Celeb Endorsements: Cash, Sweat Equity or Go for the Mega Exit?
Agents, lawyers and investors' intel on winning the complex world of brand partnerships, even if their client isn't the next Ryan Reynolds
Ashley Cullins writes about agents, lawyers and dealmakers for paid subscribers. She recently covered the art of getting an original film greenlight in 2025, how to sell an indie film now; and the fight against if-come deals. You can reach her at ashley@theankler.com
Blame George Clooney. When he, Rande Gerber and Mike Meldman sold their tequila company Casamigos to Diageo for upwards of $1 billion in 2017, stars began asking their advisors how they could follow in those footsteps. (Never mind that Dr. Dre and Jimmy Iovine sold Beats to Apple for $3 billion in 2014: It didn’t necessarily inspire scores of entertainers to start companies with an eye on that kind of exit.)
Then Ryan Reynolds turbocharged the celebrity frontman game, creating a marketing “turducken” by advertising his Aviation Gin and 2019 Netflix movie 6 Underground within a Samsung TV commercial and bringing his winking self-awareness to brands in which he had an equity stake. When Diageo bought Aviation Gin and its parent company Davos Brands in a deal worth up to $610 million in 2020 and T-Mobile paid $1.35 billion for Mint Mobile in 2023, you could hardly fault every celebrity for wanting what Reynolds had.
Suddenly being the face of Neutrogena, or even collecting millions for cracking open a Pepsi, didn’t sound quite so sexy. “All the celebrities [were] thinking, ‘Wait a second. I can make so much more doing this than I can in an endorsement,’” says Todd Shemarya, a veteran agent who advises some of the biggest stars in the world on endorsement deals and brand building, including Jennifer Aniston, Brad Pitt and Matthew McConaughey.
Almost a year ago, The Ankler wrote about the boom in celebrities launching companies, the agents fueling the move — and whether it was a bubble. Since then, reality has set in about how hard those Clooney and Reynolds-style 10-figure deals are to pull off. Although the pendulum hasn’t swung all the way back to the old days, the market has leveled.
Straight endorsement deals don’t sound so bad now — one dealmaker in the space even went as far as to tell me that there’s currently “rabid interest” in them — especially as there are fewer TV and film roles to come by.
As Hollywood talent grapples with less work on the horizon and brands are more interested than ever in leveraging celebrity, what does the landscape of commercial pacts look like right now for both performers and their agents and lawyers? How has the evolution of the marketplace changed deals? Where are the biggest opportunities — and what kind of payday can everyone expect?
“There’s not a ‘set it and forget it’ template to how these deals are made and formed anymore,” says Thai Randolph, interim CEO of Rock the Bells, LL Cool J’s hip-hop-centric platform, and the former CEO of Kevin Hart’s media company Hartbeat. She says now that talent has more data and insight into their reach, thanks in no small part to social media analytics, they’re asking to share in the upside in brand deals, and ultimately, where appropriate, co-found startups. “You see them moving down the spectrum from endorsement to equity and, in some cases, full-on enterprises.”
In addition to Randolph and Shemarya, I spoke with lawyers, agents and advisors including Carla Laur from CAA, Chris Chatham from Manatt and PLUS Capital founder Adam Lilling to create a guide to the modern era of commercial pacts.
In this issue, I’ll tell you:
The VC-backed sector practically begging for stars
When you should ask for cash and when you should ask for equity
Why actors are well suited to be entrepreneurs — but the market forces cooling this opportunity
Where actors vs. influencers now sit in terms of desirability — and how the screw turned back
How the “right” international endorsement helps talent land better deals with studios and streamers
Where being new to endorsement deals is a major asset
Which sectors still pay 7-figures for a traditional endorsement
Three “green flags” to look for in every deal
Why market saturation might not really matter
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