Podcast Summary: "The Best of SBS: Pod Save America's Jon Lovett & Tommy Vietor"
Podcast: The Dan Le Batard Show with Stugotz
Guests: Jon Lovett & Tommy Vietor (Pod Save America/Crooked Media)
Date: November 27, 2025
Location: Elser Hotel, Downtown Miami
Main Theme:
A candid, revealing conversation with Pod Save America co-founders Jon Lovett and Tommy Vietor, exploring their winding career journeys from politics and comedy to founding one of America's most influential progressive media companies. The discussion dives into ambition, validation, career pivots, founding Crooked Media, leadership, and how personal challenges reshape purpose—with a healthy dose of humor and vulnerability.
Table of Contents
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Jon Lovett: From Stand-Up to Speechwriting to Crooked Media
- Early Years & Insecurities
- Speechwriting and Comedy Crossroads
- The Leap to TV and Hollywood
- Founding Crooked Media (“Pod Save America”) (21:05)
- Anger vs. Inspiration
- “Cooking” and Growth
- Body Image, Therapy, and Self-Acceptance
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Leadership, Purpose & The Fight for Decency in Media
- Building and Leading with Friends
- Imposter Syndrome, Self-Doubt, and Company Culture
- Navigating the Politics of Sports and Media
- Joy, Gratitude, and the Weight of Responsibility
Jon Lovett: From Stand-Up to Speechwriting to Crooked Media
Early Years & Insecurities
- Lovett describes his post-college days: “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.” (01:53)
- He reflects on his search for validation and uncertainty about direction:
“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…” (02:36)
- The roots of “needing praise and attention” came from both temperament and growing up closeted in a “career driven” Long Island community.
“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.” (06:08)
Speechwriting and Comedy Crossroads
- Lovett’s entry to Capitol Hill was part fate, part following a thread:
“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… I had actually written some jokes for her…they asked if I would write some jokes for Hillary Clinton.” (04:10)
- He almost went to law school, but bailed at the last minute, driven by intuition, not conviction:
“I withdrew, not talking to anybody. This doesn't feel right. I'm going with intuition here.” (05:51)
The Leap to TV and Hollywood
- After speechwriting for Hillary and then Obama, Lovett faced imposter syndrome but recognized “the perks of being a fast writer,” especially in high-pressure situations. (13:48)
- On jumping to Hollywood:
“The biggest risk I took was after three years of being a speechwriter…leaving 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.” (09:28)
- Developing NBC’s “1600 Penn” was exhilarating but overwhelming:
“It just worked and NBC wanted it... I was completely overwhelmed. I didn't know what I was doing.” (12:53)
- Lovett is candid about learning on the fly, faking confidence, and feeling like an imposter:
“For 1600 Penn, imposter. I could fake it till I made it. I learned a lot. I could get through it...” (13:48)
Founding Crooked Media (“Pod Save America”) (21:05)
- The aftermath of Trump’s election was the crucible for Crooked Media. Lovett, Favreau, and Vietor felt a “mission”:
“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…” (21:55)
- Crooked Media emerged from a gap its founders saw between media and activism, and as a direct response to right-wing media:
“We did want to create a media company that said, hey, 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…We're going to remind everyone that they are participants and that it's not a game.” (22:16)
Anger vs. Inspiration
- On motivation:
“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…” (25:13)
- Lovett resists the demand that politics be “inspirational spectacle”:
“It is the kind of end result of several decades of political punditry that treats everybody watching like they are fully, fully cognizant, fully informed observers who can't be persuaded…” (25:13)
“Cooking” and Growth
- Lovett talks openly about personal development and where self-acceptance meets self-improvement:
“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's cooked all the way through. You put the fork in this part, it comes out clean.” (39:29)
Body Image, Therapy, and Self-Acceptance
- Lovett is vulnerable about body image struggles:
“Tons. Still do. A huge problem for me. Huge, huge.” (40:47)
- He discusses medication and therapy:
“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… 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.” (40:56)
- Offers a tongue-in-cheek “Cool-Boar” matrix to measure charisma and gregariousness. (42:06)
Tommy Vietor: From White House Aide to Media Entrepreneur
Entering Politics by Accident
- Vietor sees his path as a succession of lucky breaks:
“So much of life and my, you know, career has been luck and timing and basically I graduated from college in 2002. I interned for Ted Kennedy… I didn't get hired, and I was completely devastated. But not getting that job led me 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…” (51:54)
White House National Security Years (51:54)
- Top Secret clearance, “learning” from the best minds in government, and being a bridge between experts and the press:
“Came associated with that comes a top secret clearance and the ability to go to really interesting meetings… and help them or ask them to explain things to me so that I could explain them to journalists…” (52:47)
Post-Obama Existential Crisis and The Pull of Media
- After leaving the White House, Vietor wanted out of politics but found himself drawn back:
“I thought to myself, I've been on this Ferris wheel, this merry go round for about nine years, working for Obama. ... It's time to do something else with my life… I tried. I did it for a couple years, but it didn't stick…” (55:01)
Crooked Media’s Activist Vision (61:17)
- Crooked aimed to mix facts and activism with humor and hope.
