Caleb Hearon + Caitie Delaney | How to Be Funny, Employed, and Only Mildly Traumatized About It

28:48Can we go back to that? Yeah, yeah, yeah. No, ignore what I said. What did you think of me? No, not insecurity, but I definitely feel one of the things I love about working with Katie and anyone at this point that I choose to collaborate with, there's no one I'm collaborating with by choice that I'm not like, I care what they think of me. That is the only rooms I'm interested in being in at this point. Yeah. I don't want to be with, I don't want to, and if it's like someone who, like I said, if it's like a veteran of whatever space that they've directed 200 episodes of some hit TV show, if I don't think they're cool and funny, I don't give a fuck what they think.

29:17Yeah. So I'm like, I don't care because I don't need your approval. I have my fans approval. I have my friends approval. I have money in my bank account. So I don't care what, you know, John Doe veteran thinks of my stuff. You had your time. I'm glad. I'm so glad. There are some of those people that I deeply respect. Yep. And I'm interested in what they have to say, but I don't care the way I care about Katie because Katie's my buddy. And I'm so, like, I so admire your brain that I don't know if it's insecurity, but I'm definitely like, if I pitch something and Katie doesn't laugh, I'm a little like, oh, gotta do better on the next one.

29:50Yeah. Like I want it, you know? Yeah. Is there something about, whether it's your collaboration specifically or just like comedy collaboration in general that is like really important that the average fan of comedy or someone who's, wants to be a right comedy. Is there some part of collaboration that like you guys, like a really subtle thing that people don't really think about that is actually really important? I don't know if it's subtle. It's probably pretty obvious, but I feel like it's worth mentioning. Like it's just such a joy to write for someone that you know and you can sort of assume their voice.

30:31And we had a character in our show that we wrote together that's basically Caleb. His name is Calvin. Very different. Yeah, we're pretty creative. And we had some concept art made and the character looked like Caleb. It was Caleb, you know, with an edge. I mean, certainly there was a character there. It wasn't one for one. But knowing Caleb as a friend made it so much more fun and easy to write his character in that. And certainly the type of writer I am and what I think I would say to people who are aspiring to write is... Hey friends, Olivia from Oli. Between new routines and the ultimate group project known as parenting, you need science-backed solutions that work with your life.

31:17That's where Oli comes in. Start your mornings off right with Maltese made to support nutrition and immune health. Choose from our lineup of gut-supporting probiotics and we've got occasional sleep support to help the whole fam chase their big dreams. Head back to class with the number one gummy supplement brand. Stuck up on ollie.com today. These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure, or prevent any disease. I always need to see myself in a script that I'm writing. Like, I'm never going to write like Dunkirk, you know, because I wasn't there.

31:48And like, I don't really have any insight on like what those guys were doing. I wasn't Kirk in the Dunn. Absolutely not. I don't even know what, you know. I don't know what happens there. I have to envision myself in often the lead character. Like so many things that I've written, you're like, oh, that's Katie. Like I imagine myself in a situation that I write it. And maybe that's lazy, but I just I think I know that that's how I get the best writing. Not even like I'm a particularly like original or interesting type of person. It just makes it very authentic when I know like this is exactly how I would react to this situation that I'm writing here.

32:23so to sort of do the same thing for Caleb as a friend yeah uh just made it feel so rich and real I think there's two things that come to mind that I was actually thinking about earlier when when um when Katie was talking about um I know this isn't the idea but I know we don't want it to be like this but in writer's rooms particularly or in collaborations in comedy writing there are common turns of phrase that serve specific purposes learn them and use them that's what I would tell people There are all these little phrases in writer's rooms that are so helpful that are like, this is the bad pitch.

32:55Or this is kind of a house numbers pitch. I've never heard that one. House numbers? Yeah. We use that all the time on Big Mouth. What is it? House numbers is like, but this is the other thing, is rooms will have their own specific cultures. They'll pick up their own inside joke that becomes the lingo. Because it's like Mark and Jen who are show running, they worked on a show where it was used. Right, where they used that. So it's like they only trigger. house numbers is like, like this, this is like a house number pitch where it's like the number of the house isn't specific, but you're on the block.

33:24You know what I mean? Where it's like, this is like in the 900 block of Santa Monica or whatever. You're like, I haven't dialed in on the house, but I'm pitching. It's like general area. It's ballpark. Or it'd be like, I know this is like, this is like shoe leathery. Like there's different things that serve as like that dialogue is sweaty. You know what I mean? It's like, it's trying too hard. Have you heard of my favorite one is Refrigerator Logic? Refrigerator Logic. Refrigerator Logic comes from, I know it from the sitcom world, working on that sitcom. Refrigerator Logic is when you write something for the plot of your show that doesn't quite make sense.

33:58And then when the audience during the commercial, when like the person watching the show goes to the fridge to like get another beer, they realize, well, that doesn't make sense that that just happened. Refrigerator Logic is like you have to smooth it out because the audience is going to realize, you know, thinking about it for a few seconds that it doesn't make sense. than it was for the show universe. I also think like so many of these turns of phrases are really just about like, hey, I'm about to say something that I'm not 100 % sold on, but I think it can help us get us there. It's all that, really.

34:29All the time I'll see, because I do it all. I say this isn't it, but at least seven times a session. And I write like eight songs a week. So that happens like so many times. And I'll see other co-writers who maybe they're just nervous in general or they're nervous because they're writing with a hit maker or whatever and they'll start and they go, no, no, no, no, that's not it. And I'm like, no, no. But you have to say it. Do the whole thing. Because what if it just like inspires a different rhyme that just gets us somewhere because it's better than just sitting here saying nothing. And if it's not it, get it out of you because whatever is it is in there somewhere and it's in a traffic jam behind the things that aren't it.

35:08So get it out. Get it out. But the reason you don't want to get it out is because you're scared you'll look stupid. Right. Look stupid. We're all fucking stupid. Look stupid in front of us. Get rid of that. We're making jokes and songs and trying to get people to pay us for them. That is crazy. We're stupid. I can't imagine a worse thing to say in a writer's room than, this is it, I've got it. Like, if someone says that, it's like, ew. We would be like, boom, shut the fuck up. To have that amount of confidence that what you're saying is the exact right thing, that is embarrassing. That is stupid.

35:37Actually, I've never thought of it the opposite way. That is so – because I'd be like, no, don't use a disclaimer. Have confidence. Like, no, you would sound crazy. Also, I will say when we've clearly found it, move on. There are some junior writers that I've been around in rooms that I'm like, we'll be pitching for a minute. Everyone's doing their – and oftentimes in like Big Mouth World, we would pitch in the character's actual voice. So we would do like the voice that Maya Rudolph does or whatever. And so you're pitching it to hear what it would sound like because it's animated. We would pitch for a while.

36:05Maybe it would be like four or five pitches in. Someone would pitch a killer. It would bring the house down. Everyone laughs, yeah. Everyone laughs. And you're looking at the showrunner and it's clearly like it's going in the notes. We got it. And then some junior writer would be like, but. Or it's ketchup. And we'd be like, what the fuck are you doing? It's like you killed the momentum. That's a moment where it's like feel free to read the room and reign it in. I'm not saying look stupid at all costs. I'm saying look stupid when the job is to look stupid. Once we've got it, I would say save yourself and move on.

