The Dan Le Batard Show with Stugotz - South Beach Sessions - Tommy Vietor

Episode Date: June 23, 2023

Tommy Vietor may have left the White House, but imposter syndrome followed him to Hollywood... Dan welcomes the co-founder of Crooked Media for a conversation more powerful than politics. Tommy shares his realization that leaving politics was the best decision for his personal growth; how opening up about tragedy can bring strength and solace to others. Dan and Tommy also compare what they've learned from starting media companies with their friends... and everything they still haven't figured out. Listen and subscribe to POD SAVE THE WORLD, new episodes every Wednesday, and POD SAVE AMERICA, with new episodes Tuesdays and Thursdays, wherever you get your podcasts. Learn more about your ad choices. Visit megaphone.fm/adchoices

In the recent versions of South Beach sessions we've been talking to my friends about really vulnerable things and I cannot say that Tommy Vittor is my friend. I can say that I have admired his story from afar because it seems crazy to me. Some of the stuff that he's done and the business venture that he is now embarked on, which is wildly successful, but probably comes with some trapdoors that he never expected and the audience has no idea about. So just a brief synopsis in his past life, he worked for President Obama for nine years, including his White House National Security spokesman. He is now the co-host of PodSafe America and the host of PodSafe the World, the weekly no bullshit conversation that breaks down international news and foreign policy developments and it's not boring. It doesn't, this is hard subject matter and they make it fun to learn with them and he makes it fun to learn. He also has, you know, basically started the crooked media empire that he co-founded with his friends.

And so Tommy, thank you. You can listen and subscribe to PodSave the World, new episodes every Wednesday and PodSave America with new episodes Tuesday and Thursday, wherever you get your podcasts. Thank you for joining us. We've never spoken, but your story seems crazy. So let's just start with what do you think is the craziest part of your story? Dan, thank you so much for that very nice intro. And for having me on the show, I've been in kind of a defensive crouch all morning as Boston sports fan. I thought this was just gonna be a Celtics roast, a Bruins roast, whatever you wanted it to be.

But if you would wanna skip over that part, just beating me down. We can make fun of Bill Simmons later if you want to. We can do that together. We can just use him as the symbol in Avatar for making fun of all things Boston sports. Okay. But pain, because you come from that tree,

I'm super curious as to how all of that happened, but just before we get to that, what do you view as the craziest parts of your story, your journey? The White House, the White House. I mean, I think so much of life in my career has been luck in timing. And basically, I graduated from college in 2002.

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

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

to me so that I could explain them to journalists and help people understand, you know, what Obama was doing when he went to Turkey or something like that. So yeah, it was a hell of a job. But were you being aspirational or ambitious here with career goals in mind or were you just, no, I want to learn. This is going to be fun to learn. I think, you know, I was thinking about this today because I, you know, think about some of the questions for the show. Thank God we were so young and stupid

and almost didn't realize how much we didn't know by, and when I say we, I mean, the people I worked with on that campaign, because when you go from a political campaign, see what an administration, in a sense, you're prepared for it because you've been working 100-hour weeks and you know, you know, Barack Obama's record inside it out and you have dealt with the press, but you're never actually prepared for the problems that you're going to face once you get into an administration. You know, thinking about things like the Fukushima nuclear meltdown

that happened in 2011. I mean, there's no preparing yourself or preparing a government to go into a meeting where someone says, hey, this nuclear reactor in Japan is melting down and we might have a Chernobyl-like event if the following things don't happen. So it wasn't ambition, it wasn't anything about my personal career track.

It was sort of something that felt fun and exciting and there was a team of people doing it together and a shared mission and a shared goal and a really inspiring leader and that just made it fun and rewarding. But how far are you now from whatever it is you were dreaming you were gonna be? I mean, in a sense, it's just a completely different place.

You know, I mean, when I left the White House in 2013, I thought to myself, I've been on this, you know, Ferris Wheel, this merry go round for about nine years working for Obama. I've been in politics for a little bit longer. It's time to step off. It's time to do something else with my life. Get away from politics. Move on from that. Get out of DC. I did it for a couple of years, but it didn't stick because here I am 2023. Still talking about Joe Biden's record, still talking about Donald Trump, still for a focus in obsessing about politics every day. Yeah, but, but, and also running a media empire with your friends, which is a totally different,

it's a totally different thing than, I mean, I don't even know where your primary concerns are, but yes, I've focused on the things in sports that I focus on, and then I look up one day, and I'm managing 50 people, or I've got 50 employees, or whatever it is, you have a, your story is parallel here, where I don't think that you ever imagined that, did you?

