Dane Cook's Journey to Success: Taking Risks and Betting on Yourself

Welcome to the Casey Adams Show. Dane Cook.

Oh.

How you doing?

I'm doing great, thank you. I really appreciate this. No, come. Stop. This is. This is. Glad we're finally getting a chance to do this.

Absolutely.

Are we allowed to say we've been back channel giving.

We've been chatting for, like, almost two years. Yeah, back and forth on Instagram.

It's. It's been. I feel like the podcast was already done in the dm. We just need to act out. Let's just read off what we'd actually initially put down there.

Well, I appreciate you having us at your beautiful home today.

Oh, thank you.

It's so cool. Like, just before we got started, I told you, I was like, I feel so at peace here. And, you know, just to, like, jump into it, as I was coming over here, I was just thinking about just diving into your story and background. You were selling out Madison Square Garden when I was, I think, four years old. Like, 2004, 2005.

Yeah. I think I felt about four or five years old on some days.

I say that because, like, understanding your story and the level that you did it, being one of the first comedians to do, like, an arena tour like that to then, you know, grabbing the water out of the fridge and you're like, you know, I used to stock shelves, and I'm turning the labels. Like, how do you feel about your life today, considering your background? And just like, talk to me about your life today, 2023, and how you currently feel about who you are and how you spend your time.

Oh, wow. Yeah, it's. Well, how I feel today is. I feel curious about, you know, where can I take all the data and all the, you know, trials and tribulations. And, you know, to me, it's always like, okay, now I get to. Everything's like, chapters or eras, right? And then I go, like, okay, now coming into this phase of my life, what do I want to take from the. The. The scared years growing up, why was I scared? I'll quickly partition. It's like, grew up in an alcoholic household, grew up in a house that was kind of always a bit, like, skewed. Everything was a little bit on a tilt. Okay. I didn't know this growing up. I just kind of thought you, you know, you fight for your life, and you're always kind of holding on, like, what is the household gonna, you know, be today? And. Yeah, and so I grew up in a lot of fear. My mom was phobic. I had anxiety. I was an introvert. I just. You name Kind of like you throw a dart at, like, a, you know, a board filled with elements of issues, and you would hit something that I. I endured growing up. So looking at that and then wanting to be in a home someday, that was level, you know?

Yeah.

The. The goal. There was two goals. There was, how can I reach the upper echelon in a career? And I don't know.

That's.

That's a lot out of your hands. It's hard work. But then psyche, sting, preparation, luck, and politics and just a lot of, you know, hooey and bullshit and, you know, handshaking and. Yeah. But more importantly was like, can I create a foundation someday so that when I come home, I feel peaceful, you know, instead of more chaos? So, yeah. Yeah. We're sitting in a place that I think indicative of that.

The epitome of peaceful here.

Yeah.

Today, for sure.

Oh, cool. Yeah.

Your story, coming from Boston, like, how did comedy become a part of your life? And, like, where did this idea for wanting to be a comedian? Did you want to growing up, or how did comedy come into your life?

I did. I really did. I loved funny people. They were. They were part of that nice escape hatch.

Yeah.

Through that portal, through the tv of, like, okay, you know, if. If I'm laughing, if my family's laughing, there was a sense of that. That calmed things down. Right. You know what I mean? That was like. There was a sense of camaraderie as well, through laughter. So I was identifying, like, oh, man. You know, comedy that I'm seeing, like, on. On comedy on television. Comedy through, you know, films that we watched brought some. It brought some. It sometimes even brought, like, introspection because we would actually be able to talk about comedy or something we watched. And I. Dichotomy of my family conversation based on things that entertained us. Yeah. So I think I looked at that as like, man, if I could be. And then I'd be making them laugh. I'd stand up next to the tv and I'd pretend I was in the scene that was happening in the living room. Then I was in the next room going, like, you know, I hear you, dad. I'm not coming out there and, like, they're laughing at me and they're laughing at the show. And I think that it was the first indicator that, oh, I can. I can be a part of those things that hopefully help bring levity. Yeah. And I fell in love with it, man. Fell in love with making people laugh. And I. I really fell in love with comedians. Those people felt like such A rare breed, you know, seeing that on tv. So for a lot of reasons, I was like, I got to give this a shot.

Yeah. It's so special. Like, growing up, I. I have. I can't say I've been to a lot of live stand up. I have over the years. I'm 23. Right. I started traveling more so by myself for business when I was like 17 and been to a couple of New York. I saw you here in LA once and you just. I look at comedians like, they bring so much joy to the room, to the world. And, you know, being a comedian and making people laugh, but then coming from a world where, as you said, like, things are on a tilt.

Yeah.

Do you look at it like it was an outlet for you, considering, like your background. Yeah. How you viewed it or how did you view comedy and how it attracted you?

It was, it was, it was an outlet because I also felt like I, I was, I was very imaginative. You know, I would get action figures and stuff and I would create not only like a, you know, kind of like a landscape with all these, you know, the GI Joe guys and the Barbies, and I took everything I had toy wise, and I would bring my family and I'd say, all right, this is the city's name, this is the world, and this is what this faction is against this faction. And I'd be like, I hid some other action figures at the other side of the yard. They're living in another village. And I'd literally go out into the yard and be like, you can't see him. But I. I built a place in that tree. I had action figures all over the house, hiding in the attic. But there was an origin tale, there was a backstory. There were good guys that had bad intentions. There were, you know, bad actors that, you know, were gonna turn.

Yeah.

And I think that my mom helped me to curate and cultivate this idea of, like, you're a storyteller.

Yeah.

Really is like, you're a storyteller. That means you could, you could tell jokes. You can, you can. She would always reinforce me, like, you can be funny. You're gifted naturally to be funny. But I think that there's more storytelling inside of you. And she always pushed me to try to figure out how to entertain people in ways that maybe were a little bit beyond just tomfoolery and, you know, the antics and fucking craziness that stand up can sometimes, you know, offer.

Yeah. Do you think, like being a comedian, do you think it's something that you're Naturally gifted with. I know if I tried to go and stand up in front of him and be a comedian, I would have a hard time with it, and it's not easy.

Yeah.

I've heard you say this before. Like. Like when it comes to public speaking and controlling a room as you do, there's such an art to it and a craft, and you're one of the greats at it. Like, do you think you're more so born with it? Obviously, you're putting the reps. That's obviously one of the important aspects of it.

There are.

What makes a great comedian.

There are a lot of elements that. That need to be learned. You know, the, The. The. The. The confidence, joke structure, the business side, how do you get booked? There's so many things that you need to learn in addition, but at the core of it, I think just having that ability to see things in a new and interesting way to go. Oh, okay. I think that that's funny because. And. And I knew early on I was kind of seeing the world through a different angle.

Yeah.

As maybe somebody more analytic or something of that nature. So I do feel like I was born with the funny bone. Yeah. But I think I had to get out of my own way. And there was a. There was a lot, once I stepped into the. The comedy clubs that I didn't realize came with it. And a lot of the pressure and a lot of the anxiety and there was. There was getting away from it on stage in that moment because you didn't have time to think about what, you know, anything wary or, you know, you got to perform. But the 23 hours in the day leading up to getting to that show comes with its own set of circumstances.

Yeah, I'd love to hear that. You say, like, the anxieties when it comes to some of the early standup mics you. You did to then something like Madison Square Garden. How do you compare that? Like, mentally going into that. The preparation, like, how have you changed your act and your style and what has led to those changes over time?