36:35I think that's amazing. that's like that's advice that i'm gonna use like today that's like really good advice well the other thing i think and i wonder if you guys will relate to this is like the idea that i learned in my first writer's room was like just get in where you fit in and like don't worry about being good try to get better at the things you're bad at but i'm a very i believe in like natural tendencies i got into a first writer's room and i quickly realized i'm not really a third act structure guy and i'm really a season arc narrative guy. What I am is a really fucking good joke writer.

37:04And so I was just like, okay, I'm going to leave that to the guys that have been doing this for 20 years that are here to write structure and season arcs. And when it's time to write jokes, I'm going to lock the fuck in. That is what changed my life as a songwriter. When I went, okay, I'm a really fucking good lyricist and I'm really good at editing other people's melodies. Sometimes randomly I'll stumble on an amazing melody, but it's rare. So instead of like sitting here trying to like, while I'm in collaboration, try to like learn to be a better melody writer and like step on someone else's amazing melody.

37:40Why don't I just keep focusing on the lyrics and edit their melodies? But that took me until I was like 34, which is when I finally made a dollar because I realized like, oh, I don't have to be good at everything. That's why I'm co-writing. And for you to know that so young is awesome. And I'm sure you've experienced that. But like now that once you accept that and do an actual inventory of your real skills and make peace with it, you can work from it. And so now I bet when you're looking at collaborators in a room, you're like, I would love someone who's great at melody. Oh, I'm always like, I need a woman under 25 who writes the best melodies ever.

38:18And it's not that I'm an ageist. It's just that they've been listening to a different generation of music that I have. I can cover any, I can cover lesbians from the 90s. I know all their songs. I don't need help with that. I need someone that has listened to a whole other generation of music that I have no interest in studying. It's like, but I didn't learn that until later. So it's like if you can cheat code yourself and learn, hey, focus on my strengths and find different collaborators, that's a great cheat code. It takes time, certainly. I think it's, I'm still sort of in a place where I'm not quite, well, I think I didn't realize what I was good at until I was told enough times.

38:53I'm told that I'm a really good joke writer and truly there's nothing I fucking hate more than Joker. I hate it. I mean, you take a script home and you just have to come up, every line just come up with a funnier version of it. Like, I don't know. It sounds stupid that I'm saying I hate that. That's like a perfectly fun thing to do. I imagine it sounds great. But I really, I struggle with it. And I always assumed I was more of like a structure, narrative, character. I think character is probably the thing that I'm most interested in developing. And not to say I'm bad at it, but I've had to accept over the last couple of years, especially, I get a lot of joke writing jobs.

39:33I'm like, why the fuck are you hiring me? I hate it. But I guess I'm good at it. So there is an acceptance that I had to go through. But I think that that's also really helpful information, too, of like, I always say to young writers, like, hey, because they'll like a writer signed to me like, I'll be like, oh, my God, the song that you did yesterday, like your manager just sent it to me. oh my fucking god you killed it you have to write with that person over and over again i didn't really like the vibe i'm like are you trying to date or are you trying to make art do you know what i mean like yeah so it's an i think it's a thing of like well you just said like joke writing might be your least favorite part of the job but you're really good at it so i think sometimes like the word job is there for a reason totally you know yeah it's can you guys remember early on something that you did, whether it was a joke on Twitter, just because you mentioned that's where you met, or a stand-up thing or in a writer's room, something early on that was like clearly a fail, but you were like, but it changed the way that you work.

40:39Like, I can remember many fails, but I can think of a couple fails that actually like helped me move forward. I've got ten off the top of my head. Go for it. I don't think I've failed. I've heard it's helpful I'd like to someday I'm just too good I remember all the time actually I think about it constantly because I got when I first I had been doing stand up for a very little amount of time I had like mostly been focused on improv and sketch I was living in Chicago I was getting into stand up and I was doing I was doing like PowerPoints with my stand up because I was so insecure and PowerPoint can be a very funny tool to use in stand up I was personally using it out of insecurity then I was like I told myself like I'm done with the PowerPoints I'm going to do stand-up, and if I fail, I fail, and I'm just going to, like, try.

41:21And I got booked. My first headlining gig was, like,$30 to headline the attic at Hamburger Mary's in Chicago. Fierce. Fierce. And it was, like, of course, a bunch of gay comics. And the whole, I was so fucking nervous the whole week leading up to it because I was supposed to do 10 minutes, which now I can't do less than 10 minutes if I try. Yeah. When someone tells me to do 10 minutes, I'm like, that's a setup. Like, I can't. But when you're starting out, you're like, 10 minutes? How would I ever find the time? And I was so nervous all week. and this comic that I am very, very dear friends with now, she's opened for me on the road many times.

41:53Her name's Carly Kane. Shout out Carly, I love you. She was on the show and she was a much better comic than I was. In some ways she still is. I would say her joke writing is superior to mine. And I was so nervous to be on a show with her and she was like maybe middling on the show. And she was also a headliner, but I just happened to get the headlining spot this night. And I was really nervous. It was a queer show. And I went up and I had written that week. I was like, oh, I'll write a bunch of like self-deprecating stuff, which is such an odd move for me because I love myself. I'm like, it doesn't make any sense.

42:24And it was not particularly funny. And I don't know what inspired, I guess I was just like, oh, the audience will like that. They'll feel, they'll get it. Maybe I was watching something that was very self-deprecating at the time. Who knows? But I did a very self-deprecating set that was of course not authentic and not funny. Bombed harder than I've ever bombed in my life. Bombed harder than when I was starting. Like I bombed, I to this day have not bombed the way I bombed on that show. Wow. I bombed. And also, by the way, oh, I think maybe it was a strip comedy show. And the producers were like, when you get a big laugh, you're supposed to take off clothes.

42:56What? Well, guess what? I've seen one of these. I left the stage fully clothed. H.R. Nightmare. There wasn't a moment to take off a shirt. Like, I was like ready to take off a shirt, but I was just waiting for that laugh. It never came. So many layers. Everyone else getting off the stage naked. I almost put on clothes while I was on stage. Like, I somehow got more clothes. Give me your shirt. Gloves. Truly. Like, people were throwing clothes to me, You'd be like, put it on, slump. Yeah. So I bombed so hard. I get off stage, fully clothed. Everyone else is in, like, nipple tassels and panties. I get off stage, and I'll never forget.

43:26I was at the back of the room, and it was, like, I was in the bar. And so the show's still going on. And this, like, 65-year-old dyke, like, cool as hell, like, short gray flat top, denim vest. Hot. Hot, cool, older lesbian. She sounds hot. She was hot and cool, and she had, like, this gravelly voice. and she comes up and she hits me on the back and she goes, I bet you're funny, but next time, do better and get naked. It walked away. And I truly was just like, I'm going to go home and kill myself. Like I was so humiliated because she was right. I did bad and I was clothed. Both facts, both facts.

44:03Both facts. And I just remember I was like, I will never again do a set. I will never again do a set that inauthentic. and I will not write. I wrote the whole week being like, I wrote with the intention of killing. I wasn't trying to say anything honest. I wasn't trying to be loose. I was like, I'm gonna do a tight set that kills. And that's not how I kill. And I just remember, I was like, never again will I do that shit. And I've never bombed as hard as I did that. It was horrible. How far into doing standup was that? I mean, I had a weird journey with standup because I was so intimidated by it.

