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Jay Shetty PodcastJay Shetty Podcast

Bert Kreischer: The Truth about ''The Machine'' Story..

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

Bert KreischerguestJay Shettyhost
May 14, 20251h 36mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:45

    Intro

    1. BK

      My dad's mentality is, "If you don't get on stage, if you don't show up to work, all the stuff that could possibly make your life great just disappears.

    2. JS

      Mm-hmm.

    3. BK

      No matter what, you show up. Get out there and grind. The number one health and wellness podcast. Jay Shetty.

    4. JS

      Jay Shetty.

    5. BK

      The one, the only Jay Shetty.

    6. JS

      [laughs] Bert, you know what's funny?

    7. BK

      What?

    8. JS

      I still remember the f- flight we were on together, and we sat down next to each other, and I'm gonna sound like such a douche for saying this, but I have to say, you were the nicest person in the world.

    9. BK

      Oh. [laughs]

    10. JS

      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."

    11. BK

      Yeah.

    12. JS

      "I love what you're doing." And I was the idiot who's living under a rock. [laughs]

    13. BK

      No.

    14. JS

      And who was like, "I think I know what you do. It's really cool. Like, 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, and they were like, "You met Bert Kreischer?"

    15. BK

      [laughs]

    16. JS

      They were like, "He's amazing. He's funny. He's in..." 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, and I was really touched by that interaction. I never in a million years thought the number one podcaster in the world and me would have something in common, so.

    17. BK

      You've got a weird thing that, like, usually only, like, Reese Witherspoon or, or Jennifer Aniston get, where you're strikingly attractive.

    18. JS

      [laughs]

    19. BK

      So, so when I sat down next to you, I was like, " Whose eyes are these?"

    20. JS

      [laughs]

    21. BK

      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, uh, yeah, I was so excited. And then I get told by, like... My... I'm friends with the professional wrestler Cody Rhodes, and he said, "You know, when I met you, I've never seen more of a pro wrestler personality."

    22. JS

      [laughs]

    23. BK

      Like, you, you explain yourself within a sentence, and then d- and explain why you should like me, and I'm like... But it's, I, yeah, I, I- I'm a talker on a plane.

    24. JS

      And you were so funny already, and I was like, "Oh, this guy's hilarious," 'cause you were like, "You know what? Like, you're, you're, you're good, but I'm a pretty big deal, too, you know?" You were cracking... [laughs]

    25. BK

      [laughs]

    26. JS

      And I was cracking.

    27. BK

      That doesn't sound like me. [laughs]

    28. JS

      And I was cracking. But it was, it was endearing.

    29. BK

      No, yeah.

    30. JS

      Like, I want to put it out there. Like, I'm not trying to overcompensate, but it wasn't arrogance. It was like I was laughing with you.

  2. 2:45 – 4:25

    The Wildest Plane Stories You’ve Ever Heard

    1. JS

      ask you, you've probably had some crazy plane stories.

    2. BK

      Oh, yeah.

    3. JS

      I want to know what's, what's the craziest plane story you've ever had, seeing as that's where we met?

    4. BK

      I got a, I got a good one.

    5. JS

      All right.

    6. BK

      Uh, I'm gonna say real names, too. I sat next to a woman, first class, when I was just married with kids. Like, I had Isla and Georgia, but they were still really young. And the woman was coming back from Tibet, and she was, like, 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 6 at the time. And we start having drinks, and we're talking, and then she says, uh, "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."

    7. JS

      [laughs]

    8. BK

      I said, "What?" She goes, uh, "I've been... 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, uh, that's, you got the wrong guy." I go, "But I got the right guy for you."

    9. JS

      [laughs]

    10. BK

      She said, "Really?" And I said, "Trust me. Can you just trust me?" So we land, and I call Mike Young, 'cause he's a real name. [laughs] I go, "Mike, you wanna have 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 the number. They meet at The Comedy Store. They go back to her place. They have sex. They've never talked again.

    11. JS

      [laughs]

    12. BK

      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.

    13. JS

      [laughs]

    14. BK

      And I was like, "Ooh, Ric Flair and I drink alike." [laughs]

    15. JS

      [laughs]

    16. BK

      I had a girl walk me to my room in Soho the other night. She was like, "Hey, I'm gonna 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, I'm married,

  3. 4:25 – 6:01

    Why a Marriage Built on Laughter Works

    1. BK

      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... I called my wife. I told her. I go, "I just... I'm such a great guy."

    2. JS

      [laughs]

    3. BK

      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."

    4. JS

      [laughs]

    5. BK

      "I just wanted to make sure you got home safe." I was like, "Oh, I shot down a good Samaritan?" [laughs]

    6. JS

      [laughs] How does your wife react to stories like that-

    7. BK

      Oh-

    8. JS

      ... when you're, like, calling her up?

    9. BK

      I've been doing that her- our whole marriage. Our mi- our marriage is based on fun and laughter.

    10. JS

      Yeah.

    11. BK

      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.

    12. JS

      [laughs]

    13. BK

      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 go, "Just so you know, I'm getting jocked." And then I send a picture, and Leanne's like, "She's got a lazy eye."

    14. JS

      [laughs]

    15. BK

      And I'm like, "Oh, man." Yeah.

    16. JS

      And she gives it back to you, too?

    17. BK

      Oh, yeah. Oh, yeah. M- her and my daughters are just bullies. Like, bullies. Like, they've never... They, they called, they call me Baby Walrus. They've, they've never... They bust my balls harder than anyone I've ever met.

    18. JS

      Yeah.

    19. BK

      Other than my two sisters.

    20. JS

      Yeah.

    21. BK

      The women in my life run my life.

    22. JS

      Isn't that the best? Like, my wife, we just did this video, and it was planned by my team, but we did this video where my wife rated my looks on the red carpet for the last seven years or however long it's been.

    23. BK

      Oh, that's great.

    24. JS

      And, oh, dude, I've got some embarrassing red carpet looks, and my wife does not hold back in this video. She just goes for it, and she's got so much banter, and she's

  4. 6:01 – 7:16

    When Your Family Becomes Your Funniest Critics

    1. JS

      got so much sass.

    2. BK

      [laughs]

    3. JS

      And it's like all the comments are like, "She's a savage." I'm like, yeah, you think she looks cute and all this stuff.

    4. BK

      [laughs]

    5. JS

      But this woman can, like, go in, and it's... And, and, and I can, I mean, I can, I can attest to the fact that those are terrible looks, but.

    6. BK

      So Baby Walrus startedOr Chat Thread Baby Walrus, and it was pictures where they thought I was cute

    7. JS

      [laughs]

    8. BK

      And it's, like, the worst pictures ever, and it's like one of them's me on a surfboard covered in, uh, in, like, in sunscreen, and I just am sitting crisscross applesauce on a s- on a surfboard. And I look fat, and I got a hoodie on. It's so bad, but it's them sending pictures where they think I look cute, but I look like an idiot.

    9. JS

      [laughs]

    10. BK

      Yeah.

    11. JS

      And so are they paying you, or they think you look cute?

    12. BK

      The, I... I mean, the picture on Baby Walrus is horrible.

    13. JS

      Let's see. We're gonna have to get this for the edit as well so everyone on YouTube can see it.

    14. BK

      It's the one of me on the surfboard.

    15. JS

      Oh, yeah, yeah, yeah. I see it. [laughs]

    16. BK

      And they're all just pictures of me looking horrible.

    17. JS

      Oh, God, the worst.

    18. BK

      You'll see.

    19. JS

      We'll get back to the family in a second, but, uh, I wanted to... Were you, were you always the class clown? Was this always natural for you? Were you the guy who could make everyone laugh and get attention? Was that who you were?

    20. BK

      No. I was like, uh, dare I say like painfully serious. Like, I, I mean, I always was funny, but I, I, I didn't know... I thought what I was doing was cool,

  5. 7:16 – 9:08

    Were You Always the Funny One?

    1. BK

      and when from the outside looking in, it wasn't. It was funny. So I didn't realize that I was being funny. I, I think a lot of comics have this. Like, uh, I told, just told this story in therapy the other day. When I was in first grade, I played second base. I'm really into baseball. I was really into baseball growing up. Played second base. Fly ball to me, bases loaded, fly ball to me. I catch it, and then I spike it, and I take my shirt off, and I start dancing. Now, my dad was livid. He was like, "What is wrong with you?" And, but everyone laughed, and I thought what I was doing was cool and that people would be like, "Yeah." But they just see this six-year-old, seven-year-old dancing shirtless in second base. And so my whole life I think I was always trying to be serious. Like I, I dressed up as Kiss for the talent show. I was dead serious, like, you're gonna watch me, like, kill it out here. And I remember being in the thing. I had a guitar. Gu- guitar didn't have strings. I was gonna air guitar, and the kid looks at me, and he goes... The kid next to me had a violin. And I- he goes, "You play the guitar?" And I said, "No."

    2. JS

      [laughs]

    3. BK

      He goes, "What are you gonna do?" I said, "Just rock out."

    4. JS

      [laughs]

    5. BK

      And he's like, "You're just gonna go up there and dance?" And I was like... And then when he said it, I was like, "This sounds silly. Yeah." And then I just went out and just air guitared and danced in my mom's tights, no shirt, her belts around my chest, white face paint that me and Brian Callahan put on. So yeah, I think... And I, and I think I was that way all the way through high school. I don't think I was very funny in high school, although I was... I learned how to tell a story in high school. It wasn't until I gave up sports in college that people started saying I was funny.

    6. JS

      What made you learn how to tell a story in high school?

    7. BK

      Going to an all-boys Catholic high school. It was the best. It was the best, man. I'm saying the best. Your currency was could you hold a table? Wasn't chicks, wasn't did you look good. Could you hold a table? And so for lunch, the, you'd have a table, your boys,

  6. 9:08 – 14:35

    How Bert Mastered the Art of Storytelling

    1. BK

      12, and I would practice my story coming from religion to the table. I'd be like, all right, so we did a beer run, right? And I'm driving. Cayman comes in. He dives in. A dog grabs his leg. I take off. That's... And I'm practicing the story, and then I get there, and they'd be like, "Hey, uh, tell us about the fight." And I'd be like, "Okay, gotta 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, and they were like, "Oh."

    2. JS

      [laughs]

    3. BK

      Like, it was just... It was like storytelling was our thing.

    4. JS

      Yeah.

    5. BK

      And, uh, 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.

    6. JS

      Yeah.

    7. BK

      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?"

    8. JS

      [laughs]

    9. BK

      Like, just wild stories.

    10. JS

      Yeah.

    11. BK

      And then when I got to Florida State, uh, that's when I started realizing I was funny.

    12. JS

      I went to an all-boys 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. [laughs]

    13. BK

      Oh, Jesus.

    14. JS

      And when you'd figure out that Felicity wasn't real-

    15. BK

      Yeah

    16. JS

      ... because that was an American girl's name off a TV show and not a girl's name in England-

    17. BK

      Oh

    18. JS

      ... like, you'd never... There's no one I've ever met in England called Felicity.

    19. BK

      No, never met her.

    20. JS

      And then one of our guys was dating a girl called Felicity. [laughs]

    21. BK

      [laughs]

    22. JS

      We're like, "He's been watching too much American Pie." Like, that's like-

    23. BK

      Dude

    24. JS

      ... the feeling we'd get.

