
Making people laugh looks effortless, but behind every joke is an incredible amount of work and strategy. Great comedians deliver far more than entertainment—they offer a masterclass in human connection. They say the things we’re afraid to say,...
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Kyle Reed
Hey, it's Kyle Reed, co host of the why that Worked podcast presented by StoryBrand AI. I'm jumping in before today's episode with a big thank you. Thank you for spending your time with us each week, tuning in and sharing your feedback on how the show is resonating. In fact, I'd love to share some of your comments. Here's what you've been saying on Apple Podcast. Episode one is mind opening. Love the simplicity shared of how to create a framework. Such a great episode. Fantastic. Really interesting and useful for my work. Thank you. Love the new format. The last two episodes have been life changing. Keep up the great work. Here's some comments we read on YouTube. Awesome show. You all love it. Love the new series. Great episode. It's both interesting and applicable. Can't wait for next week's episode. This is why we do what we do here at StoryBrand, empowering you to clarify your message, connect with your audience and grow your business. And your feedback and comments help us make the show even better so we can keep bringing you episodes that deliver more insights you can use in your business and your life. So keep them coming. Leave us a review on Apple Podcasts or Spotify and share your thoughts in the comments on YouTube. Your feedback helps us know what's exactly resonating with you so that we can select topics and deliver new fun, value packed episodes. And if you don't ever want to miss a new episode of the show, follow why that worked. Wherever you listen to podcasts and like and subscribe on YouTube, thank you so much for being a part of this journey. We can't wait to hear what you have to say.
Donald Miller
Foreign.
Narrator
You'Re listening to the why that Work podcast presented by StoryBrand AI. If you've ever wondered why certain brands, trends or cultural phenomena find success while others don't, you're in the right place. Every week we unpack why something worked, then give you actionable insights that you can use in your own life. Now let's dive in with your hosts, Donald Miller and Kyle Reed.
Donald Miller
Kyle, how weird is it that you would pay 40 bucks? Go to Zany's here in Nashville, sit down, get a beer, get some chicken wings. They need to improve their food, by the way, at Zany's.
Kyle Reed
That helps.
Donald Miller
And watch somebody stand up on stage and do a routine that's specifically designed to make you laugh. Have you ever just, I mean, if you were like an alien and you came and you'd be like, what are these people? I don't understand what these people are Doing that guy's not actually saying anything. How weird is it that comedians exist is what I'm getting at?
Kyle Reed
Weird because to take it a step further, you know, we. We live in Nashville, Tennessee, and the last place I want to go to is downtown Nashville. And so the fact that on a.
Donald Miller
What are you talking. I love.
Kyle Reed
I. I guess I'm more curmudgeon than you. The last thing I want to do on a Tuesday night is to, like, get dressed, drive downtown, deal with parking, you know, walk through the crowds, walk through the bachelorette parties, and go sit in an arena and laugh.
Donald Miller
You go see big comedians if you're at breakfast couple.
Kyle Reed
Yeah, yeah, yeah. You're more hip and trendy than I am, I guess. But yeah, it's weird. What a weird thing. And we're all sitting in a room, like 20,000 of us looking in the center of the room and laughing to someone. Talk and laughing. Who have you seen, literally? Oh, so recently? I saw Chappelle at Bridgetown Bridgestone.
Donald Miller
I had tickets to that Chappelle Joe Rogan show for all my buddies, and it got canceled.
Kyle Reed
So he, when he came back, I saw him. I. I don't think I ever got.
Donald Miller
My money back for that.
Kyle Reed
I saw Bill Burr there. That was like six months ago. Seeing Bill Burr at Bridge.
Donald Miller
Did he sell it out?
Kyle Reed
Almost. Not as much as Chappelle. They had half the room closed off, so it wasn't. But I've never laughed at a consistent. Like, it was almost like a. Like I never had a moment to breathe because I was laughing the entire time. There was not a pause. Chappelle's more thoughtful. You know, you get a kind of a break and he's giving you some culture commentary. Bill Burr was just hit after hit after hit. It was so funny. So I've seen those guys recently. Buddies and I, when we go on, like, golf trips, we'll save up comedy specials and to break the drive up, we'll just sit there and listen to these latest ones. And that's so much fun. So, yeah, those are the last. What about you? What are the last kind of up and coming comics you've seen?
Donald Miller
I shouldn't position myself as a, you know, a collector of comedy shows. Betsy and I saw Seinfeld at tpac.
Kyle Reed
Okay, that would be a bucket list type thing.
Donald Miller
It should be.
Kyle Reed
Yeah.
Donald Miller
It's the best. It's the most sort of professional, dialed in master control of an audience I've ever seen in my life, and I'll say it now. Will ever see that. You Know, I love Nate Brazzi, obviously a Nashville guy. Super, super funny guy. Theo Vaughn is on some other planetary level of comedy he's coming from. It's almost like, hey, I'm Theo Vaughn. Here's comedy from Mars. It's just like, no, I don't know what world he's in.