44:34It's the scariest of the comedic performance styles. I cannot imagine. And so I did it when I was like 18 and then I stopped for a couple of years. I had done it. I was doing it on a, my first standup gig, my first comedy gigs were at a burlesque show in Springfield, Missouri. My friend Casey ran a burlesque show and she was like, hey, we need someone to host. We'll give you 20 bucks a night. And I was like, great. And I did the worst standup you've ever seen in your life. And then these girls came up and got naked all night long. And so it was like obviously the objectively cooler thing to watch.

44:58And so then I took a break. And so maybe at this point I had been trying at standup for like eight months, like going up every night, every night for eight months. and I bombed. And you just made a hard turn and started making completely different jokes than your usual stuff. I was like, I'm going to, yeah, I'm going to like, I'm going to try and say stuff that actually matters and stop trying to kill. And I'm going to say things that I actually feel are going on with me after that, yeah. Instead of trying to guess what the audience wants from me. Yeah. And turning that, it took the power back from the audience and gave it to me.

45:27Yeah. And I was like, I don't care. If I'm going to bomb, I'm at least going to bomb saying something I care about. Yeah. And it worked. Yeah. Which is great. That I think is so, important and helpful because it's like the the in my early days of writing for other people i thought the way to win was like well i'm gonna go in and just try to write the whole song and show them like i really didn't even need your help and of course then they hate me like justin sucks i just like wrote the whole song and then the song wasn't as good because i didn't ask for their help but it was like i was trying to like really kill right like my version of like I'm going to go and I'm going to write this set to kill.

46:06I'm going to go and write this song to just show how great I am not to write a great song. Yeah. And it's like what a fucking dumb. There's some huge pop star who like didn't even talk and I thought she was going to like that. You know how stars are. Stars love being ignored. Yeah, they love to take a little time off from attention. Is there a way that it usually works with you where like people come in with like half-baked ideas or like you have something to listen to that then you build off? Or are you expected to start like from the beginning? I would say normally it's always starting from scratch.

46:38Of course, there are moments with collaborators that we're close with and we have a vibe. Yeah. And they go, hey, I really love this. Just happened last week. I love this chorus and pre-chorus, but the verses suck. And I've tried to write it 10 times. Can you help me? Yeah. But I would say 95 % we walk in and start from scratch every day. but now I've learned to like it's about their life so I have to let them lead the way and I'm just there to make them the best version of themselves if I try to like make this about me why would they ever come to me can you remember a moment of like pure failure that actually pushed you thank you because I saw the sidestep Justin that's so interesting about your career nice try when did you fail Katie we want failure there have certainly been many times where I realized I wasn't as skilled at something as I wanted to be.

47:33I think pitching is a big thing for me, but something they don't tell you when you're becoming a TV writer and you want to do that as your job is that like 50 % of the job is being like charming and in front of a group and selling your idea to them, which I had no idea that that was part of it. I don't think I'm much of a salesman or a performer. Um, I would much prefer to just write my entire thing and send the document to someone and let it speak for itself. But that's like not what you do, especially now pitching is changing so much. Companies are so networks are so reluctant to buy something and like give it a chance without knowing entirely what the ideas and what the first five seasons are that you're expected to bring all that to the table and really sell it.

48:20Yeah. And starting pitching was rocky for me. Really? I actually think pitching with you really leveled me up in a way that I've carried forward with me. Caleb is so funny. I mean, yeah, you're funny. I'm not going to lie to you. I'm good at pitching. I'm good at pitching. I know that's right. You really have this way of, because the other thing about pitching is executives are on pitch after pitch after pitch, day after day. Yeah. Sometimes you're like the sixth, seventh pitch that they've heard in a day. And now they're all on Zoom. So it's like you're looking at their Zoom boxes and some of them are just like on their phone.

48:58There are people who like get up and walk away and you just see that they're like not at their chair. It's crazy. Do I stop? Do I wait for you to pee? It is horrible. It's torture. And Caleb is really good at just sort of like breaking through that and like getting people engaged and having a bit of fun, like something really silly that you do. I hope you still do it when you're just like on Zooms, is you would change your display name. So instead of like Caleb Heron, it says like Katie's number one fan. It's like an inside joke that has come up very early in the pitch. You like recognize when something funny happened and then you change your display name to reflect something funny that we said.

49:37And then people slowly notice it. It's just so like brilliant. It has to be a show. Yeah. You have to perform a show for them or they won't buy from you. I have on pitches, I'll change my name to like guy you're about to buy a show from. Or if someone's texting, I'll be like, sorry, I'm just going to stop for a second. John's missing out on the pitch of a lifetime right now by texting. And then they'll come back. And then his coworkers laugh at him. Yeah, exactly right. But it's like you have to like put on a show for these people and you have to remind them that you're in charge. Because they're so used to being in charge.

50:05You have to be like, actually, right now you're listening to me. Because if not, they're thinking about 12 other things. And I understand. I'm not mad at it. It doesn't hurt my feelings. I'm like, I know you have emails to respond to, but right now I'm pitching something I've worked on for months. Let's fucking do this. It can be intimidating if you don't be like, no, fucking listen to me. And it helps break it up for us. Like we pitched our show 10 times at least. And it can really become like a rehearsed thing where we have to get through a lot of material in like 20 minutes of people's time.

50:31And it can really start to feel flat. And I would get very nervous about like making sure I was hitting everything and that people are hearing it. And so for you to break it up with little things like that, just meant like, oh yeah, like we're having fun here. We're doing this. We're telling people our idea. So yeah, I was not great at it to begin with. How do you think, do you think the best way to get good at it is to like, by watching other people who are good at it? Yeah. You just got to keep doing it. And I think similar to what we were talking about with like financial security or like once you've been doing it long enough, you just have to keep doing it and realize like.

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51:46It's a hard thing to do. Everyone knows it. So just be playful with it. Yeah. It also is kind of like dating in that way, I feel like, where it's like desperate cloying please love me energy will lose. Even if you have the best, you can have the best idea, the best script, something that they would buy from someone else. They won't buy it from you if your energy is like, please, sir, can I work? It's like relax, have some confidence, fake it if you have to. And like just fucking like, yeah, have an energy of like, it's like you either want this or you don't. Yeah. And if you have to at least find a way to convince yourself that it's like, if you don't buy this, I'm going to sell it in 20 minutes to someone else.

52:23Yeah. So miss out if you want to. Yeah. But you have to have, you don't say that unless you can be, unless you can really pull it off. I was going to say, we did kind of do that. I was going to say, we can pull it off though. I wouldn't tell a younger writer to be like, buy this or miss out. We had slides at the end of our pitch where we collected a bunch of tweets from just people who followed us like, when's Caleb going to get his own show? And like people talking on Twitter about how funny we are like, Katie, this is the funniest thing I've ever heard. We just put those up like, well, the tweets speak for themselves.

52:54Like you just have to be goofy about it. Yeah. The reason why I kept asking more follow-up questions on it is that for me, because I wasn't a band for so long, when people say, do you miss performing? I'm like, well, no, I perform every day. Sure, it's only to a room of three or four people, but I'm putting on a show. And stakes are high. The stakes are high, and I'm putting on a fucking show. So the reason I kept pushing is because people who, any sort of creative collaboration, there is an element of putting on a show, whether it's to a huge fucking audience like you, or whether it's to just three people in a room.

