Shark Tank investor Kevin O'Leary has recalled how stripping his son of financial safety nets pushed him to excel academically, sharing the tough-love lesson that propelled him to Harvard.
O'Leary Says Entitlement ‘Ruins Ambition'
Earlier this week, O'Leary posted a video on social media recounting a conversation with his son, Trevor, about family wealth and trust funds.
"My son asked me about his trust fund. I told him it ends when school does. No grades, no cash," O'Leary said. "The look on his face was horror."
"That's when I hit him with the line my mother gave me: ‘The dead bird under the nest never learns to fly.'"
O'Leary, who has a net worth of $400 million according to Celebrity Net Worth, said the fear of financial independence motivated Trevor to turn his grades around and gain admission to Harvard University.
"Entitlement ruins ambition. I ripped it out early," he added.
The No Free Lunch Parenting Philosophy
In the video he shared, O'Leary recalled telling his teenage son that his trust only covered schooling costs and would vanish after high school.
"He has plenty of friends that are totally screwed up. They don’t have any reason to launch. They’re totally covered by their family’s wealth. It's a curse."
From Montreal Roots To Business Mogul
Born in Montreal in 1954 to Lebanese and Irish parents, O'Leary credits his own mother with instilling discipline early on.
After earning an MBA from Western University's Ivey Business School, he co-founded educational software firm SoftKey, later selling it to Mattel for $4.2 billion in 1999.
Since then, O'Leary has built an empire through investments, television, and ventures like O'Leary Fine Wines, gaining notoriety for his blunt advice on Shark Tank.
Shaq Says Kids Need 3 Degrees To Access His Fortune
NBA legend Shaquille O'Neal, worth an estimated $500 million, has also made it clear his children won't inherit his wealth without earning it. He insists they pursue education and build their own careers before accessing any of his fortune, famously stating, "We're not rich, I'm rich."
In a 2022 podcast, Shaq explained that his six kids must obtain three college degrees to qualify for an inheritance. He wants them to value hard work, not grow up entitled.
Proud of his daughter Taahirah's success as a marketing director at Pepsi, Shaq hopes his other children will follow similar paths of independence and achievement.
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Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.
Photo courtesy: Kathy Hutchins / Shutterstock.com