Yeah. I mean, Casey, the reality is all those hell gigs and sad road shows where the manager left and didn't pay you and you drive home, you know, with no G and you're freaking out. Like, all the formative years. It's nice to say that now the formative years. Right. It was more like, you know, the dysfunctional for sure. You know, surviving. Right. Those. Those hardships, you know, the. The obstacles. And to finally take that to a place, like, even before Madison Square Garden, to be Able to play beautiful venues. Well, well known clubs that I created, you know, the Improvisation or the Laugh Factory, Comedy Store in New York. The Comedy cel were having me. I mean, that already felt like such a great accomplishment just to share the stage. I used to perform at a place next to the Comedy Cellar in New York City. It was called the Cafe Wa. It was a jazz club that would also do a little comedy. And the reason I wanted to play there was because I knew Pryor played in there. Richard Pryor played shows in there. And then he'd go over to the Cellar. So the collection of stages that you get to play before, possibly a Madison Square Garden or something. It all felt like. I don't even want to say small victories, because they all felt like big victories just doing it. But I think that when I. Not to jump ahead, but like, when I saw the. The arenas getting closer into view, then it was like, I need to prepare myself as a. As a person, as a man, as a business person.

Yeah.

For what? If I want that, it's gonna bring a lot with it. Am I ready for that? You know, so it was like introspection mode at that point.

I relate. I. I was telling you before the show, I've done like 400 interviews and.

Right.

Sometimes I'll talk to big new people, starting shows or podcasts, and they'll see the big name or let's say they're watching this interview. And it's. Every interview had to happen to put me in the position to course have you on the show or have whoever on the show. And it's the. The preparation and doing the reps. And you've done that hands down.

Yeah.

What did. What did your life look like when you were doing the, you know, open mics? You go up on stage. Did you have this grand vision? And how did you think about it back then? Right. We live in a world today where, like, my buddy Matt Rife, who I've met a couple of years ago, and now he's like, doing this crazy world tour right now.

Yeah.

Like his.

You know, our backstory, Matt and I.

No, please tell me no.

When he was 15, he saw me live in an arena his grandmother brought me. He wrote me and said, I want to be a comedian. I said, finish high school and then come out to the Laugh Factory. He flew out too early with his grandmother. I met him at the club. I said, go home, finish school, and then when you come back out here. So he comes back out when he was 15. 15 years old. So then I start Basically mentoring him. And then, man, up until the 2019 tell like it Is tour, I had him featuring for me and I was pointing at him every night, going, telling people, like, bet on him.

Yeah.

You know, bet on him. But I will tell. I will share one funny thing and you can bust his chops on this. I took him to Runyon Canyon, 2018. I said, you got to get into social media. And he goes, nah, man, I want to. Like, I'm not for a number. And he gave me all his reasoning at the end of that hike, I looked him, I said, you're going to go home today and you're gonna fucking start social media.

You're joking.

I said, you're gonna let people get to know you in that way. And he went, all right, man. And it was like, I'm so glad everything he's done, he did.

Yeah.

No credit taken. But to be able to see, like, hey, if you lean into that.

Yeah.

I think you're gonna be one of the people that, I mean, I'll say now it's like, I think next year he defines what stand up comedy is.

Wow.

You know, for the next generation.

That's very. That's both. That's incredible.

Oh, yeah. I believe he's. It's really. The sky's the limit with him.

Yeah, I couldn't agree more. I mean, going from that to then, tens of millions of followers that he has on social. It's so cool. And my buddies, I got to give a shout out to him. Michael grew and we were. This is probably 2018, when he was probably getting in the scene. I was in New York, go to dinner, Hunt and fish club in New York City. And it's me, Michael, Matt, just getting to know him, had dinner and we went to see him that night.

Yeah. Where was incredible. You remember?

I don't.

Somewhere in the Village.

I really wish I could say.

Yeah, I wonder. Okay.

It was very small. Like, very, very small.

Yeah, yeah, yeah.

He was incredible. And like, seeing that. And by no means, we, like, hang out a bunch. We've been connected over the years. But to see the scale of that with social media, short form content.

Well, he's doing something that. What I also think is I was fortunate enough to do is he's. He's meeting his moment with his fans. And I think that's so important. It's so unique because if you make it on a hit TV show or you make it 10 other ways and you're a comedian, things come and go, trends change, and it's harder I've seen other people that have gone that way and get famous from a show. It's harder to keep the identity of who you are in your standup, and the standup is your ability to, like, let people know. I'm growing, I'm changing. This is the next journal chapter. So I respect him and I love what he's doing because for the rest of his career, wherever he takes it, side items.

Yeah.

He'll always at the foundation have made it.

Yeah.

As the thing that he's the best at. And that's very, very gratifying. It'll be fun to watch him over the next.

You know, Must be so epic for you, dude.

I'm sitting here like the old bull on the hill going, like, I told you. I knew it, I knew it. So it's, you know, it's. And I was 28 when I broke through, when everything started to click for me. So it's. I'm seeing it. And I just, I told him, I said, I know that you're gonna be spinning for a while, but, like, in those moments, you need. You need the legal help, you need the voice of the person that isn't the new. I'm always in his corner.

That's incredible.

Yeah.

I'm so glad we brought him up. Yeah, yeah, he's awesome. And just like, you can cut this whole segment.

He's got enough press. Okay. You don't need more chit chat about this. Right? You understand. You're happy with that.

Do you mentor? When it comes to up and coming comedians, how do you think about as someone that is one of the greats, how do you think about up and coming comedians? Your role there?

Yeah, my whole philosophy is because I mentor a lot of people that are not even in stand up comedy. I've been, I've had the accessibility to me through social media, whether it's good or bad. Sometimes you open it up and you're like, oh, boy. Okay. Well, not sure if I'm ready for this today, but most people have a good heart. And the. When somebody reaches out and I can tell when somebody's really like, hey, I know your story, or I've watched you on that podcast and you and Casey talked about da da. Like, when I can identify, somebody's really searching for that, like, I'm lost. I'm spinning. Where I think that I'm beneficial is I'm a Boston kid who's very assertive and I don't bullshit. So first and foremost, you know, if you ask me a question, I'm gonna. I'll tell you, even if it risks us losing our. This moment of our friendship, I'm still gonna tell you my truth. It may not be your truth, but. So I always offer up absolute, no bullshit truth. But my goal is to never tell a person how to proceed in performance. For example. My goal is to help me to help you to keep your integrity intact. My goal is, if I wasn't even a fan of what your performance art is, I would never tell somebody how to perform or what to change or like, oh, try wearing this. Or I'll tell you what you should be looking for legally. I'll talk about intellectual property with you and how to protect it. I'll talk to you about, like, how to handle the, you know, the people that want to, you know, be on the pull out, you know, coattail or the groupies or that and say, I'll help with all of that stuff. And even if you were to say, what do you think I should change in my act? That's not for me to know, or, I don't know, like, what to tell you to be funny. I know that you need to figure it out, even in failure to, you know, level up. I hate. I shouldn't say hate. I'm trying to not use that word as much in my life. I resent people that come in and try to tell a young entrepreneurial person how to perform. And it happened a lot to me. You know, I had people pulling me aside in Boston saying, you know, you move around too much up there, you know, and what I learned later is that meant I'm intimidated following you. I don't want. I can't do what you do. So I'm trying to take that away from you. And so I always said if I ever got to that place, I want to offer up love advice, you know, tough love.

Yeah.

You know, there's some people in my life I don't talk to right now. I love them, but they didn't want to hear the, you know, you're asking me.

Yeah.

You know, I love that I'm gonna be straight up with you. And it's gonna hurt me to say it, but. But I think you're asking me because you want the answer. And even if you defy it right now, and I've done this, and I'm thankful to say I've had people come back sometimes years later when they're ready to go, like, hey, thank you for, you know, being straight up with me. And I've done it. I've done it to Other people. I've gone to people and said, hey, thank you. I didn't want to hear that at the time, but you were right. You're right. Or if you weren't right, thank you for at least trying to identify what was different. Because even if you weren't right, I was wrong too. So for all those reasons, my whole thing is, like, I just want to be there as a. As a pillar, you know, as somebody will help you, like, support your own, you know, journey forward. Because you might be doing something that I've never done. You might be doing something you've never done, maybe that nobody's ever done. So all you can do is just keep, like, enhancing. Like, go for it, go for it, go for it. But be healthy, be well, treat people right, you know, and if you fuck up, let's try to figure out how do you make amends and, you know, figure out ignorance and how to, you know, grow from it. All that stuff is really where I like to mentor.

