South Beach Sessions - Jon Lovett

Summary

Podcast Summary: The Dan Le Batard Show with Stugotz Episode: South Beach Sessions - Jon Lovett
Release Date: May 1, 2025

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Introduction

In this insightful episode of South Beach Sessions, hosts Dan Le Batard and Stugotz engage in a profound conversation with Tommy Vietor and Jon Lovett. The discussion delves into Tommy's multifaceted career, his transition from mathematics and politics to media and comedy, the founding and growth of Crooked Media, and the personal challenges he has navigated along the way.

Tommy Vietor’s Early Years and Academic Pursuits

Tommy Vietor begins by reflecting on his academic background, emphasizing his deep connection with mathematics and its influence on his critical thinking skills.

• Mathematics and Critical Thinking:
  [02:21] Tommy shares, “With math, you can't fake it, and you almost can't get it. You either get it or you don't.” He credits mathematics with making him a "more critical and precise thinker."

• Struggles with Society's Approach to Math Education:
  [05:25] Tommy criticizes the traditional math curriculum, stating, “Every school is getting it wrong.” He advocates for a more engaging and enjoyable approach to teaching math, believing it would lead to a smarter and more satisfied society.

Transition to Politics and Media

Tommy recounts his journey from academia to the political arena, highlighting the serendipitous nature of his career path.

• Venturing into Politics:
  [07:13] After graduating from Williams College, Tommy moved to New York, juggling odd jobs while exploring interests in stand-up comedy and politics. His involvement with the Kerry campaign in 2004 marked his initial foray into the political world.

• Becoming a Speechwriter:
  [08:46] Tommy describes how writing jokes for Hillary Clinton led to a junior speechwriter position. He reflects on the rapid shift from deciding against law school to embracing a career in political speechwriting.

From Speechwriting to Media Entrepreneurship

Tommy details his pivotal decision to leave politics for media and comedy, culminating in the creation of Crooked Media.

• Risk and Opportunity:
  [14:03] Transitioning from a stable job as a speechwriter for Obama, Tommy took a significant risk by moving to Los Angeles to pursue comedy writing without a clear plan. He shares, “I had to get out before I turned 30,” highlighting the urgency behind his career shift.

• Early Media Projects:
  [15:48] Upon arriving in LA, Tommy quickly engaged in media projects, including developing the pilot for 1600 Penn. Despite initial overwhelm and challenges, he successfully navigated the complexities of TV writing.

• Founding Crooked Media:
  [27:08] In the aftermath of Donald Trump's election, Tommy and his colleagues felt compelled to create a proactive media platform. Crooked Media was born out of a desire to support democracy and engage actively rather than passively observing political shifts.

  • Mission and Values:
    [28:04] Tommy articulates Crooked Media’s mission: “We believe democracy is under attack right now. We are a pro-democracy media company, unabashed in that point of view.”

  • Lean Startup Approach:
    [49:26] Emphasizing financial prudence, Tommy explains, “We never had to take investment, which meant we never had debt or shareholders breathing down our neck.” This approach allowed Crooked Media to grow organically and maintain control over its mission and values.

Challenges of Scaling and Maintaining Friendships

As Crooked Media expanded, Tommy discusses the complexities of maintaining personal relationships and company culture.

• Balancing Friendship and Business:
  [54:19] Tommy acknowledges the challenges of working closely with friends, noting, “If you spend all day working with somebody, you've seen them all day, it's different.” He emphasizes the importance of open communication and trust to navigate these dynamics.

• Managing Rapid Growth:
  [58:05] Scaling the company from a small team to over 100 employees introduced new operational challenges. Tommy highlights the difficulty in maintaining the company's voice and ensuring consistent quality across a growing number of shows and platforms.

• Unionization Efforts:
  [73:31] The podcast touches on negotiating unionization, a testament to Crooked Media’s evolution and commitment to employee welfare. Tommy reflects on the importance of building a collaborative and trusting culture during rapid expansion.

Personal Reflections and Mental Health

Tommy opens up about his personal struggles and growth, offering a candid look into the mental toll of his career transitions.

• Dealing with Insecurity and Validation:
  [07:13] Tommy admits that his early career decisions were driven by insecurity and a desire for external validation. Over time, he learned to align his career choices more closely with his passions rather than seeking approval.

• Impact of the Pandemic:
  [39:38] The pandemic served as a turning point for Tommy, prompting significant personal changes. He shares his experience with depression and how it led him to prioritize what he wanted to be doing over what he wanted to be.

• Balancing a Noisy Mind:
  [34:34] Tommy describes himself as having a "noisy mind," which fuels his curiosity and diverse career path but also presents challenges in maintaining focus and managing personal well-being.

Maintaining Company Identity and Vision

Tommy discusses strategies for preserving Crooked Media’s mission amid growth and diversification.

• Ensuring Consistency and Creativity:
  [60:28] As the company expanded, Tommy emphasized the importance of maintaining a consistent voice while also allowing creative input from new talent. He believes in balancing conformity with consistency to uphold the company's core values.

• Hiring and Building Teams:
  [52:18] Tommy takes pride in Crooked Media’s hiring process, noting, “I've read a ton of material, and that was a group of people they’ve all gone on to be incredibly successful.” This selective process has been key to assembling a talented and cohesive team.

