EPISODE · Jul 20, 2026 · 1H 2M
The Canadaland Guide to Kevin O’Leary
from CANADALAND
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 MuseumLearning from Mattel — Tuck School of Business at DartmouthMATTEL – How the Giant Toy Maker Fell So Far So Fast — L.A. Business JournalKevin O'Leary: He's not a billionaire, he just plays one on TV — Globe & MailRichard Stursberg leaves CBC — CBCLawsuits in fatal cottage country boat crash involving Kevin O’Leary finally settled. Here's what we know — National PostWonder Valley — O’Leary VenturesHost: Jesse BrownCredits: Tristan Capacchione (Producer, Senior Production Supervisor), Bruce Thorson (Senior Producer), Caleb Thompson (Audio Editing & Production), Jesse Brown (Editor and Publisher)Fact checking by: Julian AbrahamAdditional music by: Audio NetworkPhoto: Philip RomanoSponsors: oxio: Head over to https://canadaland.oxio.ca and use code CANADALAND for your first month free! Shopify: Sign up for your one-dollar-per-month trial today at https://shopify.caBetterHelp: Visit https://betterHelp.com/canadaland today to get 10% off your first month.Can’t get enough Canadaland? Follow @Canadaland_Podcasts on Instagram for clips, announcements, explainers and more.If you value this podcast, support us! You’ll get premium access to all our shows ad free, including early releases and bonus content. You’ll also get our exclusive newsletter, discounts on merch at our store, tickets to our live and virtual events, and more than anything, you’ll be a part of the solution to Canada’s journalism crisis, you’ll be keeping our work free and accessible to everybody. Hosted on Acast. See acast.com/privacy for more information.
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The Canadaland Guide to Kevin O’Leary
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