The Dan Le Batard Show with Stugotz - South Beach Sessions - Jon Lovett

Episode Date: May 1, 2025

Jon Lovett has had a wild ride – from being plucked to write speeches for some of the largest figures in the Democratic Party (yes, like Hillary Clinton and Barack Obama)... to creating a television... show… to starting the bastion of “resistance” media in “Pod Save America” and Crooked Media. Jon takes Dan through his career, from his uncertain start through the many challenges (and joys) today of running your own company. Jon also opens up about his insecurities, his anxious energy, and how he uses those to his advantage. For more of Jon and Crooked Media, go to Crooked.com and watch, listen and subscribe to “Pod Save America” and “Lovett or Leave it”. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Starting point is 00:00:48 Visit CanadaLife.com slash business protection to learn more. Canada Life, insurance, investments, advice. Hello and welcome to the West Coast edition of South Beach Sessions. John Lovett is a media mogul. I can call you that, yes, if you're uncomfortable. He doesn't want that. Crooked media, Pod Save America, Love It or Leave It. Did you struggle with the name of Love It or Leave It?
Starting point is 00:01:30 Like did you wrestle it? As a former stand-up comic, is that a great name or? I think it's, we went through a bunch. We had other options, but we kept coming back to it. I was a little nervous about having my name in the name of the show, but especially in early 2017, it just felt right. It works for the time.
Starting point is 00:01:49 How did all of this happen? And when I asked this question, I say, you were going to do standup comedy. You were going to do math. You were a math nerd. So take me through how this happens because among the many things I'd like to do with you today is I'd like to learn a little bit about how to run a media company because I'm a bit of a novice. Maybe we'll find out together. But the I so I grew up in New York I went to Williams College, a small liberal arts college. I studied math, I studied psychology and philosophy. I loved
Starting point is 00:02:20 doing math. With math, you can't fake it and you can't almost get it. You either get it or you don't. And I found that it really, I am, you know, I will talk my way out of things. I will try to talk my way into, charm my way out of not knowing something. And you can't do that in math,
Starting point is 00:02:47 you have to really understand it. And if that logic and rigor really forces you to use your mind and concentrate, and I found it made me smarter, and it made me a more critical and precise thinker. And I really like that, but I was never, I was always the math student who could give the funniest presentation, but I was never at the level
Starting point is 00:03:15 of some of those other kids that went on to become professors. I hate math and most of the people in my sphere tend to hate math because these are different disciplines. You've chosen something much less precise. I really hate, I hate that everyone says they hate math and I don't blame the people who say it because I believe you, I understand why. I'm just not good at it.
Starting point is 00:03:36 But see, none of that, there's something fundamentally wrong, this is a conversation for another day, but there's something fundamentally wrong with a society as a society. We take kids, they spend more than a decade learning this subject and most of them get to the end of it saying, I don't like this. I am not good at this. So is everybody wrong? It's the most common thing you ever hear. If you tell people you studied math, they go, oh, I hate math, I'm not good at math.
Starting point is 00:04:07 So every school is getting it wrong. Like every kid in every classroom in front of every teacher, they're all getting it wrong. They're all, like, so something is totally out of whack. It would be, you know, I think it would be a better society if everyone got to the end of high school and maybe they learned less math, but they enjoyed it. They got something out of it.
Starting point is 00:04:30 They came away with some basic skills. I really didn't mean to upset you. No, but it speaks to something important about where we're at right now. Because it's one of those, I don't know anything about baseball. I'm jumping around. I don't know anything about baseball. I'm jumping around. I don't know anything about baseball,
Starting point is 00:04:48 but I know what baseball bats look like. We all know what baseball bats look like. And then some guy working for the Yankees stares at baseball bats for a year and he says, I think baseball bats are wrong. I think the little chunky bit should be a little bit further down. And they hit a bunch of home runs.
Starting point is 00:05:01 Basketball, you can do this with basketball. They were taking the most inefficient, least valuable shot near the rim and then they all figured out, wait a minute, we're doing it. Three points is worth more than two. Right, and we have this system where most people come out of math,
Starting point is 00:05:17 they won't retain anything. Could you do an algebra equation right now if I put it in front of you? Can I have some trouble? And yet, and people are kind of innumerate in the most important skills that they should have as an adult. The skills that you need to understand investing,
Starting point is 00:05:34 taxes, loans, credit cards. Come away with none of those skills, yet kids spend years sitting in front of teachers, watching, looking at graphs and algebra and all the rest. Imagine a math curriculum. It would be easy. Make it fucking easy. Make it fun and easy.
Starting point is 00:05:51 Whatever you were gonna do for three years, whatever you're gonna do, take the first chunk of it, spread it out, spread it out till everyone gets it. And then everyone comes away like, oh, I loved math, it was so much fun. What a better world that would be. How did we get here? And I don't mean, I mean all of it. And then everyone comes away like, oh, I loved math. It was so much fun. What a better world that would be. How did we get here? I mean all of it.
Starting point is 00:06:09 I don't mean not just conversationally. I mean you went from math, you had stand-up comedy to something that isn't those things. So when I graduated from college, I moved to New York. I was a tenth paralegal working for those asbestos law firms that you see advertised in the subway. And then at night I was either doing my law school applications or I was going to open mics. I also was interested in politics. I volunteered for the Kerry campaign in 2004.
Starting point is 00:06:37 I really liked that. I was actually enrolled in law school. I was doing the open mics. I was working in politics. And it was basically luck that, I was working in politics, and it was basically luck that a job turned up in politics. And I took that job in politics and ended up deciding not to go to law school. The dreaming of being what though at that point?
Starting point is 00:06:54 Are you still searching? Dabbling in several things you like. So I think the truth is, I would have answered this question differently, but the further away I get from it, the more it's clear to me that I really didn't have any kind of conception of what I wanted. I was just deeply insecure and I was looking for a way to get the validation or the bigness to meet my ambition. And that could have been in comedy,
Starting point is 00:07:25 that could have been in law school if I'd gotten into the law school I wanted to go to, that could have been in politics. I think I wasn't, it was, I was really not thinking clearly about what I enjoyed doing, what I cared about in terms of like what my passions were. I was so much more focused on external validation. And I was so much more focused on external validation. And I was able to get some of that via standup, at least in the kind of cobbled together way
Starting point is 00:07:53 you get some laughs at an open mic. I was able to get that in terms of like I had a good LSAT score. I was on the right path to go to a great law school. And then I saw this path in politics, I loved the West Wing and I thought, oh, maybe I'll become a speechwriter, right? That was something that was in my mind. And six months after I got this junior position
Starting point is 00:08:14 as a press staffer in the Senate, this opportunity came along to be a junior speechwriter for Hillary Clinton, I jumped at it. In part, I was there because I had actually written some jokes for her. She had gone to, was supposed to go to a roast. It was the roast of Barbara Walters to raise money for a Spina Bifida charity.
