Kevin O'Leary

The dastardly reality TV star’s flirtation with a federal leadership bid is sending the Conservative party into convulsions. There’s never been a better time to be an opinionated blowhard in politics, but is Canada really ready for Prime Minister O’Leary?

Just as Dr. Evil has his likeness chiselled into a mountain lair, the Entertainment District offices of the O’Leary Financial Group are decorated in wall-to-wall Kevin O’Leary. There are multiple stacks of his three books, his face glowering or grinning on the covers, and atop a fake Christmas tree, where an angel would normally perch, someone has stuck an enormous paper cut-out of O’Leary’s face. An O’Leary piñata—presumably filled with gold bullion—sits on a cabinet. Shelves overflow with awards and plaques. (O’Leary points out the best male villain statue he got at the 2014 Reality TV Awards. “I’m proudest of that one,” he says.) The walls are dominated by large, framed prints of O’Leary’s own photographs (of note: a self-portrait of a bearded, topless, 20-something O’Leary). Wine guides sit next to bottles of O’Leary’s Fine Wines. Everywhere O’Leary looks, he can see his face, his name, his many incarnations and enterprises.

This hall of mirrors doubles as a TV studio: the remote-controlled Azzurro production system includes two digital video cameras on the right side of O’Leary’s desk, a touchscreen controller to his left and a large Samsung backdrop that allows him to go on CNBC without putting on his shoes, never mind getting on a plane. Earlier in the day, he did his regular hit on BNN’s Market Call and appeared on the Marilyn Denis Show, where he exhorted viewers to abandon home ownership (in the Uber age, he suggests, why not rent everything?). Now he will appear on CNBC’s Closing Bell, to argue that Apple, in the wake of a disappointing earnings report, is no longer worth its price tag. He lowers the blinds, adjusts a couple of lights and inserts an earpiece. He does a winking sound check: “Tonawanda in flames, film at 11.” I’m sitting beside his desk, watching him on an iPad, and my eyes dart back and forth from real O’Leary to televised O’Leary to all the O’Leary effigies that surround us. It feels like a reboot of Being John Malkovich, written, directed and produced by Kevin O’Leary.

The 62-year-old O’Leary is, of course, Canada’s most famous businessman and arguably the country’s most successful television export since William Shatner. It’s difficult to tell where one role ends and the other begins, and whether or not that matters. O’Leary has monetized his entire existence, and it’s a genius hustle, really. As the ubiquitous, loud-mouthed dark lord of ABC’s reality TV show Shark Tank, he can promote his own products and services while ferreting out new ones to profit from. At the moment, O’Leary Ventures owns a piece of some 20 small businesses, including Wicked Good Cupcakes, Voyage-Air Guitar and IllumiBowl, which produces a motion-activated night light that attaches to your toilet. Estimates put his net worth somewhere between $300 million and $400 million. When I put the question to him directly, he demurred: “My mother taught me it’s bad karma to boast about wealth.”

When you’re on TV as much as O’Leary is, you don’t really ever take off your makeup (O’Leary carries his own kit everywhere, in a small black nylon bag). You also develop a signature look. He wears only one thing in public: black bespoke suit (made by Obama’s tailor, Martin Greenfield—O’Leary has more than 20 of them), white shirt, black Prada or Hermès tie. His French cuffs are adorned, archly, with silver skull cufflinks. His own bald skull, thanks to the makeup, is the colour of sandblasted brick. If George Costanza played a hit man in a Tarantino movie, he might look something like this.

While O’Leary continues to pontificate on financial matters, he has also turned his attention, loudly and acutely, to politics. At every opportunity, he has trolled Justin Trudeau, Kathleen Wynne and Alberta premier Rachel Notley, merrily mocking their fiscal policies. And then, in January, he announced that he might run for the leadership of the Conservative Party of Canada. The very idea induced panic attacks in some Tories. It also tapped into the same kind of disenfranchised, right-wing populism that’s led elsewhere to Trump and Brexit. In May, a Forum Research poll indicated that Conservative voters were more likely to elect O’Leary as their leader than Peter MacKay, Rona Ambrose or four other possible candidates.

