In the premiere of Welcome to Wrexham, the Hulu docuseries chronicling Ryan Reynolds and Rob McElhenney’s purchase of a fifth-tier Welsh football club, the It’s Always Sunny in Philadelphia star does a bit about his partner’s various (and lucrative) business pursuits.
“I have TV money, but as I started to look at how expensive it actually was to run a club, I realized that I needed something more than TV money,” McElhenney said to the camera. “I needed movie star money. More than that, I needed superhero movie star money. More than that, probably, as we ascended up the leagues, I would need alcohol baron money and mobile phone services money.”
He pauses and asks someone off camera, with a laugh, “What other companies does this bitch have?”
It was funny, but it’s also true — Reynolds’ growing business empire is, perhaps, the ultimate example of how extremely successful Hollywood talent are increasingly turning their professional attention to non-acting endeavors.
Adam Lilling of PLUS Capital, which works with stars on start-ups and other ventures, says there are generally three major types of investments: Stars actually founding companies, which he says can mean life-changing money but are also high risk; sweat equity deals, which are less risky since they involve an existing brand, but can still bring in millions; and investments into an existing company that include equity in exchange for some deliverables, which are the least lucrative of the three, but also the least time-consuming.
“People who have made a lot of money in film, or TV, or sports are saying, ‘I don’t want to be a mascot. If you want to work with me, I want a part of the upside,’” says Lilling, whose firm has worked with more than 75 top-tier artists, athletes and cultural leaders on investing, joint ventures and launching businesses. Though, especially for already in-demand actors, it’s important not to go overboard with commitments. He says, “You can build one company, and maybe do one or two large sweat equity deals at a time.”
The Deadpool star has done it all. He has shaken up the industry with clever ads for his Aviation Gin brand — but he also made quite the stir when he sold it to Diageo in a deal worth as much as $610 million in 2020, just two years after buying in.
“We didn’t work with Ryan Reynolds but he is a great example of someone who joined an existing company and backed it at a level where he became a quasi-co-founder,” says Lilling. “Aviation Gin existed, it had distribution, it had a brand, and he took it to level 10. He bought in, with some level of cash and sweat, but dove in like it was his company. He took the product and made it ubiquitous.”
And it paid off. Notes another industry rep, “You see the numbers on the exit and everybody says ‘I want that deal.’”
Reynolds’ on-camera skill has translated into content marketing acumen that boosts all of his businesses. In 2021, he joined ad-tech giant MNTN as chief creative officer when it acquired Maximum Effort Marketing, which he founded in 2018 with George Dewey. Then, of course, he and McElhenney paid a reported $2.5 million for Wrexham AFC — which kicked off that Hulu series.
“In the past few years, more clients have seen the value in and are more excited to build companies and brands,” notes Endeavor SVP of Corporate Development and Talent Ventures Ben Enowitz. “In addition to promoting the product, they’re getting involved in product design, creative marketing, and business development. It not only diversifies their income streams, but it has been emotionally rewarding for them to explore their entrepreneurial passions across different consumer sectors.”
Another A-lister whose spirits brand is expected to give George Clooney a run for his Casamigos money is Dwayne Johnson. The Black Adam star took a very hands-on approach in launching his Teremana tequila brand in 2020, which could very well have him following in the footsteps of Clooney and co-founder Rande Gerber who sold Casamigos to Diageo for nearly $1 billion in 2017.
“When it comes to building a spirits brand, everybody comes to me saying ‘I want to build my Casamigos,’” says Lilling, adding that Johnson is a prime example of someone who could very well pull it off. “The Rock is in a good position,” he says. “I think he will exit with hundreds of millions of dollars or more from [Teremana] by the time it’s over.”
Johnson’s business interests are diversified too, starting with Seven Bucks Productions, which he started with business partner Dany Garcia in 2012. His other businesses and investments include an energy drink (Zoa), a multi-day wellness and entertainment event (Athleticon), a boutique ice cream shop (Salt & Straw), a clothing line (Project Rock with Under Armour) and the XFL, which Johnson, Garcia and RedBird Capital bought for $15 million in 2020. The no-longer-defunct football league begins its 2023 season in February, and recently announced a multiyear partnership with Ticketmaster.
Another question Lilling says he gets often is “How do I build Hello Sunshine?” The company co-founded by Reese Witherspoon in 2016 was valued at $900 million in a 2021 sale to Candle Media. The Morning Show star retained a stake and joined the board, along with Hello Sunshine CEO Sarah Harden.
“Reese is the epitome of a founder who has built a successful media company,” says Lilling, adding that it’s one of the “iconic exits that everybody is aspiring to.”
Witherspoon’s earlier venture, a Nashville-based clothing line Draper James, is still going strong too, and last year partnered with Kohl’s on a new capsule collection.
Chris Chatham of Manatt, who has been involved with Kristen Bell and Dax Shepard’s diaper start-up Hello Bello since day one, says established talent who aren’t exploring these kinds of ventures are leaving money on the table. Chatham also advised Next Century Spirits in its recently announced partnership with Seth MacFarlane for Bear Fight American Single Malt Whiskey. Under the deal, MacFarlane will serve as a brand stakeholder and act as its chief storyteller.
“This is the future,” he says. “The talent in our industry are now leading investors, entrepreneurs and moguls in other industries, and it’s fascinating to see how these well-known Hollywood figures are strengthening their brands with these types of deals. This is a structural shift in our industry that is growing exponentially.”
While experts say there has been saturation in certain markets, specifically alcohol and beauty brands, there’s still no shortage of opportunity for talent looking to expand their portfolios.
“There are different ways for artists to share their voice,” Joel Lubin and Maha Dakhil, co-heads of CAA’s motion picture group, tell THR. “Those who have platforms beyond acting are able to engage with their core audience and navigate the business overall in many different ways. However, we are conscious that artists are committed first and foremost to storytelling. We strategically advise them so that any other areas they are exploring as a means to express their creativity serve to support and enhance their primary passion and interests.”
And, the financial benefits of these ventures can also boost their creative careers. Stars diversifying their income streams lets them focus on acting projects they’re truly interested in, instead of worrying if they can afford to pass on any given opportunity.
“Once you’ve monetized it, there’s a ton of flexibility and discretion they would not have otherwise realized,” says Chatham. “They’re driven by the story rather than trying to figure out their livelihood. It’s a huge difference. There are very few people who have that luxury in our industry, but that number is growing because of these deals, no question.”
A version of this story first appeared in the Oct. 19 issue of The Hollywood Reporter magazine. Click here to subscribe.