The Dan Le Batard Show with Stugotz - The Best of SBS: Pod Save America's Jon Lovett & Tommy Vietor

Episode Date: November 27, 2025

Nothing says Thanksgiving like that awkward political conversation with the family... Let us be thankful we have Jon Lovett and Tommy Vietor's "Pod Save America" for all those other times!    Dan welcomed the co-founders of Crooked Media for a conversation about the never-ending challenges of having careers in politics and what they've learned from starting media companies with their friends... and everything they still haven't figured out. For more of Jon, Tommy, and Crooked Media, go to Crooked.com and watch, listen and subscribe to “Pod Save America”, "Pod Save The World", and “Lovett or Leave it”. Learn more about your ad choices. Visit podcastchoices.com/adchoices

You're listening to Draft Kings Network. of South Beach Sessions. John Lovett is a media mogul. I can call you that, yes. Uncomfortably, he doesn't want that. Crooked media, Pod Save America, love it or leave it.

How did we get here? I mean all of it. I don't mean not just conversational. I mean, you went from math, you stand-up comedy to something that isn't those things. So when I graduated from college, I moved to New York.

I was a temp 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. 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 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, are 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. 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 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 able to get some of that via stand-up, at least, you know, in the kind of cobbled together way you get some laughs at an open mic. I was able to get that in terms of like I had a got a good L-Sat 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,

Once after I got this junior position 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 spine to biffithet a charity. How does that happen? They had heard, I was working for John Corzine and his Senate office, it had, 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 stand-up careers amateur. And so they asked if I would write some jokes for Hillary Clinton. And so I got on the phone, 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 a, this was when he was just Al Franken, author, comedian, host of Air America Radio. And I wrote some jokes for Hillary

Clinton. That's 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 that the opportunity to be the speechwriter for Hillary had come along. And how did you decide not to go to law school? Like was that laborious, that decision? And disappointing to people who wanted you to go that, Pat. It was haphazard and quickly made. I had enrolled at the University of Chicago Law School and one of the reasons I allowed it to go on so long as 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 want to go. I never wanted to go, but it was just the thing to do. And it was the moment when they required a photo 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. 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 going up on Long Island, which is very kind of where I grew up in Ciocese at that time. It's very, very career-driven. What are you going to be when you're going to 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 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 want to be good at something. Right. 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 feel insecure, it just was easy to chase. Yeah, I also, I realize now looking back and maybe this is the same for you, But 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 even occur to me. Wouldn't even have occurred to me to defy the kind of direction, right?

Which was do your school work. Law and math. Law and 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. 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 going to go be free.

I'm going to be free in all the regards. I wonder, yeah, I'll let me know. I'll let you know when I do that. I wonder how it will feel. But you chose, I mean, professionally, you made some of the choices. When you go from speechwriter to know, I'm going to take the things that I loved about stand-up comedy and politics, I'm going to meld them and I'm going to make it uniquely me and love it or leave it. Yeah. I got very lucky along the way in that I, so I never felt like I was taking

risks, the truthfully. I mean, I didn't feel that way to me. So I get this opportunity to work in politics, so I take the job. I move to D.C. Then I get this opportunity to be a speechwriter for Hillary. I'm doing that for three years when I started working for Hillary. I started working for Clinton in 2005, this is before anybody had heard of Barack Obama because he had given the 2004 convention speech, but he wasn't a presidential candidate. She was the figure that was going to go on. And I thought, wow, I'm in this position. I'm going to get to be on 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 years of being a speechwriter. That wouldn't look like a risk either if you so badly didn't want to do it. Right. It just didn't make sense. Exactly. Like I just, and it wasn't as though I was, I had a job in politics.

And so when I decided to leave being a presidential speechwriter to come out. out to L.A. to be a comedy writer and stand up. 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 I, and now it sounds ridiculous to me, a love 12 years later, which is I had just turned 29 and I had this feeling that if I didn't leave and try comedy right now. I would never have been a young stand-up. 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 L.A. And I didn't have any money. I had just a junior speechwriter salary from the government.

And so I, 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 Correspondents 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, hey, you had 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 L.A. And I thought I was going to 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, though.

You did some work with the newsroom, and you did a show 16-100 pen. And you must have poured your soul into those things. Like, are those are dream projects? So this is where, and anyone listening to this, I know it's, so I, it's going to sound obnoxious. I moved to L.A. 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 own family, they had been kicking around this idea for a White House show. They knew it I'd worked in the White House. So we got together and we developed this pitch for Josh Gad to play this near-de-well 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. 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, on a pilot that was going to shoot. I had never written a pilot before. So I was, forget like a dream. I was overwhelmed. I was completely I didn't know what I was doing. 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 going to be doing this thing. You wouldn't have been overwhelmed by that. You would have dreamed 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 I, this is what, of course, yes, I had no, I, we, 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. I had no idea what I was doing. And then I get out to L.A., 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 going to be on television.

I've never written anything like this before. Is this imposter syndrome? Or you're saying, no, I was an imposter. No, no. For 1600 pen, imposter. I could fake it till I made it. I learned a lot. I could get through it.