He’s still flirting with the top job, but also says he might throw his support behind another candidate he likes or offer his services as finance minister. It’s been a long, slow, sadistic tease, one that O’Leary is relishing. “I don’t give a damn about the party,” he told me. “They’re losers. The Conservative brand means nothing.”

In O’Leary’s 2011 memoir, Cold Hard Truth, the word “money” appears 304 times. For O’Leary, money is motivation and inspiration. It’s also practically sentient. When he talks about mistakes his money managers made in the 2000s, he writes, in all seriousness, “I could hear my money asking, ‘Why? Why are you doing this to us?’ ”

O’Leary claims to be descended from an ancient line of Phoenician merchants, but he learned most of what he knows about business from his Lebanese-Canadian mother, Georgette Bookalam. She was the CEO of a Montreal children’s clothing company called Kiddies Togs. She and Terry O’Leary, a Kiddies Togs salesman, met in 1951, and Kevin was born in 1954. A brother, Shane, arrived two years later.

At Bookalam’s knee, little Kevin learned that he should save a third of every paycheque, invest only in stocks that pay a dividend and, above all else, avoid debt (“a cancer,” according to O’Leary). Terry, meanwhile, taught him other lessons. An outgoing, garrulous Irishman, he could sell anything, and Kevin loved watching him work. He also played cards, caroused and drank too much. When Kevin was seven, his parents divorced, and Bookalam got custody of the kids. She remarried a sober-minded Egyptian named George Kanawaty, who was doing his PhD in business at the University of Illinois. The family relocated there, and later to Switzerland, where Kanawaty worked for the UN. They moved back to Canada when Kevin was 16. The teenage O’Leary liked to party, he liked to drive fast (he totalled Bookalam’s BMW running a red light), and he liked to take pictures (fashion photographer Francesco Scavullo was an idol).

Over the years, O’Leary has burnished a few choice beats in his personal story. One of these is his first real job. In high school, he got a gig at an ice cream parlour, thinking it would be a good place to meet girls. On his second day, his boss told him to scrape some gum up off the floor. O’Leary refused, insisting he had been hired to scoop ice cream. He was fired immediately. With tears in his eyes, O’Leary biked home. His stepfather explained his mistake, that he was there to serve the person who owned the business, whether he liked it or not. It was a Damascene moment. O’Leary vowed that he would never work for anybody ever again. “To be happy,” he writes, “I would need to be in charge of my own destiny. I would need to become the boss.”

How you feel about Kevin O’Leary depends on how you feel about capitalism itself. If, like me, you feel that within every rich person beats the heart of a pirate, well, he’s a rapacious Bluebeard. On the other hand, if you think the wealthy make their money through hard work, pluck and balls-to-the-wall tenacity, then O’Leary’s your dark knight, a paragon of the winner-take-all free market.

That persona first emerged at Western, where O’Leary got his MBA. While there, he made a documentary about the program, and that experience led him to form a production company that created Don Cherry’s Grapevine, the interview show that turbocharged Cherry’s TV career. O’Leary sold that business in 1983, making enough for a down payment on a house on Shaw Street.

He’d make his real fortune in a somewhat different industry: software. O’Leary was an early adopter of the personal computer. In 1983, out of his basement on Shaw, he co-founded a start-up called SoftKey, which made software for offices. The business was characterized by ruthless efficiency and rapid growth, and by 1996, it had relocated to Boston and taken on the name of one of its many acquisitions, the Learning Company (TLC). In the ’90s, TLC was the biggest educational software company in the world. “Kevin was an early version of Mark Zuckerberg,” his former CFO Scott Murray says. “He was thoughtful about what the market might become even when it wasn’t there.”

Being a proto-Zuckerberg meant long hours and single-minded focus. Somehow, O’Leary found time to date and, in 1990, married Linda Greer, a student at U of T. They held a wedding party at the house on Shaw, and ordered pizza when they ran out of food. They had two kids, Savannah and Trevor, but O’Leary was so fixated on SoftKey, his other baby, he hardly saw them.