Starting point is 00:08:31 How does that happen? They had heard, I was working for John Corzine in his Senate office. It's a little, you know, not a lot of funny people on Capitol Hill. People had heard that I had done this barest of standup careers amateur. And so they asked if I would write some jokes
Starting point is 00:08:52 for Hillary Clinton. And so I got on the phone with the Hillary Clinton staff and some of their kind of outside friends who were helping write jokes, one of whom was Al Franken, which was a big deal for me at the time. And it would be a big deal now. As a comedian, not as a politician. No, no, no, it was before he was even, this was when he was just Al Franken, which was a big deal for me at the time. And it would be a big deal now. As a comedian, not as a politician. No, no, no, it was before he was even,
Starting point is 00:09:07 this was when he was just Al Franken, author, comedian, host of Air America Radio. And I wrote some jokes for Hillary Clinton, that stuck in their minds, and so I ended up getting a job as a junior speechwriter for Hillary Clinton, and so it happened very quickly. There were all these different paths. It was a few days after I decided not to go to law school
Starting point is 00:09:25 that the opportunity to be the speechwriter for Hillary had come along. And. How'd you decide not to go to law school? Like was that laborious, that decision? And disappointing to people who wanted you to go that path. It was haphazard and quickly made. I was in, I had enrolled at the University of Chicago Law School
Starting point is 00:09:47 and one of the reasons I allowed it to go on so long is it didn't require a deposit, which they should change. There was no deposit. So I was able to say I was going and it wasn't until I had to email, I think the truth is in my heart I didn't wanna go. I never wanted to go, but it was just the thing to do. And it was the moment when they required a photo
Starting point is 00:10:09 for the student Facebook. I mean, this is getting pretty close to when I would have literally started. I was like, I can't do it, I'm out. I withdrew. Not talking to anybody, this doesn't feel right. I'm going with intuition here. Yeah, that's right.
Starting point is 00:10:21 What was happening before with deep insecurity that you were looking for laughs, or looking for some sort of validation, what was going on there? I'm not sure, I'm sure it was just, I think that is a little bit my temperament. I think it's a little bit of growing up on Long Island, which is very kind of, where I grew up in Siosset, at that time.
Starting point is 00:10:51 It's very, very career driven. What are you gonna be when you're gonna grow up, get to the good school? It's a very practical place. Long Island's a practical place. And I had been closeted. I had not had a lot of friends, and so I was, I think, searching for the places where I would get the praise and the attention
Starting point is 00:11:12 and the validation that I needed. That's how I chose my career, just a teacher said you're good at that, and I was like, I'm good at something, so I wanna be good at something. What do you mean I can be good at something? And so that's just, there was no even second choice. Once I was good at a thing and once I could be good at that thing in a way that didn't
Starting point is 00:11:31 feel insecure, it just was easy to chase. Yeah, I also, I realize now looking back, and maybe this is the same for you, that it wasn't as though I was choosing one direction over others or that I was afraid of being rebellious or afraid of trying something else, wouldn't have even occurred to me, wouldn't have even have occurred to me to defy the kind of direction, right? Which was, you know, do your schoolwork, get good grades, law, math, right? It was like I just, I was not, it wasn't that I felt obliged to follow the rules. It wouldn't even have occurred to me.
Starting point is 00:12:06 How liberating though to go from what others wanted for you or what was practical in a practical upbringing and just to go, no, I'm gonna go be free. I'm gonna be free in all the regards. I wonder, yeah, I'll let you know when I do that. I wonder how it will feel. Well, but you chose, I mean professionally, you made when I do that. I wonder how it will feel. But you chose, I mean, professionally, you made some of the choices.
Starting point is 00:12:29 When you go from speechwriter to, no, I'm gonna take the things that I loved about stand-up comedy and politics, I'm gonna meld them and I'm gonna make it uniquely me and love it or leave it. Yeah, I got very lucky along the way in that I, I got very lucky along the way in that I, so I never felt like I was taking risks truthfully.
Starting point is 00:12:56 I mean, it didn't feel that way to me. So I get this opportunity to work in politics. So I take the job, I moved to DC. Then I get this opportunity to be a speech writer for Hillary. I'm doing that for three years. When I started working for Hillary Clinton in 2005. This is before anybody had heard of Barack or had just heard of Barack Obama because he had given the 2004 convention speech, but he wasn't a presidential candidate. She was the the figure that was going to go on.
Starting point is 00:13:18 And I thought, wow, I'm in this position. I'm going to I'm going to get to be on this this roller coaster. She obviously loses that race in 2008, and then all of a sudden I get this chance to apply to be a speechwriter at the White House working for President Obama. I apply, I get that job. I would say maybe the biggest risk I took in that time, I suppose not going to law school was betting on politics and taking a chance, but the biggest risk I took was after three. I suppose not going to law school was betting on politics and taking a chance, but the biggest risk I took
Starting point is 00:13:47 was after three years of being a speechwriter. That wouldn't look like a risk either if you so badly didn't wanna do it. Right, it just didn't make sense, exactly. And it wasn't as though I had a job in politics. And so when I decided to leave being a presidential speechwriter, When I decided to leave being a presidential speechwriter, to come out to LA to be a comedy writer and stand up,
Starting point is 00:14:10 that felt like I was finally making a choice. And I had felt this pressure. And this is what I mean by kind of being driven a bit too much by insecurity. I had this realization that, and now it sounds ridiculous to me, 10, 11, 12 years later, which is I had just turned 29
Starting point is 00:14:32 and I had this feeling that if I didn't leave and try comedy right now, I would never have been a young standup. I would never have done it. And so I had to get out before I turned 30. I set this artificial deadline and I left and I moved to LA and I didn't have any money. I had just a junior speechwriter salary from the government.
Starting point is 00:14:55 And so because I had this pedigree, I'd been working on both serious speeches for President Obama and I did a lot of his comedy writing when he did the White House Correspondence Dinners, which he'd gotten a lot of praise for, that had given me the credibility to get a blind script deal out in LA. A studio was willing to say,
Starting point is 00:15:16 hey, you have this interesting background, we'll give you the money to write a script. And that was the kind of bridge to get me to move to LA. And I thought I was gonna come out here, learn how to be a screenwriter, do stand up again. I did a little bit when I moved out here. You did some work with the newsroom
Starting point is 00:15:36 and you did a show, 16 Under Pen. And you must have poured your soul into those things. Like, those are dream projects? Like. So this is where, and anyone listening to this, I know it's, so I, it's gonna sound obnoxious. I moved to LA and the first, before I'd even had any sense of what I was going to do, this Josh Gad, who was then in Book of Mormon, Jason Weiner, who had directed the pilot of My Turn Family,
Starting point is 00:16:11 they had been kicking around this idea for a White House show. They knew that I had worked in the White House. So we got together and we developed this pitch for Josh Gad to play this Nerdywell son of a president. And it just worked and NBC wanted it. And so within days of moving to LA, I was basically working on this pilot that was like a fast moving train.
Starting point is 00:16:33 It was just happening. And so Dream Project, it was a, I was so, like my, my like imagination didn't have time to catch up to what was happening before I'd even gotten my bearings about what I would even want to do. I was working on a pilot that was going to shoot.