No, not at all. And I'd love to know what the experience has been like for you, but it started with three of us, then there were six, and then there were 20, and then there were 50, and then all of a sudden we realized, management's a full-time job. And there are people that are really, really good at it.

And there's people who are less good at it. And I think I don't know if three of us would have been really, really good at it. If it's been in the entire focus or not, probably not. But when you're recording a couple shows a week and you're touring and you're focused on all the political things we want to focus on. We realized we needed to bring in some folks who could manage the place full time.

So we had a CEO who really focused on the operations, the nuts and bolts of the place. And then recently we hired a CEO that's fully running the place and letting us, John, John and I, be more focused on recording shows. But I'm not sure how, how did you guys manage things from sort of no employees to to many? With me after shows very often walking into rooms, sitting in a chair, being close to sobbing and saying, I don't know how to lead. I know that feeling.

I know that feeling too. I mean, or someone I was talking to a friend, this guy Ben Smith, who ran Buzzfeed News for a while, and then started a company called Semaphora, which is another media company now. And he said, the thing about having more than 50 people on staff is every week somebody is having the worst week of their year. And that sort of bleeds through into everything in your life, whether it's you or somebody on your team and you have to figure out how to help them

or account for that or make things work despite what everyone's going through. So yeah, it's been an enormous challenge. It's a full-time job. Our CEO, John Skipper, who used to be the most powerful man in sports says it's a hell of a lot easier managing 10,000 people than it is managing 40 people because of what you just said. Because if you're going to build a company that actually cares, that has a soul and I want

to talk to you about this because you found a unique space in the media landscape, really unusual place where you can be vulnerable and you can be the other side to what seems to be having more success, which is right-wing stuff that's getting traction and you're out here fighting a different kind of fight on the other side with facts and nuance and real expertise, but I along the path have felt really lost and I don't know if you'd never considered the idea of running really lost and I don't know if you'd never considered the idea of running. Like when you're working for Bill Simmons, it just seems like a magical job, right? You're just allowed to talk into a microphone and just show off your expertise, you go home and you're done with your work day.

It's much easier than anything you've been doing before and probably more funds than you're doing it with your friends. Yeah, I mean, what happened with Bill was John Favreau, who is one of my co-founders here, went to Holy Cross, where Bill Simmons went to college as well. So they like, I linked up many years ago, became friends, being friendly. John moved at the LA, and Bill said, you know, what if you and one of your buddies came in and did a podcast about politics running up to the 2016 election? So John and Dan Fyfer, and then John Love and I started doing a show called

Keepin' in 1600 a couple days a week. And it was a really fun hobby, but it was part time. I was still living in San Francisco at the time. I would just sort of Skype into these calls. But slowly the show's audience really began to grow and grow and grow. And then when the election happened and everything we thought but slowly the show's audience really began to grow and grow and grow. Then, when the election happened, and everything we thought was going to transpire,

Hillary Clinton didn't win Donald Trump on states like Pennsylvania that Democrats thought were impossible to lose, we all felt this enormous sense of guilt and feeling like, the things we cared about were too important to let them be a hobby and that we needed to go all in and do this full time. And that's where a crooked media was sort of born. If Hillary Clinton wins none of this exists, probably not. I mean, it's a great question. I think about it all the time.

Maybe we would have decided that there was still a place for a different kind of conversation about politics we might have, but I don't know that we would have done it with the same urgency that led us to start crooked media right away to launch the shows in early 2017 for me to convince my now wife to pick up and move from San Francisco to Los Angeles. I think that would have been a little bit tougher. Well, tell me some of this, right?

Tell me about the sacrifices that people don't see when you're taking over a hobby, making it a job with your friends, but now comes also the pressure of, we're gonna be activists here with facts that inform people and we're going to believe that there will be nutrients that people will buy and we will be able to create an economy that actually is a fighting machine and it's gonna try and fight with facts. Yeah, I mean, so there's definitely a recipe in the right wing talk radio that you guys have watched forever from Rush Limbaugh to some of the, you know, crowd or folks who are on now.

That's very angry and divisive and, you know, you, you, lots of demagoguing groups, especially LGBT people, people of color, right? I mean, you see this all the time. That recipe does not work on the left. I'm glad it doesn't. I think the more progressive side is motivated by things being funny, inspiration, more fact-based conversations. So that's what we wanted to cook immediately to be. We wanted to be a place where you could talk about politics that didn't feel like cable news, where it was like these stilted debates

in the same talking points and the same people in these green rooms over and over again. There was a little more entertaining, there was a little deeper dives on the issues people cared about. But then if we were talking about something you really cared about and you wanted to do something about it, we wanted to be the place that could help you figure out how. And there's no magic bullet, you know, there's no easy answer when it comes to solving some problem or making sure that our democracy is protected. It's a day-by-day process of citizenship and voting and volunteering and donating. But we want to create that infrastructure to make it easy for people and also to make them not feel hopeless because I think the kind of demagogues win when people feel like politics is a waste of time.