    25. BK

      Girls were a perfect example. I was so painfully serious about losing my virginity. I mean, I was dialed in. It was al- my only focus, and then when I did, it was such a tragedy-

    26. JS

      [laughs]

    27. BK

      ... 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 mean, I've told it on pl- it may not, this may not be the right setting for it, but I'll just say it was fast, and I did it wrong.

    28. JS

      [laughs]

    29. BK

      And I mean, ev- 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, they're, it was Ty Rodriguez, like, "Tell it again." And I mean, everything was like a tragedy, like a comedy of tragedies for me.

    30. JS

      And you've never reconnected back with this person?

  7. 14:35 – 17:56

    Growing Up with a Tough-Love Dad

    1. JS

      real.

    2. BK

      Oh, very real. Uh, my dad, my dad's a great dad. I love my dad. But he just was like, "Hey, you don't cry." I was 11 years old, I was playing catcher, and I got hit in the mouth with a baseball bat, and I lost, like, 26 teeth. And my dad came over, and he's like, "Okay, don't worry..." It was my birthday, by the way. And I was like... He's like, "Don't worry, you're okay. Mom's gonna take you to the dentist. I need you to go to shortstop." I was like, "What?" He goes, "You're not dying, and if I sub you out of the game, we forfeit the game. So finish out the inning at shortstop." And I remember being like, "What? I've been injured." And he goes, "Yeah, go finish shortstop." And they hit a ground ball to me at shortstop, I caught it, threw it to first. My dad goes, "I'm really proud of you. Go to the dentist." But my dad just, he just didn't, it was not... He didn't hit us, you know, but, like, he just was like... I remember his, when I got into comedy, he told me really clearly, "Buddy, eat shit, cash checks. That's how the world works. Eat shit, cash checks." His dad was in World War II. He stormed, like, Omaha Beach or, or, or Normandy. And, uh, his dad never talked about the war. Sat in the garage, watched Mets games, listened to Met games, and drank beer. And so my... And my, my dad lost his dad at 13. So I think my dad was just doing the best he could. But yeah, he told me... I mean, I mean, it, I remember, I remember it like an older... I remember getting anxiety attacks. [laughs] This is how flat my dad was. One day, I'm laying in bed, it's, like, after, after David Letterman, and I'm laying in bed. I had to be 10 years old, and all of a sudden I have this very crisp realization that death is real. And I went, "Hold on." I go, "One day, you're gonna tell me my dad's gonna die?" And I went, "Oh my God," and I started having a real panic attack. And I went into his room, and I woke him up. My dad doesn't wake easily. He's like, if you wake my dad, he's like, "What the f-" you know? And so I, it scared me. I woke him up, and I was like, "Dad, are you gonna die?" And he goes, "What?" I said, "Are you gonna die?" And he goes, "Yeah, you are too. Go back to bed."

    3. JS

      [laughs]

    4. BK

      And I, and then I went, "Wait, I'm gonna die? I didn't think I gonna... I, you, I knew you would die, but not me." And that was my dad. I, I, I, I, my, I had kids with panic disorder, and I was so not my dad with them. I was so like, "Yo, I got you. You're gonna be fine." Like... But yeah, my dad just, he was just trying to do the best he could. Uh, o- o- stuck in a house that he couldn't really afford, to making ends meet. He's got three kids. Didn't expect a third one. He's a lawyer. I don't think he ever wanted to be a lawyer. I mean, I'd say that. I don't know what he'd say, but I wouldn't say he, like, loves his job. But it's his job, and he does it. But that was his, "Do not cry. Do not cry." And if, and when I got older, and we got into a something, and he saw me, like, well up, he'd be like, "Oh, you better not cry." And I'd be like, "I'm gonna cry." [laughs]

    5. JS

      [laughs]

    6. BK

      It might, might explain why I cry so much as an adult now. [laughs]

    7. JS

      [laughs] So you just hold it back.

    8. BK

      I tried my whole life. And then I remember s- the first time seeing him cry. It was when I graduated Florida State, and they didn't let me graduate. Two teachers failed me because I was written up in Rolling Stone magazine, and they were, they thought I embarrassed the school. So they failed me, and I had to drive up to Tallahassee. And they told me, the administration said, "Just go talk to the teachers." And

  8. 17:56 – 20:40

    What It’s Like Seeing Your Parent Cry for the First Time

    1. BK

      I went to drive up to Tallahassee, and my dad walked me out to the car. It was like 6:00 in the morning, and I was getting in the car to drive to Tallahassee, and he started crying. And I'd never seen him cry. And I was like, "What is this?" And he was just... [gasps] And he's like, "It's f- when someone with your kid," you know. And like, I was like, I was, I got, I drove in silence, no music, just in the dark. He says-What did I just witness? [laughs]

    2. JS

      Did you ever talk to him about that?

    3. BK

      No.

    4. JS

      Still, till this day?

    5. BK

      No. My dad's an interesting guy. He's, he's changed a lot the older he's gotten. He's way more sensitive than he was when I was a kid. Joey Diaz gave him marijuana one time on accident, and he gave him, like, a handful of marijuana popcorn. It's the first time my dad had ever had marijuana. Easter morning, kids are searching for eggs. My dad eats a handful of popcorn. I go, "Buddy, that's weed." And he goes, "What? It's popcorn." I go, "No, Dad, there's weed in the popcorn." He goes, "How do they put weed in the popcorn?" I go, "Dad, it's called an edible-

    6. JS

      [laughs]

    7. BK

      ... and you just ate a lot of it." And so he goes, "Well, what do I do?" And I s- I grabbed a handful, and I said, "I'll go with you. We're gonna both eat weed." And we both ate weed. We did a podcast that day. And, uh, and then everyone leaves, and it's me and my dad, high as crap, drinking whiskey at, like, 5:00 in the afternoon, smoking a cigar, really high. And I leaned over to him. I go, "Why don't you like me?" Ooh, I'm gonna get emotional. And he just goes... [clears throat] He's like, "I love you. You just make me uncomfortable." [laughs] He was like, "I, I love you, and I'm afraid you're gonna die. And so I, I don't know what that does, but I'm afraid you're gonna die." I go, "I'm not gonna die." And he goes, "You don't know that." He goes, "I lost my dad when I was young, and I'm, I'm terrified to lose you. And I don't understand you. I don't understand your lifestyle." And I said, "Well, how can we fix this?" And he goes, "I wanna get you a cardiologist." And I said, "Okay." And he goes, "You'd do that?" I go, "I want you to feel more comfortable with me." And he was like, "I can get you a cardiologist. I can do all the tests. I can pick all the tests they do." And I said, "Yeah." And he goes, "Okay." And he had a cardiologist Monday morning for me, Dr. Kadan. And, uh, they did the CT scan. They did the stress test. They did all the tests my dad wanted, and everything came back clean. And my dad's like, "Now, you'll go to him every six months?" And I said, "Yeah." And our re- I wanna say, from that day on, our relationship has gotten so much smoother. I mean, I've forgiven him for stuff that he's did, and we're just a lot, a lot closer now.

    8. JS

      Mm. It's incredible, isn't it? Like, our parents trying to hold us back from seeing their pain, but actually seeing their pain is the only thing that kind of penetrates and make you go, "Oh, wait, they're a human, too."

    9. BK

      Oh. I found out my dad was human when I was 21 years old. And, and I remember finding that out, and I didn't understand it. My parents split up, and

  9. 20:40 – 23:36

    Realizing Your Parents Are Human Too

    1. BK

      I was so mad at my dad. I didn't, I didn't even want to talk to him. I did... I just, I was wanting nothing to do with him. And my Uncle Jerry called me, and he goes, uh, "When was the last time you talked to your dad?" And I said, "It's been a while." And he goes, "Well, that shit's over." He goes, "You call him today. He's your dad." "No, no, no, Jerry, I'm, I'm mad at him." And he goes, "Yeah, you just found out your dad's a human, okay? Your dad's a human. He's a regular man. He's not some superhero. So you call him. And look, you don't have to say I l- I love you. Just call him, see how he's doing, and just touch base." I did, and, and, and, and that, that was a period, you know, that was a growing period at that. But, uh, yeah, he's a, he's a pretty, he's a pretty great dude. I'll just say this, you know, a lot of people will be at his funeral. That's, like, the testament-

    2. JS

      Wow

    3. BK

      ... for, like, a great man.

    4. JS

      Yeah. That's a big deal.

    5. BK

      Yeah.

    6. JS

      That's a-

    7. BK

      Oh, it's, it'll be... Yeah.

    8. JS

      Yeah. He obviously means so much to you.

    9. BK

      Oh, yeah. I think everyone's dad does, don't they? I mean, for all our differences, and we have a ton, um, a l- a ton. We're... If you met me and met him, you would not know we were related. He's pretty quiet, does not want to get on stage, and sincerely doesn't want you to get on stage. I mean, he just saw me do stand-up for the first time-

    10. JS

      No

    11. BK

      ... at the Amalie. Yeah.

    12. JS

      No. After all these years?

    13. BK

      After all these years, I did the Amalie, which is the arena in Tampa. And I said, "Yo, if you're gonna, you should come and see me here. I, 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 was, like, our hero playing baseball growing up. I said, "Yeah, I know. I put him in your box." And he goes, "No, buddy, he's here. Do you think he knows you?" And I said, "Dad, he's at my show." He goes, "Mike... 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-

    14. JS

      Mm

    15. BK

      ... played at, at, at, at, 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 Bert's come? He's doing the Amalie," and I- he goes, "I was at his first show at Potbelly's." And Derrick Brooks leaves. [laughs] My dad goes, "Buddy, Derrick Brooks knows who you are."

    16. JS

      [laughs]

    17. BK

      I was like, "Yeah, I know, Dad. We just spent time with him. He knows who you are, too, now."

    18. JS

      [laughs]

    19. BK

      But yeah, my dad just, he just, that was the first time he told me to, saw me do stand-up.

    20. JS

      What did he say?

    21. BK

      I gotta be honest with you. I think it makes him uncomfortable. Like, I think he kind of half looks and half-

    22. JS

      [laughs]

    23. BK

      Like, I, I don't think he, I don't think he laughs a lot at it.

    24. JS

      [laughs]

    25. BK

      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

  10. 23:36 – 24:35

    When Your Dad Realizes He Can Use Your Fame

    1. BK

      say, borderline racist, but Shaq and I talked. It made us laugh.

    2. JS

      [laughs]

    3. BK

      And Shaq's like, "You gotta put that in the special." And my dad's like, "That does not go in the special."

    4. JS

      [laughs]

    5. BK

      And I was like, "Dad, Shaq says it's okay." And he goes, "I don't give a shit. I, I am not comfortable with that joke." So I took it out.

    6. JS

      [laughs]

    7. BK

      Shaq's like, "You took it out because of your dad?"

    8. JS

      Yeah. What?

    9. BK

      But I got a better Shaq joke now.

    10. JS

      Okay.

    11. BK

      Oh, yeah.

    12. JS

      What's the better Shaq joke?

    13. BK

      Well, I-

    14. JS

      [laughs]

    15. BK

      I, I can't do it. Is, I don't think your audience wants to hear it. [laughs] Go see me on the Per- the Permission to Party World Tour-

    16. JS

      There we go

    17. BK

      ... starting in September.

    18. JS

      There we go. That's, that's-

    19. BK

      It's pretty aggressive.