In 1999, Mattel bought TLC for $3.6 billion, and O’Leary joined Mattel in the takeover. But six months later, after large increases in his salary and severance package—and O’Leary selling most of his Mattel stock for $6 million—he was gone, fired when the TLC division lost millions. BusinessWeek, meanwhile, called the Mattel takeover one of the worst business deals of all time, and shareholders launched a class-action lawsuit, accusing O’Leary et al. of fudging the books and misleading investors. Mattel settled in 2003 for $122 million. “Anyone who can pick a corporate pocket for $3.6 billion is a pretty cool customer,” Time magazine wrote with grudging admiration. O’Leary still stands by the Mattel deal. “People criticize deals every day. It’s part of being in business,” he says. “I don’t apologize for the deal in any way.”

Post-TLC, the 46-year-old O’Leary bought the fanciest camera money could buy and spent a year hanging out on the finest beaches in St. Barts, Barbados, and Turks and Caicos. But being the world’s wealthiest beach bum wasn’t enough. After a few other entrepreneurial ventures, it dawned on him that the thing Kevin O’Leary might be best at selling was Kevin O’Leary. Over drinks at One in Yorkville, he met his friend Gene McBurney, a lawyer and investment banker. “You know what I’m going to do, Gene,” he said. “I’m going to brand myself.”

Fun fact: Kevin O’Leary is allergic to garlic. We’re having lunch at Nota Bene with Alex Kenjeev, the president of O’Leary Ventures and O’Leary’s right-hand man, and O’Leary has just ordered venison tortellini. When the food arrives, he realizes he didn’t mention the allergy to our server. He sends the food back, slightly sheepish, and orders a lobster salad instead. Kenjeev looks at me. “Kevin’s embarrassed to say it, so I will. It’s because…he’s a vampire.” O’Leary grins obligingly. When he was producing Don Cherry’s Grapevine, O’Leary watched Cherry morph from colour commentator to iconic TV personality. Along the way, he picked up some pointers: “Always be the antagonist, not the protagonist—being the good guy’s not interesting.” Vampires are interesting. As are assholes, jerks and bullies.

This was the world view with which O’Leary embarked on his own television career. By 2009, he was starring in two CBC shows. On The Lang and O’Leary Exchange, O’Leary was a right-wing attack dog, while the centrist Amanda Lang held his leash. Their chemistry was as palpable as it was baffling. While his knee-jerk paternalism occasionally got under her skin—“Don’t worry your pretty little head,” he’d scoff—Lang was impressed by O’Leary’s self-possession. “He’s one of the most confident people I’ve ever met,” she says. “And I mean confident in every way—he thinks he’s the most handsome guy in the room, the smartest guy in the room….” O’Leary still refers to Lang as his “TV wife.”

Meanwhile, on Dragon’s Den, the CBC’s venture capital game show, O’Leary worked a different kind of charm. When asked during an audition how he would characterize his style, O’Leary said, with just a whisper of irony, “I’m a wonderful guy. I start there. I’m Mr. Wonderful.” The sobriquet stuck. By its third season, O’Leary had expertly honed the persona: a smarter-than-thou blowhard known for his brutal honesty and an arsenal of abrasive, T-shirt-ready catchphrases (“You’re dead to me,” remains a favourite). Off-screen, he is a degree or two more subdued, even conciliatory. But he really doesn’t care if viewers think he’s Gordon Gekko’s more abhorrent cousin. He’s unlike anybody on Canadian TV because he doesn’t seem Canadian at all. “What you think of Kevin doesn’t weigh heavily on him,” says Lisa Gabriele, a former Dragon’s Den showrunner and O’Leary’s ghostwriter for Cold Hard Truth. “You could either say that’s somebody who has a quiet inner life, who is at peace, or you could say that’s a sociopath. Who knows?”

