How ‘Shark Tank’ Star Kevin O’Leary Uses His Mother’s Wisdom In Investing And Life

Kevin O’Leary has often recounted the story of how his mother influenced his investment philosophy. On his official website, the Shark Tank star says he inherited his “business intuition” from his mother. O’Leary once told Macleans that he discovered as the executor of her estate that she had preserved all of the wealth she’d earned.

“She had an investment philosophy that I didn’t appreciate then but I do now. She said, never invest in anything that doesn’t have yield.”

This week O’Leary told CNBC he has raised his children with the same bootstrapping credo as his mother, who was of modest means, did with him. His mother stopped giving him money after he graduated from college, comparing his lot in life to a bird who either learns how to fly or ends up dead under the nest.

O’Leary says his children are funded from birth to the end of college, but after that they’re on their own. But there were also some comparatively — for kids from wealthy families — “tough” times in the intervening years. On a trip to Europe when his son was 16 years old, O’Leary sat in first class while his offspring was roughing it in coach.

But even though O’Leary’s kids still grew up with privilege, he says he’s in favor of a traditional means of teaching children about responsibility and hard work: an allowance. That is, as long as it’s attached to labor.

“I’m in favor of allowance for children if they work for it, because then they equate the value of money to time worked. I’m not in favor of just giving the money as if it grows on trees — because it doesn’t.”

Even though O’Leary may have learned some important life lessons from his mother, he also participated in some deals that had questionable long-term value. Among them was his much-touted sale of The Learning Company to Mattel, a deal that the Shark Tank producers used to include on Mr. Wonderful’s bio during the opening credits.

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As Canadian Business reported in January 2017, when O’Leary was a candidate for leader of Canada’s federal Conservative party, back in 1998 Mattel made an offer to purchase TLC for $3.8 billion. After the deal went through, TLC posted losses that affected shareholder value. They filed a class action lawsuit against Mattel and other defendants, including O’Leary, and settled in 2003 for $122 million.

For O’Leary’s part, he told Macleans back in 2011 that he disputed accounts that Mattel was deceived by TLC or that the company wasn’t profitable before the merger, arguing the resulting litigation would have revealed such evidence.

If there’s something O’Leary apparently does well, it’s sell-off companies for a profit. He has been involved with two of the biggest exits in Shark Tank history: the sale of GrooveBook to Shutterfly for $14.5 million (as reported by Forbes in 2014) and the sale of meal delivery service Plated to Albertsons for $300 million (as reported by CNBC in 2017).

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O’Leary is all about the money on Shark Tank, which sometimes fails to endear him to viewers and contestants. But knowing it’s a lesson he learned from his mother, who was all about the value of hard work, makes his story a bit more compelling.

Shark Tank airs Sunday nights on ABC.

[Featured image by Aaron Davidson/Getty images]