Yeah, I love that. Cool. I think I relate to that so much of, like, being on the other side of that. As someone that's 23 that started this game of, like, business, entrepreneurship, podcasting When I was 16, I initially had these thoughts of. Of, you see these aspirational figures or mentors or people that you want.

Can I ask you a question?

Yeah.

I know it's like, you know, you're. You're directing. Yeah, I love it. But this is where I'm always curious, like, you know, it didn't start when you were 16, so, like, where did you have an idea, like, before that, at some point, maybe it was something completely different. That was the, you know, the. The center point where you go, oh, man, that's really, like. My dad gave me a tape recorder when I was, like, 8, and when I hit record and play and I heard my voice record, and then I played it back, I think that was. That device changed. Like, that's me. Wow. Okay. I can ask questions with this. I can interview my mom about what's for dinner. Was there a moment like that for you?

Yes, for sure. So, I mean, for me, just the context. I grew up in Virginia, east coast. I had two older brothers and athlete my entire life. Played hockey for 10 years, played lacrosse, and then sophomore year of high school, playing football, and it was the first day of hitting practice. You know, pads are going on. You're having a great time in the field. Used to play sports growing up.

I'll tell you, I'll get to it in a second. I Wonder.

So, first day of hitting practice, end up getting injured. I've hit my head on the ground, my helmet's falling off. Next morning, can't move my head a millimeter, Get X rays. Doctor comes into the room and says, good news and bad news. Good news is you're not paralyzed. Bad news is you have to be in a neck brace for six months, can never play football again. And we have to really see like, where your spine goes and how it recovers to see what you can ever do again. And this is a 16 year old kid that I grew up since I was young.

And the word never. And again, when you're hearing that, it's.

Yeah. So it's like your identity, right?

Right, yeah.

Identity stripped away. And I walked out the building that day, just lost, confused, pissed off at the world. And it was during that six month period where at first it was filled with resentment and anger, but then turned to something similar that I can relate to you or just finding that path of personal development, like picking up biographies. And I grew up like, I was by no means a reader and I loved reading, but by following these different people on social media, that inspired me and that I was just watching. Picked up, think and grow rich.

So you were finding that you were looking for people, you were looking for reinforcement.

I think was like, I was curious, right? Like, I saw this guy, Gary Vaynerchuk, he put all this content on social media and saw him. And I think a lot of kids my age at that time or even today, they shut themselves off from opportunity by just not going deeper and like really diving down a rabbit hole and like, see how far you can go. And I think for me it was just like being willing to open it up and look in and then just immerse myself in this whole world of business, entrepreneurship. And by like six months later, I started an advertising agency in my local hometown of Virginia. Then I, I looked at myself and I'm like, okay, I'm following these people on social media. I come from a small town with no, like, business relationships, no true mentors in my life. How can I go talk to people that are doing exciting things? And the podcast initially was the excuse and ended up doing like 90 interviews in the first 60 days of having the show and just went all in on that craft. And that was the moment.

But, but now let me ask the ridiculous question and I expect a ridiculous answer. Like, do you, do you look back on the day you got hit and you hit your head as, as something serendipitous or A moment that. That defines you the way that you see yourself today. Or do you look at it like, no, I would have been a great fucking football player if I, you know, didn't take that hit.

Like, dude, I was. I was so driven as a kid in sports where, I mean, being five foot five and wanted to be a running back. I mean, chances are, if it wasn't the first day, I probably would have got hit or hurt that season. Right.

Fair enough.

My goal was go to uva, play lacrosse.

Yeah.

And I really had no other plans besides that. Like, both of my older brothers, they didn't go to college. I. I was taking AP classes and, like, took my school seriously. And then when I pivoted to immersing myself in entrepreneurship senior year, I took three classes. I was leaving at 10am every day. I was, you know, started my business doing interviews and I just completely switched, like, my entire being.

Yeah.

But I really don't know. When I think about who I would have been, right? It. It's kind of frightening.

I'd like to think that at the end of this life, it's, you know, there's a. There's a element of simulation and you're allowed to sit in a monitor and they go, like, would you like to see what your life would have been should the football thing happen?

Or.

You're gonna find this really interesting. You know, I. I had a routine that I was trying to work on recently where, you know, it's a little dark, so I'm not exactly sure if it's gonna play here, but the idea was, like, you're gonna pass away someday. There'll be a person meeting you and whatever, like, you know, the man upstairs or some liaison. They're gonna be. They're gonna be like, what'd you think of the car crash when you're 18? That was up, right? It was good, though, right?

You did good.

Good. Like, you gotta. Let's see, 90, 90 score on that. Like, it's almost like everything I believe my whole thing on it. And why I asked you that was like, I have to believe that. It's like life feels like it was meant to be. Like, if you take on all the challenges and you're willing to accept that it's hard, that the whole thing is fucking up. It's a brutal maze, but if you lean into it and you play it, you get these, like, moments of dynamic. Holy shit. You know, Success. Call it, or call it a number of things, they say success. And so I'd like to believe that, like, all those things that are traumatic moments in my life or capsizing moments are the things that someday you get to in the next life look at and be like, oh, man. You know, I lived. My human experience was one of evolution and growth and finding ways to turn failure into victory.

Absolutely. I love that and I appreciate you asking questions back. I think that moment, sometimes you forget.

Because you're sitting here like, wait, I'm allowed to. You're like, cut that.

For you. You said sports. I wanted to go back there growing up.

Yeah.

Playing sports.

Here's my football story. I. I signed up to play football. It was like 10th grade, Arlington High School. And my early joke, 1992 or 93, I said, on the first play of practice, I got fucking hit. And it knocked me right into west side Story. I was in drama. Like 10 minutes later. I was like, I'm never getting hit again.

I hated it. Oh, my God.

And it was only because I was such. At that point, I was very beta. I was very, like, non confrontational. I didn't like getting hit. I didn't like even getting the ball. I didn't want to be the decision maker.

What position were you playing?

I don't remember. Fear based. I don't know, like, wherever. Like the most scared you could be. I just remember I did it for my dad because my dad was a broad shoulder. I got his shoulders, my broad shoulder. He was a boxer. He was a football player. He went to Boston College. He still has records on the books at Boston College for like most consecutive foul shots without a. A miss. I mean, the guy was athleticism. I'm his only son and I just wanted to be in drama. I wanted to be in like Billy Crocker and, you know, anything goes. Yeah, I was like a song and dance man, entertainer. So one football play, one hit, I.

Was like, he quit.

I was done.

Gone.

No, no. Literally knocked me into drama class. It was like I. I realized my calling was acting like a football player.

Got it. Yeah. You can experience that, but not actually.

It's a costume. I don't want to be in the actual uniform, but I'd like to. But kind of the, you know, the cool thing there was as my dad's relationship, you know, it really, it was tested. But as. As we grew closer over the years, the thing that was so gratifying was the center of our lives was I was overlapping and I was involved in a lot of things in athletics that he loved because he wanted to see me do that. But it was like through acting or through Charity events and, you know, working with people that he grew up watching on the Bruins or that. And suddenly they', friends, they're fans.

Yeah.

So he got to see his son accomplish, and he also got to see that it could still. The arts is very much a part of the athletic realm as well. And so for all those reasons, it was a great way to, like, you know, the adhesive of my dad. And I still was, like, at the core. Sports.

Yeah. You know, that's incredible.

Yeah. He understood comedy was a sport. He understood it was very competitive.

Absolutely.

And it was really not as, you know, light and fluffy and just jokes and punch lines that we saw in Johnny Carson, too.

Right. Hyper competitive.

If I had to go back and you said, all right, reset, 1990, do it again, I'd be like, can I be a brain surgeon? Because I don't think I could go through some of the. If I knew what I, you know, naivete was the best gift that you could have been given as your, you know, in your youth. Because it was hard, man. And it was. Sometimes it was unsettling because, you know, you would see the people that you admired and. And not all of them were the happy faces on television. But then that made you understand, oh, I, too, am doing this as somewhat of a facade because I'm trying to circumvent that I'm very sad from some of the things that I experienced that I'm not very sad all the time, but I have a lot of this.

