Serena Williams delivered a daring statement during a Q&A session about her work in enterprise capital on the Milken Institute conference.
“This a part of my profession goes to be much larger than anything I’ve ever done before,” the tennis great said confidently from the stage on 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 teen, 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 off as an angel investor. But as she grew to know the eco-system, she realized she wanted Starfire to play an even bigger role. And she or he approached it like an athlete in training.
“I spent a minimum of three years of attending to know founders, attending to know people, attending to know corporations, investing so much more, build up my cadence, build up my portfolio,” Williams said. “After which we launched our first fund with just years of being disciplined, going through the method and understanding what we desired to do,” Williams said. “VC is a game of who do .”
Williams’ May 5 session was considered one of several held during Milken’s May 3-6 conference that make clear 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 full of life conversation with Kevin Yorn, who’s 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.
One other distinguished pair spoke about a distinct type of investment, one rooted in creative taste and trust, that has established a producing partnership that has yielded two successful TV series up to now, with more on the horizon. Warren Littlefield, the veteran producer and longtime NBC executive, and actor/producer/director Elisabeth Moss detailed how they got here together as partners on Hulu’s “The Handmaid’s Tale” and its recently launched prequel “The Testaments.”
Warren Littlefield and Elisabeth Moss speak about their producing partnership on “The Handmaid’s Tale” and “The Testaments” on the Milken Institute conference on May 4 on the Beverly Hilton hotel.
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In her conversation with Kelly, Williams explained that she is motivated by knowing that lower than 2% of all VC money flows to female entrepreneurs. And she or he is happy concerning the potential to tap into her connections and resources to assist grow technology-driven corporations with the potential to vary the world.
“I just wanted to vary people writing the checks. I feel if the identical individuals are writing the identical checks, it’s at all times going to be this circle that continues,” Williams said. “But once you shake that up – setting aside a certain percentage to go to women, to go to underrepresented founders — I feel prefer it’s changing the landscape of the highest of the funnel. There’s so many corporations in our portfolio which can be doing so well due to us, and so they’re going to be massive, massive corporations due to what we bring to the table.”
Williams is energized by the chance to take a position in firms that may influence “how we live our lives, how we let our youngsters live our lives,” she said. “With the whole lot that’s happening in AI today, we must be these opportunities. We want to make sure that that we are also investing in that because that is as big, if not larger, than the commercial revolution.”
Longoria zeroed in on how she has deftly leveraged the worth of her personal brand in a business context during her May 6 session with Yorn and Keegan.
“In case you have a look at Hollywood and celebrity culture — we’re trusted voices inside a certain market,” Longoria said. “I’m Hispanic. I’m a girl of a certain age, so you may go, ‘That’s pretty targeted.’ And I probably have an even bigger distribution than NBC or ABC – like, I could reach more people,” Longoria said. “Brands want that end user, and so they want the conversion. Since it’s not nearly clicks and likes. They need you to convert. What number of things did we sell and what number of? Or are we exposing a brand, or are we attempting to get people to purchase something? And so what’s the decision to motion 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 little bit of little-known Hollywood history that Longoria’s firm stepped in with a key source of funding greater than a decade ago when the primary “John Wick” motion film was coming together.
“It was my naivete that allowed me to take that risk. Since it’s a really high-risk enterprise to take a position 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 author Derek Kolstad and their vision for an motion movie franchise headed by Keanu Reeves.
“They were young, scrappy and hungry. That they had this relentless drive and hunger to make the most effective motion movie anybody’s ever seen. And also you go, wow, there was like, no denying that they were going to not fail,” she said. “I didn’t fund the entire movie, but I did [provide] emergency situation funds. And ‘John Wick’ [franchise] went on to make $1 billion on the box office. Again, it was about investing in people who find themselves going to execute what they are saying they’re going to do.”
For Yorn, being an investor who’s exposed to the cutting-edge of tech innovation has had advantages for his day job as an advocate for creative artists. It actually helped him drive a path-breaking deal recently accomplished for client Matthew McCounaghey to trademark his distinctive voice and likeness as a guard against AI thievery.
“I’m a protector of mental property My goal is to guard someone’s stealing anyone’s voice,” Yorn said. “I’m investing in responsible AI.” On that rating, he pointed to the AI-driven audio firm ElevenLabs
“Matthew McConaughey may be very into AI, and he and he did invest with ElevenLabs, and he almost insists that he wants to make use of ElevenLabs with certain things that he’s doing. But at the identical time, I’m his lawyer, and I’m going to get yelled at by everyone in Hollywood. ‘What the heck are you doing? You bought McConaughey going to ElevenLabs and rapidly voice actors are gonna be out of labor and all these things.’ But the identical time I actually have to take a look at things like, what’s happening here? This shouldn’t be going away. We actually trademarked his voice and we also trademarked his likeness. We were the primary ones to do it with an artist.”
Yorn also touched on the soaring value of celebrity personal brands in the world of consumer goods and retail extensions. The way in which that Hailey Bieber’s Rhode beauty brand leverged branded content to construct awareness of Rhode is a primary example, as Yorn detailed.
“Everybody knows beauty brands are so hard. All of them fail just about each time,” Yorn said.
“We now have this one who could possibly be trusted because she represents beauty. After which she had to search out the best group to assist with making the stuff that individuals use. It’s got to truly work. But then the third thing was that she was smart enough to attach up with an organization called OBB Media. All they do is create content with the storyteller in a way that basically resonates with their audience. They simply have a special skill,” Yorn said. “So she had three things that were the special sauce — massive social media following and trust, operator who helped make the product. After which third, this unbelievable amplification of this amazing group that helped her tell a story. After which it worked.”
The importance of constructing 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 got down to star in and produce “Handmaid’s Tale” for Hulu greater than 10 years ago. She was overjoyed when Littlefield himself turned up.
“It’s a lot about trust,” Moss said. “While you’re embarking on a project, I feel crucial decision — especially as an actor, whether you’re a producer or not — is that first decision of who’re you moving into bed with. Who’re you going to be standing alongside? Who’s going to be making those 200 decisions that you just make when you’re preparing for a show?”
Moss detailed the gestures and the selections small and huge that Littlefield and “Handmaid’s Tale” showrunner Bruce Miller made out of respect for her role as a producer. For actors, it will possibly be a fraught process to be taken seriously in a distinct role behind the camera. Littlefield and Miller made Moss feel like a full partner from the beginning of the Emmy-winning series that ran for six seasons on Hulu, Moss said.
“There have been 100 things they did that first season,” Moss recalled. “I’ve been very spoiled. I do know that’s not normal.”
Littlefield told Moss that he recognized from the beginning she had the makings of a fantastic producer, partly due to how she juggled the competing demands on her time.
“You were in just about every scene, so the the workload that we were putting in your shoulders day and night and on weekends was tremendous,” Littlefield recalled. “And yet Lizzie desired to be in these production meetings. We might shoot two episodes together at a time. We were normally $3 million to $4 million over budget as we were prepping and needed to get the budget there. And also you were a part of the answer, a part of the means of saying ‘I ponder if we could mix this, and what if we did this?’ And so it became really clear to us that [Moss’ producing credit] wasn’t only a reward since you were amazing actor within the show. It was since you had producing muscle.”
(Pictured top: Eva Longoria and Kevin Yorn at 2026 Milken Global Conference)