Serena Williams made a bold statement during a question-and-answer session about working 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,” the tennis great said confidently on stage at the Beverly Hilton Hotel, speaking of the myriad investment ventures flowing under the Starfire banner.
A pioneering female athlete since her teens, Williams spoke about her love of investing and her work developing founders and promising ventures in a wide-ranging conversation with Jason Kelly, a Bloomberg News correspondent and host of the sports business podcast The Deal.
Mr. Williams started out as an angel investor. But as we learned more about the ecosystem, we wanted Starfire to play a bigger role. And she approached it like an athlete in training.
“I spent at least three years getting to know the founders, getting to know the people, getting to know the companies, making more investments, picking up the pace, and building the portfolio,” Williams said. “And we stayed disciplined, went through the process, figured out what we wanted to do, and launched our first fund in just a few years,” Williams said. “VC is a game of who you know.”
Mr. Williams’ May 5 session was one of several held during Mr. Milken’s May 3-6 conference, highlighting how Hollywood’s boldest names are using their entertainment industry experience and celebrity influence to make serious inroads as investors.
Actor, director, producer, and Hyphenate Media Group co-founder Eva Longoria talks about her journey making big bets with her capital in a lively conversation with longtime attorney Kevin Yorn. Yorn also announced his position as an investor through the Broadlight Capital banner, as explained in a May 6 session moderated by NBC News senior Hollywood correspondent Rebecca Keegan.
Another high-profile pair talks about a different kind of investment, rooted in creative flair and trust, establishing a production partnership that has resulted in two successful TV series to date, with many more on the way. Veteran producer and longtime NBC executive Warren Littlefield and actor/producer/director Elisabeth Moss detail how they partnered on Hulu’s The Handmaid’s Tale and its recently released prequel, The Testaments.
Warren Littlefield and Elisabeth Moss discuss their production partnership for The Handmaid’s Tale and Testament at the Milken Institute Conference on May 4th at the Beverly Hilton Hotel.
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In a conversation with Kelly, Williams explained that she was motivated by the knowledge that less than 2% of VC money goes to women entrepreneurs. And she’s excited about the possibility of leveraging her connections and resources to help grow technology-driven companies with the potential to change the world.
“I just wanted to change who’s writing the checks. I think if you have the same people writing the same checks, it’s always going to be a cycle,” Williams said. “But I feel like when we shake that up, things are changing at the top of the funnel, like making sure we have a certain percentage going to women and underrepresented founders. We have a lot of companies in our portfolio that are doing very well because of us, and they’re going to become huge, big companies because of what we bring to the table.”
Williams said he is energized by the opportunity to invest in companies that impact “how we live and how we feed our children.” “With everything that’s happening with AI today, we need to look at these opportunities. This is as big as the industrial revolution, if not bigger, so we need to make sure we’re investing in it as well.”
During a May 6 session with Yorn and Keegan, Longoria focused on how he has skillfully leveraged the value of his personal brand in a business context.
“If you look at Hollywood and celebrity culture, we are trusted spokespeople within certain markets,” Longoria said. “I’m Hispanic. I’m a woman of a certain age, so you might think, ‘I’m pretty targeted,’ and we probably have a bigger distribution than NBC or ABC, so we can reach a lot more people,” Longoria said. “Brands want end users, they want conversions, because it’s not just clicks and likes. They want you to convert. How many products have we sold? Or are we exposing the brand, or are we trying to get people to buy something? So what’s the call to action for these brands?”
Mr. Yorn expressed the view that Mr. Longoria is a natural investor, a person with strong instincts about materials and the courage to stand by his beliefs. Yorn cited a little-known Hollywood history in which Longoria’s company stepped in as a major source of financing when the first action movie “John Wick” was in production more than a decade ago.
“It was my naivety that allowed me to take that risk, because investing in movies is a very risky business. You never know what’s going to happen,” Longoria explained.
Basically, Longoria explained that he trusts director Chad Stahelski, screenwriter Derek Kolstad, and their vision for the Keanu Reeves-led action film franchise.