Starting point is 00:16:51 I had never written a pilot before. So I was, forget like a dream, I was overwhelmed. I was completely overwhelmed. I didn't know what I was doing. Okay, wait a minute. So this is not, so if I, but if I allow you to pull back from it and say, listen to what's going to happen to you in the future. You're gonna be doing this thing.
Starting point is 00:17:08 You wouldn't have been overwhelmed by that. You would have dreamt it. But once you get to the dream, you're overwhelmed by the dream because it's moving too fast and you don't know anything yet. Right, but this is what, of course, yes. I had no,
Starting point is 00:17:24 I am now 42. I was 29 at that time. I look back on those different portions of my career with a lot more generosity and forgiveness toward myself. I remember feeling so overwhelmed and like a failure when I was a speechwriter for Hillary. But of course I felt that way. I was 24 years old.
Starting point is 00:17:51 I had no idea what I was doing. And then I get out to LA again, I am in this completely new field working on my script. I have no idea. I'm like learning. I'm trying to read other people's scripts. I'm getting feedback from people. This is gonna be on television.
Starting point is 00:18:07 I've never written anything like this before. Is this imposter syndrome or you're saying, no, I was an imposter. I was an imposter. No, no, for a 1600 pound, imposter. I could fake it till I made it. I learned a lot. I could get through it.
Starting point is 00:18:20 But it never, it was fun and it was exciting, but part of what it required was a lot of pretend and having a lot of opinions that I truly felt, but that were meant to mask the fact that if people knew how unsure I was, like the whole thing would collapse on itself. There was a moment where they had,
Starting point is 00:18:46 because it was my first time working on a show, they had brought in an outside writer to do a rewrite of the pilot. He had a different sensibility. It just didn't work. And so now we're like days away from shooting and I'm just in this script trying to fix it. I've never done any of this before.
Starting point is 00:19:04 We ended up and figuring it out with Jason and with Josh and with some help from some other writers. But it was a very, it was more stressful than it was. Exciting. So a shit project, not a dream project. Like you liked it, like the idea of it's nice but the doing of it sucked. I, it was highs and lows.
Starting point is 00:19:24 Like I loved being on set. I loved pitching jokes. I also feel really, like, one of the parts of 600 Pen I'm the most proud of is we assembled an amazing group of writers. And the way we did it is I just read every script that came in. I treated it like a normal interview. And so I read a ton of material.
Starting point is 00:19:44 And that was a group of people, they've all gone on to be incredibly successful. And I feel proud of that because I feel like I had a good eye for this great group of people, all of whom have now really succeeded. And again, similar to, we talked about it before recording that, I felt like, you know what? I'm new here. I don't know what I'm doing.
Starting point is 00:20:11 I may at times not handle that perfectly. But you know what? Push comes to shove. I'm a great joke writer and I can take this the material that's coming in. I can figure out what's good and what's not, both for hiring writers, but also in terms of what the scripts were producing, and I'm really bringing value here, and there's a reason I'm here, and I'm making this project better.
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Starting point is 00:21:56 How many things like that in your arsenal or toolbox of talents do you say, no, I'm great at this? I have this, I have confidence here. I don't know, we'd have to start a pretty long list. No, I don't know, I feel, I think being a speechwriter, you don't have to be the best at anything, but you have to be competent or good at a lot of things.
Starting point is 00:22:23 You have to have a good kind of sense of politics. You have to be a good writer. You have to be able to synthesize a bunch of different points of view and inputs. And you have to have the ability to know when to say yes but or to say no but, to an edit, a change, a suggestion. And you also have to be able to put yourself in someone else's shoes.
Starting point is 00:22:59 You have to be able to say, all right, my job here, people would always ask me, like, oh, you were gay and you were, this was before politicians were in favor of gay marriage. That must've been hard. And the truth is it wasn't that hard because I never thought of my job as using speeches as a vehicle for expressing my opinions. My job was to inhabit the views and experiences
Starting point is 00:23:23 and voice of a different person. And so that was a big part of it. But I think those skills carrying, one of the places where I brought, I think, a comparative advantage is, yeah, I had that ability, but I also like, I can write a great joke, I can. And I'm a fast writer too. And I felt like those two things together
Starting point is 00:23:45 were part of my success as a speech writer and then as a fast writer too. And I felt like those two things together were part of my success as a speech writer and then as a comment writer. Well, you say you're a fast writer and there are a number of different things I wanna talk to you about here, but you say that what you do for love it or leave it in the monologue, that that takes you from 9 a.m. to 3 p.m.
Starting point is 00:23:59 So that doesn't sound like fast writing. That is a lot of curation for something that is is polished but is not an unspooling 70 minutes of I'm a fast writer. Well that's yeah well I'd say it's you know we get a ton of material in Wednesday night. I start editing it kind of make your way across a ton of material. Some of that's writing, some of that's editing, some of that's reading the news and figuring out what happened that you want, how you want to talk about it. Some of it is then jumping around.
Starting point is 00:24:33 We have, you know, let's say we have Tignotaro and her wife on the show, Stephanie Allen, we want to figure out that segment or we have, uh, a bunch of other guests that are coming on. What are we going to do with those guests? Thinking about that and you're getting pulled in a bunch of different directions. But, um, it takes a long time to go through a ton of material and you're also kind of going over it and going over it again. So once you sit down, you're down your fast right once you've got it like once you've got some sort of skeleton in your head You've gotten good enough at unspooling thoughts that you can sit down and do it Yeah, and I think also like just sort of coming up with a ton of different punch lines
Starting point is 00:25:16 the and just sort of going through it relatively Quickly the the this when I talk about being a fast writer though, I'm more mean like there were moments where you need a fast statement for the president to deliver about the Dow dropping or the show is in an hour, we need three new punch lines for this or you're on set and you're trying to figure out how to make a scene work. Like those are the moments where I feel like, you know what, like I can come up with something pretty quick that'll work.
Starting point is 00:25:51 But you thought that was gonna be your career then, right? Once you've gone into script writing, like where are you, when do you solidify, no, I know what I'm gonna chase now. Never, I don't do that. I've never thought that far ahead. Opportunities come, you take advantage of them. You know, I had this chance to be a speechwriter,
Starting point is 00:26:20 I took it, made the most of it. Had this opportunity to come out to LA and be a TV writer, I took it, made the most of it. Had this opportunity to come out to LA and be a TV writer, I took it. You just grab opportunities or. But crooked media. That, so, you know, I was a speechwriter for Hillary, speechwriter for Obama, TV writer, did 1600 pen, wrote some pilots, worked on the newsroom.
Starting point is 00:26:41 But there was this pull to politics that I did feel throughout that time. The, and this is where I sort of would land on in terms of like the biggest chance I took, the biggest risk I took was crooked media. And it was after Trump had won, we had been doing this podcast for the ringer that had garnered some success.