53:30So that's why I think it's another lesson of either find a collaborator who's really good at putting on the show while you're learning to get good at that too. Because there's so many examples of things that none of us are good at everything. And how do we fill in those gaps when we need to? Because also really as an artist, when you're asking somebody for money of any kind, you're not asking them, at least in my opinion, you're not asking them to believe in the project as much as you're asking them to believe in you. yep they it's like even as a painter it's like the painting can be beautiful but they need to believe that you're going to go on to sell many many many paintings and this is going to be a worthwhile investment or it's not whether or not the tv show is going to get a ton of views it's whether or not you're going to be the kind of person who goes on to do 10 other successful things afterwards so the tv show continues to go back and get the belief is in you yep and so unfortunately i don't think it's a fair world it unfortunately is not enough to write a great script.

54:21You have to convince them to believe in you. That you can do the whole fucking thing. Yeah. And if the work is great but they don't believe in you whether they know that's what's happening or not psychologically they won't work with you. Yeah. And so you have to figure that out. Yeah. And you're very good at it by the way. You don't give yourself enough credit. Oh my god thanks. I was just gonna say there are so many people, we won't name them, who do not deserve what they have, who are good at that. I can name a few. Let's go. I'll name them. Who are we thinking? Yeah give me some hints. Like unfunny ladder climbers who are just good at that, who convince people with the money that they're a blast to work with, that they're collaborative, that they have longevity.

55:02Yeah. And sometimes it's true and they just make subpar material, I think. But everyone had a good time. And it works for them because they are just so much fun to have in real life. Like there are those people that it's like, I want to go have dinner with that guy. Yeah. And those are the people that succeed. Yeah. So I'll buy the show because I want to have dinner with them. Yeah. It's cool. I want to have dinner with them. There's like a very small percentage of people that get to be true, pure artists and get to win. And by win, I mean have financial security and make a bunch of awesome things that they want to make.

55:30There are much more people that are great operators that are not great artists that win. So my pitch to younger artists would be play the odds. Play the odds and focus for at least a little while on being a great operator. And in the background, hopefully you're also being a great artist. but if you want to make stuff, you're going to have to figure out how to operate in rooms and you have to decide what that looks like for you. I certainly could be a better operator. I'm lucky that I think sometimes my distance from the operation serves me. People think it's cool but that's a tough game to play.

56:03You know what I mean? Do you guys remember when you were young that like I always say like what ruined my life? Like when I heard a certain song and I was like, oh fuck, I'm a musician now and this is going to be awful because trying to make money in art. Is there a song? There's two very clear moments. One is Debbie Gibson. When I heard someone, I was a huge Debbie Gibson fan. I was like a five, six-year-old homosexual and I was a fan but I heard someone on the radio say that she wrote and produced all the songs herself and she was like 16 and that was the first time it really like hit me. Oh, someone's making the songs.

56:41not just singing them someone's making them and then later Ani DeFranco lesbian folk artist from the 90s her when I was introduced to her music it was like oh I'm definitely not going to make theater I have to write songs do you guys can you remember a joke a stand-up special a tv show that was like oh fuck I'm doomed now this is my life well for me I think it was a bit later on I've always been the type to not really know what I'm up to or what I want. I did not. What I'm up to is really funny. What am I up to? Yeah, that's pretty much me all the time. I've heard that before. I don't know what I'm up to.

57:24That's really good. I did not like major in writing in college or anything like that. I majored in anthropology and that was only because my like advisor took me aside my junior year of college, like you must pick a major or you're not going to graduate in time. So I liked anthropology and it was fun, but I really didn't know I wanted to be a TV writer until I saw a TV writing room, the Tim Allen room. And I was like, Oh, I can do that. Um, I think previous to that, I certainly liked watching movies and TV and stuff. I think, uh, the lonely Island era of SNL was kind of huge for me where I was like, Oh, this could be fun.

58:06And the music part of it too, I'm, you know, I really enjoy music and I've thought about trying to, you know, be involved in it in some way. And just the way that they were able to combine their music skills and comedy was really inspiring to me. And I thought, I remember I applied 2007, I was in college and they were huge, like 07, 08, 09. and I applied to be an NBC page for when I got out of college because I was like really wanted to work on SNL and like be around the magic. Yeah. And I'm very glad that I didn't at this point from everything I've just heard about. That culture. I mean, it's, yeah, yeah.

58:45It seems like pretty hellish. Slightly south of magic, I would say. Slightly south of magic. You really got to want it to be in that machine. Yeah. But that's probably around when I realized like, all right people write this and it's funny and maybe i could do that yeah but yeah it was it was into my adulthood that i really latched on yeah i think that's fucking awesome though because like i think so many people who are in college and aren't exactly sure what they're gonna do think like oh well fuck if i didn't want if i didn't start writing jokes at 12 i'm never gonna work on rick and morty you know what i mean like it's i think that that's i mean don't get me started on college, which it is nuts that kids go straight from high school to college with no time in between.

59:27It's a miracle that any 17, 18 year old has a good idea of what they want to be when they grow up and they spend a hundred thousand dollars to that end. I feel like people shouldn't go to college until they're like 25 years old. Yeah. That's nuts. I'm one of the rare ones that I'm like, yeah, my dad literally like ruined his credit to put me through college but my degree was in songwriting and now he's retired good because of me so like he what's one of the rare occurrences like i should have gone to college when i did and even though it ruined his credit for 20 years i i made it all back yeah yeah do you remember what made you go oh fuck i'm gonna be a comedian now it's so funny because it's not like i was thinking mine i was like it's no fun but like i just grew up in a really small town in missouri and we were so broke that like our art it never occurred to me that i could be an artist like no one was an artist.

1:00:16Like everyone was a nurse or a teacher or a farmer. Everyone was poor. There were two guys that had any money within like a hundred mile radius of my town that I knew of. One was a banker and I was no good with numbers and one was a lawyer. And so I was like, and I knew that lawyers talked a little bit at work and I was like, I'm good at talking. I've always known that. Like I'm, I can talk to anybody. You would be a very good lawyer. I, well, yeah, I'd hire you. 16 year old me agrees. So I, I went to college and I was like studying pre-law and I was studying sociopolitical communication no way yeah i thought i was gonna be a lawyer and then i got so fucking depressed in college and suicidal a shout out and shout out sophomore year who else um that girl that girl something yeah i woke up one day sophomore year and i was like being alive has been fun what if it was over quick pitch hey i'm gonna be good at pitching this isn't the answer this isn't it but like killing ourselves yeah um and then i was quickly like it might be it um and your friends like no listen you gotta say it get it out get the good idea get the bad idea out thank god you were in a writer's room at the time yeah yeah yeah i took it to the room i was like i'm thinking about killing myself you guys they're all also suicidal not this but killing myself it's not killing myself but like something like that um i get driving really fast without my seatbelt Hold on, I have something, you know?

1:01:35House numbers pitch. House numbers pitch. House numbers pitch. Suicide. I don't have to be alive anymore is the idea that we're trying to get to. Something in the suicidal arc. Yeah, yeah, yeah. And your job as my collaborator is to elevate my suicidal thoughts. We workshop my suicide note. No, it's heavy on top. It's too detail heavy. That's more pro, yeah. It's really sad. But I. The jokes are too soft. Yeah. But no, I was so depressed. and of course all my friends were theater kids. Like that's who I gravitated towards. And I had a bunch of friends that did improv and I was like, that seems like the most humiliating thing you could possibly do to yourself but I am gonna kill myself soon so I have nothing to lose.