Conclusion

Tommy Vietor’s journey from a math enthusiast and political speechwriter to a media entrepreneur encapsulates the essence of adaptability and resilience. Through founding Crooked Media, he has leveraged his diverse skill set to create a platform dedicated to pro-democracy values, all while navigating the complexities of personal growth and professional scaling. His candid reflections on mental health and the challenges of maintaining personal relationships within a growing company offer valuable insights into the human side of entrepreneurship.

Notable Quotes:

• "With math, you can't fake it, and you almost can't get it. You either get it or you don't." — Tommy Vietor ([02:21])
• "We believe democracy is under attack right now. We are a pro-democracy media company, unabashed in that point of view." — Tommy Vietor ([28:04])
• "Anger is my motivation. I'm not a hope guy, I'm an anger guy." — Tommy Vietor ([31:00])

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This comprehensive summary encapsulates the depth of the conversation, highlighting Tommy Vietor's professional trajectory, personal challenges, and the foundational values of Crooked Media. It provides listeners with a clear understanding of the key discussions and insights shared during the episode.

Transcript

[John Lovett]

You're listening to DraftKings Network.

[Tommy Vietor]

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[Jon Favreau]

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[Tommy Vietor]

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[Jon Favreau]

And brought the original Cool Rush scent.

[Tommy Vietor]

Back exactly how it was.

[Jon Favreau]

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[Tommy Vietor]

So grab some and remember why it.

[Jon Favreau]

Cool, crisp and fresh scent made it the number one men's antiperspirant for the last decade.

[Tommy Vietor]

Degree Cool Rush is back, and it.

[Jon Favreau]

Smells like victory for all of us.

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[John Lovett]

Hello, and welcome to the west coast edition of South Beach Sessions. John Lovett is a media mogul. I can call you that? Yes, comfortably. 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 standup comic? Is that a great name? Or.

[Tommy Vietor]

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.

[John Lovett]

Yeah, it works for the time. How did all of this happen? And when I asked 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.

[Tommy Vietor]

Maybe we'll find out together. But the I. So I grew up in New York. I went to Williams College, a small liberal arts college. I studied math. I studied psychology and philosophy. I loved 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, like, charm my way out of not knowing something. And you can't do that in math. You have to really understand it. And that logic and rigor really forces you to use your mind and concentrate. And I found it made me smarter, and it made me a more critical and precise thinker, and I really like that. But I was never. I was always the math student who could give the funniest presentation, but I was never at the level of some of those other kids that went on to become professors.

[John Lovett]

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.

[Tommy Vietor]

I really hate. I hate that everyone says they hate math. And I don't blame the people who say it, because I believe you. I understand why.

[John Lovett]

I'm just not good at it.

[Tommy Vietor]

But see, none of that. There's something fundamentally wrong. This is a conversation for another day. But there's something fundamentally wrong with a society. As a society, we take kids, they spend more than a decade learning this subject, and most of them get to the end of it saying, I don't like this. I am not good at this. So is everybody wrong? It's the most common thing you ever hear. If you tell people you studied math, they go, oh, I hate math. I'm not good at math. So every school is getting it wrong. Like, every kid in every classroom, in front of every teacher, they're all getting it wrong. They're all like, so something is totally out of whack. It would be. I think it would be a better society if everyone got to the end of high school and maybe they learned less math, but they enjoyed it. They got something out of it. They came away with something to upset you. No, but it's. No, but speaks to something important about where we're at right now. And because it's one of those, I don't know anything about baseball, I'm jumping around, I don't know anything about baseball, but I know what baseball bats look like. We all know what baseball bats look like. And then some guy working for the Yankees stares at baseball bats for a year, and he says, I think baseball bats are wrong. I think the little chunky bit should be a little bit further down. And they hit a bunch of home runs.

[John Lovett]

Basketball, you can do this with basketball. They were taking the most inefficient, least valuable shot near the rim. And then they all figured out, wait a minute, three points is worth more than two.

[Tommy Vietor]

Right? And we have this system where most People come out of math, they won't retain anything. Could you do an algebra equation right now? If I put it in front of you? And people are kind of enumerate in the most important skills that they should have as an adult. The skills that you need to understand investing, taxes, loans, credit cards, come away with none of those skills. Yet kids spend years sitting in front of teachers looking at graphs and algebra and all the rest. Imagine a math curriculum. It would be easy. Make it fucking easy and make it fun and easy. Whatever you were gonna do for three years, whatever you gonna do, take the first chunk of it, spread it out, spread it out till everyone gets it. And then everyone comes away like, oh, I loved math. It was so much fun. What a better world that would be.

[John Lovett]

How did we get here? And I mean all of it. I don't mean not just conversationally. I mean, you went from math yet stand up comedy to something that isn't those things.

[Tommy Vietor]

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.

[John Lovett]

Dreaming of being what though, at that point, are you still searching, dabbling in several things you like.

[Tommy Vietor]

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 had gotten into the law school I wanted to go to, that could have been in politics. I think I wasn't. It was. I was really not thinking clearly about what I enjoyed doing, what I cared about in terms of, like, what my passions were. I was so much more focused on external validation. And I was 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 LSAT score, I was on the right path to go to a great law school. And then I saw this path in politics. I loved the West Wing and I thought, oh, maybe I'll become a speechwriter. Right? That was something that was in my mind. And six months after I got this junior position as a press staffer in the Senate, this opportunity came along to be a junior speechwriter for Hillary Clinton. I jumped at it in part. I was there because I had actually written some jokes for her. She had gone to was supposed to go to a roast. It was the roast of Barbara Walters to raise money for a spina bifida charity.