    20. JS

      Oh, oh, that's fun. That's fun.

    21. BK

      Yeah.

    22. JS

      People can look forward to seeing that. But what I, you know, what I'm hearing about your relationship with your dad, I think it's so interesting where we just talked about that unlock ofYou figure out your parents are human, and you also get context of their humanity. Like you were saying, his dad died when he was 13 years old, and he saw that, and then he was scared of losing you. Like, I remember my dad took me to his... the home he

  11. 24:35 – 29:05

    What It’s Like to Share Your Success with Your Parents

    1. JS

      grew up in in India, and his home was the size of this room. His home. So the kitchen's in a corner. There's... By the way, there's five kids that grew up in this house.

    2. BK

      Yeah.

    3. JS

      There's a bed over here. We get there outside, there's bats, cockroaches, and rats everywhere, because he grew up in, like, this slum-like area. Disgusting. I'm nine years old when I first go.

    4. BK

      Whoa.

    5. JS

      And then they shared a toilet with, like, 20, 30 families. And I remember going there at nine years old, and my whole perspective of my dad completely changed.

    6. BK

      Yeah.

    7. JS

      Because all of a sudden, I had, like, a reference point. Now, my life wasn't luxury in London by any means, but it wasn't that.

    8. BK

      Yeah.

    9. JS

      And when you see, like, bats and rats [laughs] and cockroaches at nine years old, which, like, freak you out-

    10. BK

      That's crazy

    11. JS

      ... and you think that's how your dad just walked to the toilet, walked back to his house. He was the youngest of five kids. And all of a sudden, you just get, like, a completely different perspective on the man you're looking at, and it sounds like you had that moment as well. And, and I guess my question is, it sounds like it's not something you had to reconcile through a conversation. Like, it's not like you've sat there and therapized it out or, or fixed it, but there's a s- there's a resolution that's almost happened between both of you where he can come and watch you on stage-

    12. BK

      Yeah

    13. JS

      ... even when he d- he hasn't for all these years. Like, would you say there's been healing? You said there's forgiveness from your side.

    14. BK

      Yeah.

    15. JS

      Like, what does that look like when there isn't a conversation? Because I think today we've got so much about you've got to have the conversation.

    16. BK

      Yeah. No. You know, I think for my dad, a lot of it was he always had the answer. You know, my dad's the kind of guy that when I was a kid, the Iraq War started, and I came home, and I was like, I was against war because I knew that's what hip- hippies were about, and I wanted to be a hippie, and so I thought that's what the right answer, I'm against war. And, uh, my dad's like, "No, you're, you're an idiot. Why don't you go to your room until you realize what an idiot you are? And then when you come down, I'll explain to you why you're an idiot." So I went to my room, and I was like, "I don't know why I'm an idiot. Like, I... What did I... I... And everyone should be against war." My da- I came downstairs. I go, "I don't know why I'm an idiot." And he goes, "Okay. There's a lot of interesting things about this war. Number one, it's the first televised war we've ever seen. We're watching them go to war, and it starts like a football game, and me and you have the opportunity to watch this. Number two, this man, Saddam Hussein, is a monster to his own people, and we are going in to get rid of him. You do not know any of the politics, so shut your mouth and sit down and watch the war." And my dad was like that with everything. If you ever said an idea, if I... To this day, if I say, um, if I say something, anything po- political, my dad takes the opposite side and will tell me. So in a weird way, it never gave me a foot to stand on politically. That's why I don't talk about politics on stage, because whatever I would say, my dad would tell me I was, I was wrong. He wanted to show me... I think he was protecting me from looking foolish or protecting me from being the guy at a party that was a know-it-all. And, you know, my dad kind of flew under the radar always. And I think when I started getting successful, there was a part of my dad where he no longer had an answer for me. He no longer had the solution. He couldn't, he couldn't put me in the right direction. When they fly, because they're older, I send them through a, a special entrance at the airport. It's a little expensive, but it's easier for them, and my dad had a broken hip and got knee problems. My mom's [laughs] my mom's a piece of work. My mom's like me, okay?

    17. JS

      [laughs]

    18. BK

      And so, uh... And he gets really upset. He's like, "Buddy, I don't need this. I can't... You can't afford this." And I go, "I definitely can afford it." And he's like, "No, you don't know." So one day I had to send him, like, my bank statement and be like, "I can afford to put you through there." And he was like, "What the f- You..." Uh, like, he just... I, I think in that, it's not like the, you know, the younger lion taking over the bigger lion, but, like, like me n- like me not letting him pay for meals, that makes him uncomfortable. Like, that's who he's been. He's been the leader of our family, and I'm not saying he's not still our leader. He is. By every stretch of the means, he is. However, I think not having all the answers for me and not being able to tell me exactly what to do and be confident in his decision made him very uncomfortable.

    19. JS

      Mm.

    20. BK

      I think. I don't know.

    21. JS

      But you never... It didn't seem like you were searching for his approval at any point.

    22. BK

      Uh, uh, I was... Oh, my God, that's all I've been doing.

    23. JS

      Mm.

    24. BK

      My whole life. My whole life. He didn't like my long hair, got a flat top. Came into his office, and he was like, "You look like an idiot." And I was like, "God dang it." Like, all I've ever wanted is that man's approval. That's it. That's it. Uh, entirely,

  12. 29:05 – 35:08

    The Lifelong Quest for a Parent’s Approval

    1. BK

      without a doubt, I just... Like, when he says, and he says very often how proud he is of me, uh, it doesn't, it doesn't miss me. I- it hits me in the chest, and it makes me feel great, and the fact that he'll call up, and he'll be like, "Buddy, we went to the Macaroni Grill. You know, I, I say my n- I say my last name, and they go, 'Are you related to Bert Kreischer?' They knew who you were. Buddy, I got a table right away. They gave me... They... You know they do the bacon there, you know, the big bacon?" My dad's like that. He l- uh, he loves it, and I, he... And I think he kind of loves my whatever celebrity I have because it trickles to him. And now, like, when he goes to, like, when he goes to... Like, he went to my special. Him and my mom sat backstage. They didn't go in the... They sat on chairs on side stage, and he's deaf. And, like, not deaf, but he's losing his hearing. So I'm doing the show, and I hear him say, "What did he say?"

    2. JS

      [laughs]

    3. BK

      I'm like, "Jesus, Dad." "She said... He said he saw her suck his dick."

    4. JS

      [laughs]

    5. BK

      "What?" "She lost weight, Albert. She... He saw her give her a bl- Leanne gave him a blowjob." And I'm like, "Will you two shut up?"

    6. JS

      [laughs]

    7. BK

      But yeah, they, uh...

    8. JS

      [laughs]

    9. BK

      Yeah, I'm, I'm s- I'm constantly seeking his approval. I, I think it probably could be said for my career. I think the reason I'm into comedy is I'm searching for approval. I want people to like me. I d- I do. I want people to have a good time, and I want people to go, "You were fun." I don't need to be the best comic, but I want the people that see me-To really have had a great time and like me

    10. JS

      When was the first time you felt like you got his approval?

    11. BK

      Uh, Will Smith. Yeah, Will Smith. Will, I got a deal at, like, 26 years old. I'd been doing stand-up. On my 26th birthday, I was in New York, and I was just partying. I wasn't doing stand-up. I'd been there for a couple months, and I'd gotten hammered the night before, and it was my birthday, and my phone rang at, like, 8:00 o'clock in the morning, 9:00 o'clock in the morning, and I saw it was my dad, caller ID, and I said, "You know what? 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-

    12. JS

      [laughs]

    13. BK

      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 noth..." 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, and I'm telling you..." And I s- I said to him, I go, [laughs] "It's my birthday." And he goes, "I know what [censored] 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 w- I wanna, I wanna... I don't want you to feel this way about me." And he goes, "No, you should not wanna 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's Bert Kreischer. I would like to be a stand-up. I'll clean up. I'll mop up. I'll br- I'll flip burgers. I'll stand out. I'll do whatever you need, but I need an opportunity.'" And I said... I remember saying to him [laughs] I go, "I, I can't do it today, tonight, 'cause I have a party planned." He was silent, and he just goes, "You have a, 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, 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, first time young Black kid in Harlem, that's how it works for him. Do you know why? 'Cause he has humility, and he knows how to get what he wants. That's how it works for him. Doesn't work for you 'cause 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 Bleecker, 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 Lewis Shafer, and I told him exactly what my dad said. "My name's Bert. I wanna do this. Any advice, anything you can do to get me on stage?" And Lewis Shafer said, "You should move back to Tampa." And I went, "What?" And he goes, "You're not gonna 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." I called him the next morning. He goes, "How did it go?" I said, "Not good. This is exactly what he said." And he goes, "Perfect. This is what I want you to do. You go back tonight, and you say the same sentence as if he'd, uh, never said it to you."

    14. JS

      [laughs]

    15. BK

      And I said, "Okay." So I s- I said, "Well, what do I do if he says the same thing?" And he goes, "You're gonna do that every single night until there's a point where you're gonna break him, and he's gonna go, 'Fine, I'll give you a job.'" So I went back that night, and I went, "Hey, Lewis, my name's Bert Kreischer. I, I wanna be a stand-up comedian. I'm from Florida." He goes, "Yeah, didn't I tell you to move back to Florida?" I go, "Listen, here's the deal. My dad called me a piece of shit yesterday. I feel like a piece of shit. I need an opportunity." [laughs] I go, "I'm gonna be doing this every night for the next year as long as you keep saying this." And he went, "Fine."

    16. JS

      [laughs]

    17. BK

      "If you can bring in 20 people, I'll put you on at the end of the night."

    18. JS

      Nice.

    19. BK

      And I was like, "For real?" And he goes, "Yeah. You can go on after, right before Godfrey." And I was like, "Okay." And man, I brought in 25 people. Someone got heckled. Karen Bergreen got heckled by four Puerto Rican guys I brought in because one was going to jail the next day.

    20. JS

      [laughs]

    21. BK

      And I was like... I shit, I... And Lewis Shafer comes out, and he's like, "Where's the comic?" And I was like, "No one's here." And he's like, "You're on. Let's go." Put me on stage, and frat boy Bert came out, and I lit these four Puerto Rican guys up so hard and n- 'cause I knew that guy was going to jail, and I di- I mean, I was like, "Hey, man, have fun tomorrow. Don't drop the soap. The place is going nuts." And I was like, I was like, "Can I give you advice about jail?" [laughs] I was like, "Suck it before you..." And then, I mean, they-

    22. JS

      [laughs]

    23. BK

      It was so great. They walked out of the room. The place went nuts, and I was like, "And I got a job." Lewis Shafer's like, "You can do this every night." Six months later, Will Smith discovered me. Will Smith discovered me, and my dad was floored. He was floored. We watched The Fresh Prince on Monday night every Monday night.

    24. JS

      Yeah.

    25. BK

      It was a, a six-figure development deal, and I remember that was the first time my dad didn't have an answer. And I said, uh, I said, "What do I do with this money?" He goes, "I, I don't know. I've never gotten

  13. 35:08 – 37:20

    How a 6-Figure Deal with Will Smith Changed Everything

    1. BK

      a paycheck like that." He goes, "Buddy, I, I..." I remember him stuttering like, "I, I can't tell you. I don't know." And he goes, "Let me hook you up with Bob Gazarian," I still remember the guy's name, "over at Merrill Lynch, and we'll, we'll figure it out." And that was when my dad was like, he's like, "You, you met Will Smith."