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 any people knew how unsure I was, like the whole thing would collapse on itself. There was a moment where they had, because it was my first time working on a show, they had brought 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. 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, 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. It was highs and lows. I was like I loved being on set. I loved pitching jokes. I also feel really, like I, 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. And that was a group of people. They've all done on to be incredibly successful. And I feel proud of that because I feel like I, was, I had a good eye for this great group of people, all of whom have now really succeeded. And I, again, similar to, we talked about before recording, that, that, like, I felt like, like, you know what? I'm new here. I don't know what I'm doing. 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 were the scripts we're producing and I'm like really bringing value here and there's a reason I'm here and I'm making this project better and that felt rewarding that felt like okay I belong here 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 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. 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 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 you have to be able to say all right I my job here you know people would always ask me like oh you know you were gay and you were this

was before politicians were in favor of gay marriage that must have been hard and the truth this, it wasn't that hard because I never thought of it of my job as using speeches as a vehicle for expressing my opinions. My job was to inhabit the views and experiences 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 compare of 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 were part of my success as a speechwriter and then as a comte writer. Well, you say you're a fast writer and there are a number of different things I want to 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. So that doesn't sound like fast writing. That is a lot of curation for something that 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. We have, you know, let's say we have Tignotaro and her.

wife on the social Stephanie Allen and we want to figure out that segment or we have 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 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 a 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 punchlines, and just sort of going through it relatively quickly.

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, oh, I see what you're saying. Or, you know, the show is in an hour. We need three new punchlines for this. or the, we've, you're on set and you're trying to figure out how to make a scene work. Like, I'm, those are the moments where I feel like, you know what, like, I can, I can, I can come up with something pretty quick that'll work.

But you thought that was going to be your career then, right? Once you've gone into script writing, like where, where are you, when do you solidify? No, I know what I'm going to chase now. Never. I don't, I don't, I don't, I don't do that. I don't, I don't. It's, it's never, I've never thought that far ahead. Opportunities come, you take advantage of them.

You know, I had this chance to be a speechwriter. I took it, made the most of it. Had this opportunity to come out to L.A. 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, a TV writer, did 600 pen, wrote some pilots, worked on the newsroom. But there was this

pull to politics that I did feel throughout that time. The, the, and this is where I sort of would, 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. 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 to do this live stream. My car ran out of gas. We pushed it 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 what 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, 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 guerrilla outfit.

There's CNN. There's the 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. 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 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

think 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 needed to be there were activist groups and there were some left-leaning media organizations, but those two things were not intertwined. And 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 are, that we believe democracy is under attack right now. We are a pro-democracy, media company, unabashed. in that point of view, and we welcome anybody who wants to be a part of that. And we're not just going to treat people like observers the way mainstream media does, like kind of, that treats the viewers as if they're aliens watching the United States from spaceships. We're going to remind everyone that they are participants and that these are, that it's not a game, there are real stakes, and we all have agency. So we have to do something is an inspiration. It's anger. Anger is my

motivation. I'm never, 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 I I like there's been some nothing's bothered me more. No, a lot of things have bothered me more. 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.

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? It means you know what the right thing is, but you need

someone to tug at your heartstrings 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. 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 what 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. I need them to have it to persuade others. 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'd like to think I've moved beyond that. 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 it's 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 as path. More like you're kind of going from these islands, these little, 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 of thinking three or four moves ahead seems impossible. So I'm just trying to get to the next stop. Orr frames are the cheat code for winning the holidays, personal, easy, and

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Limited time offer. Where is your mind a blessing and where is it a curse? What a funny. Very, very, um, that's a very, uh, Barbara Walters in the 90s type question. Um, is it? I wasn't trying to bring Barbara here with us. 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 in my head. Yeah, I have a noisy mind. I am lucky to be, I'm very curious. I don't 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, I ended up publishing a math paper. I go into politics. I have 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 Potsay 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 of, that like I get curious and interested and intense about a certain idea or a certain project and I can really focus on that and then kind of can fully switch gears. Like 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. 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. And I, like, and so I, and the, the structure. of that, I would just get pulled in a bunch of different directions and I kind of put it aside, come back to it, 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'd 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. 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, just because it's sort of, I recognize some of what you're talking about here, and I crave a different experience with it, because when you said rewards, I was going to ask you, is one of the rewards happy?

Like, I mean, fulfilled maybe, but I'm just saying, like, I'm joyous while I'm doing. It seems like what you're doing now is so uniquely yours that 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, 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. I, 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, things are good. Things are happening in the country or 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 you, when life is tense or. I could learn from that. Like, I do not. I wish. I could say all of those same things in my daily statement. steps don't have that kind of gratitude in it the way they should. Same. I'm not, I'm saying

that's what I should be doing. I completely agree. Completely the same. But I do think for me, the pandemic was obvious, like, there's this F. Scott Fitzgerald series of essays called The Crack Up. Have you 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 book or long article. And it's an interesting document because he doesn't have the terms for,