All these politicians are the same. What's the point you've even tried? That I think is the worst thing that can happen to people like me who think the government can be good and help people when done right. But if you're in a dirty fight and a corrupt fight, if you're in an ugly fight where the other side isn't fighting fair and you come to the fight with funny and inspiration. You lose those fights. That's why what you're doing is tricky.

It's why I admire that you, I mean, the downloads that you have are crazy. You have found an audience that not unlike you who chose the White House because you wanted to learn because I don't want to skip past this part. I think it's important. If you don't have political ambition and climbing that is now corrupting and contaminating all of government and you were just in government, more, I shouldn't say just, but to learn, you take your ego and the ambition out of it, you got out of government what you needed, which is an expertise, and you listened. You weren't so interested in climbing or showing others what you knew, that you had the

foremost experts in the world, giving you free information all the time that you now use to have a thoroughly expert podcast. Thank you. I mean, that, one of the coolest things about getting to work on the national security side of the White House is there is this little team of people called the National Security Council. And for under us, I think it was up to like 500 people who were on that staff. Almost all of them, very few of them were direct hires.

A lot of them were detailed over from agencies. So the CIA would send somebody over, it's Penn's Department, the State Department. A lot of those people were career- born service officers, career intelligence officers, you know, people who are in the side of politics or in the part of government that is not political. And so I never knew their partisan leanings. You know what I mean? I just knew that there was this really funny guy

from the CIA who was in meetings with me a lot and would help me out when I needed answers about what was going on in Syria, for example. So it's just a really amazing window into government and sort of like the selflessness of the people that serve in it and aren't known, you know, don't make a lot of money, a lot of not to deploy overseas to scary places sometimes. And don't take the seat of their families, but are really, you know, they're in it for the right reason.

So I saw like a much better side of government than you see on, you know, Fox News or a cable TV show or what have you. How much corruption did you see? How much overt hopelessness did you see at being able to do activism in government that wouldn't be contaminated by the self-interest. I think the corruption you see is not necessarily stuff that's illegal. It is the unbelievably broken campaign finance system. Like you guys in Florida, right?

You have Ron DeSantis, who just recently changed a rule, a state rule, about how political action committees are governed or what their rules are, that will allow him to transfer $80 million to his presidential campaign. He just gets a tweak of rule to change that. I mean, that makes no sense. The amount of money that you can raise from PACs and from lobbyists, the impact that has on our politics and that was the stuff you see day-to-day

that can be pretty pretty demoralizing are you frightened by how heartless how solace so many of the people around you in politics were or are i don't think i was frightened i mean i think you see the system is sort of set up for really ambitious people to fight each other all the time and to provide checks and balances. I mean, that's sort of like the brilliance of the of the founding structure of the government and the

documents. So that part, I don't know that that should make anyone feel better, but that is sort of the system we inherited. I think what is gross is some of the individuals you come across, like, you know, again, I don't mean to pick on Florida, but you know, talking to you. But like, Matt Gaetz, people like that who seem to have absolutely no kind of anchor when it comes to what he believes in, it's just sort of constant drifting in the wind. I mean, that was the stuff that that bothered me stuff that bothered me and that shocked me and that, you know, can make you feel like, I don't know why people are doing this.

For the uninitiated, can you tell me how the origins of the name Crooked Media? You know, Trump said it. He would always complain about the Crooked Media. And we thought it was funny if we took it back and just owned it and made it our name. Because I think the frustration people have with media is there's sort of your conservative outlets,

your more progressive ones, and then the ones that are supposed to shoot straight and just be just the facts like a CNN. And there are, it's sort of a broken concept of media, in my opinion, like the idea that reporters don't have biases. I think we all bring experiences, our identities, biases to the table. And we want it just to be overt about them.

You know, I mean, we are liberal people that worked in the Obama administration trying to talk about politics in the most honest way we can. That comes from a perspective. You can call it crooked if you want. We think that's kind of funny and that's okay. You mentioned your wife and asking her about a pretty substantive life decision. I know I just know I wouldn't have done any of this.

