The art of the celebrity ad deal

It was a summer of celebrity brand deals in the spotlight: KATSEYE x Gap, Gavin Casalegno x Dunkin’, and of course, Sydney Sweeney x American Eagle.

They were buzzy, costly, and omnipresent. Though a celebrity-fronted campaign might be common, Keith Gelman, founder of entertainment marketing agency Talent Partnership Advisors, said that they don’t come without expense and consideration—the AE-Sweeney partnership, for example, was the brand’s biggest investment in a campaign to date.

And the difference between a brand paying top dollar for talent and being able to save some cash? Gelman said that often, it’s simply knowing that it might be a possibility.

“I’d see brands come into the picture and want to work with an artist, and they would spend a million dollars one day, and then the next brand would come in and spend $3 million with the same artist,” Gelman told Marketing Brew. “I always felt that there was like an inequity there that needed to be balanced.”

Over the years, he’s narrowed down what it takes to broker what he calls “the best deal.” Gelman founded TPA after spending eight years at Live Nation, where he was a lead in the global partnerships division and observed the intricacies of how celebrity-brand relationships worked, particularly how each navigated the others’ differing priorities. He’s found disconnect when a celebrity might not understand what an ad campaign is asking of them, or when a brand might request more celebrity assets than necessary, and he’s made it his job to navigate these discrepancies in the interest of the brand.

Time is money

Gelman said his approach takes a “10,000-foot view,” and he takes stock of all the different parties and goals involved in a campaign. From there, he said he considers, “How can we input a celebrity to maximize and work across as many different verticals as possible, because you have a finite budget and talent only has finite time?”

Timing is key to a well-struck celebrity ad deal. Gelman explained that while brands often work with longer lead times, celebrity talent can be tied to busy or unpredictable schedules, and that’s where he says industry knowledge and preemptive research are paramount.

“When we’re looking at talent with lead time, we need to look into a variety of factors, [including] where the trajectory of their career is,” he said.

One way to strategize for a campaign’s timeline while offering tangible benefits to talent—like exposure and impact—is looking ahead to potential milestones, like a band’s 25th anniversary, Gelman said. If the brand identifies an opportunity like this early on and gets involved, their campaign can become part of “something that’s truly 360,” especially if the talent continues to activate around the milestone moment.

Getting a brand into a celebrity’s world early also helps build the relationship, which can have long-term brand benefits down the line.

“Once we start getting into the nitty-gritty for the actual activation, we find a lot of times the talent is more ready to play with the brand, to explore them,” Gelman said. This way, when the brand needs more from the celebrity, he said they can be more likely to say yes to things like staying later, doing an extra interview, or tagging the product in social posts.

This is real, this is me

At the core of a successful celebrity brand deal is a word that marketers can’t seem to escape: authenticity.

While brands seek measurable results, Gelman said celebrity talent is often seeking an outlet for “authenticity and creative expression.” Sometimes, each side can get lost in their own sauce, and Gelman finds himself needing to step in to explain and simplify what both brand and celebrity can do to enhance each other’s goals.

Though it can seem simple, taking the most authentic approach to celebrity relationships still isn’t quite par for the course, according to Gelman.

“Some brands still adopt generic strategies without tailoring campaigns to specific talent,” he said. While taking a broader approach might work for short-term partnerships and pop-up activations, Gelman believes longer-term campaigns and relationships will continue to trend and require bespoke approaches.

“It’s not as simple as find a talent, book a talent, have the talent show up in the campaign,” Gelman said. “Every last piece of the puzzle needs to be worked out ahead of time.”

Update 09/30/25: This story has been updated to clarify Keith Gelman’s job responsibilities at Live Nation.