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 he's writing lists to occupy his mind. and he and one of the 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 um but isn't that

great line right i mean yeah yeah the thing it's just snuffed by people who aren't better than i am in any way like and this is not merit based what 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 crack like a plate when I heard the news. And for me, the pandemic brought me low enough 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. a more than a decade-long relationship ended I 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 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 would look back on this and feel like I've still got plenty. I had more plenty of place to grow. Still not kind enough to yourself? I don't think so. Or to all that. Yeah, no, I don't think so. It's more too about like maybe you feel this too, which is like 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. That's what I'm like that, you know, that's it. And this is cooked. This part, this part is cooked all the way through. You put the fork in this part, it comes out clean. If ingredients and love or acceptance and understanding and that, like there's real wisdom.

and that. I'm good. I'm good with that. I'm about myself. Well, you know, this sort of in a kind of like self-help culture, I think too often, right? Like, it's hard because, um, some of us do you 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. 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, you know, cavemen can go about being formed and stuff. But I had, like, I needed some help being kinder to myself. I wasn't, even with the consciousness, I wasn't getting there myself.

And it's still a perpetual fight. But I absolutely needed nudges along the ways and all the blind spots I have around my insecurities. Yes, yes. And I also, for me, too, it's like a happy, 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? 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 and I remember when I was I was talking to my therapist about it and she was really funny She was like, you're going to go on this thing and all the ways in which you kind of obsessively self-criticized, they're just going to 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 going to stop finding ways to criticize yourself.

And I was like, maybe not. Let's find out. And the truth is like, the truth is it's somewhere in the middle, right? Like, it, no, of course, it's pessimistic. Well, but it is. Of your therapist, I'm saying like, well, she was her concern. It was that, it was like, hey, we should. She was not against my going on it.

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 going to address the work, which is correct. And I actually, 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. 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 going to net out with less self-criticism. Absolutely. There's all kinds of ways in which people... The math is useful there. So here, I'll give you, there's all, here's one. I'll give you, this is one which is, okay, I want you to imagine, okay, a X and a Y. On the Y, we have gregariousness. I'm sorry, on the X we have gregariousness. On the Y, we have charisma. Okay? Gragiariousness at the bottom, charisma going up and down. All right.

There's a diagonal line that runs 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 gregarious. You're exciting and enticing to be around. If you are extremely charming, okay, extremely charging, but very low gregariousness, you're extremely cool because you're just not giving it out. right right if you're extremely gregarious but not at all charming you're a bore and what you want to do

in your life is stay below the cool boar line above the core bore line you want to be above that line you want to be above that line gets distorted though by you know less fat less funding well that there's that challenge that is challenge i remember um when we were making 1600 pen uh Josh uh between the pilot and the shooting he was like he lost a bunch of weight and we were always joking that he's lost you lost like 15 pounds of hilarious it's unbelievable it's hilarious is all it's falling off of you it's not great for anybody involved no no 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,

It wasn't that what we were doing 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. 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, my God, look at.

this. I'm presiding over a writer's room that I have the ability to harm or help by my present, but it's mine. 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 I think taking too much

esteem from that is the wrong thing to care about. It's good. It's great. It's good. This team 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 like kind of

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 are you I will 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 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 in 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 on somebody said this like people always say like oh wow you guys have a lot of fun in those meetings. And we do. And that's to me when I feel the most joy. It's not like, oh, it's more like we're putting this 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, and there is. It can be all of these things.

I didn't say that, actually. that it's a thought process that could encourage arrogance, which I feel, which is why I fight it. You said it was unhealthy, and you made me think about, oh, can it be? 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.

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 a poison to me. I think it's a little kind of like, you know, Simba, everything, 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, do 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. I don't think anything wrong with any of this. I'm just, 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 tell you, I have trouble with the word yours. You oversee this thing that you've helped build.

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In the recent versions of South Beach sessions, we've been talking to my friends about really vulnerable things, and I cannot say that Tommy Vitor is my friend. And I can say that I have admired his story from afar because it seems crazy to me some of the stuff that he's done and the business venture that he has now embarked on, which is wildly successful, but probably comes with some trap doors that he never expected and the audience has no idea about. What do you view as the craziest parts of your story, your journey? The White House. The White House. I mean, I think so much of life and my, you know, career has been luck and timing. And basically, I graduated from college in 2002.

I interned for Ted Kennedy for a while on Capitol Hill. And I desperately wanted to get a job in his office to sort of like the front desk guy, you know, fetching coffee for people, like whatever it might be. And I didn't get hired. And I was completely devastated, but not getting that job led me to campaigns and to work for President Obama on his then Senate campaign in 2004. And that little piece of luck led all the way to the White House and sort of a completely improbable journey. Okay, luck, but also you view it as, oh my God, they're going to pay me to just

spend all this time learning about, like, secrets of how the world runs? Like, they're going to pay me to just learn. Yeah, that is what it was. I mean, so, uh, the first two years in the White House, I was a spokesman and a bunch of sort of general issues. The second two years, I was the National Security Council spokesman, which meant I handled foreign policy, national security, uh, things of that nature. And, you know, associated with that comes a top secret clearance and the ability to go to really interesting meetings, talk to really brilliant people that work in all parts of the government, the intelligence world, the defense department, state department, and help them or ask them to explain things to me so that I could explain them to journalists

and help people understand, you know, what Obama was doing when he went to Turkey or something like that. So, yeah, it was a hell of a job. But were you being aspirational or ambitious here with career goals in mind or were you just no I want to learn this is going to be fun to learn I think you know I was thinking about this today because I you know think about some of the questions for the show thank God we were so young and and stupid and almost didn't realize how much we didn't know by and when I say we I mean the people I worked with on that campaign because when you go from a political campaign to an administration, in a sense, you're prepared for it because you've been working, you know, 100-hour weeks and you know, Barack Obama's record inside it out and you have dealt with the press. But you're never actually prepared for the problems that you're going to face once you get into an administration.

