Ryan Reynolds never set out to be one of Hollywood’s most bankable venture capitalists. As the story goes, the actor made his first big investment play buying ownership interest in Aviation Gin in 2018, after he tried the product and it was just that good. Celebrity-backed booze brands are as common as celebrity Ozempic prescriptions, but the difference is that Reynolds didn’t just put his face on the product—he also rolled up the sleeves of his superhero suit and got involved. Taking charge of Aviation’s branding efforts, he produced cheeky, self-deprecating ads that put an unknown alcohol brand on the map (i.e., trending on Twitter) and drove profits up by 100 per cent the following year. In a spot explaining why his product tastes so darn good, a familiar voice explains, “The citrus fruits are misted using only the tears of Aviation’s owner: me, Ryan Reynolds.” Make that the former owner. He sold Aviation to the U.K. booze baron Diageo for US$610 million in 2020, but the new owners have kept him on as a brand ambassador. Like Reynolds, they know a good investment when they see it.
And yes, we’re talking about that Ryan Reynolds. The Vancouver-born actor once best known for his plasticine face and teflon pecs has spent the last few years accumulating an investment portfolio more impressive than his IMDb page—which is really saying something since Deadpool, the anti-Marvel Marvel franchise that Reynolds stars in and co-produces, is among the most successful movie brands of all time. And Reynolds is one of the only reasons it got made. 20th Century Fox only agreed to finance it after his DIY and entirely NSFW teaser went viral. He later oversaw the movie’s unconventional marketing efforts: an expletive-laced endorsement from Betty White and an appearance at the 2016 Super Bowl, where Reynolds served chimichangas (Deadpool’s favourite food) out of a food truck.
In 2018, he co-founded Maximum Effort, a production company specializing in the same sort of scrappy, internet-sticky content that had propelled Deadpool to the top of the box office. (The Aviation Gin ad was among its first projects.) He repeated the process the following year, buying into Mint Mobile, a little-known discount telecom company whose revenue increased by 50,000 per cent under its new owner. Again, formerly speaking. Reynolds sold Mint to T-Mobile for $1.35 billion in 2023. He has landed on a winning strategy. After starting in the sexy world of alcohol, he has shifted his investments toward companies that might seem social-media retardant—1Password (a Toronto-based cybersecurity startup), Nuvei (a Quebec payment solutions firm), Wrexham AFC (a British football club), Titan Caskets (a Boston company that is exactly what it sounds like)—and created the kind of consumer enthusiasm usually reserved for the newest flavour of White Claw. His net worth is around $350 million.
What did Reynolds know about fintech? Or cryptography? Or British football? Not much. But he understood the power of relationships. “When you create emotional investment, you not only create affinity, but also resilience for a brand that can help you through ups and downs,” he told Mad Money’s Jim Cramer after the sale of Mint Mobile. It’s all just storytelling, whether it’s a feature film or a 30-second YouTube spot or his own Instagram account (over 51 million sets of eyeballs that will believe in any product he does).
Reynolds’s perfectly calibrated personal brand is the driving force behind everything: the aw shucks family guy whose punchlines focus on pants-crapping, the wide-eyed Vancouver boy with Silicon Valley savvy, a khakis-wearing everyman whose spouse was just at the Super Bowl with Taylor Swift. “Has anyone seen my wife?” he posted on Instagram as Blake Lively sat side by side with Swift, a good example of the kind of self-referential wink that underpins so much of Reynolds’s best content.
In the age of authenticity, he understands that there’s nothing authentic about the life he’s landed in. So why not lean in? His 2019 commercial for a new Samsung flatscreen was also a trailer for his new movie, Six Underground, which paused halfway through to run an Aviator Gin ad. The Wrexham football team wore their Aviator Gin kits in an ad for 1Password (which is also a Wrexham team sponsor). An Instagram post promoting the new Deadpool & Wolverine movie trailer featured Taylor Swift–style friendship bracelets emblazoned with the names of the two Marvel tough guys. Get it? Reynolds does. And now millions of Swifties are obsessing over the possibility of a Taylor cameo in the new movie. A bunch of marketing wonks might use terms like synergy or brand alignment. But Reynolds is just a guy who invests in brands that he believes in. As long as the world stays invested in him, it’s a winning strategy.
This story appears in the May issue of Maclean’s. You can buy the issue here or subscribe to the magazine here.