    2. JS

      [laughs]

    3. BK

      Will Smith taught me how to pitch movies and pitch TV shows, and he was like a blessing in my life.

    4. JS

      Yeah. That's beautiful. I didn't realize we had Will in common either.

    5. BK

      Will's the b-

    6. JS

      Yeah.

    7. BK

      I mean, look, I love Will.

    8. JS

      Yeah, yeah. One of my favorite people.

    9. BK

      He's, he's one of my-

    10. JS

      He's like family to me, yeah

    11. BK

      ... he is, he is the sweetest guy in the world. He was so good to me. He gave me great advice. We were about to pitch ABC Jamie Tarses, God rest her soul, and I, I drove over from the Valley with him and J- J- JL and, uh-

    12. JS

      Yeah, yeah, JL, yeah

    13. BK

      ... and, uh-

    14. JS

      James Lassiter, yeah

    15. BK

      ... yeah, J- and I-

    16. JS

      Yeah

    17. BK

      ... and I had to piss, and Will came in, and he goes, "I'll go to the bathroom with you." So he sat at the stall right next to me at ABC. And all... A- any guy knows that the sound of a man's urine hitting a, a, a toilet sometimes indicates how big their, their, their dick is.

    18. JS

      [laughs]

    19. BK

      And he had a fire hose. I mean, it was like, "Hawww." And I got s- I couldn't pee. [laughs] I swear I got, I got gun-shy. And Will says to me, "Can I tell you everything you need to know about Hollywood?" But I'm so in my head, going, "Pee, pee, pee." I didn't hear a word. I didn't hear one word. And then he goes... And then he stops peeing. I realize if I can't pee next to Will Smith, I can't sell a show next to Will Smith. I start peeing, and all I hear him say is, "Be yourself." That's it.

    20. JS

      [laughs]

    21. BK

      That's the only thing I heard. And then I went into the room, and, uh-Will was like, "Bert used to party hard," or something. I was like, "Yeah, you guys ever try to knock yourself out?" And they're like, "Huh?" And we used to do that in college.

    22. JS

      Yeah.

    23. BK

      And you had to do it on the side of a b- like, put your head against something, 'cause if you just hit your head-

    24. JS

      [laughs]

    25. BK

      ... it's not gonna happen. And I knocked myself out [laughs] and Will's just like... And we sold a sitcom that day.

    26. JS

      [laughs] I love that man.

    27. BK

      Yeah, he's the best.

    28. JS

      Yeah, he is the best. Dude, it's like, as I'm listening to you, I'm just like, there's... It's so interesting because I feel like that moment that you told me about baseball with, you know, you and your dad, and your dad telling you like, "On your birthday, just go play and then we'll sort it out later," what was the power of that? Like, what was the

  14. 37:20 – 42:50

    The Moment You Know You Have to Chase Your Talent

    1. JS

      good thing about that and then what was the hard thing about that? Like, there was good obviously that came from it, this work ethic-

    2. BK

      Yeah

    3. JS

      ... this ability to turn up, the ability to push through pain. But there must've been some pain that stayed which searched for that approval. But what was the good and the bad? Because it sounds like you've been able to process both.

    4. BK

      You know, he had a mentality, eat shit and cash checks. And when I was at Travel Channel at the very tail end, I was just hoping to get renewed, and I knew they were changing presidents and I, I had lasted, like, three or four presidents, but every time you, you went to a new president, you were j- And, and, and it was money, and I needed money, I had a family. I was ignoring stand-up, I was ignoring the podcast. All the stuff I do now, I was ignoring all of it. And I was at the beach with my dad, we were having a cigar and a glass of wine. And he goes, "So what's the deal? What, what's our plan?" I was, I think I was 42 years old, 43 years old, looking for my dad's approval, and this is so my dad. I go, "You know, buddy, eat shit, cash checks," thinking he'd go, "That's my guy." And my dad started crying. He goes, "Oh, I think I [censored] you up." He goes, "Eat shit, cash checks means, is for guys like me with no talent. Guys like you need to, you need to sh- go after your talent."

    5. JS

      Wow.

    6. BK

      And he was, he was crying. And you know, Rogan had just said that to me too. He had just had that conversation with me. And my dad's like, "If you don't go for it now, you're gonna regret it." He's like, "Do it." 'Cause I had this, uh, uh, longstanding offer from Showtime, Gary Garfinkel, God rest his soul, to do a special, and I kept pushing it to do Travel Channel stuff. And he goes, "Buddy, you, you should do it. You should... Hey, follow your dreams." So I, I did the Showtime special. No one watched it because I took my shirt off.

    7. JS

      [laughs]

    8. BK

      It was like, I remember, I remember them saying, "Yo, if you take your shirt off, you're giving them a reason to change the channel." But what's fascinating is the thing that gets them to change the channel back in the day where you were Caesar, and you'd be like, "No, no," is the exact opposite for the internet. You see a guy with no shirt on on the internet, you're like, "What's this?" And you click it. And I posted The Machine story and it went viral.

    9. JS

      Yeah, yeah.

    10. BK

      And, and it was, I remember my... But my dad gave me this, like, insane thing of even if you're sick, you show up. Even if you're, even if you're hurt, you show up. I, I think it's my punitive way that I work out, is that I'm, if I'm hungover, I work out extra hard. I was hungover. I flew, all, drank all day yesterday in New York, flew here last night. This morning I got up at 8:00, got in the sauna for 30 minutes, got in the gym. We did abs. Who the [censored] wants to do abs? Uh, ran, lifted weights, and sweated out, but that's my dad's mentality, is like, you get up, you do your work, you, no matter what. And that was the lesson, I, I mean, I, I... And my takeaway from being 11 and getting hurt, my dad going, "You finish inning, you don't let anyone down. You don't, you get, you finish the game." You know, I, I had a showcase for ICM one time. This is just my dad's mentality. And there was a guy that went, opened it, and then the next guy went on, was a guy named Earthquake. Do you know Earthquake?

    11. JS

      No.

    12. BK

      Unfollowable. Black dude who destroys. Destroys. His name's Earthquake. I mean, just... And he, he's Earthquake 'cause he leaves you, the room in an earthquake. And I watched all my friends, I won't say their names, but all my, all my white friend comedians panic. No one wanted to follow Earthquake. And they just came to me, they're like, "You wanna go up after Earthquake?" And I just, my dad would be like, "Yeah, that's your job."

    13. JS

      [laughs]

    14. BK

      "Do your job." And I went up after Earthquake, and he had a joke, his last joke was about his name, Earthquake. I forget the joke. But I knew my first joke was about my name, Bert. So the joke was, uh-

    15. JS

      [laughs]

    16. BK

      ... was, uh, "My name's Bert, I know what you're thinking, hot, sexy name. Do you do porn? No."

    17. JS

      [laughs]

    18. BK

      I said, "Bert's the last name you want to hear during sex. Just some chick on top of you in the dark going, 'Uh, uh, uh, Bert.'"

    19. JS

      [laughs]

    20. BK

      And then I go, "Shh, call me Earthquake."

    21. JS

      [laughs]

    22. BK

      And the place exploded. But you know, here's the thing, and this is my dad's, my dad's br- mentality, is if you don't get on stage, if you don't show up to work, all the stuff that could possibly make your life great just disappears.

    23. JS

      Mm.

    24. BK

      And that's been my mentality this whole career, is you show up, no matter what, you show up. You got an audition, you show up. You get, they want to meet you in a general meeting, you still don't think it's right for you, you show up. And I, that's definitely the way I've taken the road. Dude, let's do the road. Make sun, make s- hay while the sun shines. Get out there and grind.

    25. JS

      Yeah. Yeah. And that's what it takes. I mean, I feel like comedy's like, there's a new comedian every month that's taking off.

    26. BK

      Yeah.

    27. JS

      You've had, like, a longstanding career. It's hard to do that, to keep reinventing yourself, keep coming back, special after special, success after success. It's hard to do that.

    28. BK

      Yeah. I-

    29. JS

      And it feels like it came from that.

    30. BK

      I, I, 100%.

  15. 42:50 – 44:09

    Embracing the Power of Pressure

    1. BK

      told me, "You love pressure. Buddy, it, 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 on first and second, we're down by two runs, that's when I performed. When we faced the fastest pitcher we ever faced, that's the guy I hit the best off of. And I, and I'll tell you is in stand-up 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. Uh, 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."

    2. JS

      [laughs]

    3. BK

      "This is when he's gonna perform the best."

    4. JS

      [laughs]

    5. BK

      "Sit back, everybody." And man, that show, I mean, best stand-up show I've ever had in my entire career-

    6. JS

      Wow

    7. BK

      ... was that one show.

    8. JS

      Wow.

    9. BK

      It was... That was murderous.

    10. JS

      Wow. People say with comedians, obviously, there's such a defense mechanism with humor and comedy to mask pain and challenges and all that kind of stuff. I wonder... And you've said before as well, like, "I usually, you know, laugh through pain." It's like what- what's a pain that you couldn't laugh through?

  16. 44:09 – 47:06

    Is There a Pain You Can’t Laugh Through?

    1. BK

      I hesitate to even say this, but I've been very lucky.

    2. JS

      Mm.

    3. BK

      I've been very lucky. I haven't had a lot of tragedy in my life, and I can laugh at just about anything. I, I, I laughed at my grandmother's funeral. I laughed twice at my grandmother's funeral. [laughs]

    4. JS

      Tell us. [laughs]

    5. BK

      My... Was... Um, I'm, I started crying. My dad had a rule, like, don't cry in front of your kids, and I started crying, and this is before we put Priscilla down. I started crying. He goes, "Whoa, whoa, whoa, whoa. Hey, stand up." It's him and my Uncle Jerry. And my dad goes, "Buddy, pull it together." I was like, "I'm upset." And he goes, "Why?" I go, "'Cause your mom is in a box up there." And he's like, "Yeah, she had a great life. You celebrate her life, you don't cry. Can't let your girls see you cry, then they're gonna be freaked out." I was like, "Dad, it's just, it's just hard looking at her." And he goes, "No, no, no, no. You're fine." I go, "Well, she w- they have her... She's not smiling." And he goes, "Are you a [censored] idiot?" He goes, "Do you want her smiling in that box? Do you have any idea how creepy that is?"

    6. JS

      [laughs]

    7. BK

      And I started laughing. And then he goes, "There you go. All right, you're out of it. Good. Let's go."

    8. JS

      [laughs]

    9. BK

      So then at the end of that funeral, everyone leaves. My dad and my Uncle Jerry, ugh, I mean, this makes... They go, "Hey, come on." I said, "What?" And they go, "Let's go, let's go say goodbye to Grandma." And this was them saying it's okay to cry. Oh my God, I've never seen two uglier cries in my life. This, these men let go of years of trauma. The... I'll tell you, I'll tell you, right before she died, this is the hardest I've ever watched these two men laugh. We go to the hospital. My grandmother's in congestive heart failure or whatever. So we go to the hospital. Grandma's in the bed. Uncle Jerry and my dad are in the corner, and they're hiding the, their faces 'cause they're crying.

    10. JS

      [laughs]

    11. BK

      They're hiding their faces behind the curtains.

