Something's not right. The Kevin O'Leary of Dragons' Den and Shark Tank TV fame is a fabulous tycoon. Shouldn't we be meeting in a palace or a yacht, the kind of place that lets the world know you've hit money-making's major leagues?
His rental unit is by no means shabby. It's a sprawling apartment that looks across Toronto's high-end Yorkville district, and though it sits above a shop, the shop is Pusateri's Fine Foods, the perfect takeout place for the plutocrat on the go. Not bad for a guy whose hard-drinking Irish salesman father died young, whose Lebanese-born seamstress mother found peace only when she married an Egyptian academic who aspired to help the global poor.
But this definitely isn't the gilded Bridle Path château that would suit his TV swagger.
“Excuse the mess,” he says as we walk past squash racquets leaning against a bare wall. There isn't much of a mess.
He's got a few treasures on display. There's a personally autographed Gibson Les Paul, the pride of a vast guitar collection; an ancient mosaic from Antioch, not far from the island of Cyprus where he spent happy years while his stepfather worked for the International Labour Organization; a vintage Leica M3 – Mr. O'Leary once aspired to be a fashion photographer; and a Chagall work titled Greed, though the debauched figure in the etching looks nothing like its robust, squash-playing owner.
The rest of the sparse flat looks almost unoccupied. Kevin O'Leary is selling a dream to his business-show followers and to the investors who have handed over their money to O'Leary Funds, a venture that has leveraged his fame and grown from zero to $1.5-billion in 30 months. But something is missing at the core of his legendary life.
The entrepreneur who revels in being “the mean one” on Dragons' Den, who delights in being called “asshole” by strangers, is trying out his Don Cherry imitation. He's promoting his new memoir, Cold Hard Truth, which means sending an I-know-best message to budding capitalists.
“Money equals freedom,” he declares while chewing on gummi bears. “Have one if you'd like,” he says.
When not on-message, he is surprisingly subdued, nothing like the ranter on CBC's The Lang & O'Leary Exchange who excoriates everything polite and Canadian.
“You may lose your wife, you may lose your dog, your mother may hate you,” he says, returning to his money-centred sales pitch. He likes to say he combines his father's confident Irish patter with the Phoenician trader mentality from his mother's side. And then he adds wisdom gleaned from his own success story. “None of those things matter. What matters is that you achieve success and become free. Then you can do whatever you like.”
Kevin O'Leary does exactly what he likes. That's the image anyway. But the man who's enunciating this mantra is more conflicted than you would guess from the bravado. His promise has come true. He lost Linda, his wife of 21 years. Or she lost him.
Marriages are often collateral damage in the relentless drive to get rich. But there's no mention of the breakup in Cold Hard Truth.
“When I wrote the book, I was married,” he offers. We've been chatting for almost an hour before word of his separation slips out. He has talked about the storage business he built up, about how miserable he was when he was paid $5-million not to work in a non-compete after he sold an educational-software business called The Learning Company to Mattel for $3.5-billion in 1999. “I went to every beach around the world, I saw them all, I partied everywhere, I was bored out of my mind.”
He had made millions of dollars himself in the merger with Mattel, which took place just before the bottom fell out of the dot-com business. Ever since, he has enjoyed a reputation for having the magic touch.
“He's certainly one of the luckier guys on the Street,” says a Bay Street financier who is more reticent than Mr. O'Leary about taking potshots. “Everyone admires a guy who cashed out at the right time.”
