Breaking History - BONUS: Conversations with Coleman & Bari Weiss

Episode Date: June 11, 2025

 We’re sharing the latest episode of Conversations with Coleman, a podcast that joined The Free Press network this week. Coleman Hughes engages deep thinkers and curious minds in sharp, surprising, and unfiltered chats. In this relaunch episode he sits down with Free Press founder Bari Weiss and asks her about her critics, rising antisemitism, the woke right, and more. Hope you enjoy it & stay tuned for more Breaking History here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Hi, Poppy here, one of the producers of Breaking History. Our next episode is going to be about the origin of conservatism in America. It'll be out on the 18th of this month and it's really fantastic. You won't want to miss it. But in the meantime, we're sharing the latest episode of another show, Conversations with Coleman, a podcast that joined the Free Press Network this week. Coleman Hughes engages deep thinkers and curious minds in sharp, surprising, and unfiltered chats. In this relaunch episode,

he sits down with Free Press founder, Barry Weiss, and asks her about her critics, rising antisemitism, the woke right, and much more. Hope you enjoy it and stay tuned for more Breaking History. Welcome to another episode of Conversations with Coleman, now produced by the Free Press. If you're a long-time listener and don't know much about the Free Press, this episode will give you great context, because I'm interviewing its founder, Barry Weiss.

Most of the conversation is about her vision for the FP as an institution, where she thinks it fits in the modern media landscape, how her vision has changed over time, and how she plans to execute that vision. We also talk about her position on the Trump administration and her ongoing concerns about antisemitism. So without further ado, Barry Weiss. ["The Daily Show Theme"] Barry Weiss, thanks so much for coming on my show.

Coleman Hughes, so excited to be here. All right, so you probably don't need an introduction or a backstory on this particular podcast for many reasons, but let's just start with the origins of the free press where my podcast is now produced. Do you remember, was there a specific moment Let's just start with the origins of the Free Press, sitting across from you and in the free press newsroom. It's extremely exciting for me. Um, just a huge admirer of yours and very, very excited to have you in the mix. Um, when I left the New York times, I had absolutely no plan at all. All I knew was that the thing I had seen was intolerable to me and that I didn't

want to be a fig leaf for something that I felt had become sort of corrupt and most fundamentally that like the whole reason I became a journalist was to pursue my curiosity and if I wasn't going to be able to do that, what was the point? In retrospect, when I wrote that viral resignation letter, I like should have had a little widget. It was like, give me your email and follow along to see what I'll do next. The business would have been much further along by this point had I done that.

Instead, what I did was commenced a strong diet of day drinking and telling Nellie that anything short of like becoming, like building a world-changing empire was sort of going to be too small. Like I felt like I had seen this, I had seen such an enormous problem and the solution had to feel equally enormous. And so for a while that paralyzed me, to be honest.

And any suggestion that anyone had, like, oh, I should pitch a show here or try this there. And it was like, it's too small, it's too small. And then finally Nellie convinced me to do the smallest thing of all, which is start a blog, a Substack. She created the landing page or whatever. I would never have known how to do that because I'm a Luddite. And I wrote the first post for what was then called Common Sense, which was a personal blog on a flight to Miami. She was still at the New York Times and she was doing a piece about how Miami and COVID was becoming like the new Silicon Valley

that never really happened. And I wrote the post on the plane. And then what shocked me is that within maybe a few weeks, I was making more than I was at the New York Times. I think my salary when I left was like $115,000, which felt like a lot at the time. And what astonished me even more was that pieces pretty quickly were getting more traffic

than they were at the New York Times. And startup founders talk about this thing called product market fit. I had no idea what that was. I just knew that the more I was doing of the thing, the bigger the audience got. When I look back, I wrote like a memo at the time to some people that I trusted sort of talking about what I ultimately wanted to do.

And I had occasion recently to revisit it and I'm down the path of doing some of those things. I think we have, we do have a thriving newsroom and an incredible subscription business, but the free press is at the very beginning of solving the problem that I felt like I peered into at the New York Times. And so ultimately, if you told me that five years from now, a few years from now, that we would be in book publishing, in producing and making our own documentaries, and maybe movies and television shows, that we had not just incredible debates

that we do a few times a year, but an ongoing thriving events business that we maybe even had a physical space where like-minded, curious, intellectually open people would go to. You could find all of that in a memo I wrote in like the summer of 2020 after I left the New York Times. That's a long way of saying that the ambition

that I have for it is as big, if not bigger, than in the days when I was sort of like drinking Negronis and paralyzed. It's just, I kind of figured out that you don't like, you don't create an empire overnight. You have to like take small territory and do, there's a phrase that my friend Jessica Lessin who runs the information taught me, which is like earning your right to fight

the next round. And that was just extraordinarily good advice. So it's like, okay, master this one thing, make sure that you've killed it and maintained your standard of excellence and integrity and then go on to capture the next hill. And so yeah, that's, that's where you find me right now. Yeah. So if you think about who the prototypical free press subscriber is, how would you describe that person?

