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JVL
Hello everyone. This is JVL here with my best friend Sarah Longwell, publisher of the Bulwark. It's not Friday. We just did a show last night. We're together, look like this, like grim death. We're in the same space and we were not going to do a show for the week, but I, I asked Sarah to do something because I think we have not done a just hangout show in a few years at this point where we just talk about stuff that doesn't have to do with the news and politics. And I thought it would be nice to do that.
Sarah Longwell
I like this idea in part. I do think this came to you because we did before the show, we did sort of a little Q and A with a group of people and they asked us not really political questions. I mean, some of them were political, but a lot of them were just about, you know, how things like what are funny things that happen behind the scenes about our relationships with each other, things about how the Bulwark works that I do think increased our appetite for maybe just talking about some of these things. It was interesting how curious they were about things that we don't always think about talking about. Yeah.
JVL
Yeah. Should I keep my hat on for the whole entirety of this?
Sarah Longwell
I mean, I think you should.
JVL
Is it distracting you?
Sarah Longwell
It's not. Doesn't distract me. I do think it clashes with that. What is now because you have gotten so skinny, that like terrible, terribly oversized vest and so it's very red and very blue.
JVL
I was, I was given this hat. It looks great and I want to rep it. I'll take it off.
Sarah Longwell
No, don't Take it off.
JVL
Just. Really?
Sarah Longwell
Okay.
JVL
All right, I'll leave it on. Maybe it'll look good in the two shots. All right. So we're just going to take turns asking each other some questions. And the first question I had for you was knowing everything that you know. Now, if you had it to do all over again, we jump back. You've just walked and gotten your diploma at Kenyon. What would you do differently?
Sarah Longwell
That's always a tough exercise when you're pretty happy with the place that you're in. And so you can say, well, here's this terrible thing that happened, or this thing that was derailing in some way. But of course, everything that you do layers up to where you are now. And I am like. I mean, the thing that I think hurts the most or, like, just is a tension that exists inside of all of us is the fact that the worse the world gets, the more audiences want us and the bigger we get and the more, um. Well, let.
JVL
So let me rephrase it, though. Are there things that you would have done that you think would have prepared yourself for this moment better? So instead of going to work for isi, maybe you go to law school? Because having a law degree maybe makes you feel like you are prepared for this moment in a different way?
Sarah Longwell
I wouldn't do that. Those three years at isi, it's funny, I was. When I was doing the interview with Sarah McBride last night at the show, she is the one representative from Delaware, which is she.
JVL
I didn't know that.
Sarah Longwell
Are you. That's okay. He's doing this bit because in the car on the way over, I was prepping for the interview, and I was like, hey, did you guys know that there's only one representative from the state of Delaware? And the boys both turned around and were like, yes, why don't you know that? And I lived in Delaware for three years.
JVL
You're the only one of the three of us who's lived in Delaware.
Sarah Longwell
No, I don't know. For some reason, I had not quite clocked that. She actually has quite a large constituency. And I gotta say that the three years, she was pretty. She knows isi, and she was pretty shocked to learn that I worked there because it's very conservative, very Catholic. There was actually the biggest tension at ISI was between sort of the intellectual traditions of conservative Catholicism and the intellectual traditions of straight conservative Christianity. And I spent the whole time being like, I gotta tap out of this particular conversation.
JVL
What are you people talking about?
Sarah Longwell
What is everyone? And I'll say, actually, Just as a personal thing, that happened when I was at isi. So those were the three years after college when a lot of people, I think, go live with their friends in big cities. And I was very lonely. It was where I had a job. I was interested in going and working in Republican politics or the conservative movement at the time. But it was also just kind of where I got a job as I'm graduating from college. And I, like, I didn't know anybody in Delaware. There weren't a lot of young people. And the young people were very conservative. Like, even the ones that I became quite close with would say to me, I couldn't come. Like, when I came out, sort of right before I left, or to the people I was closest to, there was a real like, well, that'll be so too bad I can't ever come to your wedding. And of course, they were. Many of them were getting married quite young or like, they're getting married at 24 or 25. And so I went to several of their weddings, which would lead to this conversation about how they couldn't come to mine if I got married. And so it was like a really painful three years. It was like a lonely three years. There's not a lot going on in Delaware. I would sort of drive up to Philly, and I kind of had to figure out how to both. It's just like, it's such a jolting experience after college where you're just surrounded by people of your own age cohort.
JVL
We have very different experiences of college.
