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Why Kevin O’Leary’s Judgmental Scorn Will Be Missed On Dragons’ Den

He’s opinionated and ruthless, and he hungers for big deals. Yet he made millions helping children learn how to read. Nothing if not a polarizing force on television and at the podium, Kevin O’Leary pulls no punches when it comes to the good, the bad, and the ugly as it pertains to markets and economic opportunities. O’Leary is co-host of The Lang & O’Leary Exchange; a judge on Shark Tank; and author of the bestselling book Cold Hard Truth: On Business, Money, and Life. He has also just announced his departure from Dragons’ Den. The Financial Post takes a look at the legacy O’Leary leaves behind him:

So it’s farewell, then, Mr. Wonderful, best and worst of Dragons’ Den. Canada will miss Kevin O’Leary’s smirking, judgmental scorn every week on the CBC reality show.

His chair may be taken by someone else, but his fearless vitality will never be replaced.

Like many Canadians, I’ve been amused and outraged by O’Leary during his seven years on the show, in which millionaire investors judge Canadian entrepreneurs on their nascent business ideas.

On a show that encourages five pedestaled millionaires to snub and mock their earnest supplicants, O’Leary was the rudest and crudest of them. He indulged himself shamelessly in name-calling and personal attacks, while incessantly chastising pitchers for mistreating money.

And yet, he was so often right. When pitchers brought bad ideas to the show, he called them out. He didn’t soft-soap them, or give them hope when there is none. He took fiendish delight in insulting them, but in the end, in his way, he was trying to help. When he imperiously told pitchers, “I forbid you to spend one more minute on this idea,” it was because he could see they had wasted thousands of dollars — and years of their lives — working on projects and products unworthy of their efforts.

Yes, he wanted to help. But, Ivey-trained marketer that he is, he did so in a way that was larger than life, full of invective and scorn. He knew this would build his brand as Canada’s commercial curmudgeon. (He used to work with Don Cherry, Canada’s top shock-and-awe celebrity.) O’Leary became our best-known business leader, if only because Canada’s business elite have been notoriously short of imagination, humour and charisma.

O’Leary’s public brand works because it is only a slight exaggeration of his real self.

I first met him in 1992. He was founder and president of Toronto-based Softkey Software, which redistributed brand name PC software on floppy disks at discount prices under its “Key” brand name. I was interviewing him in my capacity as editor of Profit, because Softkey’s five-year revenue growth qualified it for No. 1 spot on the magazine’s 1992 list of Canada’s Fastest-Growing Companies.

Even then O’Leary was a cutting-edge communicator, flinging quips and stories that transmitted his key messages with laser precision. He wanted Softkey to become “the Campell’s Soup of software.” His firm’s motto was simple but breathtaking: “Changing the way America buys software.”

And yes, he was just this side of crude. Speaking of the annuity power of personal tax software, he said, “If you publish a good product and bring out a better version every year, users will buy again. You’ve got them by the data.”

I told my colleagues at Profit that I had just met the best interview subject ever.

In later years, Softkey continued to grow, mainly through acquisition. It snapped up best-selling titles such as Reader Rabbit and Oregon Trail, shedding the anonymity of “Key.” Yet O’Leary kept his feet on the ground, often taking part in Profit events and other unpaid speaking engagements to share his entrepreneurial know-how with eager audiences.

Working with strong business partners, especially Softkey’s CFO Michael Perik, O’Leary rode the business to unexpected success — moving to the U.S., renaming itself The Learning Co. (TLC) after acquiring that Boston-based company in 1995, and eventually selling out in 1998 to toy giant Mattel for US$4-billion.

As chief executive of a public company, O’Leary saw only a fraction of that money reach his bank account. But even that was a lucky break of timing.

Little more than a year later, numbed by TLC’s high overhead costs and warehouses full of unsold CDs (at a time when the Internet really started changing the way America buys software), Mattel unloaded the division for US$27-million — less than 1% of its purchase price. Jill Barad, the rising-star Mattel CEO, lost her job, telling Wall Street analysts “There is nothing I can say to gloss over how devastating The Learning Company’s results have been to Mattel’s overall performance.”

There were inquiries and lawsuits, but no one ever pinned anything on O’Leary. After taking a few years off to study investing — and concluding that Bay Street and mutual funds are broken business models — O’Leary resurfaced as an investment commentator on BNN (then ROB TV). His quick wit and gift for spotting bad business deals made him a star on the dreary business network, and a must-have for the CBC when it launched Dragons’ Den in 2006. By 2012, The Globe and Mail called it “The Kevin O’Leary Show.”

Now Canada must move on, following a herd of dragons who are interesting people, but none so frank or capable of memorable invective. (Who could ever forget “You are going to zero with a bullet”?)

O’Leary will still pretend to cover business news on the CBC Lang & O’Leary Exchange. And we’ll still watch him chow down on bad ideas on ABC’s Shark Tank. But it won’t be the same. On Dragons’ Den, O’Leary was unleashed, and all ours.

Breathing fire or crunching bones, O’Leary will never be a touchy-feely business coach. (His latest mantra: “You’ve got to know your numbers, or I will eviscerate you.”) But this is the message we all need.

As Canada’s head executioner of bad ideas, O’Leary has played an essential role. Canada has come a long way in the last few years, from a nation of bankers and postal clerks to an entrepreneurial hotbed.

Entrepreneurship is a rewarding lifestyle and a necessary component of the digital economy, but it also has a dark side. If you’re not focused on your business plan, if you get easily distracted or misjudge your market, the results can be catastrophic. We need commentators who can slice through the noise and waste and remind us how unforgiving business can be.

In a competitive global marketplace, Kevin O’Leary has taught Canadians how value is created. There can be no accomplishment more wonderful than that.

By Rick Spence/Financial Post/April, 2014