ICYMI, this episode with Kevin O’Leary originally aired in October of 2025. Kevin opened up about his friendship with Bethenny Frankel and a new movie with Timmy Chalamet. He also met Kylie Jenner and shared his thoughts on their relationship. Enjoy. Famous ‘Shark’ from ‘Shark Tank,’ Kevin O’Leary stops by the show today. Kevin answers all your questions from what he would do if he were starting over with just 1k to if he’s a ‘cuck’ for President Trump? Plus, losing out on a deal with Pete Davidson, the future of Tiktok, and what he predicts will happen with the stock market. Kevin also gets personal about he never plans to get involved in politics again. Then we switch gears to chat about his time working with Bethenny Frankel and if ‘Money Court’ will ever come back to TV.
Timestamps:
00:00:00 - Intro, losing out on a deal with Pete Davidson
00:11:00 - Guest ‘Sharks’ Kendra Scott, Chip and Joanna Gaines
00:20:00 - Future of Tiktok, algorithm
00:58:00 - Working with Bethenny Frankel, listener Q&A
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