O’Leary had launched his funds with great fanfare back in 2008, introducing them to viewers on his Business News Network (BNN) show, SqueezePlay. Before the cameras, wearing a natty navy-blue suit and matching azure tie, O’Leary resembled a proud father with a new infant as he explained to co-host Amanda Lang how his fund was designed to produce yield on a monthly basis.

Buried in the back pages of the financial press last October was a story about the sale of his mutual fund company, O’Leary Funds, to Canoe Financial, an investment firm run by former Dragons’ Den cast member and entrepreneur Brett Wilson.

The reality was quite different. O’Leary was not even licensed to manage or invest other people’s money. Instead, he hired Connor O’Brien, a former Wall Street investment banker, to run O’Leary Funds. Moreover, by 2012, the funds were in trouble, falling to $1-billion in assets by the end of that year.

O’Leary’s popularity and persona as a business guru soon drove investors to his mutual funds, with O’Leary Funds roaring to as much as $1.5-billion in assets (and probably more). O’Leary boasted of being an investing whiz, with access to the movers and shakers in the business and political worlds — those ties giving him unique insider knowledge.

In those days, O’Leary’s star was ascending. He was one of the so-called “Dragons” on Dragons’ Den, which was becoming a bonafide Canadian hit. The following year he and Lang moved their daily business show over to the CBC, renamed The Lang & O’Leary Exchange.

“You got to pay Daddy,” he declared, “because my wife costs a fortune, my kids cost a fortune. I need dough and I need dough every month. You got to pay Daddy number one.”

SoftKey moved to Boston and focused on the booming field of educational software. By 1993, it was trading on Nasdaq and had revenues of $110-million—and a loss of $57-million. The company grew by making a string of acquisitions.

By 1983, O’Leary saw the potential in the emerging software and personal computer industries. He formed SoftKey Software Products Inc. in the basement of his Toronto home, convincing computer companies to bundle his software into their products.

But what exactly is O’Leary’s business experience? Born in Montreal in 1954, O’Leary had ambitions of being a photographer. Instead, he did an MBA at the University of Western Ontario. After business school, he set up a television production company that produced shows for people like Don Cherry. From watching Cherry, O’Leary learned that it was important never to be boring or small on TV.

O’Leary is unquestionably a media star: He has written best-selling books, been a fixture on at least four televisions shows, including the current ABC hit program Shark Tank, revels in making outrageous statements, and crafted an image as the “mean” Dragon, able to reduce inventors to tears with putdowns like “this is the worst idea I have ever heard in my life it’s so bad!”

While O’Leary recently grabbed headlines with his promise to invest $1-million in Alberta if premier Rachel Notley stepped down, and is toying with running for leadership of the federal Tory party, these stunts overshadow a history of ineptitude as a businessman.

Yet the demise of the O’Leary Funds is, in fact, just the latest in a series of failures in Kevin O’Leary’s business career.

This past fall, when he finally sold his company to Canoe, the funds were down to $800-million in assets. This was due to redemptions — investors pulling their money out because of the funds’ performance. “The majority of the funds performed poorly for an extended period of time and the majority of (Bay Street) brokers refused to sell any new funds,” says Mark McQueen, CEO of Wellington Financial LP, a $900-million Bay Street finance firm and one of O'Leary's long-time critics. “It’s not personal. The industry lives and dies on performance.”

Yet SoftKey’s acquisition of TLC went through, and SoftKey adopted the TLC name. By 1996, TLC had 3,000 employees and was the biggest educational software company in the world. It continued to grow via acquisitions, driving revenues up over $800-million.

CFRA alleged that SoftKey may have overstated its earnings by bundling various general and administrative costs into write-offs. CFRA was also unhappy with SoftKey’s decision to fire its auditor, Arthur Andersen, after the accounting firm found deficiencies in the company’s internal controls. CFRA noted that SoftKey’s audit committee “holds several questionable members, including the CEO… as well as an outside member associated with two public companies charged with financial improprieties and another member who is a paid consultant to the company.”