And do you think that audience profile is the same in 2025 as it was a few years ago, or is it changing at all? Well, it's changed a lot because to be blunt, the free press began as a reactionary product. Like I saw the excesses of the liberal left and it pissed me off because it was making my own life harder. And I felt like was swallowing so many things

that I loved and cared about. And so the stories that I ran at in the beginning were stories that spoke directly to that. And so, you know, in the beginning it was tons of stories about what came to be called institutional capture, whether that was in schools or in newspapers or in media. Four years later, I think it's been four years, I've lost track of time, the free press, the burdens and the obligations of it are extremely different. If you are a sideshow to someone,

like not a sideshow in a negative way, but if you're like the spice on the side of someone's diet, but they're getting their main meal at the Washington Post or the New York Times, that's one thing. What's changed is that the audience has said to us, no, no, you guys are like my main thing. Like I'm coming to you at 6 a.m. to read the front page,

and I want to get a holistic sense of what's going on in the world. Well, we weren't built for that in the beginning, and it takes a while to build up to that. And so that's one thing that has changed. I think we've gone from being a reactionary product that did six or seven topics really well to understanding that what the audience is asking from us is so much more than that. And so, you know, over the coming months, you know, what does free press health and

science looks like? What does free press technology and business coverage look like? What does free press economic coverage look like? We're still going to do the kinds of themes and stories that we began with because they're still urgent and important, but we've had to just really build out the breadth of what we cover. As for who the audience is, I would say, and I think this is still true, I would say like the beating heart of our audience are people that think of themselves as liberals, classical

liberals, centrists, center left, even center right libertarians who feel disaffected and cast out or alienated by, let's just call it wokeness, that came to capture things that they regarded as sacred and important, whether they're institutions or culture. So that I feel is still very much like the absolute, if you asked me like what is the core free press persona, I would say it's a disaffected liberal in a hyper woke environment, but it's also a lot of other people.

And this is both the bluntly like the huge opportunity and challenge. I could tell you like, you know, there's a lot of NeverTrump publications out there that are thriving and successful. And I'm a reader of many of them. They have a very, very particular niche audience. Ours is much wider than that.

So it's like, we're both read by people in the Trump administration and we're read by people that were pilloried or cast out or despised the Trump administration. We are read by people in Manhattan and Los Angeles We are also read by farmers in Iowa and homeschooling moms in Texas Like it's a very much like here comes everybody's like so I imagine like it's not a niche audience And so that that's both an incredible opportunity, but it's also a challenge for us

I think it's it seems to me. It's also a challenge because the coalition is unique. It's not, if you try to name another publication with the Free Press coalition, I'm not sure you come up with any. No. And so I think, you know, when you look at the way other people view the Free press that are, in other publications, whether it's NeverTrump publications or left-leaning publications, I think they have, like, if they're going to have an opinion on the free press, it's not the same as a stock opinion they have of a lot of other places.

It's unique to the free press, but it's also this thing of, I sort of don't know what to make of it because it's a new kind of thing. Yeah. And... It really, really frustrates a lot of people. That's exactly what I'm getting at. I think the result of that is very few other publications are going to have just a stamp of approval on the free press because there's nothing else, there's not many other things like it.

There's no one in your camp in some way, no other major publications in your camp. I think what makes the free press unique is very much typified by the kinds of people that choose to work here. And we took a straw poll, I wrote a little bit about this two weeks before the election, we were on like a staff retreat, we were literally stuck on a boat, we were going around the Statue of Liberty, which was incredibly fun. And it enterprising podcast producer was like,

I'm going to take a vote because we're two weeks ahead of the presidential election. And I honestly did not, I did not know what the outcome of that vote would be. And I was sort of like quite nervous because I was like, is everyone here going to be like an RFK write-in secretly and I didn't know it? And it was a third for Trump, a third for Kamala, and a third were either writing in or not voting. There's no other newsroom like that in the country. That I'm 100% sure of. And in that, I think we're very much a reflection of the country and also of our readership.

I'm extraordinarily proud of that because I've been in many monocultures in my life, having worked in American newsrooms, and you kind of lose your edge when you're working alongside people that all think the same way. And so A, I think it keeps all of us on our toes in the most positive way. B, I think it models the bigger set of values that we're trying to stand for in the world. So, like, what does that mean?

Like, I think the average free presser, and they come up to me and say this, and it's kind of, it's very gratifying because they're reflecting to me an implicit value which is they say, you know, hey, I'm XYZ, I lean this way politically. I don't always, they always say this, I don't agree with everything that you guys run, but I know that's the point and I come away smarter from having read the kinds of pieces that you run. I'm just very proud of that and I think, you know, at our worst, and there's many criticisms of us, we have blind spots.

We're also in nascent newsrooms, so there's just like whole areas of the world that we're not covering yet. But at our worst, we have blind spots. At our worst, you know, we become parodic and can repeat the kind of same themes. At our worst, we're, you know, contrarian for the sake of being contrarian.

I know all the criticisms. At our best, I think contrarian for the sake of being contrarian. I know all the criticisms. At our best, I think what we do is give people the strongest argument on both or multiple sides of an issue. Right. And in a country where it feels like a thousand years ago, the idea of RBG and Scalia going to the opera together, being best friends, that is like a vestige of an America that feels to many people out of reach. We're trying to revive that and actually reflect that in the way that we conduct ourselves in the world and in the kinds of pieces that we run. The audience ultimately will judge whether or not we've

fulfilled that mission, whether we've lived up to those values. So the idea of having a newsroom that's one third for Trump, one third for Kamala, one third other. I should say, I didn't give anyone a litmus test when they joined. I think that's fantastic. That's why I feel my values are aligned with the free press. That's fantastic. That's why I feel my values are aligned with the free press. I think if you spoke to a lot of people at other newsrooms, many of them would say, I'd love for my newsroom to be like that actually.

Many of them would at minimum pay lip service to that. But then the next question would be, how does that survive practically? Because once you have people that feel strongly on different sides of an issue in an office, How does that survive practically? Once you have people that feel strongly on different sides of an issue in an office, I mean we've seen this meltdown after meltdown after meltdown at different institutions, there's a certain gravity where it has to go one way or the other because people can't tolerate each other. That's the fundamental problem.

So how do you, as the head of the ship, avoid a mutiny in one direction or the other? How do you keep people getting along? Is it a matter of who you hire? I mean, part of it is... It's a very self-selecting group that comes to work at the free press. In the same way that I think our audience is self-selecting. In other words, there are many places, and by the way, I'm a reader of many of them where when I want to just like get the rage at Trump going, like I know where to go for that.

