Ryan Reynolds Sold 2 Companies For $2 Billion – Now He's Investing In Clothing: 'Can't Be Good At Something Unless You're Willing To Be Bad'

Ryan Reynolds, the charismatic actor behind the beloved anti-hero Deadpool, has proven he’s not just a force to be reckoned with on screen. His recent business ventures have shown he’s equally adept at navigating the corporate world, even if he claims he’s winging it.

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Although he may be incredibly successful in his ventures, selling two companies for nearly $2 billion in four years, Reynolds insists he's not an entrepreneur. In an interview with the Wall Street Journal, Reynolds said, “I wouldn’t characterize myself as an entrepreneur. I would characterize myself as someone who has found a couple of different things in life that I believed in with every cell in my body, and this is one of them.” 

Reynolds’ journey into entrepreneurship began with his investment in Aviation American Gin in 2018. As spokesman and creative director, his witty marketing campaigns propelled the brand to become the second-largest super-premium gin in the U.S. In 2020, Diageo acquired Aviation Gin for up to $610 million, netting Reynolds a substantial payday.

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But it was his investment in Mint Mobile that really turned heads. In 2019, Reynolds acquired a 25% stake in the budget wireless provider. His involvement, which included starring in numerous advertising campaigns, helped skyrocket the company’s revenue by nearly 50,000% between 2017 and 2020. The payoff? T-Mobile acquired Mint Mobile for a staggering $1.35 billion, with the deal officially closing on May 1, 2024, after receiving regulatory approval.

Reynolds’ business acumen doesn’t stop there. He co-owns Wrexham AFC, a Welsh football club that has gained international attention. His advertising agency, Maximum Effort, continues to produce viral campaigns. And his latest venture, a partnership with clothing company Homage, has launched a “Threadpool” collection featuring Deadpool-inspired designs.

What’s the secret to his success? Reynolds attributes it to his willingness to learn and take risks. 

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In an interview with Entrepreneur’s Editor-in-Chief Jason Feifer, Reynolds shared, “I always say that you can’t be good at something unless you’re willing to be bad. And as I’ve gotten older, I’ve gotten way more comfortable with not having the answers.” He added, “I think it’s such a great tool of leadership to be able to say, ‘I don’t know.’ The worst leaders I’ve ever worked with or been around are the ones who are steadfast and indignant in their righteousness, and really worried about their image. So I love saying, ‘I don’t know.'”

Reynolds also believes in the power of constraints and problem-solving. “You’ve got to give yourself some guardrails,” he said. “Problems are our best friends, because they really inspire ideas and ways to create.”

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His latest venture, a partnership with the clothing company Homage, has launched the “Threadpool” collection, featuring a range of Deadpool-inspired designs. This collection includes 18 custom-designed T-shirts, each priced at $32, and it's already creating quite the buzz among fans.

As Reynolds continues to expand his business portfolio, he’s proving that a combination of star power, clever marketing, and a dash of self-deprecating humor can go a long way in the business world. Whether he’s cracking jokes on screen or in the boardroom, Ryan Reynolds is redefining what it means to be a Hollywood entrepreneur. The world eagerly anticipates what industry he’ll shake up next.

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