Starting point is 00:27:03 A podcast that you didn't intend to continue, right? Probably not. We really hadn't thought that far ahead. We were doing it through the election. But I remember after Trump won, the next day we had to do this live stream. We were driving, it was John Favreau, Tommy Vitor and I were driving in my car to the Sunset Gower lot
Starting point is 00:27:22 to do this live stream. My car ran out of gas. We pushed to the side of the road in front of the CNN building where a bunch of people were watching CNN and Trump accepting his victory. And we walked to the studio talking about what we would do now. None of us felt like we wanted to do was go back to our day jobs. We really wanted to figure out how to focus on this. And we thought, well, we have this podcast,
Starting point is 00:27:49 let's see if we can turn a podcast into something bigger. And we started hatching this idea for Cricket Media. We didn't have the name, we didn't have really any idea of what it would be. But is it buddies on the side of the road feeling something that feels like inspiration, restlessness, wistfulness? Like when you're talking about, look, we've got this gorilla outfit, there's CNN, there's the
Starting point is 00:28:08 symbolism of mainstream media, and here we are running out of gas. Let's do something else with our lives at this age. That's a good question. I don't think it was as reflective as all that. I think it was a feeling like we have to do something and less about what it would be and more about what we realized we didn't want to do, right? That we didn't feel like what we were, we were certainly not inspired to go back to, you know, they had a communications consultancy.
Starting point is 00:28:44 I was a TV writer, which I loved doing, but there was this feeling like, no, we should put our energies into this moment. This is, Trump winning is such a calamity on so many different levels. It is a representation of so much failure. And there was an urgency in that moment. And I had had some, we all had at that point enough success that we had a little bit of wiggle room, right? That we could start something and have say six months
Starting point is 00:29:20 to see what would happen. And so that gave us the space to think what could we make. And we started thinking about what the podcast would be called. We started thinking about what the company would be called. We really didn't have much. We knew we were going to start with podcasts. We knew it would be a media network. The core idea was that there were activist groups and there were some left-leaning media organizations,
Starting point is 00:29:51 but those two things were not intertwined. What the right had and still has, it's only gotten worse, is they had media that is 100% bought into their political project. That is, Fox News exists to hurt Democrats and help Republicans. Now, we didn't ever want to make something that was as dishonest, that felt like propaganda, that was unwilling to criticize our own side. But we did want to create a media company that said, hey, we believe democracy is under attack right now. We are a pro-democracy media company, unabashed in that point of view.
Starting point is 00:30:28 And we welcome anybody who wants to be a part of that. And we're not just gonna treat people like observers, the way mainstream media does, like kind of that treats the viewers as if they're aliens watching United States from spaceships. We're gonna remind everyone that they are participants and that it's not a game, there are real stakes, and we all have agency.
Starting point is 00:30:50 So we have to do something is an inspiration, it's anger. Anger is my motivation. I'm not a hope guy, I'm an anger guy. I'm motivated by anger, always have been. I find that it's what I'm at my bravest and most interesting. So, like there's been, nothing's bothered me more. No, a lot of things have bothered me more.
Starting point is 00:31:13 But one thing that has bothered me over the years is when someone says like, I'm just looking for a politician who inspires me. And it's a real misunderstanding of what politics is and what it's for. I view inspiration as a valuable tool. It is important that politicians, the political figures, that leaders be inspiring. Inspiration has great value.
Starting point is 00:31:37 It helps people change their perspective. It helps people broaden their perspective. It helps people imagine themselves taking actions or being part of a movement they might otherwise be. That's what inspiration does. It has political value. But you, as a person watching a speech saying, I need to be inspired, what does that mean?
Starting point is 00:31:58 It means you know what the right thing is, but you need someone to tug at your hardstrings to get you to do it. If you are saying you need to be inspired, then you already understand the delta between what you're currently doing and what you believe you should be doing. So you actually don't need inspiration. And it is the kind of end result of several decades of political punditry that treats everybody watching like they are fully, fully cognizant, fully informed observers who can't be persuaded.
Starting point is 00:32:33 It has changed the way people think and talk about politics. They no longer say, here's what I believe, here's what I want. They say, here's what I think works. Here's why I think that's a bad look. Here's why I think that's bad politics. And so for me, I personally don't need inspiration from politicians.
Starting point is 00:32:49 I need them to have it to persuade others, but I am not in this to feel any kind of warm and fuzzy feelings. If you're not choosing your path because there's some luck here, are the opportunities presenting to the adult as the validation that the teenager needed? I'm not sure. I don't think... I don't think, I like to think I've moved beyond that.
Starting point is 00:33:33 I think it's more not, I have found it fruitful in my life to not think of a career as a very long path, but as just a series of discrete decisions. And you make those decisions as best you can. In the moment, you see where you land. And then from there, you'll have gained new experience, new wisdom, new insight, and more knowledge from which you can make the next decision. But I have never thought of it as a path,
Starting point is 00:34:00 more like you're kind of going from these islands, these little sort of staging grounds to take and to not look to, and looking too far ahead I think is not particularly valuable for me, for me. Maybe that's just a reflection of undiagnosed ADHD that the idea of thinking three or four moves ahead seems impossible. So I'm just trying to get to the next stop. Where is your mind a blessing and where is it a curse?
Starting point is 00:34:29 What a funny, very, very, so that's a very Barbara Walters in the 90s type question. Is it? I wasn't trying to bring Barbara here with us, but I just, I know I can't, you sound like you obviously think a lot and that can, I know in my case if I'm thinking a lot sometimes I get the comfort of the illusion of control, but it's like I really would like it all to slow down
Starting point is 00:34:58 in my head. And I am lucky to be, I'm very curious. I don't find myself, I find myself interested in the ways in which we've done things for a long time a certain way without really much of a reason and I find myself looking for those seams. Sometimes that's right, sometimes that's wrong. I think that my kind of floating around has been really good for me. I've gotten to have this incredibly varied career, right? Like I ended up, you know, when I was a math student,
Starting point is 00:35:48 I ended up publishing a math paper. I go into politics. I had this incredible speech writing, short but incredible speech writing career. I had success as a television writer and now I've had success with Crooked and with Potsy of America and with Love It or Leave It and I feel like that, I was very fortunate that the fact that I'm able to kind
Starting point is 00:36:12 of, that like I get curious and interested and intense about a certain idea or certain project and I can really focus on that and then kind of can fully switch gears,. I've been really rewarded for that. But I do think I've paid a price for not being able to quiet that noise. And there have been times in my life where I have not been able to really drill down and get something right. Like I had this pilot for a drama, it was called Anthem. It was set up at showtime.
Starting point is 00:36:48 It was about an American election that falls into chaos because both sides declare victory. And I was writing that in 2014, 2015. Like it was ahead. I was like, I had, and I just couldn't get it right. I was, I had, and I just couldn't get it right. And I like, and so I, and the struggle of that, I would just get pulled in a bunch of different directions and like kind of put it aside, come back to it,
Starting point is 00:37:16 put it aside, come back to it. And I wasn't really able to give it the attention and focus, sustained attention and focus that could have made it a great show. And I feel like I not only let myself down, I let the people down who bet on it. And there are smaller examples of that, but I think that's the price.