You know, if I want to get the rage at Hamas going, I know where to go for it. Like meaning there's virtue in that kind of predictability and virtue in the thing that I think a lot of people are craving in this moment, which is the warmth of being in a space where you know that your priors are gonna get affirmed to you. What we're trying to do here is something very different and it's quite challenging. It's challenging for the reader and it's challenging

to work in an environment, I think, for some people like that. So, you know, people ask, like, how have I hired for the free press? They've hired themselves in the sense that, I would say most of the people that work here wrote me a cold email or reached out to us in some way and kind of self-identified as a free presser in all of the complications of what that is. Now, obviously the thing I wake up

thinking about, not the first thing I wake up thinking about, but every day I'm thinking about this question. You know, like my nightmare is to either replicate or fall victim to the exact type of thing that I experienced at the New York Times. So part of the way that we do that is be extremely explicit about our values. Part of the way we do that is, it's like working, it's almost like a muscle, being in conversation with people that you disagree with,

but then having a beer with them at the end of the day, like, that's not a natural, I don't know if that's a natural thing to human, like the natural thing as humans is just like, go get with your little tribe and get with the people that agree with you and like, beat your chest and feel good. So the thing we're trying to do is very hard. And, you know, again, to me, it's all in the practice. It's not like I had a litmus test to hire people.

I don't know if three years from now, it'll be exactly the same breakdown. I don't know where the country will be in a few years from now. What I can tell you is that it's really, really working right now. And part of it, I think, is if you ask people, I don't know, I could talk about that. I think about it a lot. I would say one thing that I did

not expect, but that a lot of free press people, readers and staffers have in common is I don't want to say that they're all religious, but I would say that there is a deep sense of values that people here actively talk about. Often, and often that is a religious person. Like there's a lot of conversation. I don't want to say necessarily about God, but sometimes about God, certainly about the idea that the world is disordered, the culture feels unraveling,

and what's the kind of wisdom and connective tissue that like is bigger than the politics of the day, is bigger than a lot of the things that feel like they're tearing us apart. And I would say that that is like an active conversation here in a way that I've never experienced in any place I've ever worked that I find is like very, very generative and really healthy. Okay, I'm going to read some of the criticism

that the free press has gotten recently from no less than Andrew Sullivan who I admire for a long time and I think is brilliant. But here's what he says about the free press. It goes, quote, I just made the mistake of looking at the publication that with increasing levels of nerve calls itself the free press. The almost total avoidance of coverage of the current government threats to freedom as basic as habeas corpus, due process, and free speech on campus is quite something. And when there is coverage, it's nitpicking in order to defend Trump.

Did they mean none of it? As in, did they mean none of it in their commitment to free speech and so forth? I agree with you that Andrew's brilliant. And so I don't want to say that I dismiss his criticism. I take it seriously. He's a person that Nellie and I have spent a lot of time with. And I wish he had called me and talked to me about that before he posted it, but I did see it on the internet as well. Look, Andrew is someone who, like, when he gets an idea in his mind, he really sticks to it. I feel a little bit like the free press is like the Trig Palin of the moment for him. I don't know if you remember his obsession.

He got obsessed with the idea that Sarah Palin was not actually the mother of Trig. What I'll say is I genuinely don't think he's reading what we're putting out there. It may be true that if you look, like do we have an anti-Trump piece that is sufficiently rageful or sufficiently passionate to Andrew's satisfaction every single day? No. But if you look at the kinds of pieces that we've done, I mean, who can look at the piece

that we ran recently about Qatar and Qatar's influence over the Trump administration and more broadly over America and like what's more serious and more lasting that or an 800 word op-ed saying Donald Trump is a threat to democracy. Who could look at the, you know, we ran a symposium recently on whether or not we were in a kind of constitutional crisis moment from some of the most like pedigreed and celebrated originalist judges and scholars in the country. Again, what's more effective that or an op-ed by, I don't know, Jen Rubin. We ran an essay, a really important essay recently by Rod Dreher, who's extremely close

to JD Vance about his concerns about this administration. I just like, I could go on like that with like lists of dozens and dozens and dozens of stories that we've published since Trump took office. I just think that for people maybe that are encountering like a headline on Twitter or a piece. We're just publishing so many pieces a day, perhaps they're not reading us carefully enough. Yeah, I agree with that. I also think it's really shitty

when a friend doesn't contact you first. Because I think, yeah, just call me up and yell at me and we'll talk about it. And if I tell you to fuck off, okay, well then go to Twitter. But that's a personal code of mine. One thing that I do really pride us on, we don't always do this, but doing our best, is when people come to us with criticism, it's not even that we take it seriously. Often it turns into a piece itself. And sometimes that's a letter to the editor, but you would be shocked by the number of pieces

that we've run that have begun with an angry text or voice memo or email to me. And, you know, again, like, and I think that it, I think that it catches people off guard because they're so used to like, just like screaming into the void. And it's like, no, no, if you have great criticism and you have productive criticism that you feel that we feel would make us better and our understanding of the world better, we

take it very, very seriously. I think one of the things that's hard and that I'm really trying to practice is, and I'm sure you understand this Coleman, is when you've been online for a really long time and you get a lot of really irrational hate coming at you, it is very tempting to just like plug the holes in your ears and cover your eyes and like wish away all criticism as straw man, like hateful, tuning it all out.

It's a very hard thing to tune out the irrational deranged hatred, but also make sure that you are like getting useful, constructive feedback and criticism. And that's something that like I'm, I am struggling with a lot. And that's one of the reasons why I find it so important to be working with people that see the world differently than I do. Because I know that when Joe Nassarra comes to me with criticism, I know he's giving it to me,

or giving it to the publication, with the best of possible faith. He works here, he wants it to be great. And I think, you know, that's one of the things that I think keeps me honest. But I would say for anyone that's been online and has been like getting punched in the face for many, many years in a row, it's a muscle that like, it's a practice that you need to maintain. Definitely. Do you believe in God?

