On Purpose with Jay Shetty
Comedian Bert Kreischer: My Constant Battle with My Inner Critic (Overcoming Anxiety, Chasing Approval & The Pressure to Be Funny)
Wed, 14 May 2025
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 | FacebookSee omnystudio.com/listener for privacy information.
Chapter 1: Who is Bert Kreischer and what is his comedic background?
With six Netflix specials to his name, Burt's latest special, Lucky, was number three in the top 10 most watched TV shows on Netflix. Burt continues to sell out arenas and is also the co-host of Two Bears, One Cave, one of the top comedy podcasts worldwide. Burt's energy, storytelling, and ability to connect with audiences is unmatched, and I can't wait for you to hear it.
Welcome to On Purpose, Burt Crusher. But you know what's funny? What? I still remember the flight we were on together and we sat down next to each other. And I'm going to sound like such a douche for saying this, but I have to say you were the nicest person in the world. And you were so kind and you were like, I can't remember how you started the conversation.
Maybe you can, but you were like, I really like your stuff.
Yeah.
I love what you're doing. And I was the idiot who's living under a rock. Yeah. No. It was like, I think I know what you do. It's really cool, but I don't know. And then I came back and I told my team, I was like, I was sitting next to Bert Kreischer, like, you know, we're texting. He's such a nice guy. He was so wonderful. And they were like, you met Bert Kreischer? They're like, he's amazing.
He's funny. And I was like, I'm the idiot who doesn't know. And it was just one of those moments where like, You were so kind, you were so endearing, you were so sweet. And I was really touched by that interaction. I never in a million years thought the number one partier in the world and me would have something in common.
You've got a weird thing that like usually only like Reese Witherspoon or Jennifer Aniston get where you're strikingly attractive. So when I sat down next to you, I was like, whose eyes are these? And then I was like, wait, I know him. I was like, oh, shit. Oh, shit. This is Jay Shetty. I've listened to so many of your interviews. You're so good. You're so good. And so, yeah, I was so excited.
And then I get told by like my friends with a professional wrestler, Cody Rhodes. And he said, you know, when I met you, I've never seen more of a pro wrestler personality. Like you explain yourself within a sentence and then explain why you should like me. And I'm like, but it's, yeah, I'm a talker on a plane.
And you were so funny already. And I was like, oh, this guy's hilarious. Cause you were like. you know what, you're good, but I'm a pretty big deal too. You know, you're cracking. And I was cracking.
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Chapter 2: How did Bert Kreischer's childhood shape his comedic style?
I got a good one. All right. I'm going to say real names, too. I sat next to a woman, first class, when I was just married with kids. I had Isla and Georgia, but they were still really young. And the woman was coming back from Tibet. And she had the beads on and henna all over. Hot, attractive. Probably a little older than me. Maybe I'd say 43. I was 30, maybe six at the time.
And we start having drinks, and we're talking. And then she says, what are you doing when you land in LA? I said, I'm going home. She goes, don't. Come to my place. Let's have sex. I said, what? She goes, I'm out of divorce. That's why I went over to Tibet. I'm a little lost, but I'm just looking to get. And I went, okay. I said, listen, I'm married. And so you got the wrong guy.
I go, but I got the right guy for you. She said, really? And I said, trust me. Can you just trust me? So we land and I call Mike Young. He's a real name. I go, Mike, you want sex tonight? And he was like, with you? I go, no, I got a beautiful woman, 43 years old. And he goes, yeah, give her my number. She gives her another number. They meet at the comedy store. They go back to her place.
They have sex. They've never talked again. And I was like, boom, man, slam dunk. I got great ones. I sat next to Ric Flair one time and we both drank identically. We both ordered drinks for our wives and ourselves and then drank our wives drinks and then drank our drinks. And I was like, Ooh, Ric Flair and I drink alike. I had a girl walk me to my room in Soho the other night.
She was like, Hey, I'm going to come to your room. I was like, and I got her to the door and I said, listen, I was really drunk. I go, listen, It's very sweet of you, but I'm married, and I'm happily married, and I don't cheat on my wife. And she had this weird look on her face, and I woke up the next morning. I called my wife. I told her, I go, I just, I'm such a great guy.
And then there was a note under my door, and it was like, Bert, I wasn't trying to have sex with you. You were too drunk. You couldn't remember what room you were in, and you didn't have a key. I just wanted to make sure you got home safe. I was like, oh, I shot down a good Samaritan? Yeah.
How does your wife react to stories like that when you're like calling her out?
