Better known by Shark Tank fans as “Mr. Wonderful,” Kevin O’Leary is a businessman through and through -- not to mention one of the tougher investors on the show. But as the case with most entrepreneurs, circumstances have not always been wonderful for O’Leary. He’s experienced more than his fair share of failure along the road to success.
Born in Montreal, Quebec, to an Irish father and mother of Lebanese descent, life got difficult fast when his parents divorced early on, followed by the death of his father. Luckily his mother, Georgette, set a great example, not only by being a stellar investor, but by overcoming every obstacle life threw her way.
Here are some of O’Leary’s biggest failures, how he overcame them and what we can all learn:
1. When he was fired from his job at an ice cream parlor.
For O’Leary, the lessons started early. Like many teens, his first paying job was in a mall, in his case scooping ice cream. One day, his boss asked him to scrape gum off the ground. Unwilling to embarrass himself in front of his crush at the shoe store across the way, he refused on the grounds that it wasn’t his job.
As you might expect, he was fired. It was a poignant moment for O’Leary, whose failure to keep the job taught him an important life lesson. He wanted to be an entrepreneur.
"From that day on, I swore I'd never work for anyone else,” O’Leary said of the occasion. “That was the beginning of my journey."
2. When he graduated from business school despite dyslexia.
O’Leary originally wanted to become a photographer, but attended university instead at his stepfather’s urging. His challenge? He’s been dyslexic as long as he can remember. Educational therapists helped him see his dyslexia in a different light. By viewing his dyslexia is an advantage, not as a failure, O’Leary gained confidence that would allow him to graduate with honors at the University of Waterloo, then earn an MBA in entrepreneurship at the University of Western Ontario’s Ivey Business School.
Of his dyslexia, O’Leary said, “It shouldn’t in any way diminish your self-esteem or be considered something that is going to hurt your chances to be successful at work or in life.”
3. When his big break hit a rocky road.
O’Leary’s first big break came when he started Softkey in his Toronto basement, acquired The Learning Company (TLC) and adopted its name, then sold it to Mattel for $4 billion. The acquisition was fortuitous for O’Leary, but less so for Mattel, which subsequently experienced a drop in earnings, sales and stock price.
Mattel even went as far as to sue over the disastrous merger, which O’Leary believes to have been the result of culture clashes between the two companies.
The failure affected O’Leary, who mostly felt sorry for his employees. “I feel like I let them down,” he said. “They’d worked so hard.” But the greater lesson is that not every company can or will survive. When acquisitions happen, success is not guaranteed, and even the best companies can get eaten up. “That’s the thing about business,” he said on the matter. “It’s very Darwinian.”
4. When he squandered $2.5 million.
In a video on failure, O’Leary cited a partnership with a cable conglomerate, for whom he proposed a consolidation of online dating services in order to sell them as a subscription service. Though the idea was a good one, the problem was the partnership: it was hard, if not impossible, to get things moving when handcuffed to a big corporation.
It took $2.5 million out-of-pocket before he learned the error of his ways. He’s since learned that such partnerships are a bad idea, because progress will get caught up in bureaucracy and stagnate. As a result, he’s infinitely more likely to partner with small businesses and sell to conglomerates instead.
“You have to admit your failures, you have to understand why you failed, and you have to learn from them so you don’t do it again,” he said of the incident.
5. When he came close to divorce, but recommitted instead.
Balancing home life and business is an enormous challenge and one O’Leary very nearly failed. He admitted that while building his empire, he was an absentee parent. He lived apart from his wife for two years and was on the verge of divorce. They were about to divide their assets, O’Leary said, “but as we neared it, we decided not to do it. We have reunited and kept the family together. I’m glad we did that.” He’s since learned to treat his marriage like a business -- an important one that requires equal partnership and effort -- instead of taking it for granted.
6. When he dropped out of the race for Prime Minister.
Just this year, O’Leary entered the Conservative leadership race for Prime Minister of Canada. After entering politics for the first time on a national stage, he was a frontrunner in the polls for most of his run. Still, he dropped out in April 2017, citing lack of support in Quebec and the lack of a strong plan capable of beating current Prime Minister, Justin Trudeau.
“It would have been selfish to just go for the leadership and not deliver the mandate that I promised. I said if I can't deliver a majority mandate, fire me," he said. Knowing when to quit certainly softens the blow, and turns his failure on its head -- because the real failure, as good investors know, would have been pursuing something out of self-interest with no regard for numbers.