[John Lovett]

How does that happen?

[Tommy Vietor]

They had heard I was working for Jon Corzine in his Senate office. It's a little, you know, not a lot of funny people on Capitol Hill. People had heard that I had done this barest of stand up careers, amateur. And so they asked if I would write some jokes for Hillary Clinton. And so I got on the phone with the Hillary Clinton 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 comedian, not a comedian. No, no, no. It was before he was even. This is 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.

[John Lovett]

How'd you decide not to go to law school? Was that laborious, that decision, and disappointing to people who wanted you to go that path?

[Tommy Vietor]

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 is it didn't require a deposit, which they should change. There was no deposit. So I was able to say I was going. And it wasn't until I had to email. I think the truth is, in my heart, I didn't 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 literally started. I was like, I can't do it, I'm out. I withdrew.

[John Lovett]

Not talking to anybody this doesn't feel right. I'm going with intuition here.

[Tommy Vietor]

Yeah, that's right.

[John Lovett]

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?

[Tommy Vietor]

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 a 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. 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.

[John Lovett]

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. Like, 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.

[Tommy Vietor]

Yeah. I also, I realize now, looking back, and maybe this is the same for you, that it wasn't as though I was choosing one direction over others or that I was afraid of being rebellious or afraid of trying something else. Wouldn't have even occurred to me. Wouldn't even have occurred to me to defy the kind of direction. Right. Which was, do your schoolwork. Law and math, get good grades. Law, math, right. It was like I just. I was not. It wasn't that I felt obliged to follow the rules. It wouldn't even have occurred to me.

[John Lovett]

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.

[Tommy Vietor]

I wonder. Yeah, let me know. I'll let you know when I do that.

[John Lovett]

I will.

[Tommy Vietor]

But I mean, I wonder how Will felt.

[John Lovett]

But you chose, I mean, professionally, you made some of the choices. When you go from speechwriter to no, I'm gonna take the things that I loved about stand up comedy and politics, I'm gonna meld them and I'm gonna make it uniquely me and love it or leave it.

[Tommy Vietor]

Yeah, I Got very lucky along the way in that I. So I never felt like I was taking risks, truthfully. I mean, it didn't feel that way to me. So I get this opportunity to work in politics. So I take the job, I move to dc, Then I get this opportunity to be a speechwriter for Hillary. I'm doing that for three years. When I started working for Hillary Clinton in 2005, this is before anybody had heard of Barack Obama, or I'd just 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 gonna go on. And I felt, wow, I'm in this position, I'm gonna 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.

[John Lovett]

That wouldn't look like a risk either if you so badly didn't want to do it.

[Tommy Vietor]

Right. It just didn't make sense. Exactly. 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 to LA 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. And now it sounds ridiculous to me 1112 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 standup. I would never have done it. And so I had to get out before I turned 30. I set this artificial deadline and I left and I moved to la. And I didn't have any money. I had just a junior speechwriter salary from the government. And so because I had this pedigree, I'd been working on both serious speeches for President Obama and I did a lot of his comedy writing. When he did the White House 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 la. And I thought I was gonna come out here, learn how to be a screenwriter, do stand up again. I did a little bit when I moved out here.

[John Lovett]

You did some work with the newsroom and you did a show, 1600 Penn. And you must have poured your soul into those things. Like are those. Those are dream projects.

[Tommy Vietor]

Like, so this is where. And anyone listening to this, I know it's so I. It's gonna sound obnoxious. I moved to LA and the first before I'd even had any sense of what I was gonna do. This Josh Gad, who was then in Book of Mormon, Jason Weiner who had directed the pilot of Myron Family, they had been kicking around this idea for a White House show. They knew 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 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 like imagination didn't have time to catch up to what was happening before I'd even gotten my bearings about what I would even want to do. I was working on a pilot that was going to shoot. 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.

[John Lovett]

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 gonna 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.

[Unknown Sponsor]

Right.

[Tommy Vietor]

But this is. I. This is what. Of course, yes, I had no. 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, 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 gonna be on television. I've never written anything like this before.

[John Lovett]

Is this imposter syndrome or you're saying, no, I was an imposter syndrome?

[Tommy Vietor]

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 people knew how unsure I was, 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 in an outside writer to do a rewrite of the pilot. He had a different sensibility. It just didn't work. And so now we're, like, days away from shooting, and I'm just in this script trying to fix it. I've never done any of this before. We ended up and figuring it out with Jason and with Josh and with some help from some other writers, but it was a very. It was more stressful than it was exciting.

[John Lovett]

So it was a project, not a dream project. Like, you liked it. Like, the idea of it's nice, but the doing of it sucked.

[Tommy Vietor]

It was highs and lows. I loved being on set. I loved pitching jokes. I also feel really, 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 gone on to be incredibly successful. And I feel proud of that because I feel like I had a good eye for this great group of people, all of whom have now really succeeded. And again, similar to we talked about before recording that, I felt 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. These. 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 we're. 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.

[Jon Favreau]

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[John Lovett]

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.