I wouldn't have left ESPN, I wouldn't have left comfort, I certainly wouldn't have started a business if I did not have this undying ride or die support at home for the days when I come home on my hands and knees. So explain to me what your wife who loves you, warned you about working with your friends and taking on a venture that now has an enormous amount of responsibility

on top of it. Yeah, I mean, I guess what you're, you know, when I told my wife, you know, so I left the White House, my friend John Fabro and I, we started a company that did a lot of speech writing and kind of like communications consulting work. It was a good job, we did pretty well. I liked a lot of people I met,

but I wasn't totally fulfilled. Then we started doing the Keepin' A 1600 podcast on the side. We did pretty well. I liked a lot of people I met, but I wasn't totally fulfilled. Then we started doing the Keeping a 1600 podcast on the side. That was fun. It made me realize that I wasn't escaping politics, that I was so obsessed with it. Then when the election happened, I went to her and I said, Hannah, we want to start a company, make this a full-time job and give it a go. I think, understandably,

she was sort of like, do you really think podcasting as a full-time job? Which, you know, in 2017, I think most people probably had that reaction, might in-laws, my parents, a lot of my friends. I mean, I don't know if you encountered sort of the same response to people. I mean, I did with my family, it wasn't podcasting,

it was a million years ago, but the idea of writing sports and making any money for a living when your parents are exiles who fled, defined freedom and my father wanted me to be an engineer. Yeah, he didn't talk to me for a long time because he, I mean, I might as well have said, you know what I want to do? I want to be the lead singer of a rock band

and do just a bunch of heroin. And also they're not gonna pay me anything for it. That cool with you, Dad? Yeah, like, but it's not as ridiculous, your wife knows you. And this is why I said, couldn't have done this without my wife, just couldn't have done it. She saw the ways that I was not fulfilled and she wanted to push me toward happy,

to challenging myself, but something that was more rewarding, more fulfilling while a lot of people also warn you by the way. And I'm sure you got this. Be careful about working with your family and friends because it might cost you your family and friends. I have a friend who did that and it caught. He made a lot of money, made a ton of money and it cost him all the friendships before

he was 30 years old because that navigation can be very hard. I don't know how you've navigated it. I don't know how we navigated either because we're not just business partners but we also share the microphone a couple days a week on shows. I think maybe the answer is you know every once in a while you just have to scream at each other and fight it out and then then move on and get over it like a sibling. I do think it's more like brothers than friends or business partners at this point. What are the challenges you weren't expecting? Honestly, I think the challenges you weren't expecting were how hard management is, how

much focus it takes, how much time, how much focus it takes, how much time, how much empathy and understanding, and how it'll prepared, I think I was coming out of politics to do a lot of those things, because my job was usually as a spokesperson. You know, I went out to Iowa, I lived there for a year and ran the Iowa press operation for Barack Obama. I was the press secretary, another friend of my Josh Ernest who was later the White

House press secretary, was a communications instructor. After that, they were like, you're doing rapid response in the White House. I handled a bucket of issues, which is a long-winded way of saying, my job was like, here's a task. Go sit at your desk for 12 hours and do it. You know? And I didn't rely on managing a lot of people who are working with folks.

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

Well, so I met Hannah in 2012. So we were together for about a year and a half while I was at the White House. Her, she was definitely one of the reasons I wanted to leave when I did, which is in March of 2013, because I knew that I couldn't focus on her and our relationship as much as I wanted to if I was in this full-time job.

It wasn't lonely in that we had a team of people and it was kind of ragged ag that I'll do the campaign together and then went into the administration. We really did have that kind of like band of brothers like group of friends sort of shared misery, shared triumphs together that kept you sane. But there were definitely days where you're, you know, you're there after a really long day or you know, to late Friday night or Saturday morning or something like that and you're still at the office and you're just like this sucks. Yeah, but what you're talking about there though, the emotional bandwidth that you're giving, you're saying, yeah, try and you, you,

and the feed of the job and hooray, and there's this so invigorating, but what do you got when you get home because you're not gonna have a whole lot left in the tank if that's what you're giving your job? Like it's hard to, I mean, I don't, I have spent two years telling our employees, give me home to my wife, please get me home to my wife.

I want to be there because it's so hard to do both. Yeah, and listen, it recently I realized how hard it was because we just had a baby, she's almost six months old. And if I don't get home before six, I don't see her that night, you know, because she goes to bed at like six, 15 or 6.30. So that's become a real pull that gets me the hell out of here.