You know, I was thinking about things like the Fukushima nuclear meltdown that happened in 2011. I mean, there's no preparing yourself or preparing yourself. a government to, you know, go into a meeting where someone says, hey, this nuclear reactor in Japan is melting down and we might have a Chernobyl-like event if the following things don't happen. So it wasn't ambition. It wasn't anything about my personal career track. It was sort of something that felt fun and exciting and there was a team of people doing it together and a shared mission and a shared goal and a really inspiring leader. And that just made it fun and rewarding. But how far are you now from whatever it is you were dreaming you were going to be?

I mean, in a sense, just a completely different place. You know, I mean, when I left the White House in 2013, I thought to myself, I've been on this, you know, Ferris wheel, this merry-go-round for about nine years working for Obama. I've been in politics for a little bit longer. It's time to step off. It's time to do something. else with my life, get away from politics, you know, move on from that, get out of D.C. And I tried. I did it for a couple years, but it didn't stick because here I am, you know, 2023, still talking about Joe Biden's record, still talking about Donald Trump, still sort of focused and obsessing

about politics every day. But, but, and also running a media empire with your friends, which is a totally different, it's a totally different thing than, I mean, I don't even know where your primary concerns are. But yes, I've focused on the things in sports that I focus on. And then I look up one day and I'm managing 50 people or I've got 50 employees or whatever it is. You have a sit. Your story is parallel here where I don't think that you ever imagined that. Did you? No, not at all. And well, I'd love to know what the experience has been like for you, but it started with three of us. Then there were six and then there were 20 and then they were 50. And then all of a sudden we realized management's a full-time job and there are people that are really, really

good at it and there's people who are less good at it. And I think, I don't know if the three of us would have been really, really good at it if it's been in the entire focus or not, probably not. But when you're recording a couple shows a week and you're touring and you're focused on all the political things we want to focus on, we realized we needed to bring in some folks who could manage the place full-time. So, you know, we had a CEO-O who really focused on the operations, the nuts and bolts of the place, and then recently we hired a CEO that's fully running the place and letting us, John, John and I, be more focused on recording shows. But I'm not sure how did you guys manage things from sort of no employees to many? With me, after shows,

very often walking into rooms, sitting in a chair, being close to sobbing and saying, I don't know how to lead. I know that feeling. I know that feeling. I know that feeling. too. I mean, or someone, I was talking to a friend, this guy, Ben Smith, who ran BuzzFeed News for a while and then started a company called Sem before, which is another media company now. And he said, the thing about having more than 50 people on staff is every week somebody is having the worst week of their year. And that sort of bleeds through into everything in your life, whether it's you or somebody on your team and you have to figure out how to help them or account for that or make things work despite of, despite what everyone's going through. So, yeah, it's been an enormous challenge. It's a full-time job. Our CEO, John Skipper, who used to be the most powerful man in sports, says it's a hell of a lot easier managing 10,000 people than it is managing 40 people

because of what you just said. Because if you're going to build a company that actually cares, that has a soul, and I want to talk to you about this, because you found a unique space in the media landscape, a really unusual place where you can be vulnerable and you can be. the other side to what seems to be having more success, which is right-wing stuff that's getting traction. And you're out here fighting a different kind of fight on the other side with facts and nuance and real expertise. But I along the path have felt really lost. And I don't know if you'd never considered the idea of running. Like when you're working for Bill Simmons,

it just seems like a magical job, right? You're just allowed to talk into a microphone and just show off your expertise, you go home and you're done with your work day. It's much easier than anything you've been doing before and probably more fun since you're doing it with your friends. Yeah, it was, yeah, I mean, what happened with Bill was John Favro, who is one of my co-founders here, went to Holy Cross, where Bill Simmons went to college as well. So they, like, got linked up many years ago, became friends, being friendly. John moved at the L.A. And Bill said, you know, what if you and one of your buddies came in and, you know, did a podcast about politics running up to the 2016 election.

So John and Dan Pfeiffer, and then John Lovett and I started doing a show called Keeping a 1600 a couple days a week. And it was a really fun hobby, but it was part-time. I was still living in San Francisco at the time. I would just kind of Skype into these calls. But slowly the show's audience really begin to grow and grow and grow. And then when the election happened and everything we thought was going to. going to transpire, did not.

Hillary Clinton didn't win. Donald Trump won states like Pennsylvania that Democrats thought were impossible to lose. We all felt this enormous sense of guilt and feeling like, you know, the things we cared about were too important to let them be a hobby and that we need to go all in and do this full time. And that's where crooked media was sort of born.

