July 20, 2026
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#1402 The Canadaland Guide to Kevin O’Leary
“ Kevin looked at him and said, ‘Your tears add no value to this deal.’ It was just a great fucking moment.” -Stuart Coxe, Dragons’ Den Producer
Tristan Capacchione
Senior Production Supervisor
Jesse Brown
Host & Publisher
Bruce Thorson
Senior Producer
Caleb Thompson
Audio Editor

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:

 

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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