And makes me think back to all the people I worked with at the White House who had kids at home at the time and we're stuck late day after day after day and just never saw them. I just can't imagine doing that job now. How did Hannah know that you were not fulfilled and what are the differences in you now because it sounds like you've got like it sounds like this is the happy lane. Yeah, this is definitely the happy lane. I mean, I think Hannah knew, so we're living, we moved from DC to San Francisco. I was doing this consulting job with John Favreau

and a couple other folks, but I was doing a remote leave from San Francisco so I was just working from my house. And she would leave and go to work and come back and I would just sort of still be there. And I hadn't really had any human contact all day and that just did not work for me. I am a person, I'm a social animal, I need to see people,

I need like water cooler talk, just something, some sort of distraction and being home alone all by myself in our apartment for a couple years broke my brain. And so I think she knew that yes, I desperately wanted to try to create this media company to fix the way politics is talked about in the country, but also I needed to get the hell out of the house to be around people again and do something like that had a team element because I just missed that so much. Hannah did not marry a puppy. That is not something that she married. She married somebody who has a puppy who has to interact with other puppies. It's so much you say that because she would literally, she would come to the

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

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

when there's a million other options out there? You know, that's a day to day thing. So why make the bet? Make the bet because deeply felt guilt about having been so dedicated to politics and then pulling myself out at a moment when it felt like I should have stayed in. And feeling like the conversation about politics in the 2016 election was as bad as it had ever been, because all people cared about was the horse race and the games, and they didn't talk about the stakes and the impact on people's lives and why it mattered and how we all need to get involved.

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

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

There's upstarts, there's bar stool, there's ESPN, I mean, there's just like competition everywhere. Yeah, I'm not competitive that way. So that's not where regret or doubt would see been. It's on the hardest days when I feel like managing of people is hard and I never, never envision myself as any kind of manager of people. I've always been responsible. It's just self-sufficiency. Me, the microphone, do what it is that you do. You don't have to, like, it'll take care of itself. You're worry of others.

The economy around this fun thing will take care of itself, but I had reached a point at ESPN where I couldn't keep eating silence when I'm freedom first, voice first, and I'm too much about I've got to be able to speak freely. And so the muscling was a different kind of unfulfilling. It was too much of a sacrifice of, of principle, principles that I couldn't abide. I couldn't, I couldn't look myself in the mirror if I was living in a space where

I had to Sell out that Obviously like sell out in a way that I couldn't come up with a rationalization when I was looking in the mirror for what my Families about and and so I just I had to do it and then it came with when the discomfort arrived What it felt like was just unsafe, because it's not regret, but it's just like, oh my God, I could have been caching checks, talking to a microphone for millions of dollars if I had just kept my head down, but not been able to live with myself.

Yeah. Do you think that Yisby and Brass regrets trying to muzzle people? It's so much more interesting when you don't muzzle people, no? At Disney. That was a question. I just don't think that they want the headline. Why would they want the headlines around a sports program of sports host goes after Trump. Like what do they need that for? It's a little bit easier to just hire Pat McAfee, give him $17 million a year,

and he's probably not gonna do that. Yeah, all right, that's fair. But I mean, I don't know. It seems like there's some really interesting people like saying their thing, you know, like the whole stick to sports shut up in dribble, LeBron get out of politics, like I don't know that that worked too well for his critics.

You tell me what value people in sports have for all of this stuff, because I've found that it's safer and more rewarding, generally, to just stick to sports. You won't lose sponsors. Like I'm not saying that that's what anybody should do, but if you just stick to sports, you're not gonna, man, I don't wanna be trusting Bud Light from my moral compass.

I don't want to have to worry about what they're dealing with in their meetings so that I can say this or not say that. How much politics do you see with your sports? You know, I titter-miss. You're right. Listen, obviously, just from a purely financial standpoint, you can probably identify a few topics that if you never touch, no one will criticize you. I do think there are people that get involved in politics and sports,

like the Rooney family, that I think have done really well by themselves by seeing as sort of like principled leaders in a couple of different areas. But, you know, I hear what you're saying. I mean, it's certainly more complicated. And the runies are foremost leaders on racial matters. This is the funny part about what it is that you're saying. I don't even think that I talk politics. What I've been talking about for many, many years has been race. And it gets hijacked.

It gets turned into politics. When all I feel like I'm doing. And I'm now viewed, I'm called libdard and woke. The Cuban community will call me Guzano Worm for being a traitor against the politics of my region here in South Florida. But all I think I've ever advocated for, which is now, somehow a controversial position is how about equality and decency for all? Like that's that's why I'm politically I mean I'm guessing many people who are on the other side of this are saying no

You're an asshole you're obnoxious you're strident and you're you're way way left-wing but I believe I'm only somebody who says can we be decent to everybody I don't even care about politics Yeah, well, and what you're saying is essentially what a lot of athletes were saying, who are silenced or shut down or told to stop kneeling, which is they were more specifically saying, hey, we want to prevent police brutality against black people. And that was twisted as sort of a political statement.

