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 Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.   Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!   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 See omnystudio.com/listener for privacy information.