Toronto Life - The Informer

Insider intel on the politics and personalities shaping the city. Sign up for Preview newsletter for weekly updates



Five things we learned about Kevin O’Leary from Report on Business’s scathing feature

(Image: Frederick M. Brown/Getty Images Entertainment)

Although Kevin O’Leary undoubtedly enjoys the spotlight, there are things the businessman and professional pot-stirrer would probably prefer to keep quiet. This morning, Report on Business published a lengthy investigative profile by Bruce Livesey and Tim Kiladze that skewers his carefully wrought image as a savvy and successful business leader. Below, the five juiciest tidbits about the media personality, including the inside scoop on a failed Dragons’ Den deal, and why some investment advisors are wary of O’Leary’s investment fund.

1. The business deals that made him rich were controversial
The official story about O’Leary’s rise to prominence is that he built a hugely successful educational software company called SoftKey (later renamed TLC), which he sold to Mattel for just under $4 billion in 1999. However, the ROB feature lays out a counter-narrative, presenting evidence that TLC overstated its earnings through accounting gymnastics, and noting that it lost money for the three consecutive years leading up to the Mattel deal. Moreover, the takeover was disastrous for Mattel, which ended up selling TLC in 2000 for $27.3 million—Businessweek called Mattel’s purchase one of the “worst deals of all time.”

2. He’s not a billionaire
Though he is definitely very wealthy (and likes nice things, too), O’Leary is sometimes mislabelled a billionaire because of the $4-billion purchase price in the Mattel deal (most of that money actually went to a group of investment firms that had taken an ownership stake in TLC in 1997). O’Leary earned only $11.2 million from his dealings with Mattel: nearly $6 million from selling his portion of Mattel stock, and $5.25 million from a severance package after he was fired six months into his new post as president of Mattel’s TLC digital division.

3. He really is as fearless as he seems
For proof of O’Leary’s brashness, look no further than how he got his start in television. In 2003, Jack Fleischmann, the general manager of Business News Network, received a call from some guy named Kevin O’Leary who wanted to be on television. Despite the fact that it was a cold call, Fleischmann agreed to an audition and was hugely impressed by O’Leary’s sharp delivery. “He absolutely, totally, from the moment he opened his mouth, lit that camera up,” Fleischmann told ROB’s reporters.

4. Those Dragons’ Den deals don’t always work out
Apparently, a minority of the deals made on-air during Dragons’ Den actually close. Kiladze and Livesey track the story of Neil Currie, who went on the show with his business partner in 2009 and made a deal with O’Leary for a cash infusion in exchange for 50 per cent of their online company. Afterward, when the entrepreneurs couldn’t get O’Leary on the phone, they decided to build their business without him. A year later, CBC called to see if they’d still make a deal with O’Leary, but they were already making money and no longer needed him. According to Curry, O’Leary lost out on nearly $500,000 in 2011 alone.

5. Some prominent advisors are increasingly wary of O’Leary Funds
O’Leary launched an asset management company (named after himself, natch) in October 2008. By 2010, he had raised more than $1 billion and bragged that he expected to quintuple that within three years. However, ROB reports that investors have begun to pull their money from its funds; the magazine also says prominent investment advisors are worried that the funds’ promised yields are unsustainable and that some of their holdings are highly speculative. Some of those advisors have even called O’Leary to voice their concerns, including one who told the Dragon, “You’re supposed to be the smartest businessman in the world. How’d you end up in this situation?”

Kevin O’Leary: He’s not a billionaire, he just plays one on TV [Report on Business]

  • G.Bocek

    They say it’s all in a name and “leary” is coming through loud and clear for me. I get upset when I start paying myself interest or dividends from my original investment because it is essentially losing value. O’LEARY funds started looking scary to me long before Halloween season but in keeping with upcoming events decided to say a “BOO” to you Kevin not just because of the drop in value but I didn’t like the way you talked to those nice college guys on Dragon’s Den this week – the Ten Trees project. You clearly told the viewers you were more interested in money than being socially & environmentally responsible which many viewers such as myself find nauseating and repulsive. After listening to this muck I feel even better about my choice not to invest in anything associated with Kevin “LEARY”

  • karen

    I don’t understand why someone who cares only about lining his own pockets and does not give a hoot about Canada or the Canadian economy has such a ubiquitous presence on both the morning news and the evening business news daily. He certainly does not represent much more than a small portion of the Canadian population. Considering how distasteful his opinions are, why is he being given such a large voice on a network that is mandated to represent all Canadians?

  • Dana Bastien

    What noone seems to understand, is the impact of cronstructive criticism. Kevin O’leary’s way of guiding people in the right path is simply through constructive criticisim. I don’t know much about him, or how he became successful, but I have watched Lang&O’leary Exchange, and Dragons Den and he is being honest and straight to the point. Instead of beating around the bush, and leading people to believe in something that just isnt there, he is giving you the option to wake up and realize the brutal truth. That’s what I respect about him the most. Yes he can be harsh, but the truth is harsh. If he doesn’t say it, who will. As we’ve seen on Dragons Den, people lose there homes and everything in their life on a hope and a dream, and Kevin will openly and honestly tell them stop what you’re doing and start trying to build your wealth back before you end up with absoultly nothing. I find that to be the best advice anyone could give them, instead of giving false hope he is telling them the way it is. So instead of seeing him as rude and arrogant, just remember that he is telling it as he sees it. He doesn’t sugar coat it and lie, which I think everyone should be more like. The first step to progression is learning where your going wrong, not by being ackowledged for your success.

  • Murray

    How can one take O’Leary seriously? He has difficulty opening his mouth without cloaking his words in a cloud of narcissism. Does he truly believe what he says or does he just love listening to himself say it? Anyone wanting this individual as a business partner might also want to take up snake charming.
    The risks are about the same.
    It might be interesting to hear him speak without the cameras running but somehow I feel it would be difficult to take the theatre out of this man.

  • BlueZone

    After a while you learn the fine lines when Kevin talks.A billionaire won’t be in every Dragons Den episode,it’s too petty.This is also show business and I like his persona.I think he’s funny and sure he BS a lot too.

  • Shayne Monk

    I was surprised to hear someone who sounds so intelligent most times, speak out of turn about our Canadian Forces, and the equipment the government is trying to replace for our protection. As you know, the military is like having house insurance. You hope like hell you never need them, but when you do, you are glad you had them. Review your history lessons and get your head out of the clouds. Yes we are a loving, caring, and feeling society, but guess what…..? The rest of the world is not. Again review your history, and you don’t have to go back more than 11 years. A proud poor Canadian.


    Bald Everybody!

  • Rob

    I kinda dig their twitter account tho,