Starting point is 00:37:36 It doesn't seem like there's much serenity in it. No, I'm not a serene person. I'm not a serene person, no. You don't aspire to it, like you don't crave it in any way because when I'm asking you these questions it's because it's sort of, I recognize some of what you're talking about here and I crave a different experience with it, even though,
Starting point is 00:37:55 because when you said rewards, I was gonna ask you, is one of the rewards happy? Like, I mean, fulfilled maybe, but I'm just saying, I'm joyous while I'm doing it. Seems like what you're doing now is so uniquely yours yeah that it would it would be proprietary in a way that would be enriching look I get to do the fact that I had this comedy experience I had this writing experience I had this political speech writing experience
Starting point is 00:38:25 and it all coalesces into what I get to do now. That's the great luck of my life. I'm very fortunate and I love a lot of what I do. I get stressed out about a lot of what I do. The times I beat myself up a little is when you get frustrated or annoyed or impatient and you're like, things are good. In terms of where you are in your career,
Starting point is 00:38:47 things are good. Things are happening in the country are a nightmare, but you are where you're supposed to be. You should feel very fortunate. You should feel very grateful. You shouldn't lose sight of that even in moments when life is tense or. I could learn from that.
Starting point is 00:39:00 I do not, I wish I could say all of those same things and my daily steps don't have that kind of gratitude. And it's the way they should. Same, I'm saying that's what I should be doing. Completely agree, completely the same. But I do think for me, the pandemic was obvious, like there's, there's this F. Scott Fitzgerald series of essays called The Crack Up.
Starting point is 00:39:32 Have you ever heard of The Crack Up? I have not. F. Scott Fitzgerald wrote this collection. It's now a collection. I think it was in three parts at the time, but you can get it as one very short, short book or long article. And it's an interesting document because he doesn't have the terms for,
Starting point is 00:39:54 I don't know what you would call it, manic depressive, bipolar, addiction, whatever. But he is sorting through and describing how he is living. And he's describing deep depression, manic episodes, whatever. And he's writing in the middle of it, which is something strange, right? You just don't normally see that. And he talks about being what is, I think, just clinical depression, sleeping all day, and
Starting point is 00:40:25 he's writing lists to occupy his mind. And one of the lists is times in which he was snubbed by those who are not his better in character or ability, which I always think about. But isn't that a great line, right? I mean, yeah. It's just snuffed by people who aren't better than I am in any way. And this is not merit-based.
Starting point is 00:40:50 What a- Making a list of it. The most, I couldn't think of anything more Los Angeles than that, but he talks about feeling quite comfortable in that mode of living. And then he says, and then I got a little better and I cracked like a plate when I heard the news. And for me, the pandemic brought me low enough
Starting point is 00:41:12 that it gave me the chance to get a little better and crack like a plate when I heard the news. I made a lot of changes in my life after more than a decade long relationship ended. Over the course of the pandemic had become a little too comfortable using an edible at the end of the day to avoid thinking about the problems I wanted to delay one day, which I did over and over and over again.
Starting point is 00:41:45 And it led me to, I think, change a bit how I think about what I do, how I do it, and to try to find, to try to think less about what I want to be and more about what I want to be doing, and to try to take a bit more joy in it. And I do think that was the end of like what was, I think I'm always a person that's prone to being a little bit depressed, but getting a bit lower helped me see the need to get a bit higher. And I think after that, I've been on this ramp up and I feel like I am still living in the kind of noisy chaotic way I always have but I'm a little bit more I have a little bit more generosity with myself I think I'm a better friend I think I'm better at my job and I think I'm just a little bit wiser at the end of that. I'm sure I
Starting point is 00:42:50 will look back on this and feel like I've still got plenty of place to grow. Still not kind enough to yourself? I don't think so. Yeah, no, I don't think so. It's more too about like, maybe you feel this too, which is as you get older, kind of understanding the distinction between, here are the places where I would like to be better, right? And kind of address some of these issues. And then here are the areas where, you know what? That's just fucking me.
Starting point is 00:43:26 That's what I'm like, that's it. And this is cooked. This part, this part's cooked all the way through. You put the fork in this part, it comes out clean. If ingredients in love are acceptance and understanding and that, like there's real wisdom in that. You have to do that. I'm good with that, about myself.
Starting point is 00:43:42 Well, you know, this sort of in a kind of like self-help culture, I think too often, right? Like it's hard because some of us do have, we all have to change, right? Like it's like you have to, you have to understand the ways in which you need to be working on yourself. You need to be growing. You need to not feel like you're done.
Starting point is 00:44:02 But and also loving yourself in there. Like I'm telling you, because it's something, I needed the help of a relationship to do that. I don't know where or what age cavemen can go about being formed and stuff, but I had, like I needed some help being kinder to myself. Even with the consciousness, I wasn't getting there myself, and it's still a perpetual fight,
Starting point is 00:44:25 but I absolutely needed nudges along the ways and all the blind spots I have around my insecurities. Yes, yes. And for me too, it's like a happy, really good relationship has been helpful. Honestly, it's strange to say, but Manjaro, going on Manjaro has taken a big source of my self-loathing. Did you have body image issues?
Starting point is 00:44:49 Tons still do. That's, that was, that, a huge, a huge problem for me, huge, huge. Yeah, I've had them all my life. And I remember when I was, I was talking to my therapist about it and she was really funny. She was like, you're gonna go on this thing,
Starting point is 00:45:08 and all the ways in which you kind of obsessively self-criticize, they're just gonna find some new avenue, right? Let's say you go on this drug, and it helps you lose a whole bunch of weight. You're not gonna stop finding ways to criticize yourself. And I was like, maybe not, let's find out. And the truth is, like,
Starting point is 00:45:23 the truth is it's somewhere in the middle, right? Like I, it, no, of course it is. It's pessimistic. Well, but it is. Of your therapist, I'm saying. Oh no, well she was her concern. It was that, it was like, hey, we should, she was not against my going on it.
Starting point is 00:45:36 It was more, hey, like go on it, don't go on it, but we still have to do the work. Like this isn't gonna address the work, which is correct. And my, and I actually like, like made a chart and was like, okay, we have this much self-criticism about everything that's not my body, and we have this much about my body.
Starting point is 00:45:53 If we lower this by 50%, this will go up, but probably not in equal measure. And I think we'll net out, we're gonna net out with less self-criticism. Absolutely, there's all kinds of ways in which people, this is- The math is useful there. So here, I'll give you, here's one, I'll give you,
Starting point is 00:46:11 this is one which is, okay, I want you to imagine, okay, an X and a Y. On the Y, we have gregariousness. I'm sorry, on the X, we have gregariousness. On'm sorry, on the X we have gregariousness. On the Y we have charisma, okay? Gregariousness at the bottom, charisma going up and down. All right. There's a diagonal line that runs
Starting point is 00:46:35 from the bottom all the way to the top. When you are below that line, you are more gregarious than you are charismatic. You're annoying. When you're above that line, you're more charismatic than you are charismatic, you're annoying. When you're above that line, you're more charismatic than you are gregarious. You're exciting and enticing to be around. If you are extremely charming, okay,
Starting point is 00:46:54 extremely charging, but very low gregariousness, you're extremely cool, because you're just not giving it out, right? If you're extremely gregarious, but not at all charming, you're a boar. And what you wanna do in your life is stay below the cool boar line. Above the cool boar line.
