'It Was Boring' – Kevin O'Leary Explored Every Beach On Earth After He First Got Rich, But The Highs And Lows Of Investing Brought Him Back

When Kevin O’Leary, aka "Mr. Wonderful" from Shark Tank, sold his first company, Softkey, for $4.2 billion, he thought he was set for life. In his mid-30s at the time, Kevin decided to retire and live the dream most of us have – complete financial freedom. But what did he do with that newfound wealth? He took off to explore the world.

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"I thought, ‘Hey, I'm 36, I can retire now,'" Kevin recalls. And that's exactly what he did. He took off, exploring the most beautiful beaches and locations on Earth. "I went to every beach on Earth," he says. But after three years of retirement, something unexpected happened: "It was really boring."

He realized work wasn't just about money. It gives you purpose, and it's social. You're interacting with people, thinking, and solving problems. It keeps you sharp.

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After a while, Kevin felt the pull back into the game. He missed the highs and lows of building something, taking risks, and investing in businesses. He soon transitioned from running a company to becoming an investor. 

"I like competing. I love being in the race,” he says. That's really what brought him back – being part of something bigger.

Over the years, Kevin's straightforward, sometimes brutally honest, approach to investing has made him a polarizing figure. "Does that make people unhappy? Oh yeah," he says with a grin. "But I just tell the truth."

This revelation put Kevin at odds with the popular F.I.R.E. (Financial Independence, Retire Early) movement, which encourages people to save aggressively, invest wisely, and retire in their 30s or 40s. For Kevin, the idea of retiring early didn't match reality.

"This whole idea of Financial Independence, Retire Early doesn't work," he says. People think, 'I'm going to retire early and life will be perfect,' but they're wrong. He says that work keeps you engaged. Staying stimulated is how people live into their 90s. It's how they stay sharp and healthy.

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Kevin's experience taught him that true happiness isn't in financial freedom alone. While being wealthy allowed him to retire, it didn't bring fulfillment. He has seen people retire, drift away, become isolated, and lose their sense of purpose. 

After exploring the world, he decided to get back in the game. But this time, instead of running a company, Kevin became an investor, using his business expertise to help others grow their ventures.

Kevin believes that you will fail if you're not passionate about what you're doing. You must love what you're doing so much that you're willing to do the work. The money will follow. But it's not about the money – it's about being free to pursue what you love.

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