[Tommy Vietor]

I don't know. We'd have to start a pretty long list. No, I don't know. I feel, I think being a speechwriter, you don't have to be the best at anything, but you have to be competent or good at a lot of things. You have to have a good kind of sense of politics. You have to be a good writer. You have to be able to synthesize a bunch of different points of view and inputs. And you have to have the ability to know when to say yes, but or to say no, but to an edit a change a suggestion. And you also have to be able to put yourself in someone else's shoes. You have to be able to say, all right, my job here. People would always ask me like, oh, you were gay. And this was before politicians were in favor of gay marriage. That must have been hard. And the truth is 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 comparative advantage is, yeah, I had that ability, but I also, like, I can write a great joke. I can. And I'm a fast writer, too. And I felt like those two things together were part of my success as a speechwriter and then as a comedy writer.

[John Lovett]

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 9am to 3pm 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.

[Tommy Vietor]

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, let's say we have Tig Notaro and her wife on the show, Stephanie Allen. 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, then going over it again.

[John Lovett]

So once you sit down, you're a fast writer. 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.

[Tommy Vietor]

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. The When I talk about being a fast writer, though, I more mean like there were moments where you need a fast statement for the president to deliver about the Dow dropping or oh, I.

[John Lovett]

See what you're saying.

[Tommy Vietor]

Or the show is in an hour. We need three new punchlines for this. Or you're on set and you're trying to figure out how to make a Scene work. Those are the moments where I feel like, you know what? I can come up with something pretty quick that'll work.

[John Lovett]

But you thought that was gonna be your career then, right? Once you've gone into script writing, like, where are you? When do you solidify? No, I know what I'm gonna chase now.

[Tommy Vietor]

Never. I don't. I don't. I don't. I don't do that. I don't. 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 LA and be a TV writer. I took it. You just grab opportunities or.

[John Lovett]

But crooked media, that.

[Tommy Vietor]

So, you know, I was a speechwriter for Hillary, speechwriter for Obama, TV writer, did 1600 Penn, wrote some pilots, worked on the newsroom. But there was this pull to politics that I did feel throughout that time. The. And this is where I sort of would land on it, sort of 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.

[John Lovett]

A podcast that you didn't intend to continue, right?

[Tommy Vietor]

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 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, while 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.

[John Lovett]

What are 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 cn, 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.

[Tommy Vietor]

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 that. We didn't feel like what we were. We were certainly not inspired to go back to. 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 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 not, 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. 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.

[John Lovett]

So we have to do something. Isn't inspiration, it's anger.

[Tommy Vietor]

Anger is my motivation. I'm not a hope guy, I'm an anger guy. I'm motivated by anger, always have been. I find that it's when I'm at my bravest and most interesting. So there's been. 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, 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 not 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 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 why I think that's a bad look. Here's why I think that's bad politics. And so for me, I personally don't need inspiration from politicians. I need them to have it, to persuade others. But I am not in this to feel any kind of warm and fuzzy feelings.

[John Lovett]

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.

[Tommy Vietor]

I'm not sure. I don't think. I 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 as just a series of discrete decisions. And you make those decisions as best you can in the moment you see where you land. And then from there you'll have gained new experience, new wisdom, new insight, and more knowledge from which you can make the next decision. But I have never thought of it as a path more like you're kind of going from these islands, these little sort of staging grounds to take and to not look. And looking too far ahead, I think, is not particularly valuable for me. For me, maybe that's just A reflection of undiagnosed adhd that the idea of thinking three or four moves ahead seems impossible. So I'm just trying to get to the next stop.

[John Lovett]

Where is your mind a blessing and where is it a curse?

[Tommy Vietor]

What a funny. That's a very Barbara Walters in the 90s type question.

[John Lovett]

Is it? I wasn't trying to bring Barbara here with us, but I just. I know I can't. You sound like you obviously think a lot and that can. I know in my case if I'm thinking a lot, sometimes I get the comfort of the illusion of control. But it's like I really would like to it all to slow down in my head.

[Tommy Vietor]

Yeah, I have a noisy mind. I am lucky to be. I'm very curious. I don't find myself. I find myself interested in the ways in which we've done things for a long time a certain way without really much of a reason. And I find myself looking for those seams. Sometimes that's right, sometimes that's wrong. I think that my kind of floating around has been really good for me. I've gotten to have this incredibly varied career, right. Like, I ended up, you know, when I was a math student, I ended up publishing a math paper. I go into politics. I have this incredible speechwriting, short but incredible speechwriting career. I had success as a television writer, and now I've had success with Crooked and with Potsy of America and with Love it or Leave It. And I feel like that I was very fortunate that the fact that I'm able to kind of that, like, I get curious and interested and intense about a certain idea or certain project and I can really focus on that and then kind of can fully switch gears. I've been really rewarded for that. But I do think I've paid a price for not being able to quiet that noise. And there have been times in my life where I have not been able to really drill down and get something right. Like, I had this pilot for a drama. It was called Anthem. It was set up at Showtime. 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 struggle of that, I would just get pulled in a bunch of different directions and 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.

[John Lovett]

It doesn't seem like there's much serenity in it.

[Tommy Vietor]

No, I'm not a serene person. I'm not a serene person.

[John Lovett]

No, you don't aspire to it. Like, you don't crave it in any way. Because when I'm asking you these questions is because it's sort of. I recognize some of what you're talking about here, and I crave a different experience with it. Even though. Because when you said rewards, I was gonna ask you, is one of the rewards happy? 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.

[Tommy Vietor]

Yeah.