“That recipe [from right-wing radio] 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 conversation. …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. …also to make them not feel hopeless.” (61:17)
Management, Burnout, and Finding Fulfillment
- Growing the company meant a crash course in management, a role Vietor felt unprepared for:
“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…” (56:11)
- On burnout and the emotional toll of leadership:
“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.” (57:07)
- Family shaped everything:
“I just can't imagine doing that job [White House] now. If I don't get home before six, I don't see her that night…” (71:09)
Vulnerability, Family, and Personal Loss
- Vietor opens up about personal tragedy, miscarriages, and stillbirth:
“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. …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.” (82:40; 84:19)
- On comparison and self-blame:
“Ruins everything in life… 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 co-workers, Instagram, people with their new babies and you compare yourself to them and it makes you feel worse. … self blame and criticism for something that's really out of our control.” (86:05)
Leadership, Purpose & The Fight for Decency in Media
Building and Leading with Friends
- The complexity and risks of turning friendship into business:
“Every once in a while you have to scream at each other and fight it out and then, then get over it like a sibling. I do think it's more like brothers than, than friends or business partners at this point.” (67:45)
Imposter Syndrome, Self-Doubt, and Company Culture
- On never feeling secure, even at the top:
“Every time we do, like 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. …just a constant imposter syndrome, wondering when the audience is just gonna go away.” (75:03)
Navigating the Politics of Sports and Media
- Le Batard discusses the risks of speaking out (“stick to sports”) and the pressures on corporations to remain apolitical:
“I'm not competitive that way. So that's not where regret or doubt would seep in. It's on the hardest days when I feel like managing of people is hard. And I never, never envision myself as any kind of manager of people…” (75:42)
- On the challenge of being overtly political in sports media:
“If you just stick to sports, you're not going to. … But all I think I've ever advocated for, which is now somehow a controversial position, is how about equal and decency for all?” (77:59)
- Vietor: “...what value people in sports have for all of this stuff. …I'm glad it doesn't [work on the left]. I think the more progressive side is motivated by things being funny, inspiration, more fact based conversation.” (78:30, 61:17)
Joy, Gratitude, and the Weight of Responsibility
- On reflecting and gratitude, Lovett warns against pride:
“I think taking too much esteem from that is the wrong thing to care about. …I think that's the wrong kind of pride for me, maybe because I feel like I will take too much from it.” (45:50)
- Favreau frames the joy of the journey:
“There is. It can be all of these things.” (47:43)
- Vietor closes with hope:
“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.” (88:43)
Notable Quotes & Timestamps
- [02:36] Jon Lovett: "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."
- [04:10] Jon Lovett: “So they asked if I would write some jokes for Hillary Clinton. ...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.”
- [25:13] Jon Lovett: "Anger is my motivation. I'm not a hope guy, I'm an anger guy. I'm motivated by anger, always have been."
- [39:29] Jon Lovett: "This part's cooked all the way through. You put the fork in this part, it comes out clean."
- [51:54] Tommy Vietor: “The White House. The White House. I mean, I think so much of life and my, you know, career has been luck and timing...That little piece of luck led all the way to the White House and sort of a completely improbable journey.”
- [56:11] Tommy Vietor: “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…”
- [86:05] Tommy Vietor: “Comparison ruins everything in life… once you start to focus on these things or want to have a kid, it's all you see everywhere …and it makes you feel worse...The self blame and criticism for something that's really out of our control.”
- [88:43] Tommy Vietor: “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.”
Final Thoughts
This episode is a revealing meditation on ambition, accidental success, self-acceptance, and the challenge of using media for pro-democracy activism. Jon Lovett and Tommy Vietor’s honesty about insecurity, imposter syndrome, the grind of growing up, managing friends, and personal pain creates a tapestry of modern professional life that will resonate with listeners far beyond politics or podcasting. Their journey, as described, is less about a grand plan than about seizing opportunities, finding unlikely joy, and fighting fiercely—and often humorously—for what feels right.
To experience the vulnerability, insight, and punchlines for yourself, listen in especially to:
- [21:05] Lovett on founding Crooked Media
- [61:17] Vietor on Crooked’s activist vision
- [84:19] Vietor on sharing personal loss
- [88:43] Vietor on the joy and overwhelm of their mission