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
@bertkreischer
https://www.facebook.com/BertKreischer/