1:02:15Wow. And so I was like, well if I'm already gonna kill myself I may as well do improv on the way out. And so...

1:02:24Reach the depths of hell. Is that what everyone takes before they take an improv class? Most, yeah. And then, you know. And so I did, yeah. I started doing improv and then I had this will to live that I was like, oh my God, this is so much fun. I should do this forever. And that was the first, I didn't ever think I'd make any money out of it. Yeah. I was like, oh, I'll move to Chicago. And then if, you know, if it doesn't go well, I'll go to law school in my 30s. I'll spend my 20s like fucking around in Chicago. If it doesn't go well, I'll go to law school. But this has like ignited my will to live.

1:02:48And then I started doing comedy and then, wow. Yeah, when did you realize that you could make money doing it? I would say like, honestly, a year into being in Chicago, I realized that I was very good at it. Yeah. I was like, actually, I've seen so many other people do this and I feel like I'm actually quite good at it. But I also knew a bunch of people in Chicago that were very good at it that had never made a dime off of it, that were in their 40s and 50s, had been doing improv forever and had never made a dime. And I was like, okay, so you can be very good at it and make no money. Yeah. And so I was like, maybe that still isn't the path.

1:03:18But I had committed – I moved to Chicago when I was 22 and I had committed my 20s in my brain. I was like, you get to spend your 20s fucking around. If you don't make money by the time you're 30, you'll go do something else. Yeah. And, yeah, that was the plan. I mean, suicidal thoughts being your inspiration to become a comedian is way better than Debbie Gibson. Also, tale is old this time. Tale is old. Every comedian ever. It's like truly such a sick field of work to go into. With both of you doing so many awesome things, do you feel like your relationship to ambition has changed at all? This episode is brought to you by State Farm.

1:04:00listening to this podcast instead of doom scrolling smart move another smart move getting help from one of state farm's 19 000 local agents when you choose to bundle home and auto bundling just another way to save with the personal price plan prices are based on rating plans that vary by state coverage options are selected by the customer availability amount of discounts and savings and eligibility vary by state Yes, like entirely. I don't know. I think it's the world. Tell me more. It's the world changing in the way our industry is changing sort of at the same time where I am now content to have a job doing what I do kind of well for somebody.

1:04:44Yeah. I definitely still have ambition to make my own art and to work with people that I really love. But I mean, it really used to be Oscar winner, best picture, best original screenplay like that. And it's still to some like, yeah, that would be sick. But it's not I don't really think it's necessarily in the cards for me. I don't know. I just don't think about things that way anymore. And I think it's just like, when's the last Oscars that we're going to have? Not to get like super dark, but it's like we might be done with Oscars at some point, just the way the world the world is going. And since we had our writer's strike in 2022, three, three, a few years ago, we haven't really recovered in the industry since then.

1:05:31And jobs are so hard to come by. I'm just so grateful to have work at all. I'm working right now, which is like a miracle. And oh, my God, thank you. Employment. We love when she works. And my ambition is to just like hang out with my friends and have a nice time. Yeah. I, it probably sounds sadder than it is. I'm actually so happy to like make my life a little bit smaller. Yeah. And just allow myself to let go of those like very lofty ambitions. Because I think even if you ask people who have like one best original screenplay at the Oscars, they probably wouldn't note it as like the most significant moment of their life or something that changed the way they are fundamentally or like made their life worth it.

1:06:12It's just like something that happens on one night that's on TV and then you go back to your life. Right. And a lot of times those things that we all dream of is because that's all we could have, we saw at the time. When you want to be in the business, all you can see are those crazy public moments. So of course those become the dream. But then once you're in there, I think I'm the same. Just like you said, like, you know, for songwriters, it's so hard to win Grammys. We're only eligible in two categories. We're like, if you're an engineer, you're eligible in like 60. So I, when I was young, of course that was the dream.

1:06:44But now that I know the nuts and bolts of it, I'm like, well, that's probably not going to happen for me. And like, who really cares? To like get paid to make things that people like is really awesome. But the public things, of course, the public things are what we all dreamed of originally because that's all we saw. But there just aren't enough, the same way with jobs right now, there aren't enough jobs for all the people who are really, really good at it. when you realize it has nothing to do with the quality of your work or your own talent and that there just aren't enough Grammys to go around and it actually doesn't mean anything about you as a person being able to let that go is like pretty huge how do you how do you feel like it just has your because also as some like you're the face of your art it's like the ambition in some ways kind of has it can't really diminish or does it or do you feel I would say when I was like first starting out my ambition was to like be a star and I had a lot to prove to myself I think I had a lot of things to learn about loving myself I don't think in my early 20s I loved myself very much at all I thought I did um and I do love myself so deeply now um and I'm like proud of myself and I like who I am and I think my ambition now is to like see how much money I can give away and how well I can pay people and how good I can be how good of a person I can be inside of this like extremely fucked up industry that I work in and how much trouble I can cause for the people in charge and how like bad I can make their lives until they decide to do good things.

1:08:13I want to make them uncomfortable. That's a huge ambition of mine. I want them to be scared of working with me because I might speak up too much about something they don't want to talk about. And yeah, my ambitions are to spend more time with my family, to have fun, to like to say no to money when it means that I'll get more free time to spend with people I love. My ambition is like how, how like ethically and well can I do this? How much time can I spend with people I like? How much time can I be in rooms with people like you that I'm like, I love these people. I admire them. I like their work.

1:08:43They make great stuff. They're nice. Like I want to, yes, my ambition still is to like pay for my mom's house and live comfortably. I don't, I would not like to be poor again if I have the option, but my ambition mostly is like, I don't give a fuck about winning an award. I've been nominated for a few. I haven't gone to the ceremony. I would really like to keep that up. You're here with Woody Allen. I'm exactly like Woody Allen. I'm exactly like Woody Allen. I'm so glad you said that. I would do nothing different. Finally the interview gets to Woody Allen. That's what I brought you here for. I'm exactly like Woody Allen.

1:09:18My daughter's here. Come in, come in. We're very close, to say the least. That's horrible. Keep it in, but that's horrible. Actually turn it up a little bit Make that the loudest part You know what's so funny You talk to older actresses In this business And you get one drink in them And they'll start telling you How much they love Woody Allen Yeah It's really funny It really didn't get through to that You'll be like I do not agree Or want to hear that And they'll be like I love him He did nothing wrong It's insanity Any actress over 60 Is like Cheers to Woody It's like Oh my god Pour one out for Woody Genuinely And it's any of them unprompted you'll be talking about like the weather and they'll be like you know what that reminds me of how woody allen's innocent um you're like no like we literally we literally know he's not he's not he literally like hey so he's not every day it's here yeah allegedly allegedly allegedly for my lawyers allegedly allegedly but yeah i think my ambition is just to like see how much fun i can have see how much i can disrupt this like really insidious cultural force weighing down on all of us that tells us that more is good.

