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Canadian businessman Kevin O'Leary speaks during the Conservative Party of Canada convention in Vancouver, Friday, May 27, 2016. O'Leary says there are all sorts of rumours swirling about when he will join the Conservative leadership race.But he's refusing to comment on the latest one: that he'll finally launch his campaign Wednesday afternoon in Toronto.THE CANADIAN PRESS/Jonathan HaywardThe Canadian Press

As the Ottawa bubble debated whether Kevin O'Leary would have the audacity to run for leader of the Conservative party, one talking point was repeated as a glaring knock against his potential candidacy: He can't speak French.

Because this is a bilingual country, and because Quebec votes are crucial to any leadership bid, it was a convincing argument. But it also masked a hidden truth -- Mr. O'Leary's big weakness is his business history.

Like Donald Trump, he tries to project an image that suggests every business he's touched is wildly successful. As we uncovered in Report on Business magazine, the reality is much less rosy. Mr. O'Leary's billion-dollar sale of his software company in 1999 proved to be a disaster, his track record on Dragon's Den was spotty, and the investment fund company he co-founded roared out of the gates, only to fall out of favour with investors and their advisers.

Read more: Kevin O'Leary joins race for Conservative leadership: 'I'm in'

Opinion: You don't speak French? You shouldn't lead the Conservatives

From the archives: Kevin O'Leary: He's not a billionaire, he just plays one on TV

The deal that put Mr. O'Leary on the map dates back to the 1980s, when he and a business partner founded a company called SoftKey Software Products Inc. By 1993 the business was publicly traded in the U.S. and mid-way through that decade the founders sought a major expansion, which included launching a hostile bid for San Francisco-based The Learning Company (TLC), which specialized in educational software.

Through the merged company, which adopted the TLC name, Mr. O'Leary came to help oversee 3,000 employees and about $800-million (U.S.) in annual revenue. Profit, though, remained a struggle. The company suffered net losses of $376-million in 1996, $495-million in 1997 and $105-million in 1998 – some of which stemmed from non-cash, goodwill writeoffs that came from buying other businesses.

Nevertheless, amid the growing excitement about software companies in the late '90s, private equity firms grew interested and they pumped $123-million into TLC, taking an ownership stake. A year later, toy behemoth Mattel Inc. bet that educational software would be the future and bid about $4-billion for TLC. The deal closed in the spring of 1999.

It got ugly, quickly. Weak profit estimates helped erase over $2-billion in Mattel's market value in one day and as the division's losses piled up, Mr. O'Leary was fired six months into his three-year contract. Mattel's CEO was sent packing four months later.

As for what Mr. O'Leary walked away with, it's far from billions of dollars, which is sometimes presumed considering the takeover's size. The private equity owners got most of it; he netted $11.2-million through his severance package and sale of Mattel stock.

Asked about the collapse in 2012, Mr. O'Leary said he had no regrets. "I look historically back at that deal, I'm very proud of what we created there. We had some fantastic assets in that company and great people too," he told the Globe.

His next major act was on television. Mr. O'Leary was cast on CBC's Dragons' Den in 2006 and it was there that he made his name with Canadians, playing the caustic judge who took pleasure in telling contestants how silly some of their business ideas were.

It made for great TV, but hardly any deals came out of it. The dirty little secret of Dragon's Den is that very few transactions are ever consummated. "About a third of the deals close," Mr. O'Leary admitted in 2012, adding that even fewer make money – common for the venture capital industry.

In 2008 he launched O'Leary Funds, an asset manager in his very name.

Early on, the investments sold like hotcakes, hitting $1-billion in assets under management in about two years. Around that time, Mr. O'Leary said he expected to hit $5-billion in assets by 2013, adding that he had plans to take the firm public.

It was largely downhill from there.

When he launched the company, Mr. O'Leary swore off risky investments, promising that the funds would target stable, dividend-paying companies. Two years in, the asset manager was dabbling in securities such as Brazilian bonds that paid 11 per cent annual interest. (In 2012, his portfolio manager Connor O'Brien said these investments amounted to "very little, very, very little" total fund exposure.)

For various reasons, returns started to sag. Two funds launched in the first half of 2011 had lost more than 20 per cent each, before distributions, by the fall of 2012. Soon retail advisers that pushed O'Leary Funds to their clients wondered what happened to the safe-investment promise.

O'Leary Funds was eventually sold in 2015 to Brett Wilson's Canoe Financial. At the time, it had $800-million in assets under management (AUM) – one-third less than the $1.2-billion O'Leary Funds managed at the end of 2011, and far from the $5-billion goal. In an interview with the Globe, Mr. Wilson acknowledged Mr. O'Leary "got hit with some big redemptions," noting that "one can point out that Kevin overpromised and underdelivered."

A sale price was never disclosed because the firms are private, but money managers are often sold for between one and three per cent of assets under management. Assuming a two per cent mid-point, the sale price could have been $16-million, and the last public record of Mr. O'Leary's ownership pegged his stake at 45 per cent.

Will any of this matter in the leadership race? Who knows? We live in precarious times. Donald Trump probably didn't pay taxes for as long as 18 years, yet poorer voters in some Midwest states didn't seem to care.

Canadian politicos love to say this is a very different country, and that we're much more sensible people. But sometimes, bluster has remarkable power. Toronto elected Rob Ford as its mayor, remember.

It takes charisma to disarm a bully, and the current crop of Conservative leadership candidates is seriously lacking on this front. The funny twist here is that the one person chock-full of charm is Prime Minister Justin Trudeau, and he'll square off against the new CPC leader in the next federal election. Anyone considering voting for Mr. O'Leary as the best hope to defeat Mr. Trudeau ought to remember that.

Follow Tim Kiladze on Twitter: @timkiladzeOpens in a new window

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