    12. JS

      [laughs]

    13. BK

      Okay? And they're really emotional. And I, and I'm not. For whatever reason, I'm not in that moment. And I go, "Hey, Grandma, how are you doing?" And she goes, "Ugh, my back hurts." That's, that's heart failure is when your back hurts. And I go, "Well, do you want me to rub your back?" And she goes, "I would love that, birdie boy. Rub, rub my back." So I start rubbing her back. I go, "I love you so much, Grandma." I go, "I think you're gonna make it out of this." And then I go, "Wait, I think you might have dropped a tissue behind your bed, 'cause I can feel... I think there's tissue falling off." And she goes, "That's my skin." And my dad and my uncle go from crying to laughing hysterically.

    14. JS

      [laughs]

    15. BK

      And my dad's going, he's kicking my uncle and going, "He's rubbing skin off her back. He's rubbing skin off her back."

    16. JS

      [laughs]

    17. BK

      And my Uncle Jerry's just, he's... [laughs] And I'm watching these two curtains shake, and I'm just rubbing skin off her back going, "I love you, Grandma."

    18. JS

      [laughs]

    19. BK

      Yeah.

    20. JS

      [laughs]

    21. BK

      I laugh through, I can laugh through just about anything.

    22. JS

      Oh, God. Oh, God. That's... When, when was the first time you let your daughters see you cry?

    23. BK

      I c- I start... Okay, uh, I, I, I came home. I was on the treadmill. Leannon's in the room with the girls. And this is, this is in Priscilla's third knee surgery. Priscilla had

  17. 47:06 – 49:56

    Letting Your Kids See You Cry

    1. BK

      five knee surgeries. On her second knee surgery, they realized the other knee was bad, too. They were gonna have to do another one, and the guy goes, "Listen, you're, you're 15 grand into this dog. I, I think it's just... I think we need to put her down." And I went, "What?" And he goes, "I can't promise that these are gonna last, but, like, I'm telling you, the one that we already fixed, that's bad again. We gotta do that again. So she's asleep. I can put her down right now if you'd like." And I went, "Well, hold on." And I went, "Oh my God, give me a, uh, can you give me a second?" And he goes, "Yeah, yeah. Give me... Like, go talk to your wife, but call me soon." So I start crying, and I, and I'm, I'm trying to hold it together, and I walk in the room and the girls see me crying, and they start laughing. And they go, "Oh, Mom, Dad's crying." And Leanne goes, "Girls, if Dad's crying, we're all about to be crying in a matter of seconds." [laughs]

    2. JS

      [laughs]

    3. BK

      She's like, "This isn't funny." And I go, "They want to put Priscilla down." And George and I are like, "What?" And then pulled it together, and we didn't put her down. We got two more... We got those two knee surgeries, then two more knee surgeries. And, uh, yeah. But they've seen me cry a lot now.

    4. JS

      Yeah.

    5. BK

      Once I, once the floodgates open... Dude, I cried at the Avengers movie when, when Spider-Man died.

    6. JS

      [laughs]

    7. BK

      When Spider... I was sobbing crying, and Isla's mocking me. I cry at movies real quick.

    8. JS

      I do, too. Yeah.

    9. BK

      And they will... And they just... You just watch them. They don't even watch the movie. They just watch me and stare at me and giggle.

    10. JS

      Yeah.

    11. BK

      Yeah.

    12. JS

      Well, that's why I find you to be such a interesting, fascinating person, 'cause, like, you've got this larger than life personality. You've got this partier background. And then, like, you've got, like, this soft heart. [laughs]

    13. BK

      Oh, I'm, like, the biggest-

    14. JS

      Like, and it's... Yeah, yeah. And it's like... And even when I met you, I could just tell immediately. I was like, "You know, this guy's got the softest heart," and at the same time, if I saw you, I wouldn't necessarily have that, you know, perception.

    15. BK

      Yeah. Yeah, I think that's accurate. I don't think anyone... I think people think I'm a one thing, and then when they find out, like-The one that always shocks everyone is I've only had sex with six women, and they're like, "What?" And I was like, "Yeah, I'm just... I wasn't that guy." Like, I- the time I lost my virginity, that changed my life. In that moment, I went from, "Okay, I'm not cool guy that can just bang chicks. I'm super sensitive guy that needs you to get me, 'cause I'm not sure I'd do this right." [laughs] Like, my wife goes, my, my wife takes those phone calls, and she knows I'm never gonna cheat. She knows I am a wreck. I am a wreck. But yeah, and so everyone's like, "Really? You've only had sex with six?" I go, "Yeah," 'cause I, in college I'd go to a bar and I'm just hoping someone would get me. Like, I wanted someone that wanted to watch Fletch three times in a night.

    16. JS

      [laughs] How did, how does she get about, obviously, all of the exposure of her life and her sex life as well? What's, like, allowed? What, what do you need permission for? What do you get away with without any-

    17. BK

      She says as long as it's funny.

    18. JS

      Oh, wow. That's fair.

    19. BK

      She goes, "As long as it's not mean and it's funny, I'm in." I remember the time I realized she was game for anything. She farted during oral sex.

  18. 49:56 – 51:43

    Why the Way You Tell a Joke Matters

    1. JS

      [laughs]

    2. BK

      And I s- and I s- made a joke, and she started crying. And I said, "What are you crying about? I'm the one in the fire hole. What are you... What..."

    3. JS

      [laughs]

    4. BK

      "I'm gonna shit in my mouth. What are you... You're crying?" And she said to me, "You're definitely telling this on stage."

    5. JS

      [laughs]

    6. BK

      And I, "Wait." I said, "What? Can I?" And she goes, "Well, yeah, obviously if I did this, someone else has done this. I'm not the only one that ever did it."

    7. JS

      [laughs]

    8. BK

      "And it's funny. You should talk about this on stage." And I did, and man, it was, it was, like, a killer bit for a while.

    9. JS

      [laughs]

    10. BK

      But, like, yeah, she, she watched this hour, and her note was, "I'm cool with everything you're saying. I need to know the way you're saying it has love in it."

    11. JS

      Mm.

    12. BK

      Like, it has to have a smile in it.

    13. JS

      Mm.

    14. BK

      Because I, I was do- when you do material a lot, you get bored of it, and sometimes you don't show the sparkle in it the way you did when you wrote it. And with this material, I mean, making fun of a, a woman because she's getting older and she's going through menopause and she's aging, and if you don't say it with love or a smile, that was her exact word, there needs to be a smile and a little bit of rascal in your voice. Like, you need to say... And so she was really adamant about that.

    15. JS

      I love that. She's like a comedy coach.

    16. BK

      Oh, she's... I mean, look, she's not funny. Let's be very clear.

    17. JS

      [laughs]

    18. BK

      I take offense when she tells the people at the party, "I'm the funny one at home." I go, "D- d- hang on. My comedy bought the house. Let's be real, okay?"

    19. JS

      [laughs]

    20. BK

      She's a g- she's a gangster. She's awesome. And same with our girls. She's, kind of monitors the material and, and runs, runs it by with them, with her, and, uh, talks to them about it and, you know, yeah.

    21. JS

      Do they think Dad's really cool or Dad's human?

    22. BK

      Oh, human.

    23. JS

      [laughs]

    24. BK

      They don't think I'm cool at all. They do not.

    25. JS

      When did that, when did it go from cool to human? Or was it ever cool in the first place? [laughs]

    26. BK

      I don't think it was ever cool. I don't think it's... No, it's, it's, you know, there... I had a period of, of where Georgia, I could tell, thought I was kind of cool.

    27. JS

      Yeah.

    28. BK

      Like, Georgia had this,

  19. 51:43 – 54:05

    How Your Kids Really See You

    1. BK

      like... We, we took her on Fully Loaded one year, her and her friend Daisy. I got this great picture. At the end of the night, I'd, I, we'd, I'm, I'd tell The Machine, and then I'd bring all the comics on stage, and I'd have them bring me a beer, and I'd kill a beer, and I'd spit it in the air, and it would, it was a fun moment, way to close the show, and it was always a really cool picture. And one year, I call all the comics out, and then everyone starts walking off, and I'm saying goodbye, and Georgia comes out. I got this great picture. And she throws her arm in the air like she just did a stand- like she's, [laughs] like she did the stand-up. And I was like, "What are you doing?" She goes, "I just wanted to see what it felt like."

    2. JS

      [laughs]

    3. BK

      But, like, uh, I think they think I'm okay. I don't think they think I'm cool. Like, I- i- in all honesty, if I didn't ever go to their college ever again, they'd be very comfortable with that.

    4. JS

      [laughs] Well, why do you turn up to their college? You don't need to drop them there.

    5. BK

      Like, like, no, like, parents' weekend.

    6. JS

      Yeah, right, right.

    7. BK

      Parents' weekend or... You know, we went and looked at colleges. I wanted Georgia to go to Boulder, and, uh, so we went to Boulder, and this kid yells out the window, "The Machine!" And then all of a sudden, word got out on campus, and kids started running and finding me, and I watched this kid, my child, lose interest in a school very quick. A great school, one of the best schools in the universe. I love that school. And she was like, "Yeah, I'm not going here." And I was like, "What?" She goes, "I'm not going to a place where you have fans." I was like, "Well, baby, I think that's gonna be tough."

    8. JS

      [laughs]

    9. BK

      And then she was like, "I won't go to Florida State. I won't go to Florida. I'm not going here. I'm not going to Georgia. I'm going, I'm gonna find my place." And so I didn't go look at schools with her. And the next two sc- schools she looked at, she loved. She got into both of them, and she chose one.

    10. JS

      Wow.

    11. BK

      And same with Isla. Isla would... I, they hate when I get recognized. Last night, we pl- we flew in, and paparazzi was waiting for me at the airport, and Georgia was just like...

    12. JS

      [laughs]

    13. BK

      Like, she walked in and, like, stood by a wall and was like, she was like, "Can we just, Mom, can we make this stop?" And I was like, I, I don't, I'm not rude, so I'm like, "I'm gonna talk to them. If they wanna talk to me, I'll say something to them. I'm not gonna be there forever." But yeah, they, I, I think they would be cool if I wasn't famous.

    14. JS

      How do you deal with that? Like, with, when you're raising kids, you've been doing this for a long time. They've probably been exposed to it since they were kids. Like, how, h- how have you had that conversation with them? Because obviously it's still not easy for them.

    15. BK

      We had a moment, uh, we were, we were skiing. It was a very

  20. 54:05 – 56:51

    The Challenge of Uninterrupted Family Time

    1. BK

      luxurious thing to do. It's not lost on my kids, 'cause we didn't always have money, but we were going skiing, and Georgia was having a rough time. Just, there was something going on with Georgia. By the way, we didn't know this, but we all had COVID at the time. [laughs] And so, so Georgia's having a rough time, and she's, has a meltdown, and she's, you know, you know, what, a junior in college, high school at the time. She's having a meltdown, and I'm talking to her in front of where we're staying, right by the lifts, and we're both in our ski outfits. I'm holding my snowboard. She's got her snowboard, and she's crying, and I'm trying to talk to her and help her out with this thing she's going through, and these two dudes are like, "Oh, shit, The Machine." And I just look in her eyes, and she's like... And I was like, "What's up, guys?" And they're like, "Can we get a picture?" I go, "I'm kind of doing a thing." They're like, "Real quick, real quick." And I'm like, "It's easier just to take the picture than to..." And so I take the picture. She goes, "I understand that this allows us to do this." She goes, "It would be nice just to have my dad sometimes."And, and I was like, "I know." And it, it's sharing your, your s- time with, with fans is what di- is difficult for them.