For O’Leary, television was an amusing diversion at first. Then it became a licence to print money. His name started to mean something—to both haters and hagiographers. A couple of years ago, he was handed an even bigger megaphone. Mark Burnett, producer of Survivor and The Apprentice, invited him to audition for Shark Tank, the American version of Dragon’s Den. O’Leary got the job and quickly became that particular circus’s star attraction. He’s now a bigger celebrity in the States than he is here. On ads for the show, he’s called “the Shark with the sharpest teeth.”

Every season, 29 episodes of Shark Tank are taped on the Sony lot in L.A. during two marathon sessions, one in early summer, the other in the fall. Over the course of a 12-hour day, the Sharks see a dozen pitches. The negotiations are not the expertly edited 10-minute things that finally air but protracted, hour-long sparring matches. Alex Kenjeev flies down with him and watches them all, sitting behind the camera. When O’Leary hired him to run O’Leary Ventures four years ago, Kenjeev had only seenDragon’s Den a couple of times. “I expected to be abused a little bit,” he says. O’Leary surprised him. He was patient, open-minded, didn’t take himself too seriously. The one time Kenjeev got in trouble, ironically, was when he got too aggressive with one of the entrepreneurs. “Kevin said, ‘You can’t be like that.’ And I was like, ‘What do you mean? I thought that was what we do here.’ He said, ‘No, Alex, you have to build relationships.’ ”

Last season, viewers finally saw O’Leary crack. A writer and self-described Internet entrepreneur named Maneesh Sethi tried to get the Sharks to invest in something called Pavlok, a programmable wristband that shocks its users every time they perform a bad habit. While the rest of the Sharks bailed—Mark Cuban called Sethi a con artist—O’Leary was genuinely interested. But after O’Leary tabled his bid, Sethi balked. “I would take an offer from anybody besides Mr. Wonderful,” he said. He wasn’t there to make money, he claimed, but rather to help people. He thought O’Leary would scare them off. O’Leary was stunned but retaliated quickly: “Maneesh? You’re an asshole. Get the fuck out of here,” he sniped. “Fuck you.” Sethi left the set without a deal.

O’Leary was genuinely angry and hurt. The other Sharks consoled him. After they were done taping, an on-set psychiatrist, usually there to counsel contestants, checked in on him. Talking about the episode a few months later, O’Leary was still pissed off and a bit defensive. “I’m always being myself on that show,” he said. “I’m just like everybody else. I come from a middle-class family. I feel everybody’s pain.”

A few years ago, just as Shark Tank was taking off, O’Leary and his wife split up. He was never home, and Linda didn’t like it. When he returned to Toronto, he moved into a Yorkville rental. “I did the L.A. celebrity overboard thing,” O’Leary says now, “and it got tired pretty damn fast.” After a few months, O’Leary looked around at his divorced friends, and they were all miserable. He and Linda reconciled.

Now, making up for lost time, O’Leary has become, in his own workaholic, scheduled-to-the-second way, a family man. He spends as much time as possible with his kids—a logistical nightmare given that his 23-year-old daughter, Savannah, lives in New York, where she’s a multimedia producer at Huffington Post, and 19-year-old Trevor is a McGill engineering student. (He even blew off the White House correspondents’ dinner to make time for them.) When he’s in Canada, he and Linda split their time between their five-bedroom, 150-year-old Rosedale mansion and a cottage on Lake Joseph. The Rosedale house has a wine cellar, a gym and what O’Leary calls a “technology centre,” where he can simultaneously watch five screens at a time, monitoring the markets and news networks. His workday starts early—he gets up between 4:30 and 6 a.m., and spends an hour on a stationary bike while reading a bunch of business sections (the New York Times, the Globe, the Post, the Wall Street Journal).

The O’Learys’ biggest extravagances are travel and wine. They store thousands of bottles in five cellars in four countries, and Linda helps blend O’Leary’s Fine Wines in Napa and Niagara. (They named their cabernet franc reserve after Trevor.) They travel 181 days a year, the maximum number they can be gone while still maintaining Canadian residency. They ping-pong between Toronto, Boston, New York, L.A. and Florida just about every week. In Boston, they own a house in Back Bay. In other cities, O’Leary will rent several hotel suites, one of which he’ll turn into a studio. They used to have a private plane, but O’Leary sold it seven years ago. He calls it a “shitty, shitty investment.”