[John Lovett]

That it would be proprietary in a way that would be enriching.

[Tommy Vietor]

Look, I get to do the fact that I had this comedy experience, I had this writing experience, I had this political speechwriting 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. 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 are nightmare. But you are where you're supposed to be. You should feel very fortunate. You should feel very grateful. You shouldn't lose sight of that. Even in moments when life is tense or.

[John Lovett]

I could learn from that. I do not. I wish I could say all of those same things. And my daily steps don't have that kind of gratitude. And the way they should.

[Tommy Vietor]

Same. 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. There's this F. Scott Fitzgerald series of essays called the Crack Up. Have you ever heard of the Crack Up?

[John Lovett]

I have not.

[Tommy Vietor]

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 a. Just clinical depression, sleeping all day. And he's writing lists to occupy his mind. And one of the lists is times in which he was snubbed by those who are not his better in character or ability, which I always think about. But isn't that great line, right?

[John Lovett]

I mean, yeah, I mean it's just snuffed by people who aren't better than I am in any way. And this is not merit based making a list of it.

[Tommy Vietor]

I couldn't think of anything more Los Angeles than that. But he talks about feeling quite comfortable in that mode of living. And then he says, and then I got a little better and I cracked like a plate when I heard the news. And for me the pandemic brought me low enough 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 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 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 will look back on this and feel like I've still got plenty. I had plenty of place to grow.

[John Lovett]

Still not kind enough to yourself?

[Tommy Vietor]

I don't think so. Or to. 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, you know, that's it. And this is cooked. This part. This part's cooked all the way through. You put the fork in this part, it comes out clean.

[John Lovett]

If ingredients in love are acceptance and understanding and that, like, there's real wisdom in that.

[Tommy Vietor]

You have to do that.

[John Lovett]

I'm good with that about myself.

[Tommy Vietor]

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 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.

[John Lovett]

And also loving yourself in there. Like, I'm telling you something. I needed the help of a relationship to do that. 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. 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.

[Tommy Vietor]

Yes, yes. And I also, for me too, it's like a happy, really good relationship has been helpful, honestly. It's strange to say, but Manjaro going on. Manjaro has taken a big source of my self loathing.

[John Lovett]

Did you have body image issues?

[Tommy Vietor]

Tons. Still do. A huge problem for me. Huge, huge.

[John Lovett]

I've had them all my life.

[Tommy Vietor]

And I remember when I was talking to my therapist about it and she was really funny. She was like, you're gonna go on this thing and all the ways in which you kind of obsessively self criticize, they're just gonna find some new avenue, right? Let's say you go on this drug and it helps you lose a whole bunch of weight, you're not gonna stop finding ways to criticize yourself. And I was like, maybe not. Let's find out. And the truth is, like, the truth is it's somewhere in the middle, right? No, of course it's pessimistic. Well, but it is of your therapist, I'm saying no, it was her concern it was. She was not against my going on it. It was more, hey, go on it, don't go on it. But we still have to do the work. This isn't gonna address the work, which is correct. And I actually 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 gonna net out with less self criticism. Absolutely. There's all kinds of ways in which people. This is.

[John Lovett]

Math is useful.

[Tommy Vietor]

I'll give you. Here's one. I'll give you. This is one which is. Okay, I want you to imagine, okay, an X and a Y. On the Y we have gregariousness. I'm sorry. On the X we have gregariousness. On the Y we have charisma. Okay? Gregariousness. At the bottom, charisma going up and down, 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, 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 cool boar line. You want to be above that line. You want to be above.

[John Lovett]

That line gets distorted, though, by less fat, less funning.

[Tommy Vietor]

Well, there is that challenge. That is challenge. I remember when we were making 16:00, 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. Hilarious. It's all falling off of you.

[John Lovett]

It's not great for anybody involved.

[Tommy Vietor]

No, no.

[John Lovett]

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 truly 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.

[Tommy Vietor]

Yeah. 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. 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.

[John Lovett]

What a cool thing to chase though. We knew what it should feel like. That's a pretty good one to look, especially at the age you're in. Especially if you're doing some examination of. If you're doing the relationship and pandemic adjacent thinking. Even though it was earlier.

[Tommy Vietor]

Yeah, this was earlier. And we realized where we got luckiest is so the three of us started it. We hired three people right away. We hired someone to be our assistant to help us manage all this. We hired a COO and we hired a chief content officer. And those were incredible hires who really helped us build this. Without them it wouldn't have happened. That group of six really were able to figure out the next group of hires. Sarah, who was coo, was able to really build a business plan. And we launched the show in January and we gave ourselves a couple of months, then we said three months to get the audio. We were starting from scratch. We didn't have an RSS feed. We literally launched zero subscribers. We gave ourselves three months to get back to where we were in the ringer. Within an episode or two, the audience was back. Within three or four episodes, the audience had doubled. And then we were kind of off to the races and that, that gave us the space to launch other shows. Basically because we were so lean when we started. We never had to take investment, which meant we never had debt or shareholders who were breathing down our neck to grow, grow, grow, grow, grow. We were able to be deliberate and careful. That was a double edged sword because on the one hand we have been profitable. We have never not been profitable. That's strange for a media company, certainly media company, startup. But it also meant that we never had that like what had to drive our growth was the project itself, the belief in the company and wanting the company to be bigger, reach more people, fulfill its mission. We never had the kind of like we never had like a tech bro behind us breathing down our neck.

