Ice cream, dyslexia and mom: Kevin O’Leary’s journey

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Former Dragons’ Den and current Shark Tank TV personality and Canadian businessman Kevin O’Leary, whose businesses and investments have netted him millions, has a background as varied as his investments.

He is now known for his wealth and success, but he overcame several challenges to get there.

His father died when he was young, he was diagnosed with dyslexia, his stepfather, George Kanawaty, worked with the United Nation’s International Labour Organization, which meant the family moved around the world.

But with his mother an unusual entrepreneurial and investing inspiration, and an ice cream store owner another, very different one, O’Leary ended up the investor, business leader and tough-guy television personality that earned him the tongue-in-cheek nickname “Mr. Wonderful.”

O’Leary was born in Montreal of Irish-Lebanese descent. After undergraduate studies at the University of Waterloo in 1977 he obtained an MBA from the Ivey Business School at the University of Western Ontario in 1980.

With two of his former MBA classmates, O’Leary co-founded private TV production business Special Event Television.

After selling his share of the company, O’Leary co-founded Softkey, a publisher and distributor of CD-based personal computer software for Windows and Macintosh computers. They acquired other businesses and became a consolidator of educational software, eventually buying and changing the firm’s name to The Learning Company (TLC).

In 1999, Mattel bought TLC for US$4.2 billion.

Through his role as a venture capitalist on reality TV shows, CBC’s Dragons’ Den and ABC’s Shark Tank, O’Leary has invested in a number of startups, and created a holding company, Something Wonderful, to oversee them. He also invested in storage company StorageNow Holdings, earning more than $4 million on the sale of his shares, and co-founded mutual fund firm O’Leary Funds, which, after some controversy, was sold to Canoe Financial.

O’Leary also founded O’Leary Ventures, O’Leary Mortgages and O’Leary Fine Wines. In 2015, he launched an ETF through O’Shares Investments, and in 2021, took an ownership stake in FTX, the ill-fated firm of convicted fraudster Sam Bankman-Fried.

He has written several books on business, money and family. And in 2017 he campaigned to be leader of the Conservative Party of Canada. He is now about to launch a watch insurance venture.

Here, O’Leary shares how he used his dyslexia as his superpower, his memory of the one and only day he was someone else’s employee, and how his mother surprised the whole family with her sharp financial acumen after her death.

Tell us about some significant aspects of your early years.

“I’m the product of immigrants – an Irish father and my mother was Lebanese. My mother’s father formed a company called Kiddie Togs in Montreal, and that became the family business. The head of sales was my father, Terry O’Leary, which is how he met my mother, Georgette.

Unfortunately, Terry died when I was seven, so these are short-lived experiences. But during that period in Montreal, I developed severe dyslexia.

Dr. Sam Rabinovitch and Margie Golick [psychologists at the Montreal Children’s Hospital, and pioneers in dyslexia research at McGill] were doing very experimental research at McGill. I was in that cohort, where they did advanced therapy on dyslexics, and I give them all the credit for my [eventual] outcome.

Their whole method was to say, ‘You can’t read like everybody else. You’ve got to read in the mirror, you have to hold the book upside down. That is a superpower. No one else can do it in your class. … I started building my confidence.”

Your mother surprised everyone after her death. What happened?

“She was not a classically trained accountant. But what she did at that early age, which I found out later, after she passed, she took 20 per cent of her salary and invested in the S&P 500 in dividend paying stocks, and telco bonds, Bell Canada bonds at 7 per cent, seven-year duration at that time.

My mother was doing that without telling either husband, either Terry or George. They never knew she had her own account. Over the years that thing became an incredible portfolio.

She absolutely killed it over 52 years. And when she passed away, … the executor of her will said, ‘You got to come down here. Your mother died a very wealthy woman.’ I said to him, ‘Impossible. We’re a middle-class family.’ He said, ‘No, you’re not.’”

Did something in your mother’s lifetime shape her to be a successful entrepreneur?

“She didn’t want any men to control her, ever. She actually divorced Terry. It was not a great marriage. She took us to Switzerland, Sweden, Finland. She was being chased by the courts to give up her children. This is a time when … it was severely frowned upon to divorce. … And she didn’t give a damn.”

How has this influenced your own choices?

