successful producing partnership resulting in two hit TV series so far, with more expected. Warren Littlefield, a veteran producer and longtime NBC executive, and actor/producer/director Elisabeth Moss shared how they collaborated as partners on Hulu’s “The Handmaid’s Tale” and its prequel “The Testaments.”
Warren Littlefield and Elisabeth Moss talk about their producing partnership on “The Handmaid’s Tale” and “The Testaments” at the Milken Institute conference on May 4 at the Beverly Hilton hotel.
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In her discussion with Kelly, Williams revealed her motivation stemmed from the fact that less than 2% of all venture capital funding goes to female entrepreneurs. She expressed enthusiasm about using her connections and resources to help grow technology-driven companies with transformative potential.
“I just wanted to change the 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 stated. “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 are so many companies in our portfolio that are thriving because of us, and they’re going to be massive companies because of what we bring to the table.”
Williams is invigorated by the chance to invest in firms that will shape “how we live our lives, how we let our kids live our lives,” she remarked. “With everything happening in AI today, we need to look at these opportunities. We need to make sure we’re also investing in that because this is as big, if not bigger, than the industrial revolution.”
Longoria emphasized how she effectively leveraged her personal brand in a business setting 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 noted. “I’m Hispanic. I’m a woman of a certain age, so you might think, ‘That’s pretty targeted.’ And I probably have a larger 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 commented that Longoria was a natural investor, with strong instincts and the courage of her convictions. He shared a little-known story about how Longoria’s firm provided crucial funding over a decade ago when the first “John Wick” action film was being developed.
“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 elaborated.
Longoria explained that she had faith in director Chad Stahelski and writer Derek Kolstad and their vision for an action movie franchise starring 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 no denying that they weren’t going to fail,” she recalled. “I didn’t fund the whole movie, but I did provide emergency situation funds. And the ‘John Wick’ franchise went on to earn $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 exposed to cutting-edge tech innovation has benefits for his role as an advocate for creative artists. This was evident in a recent deal he facilitated for client Matthew McConaughey to trademark his distinctive voice and likeness to guard against AI misuse.
“I’m a protector of intellectual property. My goal is to protect someone’s voice from being stolen,” Yorn stated. “I’m investing in responsible AI.” He referred to the AI-driven audio firm ElevenLabs in this context.
“Matthew McConaughey is very into AI, and he did invest with ElevenLabs, and he almost insists that he wants to use ElevenLabs for certain things 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 at 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 discussed the escalating value of celebrity personal brands in consumer goods and retail extensions. He illustrated this with Hailey Bieber’s Rhode beauty brand, which leveraged branded content to build awareness.
“Everybody knows beauty brands are so hard. They all fail pretty much every single time,” Yorn remarked.
“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 significance of trust in business relationships was a key focus for Moss and Littlefield during their May 4 conversation moderated by Cynthia Littleton, co-Editor in Chief of Variety. Moss shared how she instructed her talent representatives to find her a “Warren Littlefield-type” producer when she first decided to star in and produce “Handmaid’s Tale” for Hulu over a decade ago. She was thrilled when Littlefield himself appeared.
“It’s so much about trust,” Moss commented. “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 small and large gestures and decisions made by Littlefield and “Handmaid’s Tale” showrunner Bruce Miller in respect of her role as a producer. For actors, transitioning to a behind-the-camera role can be challenging. Littlefield and Miller treated Moss as a full partner from the beginning 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 saw her potential as a producer from the outset, partly due to how she managed competing demands on her time.
“You were in pretty much every scene, so the workload we placed on your shoulders day and night and on weekends was tremendous,” Littlefield said. “And yet Lizzie wanted to be in these production meetings. We would shoot two episodes 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?’ So it became really clear to us that [Moss’ producing credit] wasn’t just a reward because you were an amazing actor in the show. It was because you had producing muscle.”
(Pictured top: Eva Longoria and Kevin Yorn at 2026 Milken Global Conference)