SoftKey’s most prominent takeover was of San Francisco-based The Learning Company (TLC). Prior to the sale, TLC hired the Center for Financial Research and Analysis (CFRA), a forensic accounting firm, to examine its suitor’s financials.

But SEC filing shows that TLC suffered net losses of $376-million in 1996, $495-million in 1997 and $105-million in 1998. Moreover, TLC’s accumulated deficit topped $1.1-billion by the end of 1998.

That same year, toy giant Mattel Inc. made a takeover bid for TLC, without doing proper due diligence. Desperate to reverse a steep slide in the company’s stock price, Mattel CEO Jill Barad seized on educational software as a driver of future growth. The takeover shocked many, largely because TLC was seen, according to software-industry analyst Sean McGowan, as a well-known “house of cards” that was burdened with tired brands—not helped by the fact that O’Leary had slashed R&D from 24 down to 11 percent of expenditures. “There was a lot of [TLC] inventory out there that was not moving very well,” McGowan says. “They pumped up the sales by repackaging and distributing to convenience stores and drugstores.”

Indeed, TLC was later accused in a shareholders’ lawsuit and by a Mattel executive of “stuffing the channels”—shipping product at the end of a quarter and recording it as revenue, even though much of the merchandise would be returned. “Stuffing the channels was part of the business back then,” says a former TLC sales rep based in California.

In the end, Mattel purchased TLC for about $4-billion in the spring of 1999. O’Leary took over as president of Mattel’s new TLC digital division. Weeks after the sale, CFRA produced a critical report on Mattel, claiming TLC was already experiencing collapsing revenue, a surge in receivables and a deterioration of operating cash flow.

In the third quarter of 1999, Mattel expected profits of $50-million from the TLC division. Instead, it was a loss of $105-million (the next quarter losses rose to $206 -million), which wiped out more than $2-billion in shareholder value in one day, as the company’s share price slid from nearly $17 to $11.69.

In short, O’Leary had sold Mattel a turkey.

One investors' lawsuit says O’Leary cashed in his Mattel shares just before the losses were announced when the stock was at its peak, pocketing almost $6-million.

In November of 1999, O’Leary was fired, six months into a three-year contract. Four months later, Mattel’s CEO, Jill Barad, was forced out too. “There is nothing I can say to gloss over how devastating The Learning Company’s results have been to Mattel’s overall performance,” Barad said as she went out the door.

Mattel hired Bernard Stolar, a video-game executive, to see if he could salvage TLC. “It was an absolute disaster,” he says. In 2000, Mattel handed over its multi-billion-dollar acquisition to another firm for a mere $27-million and a share of its future profits.

Mattel’s purchase of TLC was later labeled by Businessweek magazine as one of “the Worst Deals of All Time.” Shareholders launched a class-action lawsuit, naming O’Leary as a defendant, accusing him of insider trading and of being part of a scheme to obscure TLC’s financial state. While O’Leary denied the allegations, in 2003, Mattel settled the lawsuit for $122-million—considered a “mega-settlement” at the time. O'Leary has blamed Mattel's management for the problems with the TLC division, not his own involvement.

While O’Leary’s actions cost Mattel’s investors hundreds of millions, he netted $11.2-million between his severance package and sale of his Mattel stock.

Sued for wrongful dismissal

After getting canned by Mattel, O’Leary’s business career sputtered and meandered.

In 2003, O’Leary invested in a self-storage company called StorageNow Holdings Inc., which he learned about from Reza Satchu, a Toronto entrepreneur. Satchu’s high-school acquaintance, Jonathan Wheler, had a background in real estate and saw that a lot of money could be made by building self-storage warehouses in accessible locales. Wheler had even found a perfect piece of land in Toronto to erect such a facility. According to court documents, O’Leary put in about $500,000 and ended up with almost 13 percent of the company.