[John Lovett]

No, your way of doing it sounds better than my way of doing it because I went straight to 43 employees and invested. I like your way better. It seems like there's more control over that.

[Tommy Vietor]

Absolutely. There has been more control. But I sometimes think too, when you have what you have, there's a fire, there's an urgency. And so we had to generate our own urgency, which we did. Which we did. So look, we've grown a ton. I went from 5 to 10 to 15 to 20 to 40 to 80. I think we're at 100 right now, people. We've. And we've launched dozens of shows. We've built out YouTube, we're now, we've done touring, we've launched Vote Save America, which is our activism arm and seen great success there. So, like, we've grown a ton.

[John Lovett]

The most professionally fulfilling thing you've done. Yes.

[Tommy Vietor]

Yeah. Cricket. Yeah.

[John Lovett]

Like far and away nothing close.

[Tommy Vietor]

Yeah, that's right.

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[John Lovett]

What kind of challenges are there to the friendship?

[Tommy Vietor]

So there are absolutely challenges to it. I think what I've.

[John Lovett]

The reason I ask the question is because I work with a lot of my friends and I have a lot of friends that I'd like to work with that are like, hold on a second. I think this is gonna do this. We throw money in this. It's gonna mess a whole bunch of things up.

[Tommy Vietor]

So I think that you're combining two issues. One issue is, does working with your friends change your relationship? Of course it does. Of course it does. Then there's how do you work with your friends? I remember having this realization early on, which was, it's not much a realization, but wow, all bands really do break up. And. And we are not just we are a band, but we're also kind of a record label. You know, we're kind of doing both at the same time. We are the hosts of the show. We're also building this company and realizing that in that kind of environment in which there is stress, there's disagreement, there's a lot of incredibly rewarding moments that you share. Conflict that creates creativity, there's creative conflict. There's just different points of view. There's ego, right? You're hosting this thing together.

[John Lovett]

There's history, there's all of that.

[Tommy Vietor]

And realizing that really what you're doing is you're never gonna. It's not. Making sure you're working well together is not like a problem you solve. There's just a. It's a project, right? It's something you're gonna have to maintain. There's gonna be little moments that pop up and. And you have to talk about them and you have to be honest about them. And you can't let it build up. You can't think like, oh, things are good, or oh, we're having problems. It's that you are always going. There's always just a. You have to just kind of watch the pressure dials, right? There's just going to be some pressure dials and it's okay. There's going to be moments of tension between everybody. That's okay. But you're going to work 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. You know, we. We don't all see things the same way. We've had our conflicts over the years, but we ended up years later going through. We took on investors and we were working through the paperwork, a lot of paperwork. And there are always these questions about, like, well, what if you guys disagree or what? And we were always just like, look, we annoy each other sometimes, but, like, there was. We always would say, like, don't worry about what happens if the three of us disagree. Like, if you're our lawyers and you're trying to protect us 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, underneath all of it. Knowing 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 had to deal with.

[John Lovett]

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 gonna be challenges to it, but I would hope or I would aspire to have the friendship be something even better, deeper. After I've worked with my friends, it's.

[Tommy Vietor]

Just gonna be different.

[John Lovett]

But people will tell you, don't do that. Don't think like that.

[Tommy Vietor]

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've seen them all day, it's different. You're not going to. Like, 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 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 if you have a great friend in your life who you see each other after work a couple times a week or a couple times a month, and you catch up about life. And you spend Saturdays working out together and then going to a movie or something. If you work together, it's gonna be different. It's gonna be different. That's not a good thing or a bad thing, but just it is gonna be a change. And you have to just. We will it change. We never talked about that. It was just. This was what we have to do. This is what we're doing. It was absolutely the right thing.

[John Lovett]

What's been the hardest thing?

[Tommy Vietor]

What has been the hardest thing? So I don't know what the hardest thing is. The couple things. One is you go from hiring everybody to hiring the people, hiring everybody, to you come into the office and there's just somebody that's there and they don't know you. Well, sure, that's of course, I mean.

[John Lovett]

But that's the climb up the management ladder right there. That's how you end up being founders of a company. Aspirationally, you want to get to somebody else doing everything.

[Tommy Vietor]

But it's more that I think for me, it's like, I like the way it felt when it was 10 or 20. Just different when it's a hundred. And it's hard for. You realize, oh, you like, it's hard to convince somebody that they can talk shit to you. Right. If you feel like you're their boss's boss's boss. You know what I mean? It's just. It's different.

[John Lovett]

Yeah, well, yeah, because I work with so many of the same people for so long, I. I absolutely lose sight all the time of, oh, this person's receiving me this way now because I'm in charge or even more overtly in charge. And so I can't be exactly the same that I was before. But I haven't actually learned that lesson. I just keep making the same mistake.

[Tommy Vietor]

Yeah, there's that. I also think one challenge has been, as the company has grown, realizing that, making sure that you are maintaining the voice of the company in a way that is both narrow enough that you haven't lost what crooked media is, but expansive enough that as new and interesting and talented people come in, they lend their voice to the company as well and make it better. Right. So when are you demanding conformity versus demanding consistency, which are different things? That's been a challenge for me. Prioritizing has always been a problem for me. It is hard to be, you know, I'm a host on Mondays, I'm a host on Thursdays. I'm in a lot of other kinds of meetings. Wednesdays, Wednesdays, Tuesdays, Fridays, how do you.