Kyle Reed
You know, people think Elon Musk is an alien. Theo Vaughn is probably an alien.
Donald Miller
You could probably start that as a conspiracy theory. By the way. Theo Vaughn would love it. Yeah, yeah, he's super funny. One of the most amazing nights I ever saw was John Acuff.
Kyle Reed
John is a joke.
Donald Miller
Yes. I've known John for a long time. I met John when he was in high school. I met him at his house. I stayed at his house when I was doing a speaking gig because his dad had brought me in to speak in North Carolina, right across from University of North Carolina. And he was a kid, and he was a cool kid, great kid. And I still think of his kid, he's like 40 something. John did one of the most amazing things I've ever seen a human being and certainly an acquaintance do. He booked two nights at Zany's, worked up a an hour to hour to hour and 15 minute comedy routine, walked on that stage and crushed it.
Kyle Reed
Wow.
Donald Miller
Crushed. From the time he got up there, the time he left, my wife and I went and did two nights in a row. I might have given him them. He's not a comedian. Yeah, he's very funny. You listen to him speak and he's very funny, but he just nailed it. And you know, I knew as a speaker, never been a comedian, but I knew how hard. What he just did was how hard a work. I would equate it to training for an ironman intellectually and delivering. The audience loved him. He was great. Kudos. So that was one of the coolest nights I've ever seen.
Kyle Reed
The first thing I kind of really. And I think, you know, I think if you ask someone listening to this, they probably would. Would circle around. This answer is just the authentic side of things. So I came across this clip of Andrew Scholz, who's one of my favorite comedians. He's got a great podcast.
Donald Miller
I've never heard of him.
Kyle Reed
Yeah, he's.
Donald Miller
He's probably extremely popular.
Kyle Reed
Yeah, you know, you only like the up and comers. And so I came across this clip and I think he did a better job summarizing than what I can. But I wanted to play this clip because I think one of the reasons why we need comedy or like why?
Donald Miller
Andrew Schultz.
Kyle Reed
Andrew Scholz. Scholz Sholes. Yeah, I think that's how you say it.
Donald Miller
Spell his last name so folks can find him.
Kyle Reed
S, C, H, U, L, Z. Andrew Scholz.
Donald Miller
Sounds good.
Kyle Reed
Yeah, he's great. So. But I came across this clip and I think he kind of summarized why I think there's comedy. So let me. Let me just.
Donald Miller
Why it exists.
Kyle Reed
Yeah. Like, let me play it. Let me play it.
Andrew Schultz
The other part. Authenticity. I've always been drawn to. And we'll wrap this up right now, but I've always been drawn to Larry David and I try to figure out why. Larry David was this amazing character that breaks all cultural barriers. Anybody you meet that has experienced Larry DAV loves Larry David.
Donald Miller
Right.
Andrew Schultz
He's not just old Jewish people's favorite comic, he's young Puerto Rican's favorite comic too. Right. Why? And it's because Larry David is an experiment in authenticity. It's. What would it be like if you were your true self 24 hours a day. Right. Hey, can I have a bite of your sandwich?
Kyle Reed
No. Why not?
Andrew Schultz
I don't like your mouth. We all want to say that, but don't. So when we see somebody say, say, we gravitate to that. And I think that what I always believed is I was going to do authentic material. I was going to do material that came from me. It hits you in your gut. I don't do material for how you want the world to be in stand up. I do material for how we know the world is down here.
Kyle Reed
So when I came across that, I was like, well, he just summarized how I feel.
Donald Miller
Yeah.
Kyle Reed
But I think that's which, by the.
Donald Miller
Way, says everything about comedy. He summarized how I feel. That's one of my six reasons that I think comedy comedians exist. Reason number two was they say what we think.
Kyle Reed
Yeah.
Donald Miller
Or their ability. They have a way of articulating what we think about something totally that most people wouldn't have spent the time to actually sit there and try to articulate it.
Kyle Reed
And what I love about that is he doesn't say it in the way my dad would tell me how to say it. He makes me laugh, you know, so it's like your dad's like, here's how the world works. He says it in a humorous, story driven way that makes me laugh while also putting in authentic truth inside of it. I think that's what we're drawn to.
Donald Miller
You know, Reason number one and number two for me were, one, they say what they think, and I think we admire somebody who actually will Speak their mind. They're not being careful, right? Of course they are being careful, but they're not being careful in the way that we are careful. And there's something about comedians is there's still a part of them that's feral. And there is something that is intuitively interesting about a feral human being. Now, let's say you got a pet dog. You don't. You have cats?
Kyle Reed
I don't have a cat. Not cats. Let's have cats.
Donald Miller
Now I have two cats and a dog. And you know, they're great, but wouldn't part of you want a cat that's like 10% bobcat? Yeah. To be honest, just a little bit like, could kill me.
Kyle Reed
Yeah.