In me, deal with it.

So, yeah, so for a number of reasons, this. This racket is like, you know, you gotta. I think I said to somebody recently, I said, like, you know, start being introspective. You know, you're a young person, journey inward, because the better you get to know yourself. You'll be able to handle once you're under the magnifying glass, or you'll be able to handle when nobody gives a shit. And that is the loneliest, lonely. Like when you go through a period where you're like, I think I'm doing well, but nobody cares. Yeah, you'll say that. Nobody cares. You got to get away from that. And you start to realize this is the moment where you have to be your number one champion. The only person who's supposed to care in that moment is you. You're the only thing that is going to provide that door to open up. And you're looking for the door, and you're forgetting, if I do the work, then I might be able to just create that myself.

I love That I myself, I'm a big journaler. I try to journal and kind of like calligraphy. That's what Dave does. Meltzer, Jacqueline lives with Dave. He does calligraphy. Every day. Every day.

It's amazing.

Yes, yes, yes, of course. No, but I. It's funny because I. Whenever I got into journaling, I would write sort of these future based messages where I start every journal entry with like, casey, kind of like, what are you going through? I kind of talk to myself in like a weird way, but I. In the moment, I'm always like, okay, this is cool, but I appreciate it a hundred times more when I read it back to myself.

Yeah.

A month later, even a day later, you're like, wow, like taking the time to just be present and know yourself and kind of take that time.

Right.

I feel like a lot of people don't take the time for themselves and therefore they lose themselves in the pursuit of something else.

It's hard because when you take that time to. When you take that time to look at yourself, the. The reality is you're not gonna like a lot of what you see and there's gonna be things that, like, you know, when you're judging jury to yourself, it, you know, sometimes there's amends that, you know, you need to make. Sometimes we all make mistakes. You could hurt somebody, hurt people. Like, you gotta, you know, that's the. That is such a. It's a delicate, you know, it's a delicate moment when you finally realize, I want to be the best version of myself, but I don't really like me for a lot of reasons. And that's like, man, that, that transition. So it's not for everybody. And you understand why some people just put on the. The facade and don't ever want to confront that. But it's so gratifying when you do. It's the best way to living present. Know, you know, people that come or go into my life, it's based on who I really am and not of something that I'm, you know. Yeah. Trying to enhance or put forward. So.

Absolutely. I want to talk about the transitionary periods in your life where it's like we talked about Matt earlier of like embracing being comedian as you did, but then that turned into being in the movies and like, there's the business element.

Sure.

Like, for you, when did you start to just add on these layers of like, okay, let me go be an actor and let me dive in there. Like, what was that first experience?

Yeah. Yeah.

Being knocked from the field to the art. Not Being able to do what you love, but then have these opportunities, like being in these iconic movies, it was.

It was like, mesmerizing to get, like, those early phone calls where I'd come home to my apartment and, like, you know, Kevin Costner called me, got my number, like, you know, the heroes of mine, people that I. And to be invited into their sandbox to be able to play. And, I mean, I always wanted to act. I grew up playing music. I love guitar. I was singing. I was doing bro, you know, doing plays. So, you know, a Mel Brooks, who I grew up just. I mean, forget. I don't even know if idolizing is the right word, but to have him call me in my car one day and say, we're doing the Producers at the Hollywood Bowl. I'd love for you to come in and be Franz. And I'm like, is this real life? You know, and so to be able to have all those. To know that Stand up introduced me to somebody who then became a fan or was interested in how I operated. And then they say, hey, why don't you come over? And you go from the somewhat lonely, entrepreneurial, you know, guy on stage at the helm with the mic to then being like, now I'm just to going a piece of a puzzle with everybody else. And that's just as alluring. It's just as important to me because sometimes I don't want to be out front. I just want to be a part of the story. And how do I. How can I play that character? And, you know, it's so entirely different. Uses a different part of my creativity to show up on your thing. I'm making the movie. You're the guy at the gas station. But it's pivotal because the things that you say are going to, you know, domino effect. The rest of you go, that's. That's interesting to me. In the same way, if you said, now go make Madison Square Garden laugh. 20,000 people. It's like, oh, I get to come at this in a completely different way. And it's. It's important because it's important to you, as opposed to stand up is like, what's important to me? And then everybody listens. Yeah, it's like, what's important to you? How can we put objectives together? I think that goes all the way back to being this lonely kid and feeling like, where do I fit in? I don't feel like I belong on teams or anything. So I think even at 51, I still sometimes to be very, like. It's like sometimes I just want to fit in sometimes. I just want that phone call. And weirdly, success sometimes makes people go, oh, I didn't call you because I just. I didn't want to. You're doing your thing. You're like, no, I'm just sitting here sometimes waiting for somebody to go, you want to explore an idea with me? And so when those doors started opening, I tell you, man, I was like. I was like, giddy most mornings. Giddy. I'd wake up and I'm not even kidding, I'd wake up and go like this. And like, I just lay in bed and be like, I couldn't. Like, what am I? Who's gonna call today? What tour date wants me? Like, there was a good stretch of time where it was like, all right, the hard, harder years are working, the.

Momentum is caught up.

I'm not. There's no part of the career yet that you get where it's like, either fall out of favor or you're whatever. Like, there's backlash. All the other good stuff that comes. Of course, I was in the middle spot where it was just.

How do. How did you think about, like, managing that time? Meaning, you know, opportunities, business. Yeah. Whether that's agents, you name it. Like, how was the business? I should ask, what was the business side of being a comedian then? And how did you think about it and how has it changed over time?

The business side was sometimes just as. Just as singular as the standup. Because I loved computers. I was geeking out over everything from early incarnations of aol Instant messenger, and I understood email and I was defragment. Defragging hard drives on my old Dell was that guy. When I came home, I loved. I'd go to Fry's Electronics. Out here was like. Or like an electronic shop. So I love that stuff. And what I found was the business side of it. Even some of the people at the time, my managers or whoever, nobody really got it. You know, I was a college age kid performing at a lot of colleges, and so I felt like even my first, like, admin page logging in. And I was a fulfillment center. I would package the cd, I would send it to you. Sometimes I would throw things in my kitchen, paper towels or I'd, like right now. Like, I was literally the, you know, you. You would sign up on my website, you would purchase. I would die. Okay. They sent me the money. I was doing everything. Wow. So for me, before it became like a bigger branding and business thing, I just enjoyed that. I was like, I'm still. I'm still kind of in control. And I'm. And I'm growing with the business. I'm learning a little bit more. I didn't know what a fulfillment center was.

Yeah.

And then suddenly I learned like, okay, there was now a place in New Hampshire that I could. They could help me facilitate the orders and that. So I learned as I went.

Yeah, I love it. And for people that don't know anything about the comedy business, obviously, it's like if you're doing tours, there's ticket sales and there's working with brands and there's acting gigs. Like, talk to me about the different buckets that they came into your life of. Maybe that's investments in companies or, you know, getting equity in deals. And think about.

It's very different now, though. You know, Casey, it's changed so much because, you know, even at that time, stand up comedy, you know, coming out of the. Instead of comedy was pretty much dead in the 90s. The record deals and stuff happening in the early 2000s, like, it wasn't what it is today. It wasn't looked upon as like, you know, in. You didn't have podcast, you didn't have the other 23 hours of the day to like, enhance. So there was no advertising, nothing like that. So the way I do business now is very different for. But for that, like, decade, it was really like, okay, investing was like investing back into like a dynamic website at that time. Right. Something with more whistles and bells, maybe. Seeing if sometimes I would actually be my own promoter. I would rent out the venue. Like, sometimes I would actually find arenas on an off night. I could find like a B or a C arena and say Edmonton and say, say, hey, it's not hockey season. What do you guys have in there in February? And they'd say, nothing. And I go, if I wanted to rent it on a Tuesday, like a big Elks Lodge or something. And they'd be like, it's 35,000. I'd be like, I'd look at my bank account, I'd be like, I'll do that. Because then I knew I could set the ticket price.