If Hillary Clinton wins, none of this exists? Probably not. I mean, it's a great question. I think about it all the time. Maybe we would have decided that there was still a place for a different kind of conversation about politics. We might have. But I don't know that we would have done it with the same urgency that led us to start crooked media right away to launch the shows in early 2017 for me to convince my now wife to pick up and move from San Francisco to Los Angeles. I think that would have been a little bit tougher.

Well, tell me some of this, right? Tell me about the sacrifices that people don't see when you're taking over a hobby, making it a job with your friends, but now comes also the pressure of, we're going to be activists here with facts that inform people, and we're going to believe that there will be nutrients that people will buy, and we will be able to create an economy that actually is a fighting machine. And it's going to try and fight with facts. Yeah, I mean, so there's definitely a recipe in sort of right-wing talk radio that you guys have watched forever from Rush Limbaugh to some of the, you know, Crowder folks who are on now that's very angry and divisive. And, you know, lots of demagoguing groups, especially LGBT people, people of color, right? I mean, you see this all the time. That recipe does not work on the left. I'm glad it doesn't.

I think the more progressive side is motivated by things being funny, inspiration, a more fact-based conversation. So that's what we wanted crooked media to be. We wanted to be a place where you could talk about politics that didn't feel like cable news, where it was like these stilted debates and the same talking points and the same people in these green rooms over and over again. There was a little more entertaining. There was a little deeper dives on the issues people cared about. But then, if we were talking about something you really cared about and you wanted to do something about it, we wanted to be the place that could help you figure out how. And there's no magic bullet.

You know, there's no easy answer when it comes to like solving some problem or, you know, making sure that our democracy is protected. It's sort of a day-by-day process of citizenship and voting and volunteering and donating. But we wanted to create that infrastructure to make it easy for people and also to make them not feel hopeless. Because I think the kind of demagogues win when people feel like, eh, politics is a waste of time. All these politicians are the same. What's the point you've even trying? You know, like that's, that I think is the worst thing that can happen to people like me

who think the government can be good and help people when done right. But if you're in a dirty fight and a corrupt fight, if you're in an ugly fight where the other side isn't fighting fair and you come to the fight with funny and inspiration, you lose those fights. Like, that's why what you're doing is tricky. It's why I admire that you, I mean, the downloads that you have are crazy. You have found an audience that not unlike you who chose the White House because you wanted to learn, because I don't want to skip past this part. I think it's important.

If you don't have political ambitious ambition and climbing that is now corrupting and contaminating all of government and you were just in government more, I shouldn't say just, but to learn, You take your ego and the ambition out of it. You got out of government what you needed, which is an expertise, and you listened. You weren't so interested in climbing or showing others what you knew that you had the foremost experts in the world, giving you free information all the time that you now use to have a thoroughly expert podcast. Thank you. One of the coolest things about getting to work on the national security side of the White House is there's this little. team of people called the National Security Council. And for under us, I think it was up to like 500 people who were on that staff. Almost all of them, very few of them were direct hires. A lot of them

were detailed over from agencies. So the CIA would send somebody over the Defense Department, the State Department. A lot of those people were career born service officers, career intelligence officers, you know, people who are in the side of politics or in the part of government that is not political. And so I never knew their partisan leanings. You know what I mean? I just knew that there was this really funny guy from the CIA who was in meetings with me a lot and would help me out when I needed answers about what was going on in Syria, for example. So it's just a really amazing window into government and sort of like the selflessness of the people that serve in it and aren't known, you know, don't make a lot of money, a lot of them

to deploy overseas to scary places sometimes and don't have to see their families, but are really, you know, they're in it for the right reason. So I saw like a much better side of government. than you see on, you know, Fox News or a cable TV show or what have you. You mentioned your wife and asking her about a pretty substantive life decision. I know I just know I wouldn't have done any of this. I wouldn't have left ESPN. I wouldn't have left comfort.

I certainly wouldn't have started a business if I did not have this undying ride or die support at home for the days when I come home on my hands and knees. So explain to me what your wife, who loves you, warned you about. working with your friends and taking on a venture that now has an enormous amount of responsibility on top of it. Yeah, I mean, I curious what you're, you know, what I told my wife, you know, so I left the White House, my friend John Favreau and I, we started a company that did a lot of speech writing and kind of like communications consulting work. It was it was a good job. We did pretty well. I liked a lot of people I met, but I wasn't totally fulfilled. Then we started doing the Keepin a 1600 podcast on the side. That was fun. It made.

me realized that I wasn't escaping politics, that I was so obsessed with it. And then when the election happened, I went to her and I said, you know, Hannah, we want to start a company, make this a full-time job, and give it a go. And I think, understandably, she was sort of like, do you really think podcasting is a full-time job, which, you know, in 2017, I think most people probably had that reaction. My in-laws, my parents, a lot of my friends. I mean, I don't know if you've encountered sort of. the same response.

I mean, I did with my family. It wasn't podcast. He was a million years ago, but the idea of writing sports and making any money for a living when your parents are exiles who fled to find freedom. And my father wanted me to be an engineer. Yeah, he didn't talk to me for a long time

because he... Really? I mean, I might as well have said, you know what I want to do? I want to be the lead singer of a rock band and do just a bunch of heroin. And also, they're not going to pay me anything for it. That cool? with you, Dad? Yeah.