Donald Miller
You know what I mean? There's something that's just. That's just kind of interesting about. We have this one cat, we got these two cats at a shelter. One cat, Trout, has a look of a wild jungle cat. It's not like a gray and white cat. It's kind of like a yellow and gray cat with these weird looking eyes. And I'm like, that's my favorite. Because it's kind of feral and kind of dangerous.
Kyle Reed
You don't know what it's gonna do.
Donald Miller
Sometimes you don't know what it's going to do. And I think that they think. When I say reason number one is they think they're slightly feral.
Kyle Reed
Yes. Well, I think too, to jump on your point there, as we go out throughout our life, we kind of know the expectation of what's gonna happen during the day or in a conversation. It's kind of organized. A comedian will disrupt all of that by just opening up a line.
Donald Miller
Yeah.
Kyle Reed
And you go, oh, my. Like it jumped you. You, you know, you, you get knocked off where you're thinking and then you go down the path. It's kind of the wildness. Like you don't know. You don't what to expect.
Donald Miller
Yeah. And that's what I mean by feral.
Kyle Reed
Yeah.
Donald Miller
There's something interesting about something that you can't control. There's also something I think that we admire about somebody that you can't control. Like, you're not going to. We just went and saw the. The documentary, the movie on Bob Dylan. I've seen it twice in the theaters now, and we'll probably see it a third time. Not because it's such a great movie, but it's actually worth studying both as a movie and as a personality. Also Scorsese's documentary no Direction Home about Bob Dylan, but there was something about Bob Dylan That I summarized recently in an Instagram post. What made Bob Dylan famous is the quality of his work. He wrote songs that can't be ignored. They can't be ignored. You cannot ignore. You can't ignore Blowing in the Wind. You can't ignore like a Rolling stone. Quality, quantity, 60 plus albums, 44, I think studio albums, I mean, just ridiculous and constant. His tour is called the Never Ending Tour because it started and it's never finished. And then third was, his attitude was, you will not control me. I will stand up here on this stage and deliver this, this concert with an electric band while you boo me and call me Judas. And the fact that he think about, he did that. He did that in his European tour. He did that at Newport Folk Festival. They were booing him, they were throwing things at him because they wanted Blowing in the Wind acoustic. And he gets up there and he's copying the Kinks, you know. And that is now arguably the greatest album ever. Most widely respected album ever is the one that was being booed. And it's almost like comedians in some ways go first they go out there and they go, I'm gonna say something that is gonna be charged. It's going to be probably a little bit offensive to you. It's gonna be taboo. And you get to watch somebody jump off the high dive into a 2 inch baby pool of water.
Kyle Reed
Yeah.
Donald Miller
And there's something just like, this dude's crazy. He's gonna. That's crazy that he's gonna say that.
Kyle Reed
But they change culture. I mean, you know.
Donald Miller
Well, they do change culture. Yeah. It gets to why probably they're important or not important, I don't know. Or, you know, they're either good for us or bad for us. I think they're probably a little bit of both.
Kyle Reed
I think they're good for us, though, because it's almost like you need that person in the room who will say the thing that everybody's afraid to say and go first to your point.
Donald Miller
Yeah.
Kyle Reed
And take the risk.
Donald Miller
Well, that's reason number two on my list is they say what they think is somehow admirable. They say what we think is the second reason that I think they're. They say what we think, but we're just not willing to say.
Kyle Reed
Yeah. Are we afraid to say?
Donald Miller
We're afraid to say.
Kyle Reed
Yeah. And they say it in a way that we probably couldn't articulate, you know, as well. Yeah. One of the things I would add to that is they. One of the reasons I found was I think comedy works because they, they understand culture. And what I mean by that is if you think about a comedian, there's all kinds of different people walking in to the room that they have to make laugh. And so, you know, a couple episodes ago we talked about thought leaders and one of the things is you mentioned in the episode, you talk about tribes. Like we like to affirm bias our thoughts and we gravitate to a thought leader that basically, you know, but a comedian doesn't always have that opportunity or ability to have a room of like minded people because there's all kinds of different, you know, people walking into the room and they have to be able to culturally commentate on something in an entertaining way that's broad. And I think comedians, and the reason why comedy works is because we kind of need that shared experience of people seeing this overarching absurdity that we're all thinking about that you're now telling us in a funny way it's a joint experience.
Donald Miller
I mean, even Nate Bragazzi, who's so clean, he's saying things about his relationship with his wife that you really shouldn't say publicly. You know what I mean? Like, he's saying, like he goes, you know, he goes, the other day we're flying to London, we're leaving Nashville, we're flying to London. And I say to my daughter, what time do you think it is in London? And she's like, okay, well it's 4:12 here, so it's, you know, 11:12 or whatever it is there. And he goes, what do you think? And she goes, 11.
Kyle Reed
And he's like, really?