I've been doing that our whole marriage. Our marriage is based on fun and laughter. I mean, for real, it is probably the funnest. It's by far, it's the funnest relationship I have in my life. We joke nonstop. We're in couples therapy right now. And as we walk out, I decide who won or who lost. Like, it's just a blast. And I've been doing that ever since, ever since, uh,
We were a young married couple. I'd text her. I'd go, just so you know, I'm getting jocked. And then I sent a picture, and Leanne's like, she's got a lazy eye. And I'm like, oh, man. Yeah. And she gives it back to you, too? Oh, yeah. Oh, yeah. Her and my daughters are just bullies. Like, bullies. Like, they've never... They call me Baby Walrus. They've never...
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Chapter 3: What was Bert Kreischer's relationship with his father like?
Kamen comes in. He dives in. A dog grabs his leg. I take off. And I'm practicing the story. And then I get there, and they'd be like, hey, tell us about the fight. And I'd be like, OK, got to pivot. Here we go. And I remember the first time I said a line, that like worked well, I said, dude, he got knocked out. I mean, this punch started in Miami and ended in Washington State.
And they were like, oh, like it was just, it was like storytelling was our thing. And if you could tell a good story, like Beach Week, you came up to the room Everyone wanted to know if you hooked up with that chick and you had to have a story about it. Yeah. Oh yeah. I remember one guy came up older kid and he was like, yeah, I didn't have a condom. So I used a plastic bag and we're like, what?
Like just wild stories. Yeah. And then when I got to Florida state, uh, that's when I started realizing I was funny.
I went to an all boy school too. But what I realized was that a lot of the guys had imaginary girlfriends. So a lot of the stories were just made up. And when you'd figure out that Felicity wasn't real because that was an American girl's name off a TV show and not a girl's name in England. Like you'd never, there's no one I've ever met in England called Felicity.
And then one of our guys was dating a girl called Felicity. We're like, he's been watching too much American Pie. Like that's like the feeling we'd get.
Girls were a perfect example. I was so painfully serious about losing my virginity. I mean, I was dialed in. It was my only focus. And then when I did, it was such a tragedy that that story became, I remember sitting down and they're like, bro, tell the story. And all of a sudden there's like three deep. And the story I've told it on, this may not be the right setting for it,
But I'll just say it was fast and I did it wrong. And I mean, and there were like dudes standing three people deep to hear this story. And then, you know, we had two lunches. So the next people come in, it was Ty Rodriguez, like, tell it again. And I mean, everything was like a tragedy, like a comedy of tragedies for me.
And you've never reconnected back with this person?
The woman? The woman, yeah. You know her? Yeah, I know her very well. No way. That's Tampa though. I know her. I know her brother. Her dad just recently passed. Her dad was a legend. Her dad was a legend. I got to say this and, you know, She cheated on me at prom with my best friend and we had to go spend the night at her house.
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Chapter 4: How did Bert Kreischer break into comedy and gain his father's approval?
At the Amelie, yeah.
No.
After all these years. After all these years, I did the Amelie, which is the arena in Tampa. And I said, yo, if you're going to, you should come and see me here. I understand like comedy clubs, but you should come to the arena. It's a big deal, dad. He got there. And I don't think he realized what was happening for real.
Like he knew I was doing a show there, but he called me and he goes, Wade Boggs is here. Wade Boggs is like our hero playing baseball growing up. I said, yeah, I know. I put him in your box. And he goes, no, but he's here. Do you think he knows you? And I said, daddy's at my show. He goes, I just saw Mike Alstott, football player. I go, yeah. And he goes, do these people know you?
I said, dad, I'm the reason they're here. And then he came backstage and Derrick Brooks, who's a legend, played at Florida State, played at the Bucs, is backstage talking to my dad. My dad's staring at Derrick Brooks going. And he goes, and Derrick goes, can you believe how far birds come? He's doing the Emily and I, he goes, I was at his first show at Potbelly's and Derrick Brooks leaves.
My dad goes, buddy, Derrick Brooks knows who you are. I was like, yeah, I know dad. We just spent time with him. He knows who you are too now. But yeah, my dad just, he just, that was the first time he saw me to stand up. What did he say? I got to be honest with you. I think it makes him uncomfortable.
Like I think he kind of half looks and half, like I don't think he, I don't think he laughs a lot at it. I don't know. I mean, he says, he goes, you're good. Like, but he, I make him uncomfortable. I had a great Shaq joke that Shaq wanted me to put in the special. It's, dare I say, borderline racist. But Shaq and I talked. It made us laugh. And Shaq's like, you've got to put that in the special.
And my dad's like, that does not go in the special. And I was like, Dad, Shaq says it's OK. And he goes, I don't give a shit. I am not comfortable with that joke. So I took it out. Shaq's like, you took it out because of your dad? Yeah, what? But I got a better Shaq joke now.
Oh, OK.
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Chapter 5: How has Bert Kreischer's family influenced his comedy?