1:10:27Consumption is good. More is good. Having nicer things. Spending more money. It's not to say I don't want to have nice trips and own a home that I'm proud of and comfortable living in. I'm not like some kind of like saint. Yeah. But I would like to, as much as I can, push back against this like thing that weighs down on all of us and tells us that the only thing to want is more. Yeah. I hate that. And I think it's making people sick. And I want to try and find a way to exist in all of this that isn't that. while also getting rich people to give me money to make my art because I like my art. Yeah.

1:10:57You know? Yeah, I feel like for me, it's like there's still lots of ambition left in me, but it's about like I want to like do like I have songs that matter like in a new generation. Like that's the new one of like it doesn't have to be like the biggest and the best and I don't need to win every crazy award. And just like you said, if it happens, cool. I'm not going to – I will show up. I will show up. Yeah, same. One thing about me, I'll turn a look. Yeah, Justin. Justin will turn a look on that carpet. Any excuse for more makeup, I'm going. But it is just like this new thing the last couple years of like, okay, like I've done this for a decade.

1:11:35Like, could I get another decade? And it's definitely not about the money. That has been awesome and it's so nice to not be broke. But it really is like, can I get like, what if I like became one of the few that like had hits for 20 years, not just like five? Like that's the new one of it. Can I just keep going? It's like, and the younger me who was so desperate to be famous, to like get revenge on all of my bullies in the suburbs of Chicago. The younger me was like, I must be the most famous person alive. And now it's like, can I just like keep making songs? Like every couple of years, there's a song that people really like again.

1:12:10And it's like, nice to feel that I'm still ambitious, but the ambition has for sure changed. And it must be, I'm sure that you've had many collaborations and just meetings with very famous people and probably realizing that that's not something you want to aspire to, that being famous is not all it's cracked up to be. It's a wild thing to want as our friend is on the way to being one of the most famous people alive. Justin, please. That is so horrifying. It is a lot to contend with. Oh, you hang out these people in the landmass beneath their feet has shrunk and shrunk and shrunk until it's just enough for them to stand on their tippy toes.

1:12:47And it is so horrifying to watch. And especially the famous people who are really lovely, who are genuinely wonderful. And you're like, oh, fuck, like you've been famous for so long. Some of them got famous as kids and it wasn't even really there. They weren't. They just like doing theater and their parents put them on TV. And oh, fuck. Yeah. And it's like it is. It's like I like an endless. like can I just please hug you because you're just no matter how lovely you are you're like forced to this weird loneliness I've never heard someone describe it as the landmass that's like exactly what it is this I have been saying for a while and it'll be interesting to see how I feel about it in a couple of years but I have come to view fame as a process of isolation that the land beneath you just shrinks and shrinks and shrinks and people can't fit on it with you yep and so you just become smaller and smaller and smaller until you don't go to the grocery store You don't walk down the street alone.

1:13:38You don't feel comfortable going to dinner alone. You can't get on public planes. You can do nothing that makes life beautiful, which is existing in the world anonymously. You can do nothing that makes life beautiful ever again. And it's horrifying. And I feel so bad for people that have experienced that level of fame. And I'm really desperate to, I felt, I loved like eight months ago. Eight months ago in my life was like a perfect moment where I was like, let's ride this forever. You know what I mean? eight months ago I was like what was about it eight months ago was awesome I mean it's already changed but eight months ago was a perfect level of money and fame for me I was like if I go somewhere that there are lesbians I if I want to take some pictures tonight I'll go find the lesbians you know what I mean if I want to take some photographs I'll go to Chapel Rhone's concert you know what I mean and if I want to be left alone I know like the places I can go and it yeah but it has changed for sure and I yeah I the thing you're talking about of meeting someone who is mega, mega, mega famous, like big, beyond A-list, like huge, huge global star, all I do is feel sad for them.

1:14:38Yeah. And when they're lovely, I feel more sad for them because I'm like, God, you deserve some peace and you just, I don't know how you would possibly find it. Yeah. You do, I mean, it makes me think of Marie Antoinette who like built her own like French village on the property at Versailles so that she could go like cosplay as like a peasant woman. I did not know this. Yes. It's still there. You can visit it. Iconic. It's like a little Disneyland kind of French village of that era. Her Disneyland was to be a peasant. Yes. That was her version. And all of the servants had to go play the roles with her.

1:15:12That's what our famous people are also doing now, by the way. Right. That's what I'm saying. That's what these ranches are. Where they're like, yeah, I just want to get back to basics. It's like if I touch that cow, it would fall over. It's like a hollow paper. You know what I mean? I'm glad that the two people that Katie has. Katie's like, you remind me of two people. Woody Allen and Marie Antoinette. Two of our best. When I think of Caleb, I think Marie, Woody. Yeah. Woody Antoinette. Woody Antoinette. No, it is like, it is, because I don't sing the songs, right? My version of experiencing that is like having a publishing company and a label of realizing that like, I like, if we're like looking at somebody to sign to the company, and for whatever reason, it just doesn't make sense.

1:15:58it's this like oh fuck I they had the meeting with me they thought maybe I could make their dreams come true and now if I I'm saying no I just I crushed their dream for today right and they have to go start their dream over and my I mentioned her a lot on this because she's such a mentor of mine but Wendy Goldstein who runs Republic Records like you know one of the few women that the music business actually listens to icon genius and she said to me like hey when you're going to go from just a songwriter to a publisher and the label, people are going to hate you now. You have to accept that people are going to hate you.

1:16:34And it's like, as someone like you who's on the journey to getting more famous because your art for better or worse makes you famous because you're in front of the camera. You have to accept like, Oh fuck for like my dreams to come true. Now, like random people are going to hate me. And that's so weird. And do you know what I tell myself every time I start to get stressed out about that? What? My grandpa worked on the railroad every day. of his life you know what I mean you really have to just like have some perspective of like yeah I think you'll be okay if you get bothered in the grocery store yeah it's not ideal but it like certainly beats like 99.9 percent of lives that have been lived in the history of the world yeah so yeah it's a little spooky to me and I don't fully understand it I'm like I don't really understand why this is happening but if it were to go that way I think I would be okay well no and that actually just helped me put it in perspective of like oh yeah for every time I have to like crush somebody's dreams and let them down and know that they hate me and we might have mutual friends and now it's going to be awkward because i didn't sign them or whatever the fuck it is i do get to make so many other people's dreams do come true yeah and so instead of stressing about like someone who now is going to talk shit about me at that party at least someone else did get the deal also relish it maybe you're playing an even more important part of their right now they're gonna be motivated you get to play the villain in their story You're the person they're going to go win a Grammy about.

1:17:53And maybe they'll talk shit about me on stage. I swear to say, fuck Justin Chanter. And thank you, God, and my family. Good night. And I'm like, yes! I'm in the front row crying like you tell them. You tell that. Bag it. Okay, so to wrap it up, we do like a quick little rapid fire game called gag or drag. If you love this thing, it's a gag. If you hate it, it's a drag. Or it's just like, meh. Right? Like, I don't want to talk about this. Why did you ask me this? I hate you, Justin. That's fine too. Easy, yeah. Okay, writing jokes specifically to go, for both of you to answer, but you can start, writing jokes specifically with the hope of them going viral.

