Kevin O'Leary Admits He's Had 'Some Catastrophic Failures,' But Says 'You Only Need One Win, And You Set Yourself Free'
Kevin O'Leary might be worth hundreds of millions today, but the investor and “Shark Tank” star says his success was built on some serious setbacks.
Failure, Then Freedom
In a recent post on X, O’Leary said he wouldn't change anything about his past, not even the parts that went terribly wrong.
“I wouldn’t have changed anything. I wouldn’t give him advice to do anything other than what he did, because it was the failures that led to the successes,” he said when asked what he would tell his 25-year-old self.
I wouldn't have changed anything. I wouldn't give him advice to do anything other than what he did, because it was the failures that led to the successes. I had some catastrophic failures, but I recovered from them. You only need one win, and you set yourself free. It's not about… pic.twitter.com/3PykswrsHW
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O’Leary added, “I had some catastrophic failures, but I recovered from them. You only need one win, and you set yourself free.”
To him, it's not about chasing dollars, but “the pursuit of freedom.” That freedom, he explained, means waking up and choosing what to work on. “I don't have to be here. I want to be here.”
After selling his company Softkey for $4.2 billion in his mid-30s, O'Leary did what many dream of: he retired. For three years, he traveled the world and visited every beach he could find. “I thought, ‘Hey, I’m 36, I can retire now,'” he recalled on CNBC six years ago.
But it didn't take long before the boredom set in. “It was really boring,” he admitted.
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He soon realized that money alone doesn't provide lasting purpose. According to him, work isn’t just about money. It gives you purpose, and it’s social. You stay mentally active by engaging with others, thinking critically, and tackling challenges.
He eventually returned to the business world, but this time as an investor rather than an operator. What drew him back was the thrill of taking risks, competing, and building things. “I like competing. I love being in the race,” he said.
These reflections put O’Leary at odds with the financial independence, retire early movement. He believes early retirement often results in people becoming isolated and losing their edge. “Staying stimulated is how people live into their 90s.”
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