But it's not as ridiculous. Your wife knows you. And this is why I said, I couldn't have done this without my wife, just couldn't have done it. She saw the ways that I was not fulfilled, and she wanted to push me toward happy to challenging myself, but something that was more rewarding, more fulfilling, while a lot of people also warn you, by the way, and I'm sure you got this, be careful about working with your family and friends, because it might cost you your family and friends.

I have a friend who did that. And he made a lot of money, made a ton of money, and it cost him all the friendships before he was 30 years old because that navigation can be very hard. I don't know how you've navigated it. I don't know how we navigate it either because we're not just business partners, but we also share the microphone a couple of days a week on shows. I think maybe the answer is, you know, every once in a while, you just have to scream at each other and fight it out and then get over it like a sibling. I do think it's more like brothers than friends or business partners at this point. What are the challenges you weren't expecting? Honestly, I think the challenges we weren't expecting were how hard management is, how much focus it takes, how much time, how much empathy and understanding, and how ill-prepared.

I think I was coming out of politics to do a lot of those things because, My job was usually as a spokesperson, you know, I went out to Iowa. I lived there for a year and ran the Iowa press operation for Barack Obama. I was the press secretary, another friend of my, Josh Ernest, who was later the White House press secretary, was a communication instructor. After that, they were like, you're doing rapid response. In the White House, I handled a bucket of issues, which is a long-winded way of saying, my job was like, here's a task, go sit at your desk for 12 hours and do it. You know, and I didn't rely on managing a lot of people or working with folks. I just sort of like did my thing.

And going from a place where you are focused like that and focus on one task every day to trying to oversee something bigger is really, really hard. How lonely was the job and forgive? I don't know you this way because I shouldn't be asking this question probably. But how much did it test at your marriage that you were doing? what sounds like a bit of a lonely job. And furthermore, your wife is saying, you don't seem fulfilled. Well, so I met Hannah in 2012.

So we were together for about a year and a half while I was at the White House. Her, she was definitely one of the reasons I wanted to leave when I did, which is in March of 2013, because I knew that I couldn't focus on her and our relationship as much as I wanted to if I was, you know, in this full-time job. So it wasn't lonely in that we had a team of people and it was kind of rag-tagged that all did the campaign together and then went into the administration.

So we really did have that kind of like band of brothers like group of friends, sort of shared misery, shared triumphs together that kept you sane. But there were definitely days where you're, you know, you're there after a really long day or it's a late Friday night or Saturday morning or something like that, and you're still at the office and you're just like, this sucks. Oh, but yeah, but what you're talking about there, though,

the emotional bandwidth that you're giving, you're saying, yeah, Triumph and you, you, and the feet of the job, and hooray, and this is so invigorating. But what do you got when you get home? Because you're not going to have a whole lot left in the tank. If that's what you're giving your job, like it's hard to, I mean, I don't, I have spent two years telling our employees, get me home to my wife please get me home to my wife i want to be there because it's so hard to do

both yeah and listen it recently i realized how hard it was because we uh we just had a baby she's almost six months old and if i don't get home before six i don't see her that night you know because she goes to bed at like six six 15 or six 30 so that's become a real pull uh that has that gets me the hell out of here and makes me think back to all the people I worked with at the White House who had kids at home at the time and were stuck late day after day after day and just never saw them. I just can't imagine doing that job now.

How did Hannah know that you were not fulfilled? And what are the differences in you now? Because it sounds like you've got like it sounds like this is the happy lane. Yeah, this is definitely the happy lane. I mean, I think Hannah knew, so we're living, we moved from D.C. to San Francisco. I was doing this consulting job with John Thavro and a couple other folks, but I was doing it remotely from San Francisco. So I was just working from my house. And she would leave and go to work and come back.

And I would just sort of still be there and hadn't really had any human contact all day. And that just did not work for me. I am a person. I'm a social animal. I need to see people. I need like water cooler talk, just something, some sort of distraction. And being home alone all by myself in our apartment. for a couple years, broke my brain.

And so I think she knew that, yes, I desperately wanted to try to create this media company to fix the way politics has talked about in the country. But also, I needed to get the hell out of the house to be around people again and do something like that had a team element because I just missed that so much. Hannah did not marry a puppy. That is not something that she married. She married somebody who has a puppy who has to interact with other puppies. So what do you say that?

Because she would literally, she would come to the door after work and come home. And I would greet her at the door. And she would be like, you greet me like you're a puppy. Like you've got to get out of the house, man. But you've been doing hard and noble and admirable work. So how much fear was there for you in the transition as you're looking for support on something more fulfilling? I mean, you know, we just figured we went from having a show that had gained. some popularity during a crazy election to restarting everything, you know?

So your subscriber count goes down to zero. You have no idea if people are going to want to listen to this show again. Now that Donald Trump is actually president. So there was a lot of fear, like, will people tune back in? Well, do people still care after this election happened? Or are they going to give up and tune out? So there was a lot of that. And then there's just a constant imposter syndrome.

