The Canadaland Guide to Kevin O’Leary
7/20/20261 hr 3 min
Kevin O'Leary is not just a rich Canadian businessman — he's a phenomenon. He's a media phenomenon both here in Canada and in the US. And he's known for one thing: being an asshole.
But is he really an asshole? Is it just a schtick? A character? A clown that he plays on TV to entertain us all? Or is it all sincere? Does he mean all of the stuff he says? And if he does mean it, why should we believe anything he says? Is he actually an expert? In life, in business, in politics?
We tracked down the people who worked with him as his legend was being spun, including the guy that "discovered" him.
Further Reading:
- Kiddies’ Togs Manufacturing Company Ltd. — McCord Museum
- Learning from Mattel — Tuck School of Business at Dartmouth
- MATTEL – How the Giant Toy Maker Fell So Far So Fast — L.A. Business Journal
- Kevin O'Leary: He's not a billionaire, he just plays one on TV — Globe & Mail
- Richard Stursberg leaves CBC — CBC
- Lawsuits in fatal cottage country boat crash involving Kevin O’Leary finally settled. Here's what we know — National Post
- Wonder Valley — O’Leary Ventures
Host: Jesse Brown
Credits: Tristan Capacchione (Producer, Senior Production Supervisor), Bruce Thorson (Senior Producer), Caleb Thompson (Audio Editing & Production), Jesse Brown (Editor and Publisher)
Fact checking by: Julian Abraham
Additional music by: Audio Network
Photo: Philip Romano
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Clips
Transcript preview
First 90 secondsSpeaker 10:00
[whistles] Canadaland, funded by you.
Jesse Brown· Host0:03
I'm Jesse Brown, and today we bring you the Canadaland guide to Kevin O'Leary.
Speaker 3· Soundbite0:09
Kevin looked at him and said, "Your tears add no value to this deal." It's a great fucking moment.
Jeff Siskind· Guest0:15
Off-screen, he wasn't the capitalist asshole, but on-screen he played into the character that we all know.
Tristan Capoccione0:20
I still remember just interviewing him, where it's just like, "Kevin, like, why are you trying to impress me?"
Jesse Brown· Host0:24
Wait for that.
Speaker 60:25
[whistles] [upbeat music] Chef Wonderful here with a new innovation, the Bertello 16-inch rotating pizza oven. Everyone has loved my O'Leary Reserve wines for years. That's because I know you don't have to pay a fortune for good wine. Kevin, play something for us.
Speaker 70:48
Let's do it, Kev.
Speaker 80:49
Give me s- There you go.
Speaker 60:50
Let's do Blues in E.
Speaker 80:52
[upbeat music] Oh, come on, man.
Speaker 3· Soundbite0:57
Kevin O'Leary, a guy who's such an asshole that even the other people on Shark Tank thinks he's an asshole.
Jesse Brown· Host1:03
I first became aware of this Kevin O'Leary guy when I was sort of beginning my media career, when I first started working at the CBC, and it was a specific time at the CBC when the big debate at the CBC was between the old public radio ethos, the public broadcasting ethos of serving the public with the information that they need, the news that they need, the current affairs they need. A crunchy, granola, left-leaning tradition of the CBC