Yeah.

I have my friends come up and sell merch, which.

Wow. So you do that? You book an arena?

The whole thing.

Yeah. Wow. Just full. And you've done that. Even speaking to your special. Like, that's all self. Self funded, self produced.

Even here? The one that I shot here. Yes.

Where do you. Why did you not why. But what made you decide to do those things? The entrepreneurial spirit is obviously within you, but that's obviously compounded over time to then doing specials and controlling everything when, you know, I'm sure you could have gone in so many different directions. What led you to just stick on that path of doing it yourself and controlling it?

Good question. Because it brings a lot. Brings a lot up when you say that. Because it's like some of it was crooked deals, you know, bad. Bad business people, bad business affairs. Something I also try to teach people like, you know, you're going to meet somebody who's going to shake your hand, they're going to love you, and they're going to. They might. But when they take that contract, there's another office down the hall called Business affairs. And they don't love you.

Yeah.

They don't give a shit. They just want the best deal for that company. So you got to be prepared to go into a meeting and say, this is exactly what I want and what I want to bring to the table, you know, for you, for your company or your organization. And I think that, like, when I look back on that time, and really, for me, more than anything, I don't hope this answers your question. I mean, in a roundabout way, like, for that time calling an arena and doing all that stuff, I figured it out on my own. Yeah. But also some of it was because I was like, man, I'm getting some bad business deals with people. I'm not walking away with what I anticipated. But even more mission critical was like this idea of learning about IP intellectual property and then learning about royalties and mechanical royalties and looking at really, what am I putting out there? And how can I someday. Initially, the idea was, how can I someday just have it and give it to my kids? But then learning you can't because you don't. Like, there's certain things that I have in my catalog that I don't own. Like, HBO has vicious circle.

Yeah.

HBO came in and said, we're gonna pay this much money, but then years later, it's like, I don't have a say.

Yeah.

Unless I go to HBO and try to do a new deal. Or maybe, maybe. Maybe there's some haggling or do this for us or whatever. But the point is, because it's like, I can't stress to people enough. And, you know, because you're in this position where you built this yourself, if you can find people that will support you that aren't the billionaire corporations that are gonna, like, put the money in but then own everything based on the paperwork, if you can find those people that are, like, true partners, on the come up.

Yeah.

Then it's. You have to just believe me when I say this. Of course the money's great. The money is fucking great. The money buys you the cool car, and the money buys you, like, the better steak. And the money buys you, like, you take the person out on the date. But I promise you, years later, you won't care about any of that. The car will get old, there's always a new dinner, relationships change. But you'll go, why don't I own my shit? And what if you only have one great moment and then you go off into something else? Something else that you might find great, but it's not as lucrative. But you don't own the one piece I get. Look, I have goosebumps now talking about. You know why? Because I want you to own that.

Yeah.

And I want to own that. And if it fails, at least I own it. And I can't say, man, this thing that we did together failed because they paid for it and they didn't give a shit. Yeah, fuck, we should have finished it. So I say, finish it. Get it paid for. Figure out how to do it yourself. Figure out how to rent the arena with your own pocket change or whatever you got saved up. At that time, I had, like, 400 grand, and I'm, like, betting on myself. 35,000. Okay, I brought in 80. Okay, another 35,000. I just brought in 90. I'm gambling on myself. If you have the content, well, then you can go to those billionaires and say, sure, but I want it back. You can lease it.

Absolutely.

Here's a window. And I did that with Troublemaker, which was the special that I did before COVID and I leased it to Showtime and that. I leased it to Comedy Central. And you. You know where it is now? It's on my desk. I haven't even re released it yet. There's a company that came to me recently and said, hey, would you like to put it on avod or something like that? I was like, yeah, we could talk about that. And I just love that you own it, even if it's doing nothing. Now you might say, well, that's stupid. You should be making money. No, the point isn't just to make the money. The point is I pull it back sometimes. And I go, I just want to hold this and sit. Maybe there's something in it. I'm not, like, standing by me for any reason. Maybe it's none of your business. But I get to decide, yeah, when it's out in the world and Then when I'm ready for it to get pulled, I get to do that, too. So. IP man ip. It's all about ip.

Love how you put such an emphasis on that over time. And I want to ask, when it comes to these lucrative deals, how is being a kid from Boston that, going back to the beginning of this interview, that grew up in, you said, a tilted household, how has your mindset changed on money over the years as you got more successful? Obviously, you're. You know, you talk about the better steak, the better car, the better house, the piece that comes with it.

Yeah.

Like, what would be your advice to your younger self? Just on. On money. And how has your mindset on money changed?

We were like a welfare family, so we had, like. We were in the system. We got, like, food stamps and free lunch tickets. When we were short on money, the Salvation army would come by and sometimes put oil in the furnace, like, so we could have heat.

Wow.

I started paying board when I was 15. I would kick into the house. I worked. I was a dietary aide in a nursing home. I was in a convenience store marrying the labels. And I would come home and I make 60 bucks, and I have to give my mom 10. I hated it. I was literally like, mom, you're like a. It's like, you know, this is. This is not. You know, you're my mom.

Yeah.

She was like, nope. Everybody contributes. Everybody contributes. And so I. I had a understanding. Money is important if you want to have, you know, keep. Keep nice things or keep the roof over your head. But I also didn't put a lot of value in money, understood that money could provide more ways to be creative. And so I think as I got older and I'd gone through, again, ups and downs financially, not everything I can get into right now. But having had not and then had and then have not and had, it only ever provides me a chance to be creative again. And if I have it or I don't have it, that remained. And so money always, I feel like, just reminded me that it doesn't change who I am. You know, it doesn't change anything about how I live my life. If we have it and there's a nice thing to be had, cool. And if I don't, I'm still gonna wake up and go, like, how do I figure how to make something today? Create something today? And so, yeah, it's like, I have an interesting relationship with, you know, with money, because I also go, like, I've made enough now to where I've invested in companies I Buy homes. I put it back into my, you know, company, other companies. And so now I'm weirdly at a place where I'm like, oh, I don't need to even think about it anymore. It's. It's working for me even away. But my first thought every morning is still, how can I make something today?

Yeah. You know, that's incredible.

Yeah.

What is your. You're, you know, it's August 2023 now. Like, when you wake up, like, what are some of the daily rituals that you have? I mean, you're. You said you're 51, right?

Yeah.

You clearly take care of yourself. Like, what is. When it comes to.

I'm in there every day, I go.

Okay, yeah, talk to me about your daily routine.

I have a swim tether and it keeps you right in the middle of the pool. So I put on like little goggles. I put on underwater headset. I listen to podcasts. Self effort. You know what kind of podcast?

I'm curious.

Anything. Anything I can find, honestly. Like, I'm the kind of person that, like, I can try just whatever. Any podcast, if I feel like. If it's just an interesting. I've never listened to a podcast about how to build an extension off of your house. I know nothing about that.

Love that. No, like symbols, though. No. Like key things that you listen to.

I mean, I like stuff like, you know, smart lists or, you know, some of the stuff that I'll key in it. Like, I. I even like excerpts sometimes. People put like a bunch of like best of stuff. But you listen to anything? Music. Audiobooks. I tend to listen to music sometimes. Nothing. Just ruminate.

Yeah.

You know, when you're in one place and you're in the water, there's something. I don't know if the Pisces in me.

I just.

I'm just in that. And the thing I like about the tether is I'm just in one place. You're not doing laps or anything. And I've got a little breathing apparatus and I'm just. I do it every day. It's a. It's 30 minutes and it's the best burn you can get. It really like you get out of the water and you're. It's refreshing, but then you're sweating for sure. And you look down and you're like, oh, that's a 800 calorie burn or whatever it might be. So that's every day. I. I didn't even know what keto was growing up, but I was Keto. What I I don't think I've eaten breakfast my whole life.

Wow.