    2. JS

      Mm.

    3. BK

      And I'm not a good guy at, like, saying no.

    4. JS

      Mm-hmm.

    5. BK

      Like, I j- I don't... I've, I've seen f- my friends do that before, and it always rubs me wrong.

    6. JS

      Mm.

    7. BK

      Where I'm like, "Just take a picture with... It doesn't-"

    8. JS

      Yeah.

    9. BK

      You know?

    10. JS

      Yeah, I feel the same way. Yeah. It's like a... It's almost like this is the reason why you get to do what you love every day, and-

    11. BK

      Yeah

    12. JS

      ... the least you can do is-

    13. BK

      Least you can do is take a second-

    14. JS

      Yeah

    15. BK

      ... and listen to someone.

    16. JS

      Yeah. And I'm assuming with you as well, people have great stories. Like, that's how I feel. Like, I get to talk to people who just have amazing stories to share and life-changing moments, and I'm like, I feel like if I didn't sit there and listen to that, it, it almost gives me fuel-

    17. BK

      Yeah

    18. JS

      ... to keep going and, you know, keep moving because, yeah, I hear amazing things, and I'm sure you do, too.

    19. BK

      Oh, I mean, you know, you forget, you know, a little bit of what we do is talk. We talk... You know, there's someone right now that probably has a weird relationship with their dad, and is l- hearing this-

    20. JS

      Yeah

    21. BK

      ... and is going... You know, there's things that, uh, we hope is funny, too, but, you know, like, doing, uh, the biggest one I always got was, "You got me through the pandemic."

    22. JS

      Mm.

    23. BK

      You g- 'Cause, you know, we put out content for them to distract themselves with. A lot of people didn't have big houses to stay in during the pandemic. They were in an apartment, and they're just like, "This is miserable."

    24. JS

      Mm.

    25. BK

      And, uh, I get that a lot. I get... You know, the, right now the one I'm getting is, you know, you know, "We just put our dog down."

    26. JS

      Mm.

    27. BK

      "You... I've never d- I've never laughed and sobbed at the same time. Thank you for letting us process." And, but, you know, at the least I can-

    28. JS

      Is that from the new special, Lucky?

    29. BK

      ... the least I can do is take a second and talk to someone who wants to say hi to me.

    30. JS

      Yeah. Yeah. And it's like, I mean, that, that's something that you do quite uniquely, I feel, like, the ability to make someone laugh and cry. Even, like, as we've been talking today, I'm like, [laughs] I'm like having, like, a really emotional moment with you.

  21. 56:51 – 1:01:33

    Just Show Up and Do the Work

    1. JS

      real beauty in that. Like, have you ever sat and thought about, like, was this the first time in this special that you got extra emotional and got people to-

    2. BK

      Well-

    3. JS

      ... crying? Was this, like, one of the first times, or?

    4. BK

      Yeah. I've never done this before. I mean, I m- I'm... I don't, I don't mean this, like, cocky, but I don't think, I don't think there's a lot of comics-

    5. JS

      That's what I'm saying, yeah

    6. BK

      ... that are, that are doing that.

    7. JS

      Yeah.

    8. BK

      And I, and I'm not, and I didn't know if I should do it. Like, it-

    9. JS

      What made you do it? Like, why did you go there?

    10. BK

      It was ready. I, I did that story before Razzle Dazzle. I was gonna do it at the end of Razzle Dazzle, and I just thought, "Ah, I don't know." It just, it felt weird to me for that material. That material, it felt weird. And I, and I, and then, and I was... And Georgia called me one time on stage. I was on stage, and right before I re- re- released Razzle Dazzle, and she goes, "What are you doing?" I said, "I'm doing stand-up." She goes, "Oh, are you telling the escape room story?" And I was like, "No. Why? Should I?" She goes, "Absolutely, Dad. You remember you almost shit in Papa's mouth?" And I went, "Oh, yeah." And then she kinda broke down the story on stage, told it. I went, "That's my closer." And I was like, "Good. I'll get made fun of if I do this dog story. Everyone's gonna make fun of me and, and, and say I, I, I just... I can... I'm, I'm thinking of it too much." And then I do this special, and, uh, everyone I was working with was like, "Are you seeing what's happening in the room?" And I was like, "No," 'cause you can't really see anything, and it's an arena.

    11. JS

      Yeah. [laughs]

    12. BK

      And they're like, "Yo, we're out there," and they're like, "Grown men are sobbing crying. Like, fam- people are holding each other and laughing and crying at the same time." They're like, "This is different." Like, I remember a dude I really respect, I brought with me on the road. He's like, "That has to be your closer." He's like, "That..." He goes, "I don't know one comic making people cry, but making them happy cry. Like, they're crying for something they love, and then they're laughing, and you end on a laugh." He's like, "You have to do it." I j- I just didn't know if it would work. And it's like what you said about writing a book. You sit with it for four years.

    13. JS

      [laughs]

    14. BK

      And then... And I shot this in July, and it just came out this March.

    15. JS

      March. Yeah.

    16. BK

      So I've been sitting on this special, and I just was like, "I am gonna get destroyed." Like, I, I just started in my head going like, "No one's gonna like this. Everyone's gonna make fun of this last story. They're gonna go, 'Oh, Bert always cries. That's all he does.'" And, um, and I put it out, like, the first day. It was trending at number two, and I went... Which I'd never trended over six. And I was like, "Ooh, that's weird." And I went into my stories where people, like, mention you, and it just looked like a straight line. And I was like, "Whoa." And I was like, "I only got one story? I only got one person mentioning me." And I hit it, and I hit it, and I was like, "Oh, my God." I couldn't get it, the line to go away. And I was like... And it was all about this story. Everyone was just cr- sobbing crying. S- people were sending me pictures of their dogs. They were holding their dogs. They were filming their husbands crying. They were-

    17. JS

      [laughs]

    18. BK

      I mean, it was so cathartic for me. And I'm, I'll be very real. So y- y- uh, you get on Netflix on, on a Tuesday. You find out if you trend on Wednesday. I did press all Wednesday morning from 6:00 in the morning till 9:00. Uh, I don't know if anyone's liked the special. I don't know if it's trending. I don't know any of that. I go and take a nap, and I'm waiting for an agent or someone to text me. Like, I figured, I said to myself, "If it just trends in the top 10, I'm gonna be happy." Look, I'm 52. Maybe, there's guys doing it better than me, younger than me. I expect them to just blow my doors off. Just please tell me I have another year of doing stand-up. That's the way, the way your head's thinking. And I took a nap. I woke up, and I got a text from a younger comic I really, really like, uh, Ricky Velez. And he just said, "Yo, man, you're killing it. This is a great special. I've been a fan of yours for a while. I'd love to hang out next time I'm in LA." Not do a podcast, hang out. I was like, "Oh, that's cool." I, and I like this guy. This guy's doing what I was trying to do at his age. He's doing it way better than I'm doing it. So I was like, "Oh, nice." I was like, "He liked the special. Cool." I was like, "Nice, a young kid liked the special." And then my texts blow up, and that's when I went into my stories, and I saw it. And as I'm watching the stories people are saying, I started sobbing crying just out of gratitude, out of just sitting there going like, "Ugh, the thing I did's good. It's not horrible." [laughs]

    19. JS

      [laughs]

    20. BK

      "It's not horrible. People don't hate me. Ugh." I was just sobbing crying in my bed, and I was like... And then Leanne comes in from her workout class. She's like, "What's wrong with you?" She just walks in, she goes, "You're trending at number two."

    21. JS

      [laughs]

    22. BK

      And I was like, "What? I didn't even look at Netflix." And then I was like, and so I was like, "Whatever. I'm good. My first day was good." And then it's been like that every day. The response has been crazy. People really are connecting with that last story.

    23. JS

      Yeah. Yeah.

    24. BK

      Yeah.

    25. JS

      Talk, talk to me about what you just said now, that, that inevitableEmbracing of insignificance and irrelevance that everyone goes through. Like, that idea that one day-

    26. BK

      Oh, yeah

    27. JS

      ... no one's gonna care about me, no one's gonna care about you, no one's gonna care about 99.9%

  22. 1:01:33 – 1:07:24

    Success Was Never a Straight Line

    1. JS

      of everyone who's relevant, current, whatever trending we wanna call it, and there's that thing that creatives go to where you see them holding onto their last bit of relevance and significance, and it's painful to watch.

    2. BK

      Yeah.

    3. JS

      But you understand it because you go, "Well, wait a minute, I really liked..." No matter how much we say, like, you know, Ellen, Ellen said something that I love. She goes, "I used to always say I didn't care what people thought. That's when everyone thought I was amazing." [laughs] Like, you know? It's like-

    4. BK

      Yeah, yeah

    5. JS

      ... it's really easy to say, "I don't care what anyone thinks," when I'm the number one person in the world, but then when you actually are not number one, number two, number three, number four, you, you start getting down on that list, you're beyond number 10, now you do start caring what people think, especially, like, what you said, the new god. Like, and especially when the new god has respect, that's a beautiful thing.

    6. BK

      Yeah.

    7. JS

      But when the new god's kind of like m- you know, living how you were when you were the new god-

    8. BK

      Yeah

    9. JS

      ... who has that overconfidence, that arrogance, how do you think about that? Like, how have you reflected? Have you thought about that at all?

    10. BK

      I thought... Oh, that's all I think. You gotta remember, I didn't- I wa- like, I did- I was just gonna be a journeyman comic. Like, I, I wasn't supposed to be successful. I, I, I... You know, I did Travel Channel, and I thought that was gonna be my life, and then when I got let go from Travel Channel, and my special didn't do well, Ne- or The Machine didn't do well, and I'm getting fat-shamed by Tommy, I was like, "Okay." I, I remember saying, "Are we cool with this? Can we do this like this at this level?" Like, I was the guy at the store when people would talk to me, more successful comics would talk to me, they'd look over my shoulder waiting for someone better to talk to. I was a nice guy, people liked me, but I wasn't relevant to them, and so they were like, "Ooh, that guy's... Oh, that guy's 28 and he's killing it. Uh, give me one second, Bert, I'm gonna go talk to him." And I was like, "Am I cool with that?" I remember one time coming offstage not wearing cool sneakers, wearing dad jeans, and seeing a young comic murdering it in the car that my wife and, and I had seen in... We had looked at that brand car, and th- he had the car they had in the showroom. I- the car was, like, $220,000, and I was like, "Oh, how did he, how can he afford that?" So I wasn't supposed to be successful, and I was cool with it. I was definitely cool with it. I was like, "I can just do comedy at Funny Bones. I love comedy. I'll keep putting out specials. Maybe. You never know. Look, Rogan's a good friend. I can always do his podcast." You know, that's how my brain worked. I had my podcast, but no one cared, and then I had the conversation with my dad. I got let go from Travel Channel. I had the conversation with Rogan, and him and Tommy, I remember them both saying, like, "Don't worry, we can help you get ad sales." And I was like, "Okay." And then I posted The Machine story, and then all of a sudden it went like crazy. I mean, I'd never experienced that before, like, genuinely viral. And, uh, and then all of a sudden I started selling tickets, and I was like, "Whoa. Holy crap, this is crazy," just selling out, not looking at ticket counts, just going in and knowing everything's clean. And so I, I, I really honestly had kind of already let go of all of it, but there's a part of me that remembers, oh, it was cool when they... I remember g- I remember getting... Right before I got let go in To- uh, Travel Channel, I got into a town car. They got me a town car for something, and I remember getting in and going, "This is the last town car I'll ride in." I was like, "I should really enjoy this."

