Kevin O’Leary and the politics of disruption

Evan Solomon on Kevin O’Leary and the dilemma of disruption that is facing the Conservative Party

Television personality and businessman Kevin O'Leary takes part in a panel discussion of ABC's reality series "Shark Tank" during the 2013 Winter Press Tour. (Gus Ruelas/Reuters)

Television personality and businessman Kevin O’Leary takes part in a panel discussion of ABC’s reality series “Shark Tank” during the 2013 Winter Press Tour. (Gus Ruelas/Reuters)

Speaking to Kevin O’Leary the other day, just after a Mainstreet poll put the bombastic businessman as one of the frontrunners to lead the Conservative Party of Canada, I couldn’t stop thinking about Bob Dole and how he ended up going from lost elections to lost erections as the famous spokesman for Viagra. It said so much about the age of change and disruption—an age we live with still.

O’Leary is now viewed as the most politically disruptive force in conservative Canada, especially after he announced he would invest a million dollars in Alberta if NDP Premier Rachel Notley resigns.

Related: Maclean’s interviews Kevin O’Leary on his politics and his plans

Notley dismissed the idea as nothing but a publicity stunt from a rich guy on TV, and it’s since become stylish to compare O’Leary to Donald Trump. The truth is, however, when it comes to understanding the O’Leary disruption, it’s not only Trump you have to understand—though there are loads of obvious similarities —but the story of Bob Dole.

Dole was the very best of the greatest generation, brutally wounded by German machine-gun fire as he and his 10th Mountain division fought their way through the Apennine mountains in Italy. The wounds almost killed him, but Dole recovered and went on to fight his way up Washington’s political mountain. At the very peak however, as he ran for president in 1996, Dole was cut down by a silver-tongued Southerner named Bill Clinton, who could sweet-talk the skin off a peach.

Clinton was a new breed of politician, and he baffled Dole. A draft-deferring, libido-embracing, Mensa machine who consumed policy ideas and fast food in equally gluttonous amounts, Clinton was the Navy SEAL of empathy-driven retail politics. He was a political shape-shifter who could be black to the black community, Jewish to the Jews, evangelical to the Christians and a giant, smiling Bubba-huggin’ nuclear bomb to Republicans. Before Dole knew it, Clinton had disrupted the entire political establishment and founded a Clinton dynasty that may well win back the White House in 2016. Bob Dole was left bewildered, adrift on TV, where he featured in Viagra’s first-ever commercial urging men to deal with their erectile dysfunction.

Republican Sen. Pat Roberts, right, listens while former Senate Majority Leader Bob Dole speaks during a campaign stop Tuesday, Sept. 23, 2014, in Greensburg, Kan. (AP Photo/Charlie Riedel)

Republican Sen. Pat Roberts, right, listens while former Senate Majority Leader Bob Dole speaks during a campaign stop Tuesday, Sept. 23, 2014, in Greensburg, Kan. (AP Photo/Charlie Riedel)


The world had changed, but in a way only one man truly understood.

That man was Harvard professor Clayton Christensen. Within months of the presidential election, Christensen published what would become a legendary book about disruption called The Innovator’s Dilemma. In it, Christensen argued that “disruptive innovation” like new technologies would destroy huge legacy industries, even if CEOs and leaders responded with all the right rational decisions. He described how the giant steel industry slowly succumbed to the efficiencies of mini steel mills, as each product they made got outsourced or taken over in what they thought were rational cost-saving measures. In the end, though, in an effort to be more efficient and profitable, they hollowed themselves out and collapsed—death by rational self-interest, accelerated by new technologies and changing customer demands.

Christensen’s book terrified old-school CEOs, but a new generation rode the wave. Steve Jobs was so profoundly influenced by it that he used it as a virtual instruction manual for domination. Jobs grew to become a technological Genghis Khan, rampaging through the old empires of the computer, the telephone and the music player with one disruptive product after another. I interviewed Christensen years ago, as the Apple hordes were joined by the Google and Facebook tribes, and he predicted that this disruption would happen in all sectors of society, including politics. He was right. It’s still going on today.

Christensen’s idea of disruption explained the forces that ended the Cold War world, represented by Bob Dole: the American manufacturing that dominated the world; the staid banking system; politics run by the establishment. It was all over. New forces had been unleashed.

O’Leary is a classic disrupter as well, honing his skills in the high-tech business—in 1999 he sold his educational software business for more than $3 billion—and now he’s bringing it to politics. The old political rules do not apply. He’s wealthy in a way that Paul Martin was not. O’Leary’s fortune is fungible, mobile and liquid, rather than locked up in ships plying the Great Lakes. O’Leary doesn’t want to hide his excess, he wants to flaunt it. He views Canadian modesty like Jonas Salk saw polio: a curable disease.

Kevin O'Leary attends the Disney ABC Winter TCA Tour in Pasadena, Calif., in this Jan. 10, 2013 file photo. (Photo by Richard Shotwell/Invision/AP)

Kevin O’Leary attends the Disney ABC Winter TCA Tour in Pasadena, Calif., in this Jan. 10, 2013 file photo. (Photo by Richard Shotwell/Invision/AP)

I asked O’Leary on my radio show Ottawa Now how serious he was about running, trying to gauge if this was more a publicity stunt than political career, and he told me candidly that he’s already quietly forming an advisory group to build a long-term campaign strategy. “They are some of the most successful people in the country,” he said, but wouldn’t reveal their names. So the investor is already making his first political investments. And he’s a value investor, so don’t expect him to cash out quickly.

O’Leary doesn’t speak French, as he pointed out in an interview with David Akin, but when I suggested to him that this was a fatal liability he dismissed the idea as antiquated, as if bilingualism for a national leader was the political equivalent of the eight-track cassette. “I’m from Quebec,” he said, by way of explanation. If the birther issue wasn’t enough to satisfy the language cops, O’Leary went on to argue that stammering in a half-learned language was no more than political pandering. He wouldn’t do it. Period. Or actually, make that a dash: a few minutes later he admitted he may actually take French lessons, so he’s still figuring that one out. But there’s more than a year to go on that.

On security issues though, he says things that would snap Stephen Harper’s piano wires. The O’Leary Conservatives would pull CF-18 jets out of Iraq and Syria immediately, he said. No more bombing. He made a passionate series of statements about Canada’s brand being as a peacemaker, citing the great work Canada did in Cyprus starting in 1964, which has a personal resonance to him as he spent time there as a child. O’Leary says he would re-establish Canada as the world’s global peace broker, not warmonger. I can’t wait to hear him debate Jason Kenney on that.

The leader of the CPC will not be chosen until May 27, 2017. The rules are still unclear and O’Leary has yet to make any formal announcements. While he polls highly for now, these early numbers mean little. Party members may well choose a Peter MacKay, a Lisa Raitt or a Jason Kenney, if those three choose to run. They all have long histories in the party, and many, many, loyal supporters.

But politics has already been disrupted by the likes of Justin Trudeau and Rachel Notley. Outsiders who run different campaigns, with different rules and new ideas can win. If Justin Trudeau changes the electoral system, it will only further disrupt the old models. The conventional wisdom suddenly looks more conventional and less wise every day. The old establishment mandarins are starting to look more and more like Bob Dole, wondering how it all changed so fast. By the way, Dole just came out as a Trump supporter. My head is shaking.

Kevin O’Leary may not go on to be the leader of the Conservative party. But he is going to be the most disruptive force in Conservative politics since another outsider … a disruptive guy named Stephen Harper.

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