I've always woken up, you know, I don't get hungry in the morning. I've never been hungry.

It's fast. Yeah.

Yeah. I basically am like, yeah, keto intermittent fast. I was like, oh, shit. Like, I. So I don't usually eat till about 2, but everything from when I get up at 9 is, you know, getting the dogs put together. Kelsey's already gone because Kelsey is Pilates instructor. Yeah. So she's always like her early. People do their classes before work. So she's out the door like 6 o', clock, get up, hang with the pups. And then. I love the moment. Sometimes I'll have, like little half of an energy drink or something. I love the moment. Walking into my office and I sit down and fire up that computer and go like, okay, like, what? What's new coming in. It's. I'm still like a kid. Like, who's interested?

Like, yeah.

You know, I check the social media, the DMs, you know, again, get, like, back in the mix. It's a little of everything. I like that. It's an equalizer. People keep you humble. People keep rooting for you. People champion you. Some people don't get you. It keeps you very, you know, if you can take it, the slings and arrows sometimes, like, it's kind of good because also, like, if you're really healthy with yourself, no matter what somebody says, even if it's up and I've read Fucked up, you kind of go, I'm okay. I'm okay. I can read this. And I better understand myself because I can go, wow, this person wrote this. It's kind of funny. And then fire up the computer. And then I think the thing that right now, in real time, I'm the most excited about is I'm doing a documentary with an incredible group of people out of Canada. And we're telling a story that I can't get too much into.

Okay.

Legal reasons, I'm under contract, but I'm telling a story about a hardship with my brother, who is my business manager. Yeah, it was at the peak of my comedy career. And it was probably at the saddest moment of my life because my parents had passed away. And then my brother did some things that were so malicious and just completely unfathomable. But it's. It's the funniest moment of my life. In the peak. Right?

The peak.

Peak. Like the. This is silly.

Yeah.

But it's the abyss of sadness in My life. And we're doing a doc about it, and we're telling this story. We have unbelievable people and the crew. But the people like that are. That are stepping up to do interviews. Of course, I've done a lot of my interviews, but the purpose of it is to go. If I can take this moment in my life, the. I'll say the hardest, even though it's like, it's the hardest moment of my life. And I thought it even when it happened in real time, happening in real time now. I said, if I can entertain people with this someday.

You thought about that when it was happening, I knew.

Even when I was broken and busted and I was a puddle, but I was already having notions of if I can. If I can come back from what this is, even not knowing what it was, whatever is happening, if I can, I know it's gonna be the most empowering, entertaining thing I ever do in my life. So I kind of feel like I'm probably making the best thing I've ever made and might ever make for the rest of my life right now. That's my morning every day.

I know you can't talk about it too much, but is there, like, a specific date in mind when people watching or listening can expect this?

Well, the hope would be. I mean, this is where you start getting into, like, of course, the PR of it. Want it for, like, film festivals next fall.

Got it.

So I imagine they're gonna, like, that's exciting. Oh, man. It. It's exciting, too, to be able to actually look at these moments and go, wow. Like, I can laugh at some of these things that I wasn't laughing at. Yeah. And I can actually be emotional about things that I wasn't ready to let down my guard. And I'm. Yeah, trust me, it's hard. I leave the set some days, I'm.

Like, that was too much.

I opened up a little of them. I gave everybody my power. I passed my power on the whole room, and then I forgot it was in the room. And I came back. Who's got my power? Can I please? So for a number of reasons, I. As you can tell, I'm really stoked about it.

I'm curious. I am a big reader, and whenever I read a book and someone's going through the darkest, deepest moments in your life as a reader, you're just like, wow, I appreciate how much they're sharing. But then I pause and I'll think, damn, that was probably hard to, like, put the words down and say, okay, the world's gonna Read this. Like.

Yeah.

How do those thoughts.

Oh, wow.

Come into your mind? And how do you think about that?

Can't think too, too much about it because that's almost like being a comedian, being like, this is funny, I'm funny. It kind of.

It.

Yeah. It's like the ebb and flow. You just gotta kind of surf it. But I. I have left the set on a couple of occasions and just Kelsey was with me one day when we did eight hours of like, eight hours of me, like talking through my whole life.

Yeah.

Which I've never done. I haven't done up until that point. I've done therapy. I talk about excerpts in my life and fragments and things, but I never walked somebody through. Excuse me. I've never walked somebody through the entire thing. And what that did to me emotionally, I was not expecting. And so, you know. Yeah, if I think about it too much, I'd be like, oh, boy, it might be some memes out there at some point and like, you know, but. But I'm ready for it. Honestly.

What do you, like, what would you say you learned about yourself through that? Because even me, I. You said doing the dog from the eight hour session. Because I feel like I've. Not many people just sit down for eight hours and they. In a. In the context of putting together thorough documentary. Right. Like, we could all have conversations with myself, you can shoot a quick 10 minute video to yourself. But it's rare that I believe a human that then you get to really sit down and walk through your life. Like, what did you learn about yourself having that depth of reflection?

I can only answer with the first thing I thought of, and that's that I made my mom really proud that I sat there as the man that she really believed that I could and should be. You know, she raised him too.

Yeah.

But I knew, I knew in my heart, like, you know, here's the thing. My mom prepared me for this career, gave me the incentive, the reinforcement. She was my compass. She was my cheerleader champion. And she loved coming to shows and she loved to laugh, but it was always her and I. And when this thing happened after she passed away, it was like, I remember just kind of daydreaming on it one day. And whether it was her voice coming through or me thinking what she would say, it was like, all right, honey, now do everything again, but by yourself. Prove to you I knew you did this for me and us, but now do it again. The whole thing. From nothing to something, but do it for you. Wow. And so sitting in that chair. Sometimes I turn to Kelsey or whatever, just kind of, like, take in the environment and be like, I know that she is so proud that I'm okay. I'm good.

That's incredible.

Yeah.

I appreciate you sharing that. For sure.

Yeah, man. Thank you. You almost got me. I felt the tear duct to do that thing where it kind of. I talk about my mom and I go there, man, she was the best.

And we could go deeper, but I want to change the tone a little bit.

Okay.

When you think about. And again, I appreciate you sharing that, and I'm looking forward to seeing this when it comes out. For sure.

Absolutely, man. You'll be at the premiere, you'll be at one of the showings, and we'll be there, and hopefully it's.

Maybe we'll do around 2 of this after it comes out.

Wouldn't be a better idea. Okay, cool.

When you think about comedy today, like, what makes you laugh? Like, your humor. When you go and see a comedian, like, yeah. What do you look for and what makes a great comedian for you as a. As an audience member?

It's still a hodgepodge. It's still everything. It's still the comic that goes on at the end of the night, and he's outlandish, and the crowd's dead and tired, and they're just gonna say some shock shit. And it's still the person that's brand new, and they're not very funny, and they're not very well prepared. But they said one thing that worked. Walking into the club, looking, what's the lineup tonight? I know where I'm up. And then be, oh, Nikki's in here tonight. Or I haven't seen Maz in a little bit. Or, you know, Kevin Hart swinging through Tiffany. That, to me, is still the stuff that makes me the unexpected and the randomness. It's so simple to say that, but it's what I loved. The first year. I'd walk into a club, I go, okay, I'm not on. They don't know who I am. I know a couple of people on the lineup, like some Boston legends. And then you'd hear people whispering, hey, Rob Williams is in town. He might swing through here tonight. And to me, that was always, like, the thing that would incite the most laughter and stuff for me is like, the journey. The people sitting in that room, that's the show. And once everybody disperses, that's it. But what happened in that room, whether you liked it or didn't or were offended or loved it or laughed where you shouldn't have laughed. Like. Like, that's what I'm laughing at more. I'm laughing standing at the back of the room. I'm laughing with the experience of everybody sitting there and watching somebody who most likely is a friend or a peer, and I'm seeing them get it. Get it done in some way. It's awesome.

That's incredible.

Yeah.