And people were told they were being woke or sick to sports or whatever it might be. When really it was just about equal treatment of everybody. I'm so disappointed though, Tommy, that that works somehow. I know. Like, one of the things I was always saying to myself, I think I said it publicly, I know I was saying to myself privately, if you're a corporation that has as much money as X, whomever it is, if you have FU money, why would you never say F you? Why would you never choose a side and say F you?

Because you got to make more F you money to never say F you? Yeah, no, I mean, I think Bud Light, you mentioned Bud Light earlier. I mean, they basically sent one specialized beer can to an influencer who is transgender, They basically sent one specialized beer can to an influencer who is transgender, a person who just lives her life on her social media and it was just a nice little thing. And all of a sudden you have Chris Rock,

I'm sorry, I'm not Chris, you have Kid Rock shooting a machine gun at a bunch of beer cans. When this same sort of group of people two years ago were complaining about cancel culture and freedom of speech and silencing people. It's like, I do think like to your point, it's important when corporations cave like that, and when they are getting attacked in these cynical ways to sort of call out what's happening here, and I don't know, and just stand for your principles.

It's not that hard. Where have you been tested since going closer to the fear and fulfillment? Where have you been most tested? I mean, I think what was challenging was, you know, when you worked, I worked for Obama for nine years and over time, like his opinions became my opinions, you know, for not consciously, but you know, you become kind of like oven administration, you feel like you own part of it, the collective

group of people doing these things. And then you leave government, and for a while it took me, it took me a little while to like kind of deep program myself and get out of talking points mode and getting out of being defensive of everything he did and to think for myself and to speak for myself. That's scary. It's a lot less scary when you have some air cover from the President of the United States to help you defend your thinking. It's a lot harder when you're just kind of siding on your own. It's scary, but it's also growth, right? Yeah, absolutely. And it's ultimately a lot more rewarding and freeing

to feel like you can just kind of weigh in on whatever you want, including talking about things where we screwed up and ate mistakes. I'm fascinated by where growth can be found for a whole lot of people that I've seen have success when they go toward the scary, when the deep programming of that, things I've always believed, things that are my identity politics, things that are my ego, I'm going

to go ahead and walk toward the fear. Man, there has been real learning in that for me, but it's so easy to say. And I don't people who, I don't think it's normal to seek necessarily change that requires you to reprogram your whole system. 10 years you dedicated, I'm assuming if it's 100 hours a week that you basically were getting all of your ego and identity at work. Absolutely, 100%. All of it.

And it becomes who you are, it becomes your identity in a lot of ways. You're, you know, a bomb a guy, you work for him, you're part of this administration. But can I ask you something you said a minute ago, which was you said you've been taking a lot of flack from the Cuban community in Florida. Is that over like specific, Cuba specific US policy stuff? Or is that that more generally which is the history? I mean Cubans are Republican and so they somehow look at Trump and DeSantis and see the opposite of what I'm looking at as someone who is broken free from all that programming you're talking about.

I think I'm a bad Cuban voice because you know what the politics of Miami are, right? You know what the politics of Florida are,? You know what the politics of Florida are where DeSantis is someone who's supported. I'm surrounded by people who think I am not only wrong But Guzano is a specific term. It's a term going back to the revolution in Cuba Warm is the worst thing you can be if you're someone on the other side of this Somehow and I don't get this from my people. I don't understand it I've had I've lost friends. It's been heartbreaking. The last few years of what this has been just not understanding how people look at Trump and DeSantis and see decency there. Like just decency. I'm not even talking about anything else. Just

decency. Yeah. Yeah. I mean, that's, you know, it's funny. One of the biggest, one of the things I was proudest of with Obama was his ability to kind of break with orthodoxy and specifically on Cuba when they tried to restore relations, get the embassies back up and going, like sort of begin to chip away at the embargo. But then I noticed that some of those policy moves were just wildly unpopular. They never grew in popularity over time. They only got worse. And I always wondered why that was. And if that was about what Obama did specifically,

or if that was more about his identity and just sort of a fundamental rejection of the Democratic Party versus like the things he tried to do. No, it was both though. It was a lack of understanding of how hostily offensive it would be to normalize relations with a country that was still being run by the version of our Hitler. I always get in trouble when I say that, but Cuban people in Miami think of the Castro regime and Cuba as a relationship that cannot be normalized,

should not be normalized, even if it punishes the people of Cuba, which is not something that I would agree with, but I understand how they arrive historically passed down through generations at that opinion. I remember my mother, she asked me, she was trying to express her feelings on Facebook, and she asked me to help her with the writing of it. And I remember that that information somehow, however I wrote that through Tony Cornheiser or I guess golf with Obama ended up being a part of however he tried to cross that bridge. But you still don't understand in retrospect how it is that you guys lost Cubans on Cuba,

even though I can look at that and say, what's wrong with normalizing relations? The people of Cuba don't deserve an antiquated form of government that has choked, the embargo has choked that country. They don't have it, they're stuck in the 1950s. Like I could want normalized relations there, but you guys didn't understand why my people wouldn't want normalized relations there.