When you’re an O’Leary kid, every moment is potentially a teachable one—while he and Linda fly first class, the kids go coach. As his mother did with him, O’Leary promised his children that he’d pay all their living expenses until they were out of school, and they could stay in school as long as they wanted. After that, they were on their own. No inheritance. (If they have kids, his trust is set up to do the same for them.) “I’m not a big fan of gifting huge amounts of capital to teenagers,” he says. “That’s a really stupid idea. My kids are being prepared for life after Daddy.”

I didn’t think I’d like Kevin O’Leary. I’ve seen maybe half an episode of Shark Tank, but I watched him frequently enough on The Lang and O’Leary Exchange to consider him, at best, a third-rate Bill O’Reilly wannabe. After meeting him in April, and then talking with him every few weeks after that, my feelings became more complicated. I still disagree with half of what he says, and his monumental confidence is as monotonous as it is seductive. At the same time, I found him endearing in the inscrutable, alien way that savants can be. I admire his focus, which seems superhuman. I could see it when he did his TV hits. Forgive the analogy, but with his earpiece in, mike on, eyes half-closed, brain tuned to god knows what, he’s like a shark gliding through the water. Contained, threatening. When an interviewer puts a contrarian question to him, O’Leary pounces, his voice gets louder and more bellicose, his eyes gleam, and a narrow spectrum of emotion—disdain, irritation, condescension—plays across his face.

It isn’t exactly like watching him play a role, but rather like watching him embody his brand. When you’re a brand, it’s hard to be a person. It can’t be easy to constantly project and maintain the image of mastery and triumph. “The thing you don’t prepare for is that everybody knows you but you don’t know them,” he says almost plaintively. “You reach so many people in their homes and there’s a natural tendency for them to feel extremely close to you. I get that. But it’s a very uncomfortable feeling.”

Some of those people approached us when we were getting coffee in a Financial District food court. A scruffy kid with a skateboard passed by, saw us, and yelled, “You the man, Kevin!” Seconds later, a fan approached with an iPad and asked if he could take a selfie with O’Leary. “Sure, man,” O’Leary said, breaking into a weak smile. “This must happen all the time to you,” I said. “It takes more energy to say no,” he replied with a shrug. Lenny Kravitz told him that.

The first week I met O’Leary, he’d just come back from QVC headquarters outside of Philadelphia, where he’d spent 12 hours standing in front of the cameras talking about his wine like it could cure cancer. “They’ve never sold that much wine in one day,” he says. “We launched four varietals in 20 hours and did $2.7 million.” He says he’ll be selling $20 million worth of O’Leary wines in the next two years.

Norm Hardie doesn’t go on QVC. Norm Hardie has probably never even watched QVC. And that’s one of the secrets to O’Leary’s success. He’s a shameless shill. But it’s one thing to put your money where your mouth is, it’s another to put your mouth—and face, brain and heart—where your money is. When I ask where he’s putting money these days, he happily tells me about the recent success of Wicked Good Cupcakes, a company that sells desserts in jars and one of his early Shark Tank investments. “They sold their millionth jar yesterday,” he says. “You gotta remember, I make 45 cents on every jar. That’s a $450,000 return off $75,000—pretty damn good.” A few minutes later, he tells me with Trumpian certainty about how well his ETF company is doing: “I’ve invested millions in O’Shares. Its growth is remarkable.”

Being an entrepreneur, O’Leary says with pre-emptive spin, means you’re going to fail at some point. Of the 10 most successful businesses to come out of Shark Tank, he invested in only one. He put $100,000 into a company called Toygaroo (the “Netflix of toys”), which went under a year later. He’s having trouble making back the $2.5 million he sank into Zipz Wine, a single-serving wine container. He recently sold the underperforming O’Leary Funds, and his mortgage start-up was shuttered before it really got going.