Starting point is 00:47:14 You wanna be above that line. You wanna be above that line. Gets distorted though by, you know, less fat, less funding. Well, there's that challenge. That is challenge. I remember when we were making 1600 Penn, Josh, between the pilot and the shooting he was like he lost a bunch of weight and we were always joking that he's lost, he lost like 15 pounds of hilarious. It's unbelievable. It's hilarious, it's all
Starting point is 00:47:40 fallen off you. It's not great for anybody involved. The building of a media company when you say you didn't see any of it as risk, I'm wondering what's happening there in terms of you not considering consequences because I didn't actually think that there was much risk in leaving the safety of ESPN. But that was foolhardy. That was more confident than I should have been about things. I should have been plagued by the insecurity that would do more risk assessment than I did. Yeah, so we, so I do think it was a risk. We had some runway, but it was a risk. I think we were fortunate in that we weren't like, it wasn't that we, what we were doing
Starting point is 00:48:32 is leaving jobs that we couldn't get back to start a media company. We were taking a break from the careers that we had, which we could return to. But nonetheless, we had a mission statement, we had a core set of goals and values and we knew what it should feel like. We didn't have a business plan. We really didn't know anything about what it would take or what it would look like. What a cool thing to chase though. We knew what it should feel like. That's a pretty good one to look,
Starting point is 00:49:09 especially at the age you're in, especially if you're doing some examination of, if you're doing relationship and pandemic adjacent thinking, even though it was earlier. This was earlier. And we were, we realized, we were, where we we got luckiest is so the three of us started it. We hired three people right away We hired someone to be our assistant to help us manage all this we hired Coo and we hired a chief content officer and those were incredible hires
Starting point is 00:49:43 who really helped us build this. And without them, it wouldn't have happened. And so that group of six really were able to figure out the next group of hires. And Sarah, who was the COO, was able to really build a business plan. And we launched the show in January and we gave ourselves a couple of months. Then we said three months to get the audience.
Starting point is 00:50:14 We were starting from scratch. We never in our assessment, we literally launched zero subscribers. We gave ourselves three months to get back to where we were in the ringer. Within an episode or two, the audience was back. Within three or four episodes, the audience had doubled. And then we were kind of off to the races.
Starting point is 00:50:35 And that gave us the space to launch other shows. And we basically, because we were so lean when we started, we never had to take investment, which meant we never had debt or shareholders who were breathing down our neck to grow, grow, grow, grow, grow, we were able to be deliberate and careful. That was a double-edged sword. Because on the one hand, we have been profitable,
Starting point is 00:51:01 we have never not been profitable. And that's strange for immediate companies, or certainly immediate company startup. But it also meant that we never had that, like what had to drive our growth was the project itself, the belief in the company and wanting the company to be bigger, reach more people, fulfill its mission. It never, we never had the kind of like,
Starting point is 00:51:25 we never had like a tech bro behind us breathing down our neck. No, your way of doing it sounds better than my way of doing it because I went straight to 43 employees and investors. I like your way better. It seems like there's more control over that. Absolutely. There has been more control,
Starting point is 00:51:40 but I sometimes think too, like you have, when you have what you have, there's a fire. There's a, there's an fire. There's an urgency. And so we had to generate our own urgency, which we did, which we did. So look, we've grown a ton. I went from five to 10 to 15 to 20 to 40 to 80, I think we're at 100 right now, people.
Starting point is 00:52:00 And we've launched dozens of shows, we've built out YouTube, we're now, we've done touring, we've launched Vote Save America, which is our kind of activism arm and seeing great success there. So like we've grown a ton. The most professionally fulfilling thing you've done, yes? Yeah, cricket, yeah.
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Starting point is 00:53:16 Three times the points. Conditions apply. Visit rbc.com slash ion cards. What kind of challenges are there to the friendship? So, there are absolutely challenges to it. I think what I've... The reason I ask the question is because I work with a lot of my friends and I have a lot of friends that I'd like to work with that are like, hold on a second, I think this
Starting point is 00:53:38 is going to do... We throw money in this, it's going to mess a whole bunch of things up. So I think you're combining two issues. One issue is does working with your friends change your relationship? Of course it does. Of course it does. Then there's how do you work with your friends?
Starting point is 00:53:58 What I remember having this realization early on, which was it's not much of a realization, but like wow, all bands really do break up, you know? And we are not just, it's, we are a band, but we're also kind of a record label, you know? We're kind of doing both at the same time. We are the hosts of the show. We're also building this company.
Starting point is 00:54:22 And realizing that, We're also building this company. And realizing that in that kind of an environment in which there is stress, there's disagreement, there's a lot of incredibly rewarding moments that you share. Conflict that creates creativity. There's creative conflict, there's just different points of view. There's ego, right? You're hosting this thing together. There's history. There's all of that.
Starting point is 00:54:49 And realizing that really what you're doing is you're never gonna, it's not making sure you're working well together is not like a problem you solve. There's just a, it's a project, right? It's something you're gonna have to maintain. There's gonna be little moments that pop up
Starting point is 00:55:09 and you have to talk about them and you have to be honest about them. And you can't let it build up. You can't think like, oh, things are good, or, oh, we're having problems. It's that you are always going, there's always just a, you have to just kind of watch the pressure dials, right?
Starting point is 00:55:22 There's just gonna be some pressure dials. And it's okay, there's gonna be moments of tension between everybody. That's okay, but you're gonna work with them and talk because you care about each other. You have the same mission, you have the same goals. You're loyal to each other in each other's corner. You know, we don't all see things the same way.
Starting point is 00:55:41 We've had, you know, our conflicts over the years, but we ended up years later going through, we took on investors and we were working through the paperwork, a lot of paperwork. And there are always these questions about like, well, what if you guys disagree or what? And we were always just like, look, we annoy each other sometimes, but like, there was, we always would say like, don't worry about what happens if the three of us disagree. Like, if you're our lawyers and you're trying to protect us
Starting point is 00:56:22 for what happens if we start disagreeing and don't worry about that. We will have each other's backs. We never need to worry about that. And I think that's been a really, underneath all of it, knowing that we are, that we can truly at the deepest level trust each other makes it so that you don't have to, in the end,
Starting point is 00:56:43 worry about a ton of problems that other companies have have to in the end worry about a ton of problems that other companies have to deal with. But you say, yeah, work's going to change the friendship, of course. You say that. You knew that beforehand? Because, or did you learn it? Because I wouldn't say that it would have to change it if it's working ideally. It doesn't mean that there aren't going to be challenges to it, but I would hope or I would aspire to have the friendship be something even better, deeper after I've worked with my friends. It's just going to be different. But people will tell you, don't do that.