Sarah Longwell
I guess, but, like, you know, I just had, like, a million friends. I went from having a million friends and people who were around all the time and an apartment full of people to, like, a stack of conservative books like Witness, you know, reading Whitaker Chambers and Friedrich Hayek. And, you know, it was even before, you know, this is 2002 to 2005. It's like when the gay marriage debate's really starting to happen. It's when I'm realizing I'm gay. It's when I'm going through the heartbreak of, like, my first relationship in college and having. And sort of moving on from that. And so, like, the really tough. But I think about a lot those three years how bad they were and how I wouldn't trade them for anything, because that loneliness was a time of, like, tremendous intellectual awakening. It's what I did so much reading. I had nothing else to do and. And I had to, like, figure out how to make the world work for me. I had to drive to Philadelphia and Be like, okay, I'm going to go to this lesbian bar and say hi to people. It's like, I don't know. So anyway, the point is, in terms of what, like, I do think that prepared me, like, I think the time with working for Rick Santorum and realizing that that was a really bad. And I didn't work for him, but the company published his book. And so I was just like on the book tour. And that was a miserable, but also very eye opening experience for me about the different strains of conservatism and which one I was, which was pretty socially liberal. And then because of the sornatorum stuff, I felt like I had this cosmic debt to pay. And so I went and I joined the Log Cabin Republicans and got involved in politics, mainly through making a conservative case for gay marriage, which also led me to a deep interest in persuasion work. And so, I don't know, I actually feel like all of that stuff is what prepared me for this moment. I gotta say, I think if anything, the thing that I wasn't prepared for, that I don't know how one prepares for this, is in all of those years, the people that I was reading, the people that I was investing in, the people whose worldview I was consuming as a way to formulate my own, most of those people went for Trump, and most of those people moved in that direction and abandoned everything that I had sort of taken in from them. And that was a tremendously destabilizing experience. And I don't know how I would have better prepared myself for that, other than if I had a much more grim view of people. Because obviously the one thing about me is that I just had different expectations for how people would behave when the moment like this came. I thought people would behave differently than they are, and I was wrong about that. Okay, so same question to you. Is there something that you wish. Do you wish you had gone to medical school now or law school?
JVL
No. I am very happy with my life where it is right now. I. I love being at the bull work. I love getting to do this with you every day. If I had known that we were going to inhabit a world where I had to, like, pick up this shield every morning when I woke up. There's no way I would have gone into political life if I had known that we were going to wind up in a place where, like, actual democracy was on the line and fascism was, like, pushing ahead in America. I honestly, I would have gone and figured out a way to get a post bacc degree and done research. Enough in a lab to get myself into some medical school somewhere. And no way I would have chosen this to. To be in a world where not all the people that I, you know, like, I. I chose the writing life. And at a moment right before the writing life got blown up by the Internet, I was reading all of these people who I greatly admired, and 75 to 85% of them turned out to be cretins who did not believe any of the stuff that they were. I mean, it has been a. And what's funny is that, like, up until 10 years ago, like, every single point in my professional life was fantastic. Like, I. I loved it. I just. I loved being in public life. I love the writing life. I love those things. But, you know, getting 20 years into that and then finding out that it's all a lie. And, oh, by the way, during what should be your most productive, the most productive years of your career, when you're able to do the best work because you have the combination of experience and knowledge, plus still a lot of energy, instead of thinking big thoughts, you're just going to wake up every day trying to get people to realize that there's fascism on the loose. I would never have chosen this.
Sarah Longwell
So it sort of leads to a different formulation of the question, which is like, I don't know, is it possible it chose you? I mean, I don't mean that in a fate kind of way. I sort of mean, like, sometimes I can look back and marvel at the experience that I had that produced a set of skills that I actually think matches what we're doing in the moment pretty well in a unique combination. And I would say similarly for you, I'm not sure, to be you, you have to have both. The combination of what is uniquely you, which is a somewhat, I don't necessarily want to say a bleak view of humanity, but I guess some skepticism, like, you think man is fallen, right? In this way, combined with an ability to crank out 2,000 words a day. Don't you have a sense of, if not you, who?
JVL
I don't. Honestly, I do it because I feel like it's the only tiny little thing that I can do to be one of 50,000 cogs in an ad hoc machine that's trying to turn back fascism. I would have been just as happy to have tried to add value to the world by helping sick people.
Sarah Longwell
And of course, we need people to add value to the world to help sick people, but I don't know, we also need people to diagnose accurately a sick country.
JVL
Well, you know, you just have to have had Tim Wright as well as podcast.
Sarah Longwell
Sure.
JVL
All right, what was my next question for you? This is about the Bulwark. So things are going really well for the Bulwark, as you said. This is one of the central tensions of. Of our time. The worse things get for America, the better things get for the Bulwark. Although in fairness, things are pretty good for America. During four years of Joe Biden, and the Bulwark grew like crazy. So it isn't really like. It's just that the Bulwark is still finding its audience. Like, we haven't come close to finding the top of that.
Sarah Longwell
I think that's true. Although I will say, I do think part of why we remained, well, I think we remained successful during the Joe Biden years for a couple reasons. One is just there's a high quality of work being done, and so I don't think that sometimes people try to put us in a box of, well, what would you guys do after Trump? As though these skills are only useful.
JVL
We did four years of that. It was awesome. We were all so much happier. We still grew. We still did great work.
Sarah Longwell
But we also knew. We also knew, in a way, I think the rest of the world didn't, certainly in the way that Biden didn't. And so there was an audience that also found us during those years of, no, these guys know we're not done yet. These guys know it's not over. And I think we saw the ability of Trump to resurface, if not Trump himself, certainly the forces he had unleashed on our politics.
