Copyright Benzinga
Shark Tank investor Kevin O'Leary once shared how his mother's disciplined approach to investing shaped his own financial philosophy. Mr Wonderful Learned Wealth From His Mother During a June 2025 appearance on The Diary of a CEO podcast, O'Leary was asked about how to grow and maintain wealth. He credited his mother, Georgette, for teaching him the foundational principles he still follows today. "I learned this from my mother and I actually built a whole indexing company around it when I was very young," he said. Born in Montreal in 1954 to Lebanese and Irish parents, O'Leary described his mother as fiercely independent, determined never to let a man control her life. She started working in her father's company and got paid cash, O'Leary recalled, his voice emotional. She would take 20% of that money each week and put it into dividend-paying large-cap stocks and seven-year telecom bonds. "She never spent any of the principal, only the dividends and the interest," he said. See Also: Mr Wonderful Kevin O'Leary Says You're Literally Giving Away Money To Billers By Not Doing This One Simple Thing — And He's Been Doing It For Decades What Was Georgette O'Leary's 55-Year Secret Portfolio Georgette's disciplined investment rules were simple but powerful: never more than 5% in any single stock and no more than 20% in any sector. When a stock grew beyond 5%, she would sell it down. O'Leary said she kept her account secret from both her husbands, wanting her own independent money. After she passed, O'Leary saw the portfolio and realized it had outperformed most hedge funds over 55 years, he said. That's when he decided, "That's how I'm going to invest for the rest of my life." O'Leary's Lessons For Building Lasting Wealth The Shark Tank investor said that following his mother's rules can help anyone maintain and grow wealth. "People make big bets, thinking they're right and put half their net worth into one sector or stock — and they get wiped out. That's what happens," he said. He acknowledged that real estate makes up about a third of his net worth, slightly bending his mother's sector rule for strategic reasons. Subscribe to the Benzinga Tech Trends newsletter to get all the latest tech developments delivered to your inbox. From Middle-Class Roots To Financial Empire After earning an MBA from Western University's Ivey Business School, O'Leary co-founded educational software firm SoftKey, later selling it to Mattel for $4.2 billion. Since then, he has built a diversified empire, including television, investments and ventures like O'Leary Fine Wines. Today, he has a net worth of approximately $400 million. Check out more of Benzinga's Consumer Tech coverage by following this link. Read Next: Mark Cuban Dismisses Commerce Secretary Howard Lutnick’s Trade War Optimism: ‘Someone Needs To Explain…How Capitalism Works’ Photo courtesy: Kathy Hutchins / Shutterstock.com