Starting point is 00:57:14 Don't think like that. Well, first of all, John and I met, he hired me. We were colleagues before we were friends. Tommy and John worked together for years. So it's a little bit less, it's not as simple as that, but if you're gonna spend all day working with somebody, you've seen them all day, it's different. You're not gonna like, you have a work relationship
Starting point is 00:57:41 and you spend already a ton of time together. It's just gonna change your dynamic outside of work. That's not a bad thing or a good thing, it's a different thing. I think there are plenty of people who can't work with their friends, right? That's not us. But like if you have a great friend in your life
Starting point is 00:58:00 who you see each other after work a couple times a week or a couple times a month and you catch up about life and you spend Saturdays working out together and then go into a movie or something. Like if you work together, it's gonna be different. It's gonna be different. That's not a good thing or a bad thing,
Starting point is 00:58:14 but just it is gonna be a change. And you have to just, we, we'll achieve, we never talked about that. It was just, this was what we have to do. This is what we're doing. It was absolutely the right thing. We never talked about that. This was what we have to do. This is what we're doing. It was absolutely the right thing. What's been the hardest thing?
Starting point is 00:58:32 What has been the hardest thing? So I don't know what the hardest thing is. The couple things, one is you go from hiring everybody to hiring the people, hiring everybody, to you come into the office and there's just somebody that's there and they don't know you. That's real success though. Well, sure.
Starting point is 00:58:51 That's of course, but it's it. I mean, but that's the climb up the management ladder right there. Like that's how you end up being founders of a company. What you, it aspirationally, you want to get to somebody else doing everything. But it's more, but it's more that, um, I think for me, it's like, I, uh, like the, the way it, the way it felt when it was 10 or 20, just different
Starting point is 00:59:17 when it's a hundred and it's hard for you, you realize, oh, you, like, it's hard to convince somebody that, you know, they can talk shit to you, right? If you feel like you're their boss's boss's boss, you know what I mean? It just, it's different. Yeah. Well, I, yeah, I, because I work with so many of the same people for so long,
Starting point is 00:59:39 like I absolutely lose sight all the time of, oh, this person's receiving me this way now because I'm in charge or even more overtly in charge. And so I can't be exactly the same that I was before, but I haven't actually learned that lesson. I just keep making the same mistake. Yeah, there's that. I also think one challenge has been
Starting point is 01:00:10 as the company has grown, realizing that making sure that you are maintaining the voice of the company in a way that is both narrow enough that you haven't lost what crooked media is, but expansive enough that as new and interesting and talented people come in, they lend their voice to the company as well and make it better, right? So it's when are you demanding conformity versus demanding consistency, which are different things? That's been a challenge for me. Prioritizing has always been a problem for me. It is hard to be, you know, I'm a host on Mondays,
Starting point is 01:00:59 I'm a host on Thursdays, I'm in a lot of other kinds of meetings, Wednesdays, Tuesdays, Fridays. How do you feel about all that right because I've gotten a lot of advice from people don't do both things you can't be both you can't be an executive and and the microphone both will be worse and I felt it like I have absolutely felt that the shit I'm doing that I don't want to be doing that has to do with running a company is absolutely getting in the way of the other things that I do and I can't get it out of the way.
Starting point is 01:01:29 Like there's no. That's a problem. It's a huge problem. Yeah, it's a huge problem. That's it. That's it? You don't have any good advice for me on how to fix that? Because what you're doing on Thursday, if that's your happy space and you're the founder
Starting point is 01:01:43 of the company, like the thing that you just said that I thought was most interesting about just where the mirror is for me on, did you just look at your watch? No. You looked at your watch. No, keep going, keep going. Did they catch you looking at your watch? I caught it out of the corner of my eye. You're very observant. It is going long. I'm happy to, I'm happy to. The success, I'm just playing with you, the success of. Maybe I could deny that. I should have denied it. I should have denied it.
Starting point is 01:02:12 You caught me but I should have. I could have gotten away with it. No, I didn't. The way that the person on outside looking at this saying, what do you mean it doesn't feel like success to have people hiring people before you see them and one day you're the one paying a person who is coming to your office and you're like, who is that person? That is a sign of success that neither you nor I are absorbing as success. And furthermore, you're going the next point of saying, and
Starting point is 01:02:43 also I can't commit to a company that has the soul that I want it to have if I don't have more interest in that person. And one of the challenges I've faced in not having quite enough management for the number of employees that I have is in the absence of like real care and communication, what falls into those cracks can be like trust and things that you just don't want to have with your employees. I think fundamentally I think all of these things tie back to what happens when you're moving too fast, right?
Starting point is 01:03:19 And when you're moving too fast, sometimes the shows you're hosting may suffer a little bit because you haven't paid enough attention to them. Sometimes you're kind of in, like you're kind of, I sometimes joke that like, oh, I'm sorry to pop in like the Babadook, right? Like, like, because something's, there's a process, something's unfolding and then I sort of like pop up to change it or to have an opinion. But I think in a deeper way, what you're talking about too is like I think sometimes when you're moving fast you realize oh like I I didn't I wasn't in a like I could have approached that in a more sensitive way right or I could
Starting point is 01:04:01 have I was I was brusque in that moment. I punched myself in the face though. I'm not gentle with myself there. Once I've realized, oh, I could have done this. I am like. Yeah, of course, of course. And I do the same. And, and, but it's that like, how do I make sure? And some of it is also just letting go of certain things
Starting point is 01:04:21 and knowing that it's not maybe exactly how you would do it but it's still being done well, even if it's not the way you think it should be going. That one's tough for me. Yeah, it's tough and it's also part of it too, it's like I've noticed too, you have really good people, they're doing a great job, but you don't feel like you've done enough
Starting point is 01:04:44 to convey what the goal is or what the tone of it should be and then you have to be in it along the way. And that's your fault for having not done a good enough job at the start on the front. But I think part of it too is like, I like being busy. To go back to where we started, I have a very good relationship.
Starting point is 01:05:12 I like being pulled in a million different directions. I like a busy day. I'm gonna go from here, I was looking at my lunch, because I'm gonna go back from here, run back, we're gonna meet to talk about a design thing with this incredible designer who runs in our design team. Then I'm gonna meet with the Love Her, Leave Her team to plan a bunch of stuff.
Starting point is 01:05:26 Then I'm gonna meet with the politics team to talk about what we're doing with Boat Save America. And I love getting to do all those different things. And as long as I feel, there's a meeting we do called Comedy Corner. And it's a meeting that started five or six years ago. Comedy Corner was the name of a few funny people at the company, different jobs,
Starting point is 01:05:45 who just get together and brainstorm funny things we could do. And then it's now, as we're 100 people, it's now grown into a weekly meeting run by Hallie Kiefer, who's the head writer of Love to Leave It, where people come to pitch and also to get ideas for their projects. So we need a merch idea,
Starting point is 01:05:58 we're naming this website or whatever it is. And I don't go, it used to be my meeting, now I kind of go once in a while. And I'll be in the meeting and we'll be pitching. And I'll throw a couple ideas. And a lot of times, if the meeting is pitching something for my show, I actually don't go.
Starting point is 01:06:19 Because then it becomes pitching me, which is not the purpose. But I like to try to go and just be a person pitching. Like, it's not my meeting, I'm just here to throw out ideas. And we'll joke, especially with the people that have been there a long time, like, did I add anything to this meeting? Should I have come to this?
