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:
Intro
The Wildest Plane Stories You’ve Ever Heard
Why a Marriage Built on Laughter Works
When Your Family Becomes Your Funniest Critics
Were You Always the Funny One?
How Bert Mastered the Art of Storytelling
Growing Up with a Tough-Love Dad
What It’s Like Seeing Your Parent Cry for the First Time
Realizing Your Parents Are Human Too
When Your Dad Realizes He Can Use Your Fame
What It’s Like to Share Your Success with Your Parents
The Lifelong Quest for a Parent’s Approval
How a 6-Figure Deal with Will Smith Changed Everything
The Moment You Know You Have to Chase Your Talent
Embracing the Power of Pressure
Is There a Pain You Can’t Laugh Through?
Letting Your Kids See You Cry
Why the Way You Tell a Joke Matters
How Your Kids Really See You
The Challenge of Uninterrupted Family Time
Just Show Up and Do the Work
Success Was Never a Straight Line
Don’t Let Greatness Become Familiar
Living with Anxiety When Life Doesn’t Slow Down
Building a Healthier Relationship with Alcohol
How Tracking Your Fitness Can Change You
Bert on Final Five
Episode Resources:
Bert Kreischer | Website
Bert Kreischer | Instagram
Bert Kreischer | X
Bert Kreischer | YouTube
Bert Kreischer | TikTok
Bert Kreischer | Facebook
See omnystudio.com/listener for privacy information.
