Kevin O'Leary Reveals the Brutal Rule He Used to Motivate His Son — Lesson for Parents Everywhere

Kevin O'Leary is one of the wealthiest individuals in the world, but his path to success was not easy. He has previously revealed how he was cut off by his mother at an early age, a moment that served as an awakening and pushed him to start earning his own keep.

Looking at where he is today, there is no doubt that his mother's approach was part of his success. He studied and worked hard, leading to his riches. As of this writing, Mr. Wonderful has an estimated net worth of $150 million, according to Celebrity Net Worth.

Now, it is O'Leary's turn to pass that philosophy on to his own children. Despite his wealth, the Canadian businessman does not want his offspring to be entirely reliant on him and instead wants them to adopt the same discipline and drive he had on his path to success.

O'Leary shared how he purposely cut off his kids after college. This means that after attaining a degree, it would be up to his kids to figure out their next step.

'I set up a trust. It does not provide to anybody anything after they finish education,' O'Leary shared.

He went on to explain that, as a parent, he covered educational expenses to ensure his children had the best possible start. However, aware that some children may take education for granted, he introduced conditions to ensure they remain accountable.

'From birth to the last day of education, full free ride. Everything paid for but if you drop out of school or you don't make it to college, you're cut off,' he added.

Misery Now, Luxury Later

One of his kids, Trevor O'Leary learned this the hard way. The Shark Tank star shared a conversation between them when Trevor was still a teenager.

The elder O'Leary admitted that Trevor wasn't exactly bright in high school. Kevin urged his son to do better and the response he got was far from reasonable.

'My son was doing really poorly in high school,' the Canadian businessman recalled. 'He said, "Yeah, but I don't have to worry about it. I got a trust". I said no, if you only make it through high school, I'm dead and you're broke.'

It was at that point Trevor realised he needed to push himself and figure out a way to make it to college. O'Leary shared how his son exerted more effort in improving his grades and getting into college.

'He got his marks up, became an engineer, worked for Tesla and got into both Harvard and MIT,' the 71-year-old millionaire shared.

Tough Love That Works

Depending on how one raises their kids, the parenting strategy of O'Leary may or may not make sense. That depends on the culture and practices of parents, something that varies per ethnicity.

Given his wealth, O'Leary could have opted to give his kids an easy life, giving in to their demands and vices for a worry-free life. However, an offshoot from this is that ambition or drive may take a back seat, one that clearly goes against the principles that made him into the person he is today.

'Entitlement ruins ambition. I ripped it out early,' O'Leary shared.

With his approach, O'Leary admits that he may not have been the best dad in the world. But aware that he won't always be around to provide the necessary financial assistance his kids would get, the best recourse is to pass on to them how to make their own fortune using his matrix.

O'Leary's philosophy could also be a model that Canadian families may want to consider.

According to a 2024 survey by the TD Bank Group, roughly 3 out of 5 (57%) parents expect to financially support their kids when they reach adulthood. Additionally, two-thirds of those are wary of being able to meet that due to a variety of reasons such as the changing cost of living per Yahoo Finance.

In general, parents need to draw a fine line between loving and looking out for their kids' future. It is not bad to pamper or give in to their demands. However, it would be best to control this to a certain degree and incrementally teach them that wealth is something earned, not given.

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