Not everyone thinks O’Leary’s as good a businessman as O’Leary does. Some, like the left-leaning economist Armine Yalnizyan, have pleaded with him to leave the country for good. Mark McQueen, the Toronto investment guru, has become both O’Leary’s self-appointed Boswell and his bête noire, taking to his blog on the Wellington Financial site to ridicule O’Leary’s every move, financial or otherwise. In January, in a blog post published after O’Leary announced his possible bid for the Tory leadership, you could practically feel McQueen’s spittle on your face: “There’s no doubt that it must appeal to him as a publicity stunt, but, even then, it’s his most outlandish one yet.”

Leary gets his hair cut every 10 days. He goes to Truefitt and Hill, in the bowels of Brookfield Place, part of a British chain that bills itself as the oldest barbershop in the world. It’s a classic O’Leary spot: there’s a patina of old-school, old-world luxury—you can get your shoes shined while you get your trim; the barbers wear ties and provide brief massages. An amiable barber named David Elgrichi has been cutting O’Leary’s hair since 2009. When O’Leary told Elgrichi that he was considering a political career, Elgrichi was overjoyed. “If anybody can do it,” he says, “Kevin can.”

Whether he can do it is less interesting than why he’d want to. O’Leary says it’s because he’s never been angrier at the way the country’s being run (he thought Harper did a pretty good job, by the way, and Mulroney was probably the best PM Canada ever had). He also proudly calls himself an opportunist, and there hasn’t been a political opportunity like this in a long time. Slow economic growth always favours politicians who focus on the economy, and it helps even more when those politicians are rich—the logic being that if they can still make money when the economy’s in the crapper, they must know what they’re doing.

When it comes to the Tories, O’Leary’s timing couldn’t be better. Trudeau has had his difficult moments, but he continues to ride high in opinion polls. The Conservative party, O’Leary says, is damaged. An obvious new leader has yet to emerge, and of those who have declared, none have O’Leary’s profile. Meanwhile, the party has moved, gingerly, toward the left on some social issues. At the CPC conference in Vancouver last May, for example, it voted to finally remove a ban on same-sex marriage from its policy handbook. O’Leary himself is in favour of gay marriage, the decriminalization of marijuana and assisted suicide.

Some Tories view his intentions with the same distaste that Bay Streeters view his TV career. He is a boorish interloper, untested and unrepresentative of the party’s values. He doesn’t speak French! He said, at one point, that he might even run for the Liberals! Sure, all the china in the shop might be broken, but they don’t want another bull in there. “He’s got nothing except being a TV star,” the Alberta MP and dean of the Conservative caucus Deepak Obhrai said in May. “It’s all about himself, not the party.” (Obhrai is also running for the leadership.)

O’Leary doesn’t care what other Tories say about him. Politically, all he cares about is economic policy. His playbook might have been a script doctored by the Canadian Taxpayers Federation—the free market rules, government drools. If he ran the country, O’Leary would have a national referendum on pipelines, put Bombardier out of its misery, and dramatically reduce both personal and corporate tax. “I think every person who makes money in this country, whether it’s a dollar or a hundred million dollars, should pay 25 per cent personal tax. Corporate tax should be 15 per cent, no loopholes, no deductions.” Because we’re taxed so heavily, O’Leary argues, our best and brightest are fleeing the country, as is any substantial foreign investment. “There are only three topics: jobs, jobs, jobs,” he says.

I’m reminded of something else Amanda Lang said about him: “Kevin has a first-class brain, and when he uses it to synthesize information, he’ll do it better than anyone. But every now and then, he reverts to an oversimplification that I know he’s too smart to believe. That’s what I think he has in common with dear Donald Trump.”

The night before this hair appointment in May, after taking his sweet time, O’Leary finally, officially, bought his Conservative party membership. “I couldn’t afford to join,” he says, dryly, “because I’m taxed too heavily by Kathleen Wynne.” (A year’s membership is less than half the price of the haircut.) Mention Wynne or, worse, Rachel Notley, and O’Leary unleashes a torrent of invective: “stupid,” “mediocre” and “incompetent.”