Donald Miller
Why would you answer it that way? You know what we're doing, you know the game we're playing, she goes 11, my guess is 11. And it's like, why won't you answer like an actual normal person? Why do you have to be like that? And then of course they get in a fight for like the rest of their trip to London. Yeah, every one of us has had that moment. But you're not allowed to talk about it publicly. You're not, your wife is annoying you.
Kyle Reed
I remember the 12.
Donald Miller
We had a 12. My wife has a 12 year old baby sister, Gloria. And Gloria and I, Gloria is sitting next to me on the couch, we're watching this special. And she just goes, I can't believe he's saying this about his wife. I can't believe he's saying this about his wife. She's too young to know that that's actually why he's saying. Because he's saying something none of the rest of us are willing to say so reason number two for me is they say what we think.
Kyle Reed
Yeah. For me. So, you know, another point I came up with is, I don't know if you went down or thought about it this way, but there's something about life that's just. It's just hard. Like life is hard. It's not easy. You know, just. I was talking to a buddy last night and he. His daughter is a freshman in college. She comes back home from Christmas break for Christmas break, she's going back and he's like, I'm gonna take her out to a nice dinner before she goes back. It's like, good for you. And I could tell though, that's not where the story's going. And the story's going that they finish dinner, he gives his ticket to the valet to go get his car. And he's standing there for 20 minutes waiting. He's like, where's my car? And finally he's like, the guy comes back and he goes, hey, I can't get your car open. Like, your key's not working. It's a brand new car. And so they run off to go check. And he's like. And he cannot get his car open. And he's like telling me, he's like, I'm getting more frustrated and more frustrated and more frustrating. And he's like, the key will not work and he's breaking the key and he's like, you know, for like an hour. And basically the point was like, here I am trying to like do something sweet with my daughter and it turned into me like trying to hold it together, that I don't lose it in front of her and this 20 year old valet kid. And it's like, just reminded me of like, as sweet as you want life to be, there's still hard moments of life. And so it makes me think like with comedy, like, it kind of pulls you out of moments where it's like the everyday grind of life of like, ah, like just it's another day and you get the chance to kind of just go off to a place.
Donald Miller
There's something. I see what you're saying. There's something about commiserating on the miserableness of life that is somehow, you know, I don't know, it's comforting.
Kyle Reed
It is. And one of the things I love that comedians have been doing lately is they make you lock your phone up, you know, when you go into a show.
Donald Miller
Oh, I haven't had that experience.
Kyle Reed
Yeah, they don't let you bring you can't have your phone because they don't want you to film it and, but.
Donald Miller
It'S like it's their bit.
Kyle Reed
It just allows you to escape the noise and kind of like just for a couple hours, just be a human and laugh.
Donald Miller
Yeah.
Kyle Reed
And I don't know about you, but for me sometimes I just need that.
Donald Miller
There'S something therapeutic about it that commiserating about our miseries.
Narrator
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Donald Miller
Normally I don't have lists of the five or six reasons something works, but I just wanted to one up you today. I wanted you to feel like, inferior as we were sitting here because you clearly didn't make a list.
Kyle Reed
I mean, I could make you feel inferior and show you my list, but go ahead.
Donald Miller
I don't know why. I mean, just show me the list. Just tell the listeners your list. You alluded to this. Number one was they say what we think. Number two was they say what they think. They say what we think, they say it. Well, have you seen the documentary called Comedian with Jerry Seinfeld? I watch historical documentaries a lot, either about business or about history or about World War II or famous figures or whatever. Comedian is the best documentary I've ever seen.
Kyle Reed
Wow.
Donald Miller
It is about Jerry Seinfeld wrapping up the show, throwing away his material and starting over. So you watch a comedian, arguably the best, I mean, certainly top five of all time, right? Arguably the best ever. Start over. And it's not a comedy. It's literally watching a guy struggle and work and bomb on stage. He'd go in and he'd get five minutes anytime he could so he could test a joke and then that joke wouldn't work. So of course it doesn't go into the. And he works up 60 minutes. By the end of it, he's got 60 minutes of new material that he can actually take on the road. And, I mean, that dude worked his butt off at one point. He actually put the pieces of paper of jokes, like yellow tablet on a street in front of his house so you could physically see. And it was like 40 yards of individual yellow pieces of paper that he had written on to actually come up.
Kyle Reed
With this material just to get 60 Minutes.