How many today, when it comes to, like, you live in la, how often are you going to comedy clubs and still in that scene of wanting to see who's new and what's high, but also seeing friends and just being in that serendipitous of, oh, swinging by, like, what does that look like in your life? Is someone so in it.

Still love the weekend. If I'm not on the road, it's like, still weekend shows. Always Friday, Saturday. It used to be every night. I forced myself about 10 years ago to go Sunday nights, Sunday night off. It used to be every night. All the. I have journals from, like, 1990. Well, 93, when I started really getting a lot of work, probably until around, like, 2010. And you're like, did you ever not go out? I was doing a show every night. So I try to get on. For me, a good week now is if I get on four nights a week, I'm more articulate with what I'm there to do, even in a limited time. I used to be able to do, like, 15 sets in a week.

Yeah.

And be like, well, how much work did I do? Some of it was just like, I just want to be funny tonight.

Yeah.

But now I can go in and like, okay, that 20. I did that last night. That's good. I need to tweak that a little bit. Let me piece. Bring that piece in for. I like to get five sets in, but if I can do four a night, then that's. That's. That's good for me.

That's great.

Not Fortnite. Four week.

Yeah, four week.

Yeah, four night. No, like, New York City was. Let's see, three show. I go Comedy Cellar, the Boston Comedy Club. Back to the Cellar, the Wah. Back over to the Boston Comedy Club, up to the Comic Strip, back down to Caroline. Sometimes swing through Gotham, Dangerfields.

Oh, my God.

You do eight sets. Eight, nine. Everything was cash. And then at the end of the weekend, you just pull out a fucking wad of money. It just, like, you just look on the table and you'd be like, for slinging jokes, you know, wow. Wow. It was crazy. So, yeah, five nights a week, I'M happy. I'm happy.

It is so. It's such an art. And then I'm sure, like, as from the wads of cash, the large checks, you're like, I'm just telling jokes out here.

Yeah.

It must be such a surreal feeling.

Yeah.

To take it to that level that you did.

Bonkers.

It's insane.

Yeah, it really was. And there were nights that, you know, like, during the arena, you know, I've had, like, arena runs where I'd be, you know, I did like, man, I think over two year, I did like 181.

Wow.

Like, coming back and doing another arena again, like, I did every single one of them. I don't think there was anything past.

Like, when you were doing this, like, you were one of the first to.

Do for that era. Yeah, yeah.

What were people telling you, talking to, like, the mentors say, like, did you have people in your ear? Like, what was the mindset of the industry then?

Yeah, nobody. Nobody was in my ear. Everybody was like, what do I do? How do I. You know, it was like I was in Del Dane, but. And of course, the industry is just gonna, like, if you're the flavor of the whatever that is, month or the year, they're like, yes. They're just like, whatever you say they're gonna, like, go with. But the people that love and care about you and like the graduating class of comics that I came up with, you know, the real, like, no bullshitters. It just felt like the most creative streak you can imagine because I wanted to make sure every night if you saw me last night, I wanted you to feel like there was something different happening the next night. So it was just. It was all passion and creativity.

Yeah.

Yeah.

What do you have a specific process that you go through when you were, you know, coming up with jokes, coming up with stories. And how has that process changed over time?

It hasn't changed a lot except for the amount of time I like to hold onto a material, you know, probably over the last. Actually since like 2002 or 3, I was like, I want to do it. Lay it down on a, you know, an album or a special. And then I want to move on because I want to investigate something, you know, else that also keeps you honest because then you're not like, road dogging it with the same routine and people going, like, I saw you do that one five years ago. I've never written anything down ever.

You don't write anything down before any shows?

No.

Or, like, the preparation. Wow.

Ever. I found when I tried to Write things down. Early in my career, I was so disheartened, I'd be reading my own joke and there's just something about it sitting on a page with no laughter around it. I was like, like, I get it. I hated it.

I get it for sure.

So I tried to write, didn't. And then I brought a lot of my improv background. And what I started to realize was where I wanted to get to in comedy was it doesn't have to be so finessed, it has to be real. But there still has to be like a three act beginning, middle and end to a piece of material. I'm a storyteller, not a joke teller, right? So for me, it's like there still has to be three acts in a story. So it's like authenticity. How can I be authentic? I treat every crowd like if I was going into a party and I was going to tell you the funny story, I would adapt it for how you react and the tone of the. And so that's my stand up, my standup is improvisational. But the mechanics and things that I've learned and the tricks of the trade, my cadences and all this stuff and like, I know where to stand. I know where to trick you into thinking I got it. It. I know where to make you think I'm insecure because it helps the joke to. For you to think. I don't know at this moment if I'm. If I should say this, but I know I'm gonna say it. And so the gears, all the pulleys and the, you know, little tricks and all that stuff. And at the heart of it, something called LPMs. That's laughs per minute. You want to have LPMs?

Tell me about LPMs.

LPMs, last per minute. It. It's the difference between a one man show, that might be a long story with a couple of antidotes, kind of humorous, right? And then an ending that may or may not be funny. That's a one man show. At the end of a one man show, you might say, like, but. But who knows what's gonna happen tomorrow? They're gonna applaud. The whole thing is, with me is it doesn't matter if the, the story hit harder last night wasn't as good tonight, or some things were really funny Friday. In the beginning it was a little wonky. I don't care about any of that. I know where it's going and I know I'm gonna get the LPMs. That's the laughs per minute. That means I'm gonna Keep you laughing because it's comedy show. I'm gonna get to the destination, which is the end, the tag, the button, and it'll be different every time I tell it, because that's life. Life is more improvisation than formulaic. And I don't like formulaic comedy. I can enjoy a comic that writes haiku esque formula. Like, I say this, I say this, I say this punchline. I respect it. I could never do it. I love it. I wouldn't want to do it. But I like that the crowd, I think early on in my career was like, you know, if a person in the crowd is laughing and loves me, great. But if a person in the crowd, I'm not their cup of tea. I still want them to be able to watch me and go, but I'm fascinated by this guy. And I think that comes from truth. Truth is fascinating, even if it's not your truth. You can't not be interested in somebody's truth. Authentic truth. So I'm trying to, like, I'm trying to. And by the way, I'm talking to you, like, I know it all. I'm 32 years in, dude. I sometimes seriously go into the club and I'm like, I feel, like, green and brand new. And there's something that I'm like, I don't know how to do that still. And so I'm always trying to figure out. And you're never done.

Yeah.

You know, you just rely on certain things and they go, but can I take them here now?

You know, I really, like, from the context of podcasting, the first, like, 30 interviews I ever did came. You know, all the questions prepared you quickly. I go back to them sometimes just to, like, experience the growth and listen to it. I'm 17. I'm nervous. The camera's shaky. Right. And it's just. I quickly learned what not to do. Right. Writing down the jokes, writing down the questions, and keeping it conversational. Yeah. Like finding your style, of course.

And you had. You had to have 30. Not that they were. I'm sure there's a lot of great stuff in there, but 30 moments where there's mishaps or. I used to do a thing where I would. I would tape my set in Boston, and then I would fast forward it. I'd watch it in fast motion because then I could see all my ticks, and I saw there was little movements and things that. In fast motion. I saw that I had a nervous tick where I kept, like this, and I would see it in fast motion. I kept doing this. It was this weird thing that I was relying on that I was like, I need to take some of that stuff out, because all those little things that are not necessary are distracting from authentic movement, things that are really in my musicality or mechanics. And so I was looking at things as like, yeah, if I don't need to do this unless it's part of the joke, I shouldn't do that. And piece by piece learning that's uncomfortable for a crowd when I do that. They don't like that. I saw a comic recently, and they were. They were sitting on the stool, and just something was very distracting. And I remember watching being like, I'm not going to say that to that person, but at some point, they might go like, man, if I didn't do this one thing, I'm. The focus might be even greater for me as a, you know, as a storyteller or whatever. So constantly trying to figure out, like. Like you did with those first 30. Like, yeah, how can I just be more proficient, you know, and curious, make it disappear to where People don't see any of our professionalism here. Like, we don't get really. I think. I think as you go on as a performer, there should be less awards or nominations. There shouldn't be any of it because you don't look like you fucking work or try. You know, if you're not winning anything, well, good for you. You probably blend in so well as that actor or performer that nobody thinks you're doing anything that warrants an award.