1:18:33Drag. Drag. Yeah. Yeah, easy. I think anything that I've done that's ended up going viral on Twitter, again, like a million years ago, is something that I thought was really stupid that would get 10 likes and then, yeah. Yeah, the things that go the most, when you're in that part of the career where you're trying to make anything to get attention, you do it and then it gets attention you go that was the worst thing i made that month and it would just drive you crazy drag okay plain dumb gag drag you hate playing dumb i think i love playing dumb i like to play at least twice a day like in what in what context um like uh whenever i'm like in like a business setting with straight men which is almost all my business settings yeah i'm just like i don't know like this crazy idea like i probably am wrong You guys know way more about this than I do.

1:19:19I will say, actually, I end up being the dumb one in a lot of writer's rooms that I'm in. Rick and Morty being an example. And then I've ended up on a lot of animated shows since then. I'm the one who has never seen a sci-fi movie like a Star Trek or like. So I'm like, I'm the one who has to be like, explain that to me. I don't know what the fuck you're talking about. So actually, maybe I change my answer. It's a gag to be stupid. I like playing dumb. I think it's so fun, especially when I'm intentionally breaking the rules. Yeah. When I'm breaking a rule that I know I'm breaking and then a figure of authority comes to talk to me about it, I love to go.

1:19:50Like I'm thinking about any time I've gotten pulled over by a cop. And they're like, did you know you were going 80? And I go, cars can go that fast? What? Yeah. Oh, my God. Officer, first of all, thank you for what you do. And second of all, oh, my God, I didn't. I'm going to get my thing checked. I say more fun to the police. Yeah, yeah, yeah, yeah. I love your blue life. And I didn't know I was going 80. Yeah, playing dumb is so fun. Okay, you kind of already answered this because the next one was actually being dumb. Oh, yeah, mine is actually being dumb. And that actually helps the collaborative process because someone has to explain it.

1:20:26I love being a moron. Gag or drag? I want it to be gag because I think that's the chicest answer, but unfortunately it's a drag for me. I hate being dumb. You're just too smart. Okay, gag or drag lesbians? Gag. Gag. Love them. Whoa. What if I gag? As a straight woman? It just depends. It just depends. Here's what I will say. Lesbians, my majority of lesbians are very handy. And when they're handy, I find them to be a total gag. When I come across a lesbian that wears Carhartt and can't help me with a shelf, what? Take off the jacket or learn the Ikea manual. Something needs to give. That would be my one caveat.

1:21:03Okay, I love it. Gag or drag gay men? Gag. Drag. Whoa! But that's you. By and large, I thought you loved yourself. I love me, but not that part. No, I love that part. I just think when we all get together, I'm thinking of gay men when they're together. Do you know how many gay guy friend groups there are where they all look the same, wear the same Speedos, and there's not a woman in sight? Why? Except for on their phones when they're worshiping her. Drag, drag, drag, drag. Get the fuck out of here. If there's not a they, them, or a she, her in the mix, you boys need some help. What if you were a straight man?

1:21:34I am. Oh. You didn't know? I am. This is all for money, baby. it's in right now but I'm about to do a big about face imagine your girlfriend reveal oh my god I mean who is it who is it who is it really actually it would have to be Holmes yeah yeah we would be so good at it our lavender marriage would be so special yeah that's really sweet I love that yeah I love that gag or drag notes that start with what if you just that's a drag yeah that sounds too prescriptive. Love that. I love giving a proper answer for that. That's lovely. Gag or drag queer people playing straight characters? Queer people playing straight?

1:22:20Gag! Gag! Gag! Get in there. And I don't care if the faggy little voice sticks around either. I don't care. We can suspend disbelief. It's fake. We like musicals. If we can believe that they're singing, we can believe that he's straight. He's straight and he sounds like that. Next question. Maybe he has a speech impediment, you ableist. Yeah, we've all done. Gag or drag, saying it's not that deep when it is. Drag. Drag. It's that deep if I say it is. We're past that. Turn a phrase. If I say it's deep, it's deep. You fucking better believe me. And everything is deep. Get over it. Everything is that deep.

1:22:57I'm like opposite now. Everything's deep. Get over it. Everything's deep. Gag or drag, the pressure to always be likable. Drag. Gag. gag because i'm like just do it just be like oh my god just get a grip why are you being more likable just do it that's funny gag or drag calling something problematic instead of saying you just didn't like it capture your favorite summer feeling with pandora jewelry discover a collection inspired by the sunshine freedom and moments that make the season unforgettable From sun-kissed metals to personalized pieces, ready to be engraved with your summer mantra. Each design moves with you, from beach days to golden nights and every memory in between.

1:23:45Shop Pandora Jewelry's new summer collection in-store or online at pandora.net and let your summer unfold. Kind of gag, actually. Don't you think kind of gag? It's a huge gag. What I love about problematic is I don't call things problematic because I have critical thinking skills. But I love that problematic has become a way for the dumb person to exercise superiority over a dislike. Right. I think that's actually kind of chic. Yeah. And the dumb community gets so little. And decide that's how it is with zero gray area nuance. Yeah, they can't technically call it like misogynist or homophobic.

1:24:20So they go, it's problematic. Because they don't know those words. Yeah. I like problematic as like the dumb person's way to participate. Yeah, I love that. That's a really joyful way to look at it.

1:24:33Gag or drag? Straight comedians discovering they can't say anything anymore. Gag. Gag. Oh, gag. I like it. More. More of that. I do. I do kind of actually like it. No, it's hilarious. At this point, it's so funny. You weren't saying anything to begin with. Right. So it is kind of a gag, actually. It's a Bill Maher gag. Gag. Mar or drag? Mar or nar? Mar or nar? Okay, when we revisit this collaboration conversation in 10 years, it'll be Mar-Nar. I love it. Okay, last one. I think it's the last one. Let me make sure. Yes, it is. Okay, last one. Gag or drag saying both sides about human rights? I'm going to go drag.

1:25:18I'm going to go drag. One or the both sides. I was waiting for you to say, I'm going to go drag. I'm going to go drag despite wanting to go gag just to see if I can find it on the way down. No, I mean, you could definitely pull it off. Just do it right now. Oh, okay, so both sides, gag. What would it be? Gag? Gag, both sides about human rights. Gag, no, it does just have to be drag. Anything I'm thinking of saying is like, it crosses into territory I can't get away with. Totally. You know? Some people don't deserve them. That's the answer. That's what it is. Yeah, yeah, fair. That's the other side.

1:25:52Okay, so full circle moments here. what would you tell this is not gag or drag but what would you tell your earlier selves about working together so if you could have given yourself like a cheat code about this collaboration was there like a piece of advice you would have given yourselves I just saw something really stupid do it do it this is the thing that Caleb hates the most out of anything that I do so I would tell myself never to do this one thing sure oh god I hate sure I cannot say the word sure to Caleb sure is like a dagger to the chest. Yeah, I agree with you. Shure is devastating. I've never really been of this persuasion.

1:26:31I thought Shure is a very like neutral, just like even positive, Shure. He'll be like, you know, see you at the place at seven. Yeah, Shure is thumbs up in a text. Every time I write Shure in a text to Caleb, he's like, oh, so I'll just go kill myself then. I'm not kidding. He hates it. I was flirting with a guy on Grindr the other day and he had said he wanted to hook up that night and so I messaged him. I said, hey, do you still want to come over? He said, sure. I said, say yes or I'm canceling. Yeah. Sure. Sure. I also don't accept sure during sex. If I say, do you want to do this? And they go, sure.

