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Ask Mr. Wonderful

Published by Kevin O'Leary / Antica Productions

  • Comedy
  • Society & culture
  • Philosophy

From money and careers to sex and love - no topic is off the table when ABC's Shark Tank investor, Kevin O'Leary (aka "Mr. Wonderful") dispenses advice. Listen as O'Leary and his notable guests untie your knottiest problems with sincere, and sometimes brutal, honesty.

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On the charts

1 chart placement

Every published chart this podcast appears in, in the snapshot behind this page. Each one links to the chart it came off.

  1. Number 184PhilosophyUnited States

From the feed

Recent episodes

The latest episodes published to this podcast’s own RSS feed. Titles and descriptions are the publisher’s.

  1. Episode 6 - "Preservation over performance" (with Alex Kenjeev) from Ask Mr. Wonderful, opens in a new tab

    Dec 31, 201842 min

    Meet Alex Kenjeev, accomplished entrepreneur and venture investor. He's also Mr. Wonderful's right hand man! He does it all, from evaluating investment opportunities, negotiating and structuring each deal, and advising CEOs. Alex uncovers what happens after a deal is offered on Shark Tank (and some juicy behind the scenes). They also answer YOUR questions - like how to deal if you're a 30 year-old virgin? Produced By: Stuart Coxe, Jeremie Saunders, Taylor MacGillivary, Brian Stever and Kirsten Rudyk Sponsored By: UNTUCKit

  2. Episode 5 - "Money is actually a family member" (with Savannah O'Leary) from Ask Mr. Wonderful, opens in a new tab

    Dec 24, 201844 min

    Mr. Wonderful has an extra special guest this week (one who has zero issues with being upfront and honest with him). His very own daughter, Savannah O'Leary! Listen as she shares her millennial experience on money, work, and social media. Team O'Leary also address your questions and discuss unconventional investment advice, avoiding family drama during the holiday season, and being an entrepreneur with a young family. Produced By: Stuart Coxe, Jeremie Saunders, Taylor MacGillivary, Brian Stever and Kirsten Rudyk Sponsored By: UNTUCKit

  3. Episode 4 - "Employees are not friends, they're employees" (with Rosy and Donna from Surprise Ride) from Ask Mr. Wonderful, opens in a new tab

    Dec 17, 201845 min

    It's not everyday a Shark Tank investor follows up after you reject their offer. Sisters Donna and Rosy Khalife (founders of Washington DC's startup Surprise Ride) uncover what it's like to be on ABC's Shark Tank, and how Mr. Wonderful became involved years later. Listen as they answer investment and management concerns, to wild questions about sleeping with roommates! Buckle in, this one's a good one! Produced By: Stuart Coxe, Jeremie Saunders, Taylor MacGillivary, Brian Stever and Kirsten Rudyk Sponsored By: UNTUCKit

  4. Episode 3 - "Shirt Cockroaches" (with Chris and Aaron from UNTUCKit) from Ask Mr. Wonderful, opens in a new tab

    Dec 10, 201844 min

    This week Mr. Wonderful sits down with a couple of "shirt cockroaches" - it's the show's sponsors, Chris Riccobono and Aaron Sanandres from UNTUCKit! Learn how these two incredible entrepreneurs grew a wildly successful clothing brand in a highly competitive market. With topics ranging from brand advice to fashion consultation, this is a conversation you don't want to miss! Produced By: Stuart Coxe, Jeremie Saunders, Taylor MacGillivary, Brian Stever and Kirsten Rudyk Sponsored Brought To You By: UNTUCKit

  5. Episode 2 - "I love to go to bed richer than when I woke up" (with Barbara Corcoran) from Ask Mr. Wonderful, opens in a new tab

    Dec 3, 201848 min

    This week Mr. Wonderful sits down with long time friend and colleague Barbara Corcoran - American businesswoman, investor, syndicated columnist, author, and co-host of Shark Tank. Barbara doesn't hold back any punches as the two dive into Barbara's rise to success, past business deals with Donald Trump, and her thoughts on mixing relationships with business. Dishing out advice about choosing fame over money, debilitating acne problems, and future real estate goals. Produced By: Stuart Coxe, Jeremie Saunders, Taylor MacGillivary, Brian Stever, and Kirsten Rudyk Sponsored By: UNTUCKit

  6. Episode 1 - "Hi, it's 1950. I'm calling for Kevin O'Leary" (with Amanda Lang) from Ask Mr. Wonderful, opens in a new tab

    Nov 26, 201831 min

    Episode one is here! Mr. Wonderful welcomes his first guest Amanda Lang (former co-host on The Lang & O'Leary Exchange!) to help answer your questions about working-moms, college plans and eye-raising marriage woes. Lang is a prominent business journalist and has hosted notable shows like Bloomberg North on Bloomberg TV Canada. Listen and laugh as these two long time friends and occasional frenemies duke it out over America's thorniest problems. Produced By: Stuart Coxe, Laura Regehr, Kirsten Rudyk, and Kimberly Hacuman Sponsored By: UNTUCKit

  7. Preview: Ask Mr. Wonderful is Here! from Ask Mr. Wonderful, opens in a new tab

    Nov 23, 20181 min

    Ask Mr. Wonderful is a new podcast from Shark Tank's Kevin O'Leary! Whether you love him, or love to hate him, you can alway bet on one thing. O'Leary will always tell the truth. Join him and his guest hosts weekly as they answer your burning questions and dispense some life advice. Your friends, your family - they may not always tell you the truth. That's what Mr. Wonderful is here for. Ask Mr. Wonderful premiers Monday, November 26th!

Ranking source

Apple Podcasts rankings via the Mato Topic Intelligence Platform.

Observed September 20, 2026.

Apple and Apple Podcasts are trademarks of Apple Inc., registered in the U.S. and other countries.

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