Like, why the hell would anyone listen to us when there's a million other options of? you know that that's a day-to-day thing so why make the bet make the bet because um deeply felt guilt about having been so dedicated to politics and then pulling myself out at a moment when it felt like um i should have stayed in and feeling like the conversation about politics in the 2016 election was as bad as it had ever been because all people cared about was the horse race and the games, and they didn't talk about the stakes and the impact on people's lives and why it mattered and how we all need to get involved. And we wanted to try to move the needle on that conversation and make it a little better. Was progress for you

in terms of putting down fear and doubt and getting confidence linear? Or were there many times early on where it wasn't what you are now, which is clearly a radiant human being doing exactly what he wishes to be doing with his life and fighting this fight the way he wishes to be fighting it. I mean, I swear to you, I'm not joking when I say this. Every time we do like a live show or a podcast and we walk out on the little stage thing, I'm sort of like waiting for there to be no one there. You know, that's just a constant imposter syndrome, wondering when the audience is just going to go away.

I think part of that is just anxiety, but part of that is, I don't know, maybe a healthy fear that keeps you hungry. I don't know. What about you? You guys, like, the media industry, especially for sports, is changing constantly. The big players get pushed around a little bit. I mean, like, how do you guys deal with that? There's upstarts. There's barstool.

There's ESPN. I mean, there's just like competition everywhere. Yeah, I'm not competitive that way. So that's not where regret or doubt would seep in. It's on the hardest days when I feel like managing of people is hard and I never, never envisioned myself as any kind of manager of people. I've always been responsible. It's just self-sufficiency. Me, the microphone, do what it is that you do.

You don't have to. It'll take care of itself. Your worry of others, the economy around this fun thing will take care of itself. But I had reached a point at ESPN where I couldn't keep eating silent. when I'm freedom first, voice first, and I'm too much about I've got to be able to speak freely. And so the musling was a different kind of unfulfilling. It was too much of a sacrifice of principles that I couldn't abide. I couldn't look myself in the mirror if I was living in a space where I had to sell out that, obviously,

like sell out in a way that I couldn't come up with a rationalization when I was looking in the mirror for what my family's about. And so I just I had to do it. And then it came with when the discomfort arrived, what it felt like was just unsafe because it's not regret, but it's just like, oh, my God, I could have been cashing checks talking into a microphone for millions of dollars if I had just kept my head down, but not been able to live with myself. Yeah. Do you think the ESPN brass regrets trying to muzzle people? It's so much more interesting when you don't muzzle people, no? at Disney that was a question

I just don't think I don't think that they want the headline why would they want the headlines around a sports program of sports host goes after Trump like what do they need that for it's a little bit easier to just hire Pat McAfee give him $17 million a year and he's probably not going to do that

yeah all right that's fair but I mean I don't know it seems like there's some really interesting people like saying their thing, you know, like the whole stick to sports, shut up and dribble, LeBron, get out of politics. Like, I don't know that that worked too well for his critics.

You tell me what value people in sports have for all of this stuff, because I've found that it's safer and more rewarding, generally to just stick to sports. You won't lose sponsors. Like, I'm not saying that that's what anybody should do, but if you just stick to sports, you're not going to, man, I don't want to be trusting. bud light from my moral compass like i don't want to have to worry about what they're dealing with

in their meetings so that i can say this or not say that like i how much politics do you see with your sports you know it's hit or miss you're right listen obviously just from a purely financial standpoint uh you can probably identify a few topics that if you never touch no one will criticize you um i do think there are people that get involved um in in in politics and sports like the Rooney family that I think have done really well by themselves by seeing sort of like principled leaders in a couple of different areas. But, you know, I hear what you're saying. I mean, it's certainly more complicated. And the Roonies are foremost leaders on racial matters. This is the funny part about what it is that you're saying. I don't even think

that I talk politics. What I've been talking about for many, many years has been race and it gets hijacked. It gets turned into politics when all I feel like I'm doing, and I'm now viewed, I'm called Lib Tard and Woke, the Cuban community will call me gusano worm for being a traitor against the politics of my region here in South Florida. But all I think I've ever advocated for, which is now somehow a controversial position is, how about equality and decency for all? Like that's why I'm politically, I mean, I'm guessing many people who are. on the other side of this, they're saying, no, you're an asshole, you're obnoxious, you're strident, and you're way, way left wing. But I believe I'm only somebody who says, can we be

decent to everybody? I don't even care about politics. Yeah. Well, and what you're saying is essentially what a lot of athletes were saying who are, who are silenced or shut down or told to stop kneeling, which is they were more specifically saying, hey, we want to prevent police brutality against black people. And that was twisted as sort of a political statement and people were told they were being woke or sick to sports or whatever it might be when really it was just about equal treatment of everybody. I'm so disappointed though, Tommy, that that works somehow. Like one of the things I was always saying to myself, I think I said it publicly,