“They were young, they were hungry, they were hungry. They had a relentless drive and hunger to make the best action movie anyone had ever seen. And there was no denying that, wow, they weren’t going to fail,” she said. “I didn’t fund the entire movie, but I did fund the contingency, and John Wick (the series) went on to make $1 billion at the box office. Again, this was about investing in people who were going to do what they said they were going to do.”
For Jorn, being exposed to cutting-edge innovation as an investor also benefits his day job as an advocate for creative artists. This certainly helped facilitate our client Matthew McNaghy’s recent landmark deal to trademark his distinctive voice and likeness as a defender against AI theft.
“I’m a protector of intellectual property. My goal is to protect someone from stealing someone’s voice,” Yorn said. “I’m investing in responsible AI.” In this regard, he pointed to AI-driven audio company ElevenLabs.
“Matthew McConaughey is very interested in AI, and he’s also invested in Eleven Labs, and he’s almost going to claim that he wants to use Eleven Labs for 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, saying, ‘What the hell are you doing? You let McConaughey go to Eleven Labs? But at the same time, you have to look at what’s going on here. We actually trademarked his voice, and we trademarked his likeness. We were the first to do that with an artist.”
Mr. Yorn also noted the soaring value of celebrity personal brands in consumer goods and retail expansion. A prime example is how Hailey Bieber’s Lorde beauty brand leveraged branded content to increase Lorde awareness, as detailed by Yohn.
“We all know that beauty brands are very difficult. They fail almost every time,” says Yorn.
“We have someone that this person can trust, because she represents beauty. And she had to find the right group of people to help her make something that people would use. It has to actually work. But third, she’s OBB We were smart enough to partner with a company called Media. All they do is create content with storytellers in a way that really resonates with the audience. They just have a special skill set. “So she had three things that made her special sauce: a huge following and trust on social media, a great operator who helped her create the product, and thirdly, an incredible amplification of this amazing group of people who helped her tell the story. And it worked.”
The importance of building and maintaining trust in business relationships was a key theme for Moss and Littlefield in a May 4 conversation moderated by Variety co-editor-in-chief Cynthia Littleton. Moss revealed how, when he was first cast and produced on Hulu’s The Handmaid’s Tale more than a decade ago, he asked a talent representative to “bring in a Warren Littlefield-type producer” to work with him. She was overjoyed when Littlefield himself showed up.
“It’s all about trust,” Moss said. “When you embark on a project, especially as an actor, whether you’re a producer or not, I think the most important decision is the first decision of who you’re going to bed with. Who are you going to stand next to? Who’s going to make the 200 decisions you make while preparing for a show?”
Moss detailed the actions and decisions, big and small, that Littlefield and The Handmaid’s Tale showrunner Bruce Miller made in honor of their roles as producers. For actors, getting taken seriously for another role behind the camera can be a difficult process. Moss said Littlefield and Miller made her feel like full partners from the beginning of the Emmy-winning series, which aired for six seasons on Hulu.
“There were 100 things they did in the first season,” Moss recalled. “I’ve been very spoiled. I know that’s not normal.”
Littlefield told Moss that he knew from the beginning that she had the makings of a great producer, in part because of how she juggled competing demands on her time.
“You were in almost every scene, so the workload we were putting on your shoulders day, night and weekend was enormous,” Littlefield recalled. “And yet, Lizzie wanted to be in these production meetings. We shot two episodes together at a time. We were preparing, so we were usually $3 million to $4 million over budget, and we had to come up with the budget there. And you know, we’re over budget by $3 million to $4 million over budget. And then you have a solution. That was part of the process of thinking, ‘Can we put this together? What would happen if we did this?”’ So it really became clear to us that[Mos’ producing credit]wasn’t just a reward for you being a great actor on the show. That’s because you have muscles. ”
(Top photo: Eva Longoria and Kevin Yorn at the 2026 Milken Global Conference)