No, I'm not saying that, I'm just saying over time, those policy changes went from whatever they were to like 25% worse in terms of approval. And I sort of had always hoped that the travel, the remittances, the person contact between people in Miami-Say or in Cuba, my over time make people happier. It might help them understand that, you know, the Cuban people were benefiting and it wasn't necessarily about the Castro's,

but I'm obviously not looking at this from the sort of identity standpoint that your parents are, or with that deep history of understandable hatred toward the Castro's. I'm truly stunned to hear you sound naive. I mean, you know, well, listen, I'm saying this is somebody who's trying to like learn from a policy change that I just hope would reach a younger generation of Cubans, even if their parents hated it, you know.

And sometimes things start out on the popular and they get more popular, but this one's the exact opposite. For now, I suppose, right, because I do think that all of this stuff changes with young people. If you can reach young people, I believe that the greatest hope for America, that I, when I don't see a whole lot of hope for what it is that's happening around us in terms of division and attacks on democracy in fact, the greatest hope articulates as well kids think differently yeah exactly exactly do you have any hope for the Democratic Party in Florida or we I mean they'll do the wrong thing I mean why would I why would I have any hope for that I mean

to Santa's no no no state I have seen recently. This is crazy. Tommy to see what's happened here in South Florida. I saw Memorial Day it has been an ethnic celebration a hip-hop celebration a long ocean drive for 10 years that has created a lot of fear and angst and police presence and I just saw it overrun by air and sea show and so much military presence that they have turned it into something entirely different that has run tourism out of Florida and tourism out of the South of Florida because of just how much fear there is of the other throughout Florida and it is such an effective Florida and it is such an effective, disappointing but effective political technique to just throw fear out there of other people, blame others for what it is that is happening. And next thing, you know, cries for equality sound like threats because you don't want

to hear them from black or brown or Asian or women. They just sound like threats to a white power structure. Yeah. And you've got some politicians down in Florida who are very good at singing those notes and those dog whistles and appealing to that kind of populist right wings or fear mongering. But how does it work? It always works?

We're doomed to always lose to that. I don't think we're doomed to always lose to that. I think it abs and flows. I think that when I look around the world, the 2008 financial crisis hit everybody hard, but hit some places harder than others, and the recoveries have been longer and slower than others. And that kind of economic pain and the subsequent inequality and inability of governments to get a handle on it and kind of build back

I think create a lot of space for right wing populism and demagoguery And the kind of politicians you were just talking about who were able to use fear to blame others and when you add on top of that mass migration flows. They're often the results of war or the Civil War and Syria or Afghanistan, et cetera. You find an easy enemy that you demagogue, that you blame for everything. And that's how these parties grow. And I think that you got to fight back,

but it can be very hard under these circumstances. You mentioned the joys and sufferings of having a sleepless six-month-old in the house. When you welcome a child into the particular America that you're welcoming that child into as you're fighting for things, what's the stuff that keeps you up at night about the future? There was another mass shooting the other day. I couldn't even tell you which one it was because there are so many of them.

And it was the first time I turned to Hannah and said, I could imagine us living in London or somewhere else so that we don't have to deal with this shit. That's what changes with a child, correct? Because there are all sorts of fears about climate change and democracy crumbling, but guns and the randomness of it when you care about something, I'm imagining the way you've never cared before, correct? Yeah, I mean, suddenly you're kind of the all the cliches are true, your heart is under sleep.

You're not in control anymore of your own soul. And it's two things. It's the randomness of gun violence and the trend of these shootings happening in schools, including elementary schools, and also just the absurd reality that the United States has more guns per capita than any other country. I think the second biggest is Yemen, which has been engulfed in a civil war for the last you know however many years um... and the inability or refusal of the republican party to just do some common sense things to get machine guns

off the street i mean it's it's um it's natting how have you been changed by the birth of your daughter other beyond the ways that you're articulating here? Before we had our daughter, before we had Lizette, I was not like a big baby guy. You know, you have a friend who had a baby, they'd be like, you want to hold him, you want to hold her, they're like, I know I'm good, they're kind of scary. Like holding a three-month-old, they just feel like you're going to drop them. That has completely changed for me. I love every second with her. I want to be around her all the time. I think about the future in different ways than I ever did before. It's also true that it was, we had a

hard time having kids. We went through several miscarriages. We actually had another daughter who was still born at six months and just sort of like the most devastating thing you could imagine. And so it has made me, being with her makes me more present. And I think more self-aware of what a gift she is and how many parents of 20-year-olds probably think what I would give for another day with this son or daughter as a six-month-old where, you know, I could just hold her in my arms and she can't argue with me. Or tell me, I suck or whatever it is we do once we're team interested. You have talked very publicly, vulnerably about those difficulties. Why do that? Roy Bellamy on our show decided that he needed to do that for some healing.