In the summer of 2003, the Toronto land was purchased and, for a cost of $5.2-million, StorageNow’s first self-storage facility was built and opened in the spring of 2004.

But the relationship among the three men deteriorated. Wheler oversaw building the Toronto facility and finding other plots of land to construct similar warehouses. Eventually, he negotiated a deal with the Satchus and O’Leary to divide up the company’s eventual profits. In a $10-million wrongful dismissal lawsuit, Wheler contends that Satchu and O’Leary arbitrarily altered the agreed-upon compensation deal, reducing his cut of the profits substantially.

A further deal related to profits derived from the Toronto facility was finalized in 2004. But in April of 2005, Wheler claims he met with O’Leary who told him that this agreement was “too rich” to Wheler and what had been agreed upon was “simply no longer available”, according to Wheler’s lawsuit. O’Leary told Wheler his pay and compensation arrangements would be cut back. The following month, Wheler was terminated. Wheler believes that once O’Leary and Satchu realized how profitable StorageNow was going to be, they pushed him out of the business.

In a defense statement, Satchu and O’Leary claim Wheler was let go because he was inexperienced and lacked business acumen and fell behind schedule. Despite such characterizations, Wheler went on to develop a series of other self-storage units across Canada with another company using his original concept and became a millionaire on paper.

O’Leary and his partners soon were out-maneuvered by their competitors. A competing company, InStorage Self Storage Inc., blew by them, growing so rapidly they gobbled up StorageNow in 2007.

There were other miscues for O’Leary, too. In 2004, he was appointed to the board of Environmental Management Solutions Inc. (later called EnGlobe Inc.), an Ontario waste management firm. Soon afterwards, the board fired the company’s CEO. But the company’s leadership was unable to arrest a decline in its fortunes brought on by an overambitious acquisition program; the stock price slid from close to $4 to 3.5 cents during O’Leary’s term of almost five years as a director.

“I have had some great successes and great failures,” O’Leary said in a 2012 interview. “I think every entrepreneur has. I try to learn from all of them.”

O'Leary becomes a TV stereotype

In 2003, O’Leary talked his way into a job onto TV at BNN, partnering up with Amanda Lang on SqueezePlay, a daily business show.

O’Leary was made for television, having soaked up the lessons learned from Don Cherry years earlier. He was the sort of person who would bring a box of dog biscuits to the set and howl if he thought a certain stock was a “dog”.

But O’Leary also revealed his ignorance of the markets too. In the early aughts, Bay Street began peddling income trusts to investors. But Al Rosen, Mark Rosen and Diane Urquhart, experts on investment products, concluded income trusts shared characteristics of Ponzi schemes, with many destined to fail. In 2005, they produced a report saying 50 of the top income trusts were overvalued by almost 30 per cent.

Yet Al Rosen recalls O’Leary championing income trusts on his TV show. Rosen says he went on BNN and argued with O’Leary about the subject. “He’s an ignorant man,” says Rosen, one of Canada’s leading forensic accountants. “He was trying to kill us every time. We would see each other and almost spit on each other.”

In 2006, O’Leary was cast on Dragons’ Den for its first season, taking on the role as the resident asshole. He was the sort of person when an inventor burst into tears after being criticized by the Dragons, would say, “Money doesn’t care. Your tears don’t add any value.”

Henry Mintzberg, the Cleghorn professor of management studies at McGill University, believes O’Leary’s depiction of a business leader is pejorative. “Pitbull (executives) don’t add anything at all,” he said in an interview with this reporter back in 2012. Mintzberg said in the US there’s been the emergence of the “cult of heroic leadership” within corporations. “The tendency there… is to attribute any success of the company to one person,” he remarked. But Mintzberg said companies function best when CEO’s recognize that companies are collaborative efforts and they show flexibility and emotional health. O’Leary, on the other hand, “is obviously an arch narcissist,” noted Mintzberg. “I don’t know how he manages his companies, but his stereotype is dysfunctional.”