JVL
So my question is, when you look forward for, for us, the Bulwark, what worries you the most?
Sarah Longwell
Like, for the business pick?
JVL
You tell me.
Sarah Longwell
I mean, look, we're going through a growth spurt right now, and both in terms of the audience that's finding us, but then that means the scale of the operation has to get bigger. We believe that we have a mission that not just a business. And so we look for other people who are kind of either on that mission or can enhance the mission that we're on. We're chasing more audience and more influence because we want to have this impact on the world. We want to change people's minds or we want to let people. We want help people see more clearly what is happening in the moment. And so, but, like, we were a scrappy little team with a mission, and, like, we have to grow into a business that functions well. And, you know, you and I were just in a very long meeting right and it's always about. It's about how you add all kinds of things that will make our business better and all the things we need. And I think the thing that I find hardest is because I do have more of a business background, I'm not uncomfortable with the idea of scaling and figuring out how to get bigger. I do just want to make sure that we are able to always be a mission and a lot of places. And look, I don't want to debate the Bari Weiss of it all, but people want to. When you are a business, people come wanting to figure out, well, hey, you know, you guys could be more profitable if you did this. Or, like, you know, somebody could buy you or. And you could all make a ton of money or you could, you know, like, there's just all these ways in which a business can operate and you want to sort of. I, I don't. I don't want to just be a business, right. And I don't want to let anybody turn us into just a business where we are chasing the things that I think people who are in business chase and who, when they do that, sacrifice really important things about what they were supposed to be doing. And so I think, yeah, I think just, I want to make sure that you have to hold both where you get big enough to have as much influence but not have people be like, okay, well, if you want to get big, you've got to do all of these things that a good business that would be growing would do. But in doing so, you lose both the mission, the secret sauce, the reality of. And so, like, I'm trying to. And, you know, this is like, we talk about this, but it's like, we want to make sure we do both.
JVL
Well, yeah, I'm sorry, I have to take the hat on. I'm just feeling self conscious about myself just sitting here with it. I'm just like, it's too big, it's too blue. Everybody's staring at it.
Sarah Longwell
I'm just gonna look at your forehead now.
JVL
That's fine.
Sarah Longwell
What do you worry about? Because this is the Bulwark has been successful beyond your imagination. But I also know, and I don't think I'm giving anything too much away by saying this or betraying any confidence.
JVL
But like, hey, fam, it's jvl. This is the secret show that Sarah Longwell, my best friend in the entire world, and I do two best friends talking about the absolute end of democracy in America. I mean, what could be more fun than that? If you want to hear the rest of the show though. Got to subscribe. Come and support us at the Bulwark. We're all in this together.
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Hosts: Sarah Longwell, Tim Miller, and Jonathan V. Last
Release Date: October 11, 2025
Podcast by: The Bulwark
In this unique “Secret Podcast” episode, Bulwark veterans Sarah Longwell and Jonathan V. Last (JVL) set aside their usual political analysis to reflect candidly on their personal and professional journeys, the evolution of The Bulwark, and what it means to find success as the world seemingly veers into crisis. The central theme explores the irony and tension of personal and organizational growth amidst national and political decline, with revealing discussions about values, career choices, and staying true to mission over business or profit. Notably, Tim Miller is referenced but does not actively participate in this episode.
[01:04–02:34]
[02:34–10:12]
[12:24–14:15]
[14:22–19:03]
[02:12, 19:03, 19:14]
Sarah Longwell:
JVL:
| Timestamp | Segment | Notes | |-----------|--------------------------------------------|---------------------------------------------------------------| | 01:04 | Show premise & break from politics | How the episode’s “personal” tone was selected. | | 02:34 | Sarah’s career path & conservative circles | Effects of early work at ISI and grappling with identity. | | 06:49 | Intellectual awakening & loneliness | Sarah’s post-college transformative years in Delaware. | | 09:20 | Betrayal by conservative mentors | Sarah on pain of seeing mentors support Trump. | | 10:12 | JVL’s hypothetical: alternate careers | JVL considers medicine if he’d known the future. | | 12:24 | Reflection on fate and preparation | Is this work a calling, or a product of unique skillsets? | | 13:35 | “Cog in the machine” comment | JVL on his personal motivation for continuing the work. | | 14:49 | Bulwark’s growth—Biden and Trump years | Rebutting the “Trump-only” relevance. | | 15:54 | Concerns about scaling The Bulwark | Sarah on mission vs. business tradeoffs and “secret sauce.” | | 18:40 | Commitment to balance | How leadership preserves both mission and sustainable growth. |
The tone is frank, vulnerable, occasionally humorous, and marked by a sense of mission beset with ironic frustration. Both hosts blend warmth and seriousness, deftly balancing light candor with the existential stakes of their roles as journalists in troubling times.
This episode is a rare, introspective detour that humanizes The Bulwark's key personalities. It’s ideal for listeners curious about the humans behind the headlines, the ethical dilemmas and emotional labor involved in a mission-driven newsroom, and the paradox of finding “success in a failing country.” The candid discussion offers insight into both professional and personal navigation of tumult in the political and media landscape.