I don't think people understand. I don't think people talk enough about or understand the difficulties you're talking about there. Why did you decide to share that vulnerability with the internet? Yeah, you know, I mean, so Hannah, I went through several miscarriages. We did not talk about those publicly, but privately they were all consuming. And it impacted every night we went to bed, every conversation we had, every morning we woke up, it was just like sadness everywhere. And so I think for Hannah, you know, in particular, there was, I don't want to speak for her.

For both of us, I think there was a sense of embarrassment and shame and tragedy. For some reason, you don't want to talk about these things or you feel like a failure or you blame yourself in some way. And all of that is irrational and stupid. But then when we lost our daughter, Margot, at six months, people knew we were pregnant, there was no hiding it, there was no way to keep this a secret. And I didn't want to because I just sort of couldn't walk around all day thinking about one thing and putting up a brave face and talking about

another. It was just not. It was not an option anymore. And I also think that miscarriage and trouble having children is such a common problem, but for some reason people don't talk about it, and I don't really understand why. I think that makes it harder on everybody. It makes it this sort of private, lonely tragedy rather than an opportunity to have empathy and share and experience with other people, and we both just decided like we got it. We just can't keep this to ourselves. I don't think of you in many ways or your work

as a rational and stupid. So what is happening there that you were succumbing to a rational and stupid? Comparison ruins everything in life. I think you feel like it's your job to, especially for women, it's particularly hard for women, I think, that your job is to have a baby, to raise a child. And you feel like a failure if you have not. I know this is how Hannah felt.

And on top of that, once you start to focus on these things or want to have a kid, it's all you see everywhere is friends, your peers, your coworkers, Instagram, you know, people with their new babies, and you compare yourself to them, and it makes you feel worse. And I so I think that is where the irrationality and stupidity of it all comes from, the sort of the self-belame and criticism for something that's really out of our control. and criticism for something that's really out of our control. And how much joy is there now as a family that it would appear? I don't think I have this wrong that Daddy has arrived at his wildest dreams. And now from a happier place can take care of a family, a company, and a wife. Because what you're articulating, you don't need to

necessarily care about if you're building a cold company. What you're articulating about the managing of people is that crooked media simply will not be a caring company if you personally don't care about the people that you're managing. Yeah, I mean, it, you know, it's, um, it's an incredible place with incredible people who are well-meaning, who care about admission, who want to be part of something that hopefully, and even just a small way, can chip away at some of the problems this country has and make things a little better, can stand up for communities that are getting treated like punching bags by the far right, and to try to push the Democratic Party to do more, to help more people to win more elections and do the right thing. And so we are incredibly proud of this place

of the team that works here, of the work we do. And it can feel like a family in the office too. What a joy though, right? To feel like you're in the middle of a fight, but also that you're laughing the entire time, right? You're not. There are also tears and frustrations in everything else, but I imagine that the joys of laughing about where you've arrived with your friends. My guess

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

New episodes every Wednesday and PodSave America. New episodes, Tuesday and Thursday, wherever it is. You get your podcasts. Can you explain to the uninitiated again, just the difference between PodSave the World and PodSave America? Because PodSave America, as far as I can tell, represents the growth of your learning. Yeah, PodSave America is twice a week,

the biggest stories and politics from a progressive point of view. Positive the world is me and the guy named Ben Rhodes, who is my co-worker. We share an office at the White House actually, who worked on foreign policy. And we basically try to summarize the biggest stories happening in the world once a week in one episode and then talk to politicians activists, you know, global leaders, journalists to help people understand things that are happening outside of America. I love doing it.

It's really the highlight of my week. Thank you, sir. I hope I didn't get to, I didn't hope I didn't make you too uncomfortable. Not at all. Pressing in there on the family stuff. No, no, no, no. It's a, listen, it's not easy, but it's good, you know. And it's had happened.

I pretty, so I actually, it, when shitty things happen, I think people sometimes feel bad about raising it, but secretly everyone wants to talk about these things, right? Because I don't, I have not stopped thinking about her. Think about her every day. And so it's nice to be able to kind of honor that memory by talking about it. I appreciate you doing it here, sir. Thank you. Thanks, Dan. Thank you so much for having me on. I really appreciate it.