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
Chapter 1: How did Jon Lovett transition from math and stand-up comedy to politics?
Kings Network. Hello and welcome to the West Coast edition of South Beach Sessions. John Lovett is a media mogul, I can call you that, yes? Sure. Uncomfortably, 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? 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 felt right. It still works. Yeah, it works for the time. Yeah. How did all of this happen? And when I ask this question, I say, you were gonna do standup comedy. You were gonna 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. 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 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 uh like charm my way out of not knowing something and you can't do that in math you have to really understand it and if that logic and rigor really forces you to use your 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 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 math.
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. 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.
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Chapter 2: What inspired Jon to become a speechwriter for Hillary Clinton and Barack Obama?
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... 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 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... 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.
And- Not talking to anybody, not just, 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 growing up on Long Island, which is very kind of where I grew up in Syosset 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.
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Chapter 3: Why did Jon Lovett decide not to go to law school?
You did some work with the newsroom and you did a show, 1600 Pen. And you must have poured your soul into those things. Those are dream projects? So this is where...
And anyone listening to this, I know 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 Miter and Family, 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 ne'er-do-well son of a president. And it just worked and NBC wanted it. And so within days, 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, 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 overwhelmed
I didn't know what I was doing. So this is not... 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 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... I... 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 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 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?
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Chapter 4: How did Jon Lovett move from politics into television writing?
It was Jon 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 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 Crooked 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 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. 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 thinking about what the company would be called. We really didn't have much. We knew we were gonna 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. 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 it's not a game, there are real stakes, and we all have agency.
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Chapter 5: What challenges did Jon face while working on TV shows like 1600 Penn?
Where is your mind a blessing and where is it a curse?
What a funny – very – 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 – of the illusion of control, but it's like, I, I really would like it all to slow down in my head. Yeah. I have a noisy mind.
Uh, I am lucky, uh, uh, to be, I'm, I'm very curious. I don't find myself, I find myself interested in the ways in which, uh, 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 Pod Save 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, I do think I've paid a price for not being able to quiet that noise.
And there've 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. falls into chaos because both sides declare victory and I was writing that in 2014 2015 like it was a head I was like I was I had and I just couldn't get it right and I like
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, 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.
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Chapter 6: What skills does Jon Lovett believe are essential for a speechwriter and comedy writer?
Making a list of it. 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. Um, uh, a more than a decade long relationship ended. I, over the course of the pandemic had become a little too comfortable using, uh, 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, uh,
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, uh, wiser at the end of that. I'm sure I will look back on this and feel like I've still got plenty.
I had more, plenty of, plenty of place to grow. Still not kind enough to yourself? I don't think so. Yeah, no, I don't think so. Um, it's more too about like, maybe you feel this too, which is like, as you get older, um, 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, you know, that's it. And this is cooked. This part, this part, this part's 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 in that. You have to do that. I'm good with that 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 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.
But, and also loving yourself in there. Like I'm telling you, 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 needed some help being kinder to myself. Even with the consciousness, I wasn't getting there myself. And it's still a perpetual fight.
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Chapter 7: How did the Crooked Media network come to be after the 2016 election?
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 bore line. Above the core borderline.
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, there is that challenge. That is challenge. I remember when we were making 1600 Pen, 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. The 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 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 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
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Chapter 8: How does Jon Lovett view inspiration and anger in politics?
There's just gonna be some pressure dials. It's okay. There's going to be moments of tension between everybody. That's okay. But you're going to walk through 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. We don't all see things the same way. We've had our conflicts over the years, but...
You know, we ended up years later going through, we took on investors and we were working through the paperwork, right? A lot of paperwork. And there were 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 for what happens if we start disagreeing and like, don't worry about that. Like we will have each other's backs. We never need to worry about that.
And I think that's been a really, like underneath all of it, like 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, 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? 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. But people will tell you, don't do that. 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 going to spend all day working with somebody, you know, you've seen them all day. It's different.
You're not going to, you know, you're not going to like, you know, you're going to, you have a work relationship and you spend already a ton of time together. It's just going to change your dynamic outside of work. That's like, 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 who you see each other after work a couple of times a week or a couple of 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 bad thing, but just it is gonna be a change.
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Chapter 9: How does Jon manage his mind and the challenges of overthinking?
Like, cause 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 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 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.
And- 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, it's- You have really good people that are doing a great job, but you don't feel like you've done enough 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, I like being busy. To go back to where we started, I have a very good relationship. 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 going to go back from here, run back.
We're going to meet to talk about a design thing with this incredible designer who runs our design team. Then I'm going to meet with the Love It or Leave It team to plan a bunch of stuff. Then I'm going to meet with the politics team to talk about what we're doing with Vote 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 who just get together and brainstorm funny things we could do.
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