I do, but like, I have such an, if you ask me the second follow-up question, which is like, what do I mean by that? Like, I don't feel like I have a sophisticated answer. So then what does it mean to you to say yes? Why is it important to you to say yes, as opposed to no or I don't know? Maybe, it's definitely not a no, but it's more than an I don't, it's more than a I hope or I don't know.

I think part of it is just a visceral feeling that I have, and I feel like has deepened as I've gotten older. I think part of it is just maybe a yearning for God that is not proof or disproof, but that's the reason that I just say yes. Part of it is very much a view that without God, I'm not sure. In the end, we just did a really great debate on this and I felt Ross Delfit was very convincing. I don't know how we get to all kinds of other things that I believe in. Like the idea that we're all created equal because we're all created in God's image.

How do we get there without God? So you could say that my answer for godness or belief in godness is kind of thin or utilitarian. I don't know. I feel like it's an emergent thing for me. Yeah. What about, I'm just curious, yes or, is it a yes or a no or maybe? It's probably not, probably not. But, like, I think I would count as an atheist, for sure, but I don't at all discount the idea that religion can be good, not just for individuals, which is obvious if you've ever met someone, you know, millions of people across the world that were alcoholics, drug

addicts, you name it, until they found God and now they're just sweet, lovely people. So to go up to such a person and say, did you know God probably doesn't exist? And I just read Richard Dawkins. Yeah. You can be right, but I don't see how that's helpful or, to me, if faith works for you, then you should do faith. Because you've only got one life,

and as long as it's not harming anyone else, I don't see how it's harming me. So I actually recommend that people do faith and religion if it works for them and doesn't harm other people. I don't think you should be an atheist just because that's probably the most intellectually defensible position, nor do I think a community that's super functional, because it's centered around a benign faith, should let go of that faith if it's working for the community. So, I think the only critique I have of the famous atheists that I agree with them down the line on almost everything, except for that I take very seriously the research, which is not ambiguous at this point, that religious people are happier.

Conservatives are happier than liberals, which could be a side effect of religion. I don't think we know why, but there's no rule that says, But there's no rule that says, you know, having the truest, most scientifically defensible beliefs is equal to living the happiest life possible or living a good life. Yeah, there's no rule. I don't think there's any reason that that has to be true. And so if I get evidence that maybe it's not true, you've got to take that on board. To me as an atheist, you have to seriously grapple with that question. I think also part of the reason that this question is particular when you ask a Jew this question is because so much of Judaism is about acting as if, like I try and live my life as if God exists. There's this idea, there's this sort of famous line

from the Bible of, it's, it's, we will do and then we will understand. And the idea behind that is like, you do all these things. Or as my dad likes to say, it's like a good program. Like it's a good program for a meaningful life, a meaningful family life, a way of marking time, a obligation to do right and pursue justice in the world. And so, for me, I think it's part of the reason I say yes is because I want it to be a yes,

because I try at my best to live my life as if there is a God. But I don't know, it's probably something I should talk to a rabbi more deeply about. I think that's what RFK Jr. said about getting off of heroin. I don't know if you ever saw that interview he did. Yeah, it's actually one of the few really personal interviews he's done about his whole past and all his craziness, is that the advice that brought him to religion was to first do the stuff and then see how you feel and how you believe after a few years of doing it.

Which is counterintuitive, but it actually makes sense because this actually goes back to what I said a second ago. If you start doing faith and it works for you, you just notice you're waking up happier every day, who at that point would then question whether the faith is working for you, right? It's similar to, you mentioned Ross Douthat. So Ross struggled, he wrote about this in his book,

struggled with Lyme disease and chronic pain and just awful, awful ailments. And he tried everything, tried Western medicine, everything doctors gave him. And then he started doing these crazy quack stuff, sound therapy and blah, blah, blah. But it worked. His pain was gone. So my view is that every single one of us, if we're in, whether it's physical pain or emotional pain, and you start doing something that is not hurting anyone, that you're just immediately happier and your pain goes away, no one at that

point is going to question whether the thing is legit. And if you think you are, it's because you haven't been in that scenario. That's how I feel about faith and quack cures, though I don't personally engage in any of the above. I've never tried a quack cure for anything. Well, don't try it unless you absolutely have to. It should be a last resort. Do you regard acupuncture as a quack thing or legit? Enough people have told me it's legit.

The thing with that is, remember when the New York Times ran that piece years ago called The Placebo Effect is Real? I had heard other actually filled the prescription. I just looked at the prescription and knew that it could be there if I needed it and that was enough to not panic. Yeah, but the point of that title is a double meaning because obviously the placebo effect is real but it's also the placebo effect is real. In other words, if you're looking for a way to lessen your pain and the doctor gives you sugar pills and your pain is lessened. It's real.

Yeah, it's real. Because in the end, the point of the medicine was to lessen the pain. If you can do that by exploiting this weird thing in human psychology, then so much the better, right? Yeah. So that's how I feel about all that. So, one more question about. But I will say, like, being a parent and beginning to raise children that are, like, aware and

constantly asking why, you do sort of face a question, like, earlier on than you think of, like, where does God fit into the explanation of things? Or how does this come up? How do you answer that question? I'm like, I'm very, very into God. Like when talking to my daughter. And so, it's now, it's, I mean, not just in like the Jewish rituals, like we make a big, we have big Shabbat every week, and it's a very special thing, because she gets to sleep in our bed with us, and so it's like making that a special thing,

but saying the Shema before she goes to sleep and I don't know, the whole question of, as a parent you sort of, or at least for me, the question about like what is my sophisticated understanding of that, I don't know, but I'm like I do want to transmit all of this to her and I want her to feel like, I want to raise her in an environment where God is part of the conversation. Why? It feels like a really important, and it feels, I don't know, it's a good value system is like way too thin a way to say it.

