"I was really in a bad shape" — When Shark Tank Kevin O'Leary explained how hardship influenced his family's financial safety net

Shark Tank investor and businessman Kevin O’Leary once described the financial challenges he faced after graduating college. He spoke about how that experience shaped his approach to generational wealth during an interview on Behind the Brand with Bryan Elliott on May 24, 2019.

Host Elliott asked O’Leary about his stance on inheritance, referencing how some billionaires, like Bill Gates and Warren Buffett, have chosen not to leave large sums to their children. In response, O’Leary explained that after completing college, his mother stopped supporting him economically, which led to a difficult period. He recalled:

"It was a very traumatic couple of years after that trying to find my way and I had no money and I was really in a bad bad shape."

This experience influenced how he structured his own family’s financial trust, ensuring his children receive support only up to their college graduation.

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Shark Tank Kevin O’Leary’s approach to financial independence and generational wealth

Establishing a financial trust based on personal experience

Kevin O’Leary explained that his mother covered his expenses until he finished college, but after that, he was responsible for himself. He recounted his mother's belief that financial independence is essential, saying:

"She said the dead bird under the nest never learns how to fly."

Although he struggled in the years following graduation, he credited this period with teaching him money management and responsibility. This principle became the foundation of his family trust. When O’Leary sold The Learning Company, he formalized a structure ensuring that future generations in his family would have monetary support only up to their last day of college. He stated:

"It’s a full freight pay from birth to last day of college and then they get this—nothing."

The Shark Tank investor stressed that the arrangement was designed to provide educational opportunities while still encouraging self-sufficiency.

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His son’s reaction and the impact of the trust

Kevin O’Leary shared an instance when his son, Trevor, questioned the structure of the trust while struggling academically in high school. According to O’Leary, his son asked for clarification on how the trust worked.

In response, O’Leary explained that the trust would cover him until high school graduation but that beyond college, he would receive no monetary assistance. He mentioned:

"'You're on your own. You get nothing.'"

O’Leary added that this conversation had a significant impact on his son’s approach to education. The Shark Tank investor recalled telling Trevor:

"'Why don’t you take advantage of the runway you’ve got?'"

Following this discussion, his son improved his academic performance and later pursued a degree in electrical engineering. O’Leary suggested that the understanding of financial responsibility helped shape his son’s career path.

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Financial responsibility and future generations

Kevin O’Leary emphasized that while the trust ensures support for education, it does not provide for a lifetime of wealth. He indicated that future generations would have similar structures in place. He noted:

"That money will sit in trust and just roll on long after I’m gone to do whatever it does,"

The Shark Tank investor also stated that if his children want to start a business, they would not receive financial assistance from him directly. Instead, he told them:

"'I’m expensive. I want a royalty.'"

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