Will Smith. Yeah. Will Smith. Well, I got a deal at like 26 years old. I've been doing standup on my 26th birthday. I was in New York and I was just partying. I wasn't doing standup. I've been there for a couple months and I got hammered the night before and it was my birthday. And my phone rang at like eight o'clock in the morning, nine o'clock in the morning. And I saw it was my dad caller ID.
And I said, you know, I'll answer it. Let him say happy birthday. And I'll go back to sleep. I answer it. And he says, you are a tremendous piece of shit. And I'm like, what? I go, dad? And he goes, yeah, yeah, it's your dad. And he goes, you are worthless. You have no humility. You're doing nothing. He goes, I just perjured myself in court because of you. The judge said, Al, how's your son doing?
And I said, great. That is a lie. You are not doing great. And you never will do great. I have failed you as a father. I gave you no humility. I taught you no life lessons. You never had to work for anything. Things came easy to you. And I'm telling you. And I said to him, I go, yeah. It's my birthday. And he goes, I know what day it is. He goes, I gave birth to you.
We were there when you got born. And he goes, I'm telling you. And I was like, dad, I go, well, okay. So what do I do with this? He goes, nothing. He goes, I'll foot the bill, be a party boy. And I was like, well, I want to, I want to, I don't want you to feel this way about me. And he goes, no, you should not want to feel this way about yourself. And I said to him, what can I do?
He said, well, if you're serious about comedy, then you'll go to that club tonight and you'll do whatever you can to get on stage. You'll go to that man and you'll say, my name is Bert Kreischer. I'd like to be a standup. I'll clean up. I'll mop up. I'll flip burgers. I'll stand up. I'll do whatever you need, but I need an opportunity.
I said, I remember saying to him, I go, I can't do it today, tonight because I have a party planned. He was silent. He just goes, you have a party? He goes, you don't deserve a party. What are you throwing a party for? You're a failure. You go to that club tonight. You take yourself to dinner. I want you to write down some goals.
And then you, after that dinner, you go to that club and you tell whoever you need to, you'll do whatever you can and you'll do it for free. And I said, dad, that's not how it works. I remember him very clearly saying, hey, for some young black kid in Harlem, that's how it works for him. Do you know why? Because he has humility and he knows how to get what he wants. That's how it works for him.
It doesn't work for you because you're white and you feel like everything should be given to you. And I went, okay. So I said, all right, I'll do it. So I didn't, I took myself to a restaurant on 7th and Bleeker. And then I wrote down 26 goals that I had planned for that year. So I was turning 26. I went to the Boston Comedy Club. I met a guy named Louis Schaefer and I told him,
exactly what my dad said. My name's Bert. I want to do this. Any advice, anything you do to get me on stage? And Louis Schaefer said, you should move back to Tampa. And I went, what? He goes, you're not going to be a comedian in New York. You don't have what it takes. And I went home, almost like victorious. I was like, so dad, this is how it works. I told you I was right.
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Chapter 6: What is Bert Kreischer's approach to handling fame and family life?
It was a very special moment for us. It's been 15 years for me in this career. Finally, things are starting to shift into a different level.
Listen to Hasta Bajo on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
A hundred percent. I mean, a lot of my friends, like, the pandemic hit. And my brain was like, that doesn't mean we can't do stand-up. And then I know the country shut down. And I went, I'll figure it out. And so I came up with a type of touring, outdoor comedy festivals, where I took drive-in movie theaters, and I plugged into their system. We showed it up on the big screen.
We shot it with four cameras. All the feeds went into the car so everyone could stay socially distant. And I did, I think I did 30 cities. I think I maybe did 30 cities, 60 shows, 62 shows. I toured all through the pandemic. That's just the way my brain works is like, just because you say no, that doesn't mean, look, you got to do it. You got to work. Don't just take the foot off the gas.
What I love about the earthquake story too, it's like what your dad said. If you didn't put yourself under that pressure, you wouldn't have found that great new take.
If you're a dad right now and you're listening, this is the only takeaway you need. My dad, whether it's true or not, always told me, you love pressure. Buddy, when all the chips are on the table, you perform your best. I don't know what it is about you, but you love the pressure. You just love it.
And I'll tell you, my whole baseball career, if we were down, man off first and second, we're down by two runs, that's when I performed it. When we faced the fastest pitcher we ever faced, that's the guy I hit the best off of. And I'll tell you is, in standup, I've always done best when the most pressure's on me. I need to do secret time. First show, I bomb. I'm only doing two shows. I bomb.
I bomb. I hadn't bombed with this hour ever, and I bombed. The crowd had had to wait in the rain. We had a power shortage. It just, it was horrible. And I'm nervous. I got one more show. This is my first Netflix special. I got one more show, and I'm sitting in the green room. And Leanne just echoes my dad. She goes, well, you know you love pressure. This is when he's going to perform the best.
Sit back, everybody. And man, that show, I mean, best stand-up show I've ever had in my entire career was that one show. That was murderous.
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