Jay Shetty Podcast

Bert Kreischer: The Truth about ''The Machine'' Story..

In this candid, hilarious, and unexpectedly moving episode of On Purpose, Jay sits down with comedian, actor, and podcast superstar Bert Kreischer—famously known for his shirtless stand-up and his ability to keep audiences laughing nonstop. This conversation goes way beyond the jokes as Jay and Bert dive deep into the real stories behind the spotlight, revealing the layers of vulnerability, self-doubt, and emotional growth that make Bert more than just a party-loving comic. Bert shares what it was like growing up with a tough, old-school dad who believed in powering through pain and never showing weakness. That mentality helped shape Bert’s work ethic but also left him carrying emotional weight for years. In one of the most touching moments of the episode, Bert shares how a simple, unexpected conversation with his dad, while they were both high on edibles, changed everything, helping them finally see each other clearly and connect on a deeper level. With Jay’s thoughtful guidance, they unpack Bert’s real-life struggles with anxiety, chasing approval, and feeling like you’re never enough, things so many of us can relate to. Bert is refreshingly honest about his mental health, his parenting ups and downs, and what it's like trying to stay grounded while raising two sharp, hilarious daughters who aren’t afraid to call him out. What We Discuss: 00:00 Intro 02:45 The Wildest Plane Stories You’ve Ever Heard 04:25 Why a Marriage Built on Laughter Works 06:01 When Your Family Becomes Your Funniest Critics 07:16 Were You Always the Funny One? 09:08 How Bert Mastered the Art of Storytelling 14:35 Growing Up with a Tough-Love Dad 17:56 What It’s Like Seeing Your Parent Cry for the First Time 20:40 Realizing Your Parents Are Human Too 23:36 When Your Dad Realizes He Can Use Your Fame 24:35 What It’s Like to Share Your Success with Your Parents 29:05 The Lifelong Quest for a Parent’s Approval 35:08 How a 6-Figure Deal with Will Smith Changed Everything 37:20 The Moment You Know You Have to Chase Your Talent 42:50 Embracing the Power of Pressure 44:09 Is There a Pain You Can’t Laugh Through? 47:06 Letting Your Kids See You Cry 49:56 Why the Way You Tell a Joke Matters 51:43 How Your Kids Really See You 54:05 The Challenge of Uninterrupted Family Time 56:51 Just Show Up and Do the Work 01:01:33 Success Was Never a Straight Line 01:07:24 Don’t Let Greatness Become Familiar 01:11:12 Living with Anxiety When Life Doesn’t Slow Down 01:17:26 Building a Healthier Relationship with Alcohol 01:19:29 How Tracking Your Fitness Can Change You 01:22:00 Bert on Final Five Episode Resources: https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me https://www.bertbertbert.com/ https://www.instagram.com/bertkreischer https://x.com/bertkreischer https://www.youtube.com/@bertkreischer https://www.tiktok.com/@bertkreischer https://www.facebook.com/BertKreischer/

BKBert KreischerguestJSJay Shettyhost

May 14, 2025·1h 36m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Plane-seat meetup, mutual admiration, and Bert’s “talker on a plane” energy

   Jay and Bert open by recalling the flight where they met and instantly clicked. They riff on first impressions, confidence vs. charm, and how Bert’s personality “explains itself” immediately.

2. 2

   Wild plane stories: temptation, misunderstandings, and celebrity drinking (Ric Flair)

   Bert launches into outrageous plane and travel stories that highlight his comedic honesty and marriage boundaries. The stories mix absurdity with a recurring theme: he’s loyal, but often comically clueless in the moment.

3. 3

   Marriage built on laughter: playful roasting, therapy-as-competition, and family “bullies”

   Bert explains that his marriage works because it’s rooted in constant joking and shared humor. He describes how his wife and daughters roast him relentlessly, creating a culture of playful honesty at home.

4. 4

   Not the class clown: serious kid energy that accidentally read as funny

   Bert says he wasn’t the obvious funny kid—he was intensely serious, which made his behavior unintentionally comedic. He shares early moments where his desire to be “cool” became the joke.

5. 5

   How Bert learned storytelling: all-boys school “table currency” and crafting lines

   Bert credits his all-boys Catholic high school for developing his storytelling chops. Social status depended on holding attention at the lunch table, so he practiced structure, punchlines, and timing daily.

6. 6

   Tough-love fatherhood: ‘don’t cry,’ work ethic, and a blunt worldview

   Bert describes a dad who loved him but showed it through toughness, duty, and emotional restraint. The upside became grit; the downside became fear, anxiety, and a lifelong hunger for approval.

7. 7

   Seeing his dad cry & the ‘weed popcorn’ breakthrough: fear, love, and reconnection

   Two moments shift Bert’s understanding of his father: seeing him cry, and later a vulnerable conversation while high that reveals his dad’s fear of losing him. That honesty leads to health tests and a smoother relationship.

8. 8

   Approval-seeking, fame shifting the power dynamic, and sharing success with parents

   Bert admits his career has been fueled by wanting his dad’s approval. As he becomes successful, his dad struggles with not having all the answers, while also enjoying the trickle-down recognition.

9. 9

   Will Smith deal as a turning point: humility, persistence, and ‘be yourself’

   Bert recounts a brutal birthday call from his dad that forces him to pursue comedy with discipline. Persistent nightly asking gets him stage time—then Will Smith discovers him, changing both his career and how his dad sees him.

10. 10

    Pressure as fuel: following ‘unfollowable’ acts, bombing, and performing best when it counts

    Bert explains how pressure reliably brings out his best work, a belief reinforced by his dad and wife. He shares moments where high stakes created breakthroughs in performance and career decisions.

11. 11

    Laughing through pain: grandmother’s funeral, family grief, and letting kids see you cry

    Bert explores humor as a coping tool and how grief and love can coexist with laughter. He shares poignant stories about family loss and parenting differently than his dad by allowing emotion in front of his daughters.

12. 12

    Comedy craft and permission: what’s allowed about family material & telling jokes with love

    Bert explains the rules for joking about his wife and family: it has to be funny, not mean, and delivered with clear affection. He also reflects on the responsibility of jokes that accidentally exclude or hurt.

13. 13

    Kids and fame: wanting ‘just my dad,’ college visits, and boundaries with fans

    Bert describes how recognition impacts his daughters, especially during vulnerable moments. He struggles to say no to fans, while his kids sometimes feel they’re competing with the public for his attention.

14. 14

    ‘Lucky’ special, the dog-story closer, and creative anxiety about relevance

    Bert details the risk of ending a special with emotional material and his fear of being mocked for it. The audience response—laughing and crying—validates the creative leap and eases his anxiety about staying relevant.

15. 15

    Mental health, coping tools, alcohol, and fitness tracking: ‘do today a little better’ + Final Five

    Bert opens up about anxiety, intrusive thoughts, and the coping strategies he uses—some healthier than others. He discusses alcohol as ritual/permission, tracking fitness with Whoop, and closes with Jay’s Final Five questions.