[John Lovett]

Feel about all that? Right. Because I've gotten a lot of advice from people, don't do both things. You can't be both. You can't be an executive. And the microphone, both will be worse. And I felt it, like, I have absolutely felt that the shit I'm doing that I don't want to be doing that has to do with running a company is absolutely getting in the way of the other things that I do. And I can't get it out of the way. Like, there's no.

[Tommy Vietor]

That's a problem. It's a huge problem. Yeah, it's a huge problem. That's it.

[John Lovett]

That's it. You don't have any good advice for me on how to fix that, because what you're doing on Thursday, if that's your happy space and you're the founder of the company, like we. The thing that you just said that I thought was most interesting about just where the mirror is for me on. Did you just look at your watch?

[Tommy Vietor]

No.

[John Lovett]

You looked at your watch?

[Tommy Vietor]

No. Keep going, Keep going.

[John Lovett]

I didn't catch you looking at your watch. I caught it out of the corner of my eye.

[Tommy Vietor]

Looks very sweat.

[John Lovett]

It is going long.

[Tommy Vietor]

I'm happy to. I'm happy to.

[John Lovett]

The success. I'm just playing with you. The success of.

[Tommy Vietor]

Maybe I could have denied it. I should have denied it. I should have denied it. You caught me. But I could have gotten away with it. No, I didn't.

[John Lovett]

The way that the person outside looking at this, saying, what do you mean? It doesn't feel like success to have people hiring people before you see them. And one day you're the one paying a person who has come into your office, and you're like, who is that person? That is a sign of success that neither you nor I are absorbing as success. And furthermore, you're going. The next point of saying, and also, I can't commit it to a company that has the soul that I want it to have if I don't have more interest in that person. And one of the challenges I've faced in not having quite enough management for the number of employees that I have is in the absence of, like, real care and communication, what falls into those cracks can be, like, trust and. And things that. Things that you just don't want to have with your employees.

[Tommy Vietor]

I think it's you. I think, like, fundamentally, I think all of these things tie back to what happens when you're moving too fast. Right. And when you're moving too fast, sometimes the shows you're Hosting may suffer a little bit because you haven't paid enough attention to them. Sometimes you're kind of in, like, you're kind of. I sometimes joke that, like, I'm sorry to pop in, like, the Babadook. Right. Because 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 I think sometimes when you're moving fast, you realize, oh, I wasn't in a. I could have approached that in a more sensitive way. Right. Or I was brusque.

[John Lovett]

In that moment, I punch myself in the face, though I'm not gentle with myself there. Once I've realized, oh, I could have done this, I. Yeah, of course.

[Tommy Vietor]

Of course. And I do the same. 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.

[John Lovett]

That one's tough for me.

[Tommy Vietor]

Yeah, it's tough. And it's also part of it, too. I've noticed, too. It's. You have really good people. They're 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 being busy, you know, to go back to where we started. Like, I have a very good relationship. I like being pulled in a million different directions. I like a busy day. Like, I'm gonna go from here. I was looking at my lunch. Cause I'm gonna go back from here, run back. We're gonna meet to talk about a design thing with this incredible designer who runs in our design team. Then I'm gonna meet with the Love it or Leave it team to plan a bunch of stuff. Then I'm gonna meet with the politics team to talk about what we're doing with Boat Save America. And I love getting to do all those different things. And as long as I feel there's a meeting we do called Comedy Corner, and it's a meeting that started five or six years ago. Comedy Corner was the name of a few funny people at the company, different jobs who just get together and brainstorm funny things we could do. And then it's now, as we're 100 people, it's now grown into a weekly meeting run by Hallie Kieffer, who's the head writer of Love it to Leave it where people come to pitch and also to get ideas for their project. So we need a merch idea. We're naming the this website or whatever it is. And I don't go. It used to be my meeting. Now I kind of go once in a while, and I'll be in the meeting and we'll be pitching, and I'll throw a couple ideas. And a lot of times, if the meeting is pitching something for my show, I actually don't go because then it becomes pitching me, which is not the purpose. But I like to try to go and just be a person pitching. It's not my meeting. I'm just here to throw out ideas and we'll joke, like, especially with the people that have been there a long time. Like, did I add anything to this meeting? Should I have come to this? Right. Cause sometimes if I go and then all of a sudden, everyone's pitching at me, that ruins the meeting. But then sometimes I'll come and I'll be like, oh, you know what? I have an idea. And then it's like, all right, I still got it. I can still do it.

[John Lovett]

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. Look at this. I'm presiding over a writer's room that I have the ability to.

[Tommy Vietor]

Harm or.

[John Lovett]

Help by my present, but it's mine.

[Tommy Vietor]

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?

[John Lovett]

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?

[Tommy Vietor]

I think that's the wrong thing to care about. 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 I think kind of 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. Oh, I don't want to let this group of people down. And if I'm here, I want to make sure that I'm doing what I'm supposed to do to validate everyone who's decided to be here. I think for me, I really take a lot of joy in routine and kind of hitting my marks in each of these places. And I feel most proud when I am able to bounce from all of these and play these different parts and do it well and do it with kind of joy in the moment. That's when I'll be like, you know what? It's not like, oh, look what I've assembled. But more like, love it or leave it. Somebody said this. Like, people always say, like, oh, wow, you guys have a lot of fun in those meetings. And we do. And that's, to me, when I feel the most joy. It's not like, oh, wow. It's more like. Like we're putting 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.