Donald Miller
Yeah. And then even the timing of it, like, if you watch Theo or Nate or Nate Bragatzi is a great example. You try to deliver one of his jokes. Just try it. Try. Try to pretend you're him and deliver one of his jokes at dinner. And you can't do it because he has so perfected the timing of when he's gonna drop this line and when he's gonna drop this line and then when he's gonna drop this line. And I actually watched his special, his second special, and maybe his first special or his second special and his Saturday Night Live opening monologue, and I watched him give the same monologue, only it was different. It was different angles on the same stories. And then punch in this one line from the previous special, and you could see how his mind was evolving, where it was like, okay, I'm going to give this, but that one was so good, and nobody's probably heard that one, so I'm going to bring it in. Or what happened was he's delivering it, and he accidentally went into old material because he's so used to going from here to there. You could watch the mind actually work and how he did it. There's something about this sort of crystal clear having been worked on so many times, that he just knows it inside and out, and he can deliver it perfectly. It's like, we know Scott Hamilton, who's the Olympic skater, working on that routine over and over until it's just completely dialed in is what a comedian has done. And I think the third reason that we like comedians is they are presenting something that has been so freaking polished that you're actually, without knowing it, watching a master of their art deliver it so incredibly well. And, you know, Jeff Foxworthy is an old friend, and the amount of time that he would put into a routine was insane. And when he did Portland, when I lived there, I got to go, and we went backstage and met him and Larry the cable guy and all that kind of stuff. And then my friends are not hicks. This is Portland, Oregon. They're flaming liberals. Right? And they're sitting there and they're rolling. I mean, they're rolling. And they kind of went in rolling their eyes, going, Larry the Cable Guy and Jeff Foxworthy and Hick, and this is all Southern humor in Portland, Oregon. And he won them over in five minutes. And it's just the, it's how he has so carefully articulated every little cadence and every beat of this, I think, is one of the reasons that we, like, we would like it in, in a speech, you know, Winston Churchill speech or whatever. It's like that's dialed in, man. That is dialed in. And I think that's one of the reasons we like them.
Kyle Reed
Agreed. I. That was a big revelation for me in the last, you know, over time, as I've started to see, like, they make it look so effortless that it seems like they didn't practice any of it. And then when you come to find out, like I've heard Rogan talk about, this is just. He'll spend two to three hours just writing, Just writing. Every day, just writing.
Donald Miller
I didn't know that.
Kyle Reed
Every day, writing, writing.
Donald Miller
Jerry Seinfeld makes that point too. He said he was sitting at a cafe and he was taking the day off or taking the morning off, and he watched these guys cross the street with hard hats and lunch pails going to work on this building. And he said, oh, my word, if they have to work at their job every day, why am I not working at my job every day? And he developed a discipline, which is the number that's the main reason that he is so successful, is he had the discipline. He also sat in writing rooms and filmed 10 years worth of episodes of Seinfeld, which I think the reps get you there too. But he actually has the discipline. Some friends of mine, they like Seth Rogen and Jonah Hill and some of the pot smoking Pineapple Express sort of guys, they really admire those guys. And I'm like, why do you admire them? Well, they're like me, you know, and. And I, I said to them, probably lost the friendship. I don't know. Can't even remember who I said it to. But I said, you got to understand, they're not like you at all. They're pretending to be like you, but they're not like you at all. They do not sit around and smoke pot in their mother's basement. These guys work their butts off. They work their butts off and they have incredible discipline and incredible work ethic. And then you see them, the character that they have imagined up with all that hard work, that's what you're seeing. And you think that's them. It's not them.
Kyle Reed
And there's. Yeah, that's my. That's the thing. I walk away with just even thinking about this as a whole. It's like there's this mindset that you should just show up. At least for me. Show up, and it just should be perfect. And the truth is, the greats, the masters, in this instance, comedians, but also other people we admire, is. That is not true. That there is probably no one. I would go as far as say, no one who just shows up. They have put in the work.
Donald Miller
Not if you want to. Yeah. Not if you want to win.
Kyle Reed
One of the things, you know, Don, you're talking. It sounds to me. I'm just picking up on this. Comedians have actually, like, shaped a lot of the way that you think about things or have shaped some, you know, your life in, whether it be business or speaking or even relationships. I was just curious as you were talking, like, how has, like, comedians, comedy, like, shaped you as who you are today? As a business leader or a dad, a friend?
Donald Miller
Gosh, I don't know. I mean, you know, you watch anybody do something, you know, I walked out of Seinfeld not wanting to be a comedian, but wanting to be a better writer. You could smell the discipline. You could smell it. You could feel it. I mean, he's. I've never been in a room like that. He started out on a scale of 1 to 10. His opening jokes were 10. I mean, we were laughing. And by the time he. He was finished, about an hour and 10 minutes later, we were at 20.
Kyle Reed
Yeah. I mean, that's how I felt about Bill Burr.
Donald Miller
I was at painful, uncontrollable, like, stop it. You're hurting me.
Kyle Reed
Yes.
Donald Miller
And he was firing them off like fireworks going off. And one was building on the other and calling back to this. And I'm just like, never seen anything like that. And it made me want to go back and write better books. It's like, hey, dude, you need to go back and you need to do better at this. I remember I rewrote blue like jazz 54 times.
Kyle Reed
I didn't know that. Really?
Donald Miller
54 times. And there was a guy. There was a seminary professor down south somewhere. I used to know his name, and he was my biggest critic. He just hated me. Absolutely hated me. And, you know, the book was banned from Christian bookstores and, you know, very controversial at the time. I still don't know. I have no idea what the contra. I really don't. I'm not I have no idea what you guys were. It was just different.
