Kevin O’Leary has always been a man of many words. He recently shared on X that he has no regrets about his past. Even the moments that went badly.
When someone asked our beloved Mr. Wonderful about advice he’d give his 25-year-old self, he said he wouldn’t change a thing. O’Leary explained that every mistake and setback played a role in shaping his later success.
To him, those failures were necessary steps in learning and building the career he has today.
Kevin O’Leary On How One Victory Can Outweigh Every Failure
Mr. Wonderful then went on to explain that he was also no different than your average Joe when starting out. He said, “I had some catastrophic failures, but I recovered from them. You only need one win, and you set yourself free.”
O’Leary said what drives him isn’t money but the freedom to live life on his own terms. In Leary-land, success means having the choice to decide how to spend his day working and what projects to work on. Or as Kevin puts it, he doesn’t work because he has to, but because he wants to.
That philosophy of viewing every setback as a setup for one defining win is something O’Leary often returns to.
Early Retirement and the Reality Check
When Kevin sold his company, Softkey, for $4.2 billion in his mid-thirties, he decided to step away from work completely. He spent the next three years traveling the world, hopping from one beach to another, convinced he had earned an early retirement.
“Hey, I’m 36, I can retire now,” he once told CNBC. But the novelty and excitement wore off faster than he expected. And the sad realization of the fact that life without purpose wasn’t all that it was made out to be crept in. Kevin admitted that “It was really boring.”
It didn’t take long for Mr. Wonderful to see that money by itself doesn’t bring real fulfillment. He said that work is about much more than earning an income. Working also gives people a sense of direction and keeps them connected to others. The brain engagement, critical analysis, and everything that comes with it keep your wits intact.
After a while, he jumped back into business, this time focusing on investing instead of managing a company. What motivated him wasn’t the paycheck but the excitement of risk, strategy, and achievement. “I like competing. I love being in the race,” he said.
O’Leary’s Take on the FIRE Movement
The idea of retiring young doesn’t appeal to O’Leary for long. His perspective goes against the FIRE movement, which encourages people to quit working as early as they can.
The Shark Tank investor believes that leaving the workforce too soon can lead to isolation and a loss of drive. “Staying stimulated is how people live into their 90s,” he said. Kevin’s moral of the story was that having something to work toward keeps life interesting.
When asked about his retirement plans, Kevin replied with his classic wit by saying, “I don’t know where I’m going after I’m dead, but I’ll be working when I get there too.”
Focus on Health and Longevity
Since his priorities have reset, Kevin’s focus has shifted from maximizing wealth to maximizing time.
O’Leary says his schedule is fuller than it’s ever been, but he only takes on work that feels meaningful. Lately, he’s been putting a lot of energy into his health and longevity. “If there’s anything I want, it’s more time,” he tweeted on X. That mindset has made him serious about diet and fitness as he intends “to stay sharp right to the end.”
The New Meaning of Success for Kevin O’Leary
Kevin O’Leary has built a life that runs on curiosity, purpose, and profit. The big silver lining revelation here is that freedom doesn’t come from walking away from work, but from choosing the kind of work that keeps you alive inside.
These days, since time is money, wealth isn’t measured in dollars but in time. Work isn’t a burden for Mr. Wonderful; instead, he looks at it like a puzzle that keeps him sharp and connected.
As someone who has “made it” in life, Kevin is just chasing more time to keep doing what he loves. And that might be the smartest investment he’s ever made.