I know I was saying to myself privately, if you're a corporation that has as much money as X, whomever it is, if you have FU money, why would you never say FU? Why would you never choose a side and say F you? Because you've got to make more FU money to never say FU? You mentioned the joys and sufferings of having a sleepless six-month-old in the house. When you welcome a child into the particular America that you're welcoming that child into as you're fighting for things, what's the stuff that keeps you up at night about the future? there was another mass shooting the other day I couldn't even tell you which one it was because there are so many of them and it was the first time I turned to Hannah and said I could imagine us living in London or somewhere else so that we don't have to deal with this shit that's what changes with a child correct because there are all sorts of fears about climate change and democracy crumbling but guns and the randomness of it when you

care about something i'm imagining the way you've you've never cared before correct yeah i mean suddenly you're kind of all the cliches are true your your heart is on your sleeve uh you're not in control anymore of you know your own uh your own soul um you know and it's it's two things it's the randomness of gun violence and the trend of uh these shootings happening in schools including elementary schools and also just the absurd reality that the United States has more guns per capita than any other country. I think the second biggest is Yemen, which has been engulfed in a civil war for the last, you know, however many years. And the inability or refusal of the Republican Party to just do some common sense things to get machine guns off

the street. I mean, it's, it's maddening. How have you been changed by the birth of your daughter beyond the ways that you're articulating here? before we had our daughter before we had was that I was not like a big baby guy you know you have a friend who had a baby they'd be like oh you want to hold them you want to hold her again no I'm good they're kind of scary like holding a three month old they just feel you feel like you're going to drop them that has completely changed for me I love every second with her you know I want to be around her all the time I think about the future in different ways than I ever did before It's also true that it was, it was, we had a hard time having kids. We went through several miscarriages. We actually had another daughter who was still born at six months and just sort of like the most devastating thing you could imagine. And so it has made me, being with her makes me more present and I think more self-aware of what a gift she is and how many parents. Parents of 20-year-olds probably think what I would give for another day with this son or daughter as a six-month-old where, you know, I could just hold her in my arms and she can't argue with me or tell me I suck or whatever it is we do once we're teenagers.

You have talked very publicly, vulnerably about those difficulties. Why do that? Roy Bellamy on our show decided that he needed to do that for some healing. I don't think people. understand, I don't think people talk enough about or understand the difficulties you're talking about there. Why did you decide to share that vulnerability with the internet? Yeah, you know, I mean, so Hannah and I went through several miscarriages. We did not talk about those publicly, but privately they were all consuming. And it impacted every night we went to bed, every conversation we had every morning we woke up there was just like sadness everywhere and so I think for Hannah you know in particular there was I don't want to speak for for both of us I think there was a sense of um embarrassment and shame and tragedy where for some reason you don't want to

talk about these things or you feel like a failure or you blame yourself in some way and all of that is irrational and stupid but then when um you know we lost our daughter margot So at six months, people knew we were pregnant. There was no hiding it. There was no way to keep this a secret. And I didn't want to because I just sort of couldn't walk around all day thinking about one thing and putting up a brave face and talking about another. It was just not, it was not an option anymore. And I also think that miscarriage and trouble having children is such a common problem.

but for some reason people don't talk about it. And I don't really understand why. I think that makes it harder on everybody. It makes it this sort of private, lonely tragedy rather than an opportunity to have empathy and share an experience with other people. And we both just decided like we got it. We just can't keep this to ourselves. I don't think of you in many ways or your work as irrational and stupid. So what is happening there that you are succumbing to a rational and stupid?

comparison ruins everything in life. You know, I think you feel like it's your job to, especially for women, this is particularly hard for women, I think, that your job is to have a baby to raise a child. And you feel like a failure if you have not. I know this is how Hannah felt. And on top of that, you know,

once you start to focus on these things or want to have a kid, it's all you see everywhere. friends, your peers, your coworkers, Instagram, you know, people with their new babies. And you compare yourself to them. And it makes you feel worse. And so I think that is where the irrationality and stupidity of it all comes from. The sort of the self-blame and criticism for something that's really out of our control. And how much joy is there now as a family that it would appear? I don't think I have this wrong.

that daddy has arrived at his wildest dreams. And now from a happier place can take care of a family, a company, and a wife. Because what you're articulating, you don't need to necessarily care about if you're building a cold company. What you're articulating about the managing of people is that crooked media simply will not be a caring company. if you personally don't care about the people that you're managing. Yeah, I mean, it, you know, it's an incredible place with incredible people who are well-meaning, who care about a mission, who want to be part of something that hopefully in even just a small way can chip away at some of the problems this country has and make things a little better,

can, you know, stand up for communities that are, that are getting treated like punching bags by the far right and to try to push the Democratic Party to do more, to help more people, to win more elections and do the right thing. And so we are incredibly proud of this place of the team that works here of the work we do. And, you know, it can feel like a family, you know, in the office, too. What a joy, though, right, to feel like you're in the middle of a fight, but also that you're laughing, entire time, right? There are also tears and frustrations and everything else, but I imagine that the joys of laughing about where you've arrived with your friends, my guess is that it's a combination of overwhelming and breathtaking. Yes, it is. I mean, like, sometimes the things

feel insurmountable, right? I mean, like, what can we, a little podcast company in LA do to, you know, change the course of an election or change the way the political system works or, you know, some of the entrenched interests that are run things. But it's enormously fun and rewarding to be part of a scrappy small team that's going to work like hell to see what they can do.