Dragons’ Den became a huge hit. Yet one of the myths of the show is that the deals struck by the Dragons on TV turn into real investment. In reality, only a minority of deals actually materialize. Moreover, Tracie Tighe, the show’s executive producer, once said O’Leary is “tight with his wallet” and closed only one or two deals a year.

Indeed, O’Leary had a history of rarely investing with entrepreneurs and of denigrating sound projects. When Rachel Mielke, a jewelry-maker based in Regina, appeared on the show in 2008 seeking $200,000 for a 20 percent stake in her jewelry company, Hillberg & Berk, she told the Dragons that her company was valued at $1-million, a sum O’Leary openly derided. “Kevin, right from the get-go, said ‘This is a bad idea',” Mielke recalled in an interview in 2012. “He didn’t really understand the industry.”

Rachel Mielke photo from Hillberg and Berk website

In the end, Dragon Brett Wilson agreed to back her company, which shot to sales of $5-million by 2014. “Within a couple of years it was quite clear that we had surpassed the valuation that I went to Dragons’ Den with,” said Mielke.

Even one of O’Leary’s success stories is not all what it cracks up to be. Wendy Johannson and Claudia Harvey invented a utility glove for women and needed $50,000 when they went on the show in 2009 for their company, DigIt Apparel Inc. On-air O’Leary agreed to give them the money in return for three percent of royalties. After the show, they eventually gave him 10 percent of the company.

But the $50,000 never materialized. “When he said he’d like to have ten percent for $50,000 I thought that would be a cash injection, I thought that was money in the bank for us,” said Harvey in an interview in 2012, “When it came down to it… that wasn’t the case.”

Instead, O’Leary offered them a line of credit at an interest rate higher than what the banks offer, which DigIt didn’t touch. “He’s never actually given us any money,” said Harvey at that time, although the two women were happy with his contribution to the company by opening doors to retailers.

O’Leary told the Globe and Mail in 2012 that Johannson and Harvey wanted to use the money for inventory, which he didn't think was a good use of his money. He said he was proud of what the pair had achieved.

The rise and fall of O'Leary Funds

By 2008, having painted himself as a business guru, O’Leary felt it was time to cash in on his new-found fame and start another business.

That summer, he announced the creation of his own mutual fund company, O’Leary Funds, despite not having a background in investing other people’s money or a broker’s license, and having denigrated mutual funds on TV.

In the end, O’Leary would be the hood ornament to woo investors; he hired former Wall Street investment banker Connor O’Brien to be the portfolio manager. One of the first things O’Leary said was he wouldn't “grind the capital” of investors, meaning he would not pay back to investors their very own principal to meet dividend demands (as opposed to generating dividends as a result of astute investing).

The funds took off. By 2010, O’Leary was hoping his funds would hit $5-billion in assets within three years.

Yet it was not long afterwards that some sharp-eyed experts on Bay Street found evidence that, in fact, O’Leary Funds was paying out dividends to investors with their very own cash – in other words, grinding their capital. “The issue is not do other people grind their own capital, it’s that he said he doesn’t do it,” says Mark McQueen, CEO of Wellington Financial. “And I found half a dozen of his funds where he had.”

By 2012, investment advisers were pulling their money out of the O’Leary Funds simply because they were not performing as well as O’Leary had touted. And the funds continued to leak over the next three years before O’Leary finally folded his tent last fall, selling the entire business to Brett Wilson's Canoe Financial.

Meanwhile, O’Leary’s television career also began to flag. In 2014, he left CBC and Dragons’ Den and The Lang & O’Leary Exchange to become a gadfly at CTV. His profile in Canada has dimmed considerably since.

In the end, O’Leary succeeded in becoming a millionaire. But more so because he learned how to turn himself into a celebrity and not because of his business acumen.

Portions of research for this article were previously published in 2012 in the Globe and Mail's Report On Business Magazine, co-written by Mr. Livesey