Dude, that's great, right?

For sure.

Yeah, absolutely.

That was just a nice way of being, like, that's why I've not got an award in a long time. Oh, my God. This covered my bases right there. And that's why I don't have an Emmy nomination this year, because it was.

Just like, hey, you live your truth. It's right. It's probably like, me, I'm. I'm, like, moving my hair around. I'm like, I keep doing that. Let's. Let's not do that anymore. No, this has been great. A couple more questions.

Oh, go for it.

As you think about the future, like, you're young, you're healthy, you're excited, you're creative, like.

Like youngish. But we.

20, 23. There's so many ways to, you know, age backwards.

Yeah.

Like, how do you think about the future of your life? Like, you're still doing comedy, you're still creating. You. You're in this setting of your life. It seems you're at peace here. At times. And you're creating new documentaries. How do you think about the future and what excites you? Right, like being from the small town to going on this incredible run to still being in your prime and really just in a creative act. How do you think about the future?

Well, stand up always excites me because it's always an evolution. You know, the comics I grew up loving, the Carlins and the Priors and stuff. It's like, it's. It's always another part of your journal. It can be. You know, I. I saw Jerry Lewis doing shows at 87. I hope for the rest of my life I get to, you know, testify in some way as a comic. But I don't think. I don't think people have seen me at full power in terms of both behind the camera and ways that I've been producing and hoping to build up that repertoire of directing. But even more importantly, it's just like being a leading man. In the time I was the guy, you know, employee of the month, it was awesome. But I also realized, like, there's more to me, and I want to explore that. And so I feel like the best is ahead in terms of how somebody could utilize me in a role that may be a little dark or gritty or caustic or weird. And yet if you need that, if you need the comedy or you need something that's going to enhance or, you know, lighten a moment, I bring a lot to the table. And so I feel probably most excited to go. Who's gonna. Who's gonna figure that out with me? You know, I hope I get that opportunity again. Is like. Like, these are things that. Lady luck and preparedness and all that. And then you just hope. Actually, to be very honest, I can't say who, but I got a phone call very recently from a producer in a company that I'm like, I've been big fans of. I couldn't believe this guy called me out of the blue. He's like, hey, I want to grab lunch. I have you in mind for something. And that's as far as I'll say for now. But knowing who they are, knowing the kind of stuff that they do, which is very different from what people know of me now. He was like, I kind of see, you know, in a thing that, you know, is really going to be kind of, you know, dark and twisted and really different. Are you interested in that? I was like, oh, man, are you kidding me? Like, I hope once people see this documentary, they might be able to go, okay, there's other areas to explore. And all I want to do is take all that stuff that's, you know, happened from me or to me and put them into great characters or help you put it into something that maybe I'm behind the camera. And we go like, now, let's tell your story in a way that's, like, gonna challenge people. So I do feel like that's exciting. It's a. It's an exciting era. And getting married and feeling like a.

Month out, you're getting married.

I know, I know.

I just feel like.

I feel like. Yeah, I. It's so exciting. I know. When you feel like you're onto something, and I kind of feel like I'm in that place where I'm like, you know. Yeah, it's a good. It's a good time.

I love that.

Yeah.

No, and a month out from getting married, I'm sure that's just this whole other aspect of your life that's the excitement and always wanted it.

And it was one of those things that kind of eluded me, you know, being young and in the industry, coming breaking through in the industry when I did. And then, of course, like, I'm a young guy in the industry, and I'm, like, taking advantage, and I'm sowing oats, and I'm doing, like. You name it, I'm out there and I'm enjoying it. But, you know, the. The catch. The catch 22 is like, you know, we're all on the clock.

Yeah.

And it's. And it's realizing. And thank God I realized at a certain point. Point, you know, some years back, like, man, I need to focus that same energy into love.

Yeah.

I need to focus that same energy and preparing myself for somebody who wants to come in and not just be on my ride, but, like, we share. We share something together. You know, to be able to have that, you know, I was pretty. It was my ride for a long time. It was like, if you came into my orbit, you know, it was like, all right, you. This is 24 7, the business of Dane Cook. And to have gotten to a place where I'm like, I want to be just as interested in my partner, but I also want to have, like, here's us stuff. Here's my stuff. Here's your stuff. And, like, I think going into this next era with that is, like. Makes it like, oh, wow, I'm at the beginning of something that.

Yeah.

You know, I'm in new territory with a person I love. So it's. It's kind of cool.

That's exciting. Yeah, I'm super excited for both of you guys. Yeah, thanks. I can't wait to see all that.

Appreciate that. We'll take cash gifts if you want to leave it here before you go.

Oh my God, I gotta end with this. Just. If you were to reflect on your life thus far and give your 18 year old, 20 year old self a piece of advice, comedy advice, life advice, anything, what would that advice be and why?

You know, I think that I was in a lot of pain when I was a kid. More than I even knew. I. I didn't even realize how sad I was and how much pain I was in. I was stronger than I gave myself credit for. I would not have said at the time I was strong at all. I felt very. I felt almost feeble, you know. And so I think I would want to tell myself, it's funny because you go like, well, I want to tell them anything. You got to learn all this stuff and then you'll be happy later. But it would probably be, don't be so hard on yourself. Accept the results of your truth. It's okay if people don't like what you're doing. It's okay if they have something to say about it.

It.

Don't let the noise and the negativity. Sometimes that just comes with a person that wants to be quite literally in the light, you know, a person that like, wants to be a beacon in some way. Healing, comedy, entrepreneurial friend. Because when you put yourself in that place, you know, people want to sometimes take away your sparkle, as they say, because they want it.

Yeah.

And it's okay. Like, I wish I could just give it to those people, you know, I wish I could just say, hey, you know, I know you're hurting me to try to diminish mine so you can have yours. Like, I wish I could give it to you. I've written people who've written the worst shit ever about me. And I said, I don't know why you wrote this to me. I don't know why you would say that to me. But I hope you find the, the love that I have for what I do. I hope you find that wow, you know, powerful. Let them off the hook. So I tell myself, like, it's not just like, be happy with yourself or like love yourself. It's like, you're gonna get knocked. You're gonna get knocked on your ass. Wear it like a badge of like every time you get knocked. Be like, look at this.

Hell yeah.

You're only getting knocked if you're up. Yeah. Some people never get up to get knocked. So I probably just let myself know, like, it's okay. It's okay to get kicked and knocked and thrown down. Sometimes life, you know, you're down and then you're further down and then somebody kicks you and then steps on you. It's. Sometimes it's not just a down in it up. Sometimes it feels like tears of, you know, abuse or abandonment.

Yeah.

And I would just tell myself like all of those things are letting you know that you're right where you're supposed to be.

I love that. I appreciate you sharing that.

Okay. So I appreciate that.

Dane, this is such a pleasure having you on the show today. I cannot wait to just. Just continue to. To grow with you, to see you at all the shows, to see the documentary.

Yeah, man.

Where's the best place that everyone can follow you, stay in touch with you on socials and obviously stay in touch with this incredible documentary.

I appreciate you asking me that, man. Yeah. It's like, you know, you just tell people kind of like you can search me online and you'll bump into me somewhere. But I think I've been, you know, I really enjoy TikTok. I feel like TikTok's been kind of a fun place to, you know, to be able to share a little of everything. That's kind of what I've cultivated on there. Sometimes it's fun and outrageous and absurd and yet sometimes I can put some poignancy on there. But of course, Dane cook.com and all my tour dates for the rest of the year and ahead. So that's pretty much where people can find me in the digital realm. But I hope people will come out and see a live show, of course. Because nothing is better, nothing than live comedy. That's it.

Absolutely. Well, I will link all that down below. Dane, thank you so much.

Oh, man.

Thank you very much.

Thank you. I'd hug you, but we have this.

Hey, we're good. This is great.