Kyle Reed
They didn't like jazz.
Donald Miller
Yeah, they don't like jazz. And one of the things he said was, this is the easiest form of writing that there is. And finally, I just publicly wrote an open letter to him, and I said, do it. Do it. Like, literally, sit down, seminary professor, and actually try to write one page, much less 250 pages. That feels this easy and free. Just try it. And it shut him down. He never. He never opened his mouth again.
Kyle Reed
Yeah. And, like, what's the number one rule of going to a comedy show is try to heckle the comedian because you're gonna lose. And that's what. Yeah. Yeah. That's actually such an interesting point, Don. I didn't know that, because I think that's ultimately, like, the thing I'm. The bigger overarching thing is what I'm learning here is we love comedy because it's masterful. And what you brought up there is. You know, I remember that book coming out. It just seemed like you just were sitting in a coffee shop, just musing.
Donald Miller
I have a friend who recently read on the Road by Jack Kerouac and was just commenting about how amazing that he did that freeform, that he just. He never edited any of it. He just took out a piece of paper, and I'm like, do you really believe that? Like, yeah, that's what he said. That's what, you know. Yeah. Everybody knows that on the Road is. And I'm like, that's part of the act. That's part of the act. Supposedly. It took him, like, eight years to write that book. It's part. You gotta understand, this is part of the act. It's part of the fiction. Didn't stop there. He created a mythology around himself like Bob Dylan did. Like, half of the stuff isn't even true. Dylan's like, I grew up in a circus, and I learned to play from cowboys. He never was in a circus.
Kyle Reed
Great story, though.
Donald Miller
Great story. Dylan knew, like, oh, you think I'm done when I get off stage? I'm not. I'm always on stage. And Jack Kerouac was like that, too. I mean, I don't know what point that brings up, except for it is a performance. I'll get through the last two things. Because we've kind of already hit them. They give voice to our dark side. They say the things that we haven't even been able to articulate. We're kind of like, that's kind of true. Right. I don't want to Be the kind of person who thinks that, but it's contrary. They definitely give voice to our silly or our stupid side. I mean, the stuff that comedians are talking about is so, so silly. You know, it's just like, come on, you got to give me a break. They give voice to that, and then this is a big one. And it kind of has to go into just that presentation being so dialed in. They optimize for entertainment. And so where I'm optimizing, like, when I do a talk, I've given the storybrand talk 250 times. You know, I actually will give that talk now and realize while I'm giving the talk that I'm daydreaming and will go, oh, you're at this part of the talk now. And my mouth is still moving and the audience is laughing. But I've just given it so many times. I have optimized that talk. I know where every joke goes. I know where. And it's on autopilot. But imagine optimizing a talk only for laughs. Like, testing it. That didn't get a laugh. That's out. This did get a laugh. That's great. Oh, when I worded. Oh, when I do this action, it gets a bigger laugh. And optimizing it for only for laughter is fascinating.
Kyle Reed
Yeah.
Donald Miller
That's why John Aciff was so impressive, because he did it twice. He must have tested the material. I don't know how. And it was dialed in, man. It was dialed in. It was a laugh a minute, without question.
Kyle Reed
Yeah. I actually remember when he did that. Did you go, no, I didn't. But I remember him advertising and just being like, what a bold thing. I mean, that most people's greatest fear is, like, public speaking and then do comedy.
Donald Miller
Do you think comedians are addicted to the audience and laughter? Do you think that's part, like. Do you think an element of the need for affirmation and attention is part of what drives them?
Kyle Reed
I don't want to make it, like, blanket. This isn't a blanket statement. But a lot of the comedians I hear talk, and a lot of my education is through interviews. Like, Rogan's done with them is a lot of it is. There's something in their past that they were either trying to get attention for or coming from or making at a hard upbringing. You know, it's kind of like musicians. They talk about. This is like they. To get that success, there's so much drive because they're not successful. And then when they get successful, how do you follow up with, like, there's nothing funny about living in a mansion. Or there's, you know, there's nothing, there's nothing like romantic about that. But, but what's funny is like, struggling in this environment. And so I do think there's a degree of that of like, it's a high, it's a high of getting.
Donald Miller
I think it serves somebody who has that proclivity addiction, even to the audience, it serves their career. It's one of the, you know, I even said to a publisher recently, we were talking about publishing strategy and who you should publish and who you shouldn't, which books you should run with, which books you don't. We talked about the benefit of actually having one of your authors have a narcissistic personality disorder. It's like they're going to sell a lot more books because they're going to be out there on stages. They're going to be saying yes to every podcast where somebody who doesn't have that personality is going to be like, I think I just want to be home. Like, I miss my family because the addiction isn't driving them to leave home. You know, and it's fascinating to me, some of the public speakers who talk so much about family and how important it is. And I'm like, you spoke 250 times last year and you always talk about your family. And one of the reasons that I think you're talking about your family is one, you feel guilty because you don't actually see them and you're not invested in their lives at all because you have an addiction, you have a problem. You have to be in front of an audience. And two, you're covering your tracks. If I get up here and talk about how much I love my family, you won't realize that they don't even know who I am. And that's not to throw all comedians under the bus, but I'm just saying there is a need. I'm amazed. I was looking at some of these highest GROSSING Comedians of 20 Nate Bragatzis.