“I just was at the United Nations this week in New York, I am going to, as part of this mandate for sustainable initiatives that they are pushing forward, I’m getting behind gender equality, to equalize pay globally for women who married. Not because it’s emotional. For me, it’s good business.

You know, 75 per cent of my returns over 15 years on Shark Tank have come from companies run by women. Well, they reached out to me and said, ‘Listen, why don’t you start to get behind our global initiative on gender equality?’ And 100 per cent, why wouldn’t I? It’s good business.”

Looking back, when did your entrepreneurial spirit ignite?

“I know exactly when it happened. … I was in high school in Ottawa. I got a job at an ice cream store at the mall near there. The reason I took the job is the girl I was hot for in Grade 11 was working in the mall right across from the ice cream store at a shoe store.

After my first shift, the owner wanted me to get down and scrape the gum off the floor of the ice cream store. I could see this girl looking at me, and I said I wouldn’t do it. The owner fired me. I rode back home on my bicycle, and my mother said, ‘When you work for somebody, you’ve got to do exactly what they say.’ That was the last day I ever worked for anybody.”

From that turning point, what brought you to establish your first company?

“My stepfather was very pragmatic. I was very interested in being either a musician or photographer or filmmaker, and he told me that I’d starve to death because there are so many people that are good in those. I was at the University of Waterloo and I was doing a lot of work in film and making films for the university and doing quite well at it.

I made a film about the controversy over damming the Grande Valley near Waterloo. It scored me fours across the board. I came away with honours and got into the MBA at Ivy with those marks. And as soon as I got to Ivy, I suggested to the dean, ‘Look, I make films. Why don’t you pay me to chronicle the next two years, and you’ll have the best recruitment film you’ve ever had?’ Which I did. And he did.

[After graduating,] we formed a company called Special Events Television. And we started doing sports broadcasting for the networks.

We broadcast for Don Cherry, for CHCH, Hamilton, Boston, Detroit… I worked at the CBC. And we sold the company 24 months later, because we owned the format, Don Cherry’s Grapevine, and that’s when my journey really took off.”

What did you do after selling the television production company?

“I was pretty young, and we made our first sale. I had a bunch of capital, so I said, ‘Let’s do it again.’ That was the beginning. That’s how I developed Softkey software in 1986, which turned into The Learning Company. I sold that to Mattel for $4.2 billion and I never looked back.”

How would you describe your attitude?

“My attitude today is I can do anything I want, anywhere I want, anytime I want. That is personal freedom I have; I have achieved that on my own. I can do whatever I want. And I also feel that many people can’t do what I can do. And I’m very competitive.”

You mentioned being advised by your stepfather to avoid the arts, but often people who are artists or athletes have unique skills.

“It’s funny you mention that, because with every résumé I’m given, I look for the yin and yang of the artistic discipline. Because of the binary discipline of business, which is black and white to either make money or lose it, but I want the chaos of art in the manager. I like to ask if they dance, play an instrument, paint… You have to have some kind of creative approach because the most successful businesspeople are grabbing inspiration from so many different places.”

What brought you to your Shark Tank gig?

“I had worked a couple of years with Stuart Cox on Dragons’ Den in Toronto.

Then I got a gig in London, England, with Discovery Channel called Project Earth, and I was working in London when I got a call from Mark Burnett, the famous producer. He said, ‘I have a new project called Shark Tank and we’re looking for a real asshole and you’re it.’”

What’s the best part about being on the show?

“The fact that a 9-year-old girl recently ran up to me in San Francisco Airport to say, ‘You should have done a convertible debenture last night up 20 per cent.’ Her mother caught up with her and explained to me that she’s a phenom in physics. We’ve had three generations grow up over 16 years on that show.”

Are you seeing any trends in venture capital right now, and are there any sectors you feel excited about?

“Canada is the richest country on Earth run by idiots. … I’m waiting for new management to come into play in Canada. Money is not political. It seeks the path of least resistance.

I love to pick a new sector, like watch insurance. I’m going into the watch insurance business in January. Just try and compete with me. I’m a huge watch collector. If you’re wearing a watch worth a million dollars, you want to insure it, you can’t put that on your house. I’ve started wondercare.com. It’s a brand for me.

[It will] provide you watch insurance that you can buy for a week, a year, a month, whatever you want. I collect them from all around the world. I know every brand; I know all the CEOs. My passions are watches, guitars and cooking. That’s my yin and yang.”

Responses have been edited for clarity and length.

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