Ryan Reynolds Sold 2 Companies For Nearly $2 Billion In Less Than 4 Years But Has No Problem Admitting He Doesn't Have All The Answers — Loves Saying 'I Don't Know'

When you hear the name Ryan Reynolds, your first thought might be of the witty, irreverent actor who brought characters like Deadpool to life. But Reynolds is much more than an A-list celebrity; he's an entrepreneur whose business ventures have sold for a combined total of over $2 billion. 

How did this versatile actor go from Hollywood sets to the boardrooms of major corporations? The answer lies in his unique perspective on business, creativity and leadership.

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Reynolds has donned many hats. His 25% majority stake in fledgling Mint Mobile led to a substantial windfall when T-Mobile acquired the startup for $1.35 billion after just four years. Between 2017 and 2020, Mint Mobile's revenue increased by nearly 50,000%, with many subscribers signing up because of Reynolds, according to Fortune. 

This was not his first high-profile business venture. In 2020, he sold his Aviation American Gin brand to Diageo for $600 million after acquiring an ownership stake in 2018.

What is shocking is Reynolds' comfort level in navigating unfamiliar territory. "Does he know what he's doing? Not really! And he's not afraid to admit it," he said in an interview with Entrepreneur. "You can't be good at something unless you're willing to be bad."

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That statement encapsulates his approach to risk-taking. He understands that mastering a skill — whether acting or entrepreneurship — requires a willingness to make mistakes. This willingness to "be bad" at something before becoming proficient is an invaluable leadership trait, according to Reynolds.

Reynolds advocates for the power of admitting uncertainty, considering it an asset in leadership. He further explains: "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.'"

He also views problems not as obstacles but as opportunities for creative solutions. Challenges "really inspire ideas and ways to create," he said. This ethos of turning obstacles into stepping stones is evident in his venture Maximum Effort, an advertising agency known for producing viral ads for brands like Match, Mint Mobile and Aviation Gin. 

Advertising success is even more surprising considering how much Ryan once disliked marketing, seeing it as merely an obligation. His views changed dramatically when he spent a decade working to make "Deadpool" a reality against Hollywood skepticism. His experience with "Deadpool" reinforced another core belief: Limitations can inspire creativity. 

"Every time the studio took money away from our budget, we replaced whatever set piece we lost with character," Reynolds said. 

This focus on character over spectacle led "Deadpool" to become the highest-grossing R-rated movie of all time, reaffirming Reynolds' conviction that resource constraints can drive innovation.

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