Starting point is 01:06:34 Because sometimes if I go, and then all of a sudden everyone's pitching at me, that ruins the meeting. But then sometimes I'll come and I'll be like, oh, you know what, I have an idea. And they're like, all right, I still got it. I can still do it. I wonder if somewhere in there you, in liking to be pulled in a lot of different directions, if you slow down anywhere in there to absorb the emotional gratitude, because this one I have gotten life to slow down here of my god look
Starting point is 01:07:06 look at this I'm presiding over a writer's room that I have the ability to to harm or help by my present but it's mine it's yeah I don't think that's healthy I think it's not I think it's more like are you doing good work are you adding value you don't think it's healthy to slow your life down to have a gratitude for what it is that you've built while you're inside of it? I think that's the wrong thing to care about. I think it is, I think taking,
Starting point is 01:07:38 I think taking too much esteem from that is the wrong thing to care about. It's good, it's great, it's good, esteem is assembled. But like, I think kind of like, behold what we have built is a bad instinct. And I don't think that, I think that is a little bit, a little bit of like kind of,
Starting point is 01:07:57 there's arrogance in it. And so I feel those things, but I don't think those are good feelings to feel. I think better to feel more, I don't want to let this group of people down. And if I'm here, I want to make sure that I'm doing what I'm supposed to do to validate everyone who's decided to be here. Like I think for me, I really take a lot of joy in like in routine and kind of like hitting my marks in each of these places. And I feel most proud when I am able to bounce from all of these
Starting point is 01:08:45 and play these different parts and do it well and do it with kind of joy in the moment. That's when I'll be like, you know what? It's not like, oh, look what I've assembled, but more like, we love it or leave it. Somebody said this, like, people always say like, oh wow, you guys have a lot of fun in those meetings. And we do.
Starting point is 01:09:09 And that's to me when I feel the most joy. It's not like, oh wow, it's more like, like we're putting the show together and we're laughing the whole time. We're having a blast. And everybody feels like they're doing good work in a show they believe in, in part because they trust that I will deliver when I have to deliver. I love how gentle you were about telling me to my face that I was arrogant about that, but I do,
Starting point is 01:09:32 and there is, it can be all of these things. Didn't say that actually. I said that it's a thought process that could encourage arrogance, which I feel, which is why I fight it. You said it was unhealthy. I think it could be unhealthy. And you made me think about, oh, can it be?
Starting point is 01:09:48 Is this ego instead of gratitude? Because we're articulating, I think, the same thing a different way, but you're saying that something's unhealthy. When I'm saying that I have trouble in my life slowing it down enough to have the appreciation of, oh, what a majestic thing to be able to laugh this way with this group of people, and to be able to also have it be yours, right? Like both the responsibility of it,
Starting point is 01:10:15 that's the next step that you don't like to have it be yours because this is very much yours. You broke away to have something that the three of you would have. I guess. I guess that's right. I guess I just, I think it's, I think that that's the wrong kind of pride. I think that's the wrong kind of pride for me. Maybe because I feel like I will take too much from it. If you're that aware of it though, if you're that aware that this is unhealthy, this is
Starting point is 01:10:51 a poison to me. I think it's a little kind of like, you know, Simba, everything the light touches, I think that's all unhealthy. It would get in the way of the work being good if you spend too much time there because you wouldn't care so much about it getting better. I think if there's value to you saying, you know, this is hard, this can be frustrating, but like look how far we've come, look what we've made already. I don't think there's anything wrong with any of this.
Starting point is 01:11:18 For me, I'm just thinking like what is that instinct? I think it's an instinct towards arrogance that's worth fighting because it's also, I don't, I take, I have trouble with the word yours. You oversee this thing that you've helped build. It is a result of a lot of people's work. It's a result of a lot of luck. It's a result of a lot of luck, it's a result of a lot of talent. You reap a lot of the benefits from it.
Starting point is 01:11:50 But it's a collective work as well. That's healthier for your company. Maybe for you and your company. I think so. Like if they're feeling that off of you. I hope so, I hope so, I think so. Like if they're feeling that off of you. I hope so. I hope so. I hope so. I will let you go on this note a complicated question because I don't know how this felt to you negotiating for one year over unionization at your company. A progressive
Starting point is 01:12:18 company that prides itself I'm sure on being good to people. Absolutely. That cares about it. Absolutely. And then all of a sudden you've got a company so big that you're, you itself, I'm sure, on being good to people that cares about. Absolutely, absolutely. And then all of a sudden you've got a company so big that you're, I imagine that when all of this path was in the making, you did not imagine negotiations with a union over lawyer language stuff. I think what we took from that experience is, you know, we went from, I'm't, I'm going to get these numbers a little bit wrong, but say roughly from, we like more than doubled in size during the pandemic. And that's a
Starting point is 01:12:54 lot of time and a lot of culture to develop when people are sitting in their homes and not together. And you are being fundamentally altered during this period because of the changes you're deciding to make. Everybody's going through it. Everybody went through it. Everybody went through it during the pandemic. Now everybody, everybody, everybody, everybody. And we grew a lot and we changed a lot.
Starting point is 01:13:17 And we also were kind of, our business was growing and changing. We were working with Sirius. We were taking on investors. And I think we had a lot of work to do to build better communication across the company, not only to convey both also, first of all, we had to figure out what direction we're going in. Then we had to convey that. And then we had to work with everybody to build a collaborative, trusting, positive culture for the company. And I think that is something that came, the realization of how important that was, I think,
Starting point is 01:14:00 became clear through the collective bargaining process. But I will say now that we're on the other side of it, I feel like there was a lot of kind of growth we did together to get to that agreement and now we have that agreement and I do feel like we're in a really good place. Congratulations on all your success. Thank you. I will let you go to all of your many things. Sure, sure. It sounds like a frantic life.
Starting point is 01:14:31 No, it sounds, yes. It looks like you love it. When I walked in, you were like, are you stressed? It's like, no, this is baseline. This is just who I am. This is baseline. Yeah, for sure. I just, well, you swept into the room
Starting point is 01:14:41 and I'm going to say it was a bit of a tornado of it. I couldn't place it. Is that anxiety? What is it? Is it frenzy? It's energy, it's a lot. But you could love it or leave it. You could also pod Save America with him.
Starting point is 01:14:53 It's all things crooked media. I appreciate the time and the honesty. Thank you. And for being so contemplative in the questions and the answers. Nice to have a chance to slow down. Yes. I forced it upon you. Nice to have a chance to slow down. Yes. I forced it upon you.
Starting point is 01:15:06 Nice to have a chance to be arrogant. I love that part. I never said, for the record, if you go back and listen, I mean we have this recording. Unhealthy, arrogant, unhealthy kind of thing. I said it could lead to it. I said it could be unhealthy. What we have recorded is that you looked at your watch.
Starting point is 01:15:17 I saw you look at your watch. I did look at my watch, I'm looking at it again. I was talking and you looked at your fucking watch. I subtly, subtly, there's no clock in here. Oh, there is a clock right fucking there. I could have just looked to my right. I fucked this whole thing up. Yeah.
Starting point is 01:15:30 ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"]
Starting point is 01:15:38 ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"]
Starting point is 01:15:46 ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"] ["Dance of the Sugar Plum Fairy"]

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