But for example, like when we're walking around the street and we talk about like, you know, you do mitzvahs, like you do good deeds in the world, like let's look for mitzvah opportunities all the time and she'll see garbage. It's like, why do we do mitzvahs? It's like, because we want to help other people. And then your child will ask you, why do we want to help other people? Because it's good to help other people. Well, why, why, why? You will not believe how many whys you will get in the world, which is chachi bt is actually very helpful for some of these questions. But then in the end, it's like, well, why do we need to help people? Because people are, because we love all people. Why? Well, because we're all created in the image of God.

Like you do ultimately sort of like go back to that. And it's, it just, it comes up way more than I would ever expect. And so I'm curious when I hope. Yeah, I'm definitely going to ask. You'll have your own children. Like how you'll face that. That's a good question because on the one hand,

I don't, I really don't want to lie to my kids and tell them daddy believes in God. Even if mommy believes in God, which is probably going to be true in my particular case. At the same time, if they give me the never ending whys, and I'm on three hours of sleep, and I'm taking them to whatever practice or whatever, I don't know if I'm going to have the wherewithal to actually try my best to explain why you ought to be good in the world. So, I get why it would be useful to have God as a backstop and to say, well, you know, God says that you have to be kind to people and that has to be enough.

I don't know what I'm going to say. I'm going to try my best. It's going to depend on the kid, obviously, but I'm excited for it. If Nellie were here, she would tell you right now, like do it soon, don't wait, do it soon. Oh yeah? Yeah.

Yeah. Well, we'll see about that. So I'm curious, we were talking about kids, do you feel that having kids has changed you at all? Because I have seen examples where someone has a kid and it just unlocks an aspect of their personality that I didn't even know existed prior to them having kids. So I'm curious, do you feel different as a mom?

I think it's, I just think having kids changes everything. It's not that my personality changed, I think it just kids changes everything. It's not that my personality changed. I think it just intensifies everything, the highs and the lows. But now I feel like I have a deadline. Like, how am I going to make sure that the University of Austin is a great place to send her in 60? Like, everything is measured in a much more condensed way.

Like, when you're young, it's like, oh, I want to change the world, I want to do great things. And now I'm like, no, I'm on a deadline. And your deadline is when they leave the house? Sure, I mean, not literally, but you have a feeling of like, we're speaking on whatever day this is. And last night, two young people were gunned down outside of the Jewish museum in DC. And it used to be that I would read that news and feel angry and sad and everything that I still feel. But now I feel this sense of like, I cannot allow my children to grow up in a world where

that is the case. That's one way that it's manifested for me. I think the other thing is just you are not the center of your world anymore. And I find that to be like the most wonderful feeling in the entire world. Maybe for other people it's not, but recognizing like your birthday, it's like your birthday, who cares about your birthday? Like just all of these, all of the sense that like you're at the center of the world, it just like immediately goes away. And then just every, it's like every cliche is just so unbelievably true.

Yeah, I highly recommend it. So a few more questions about the free press. When the free press started, being against wokeness was higher value than it is today in the sense that it's, there was more wokeness to oppose, I think, at least in the news talking, you know, 2022-ish. And it was rarer to, it was harder to be opposed to it from a reputation based standpoint.

It was just harder to be the person with your face out there saying, you know, I'm against defund the police or, you know, I'm against children transitioning before a certain age or whatever it is. Now that's opened up a little bit. We're in a new era. It's opened up a lot. Yeah. So how do you think the Free press as an organization should meet the new era? By applying the same set of moral and journalistic values that we applied to excesses of the

liberalism of the left, now increasingly that are coming from the liberalism of the right. So I am not of the view, and I think Tyler Cowen disagrees with this, a lot of smart people do, that like wokeness has peaked. Like, I don't think that at all. I still think it's an extremely active thing. It's just been sort of, it's won so fully inside certain institutions that it's almost like not a headline anymore because they've just been fully transformed. So I still think that's an important story. But

the same set of impulses that led me and a lot of other people that now work here to want to write about the ways that people were being dehumanized or pitted against each other because of a version of identity politics that was small and narrow and pinched. Now we apply that to what's coming out of the right. The same set of values that led people here to want to question, let's just say the orthodoxy or the consensus around school lockdowns. Like that was a huge issue when the free press first began.

A lot of parents, especially, a lot of public school parents began reading us because of that issue. And they were like, I don't understand. Like, you know, I vaccinated my family, I've done all the right things, but kids can't get COVID. So why have they been home from school for two years? Like applying that skepticism now to other,

what Orwell called smelly little orthodoxies that are coming from different precincts in the culture. Like the values remain the same. The threats to those values are coming from different places. And we should be judged on whether or not we are able to see them clearly, meet the moment and apply the same standards and same rigor that I think we really successfully

applied to the stories and the storylines and the themes when we began to a new set of them. Some people have also criticized us because they're like, you missed X and Y and Z. And sometimes they're right. And I think sometimes my describe that to us having a blind spot in any number of ways. Often it's just a super practical question, which is like, hey, I didn't have anyone covering the law, like lawfare, and the law has been an enormous issue since Trump became elected. I'm not only the editor in chief and the host of a show,

I'm like having to go, I need to recruit those voices. Or pick your issue, there's just things that we were not equipped to cover because they weren't stories before. And so figuring out the people that can, that share and live out our values and the frankly like the independent cast of mind, like finding the people that both have the journalistic chops, the writing ability and the independent cast of mind, it is very,

very difficult from just a pure talent perspective to find those people. So, you know, I would be lying if I sat here and said, you know, a Kamala Harris presidency would have been a breeze for us to cover. Like we're built to cover that kind of thing. A Donald Trump presidency is a huge, huge pivot and shift for us, you know, like we know how to cover the woke left. What does it mean to cover a woke right?