Kyle Reed
How much did he make?
Donald Miller
80 million.
Kyle Reed
That is mind boggling.
Donald Miller
1,098,000 tickets sold, right? Dave Chappelle, 44 million. But Nate did 163 shows. Now, I happen to believe Nate is actually an exceptional dad. He travels with his family.
Kyle Reed
She always introduces him.
Donald Miller
Yeah, he optimizes for family. Also where Nate is at right now, you got one. You got a shot, buddy.
Kyle Reed
100%.
Donald Miller
And you got to do it right now. So please don't say, but Dave Chappelle been around the block, man. He's been doing this for 25 years. 44.2 million on 30 shows.
Kyle Reed
30 shows?
Donald Miller
30 shows. Jerry Seinfeld, 43.7 million, 82 shows. By the way. He gets half a million per show is what I understood. What he does is he. He gets a private jet. They fly him there. That's the other thing that. Nate's in private jet territory now, so he's getting home. Yeah, that changes everything for a comedian. But what I understood back in the day, this was 10 years ago, you pay Jerry Seinfeld half a million, he has a specific order that he wants. He brings a few friends or family members with him, and he does two shows. So he flies out, does two shows, he's back by probably midnight. You know, back in New York, if he's doing any sort of east coast thing and he's waking up in his. In his. Putting on his slippers the next morning, having spent time with a good friend, eaten great food, and do two hours worth of comedies a million dollars richer. This is Gabriel Iglesias.
Kyle Reed
Yeah.
Donald Miller
111 shows, 40.6 million.
Kyle Reed
That's very impressive.
Donald Miller
And then. I've actually never heard of Matt Rife. Have you heard of Matt Rife?
Kyle Reed
Yeah, he's a.
Donald Miller
What's his stick?
Kyle Reed
So Matt Rife is. Does a ton of crowd work. He's very funny. He's younger, big online, big on TikTok, big on YouTube. He's. I would say he's been doing it a while, but he's really blown up. I'd say in the last three to.
Donald Miller
Four years, 35.4 million on 125 shows.
Kyle Reed
Yeah, he's crushing.
Donald Miller
Yeah.
Kyle Reed
He's young and single, though. He can travel.
Donald Miller
I mean, the profit on that thing. Well, I was going to say just some.
Kyle Reed
The best thing in the world if you want to start a business, is become a funny comedian. Because the overhead is incredible. Yeah. You know, the biggest thing I would walk away from just this conversation and this research on this is comedians have the ability to connect with humans. And when you do that, well, you can move people to do something. And so one of the things that I thought was interesting as I was. I was listening to some different things, is comedians can say, hey, I'm coming through your town on a Tuesday night at 8pm yeah. And I'm going to ask you to do the hardest thing, and that's put some pants on, get off the couch and drive down here. And you'll do it, but you won't do that for every comedian. You'll do it for the comedians that have invested the time in building community with you. So that's why some of these biggest pod or the biggest comedians.
Donald Miller
Biggest comedian of last year, I'd never heard of.
Kyle Reed
Yeah.
Donald Miller
And it's got some sort of community.
Kyle Reed
Because they've built a community. And I think you look at some of the people who, you know, are maybe on different shows or different sitcoms or SNR or whatever, I don't think they could sell an arena out. But the ones who do are the ones who have put in the work as far as building a podcast out, going on a ton of podcasts, putting in the community effort. And so then when they ask you to come hang out, you feel like it'd be like a law, a buddy who you haven't seen. You know, you have those friends from like college or your mid-20s who used to have so much fun laughing and hanging. It's like, let's get together again. And when they come through town and they ask me to go here, I'm gonna show up and I'm gonna tell my wife, my kids, like, hey, you know, I'm going out tonight to hang out with my buddy I haven't seen in 10 years. It feels like that. I think comedians have an amazing ability to do that only if they build that community.
Donald Miller
And we could go on a long time about different aspects of comedy. But I'm curious, listeners, who your favorite comedians right now. Why do you think comedy works? Why do you think comedians exist? It's definitely kind of a wonderful mystery that exists out in the world. Leave your thoughts in the comments. Kyle, great to talk to you today.
Kyle Reed
You too, Don.