    11. JS

      Mm.

    12. BK

      So I kept always saying that. Every time I went to theaters, I was like, "I probably won't do theaters again." You only do theaters once really. I'll go back to clubs, but enjoy this. This is the Chicago Theatre. Let's go for a jog tonight and watch the sunset. And then, yo, uh, this is crazy. I'm doing The Beacon. I probably am not gonna sell two shows at The Beacon ever again. So let's really enjoy this, and I brought my girls that I grew up with in Tampa up to the- out to my bus, and we hung out, and, and I... And then when I started doing arena, I didn't even know I was gonna do arenas. I didn't know I was doing an arena. I was in, m- m- uh, Green Bay, and I was like, "I'm doing an arena?" And they're like, "Yeah." And I was like, "Whoa, I gotta really enjoy this." And so I-

    13. JS

      I love that

    14. BK

      ... every step of the way have been like, "I gotta enjoy this." But then, you know, I take nine months off, s- wait for the special to be released, and I was- I m- and I, and I did, did it again. Am I cool with not being relevant? Am I cool with not being the thing, the shiny object, and maybe going back to clubs or going back to theaters? I'd... I, I remember I texted my manager today. I go, "Hey, guys, I'm, I don't need to do arenas anymore. I can do... I, I love theaters." I saw Kevin Hart did a theater. I go, "There's no shame in doing a theater." [laughs]

    15. JS

      [laughs]

    16. BK

      A lot of them, you could see a lot of them make more money than an arena.

    17. JS

      [laughs]

    18. BK

      And then the special came out, and I was like... I j- it was just like a relief. I was like-

    19. JS

      Wow.

    20. BK

      "I was like, I can breathe. I can breathe." That, oh, my God, that is like... And, uh, and then we were on a call today, and they're like, "Yo, you know, doing arenas again in the fa- the fall, starting September." And I told them, I said, I... and I said to them, I said, "You know, hey, when we book out 2026, I don't have to do arena tours. Like, I don't have to be holding onto something. I'm cool with doing some clubs and doing some, some theaters and, and, and, and doing some outdoor venues. I'd like to do the Gorge again." But like I go, "Let's shake it up," you know? And they were all like, "Really?" I was like, "Yeah."

    21. JS

      [laughs]

    22. BK

      I don't know. I don't care. Like, it's... But that, it's... I've watched it go away for people. It sucks. And you're right. Watching someone hold too tightly. That's why that song Hold On Loosely by 38 Special is so great.

    23. JS

      Mm. Yeah.

    24. BK

      "Hold on loosely-

    25. JS

      [laughs]

    26. BK

      "... and don't let go."

    27. JS

      [laughs]

    28. BK

      "'Cause if you hold too tight, girl, you're gonna lose control. You're gonna, you're gonna..." That's a great song.

    29. JS

      It's a great song.

    30. BK

      Hold On Loosely.

  23. 1:07:24 – 1:11:12

    Don’t Let Greatness Become Familiar

    1. JS

      gate to even get to the house.

    2. BK

      Yeah.

    3. JS

      And I was just like... have to live in the moment that I cannot believe. And now we- I've been co- I've been working with him for seven years, so I've driven to this house, like, every day for years.

    4. BK

      Yeah.

    5. JS

      But I was like, it loses its value when I stop being grateful for it. As soon as it becomes familiar, like what you're saying, I love what you just said. I love, love, love what you just said. Because as soon as greatness becomes familiar and excellence becomes familiar and all of this stuff becomes familiar, you lose its value. And then when you lose it, you don't, you never got to experience it.

    6. BK

      Yeah.

    7. JS

      So you realize you never had it in the first place, 'cause you were just running after it. Like, you were chasing the whole time.

    8. BK

      Oh, yeah.

    9. JS

      You never held it.

    10. BK

      Oh.

    11. JS

      And what you just said is you held it for that moment.

    12. BK

      I still hold it.

    13. JS

      Yeah, you still hold it. Yeah.

    14. BK

      You know, I just signed up... When I did The Machine, uh, my, uh, my producer, Kale Boater, he's v- he's the one of the greatest guys. Like, guys. Happens to be a great movie producer. And I was like, "Yeah, I'm gonna, um, I'm gonna not drink, and not... I'm gonna be clean, I'm gonna work out, I'm gonna eat clean, I'm gonna look good." And he just kinda looked at me and he's like, "Yeah, hey, man. That's, that's not who I hired." He's like, "Look, if I know who you are, like, if you're not having fun, you're not gonna, it's gonna show up on screen. But if you're having fun, it'll show up on screen. Like, if you were having fun..." And he goes, "I can't tell you if the movie's gonna be a hit, I can't tell if it's gonna be a flop. You never know. But what I can tell you is, you're probably only gonna get to make one movie. So enjoy this process."

    15. JS

      [laughs]

    16. BK

      "Have fun." And man, I had so much fun making The Machine. It was the experience of a lifetime, 'cause every day I was like, "I will never make another movie. I will never have another movie where I don't have to memorize lines, 'cause I say whatever I wanna say." Like, I, it's just, it was like the greatest life experience of my life. But yeah, that's how I look at every project is, "This is probably the last one I'll do." You know? I thought, I, I, I know I have one more special with Netflix. Like, I owe them one. And I go, "That might be my last one."

    17. JS

      But that only makes it better though.

    18. BK

      See, the cool thing about a special, and, and you don't, you don't get to experience this, and, and I don't think some comics think about this, but I think about this. So I take this material that I create about, uh, 18, twen- 24 months out, and I take this and I work it and I play with it. And at a certain point, I get bored of it, and I reinvent it, and I come back to it, but I play with this. For two years I work on this same stuff. And when I do my last taping, I did six shows, and on my last taping, I was present and I said, "This is the last time I'll say these words."

    19. JS

      Mm.

    20. BK

      Oh, it's like, it's like my... I give them to the universe, that I'll never get them again. And I get so emotional saying that, but you know, you're so... Your material is who you are. And I c- and, and I go, "This is the last time I'll say this word, this wording and this cadence." And it's just so... It's, but with a band, you never do that.

    21. JS

      Yeah, yeah, yeah.

    22. BK

      And then sometimes you tell a story like The Machine and you've been telling it now for 15 years.

    23. JS

      [laughs]

    24. BK

      And I'll still tell it. I'll still tell it. [laughs] Listen, I was, that story changed my... I sat, listen, I sat in the Ryman Theater. There's a woman named Angela Johnson, brilliant comic. She's got a great nail salon bit. I was with Arj Bharata and Nate B- Nate Bargatze. None of us were working very well. None of us were making money. She had sold out the Ryman, and they were chanting for this nail salon bit. And I said to the Lord, I said, "Lord, give me one bit that people give a shit about. I'll tell it until the day I die." And He was definitely listening.

    25. JS

      [laughs]

    26. BK

      He was like, "I got you. I'll, I'll one-up it. I'll make it a 12-minute bit. You're gonna make a movie out of this bit. I'll te- I got you." And that's my nail salon bit.

    27. JS

      [laughs] You've, you've always been so open about mental health.

    28. BK

      Mm-hmm.

    29. JS

      And, like, talking about anxiety, and, and you know, that's a big priority for us here as well, because I find that so many people in their journey never get to share that. People don't get to see that within people. You've talked about anxiety, intrusive thoughts. Like, why were you comfortable enough

  24. 1:11:12 – 1:17:26

    Living with Anxiety When Life Doesn’t Slow Down

    1. JS

      to open up about that without thinking people are gonna pick at that, look at that weird, your peers, kind of... Where, where did that g- you get that cour- courage and confidence?

    2. BK

      [laughs] I think it was stupidity.

    3. JS

      [laughs]

    4. BK

      I think, I mean, I just was like... You know, when I got into the business, I was like 100% transparency. I was watching comics as a character, and I was like, "Ah, that doesn't seem fun." So you're gonna pick a character, and then you're gonna stay that character your whole life? I was like, "I'm gonna be Bert, and I'm just gonna be Bert, and anything I think, I say. And, and, and I'm gonna live by the sword, die by the sword. This is my thing." And when anxiety came up, I just was like, "Yo, it's, I have anxiety." Like, I have anx- I have really bad anxiety. I have OCD, I have intrusive thought. I have, I have struggle with that. I don't know, I don't think I have depression, only because I just, I can't, I can't, I can't s- I think people that have real, real depression, I think it's insulting for me to think the thing I go through is depression. I know what it's like to have anxiety. I had an anxiety attack driving in college, and I didn't know what it was. I thought I had a brain tumor. And then the first time I was explaining it to someone, and the, and I, this is, I mean, this is probably 27 years old, 28 years old. I was explaining it to someone, and they were like, "Oh, you get anxiety attacks." I went to a therapist and she said... I have a fear of flying. I, I don't know if you noticed, but I have a fear of flying. I have rituals I do when I fly. She said, "Well, you, yeah, you have anxiety. Uh, let me give you Xanax." Then I took Xanax, and I was like, "Oh my God. Is this what regular people feel like?" I was like, "Are you kidding me?" And then I, I developed a problem with Xanax, as, as many people with anxiety do. And my wife, when, right when we had Georgia, she said, "Yo, you're done taking Xanax." Like, I had taken, I'd been using it, you know, on and off for, like, a year. And she, maybe a little more. And Georg- and Leanne's like, "You're done with Xanax. It's, you can have one if you need one, but it can't be your go-to every night. It can't be the way you put yourself to sleep." And then when I s- we started doing podcasts, I just was like, I don't know. I was like, I just be open and honest.

    5. JS

      Mm.

    6. BK

      You know? I have ruminating thoughts where I just chew a thought over and over again.

    7. JS

      What's been the most recent panic attack you've had?

    8. BK

      Oh, I have... This morning. You want one, the one this morning? Uh, I h- I'm, uh, a great, great comic, uh, Nick Thune, was telling me about when he quit drinking. And he said he was having a liver failure, and his back was hurting. And this morning I woke up on my side, and my back hurt, and I went, "That does it. You've partied too much. Your liver's failing. Your liver's failing." And I started going through-... thoughts I could not stop. And I have a saying when I go, when I start having anx- anxiety or OCD, I go, "Be like a shark. Get out of bed and start moving." Second you start moving, things start helping. And I go get in the gym, get in the sauna. Let's get in the sauna. Let's get in the sauna, let's sweat some stuff out. It's just back pain. You're, trust me, you would have other symptoms. And I, but I can't connect with it. And I, and it just, it goes on and on and on. And then, and I just obsess about it. And then, and I bring it up to almost everyone. I've brought it up to everyone I've seen today, and then I go, "No booze. No booze anymore. I'm done for a month. I'm gonna cut off for a month. That does it." And then I come up here and I see your house, I go, "All right, bottle of champagne."