[John Lovett]

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.

[Tommy Vietor]

Didn't say that, actually. I said that it's a thought process that could encourage arrogance, which I feel, which is why I fight it.

[John Lovett]

And you said it was unhealthy.

[Tommy Vietor]

And I think it could be unhealthy.

[John Lovett]

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.

[Tommy Vietor]

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.

[John Lovett]

If you're that aware of it, though, if you're that aware that this is unhealthy, this is a poison to me.

[Tommy Vietor]

I think it's a little kind of like, you know, Simba, everything the light touches, I think that's all unhealthy.

[John Lovett]

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.

[Tommy Vietor]

I think if there's value to you saying, you know, this is hard, this can be frustrating, but, like, look how far we've come. Look what we've made already. I don't think there's anything. I don't think there's 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 worse fighting, because it's also. I have trouble with the word yours. You oversee this thing that you've helped build. It is a result of a lot of people's work. It's a result of a lot of luck. It's a result of a lot of talent. You reap a lot of the benefits from it. But it's a collective work as well.

[John Lovett]

That'S healthier for your company, maybe for you and your company. Like, if they're feeling that off of you.

[Tommy Vietor]

I hope so. I hope so. I hope so.

[John Lovett]

I will let you go on this note. A complicated question, because I don't know how this felt to you, negotiating for one year over unionization at your company, a progressive company that prides itself, I'm sure, on being good to people, absolutely cares about. And then all of a sudden, you've got a company so big that I imagine that when all of this path was in the making, you did not imagine negotiations with a union over lawyer language stuff.

[Tommy Vietor]

I think what we took from that experience is, you know, we went from. I'm going to get these numbers a little bit wrong, but say roughly from. We, like, more than doubled in size during the pandemic. And that's a lot of time and a lot of culture to develop when people are sitting in their homes and not together.

[John Lovett]

And you are being fundamentally altered during this period because of the changes you're deciding to make.

[Tommy Vietor]

Everybody's going through it. Everybody went through it. Everybody went through it during the pandemic. Now. Everybody, Everybody, Everybody, everybody. And we grew a lot, and we changed a lot. And we also were kind of. Our business was growing and changing. We were working with Sirius. We were taking on investors. And I think we had a lot of work to do to build better communication across the company, not only to convey both, also, first of all, we had to figure out what direction we're going in. Then we had to convey that, and then we had to kind of work with everybody to kind of build a kind of collaborative, trusting, positive culture for the company. And I think that is something that came. The realization of how important that was, I think became clear through the collective bargaining process. But I will say now that we're on the other side of it, I feel like there was a lot of kind of growth we did together to get to that agreement. And now we have that agreement, and I do feel like we're in a really good place.

[John Lovett]

Congratulations on all your success. I will let you go to all of your many things. It sounds like a frantic life. No, it's not. It sounds. Yes.

[Tommy Vietor]

It looks like when I walked in, you were like, are you stressed? It's like, no. This is baseline. This is base ride.

[John Lovett]

This is who I am. I just. Well, you swept into the room and I'm going to say it was a bit of a tornado of it. I couldn't place it. Is that anxiety? What is it? Is it frenzy? It's energy. It's a lot. But you could love it or leave it. You could also pod save America with him. It's all things crooked media. I appreciate the time and the honesty. Thank you.

[Tommy Vietor]

Thank you.

[John Lovett]

And for being so contemplative in the questions and the answers.

[Tommy Vietor]

Nice to have a chance to slow down.

[John Lovett]

Yes.

[Tommy Vietor]

How about that?

[John Lovett]

I forced it upon you. Nice. Nice to have a chance to be arrogant.

[Tommy Vietor]

I never said. For the record, if you go back and listen when we have this recorded arrogant. I said it could lead to it. I said it could be reported.

[John Lovett]

Is that you go back and look. I saw you look at your watch. I was talking and you looked at your fucking watch.

[Tommy Vietor]

I, I subtly, subtly. There's no clock in it. Oh, there is a clock right there. I could have just looked to my right. I fucked this whole thing up. Yeah.

[Jon Favreau]

I want to give the Miami Marlins a shout out for a second here on the show, folks. They've had a strong start to the season, playing about.500 ball, one of the leading teams in terms of batting average. Been incredibly entertaining. There's lots to celebrate, including a really cool performance from Max Meyer that made him a pitcher that stood only with Randy Johnson. But that's a celebration for another time. If you're celebrating now, whether it's a game night, a party with your friends, a special anniversary. Celebrating important occasions means more moments with the coolest people in your life. Cheers to 50 years of Miller Lite, the great tasting light beer. For people who Love beer since 1975, now's a perfect time to celebrate legendary stories with friends, family, and a great tasting light beer. It's Miller Time. My personal favorite part about Miller Lite is that it's brewed for taste. Simply put, it just hit hits different because it has simple ingredients like malted barley for rich, balanced toffee note flavors and iconic golden color. Miller Lite Great Taste 96 calories Go to millerlight.com beach to find delivery options near you. Or you could pick up some Miller Lite pretty much anywhere they sell beer. It's Miller Time. Celebrate responsibly. Miller Brewing Co. Milwaukee, Wisconsin 96 calories and 3.2 carbs per 12 ounces.