“Tough couple of years”- When Shark Tank star Kevin O’Leary shared the piece of advice that changed his life

Shark Tank star Kevin O’Leary, widely known as “Mr. Wonderful,” shared a life lesson that shaped his path to success during his appearance on Logan Paul's Impaulsive podcast. After posting a discussion clip on his YouTube channel on July 6, 2024, O’Leary reflected on a pivotal moment from his college days.

He mentioned that his mother had given him life-changing advice after he graduated. As she cut off his financial support, she told him,

“The dead bird under the nest never learns how to fly.”

This moment marked the beginning of what O’Leary described as,

"I had a tough couple of years. I mean, I couldn't even pay the rent."

However, eventually, the Shark Tank investor found the motivation to succeed. The moment influenced how O’Leary later structured financial arrangements for his own children, ensuring they would only receive support until they completed college.

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Shark Tank star Kevin O’Leary’s approach

Shark Tank investor Kevin O’Leary recalled his mother’s tough-love approach as a defining moment in his life. When he graduated from college, she made it clear that her financial support was ending. O’Leary explained,

“She said, ‘No more checks. I’m not writing any more checks. You’re paying for your education. I paid for your birth. The last day of college, we’re done.’”

At the time, O’Leary had no job or means to support himself, describing those initial years as tough. However, he credited this experience for motivating him to build his career. When his business, The Learning Company, was sold for $4.2 billion, O’Leary was determined to instill the same values in his children.

After the sale of his business, Shark Tank star O’Leary set up a trust fund for his children. However, he ensured that it only supported them until they finished college, after which they would receive no further financial aid. Drawing from his mother’s philosophy, he emphasized the importance of not entitling them. He explained,

“The trust pays for everything until they finish college, and then they get nothing.”

Shark Tank investor O’Leary recalled a critical moment when his son, Trevor, who was struggling in high school, asked about the trust fund. In response, O’Leary reiterated that it would only support him until he graduated college, pushing him to take his academics seriously. According to O’Leary, this conversation was a turning point for his son. He stated,

"And I think at that moment that the lesson of life, you know, given to me by my mother must, he saw the abyss, he saw the darkness, he saw the situation he was in and went, sh*t, this is bad"

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Trevor O’Leary’s journey to success

Trevor turned his academic performance around. He pursued electrical engineering and excelled in his field. While at McGill University, Trevor became the captain of a team that built Formula 1-style race cars, competing against top universities like MIT.

Trevor’s team achieved a significant milestone by beating MIT in a global competition, thanks to software he developed to optimize battery energy release. This accomplishment caught the attention of Tesla, which offered jobs to the entire team. The Shark Tank star said,

"And so the Tesla guys came over and said, 'who are you guys?' And he went to college in McGill. He said, 'we're the McGill team.' And he said, 'you're all hired at Tesla, all of you, the whole team.' That's where he works. That's where he lives in San Francisco."

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Shark Tank airs every Friday at 8/7c on ABC.