Reinvention and Resilience in Comedy

Do you ever feel like you need to be funny to be liked?

How do you handle pressure to always “perform” for others?

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.

In this interview, you'll learn:

How to Stay Humble While Chasing Big Dreams

How to Raise Kids Who Keep You Grounded

How to Keep Showing Up Even When It's Hard

How to Use Vulnerability as a Superpower

How to Manage Anxiety Without Shame

How to Turn Criticism into Growth

How to Stay Grateful Through Every Stage of Success

This episode is full of laughs, a few tear-jerking moments, and plenty of insight into what it really means to show up, be yourself, and keep going, even when it’s hard. 

With Love and Gratitude,

Jay Shetty

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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:

Bert Kreischer | Website

Bert Kreischer | Instagram

Bert Kreischer | X

Bert Kreischer | YouTube

Bert Kreischer | TikTok

Bert Kreischer | Facebook

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