The Canadaland Guide to Kevin O’Leary

The Canadaland Guide to Kevin O’Leary

July 20, 2026 · 1h 3m · Episode 1402

About this episode

This episode explores the complex persona of Kevin O'Leary, examining whether his public image as an 'asshole' is genuine or a performance.

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…

People in this episode

Host: Jesse Brown

Topics covered

Keywords

Sponsors

oxio, Shopify

Mentioned in this episode

Organizations: McCord Museum, Tuck School of Business at Dartmouth, L.A. Business Journal, Globe & Mail, CBC, National Post, O’Leary Ventures

More episodes of CANADALAND

Explore listener stats, chart rankings, contacts and more on the CANADALAND podcast page.