Narrator
Thanks for listening. Listening to the why that Worked podcast presented by StoryBrand AI. If you like the show, follow wherever you get your podcasts. And if you're Enjoying this on YouTube, hit that subscribe button and leave a comment letting us know what you think and what you want the guys to talk about in a future episode. Curious about how StoryBrand AI can help you create clear, effective messaging? Well, you can try it out right now and create a free customized tagline for your business. Just go to storybrand AI. Thanks for listening and we'll see you next time.
Summary of "Why That Worked – Episode #7: Comedians—The Science and Strategy Behind the Funniest People on Earth"
Presented by StoryBrand.ai, hosted by Donald Miller and co-hosted by Kyle Reed
Release Date: February 17, 2025
In the seventh episode of "Why That Worked," hosts Donald Miller and Kyle Reed delve into the intricate world of comedy, exploring the science and strategies that make comedians some of the most influential and beloved figures in entertainment. Through a blend of personal anecdotes, analytical discussions, and insightful observations, the hosts unpack why comedy resonates so deeply with audiences and what sets successful comedians apart.
The episode begins with a contemplation of the seemingly odd phenomenon of people paying substantial amounts to watch comedians perform. Donald Miller opens the discussion by questioning the very existence of stand-up comedy, highlighting its unique place in the entertainment landscape.
Kyle Reed echoes this sentiment, sharing his skepticism about attending comedy shows in his hometown of Nashville, emphasizing the unconventional appeal of live comedy.
Donald Miller articulates several core reasons that underpin the effectiveness of comedy. These reasons not only explain why audiences flock to comedy shows but also shed light on the enduring success of comedians.
One of the primary reasons comedy resonates is that comedians express thoughts and feelings that audiences might hesitate to voice themselves.
This ability to verbalize the inarticulate creates a deep connection between the comedian and the audience, fostering a sense of shared understanding.
Authenticity is pivotal in comedy. Comedians who stay true to themselves and present their genuine perspectives tend to connect more profoundly with their audiences.
Kyle Reed emphasizes that this authenticity allows comedians to infuse their performances with real, relatable content that hits "you in your gut."
Donald introduces the concept of comedians having a "feral" aspect—an untamed, unpredictable quality that keeps audiences engaged and intrigued.
This unpredictability mirrors the wildness of human nature, making comedians fascinating figures who can disrupt the mundane flow of everyday life.
Comedians often serve as cultural commentators, using humor to critique and reflect societal norms and issues. This role not only entertains but also provokes thought and discussion.
Through their performances, comedians can influence public opinion and contribute to cultural shifts, underscoring their significance beyond mere entertainment.
A recurring theme in the episode is the immense discipline and relentless work ethic that successful comedians embody. Both hosts share personal stories that highlight the dedication required to master the craft of comedy.
Donald Miller shares his admiration for Jerry Seinfeld’s disciplined approach to writing, noting his daily commitment to crafting new material.
Kyle Reed adds that the seemingly effortless delivery of top comedians masks countless hours of preparation and refinement.
The precision in timing and delivery is crucial in comedy. Donald highlights how comedians like Theo Vaughn and Jeff Foxworthy meticulously hone their routines to ensure maximum impact.
This meticulous preparation ensures that every joke lands perfectly, enhancing the overall comedic experience.
Successful comedians excel at building strong connections with their audiences. This relationship is cultivated through consistent engagement, community building, and delivering relatable content.
By fostering a sense of camaraderie and trust, comedians create loyal fanbases who eagerly attend their shows, much like reconnecting with old friends.
Beyond entertainment, comedy serves as a therapeutic escape for many. It offers relief from the stresses and challenges of daily life, allowing audiences to momentarily disconnect and find joy in shared laughter.
This therapeutic aspect underscores the essential role that comedy plays in enhancing mental well-being and fostering a sense of community.
The episode also sheds light on the financial success and professional dynamics within the comedy industry. Donald and Kyle discuss the impressive earnings of top comedians, attributing their success to the combination of disciplined craft and strong audience connections.
This discussion highlights the lucrative potential of comedy when combined with relentless dedication and strategic community building.
Comedians hold significant sway in shaping cultural narratives and societal perceptions. Through humor, they challenge conventions, address taboo subjects, and introduce new perspectives, contributing to broader cultural discourse.
This role as cultural shapers emphasizes the profound impact that comedians can have on society, extending their influence far beyond mere entertainment.
Episode #7 of "Why That Worked" offers a comprehensive exploration of the art and science of comedy. Through insightful discussions and personal anecdotes, Donald Miller and Kyle Reed illuminate the multifaceted reasons behind the success of comedians. From their ability to articulate unspoken thoughts and maintain authenticity to their rigorous discipline and profound cultural influence, comedians embody a unique blend of creativity and strategic prowess. This episode not only celebrates the craft of comedy but also provides valuable lessons on effective communication, audience engagement, and the impact of genuine self-expression.
For listeners seeking to understand the mechanics of successful communication and the power of authentic messaging, this episode serves as a compelling examination of why comedy works and how its principles can be applied to various facets of business and personal growth.