1:27:01Pardon? Well, that's nuts. That's what everything is. Everything is that. But not everything is during sex. It is if you're with me. Every interaction is sexual. You're right. Sure. I think that is a great note. If you never used sure with me, we would be in such a positive place. I forget too because I do, I say that word very often and I forget that Caleb really hates it. And then it happened just the other day and I was like, why is he saying that? Because you said something like, well I'll just fuck off and like not speak to you as a joke I asked her to read some writing of mine that I'm being very sensitive about right now I'm not sharing it with anybody she's the only person I'm showing it to and you said sure and she said sure oops she said sure and I text back and I said we don't have to do this if you don't want to and then I it took me a second I was like oh shit I said the bad word and then we had a call and I was like I'm so sorry sure sounds like a favor yes right whether it's can you read this sure do you want to do this thing sexually sure it sounds like they're doing you a favor and if it's about art or sex, I don't want favors.

1:27:57I want enthusiastic consent in every aspect of my life. Of course. 100. To coffee, to reading, to drinks, to sex, all of it. Enthusiasm. A cheat code to working with Katie. It's gonna, it sounds like such a cop out. The first thing that comes to my head is just that you're so genuinely easy and delightful to work with. I'm like, it couldn't have been better for me, but a cheat code to working with Katie. Or if you can't think of one for Katie. Yeah. Anyone watch, a cheat code to collaboration in general. Because, I mean, obviously she's just the best collaborator ever, so you didn't need any advice.

1:28:29No, there's nothing you have to learn. No, but really, there's nothing to learn about Kate. She's just like so, like does what needs to be done, turns things in on time, like can't think of someone better to work with. Do you love a deadline? I love a deadline. I need it. I don't get anything done. And by the way, something we didn't touch on at all, but it's so important about collaboration is I need it for the deadlines. Like if Caleb is waiting for me to write a scene, I have to do it. If I'm doing something on my own, that script is never getting written. Same. I need people to tell me when they need something or it does not exist.

1:28:56Anyways. Cheat code to collaboration, I would say, is something that Katie and I definitely do have as well is grace. Just like grace. Have grace. Like don't be so insistent. Like if you ever were to miss a deadline or you ever were to like respond in a way that I wouldn't respond in a meeting kind of on behalf of both of us or something, which you don't. But if Katie ever were to do those things, I would 100 % just chalk it up to like we're having a bad day, we're having a weird moment. I think sometimes when you collaborate with people and they take things so personally and seriously and like intense.

1:29:26I'm like, have some grace. We're human beings. This is also not, we are not at war. We don't work on the railroad. We are not nurses and doctors. We're playing make-believe. And so I think unless it's an egregious over and over and over kind of behavior, just let things be. It's okay. People can fuck up a little bit, you know? Yeah. Is there one thing, because we talked about on accident, which was wonderful, a lot about like making art for work, right? For executives, for this and that, for this and that. So just to sort of like wrap it up, do you guys have any advice to like aspiring people of like, yes, what we're doing is hopefully companies pay for it and they buy it.

1:30:05And that's in a lot of ways the goal, right? Because that's the only way to survive while doing it. Is there anything that like you feel like up and coming artists should protect as they like start to embark on like, okay, now my art is turning into business. And sort of as I was touching on before, I think if everyone can accept that they have a particular point of view and that anything that you write will be unique because you've written it is really important to remember, which is why I've just like really decided on writing from my own perspective and sticking with that. and it turns out that that's like original enough to be compelling.

1:30:44I would say everyone should do that and just start from you, think about your experiences of life, your particular, you know, shades that you have on and go with that. Yeah. I think what I would say is search within yourself and every time you're having a big meeting or something like that, you're about to send out writing or something, get very, very clear with yourself first, no matter how long it takes before you take it to other people and then help them to support you. So what I mean by that is like when I send something to my team to read or to look over or whatever, I send an idea to them, I will often tell them what I'm accepting in response.

1:31:18Like I will say I don't want to hear a word about producibility. I don't want to hear about market mandates. I don't want to hear about whether or not HBO or Netflix would like it. I am accepting did you think this was funny. I am accepting did you understand the vision. I'm accepting did you hate this character in a way where you would watch it. I am accepting a number of things. But telling people what you don't want back sometimes can be the most helpful. There are times you'll send things out and you're accepting everything. But I think get really clear about what you do and don't want to hear.

1:31:45And that's not to say that you won't need to hear those things eventually. I always eventually open it up to all ideas. But sometimes it is nice to go into a thing, and it's not even about what notes you'll hear. Sometimes it's nice to go into a thing and go, hey, I'm pretty loose on whether or not this piece of work is going to be set in this place. I'm loose on the B story. I'm loose on this character's arc and whether or not these people get together. I'm really firm on it being about his journey through X. Just telling people like this. That is awesome. Do you know what I mean? Awesome. Being like this is what I think the heart of it is.

1:32:16I'm feeling very protective of that. These things I'm willing to part with. What do you think? That is a huge skill. I'm starting that today. It's helpful. That's really awesome. It's helped me a lot. And it's something I've gotten better. I don't really do that. That's huge. It's really helpful. Well, people think you can't because they think it's anti-collaborative. It's not anti-collaborative. Eventually you have to open it up. That's part of it. You can't do this in isolation. I am saying eventually you have to open up to everything. But what it does is it helps you get to the next step in a way that feels safe to you because your work is precious.

1:32:46Yeah. And it is special. And you shouldn't be like, I'll never part with this joke. But you should be like, hey, right now I don't want to hear about what the market demands of my work. Right now I want to hear do you care about this character and his story. Yeah. You know what I mean? No, I'm going to literally start using that today because I'm executive producing this album. and there's like a pretty young A &R on the project. And he keeps just getting like the initial demos and he moves right to like detailed production notes. And I'm like, what the fuck are you doing? And so instead of me just hating him, I should say to him, hey, right now we're just listening to like super bird's eye view the song.

1:33:29There's no need to talk about production notes until we all decide we like the song. but I'm not telling him that. So he's just going right to the thing that he wants to talk about, which is like the geeky production because that's what he's into. And you can also make it about you, which is a very helpful thing with executive notes, like what you're saying, where it's like for my brain, for what I need right now, like do me a favor and only give me notes on this particular thing because this is what I'm thinking about right now so that they don't feel, you know, put out or like reprimanded. That's a huge cheat code in general.

1:33:57It's not saying like, you need to stop what you're doing. It's going like, it would really help me a lot. It makes me like, I kind of have a deficiency. I'm such a dumbass. I'm not able to work in the way that you are, and I feel so stupid about it. Maybe you could do me a favor. Yeah. You know, it helps. That's fucking awesome. So yeah, playing dumb once again. Playing dumb. And that's, I just have to say, that's just finding success as a woman. Totally. It's like, we already know, but everyone's gonna be like, you're a bitch if you don't say it that way. What about jokes? I got my period today, So I'm not really in my right mind.

1:34:35Yeah, totally. Yeah, that was amazing. Thank you both so much. Oh my God, thank you. Thank you. Hello, hello, everyone's favorite part of every podcast where we say please follow and subscribe to this podcast wherever you listen so you don't miss future conversations. And also, pretty please take a cute little second to rate the show. It's one of the biggest ways you can support us. See you next Wednesday.