On the left, Kevin O’Leary tears up, on the right a young Kevin O’Leary poses with his mother
Kevin O’Leary, best known as one of the outspoken investors on the popular show Shark Tank, recently got emotional while sharing the quiet investment strategy his late mother followed for decades on an episode (1) The Diary of a CEO podcast
His mother, Georgette Bookalam, wasn’t an investment banker. She worked at Kiddies Togs (2), a clothing manufacturer in Montreal, while raising her two boys. But behind the scenes, she quietly amassed a small fortune—one she kept hidden from both her husband and her kids. O’Leary says he didn’t realize how much she’d saved until after she passed.
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Over time, her disciplined approach paid off. Her investments helped her put both sons through college and allowed her to support family when they hit rough times.
According to O’Leary, his mom’s strategy was fairly simple:
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Invest what you can (ideally 20-30% of your income)
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Focus on dividend-paying stocks and bonds
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Never spend the principle, only the income it generates
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No more than 5% in a single investment and no more than 20% in one sector
“She’d take 20% of that cash each week and she would put it into two asset classes: stocks that paid dividends, large cap stocks, and teleco bonds” he told podcast host Steven Bartlett (3).
He added that her rules were unwavering: “No more than 5% in any one stock or bond… and no more than 20% in any one sector. Ever. When a stock ran up past 5, she’d sell it down. This is not genius — it’s just diversification.”
Why does Georgette’s strategy work?
At its core, this strategy works because it leans on basic investing principles: consistency, income-generation and risk management.
First, investing a fixed percentage of income, especially as high as 20%, creates momentum. Over decades, that kind of discipline allows compounding to do the heavy lifting, even without chasing high-risk opportunities.
By focusing on dividend-paying investments, she created a steady stream of income. Instead of selling assets when she needed funds, Georgette’s portfolio paid her regularly. Her rule about never touching the principal ensured that the income stream could continue indefinitely.
Finally, diversification helps protect her from major losses. By limiting how much she invested in any one stock or sector, she reduced the risk that one downturn could derail her entire portfolio. According to O’Leary, that strategy was highly effective — and it’s still one he uses today. (4)
“She caught the market then some…I designed the whole platform around Georgette’s philosophy, and that’s the only thing I buy for my family trust.”
Read More: Almost 50 with no retirement savings? Here’s why you shouldn’t panic
How to use this O’leary’s mom’s strategy for yourself
You don’t need decades of investment experience to apply the same principles today. The strategy can be adapted in a much simpler, more accessible way.
Start with consistency: Set a target amount to invest every month, even if it’s less than 20%, and invest regularly. Automating contributions to a retirement or brokerage account can make this effortless — just remember to go in and invest the funds regularly.
Instead of picking individual stocks, consider broad market funds that provide instant diversification, helping you follow her “5% rule” without constant monitoring. Many also include dividend-paying companies, giving you exposure to income-generating assets. If income is your goal, you can also look for dividend-focused ETFs that bundle together companies known for paying reliable dividends.
The “never spend the principal” rule might require a mindset shift: treat your investments as long-term assets, not short-term cash. If you do need income, try to rely on dividends or interest rather than selling investments during market dips.
And finally, start as early as possible. Georgette’s biggest advantage wasn’t timing the market, it was time in years in the market—55 years, according to O’Leary. Small, consistent investments can grow significantly over decades.
The takeaway: you don’t need a complex strategy to build real wealth. Consistently investing in diversified funds, and leaving them alone, can be far more effective than trying to time the market or chase the next winning stock.
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YouTube (1),(3); O’Leary for Canada (2); LinkedIn (4)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