We know how to cover, you know, anti-Semitism, well, from the left and the right, but especially that was coming out of the institutions of the left. What does it mean to cover it when it's coming from, I mean, literally neo-Nazis on the right. Like you're catching me in a conversation as I'm navigating us through that shift and finding the right voices and the right talent, many of whom are already here, by the way.

They just need to like, it's like a journalist that was covering the climate change beat and now putting them on, you know, crime. It's like you have to build up a new set of sources. You need to like learn to master your new domain. And that just takes a while. So I'm pretty proud actually of how we've navigated the change,

but we have a long ways to go. And again, kind of going back to where the conversation began, like we don't exist as a news organization just to like criticize the president, Trump or whoever else that will be. I think because other publications largely do that day in and day out, when people see us not doing that on every single topic, every single day,

it looks like we're somehow pulling our punches. And my feeling is just like there's lots of other stories out there in the world. The other part of it is that we're a business that differentiates ourselves. So in other words, we're never going to beat, at least in the current incarnation of the free press, maybe that will change, Maggie Haberman and Jonathan Swan at the New York Times for scoops coming out of Mar-a-Lago. They're going to get that every time. We're probably never going to beat Patrick McGee on covering Apple in China. He was just on the show and he was excellent. So where are the topics and what's our wedge?

What's our way into an issue? We talk about this in every editorial meeting. What makes this a free press story? What are the stories, not just the topics, Trump? Trump is a topic, lawfare is a topic. There are topics for every news publication out there. But what is the unique free press way into this story? What's the way that we can uniquely cover it? And there are certain moments where I'm like, that's it.

Like, you know, specifically I remember in the, when Zelinsky came to the Oval Office and there was the whole meltdown of the meeting, that Monday, we published Eli Lake kind of blasting Trump and JD Vance on the Saturday. And then by the Monday, you know, we needed to have a piece to satisfy the reader the next day.

And then by the Monday, we had commissioned five other pieces from really different angles on that story. And that kind of like kaleidoscopic view, I was like, we can't do that every day. It's very hard. We worked all weekend. But like the value in that for the reader,

I feel was tremendous. And at our best, that's what we're trying to deliver. Yeah, I mean, that's what attracts me as a reader to the free press, because I know I'm going to get that perspective on whatever the news of the day is. So you talked a bit about some of the fever swamps developing on the right, especially in the podcast world, thinking of Tucker Carlson, Daryl Davis, Smarter Made, some of the guests Joe Rogan has had,

Ian Carroll. Is it Darrell Davis or Darrell Cooper? Darrell Cooper, sorry. Yeah. Darrell Davis is a really awesome blues musician that deprogrammed KKK members. He's great. Darrell Cooper is programming people in the opposite direction. in the opposite direction.

We're talking about the mainstreaming of ideas that five, six years ago would have been so outlandish. I mean, the idea that Kanye could have a song called Heil Hitler. And that very, very prominent people would share it in the name of free speech, as if in the name of free speech you need to flaunt every single taboo. To me the crazy thing is not that you could get 30 background dancers and the other 50 people you need to make a professional grade music video to participate in a song called Heil Hitler.

And I wonder if you flip that situation, right? If you get a Jewish artist, a Jewish rapper, there aren't that many, but if you got a Jewish songwriter or something that wrote a song that was just as racist against black people as Heil Hitler is against Jews, could they even find 30 Jewish background dancers and a couple dozen people of any race to participate in that video? I don't think so.

If you did a song celebrating slavery, you literally couldn't find 40 competent people to put the music video out, right? And so to me, it's not about Kanye, it's about the idea that you could get any number of people to collaborate on such a project. I mean, that seems scary to me. And I think that's, I mean,

I haven't seen anyone take that angle on the, that's really what's significant about the music video, not Kanye. Well, and not just in the video. I just saw a few hours earlier, I've been online a lot today because of the shooting and wanting to see the reaction or the non-reaction as it were from some people

or the shock among others who I feel have created a permission structure for literal physical violence against Jews and supporters of Israel. But there were like 20 guys, I don't know if they're the same ones from the music video, that Kanye had go for whatever reason to P Diddy's like Hollywood star and sing the song, in broad daylight in Los Angeles today. And yeah, I mean, I consider myself someone that is pretty awake to the moment

and at my best maybe able to see a little bit ahead of the curve, but I am shocked at how far and fast this has gone and how normalized, it's how normalized just like open hatred has become. What role do you think Twitter now X has played? Because I've, many have observed, I've observed that over the past two years under Elon's stewardship, it's just gone from clearly biased against right-wing commentators to clearly promoting and boosting straight up bigotry. Not just against Jews. Yeah, I mean, I don't think there's anyone

that's on that platform could deny that that's been the experience. It's basically become, I still use it. It's still a really fast way to get in touch with people. Yeah, I still use it too, to be clear. Like, you know, last night I was looking for people. But I post a lot less. I post a lot less and it's very, very hard to find quick news in the way I used to be able to.

Look, I mean, one of the reasons we covered the Twitter file story was because it was an exciting story. But also if you asked me then, I would have said, this is exciting. I love the kinds of things that Elon and this new gang of people say that they want to do with it. I was so, so sick of all of social media platforms being biased clearly in one direction, shutting down totally sensible conversation. But wanting Jay Bhattacharya to be able to talk about the Great Barrington Declaration is not wanting to be served every single Alex Jones insanity. No, really, because there's this,

probably most people listening to this don't spend as much time on this platform as you and I do. If you click on the for you tab, which is like what Twitter is actively promoting, like it is wild what's going on there. It is some of like the worst, most just blatant bigotry that you can encounter on the internet. And they're serving it to you. away is really what Twitter is optimizing for. I mean, they say hilariously that they optimize for time well spent, which is like this phrase that social media moguls kind of have been saying for a decade. Because it really is at our best what all of us want from these platforms is we want to maximize time well spent. I don't want you to show me the thing that I can't look away from because it's so shocking, appalling, or sexual. I don't want you to show me that. I want you to show me something that my better self wants to see.