    9. JS

      [laughs]

    10. BK

      What's the, what's it gonna hurt, right? But, but, but I have a, I have a saying with, uh, life, whether you're dealing with anxiety, OCD, eating, uh, uh, drinking, masturba- whatever your little thing is, my saying is, and I, it kind of calms me down, "Let's do today just a little better than we did yesterday." That's all we gotta do, just a baby step. Little better than yesterday. And if we have a bad day today, realize tomorrow we're gonna have, we're gonna do better. We have an opportunity to do better tomorrow. And so I've been stuck in that mindset today, and I said, "Let's just get, let's do a little bit better today than we did yesterday." And so that's where my head's at. But yeah, they've got, I've, I've had really... And you know, my daughters have anxiety. Uh, and, and Leanne doesn't. They have sleep anxiety. They both had sleep anxiety when they were young. So Georgia would, uh, wake up and think she was dying. And I remember I was so glad I had anxiety then 'cause I could help her. Leanne's like, "Just go count sheep." I go, "Uh-uh, let's not count."

    11. JS

      [laughs]

    12. BK

      "Let's, we're not counting. That's the worst way to deal with this." Just [laughs] 'cause if you, it's shutting your brain off is the thing you need to do.

    13. JS

      Yeah.

    14. BK

      And if your brain's just going after it, you're, you're screwed.

    15. JS

      Yeah.

    16. BK

      And so, uh, but Leanne's also gangster. She got both of them into therapy immediately. Uh, and this therapist helped them immensely. But now, uh, Georgia and I can text about anxiety and talk about it and, and you know, it's, the best thing about it is when you know other people have it, is you're like, "Oh, so I'm not broken. I'm not crazy."

    17. JS

      Definitely not.

    18. BK

      Yeah, and that's the s- the greatest feeling. And it's cr- it's, you know, my, look, my family's seen me, when I get ready for a flight, it's like I ac- I get physically ill. I start feeling my head getting tight. I feel this. And they're like, "Hey, you're just having anxiety." And then to, to recognize it sometimes doesn't help 100%, but you can breathe. That's, uh, one other one thing I always say, like, "Wait, I'm breathing. I'm still breathing." And I just take deep breaths and [inhales] I'm still breathing. Crazy anxiety scuba diving.

    19. JS

      Oh, yeah. I mean, definitely. [laughs] Trying to breathe in scuba diving's hard enough.

    20. BK

      Sc- I mean, probably one of the biggest pan attack- panic attacks I ever had was scuba diving in a thunderstorm in Fiji at 90 feet.

    21. JS

      Yeah, that would do it. Yeah.

    22. BK

      And I'm, and we're in a tin boat, and I'm just like, I get in the water and we start sinking, and I realize very quick nothing I like is down at the bottom of this ocean. And I start kicking up to the top. And my dive instructor just grabs me, grabs my BC, grabs my thing, puts it in my mouth, like just holds it there, and just going like this. [inhales] [exhales] And I sunk with this Fijian woman who looked like Junior Seau, she was a big woman, and she s- took me to the bottom of the ocean. [laughs] And I was like... And then but, you know, I got through it. You get through it.

    23. JS

      Yeah.

    24. BK

      You always get through it. No one dies from anxiety.

    25. JS

      Yeah. You've developed enough coping mechanisms.

    26. BK

      I don't know if I have, and I don't know if they're healthy. I know alcohol's been a big coping mechanism of mine. Yeah, when I, the first time I learned I could sleep without drinking, like, you know, 'cause you do it from, like, 22 to, like, you know, 30, and then one day you're

  25. 1:17:26 – 1:19:29

    Building a Healthier Relationship with Alcohol

    1. BK

      like, "I gotta try to go to sleep without a cocktail or a glass of wine." First time I did that, I was like, "Whoa, I can fall asleep. Shut up." My, oh my God, I've got enough tools to shut my brain off.

    2. JS

      [laughs]

    3. BK

      Yeah.

    4. JS

      And that relationship feels healthier now with alcohol?

    5. BK

      Oh, yeah. I mean, look, let's be real, alcohol is poison. Everyone knows that. It's not good. You shouldn't do it. But I'm also not a Mormon. I like to have a good time. I like to get loose. It's, for alcohol, for me, it's not even the buzz. I, I gotta be honest with you. It's the letting loose. It's the celebration. It's the, "Hey, do you wanna do a shot?" And you go, "Oh, I definitely wanna do it." Like, like the, it's the permission to party, like it literally is. I mean, I named that tour this because when someone's like, "Hey, man." When someone lights a joint and you're like, "You want that?" That's, that's like, "Yo, let's do it. Let's get after it." I love when people crack open a bottle of wine, crack open a drink and go, "Hey, you, you want one?" I, it's, it's the funnest thing in the world. When, when flight attendants say to me, "Can I get you something to drink?" I love that, 'cause they don't always say that. But when they do, I go, "This is gonna be a good flight."

    6. JS

      [laughs]

    7. BK

      I al- I said I have a speech that, that I've s- I've, people p- passed around, but it, it is like a first kiss. When we got married, Leanne goes... I said, "Does it bum you out you'll never have sex with anyone?" She goes, "No, absolutely not." I said, "Me either." I said, "I think I'm good just having sex with you." She goes, "What really bums me out is I'll never get a first kiss." I, now, for us, that's the worst, 'cause we gotta do the kiss.

    8. JS

      Yeah.

    9. BK

      All the anxiety's on us. We gotta wait the whole night, does she wanna kiss me? Is she gonna kiss me? Should I take her? Should I do it in the car? Should I do it when we walk to the car? When should I do it? Oh, no, that was the wrong time. That was the wrong time.

    10. JS

      [laughs]

    11. BK

      For a, for a woman, it's just this excitement of like, when's it gonna happen?

    12. JS

      Yeah.

    13. BK

      Is he doing it now? When's it, is it, when's my present show up?

    14. JS

      [laughs]

    15. BK

      And that's how I feel about shots. [laughs]

    16. JS

      [laughs] Well, what's the Whoop telling you? I see you with a Whoop on.

    17. BK

      So I'm crazy, I'm crazy neurotic, okay?

    18. JS

      Okay.

    19. BK

      So I che- I check all of it. My favorite day in the year is, what, Oc- uh, December 30th when they post our scores.

    20. JS

      Yeah.

  26. 1:19:29 – 1:22:00

    How Tracking Your Fitness Can Change You

    1. BK

      I love Whoop. And uh, I've found that if I am overly hydrated, my, my heart rate is lower. So every night before I go to bed, I drinkFour liquid desks, 19-ounce liquid desks. I drink four of them. I pee in the middle of the night, but I drink four of them. My heart rate's around 56 beats per minute when I... And I... And that's after having, you know, a bottle of wine or some Por Osos. And, uh, so I'm wildly hydrated, and that is my key for my Whoop. It also, you know, for me, it also tells you how hard to work out. I love that. I love a goal because, you know, when we did the first Sober October, we were try- also trying to set goals of how hard we can work out, and that, when you see the top of the mountain, you know where you have to go. And so you go, "All right, I'm not done. I'm getting back on the treadmill. I'm gonna get on the assault bike. Okay, here, we're gonna do the SkiErg for... We'll do..." And I, like, I love that. Like, right now, I've already hit my goal. My goal was... Like, I slept horrible last night. My goal was, uh, I think a 10, and I'm at 9.6. But if it wasn't, go to the gym, hit the SkiErg. Uh, 10 calories, 10 times, and we'll see, we'll just get there. 10, and give it a minute break. Yeah, I like that shit.

    2. JS

      [laughs] I love it. I love Whoop too.

    3. BK

      I love that.

    4. JS

      It's great to measure. You need it.

    5. BK

      And then they measure your steps, and you're like, "Yo, Whoop, how long have you been doing that?"

    6. JS

      Yeah.

    7. BK

      "Because you, you... I didn't send this in. You just turned something on. Give me my old steps. I want to know what my old steps were."

    8. JS

      Yeah, yeah.

    9. BK

      Yeah, I, when I started measuring steps, was the very first, I got a Fitbit, the little one you put in your pocket.

    10. JS

      Yeah.

    11. BK

      And bro, that changed the game for me. I was like, "I'm into fitness tracking."

    12. JS

      [laughs]

    13. BK

      And then when they sent these to us for the first, second Sober October, [exhales] buddy, I've been... This thing does not come off my wrist. Unless I do a special, I take it off. You're gonna need to pay me for that Whoop.

    14. JS

      [laughs] Yeah, may- maybe we should figure that out.

    15. BK

      Yeah. They used to... They, they still do. They, they're pretty good to us.

    16. JS

      Yeah. I love that. But it has been... I mean, you are literally the best time.

    17. BK

      Buddy, you've-

    18. JS

      And, and, uh-

    19. BK

      ... you're the best interviewer I've ever done. You're so good at this. I feel so present. Um, it's crazy.

    20. JS

      You're... But you're so much fun.

    21. BK

      No.

    22. JS

      And you gotta realize this is like, there's good chemistry here.

    23. BK

      We... What we should do is we should do a double date, your wife and my wife.

    24. JS

      I'd love that.

    25. BK

      And then my wife's gonna go, "Shut the [censored] up, Bert. Let him talk." [laughs]

    26. JS

      [laughs] I can't wait to be a... No, honestly, we have to hang-

    27. BK

      Yeah

    28. JS

      ... outside of this. Like, I'd love that.

    29. BK

      I've got your number.

    30. JS

      You're, you're such a good time. And we end every episode with a Final Five. These, uh, questions have to be answered in one word to one sentence maximum.

  27. 1:22:00 – 1:36:59

    Bert on Final Five

    1. JS

      you've ever had or received?

    2. BK

      Uh, don't take anyone's advice.

    3. JS

      [laughs]

    4. BK

      It's the best advice. But sometimes everyone's advice is so built up with their bullshit. I remember posting a, a, a dance video, and everyone's like, "Why would you do that?"

    5. JS

      [laughs]

    6. BK

      Sold out my tour in seconds. I'm so glad I didn't listen to anybody.

    7. JS

      [laughs]

    8. BK

      Don't take-

    9. JS

      That's a good story

    10. BK

      ... don't, don't take anyone's advice.

    11. JS

      I love that. Uh, I fully agree. The amount of publishers that told me not to call my book Think Like a Monk, that was my first book, and they were like, "Don't call it that. No one wants to think like a monk."

    12. BK

      They're, they're telling-

    13. JS

      Yeah

    14. BK

      ... they're giving you advice based on their failures.

    15. JS

      Totally.

    16. BK

      The... And you're not them.

    17. JS

      Totally.

    18. BK

      And then-

    19. JS

      And data, which is, which is already in the past.

    20. BK

      Yeah.

    21. JS

      Right? It's not-

    22. BK

      Having said that, Joe Rogan gave me the best advice ever.

    23. JS

      [laughs]

    24. BK

      And he just sa- he just said to me, just, you know, a little high, a little drunk, in the back of the store. He's like, "You need a Netflix special." And I was like, "Yeah." He's like, "No, you need one." I was like, "Well, I don't know how to get that, Joe." And he goes, "Be undeniable." And he just walked away. I was like, "The fuck does that mean?" [laughs]

    25. JS

      [laughs]

    26. BK

      I wrote in my joke book, and I just tried to figure it out. And then when you are undeniable, you're like, "Oh."

    27. JS

      [laughs]

    28. BK

      That was great advice.

    29. JS

      I love that. Uh, question number two, what is the worst advice you've ever had or received?

    30. BK

      Worst advice I ever ha- got was, uh, "You should, you should start wearing a shirt."

Episode duration: 1:36:59

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