“Think of me as a spatula,” he says. “I’ve got to scrape the crap out of there.” A week later, on his way back to L.A., he spent a day at the Conservative conference in Vancouver. Onstage, flanked by Rona Ambrose and Stockwell Day, O’Leary did his usual shtick for an audience of amused Tories. “When I hear the word ‘capital,’ I think of money,” he said, to laughter. “That’s all that matters to me.”

In July, O’Leary called me from his cottage dock in Muskoka, where he was having his morning coffee. He and Linda built the place in 2000. It’s 10,000 square feet, with eight bedrooms and 30-foot cathedral ceilings. It has a restaurant-grade kitchen, a wine cellar carved into the granite and, of course, a microwave tower so that O’Leary can broadcast from there. The place sleeps 22, so a lot of socializing takes place—twice a year, O’Leary hosts what he calls the CEO Summit, a gathering of all the execs from his companies, past and present.

Mike Harris had been up a week earlier, and Tony Clement, who’d just announced his own leadership bid, was visiting the next day. O’Leary thought he and Clement, both guitar nuts, might do a little jamming, but really, O’Leary just wanted to see what common ground they might share. Over the next few months, he plans to invite up everyone who declares their candidacy.

It occurred to me then that O’Leary, who recently signed on for two more seasons of Shark Tank, probably isn’t going to run at all. He thinks of politicians as his employees—his taxes pay their salaries—and he never wants to be an employee again. He’d have to give up a lot of money and freedom to enter a tedious, gruelling political campaign that, to most people, is barely more desirable than scraping gum off the floor of an ice cream parlour.

A far more likely scenario is that O’Leary is going to treat every leadership candidate like he treats every contestant who’s ever stood before him on TV—he’ll get them to pitch him their platform, he’ll determine which is the smartest investment, and then he’ll lend that person, for better or worse, the power of his brand and his money. Call it Demagogue’s Den. He’s already doing this elsewhere. When Jason Kenney pulled out of the leadership race to run for the Conservatives in Alberta, O’Leary immediately offered to stump for him. “The number one mandate for Canadians is to get rid of Rachel Notley,” he says. “She’s killing this country. If she ran one of my companies, I’d have fired her a long time ago.”

The very fact that O’Leary occupies the centre of the conversation reminds me of something the late historian Tony Judt wrote: “We have substituted endless commerce for public purpose and expect no higher aspirations from our leaders.” For O’Leary, there is no higher aspiration than wealth. If making money means creating freedom, and politicians are wasting our money, that means they’re essentially taking away our freedom. Kevin O’Leary, freedom fighter? How far could the brand be extended? “Look,” he says. “I can leave, or I can fix it. I think I can fix it.”


9 thoughts on “Kevin O’Leary is a blowhard, a relentless self-promoter and, maybe, Canada’s future leader

  1. I can’t say I’m a fan of his but I will stand behind him on some of the advice he’s given on DD and ST. Entrepreneurs don’t want to hear that their ideas are failures but sometimes they need to be told that by an outside source. He might say it in the most offensive way possible but sometimes that’s all people will listen too.

    You can’t argue with his success. He’s built himself a brand, there might not be a lot behind that brand but at the end of the day people are willing to pay for his name. That’s the hardest business to build because any fault or failure reflects poorly on the entire brand.

    As for Prime Minster, he’s too short.

  2. I have read his books and I too have mixed feelings on him. Sometimes I wonder it’s not all a “act” on a online personality similar to hearing other media people sometimes saying things to get publicity. All entrepreneurs have failures… I don’t 1 know successful business who has not some but overall the article is was fair.

  3. Kevin “Stuff the Channel” O’Leary. Out of that $300-$400 million, how much is actual cash and how much is good will value of “My Brand”?

  4. O’Dreary’s gonna be PM the same way Ryan Lochte will ever be considered for a Nobel.

  5. He’d never make it as a poltician, he is too honest and blunt. Isn’t good at doublespeak and empty promises

  6. For a more realistic view of the kind of businessman he is, take a look at Mark McQueen’s running commentary at the Wellington Fund blog.

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