I want you to show me the person that I think about intentionally follow because I want to see more of their content. I don't want you to show me a thing that I just can't look away from, Yeah, I mean, I will just say it's like probably that one, not as heavy user as Elon, but like a very heavy user of Twitter. And I have found it to be an incredible, at its best, an incredible tool, journalistically. Yeah. And it allowed me to, you know, connect with smaller, like writers, with small platforms all over.

Like, it's incredible in that, you's incredible at its best. I just find myself being, not just shocked by what I see there, like actively disgusted and alarmed because it's really hard when you're on there to understand, like, is this just like where culture is now or is this just a narrow, narrow, narrow right-wing echo chamber and hoping it's the latter but not being quite sure? Yeah.

Do you trust Trump to combat anti-Semitism in a way that you think is net beneficial? It's a great question. I think it's very hard to bet on Trump when it comes to anything because the whole thing about Trump is, we have a great piece by Yuval Levin about this today, it's just the whiplash. It's like there's tariffs, there's no tariffs. You're hired, you're fired. Like I hate Zelensky, no, maybe he's not so bad. Like with, I would just never make a bet on Trump in any direction. I think it would be absolutely foolish to do that.

On the other hand, you know, when something like last night happens, I feel comforted genuinely to look at the various messages coming out of this administration that are absolutely morally clear and not trying to bring in also Islamophobia to a thing that was clearly targeted at Jews and be extremely forthright in their condemnation of it and then frankly connecting it to a broader culture where normalization of hatred of Jews and hatred of supporters of Israel has been, like, it's just been completely normalized since October 7th in this country, especially on the left.

It doesn't mean that there's not crazy right-wing anti-Semitism. Like I'm very, very scared of that too. And that has a huge impact on my, like my actual life. I mean, they both do. care to that too. And that has a huge impact on my, like my actual life. I mean, they both do. So, you know, if we end, if we have this conversation, however many, three and a half years from now, and there's been Abraham Accords with Saudi Arabia,

and maybe some of the other Gulf States, and the universities have become more serious in, I don't want to say fighting anti-Semitism, but just applying the rules that they claim to stand for to Jews as well as other minority groups. Like you could never, and going back to your Kanye rap analogy, like you could never imagine in a thousand years a group of any students gathering in the middle of campus, screaming the N-word or holding up Confederate flags and like, just being given that a pass. Right, holding up signs that said go back to Mexico

or something. That would just literally never happen. So, I mean, if we're sitting here three and a half years from now and those things have happened, well, I praise Trump for it in the same way that I praise him for, you know, the Abraham Accords and the first administration and moving the embassy to Jerusalem.

Definitely. Like, I just think you have to be intellectually honest and I've been very clear in the way I think about Trump, you know, the fact that I truly do believe that character is destiny, it's like an old fashioned idea, I still believe that, but that doesn't mean that he can't do good things. And there were good things that happened

in the first Trump administration with regard to Israel and with regard to Jews and antisemitism. Could that happen again now? Yes. When I see the president accepting a Qatari plane, does that make me extraordinarily concerned? Yes, it does, you know. So I don't have like a clean and crisp answer for you. Because I think anyone that tries to say that Trump does, stands by his word and

does the first thing he says, has not been paying attention to who Donald Trump is. Yeah. How do you feel, if at all, you reconcile your proud Jewish identity with your general opposition to identity politics? Hmm. I think that there's like a really enormous misunderstanding about what identity politics is, or at least

what I mean when I use that phrase, I don't mean that people shouldn't be proud of like any part of who they are. I don't think it's strange for someone to be like, I'm proud to be gay. Like great, good. I'm proud to be Jewish. Great. I'm proud to be black. I'm proud to be gay, like great, good. I'm proud to be Jewish, great. I'm proud to be black. I'm proud to be born an immigrant. I don't think there's any danger in any of those things. Where I have an issue and I think anyone with eyes to see over the past 10 years has been

able to see this is a version of that that says, I am better than you because of this part of my identity, or I am born in a position of either, you are born in a position of original sin or original standing because of some part of your identity. Jonathan Haidt has spoken and written much more brilliantly about this, and I'm going to butcher it, but I'm going to try, which is like, there's a capacious version of identity politics that says, come along with me and let me tell you what my experience has been in the world. Because I believe that despite the fact that you have more melanin or less melanin than me, or you have a penis and I have a vagina, that doesn't matter. Like come along with me as I tell you about my experience. That's like a positive version of what identity politics can look like. The version of it that we've been living with,

and I don't see any sign that this is going away, is a version that says, you can never understand me. You can never step foot in my shoes. And in fact, we're in some kind of like zero sum game with each other, where we're like pitted against each other necessarily because of these immutable characteristics or because of the lane of our birth. And in fact, you can never understand me, you're constrained to the lane of your birth forever.

That's what I have a problem with. And so for me, being an American, being a Jew, supporting Israel, being gay, like, I don't see any of that as being in conflict with each other, nor do I see that as precluding my ability to connect with other people. I think if I believed in a vision of that, where I was saying, like being a Jew makes me a victim and therefore makes you unable to understand me, like, yeah, then you should have an issue with me. Or being a Jew makes me better in some way than any other person.

