Kevin O'Leary Split From His Wife for 2 Years, Lived 'Every Bachelor's Dream Times 10' — Then Learned People's True Motives If You're a 'Rich Guy'

Some midlife detours come with a sports car. This one came with a yacht, a villa in the south of France and a marriage headed for divorce.

“Shark Tank” investor Kevin O’Leary says sudden fame sent him down that road, and it took two years and a sharp message from his daughter to find the way back.

“That was nuts what happened,” O’Leary said on “The Fifth Column” podcast last December. “And, you know, I just wasn’t used to it. I obviously let it get to my head and it was bad.”

“And so, you know, I got kicked out of my house and I lived by myself for two years and I had a crazy, crazy time,” he continued.

O’Leary and his wife, Linda, married in 1990 and separated in 2011.

The Yacht Life Came Up Empty

“I lived every bachelor’s dream times 10,” O’Leary said. “I had a villa in the south of France. I had a yacht. I had all that stuff. It was crazy. But it was hollow and shallow.”

He said the wealth also made it hard to trust the people around him.

“I’m glad I didn’t stay down that path because the motivations of the people around you aren’t necessarily true,” O’Leary said. “I mean so this is also one of the bad things about being a rich guy.”

It isn’t the first time he’s found the high life overrated. He’s described how exploring every beach on Earth after he first got rich eventually got boring.

His Daughter Called A Time-Out

O’Leary said Linda also met someone else during the split.

“So we were living separate lives and we weren’t divorced yet, but we were going through the process,” he said.

Then their daughter stepped in. According to O’Leary, she asked them, “What are you [expletive] doing? Destroying our family.”

“So we got back together and it was actually [a] better union after that,” O’Leary said. “And I’m very proud that our family is back together because it’s a very tough time.”

Now He’s The Friend With Marriage Advice

O’Leary said he now helps friends going through their own marriage failures. He’s long argued that financial stress, not infidelity, is what sinks most marriages, and he’s told spouses they can share a credit card but should keep their savings separate.

Not every friend takes the advice. O’Leary said he has been to all four of one friend’s weddings and finally told him, “It’s not them. It’s you.” When he asked why the man kept getting married, O’Leary said the friend’s answer was, “I miss the cheating.”

His own rule is simpler.

“That’s the other thing I learned. Don’t move in unless you get married,” O’Leary said. “You have no reason to stay together. The first problem you have, you just split up again. It’s stupid.”

More Americans seem to be sticking with “I do.” The U.S. marriage rate rose to 6.3 per 1,000 people in 2024, while the divorce rate slipped to 2.3, according to Centers for Disease Control and Prevention data.

A yacht can hold a lot of people. Apparently, not always the right ones.

O’Leary said he did “unbelievably crazy stuff” during those 2 years. “And I think back on it I think, wow, did I really do that? The answer is yes,” he said. “But I don’t want to go back there and I’m very, very happy.”

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