Yeah, then you should have a problem with me. I think that that's like the test. Does someone's identification with a group or with a set of ideas, like can that, can their identity allow a broadening or does it mean a narrowing? And if it means a narrowing in either from a perspective of chauvinism or, you know, victimhood Olympics,

that's the thing I think that I have, that's the thing that I do have a problem with. And that I think is like fundamentally dangerous in a country that, you know, is more than 300 million people from wildly different identity groups that are trying to be one larger identity. But we don't ask, we don't ask people when they become American, like, you know, give up your

Italian day parade, give up your Columbus day know, give up your Italian Day parade, give up your Columbus Day parade, give up your Israel Day parade. It's like, that's the unbelievable miracle and beauty of this country is like we're able to kind of hold both. I think the question that a lot of us are asking ourselves is whether or not that can last. Right. One I've gotten online recently is, how do I reconcile supporting Israel

with being against identity politics, as if supporting a country that was based around protecting a particular group of people is the same as supporting identity politics in general, of the kind you just described, which I agree with your distinction. To me, this is ridiculous. As our mutual friend Noam Dorman put it to me recently,

when neocons and actually many people around the world were lamenting the plight of the Kurds in Iraq and Syria and kind of wishing that there was a Kurdistan, not only to protect them from Iraq but also from Turkey and so forth, no one in their right mind would say, oh, well, that's, you're playing identity politics. We'll say, well, no, there's a group here that the region has proved they cannot keep this group safe and in fact are so hostile to the group that it makes perfect sense from the point of view of wanting there to be peace on earth really

to give this group a state, right? To give this group state power. I mean, it just, to me that's such a nonsensical argument. I think it's being used just very cynically. Well, yeah, exactly. Like no one would say, you have pride in America. Like you're an American patriot, identity politics, like you're an Italian American that cheers for some Italian soccer team,

identity politics. It's like they are misusing, in my view, I think people are kind of cynically misusing that in the same way they are cynically misusing cancel culture, which was always meant to describe a cultural movement that was trying to shut down legitimate debate. Now they're saying, no, no, hold on. Thinking that Kanye's Heil Hitler song is bad, or suggesting that sharing it is maybe irresponsible, that's cancel culture. It's like, come on.

There's a lot of that going on right now. How do you think the climate has changed for just an average Jewish person in America post October 7th and the reaction to October 7th? We could have a whole hour on this. I, it's hard. If you are Jewish in America, you are already used to a reality that would be shocking to people that don't know Jews or don't go into Jewish spaces. There's armed guards at all of our schools, at all of our synagogues. There's just a level of

at all of our synagogues. There's just a level of like hardness and security that I think would be very shocking to most people and that got even more intense after October 7th and October 8th. This is the more like emotional and existential part of it, is like I grew up so fully believing that anti-Semitism was a vestige of other times and places and could never become normalized in America. Like I just, that was like an article of faith in the family that I grew up in. And so even though anti-Semitic things happened and most obviously and tragically in the massacre at Tree of Life, when kids said to me, like, pick up pennies, wear your horns. Like, I remember the Catholic school bus would drive by and scream, kike and dirty Jew up my sister.

Like, the attitude of my parents was not at all like, we have to protect you from the anti-Semitism of the country and the community you're in. It was how sad for those people that they don't know what country and culture that we're living in. Like how embarrassing for them. And that just gave me such a supreme level of confidence that like we're not like Europe, we're not like other places that my ancestors have fled. And I think one of the most tragic and profound adjustments

that me and like every other Jew I know is living through right now is questioning whether or not that's still true. And whether or not the things that have made America the most exceptional diaspora experience for Jews will hold for our children. And that is like the story for me of this moment. And so much of the work that I'm trying to do with my own writing, and then just more generally with the free press, you know, it's not about like fighting for Jews to protect Jews. Of course that's true.

Like of course I want my family to be safe. It is a profound under, like I don't know that much about many things, but I do know that if you study history, societies where this kind of hatred is allowed to become normalized are societies that are dying or dead. And so the stakes of it are not just, it's not just about my safety or the safety of my family or my community. It's about the safety and flourishing of the country itself. And I just, I try and say that in so many different ways on my most despairing mornings. I'm like, is it like, will that message ever get through? Like, is it possible to explain to people how an attack on Jews for being Jews at a museum in Washington, D.C. is actually an attack on everything

that this country stands for? You know, at my best, like, and my most hopeful, I really believe that most Americans still understand that to be the case. But that's the case. If it's not fuck yes, it's no. I might just be a fuck yes or no person. Maybe not after one date, but I really believe in trusting your gut. I'm sort of astonished by how many people will pursue a relationship because it's good on paper.

It's like you're not dating the paper. Like, it's got to be fuck yes. It's the biggest and most important decision of your life. Guilty pleasure. Oh my God. Alcohol and food. Same as mine. But alcohol, for sure. Yeah. And finally, one thing you're looking forward to.

Oh my God. I'm going to Israel this summer with Nelly for the first time. And finally, one thing you're looking forward to. Oh my God. I'm going to Israel this summer with Nelly for the first time. I'm hoping that like HOOTIES will allow that to happen. We haven't taken a vacation pretty much since we started the company, so I'm really excited about that. And I know it's a cheesy answer, but I'm going to do it anyway. I'm not someone that I, I never thought that I was an entrepreneur. I still don't know what like, CACs and COGs and like all of these things, like I don't know what any of that stuff is. But I feel really proud of what the free press is.

I feel so proud in the kinds of people that want to be a part of what we're doing here. And as exhausted as I am most of the time, and I'm telling you that there's a reason want to be a part of what we're doing here. And as exhausted as I am most of the time, and I'm telling you that there's a reason that startups are like the game of 21-year-old men and not the purview of middle-aged mothers with nine months old at home. But I feel very, very excited about continuing to build this and just inspired and energized and like eager to get up the next day and to get to work.