Mixed Signals: ‘Substack isn’t cool,’ gatekeepers are, and other strong opinions from tastemaker Chris Black

Max Tani:
Welcome to Mixed Signals from Semafor Media where we are tracking the wild changes in this media age. I’m Max Tani, media editor at Semafor, and with me as always is our editor-in-chief, Ben Smith.

Ben Smith:
Hey, Max.

Max Tani:
This week on the show we’re talking to Chris Black. Chris is the co-host one-half of the popular podcast, How Long Gone, an advisor to fashion brands like J.Crew, Thom Browne, and Stüssy, among others.
We’ll ask Chris about building a hit podcast from scratch, the surprising value of cultural gatekeepers in 2025 being starstruck by Smith’s guitarist, Johnny Marr, and what the TV version of How Long Gone could look like.

Ben Smith:
This is an exciting day for you, Max, isn’t it?

Max Tani:
I’m a little excited about this one, I got to say, but we’ll dig into all those questions with Chris right after the break.

Ben Smith:
So, Max, we talked to a lot of people on this show who sit in some way or other at the intersection of new media and old who are navigating these changes. Chris Black comes out of fashion, out of marketing and advertising and has become a pretty big media figure in his own right. I have always found him a little hard to figure out like, “Who is this guy?” Can you explain?

Max Tani:
Yeah. I think he’s hard to figure out because he does a lot. He’s everywhere. If you pay attention to men’s fashion and lifestyle journalism, commentary and increasingly is involved in the celebrity media circuit as the co-host of the podcast, How Long Gone, which is a three times a week interview show that he co-hosts with Jason Stewart, who’s a pretty well-known LA DJ.
But Chris got his start as a manager of the pop-punk band, Cartel and worked his way backwards into fashion as an advisor to a lot of big brands and just as a general tastemaker and a writer. He’s an author of a book about taste. He writes a weekly column for GQ about men’s fashion, music, television, entertainment, and also writes semi-regularly for New York Magazine’s The Strategist recommending clothes and products to people, and he’s been doing that for a really long time.
And since the pandemic, he’s become more well-known as the co-host of How Long Gone which has really exploded and become a must-stop for a certain kind of entertainment figure. They get a lot of really big musical guests. They’ve had Charli XCX on, and they’ve also had on a lot of popular people from the food world and increasing number of actors. They’ve clearly moved up the ladder on the list of people who celebrity PR people are pitching.

Ben Smith:
Although the celebrities then sometimes wind up being totally confused about what environment they’re in, which we can ask Chris about. I do think the thing you said, he’s a tastemaker, and it’s funny. I thought we were all just supposed to get our taste from TikTok. And so there’s something interesting about whether he’s coming or going in that respect.

Max Tani:
Well, Chris is actually waiting for us. So why don’t we bring him in now?
Chris, thank you so much for coming on the pod. So How Long Gone, the show, reminds me of stuff that I grew up listening to, whether it’s drive-time radio or late night TV and the dynamic that you guys have. I feel like in some ways podcasts like How Long Gone have replaced Late Night. If you think about it, it’s funny news of the day plus a humanizing interview with somebody who’s famous or a cultural figure who’s interesting to you guys. Do you see it that way? Do you see it having that DNA?

Chris Black:
Yeah, for sure. That’s just partly our age. You know what I mean? Jason grew up in LA. I’m sure he was listening to Kevin and Bean, and I grew up-

Max Tani:
That’s right, KROQ.

Chris Black:
I grew up in Atlanta listening to 99X who was Leslie and Jimmy in the morning. It’s like, yeah, of course.

Ben Smith:
Yeah. So you think of it as radio rather than Late Night?

Chris Black:
Late night to me has the band-playing element. That’s what I always most drawn to about a lot of those shows, is I know it’s not Conan, and I know it’s not David Letterman booking the bands and the artists, but there were time periods where that stuff was really good, and I watch it all the time on YouTube.
I was never a super big Late Night guy. I’m a big Saturday Night Live person, but I was a very, very big radio person. And I think Jason would say the same.

Max Tani:
You have an interesting setup where you’re signed to Jagjaguwar or they have some deal with you, guys.

Chris Black:
We’ve got all kinds of shift going on. We had a canned coffee that we made years ago, and it was with a producer in Indianapolis. So we went to Indianapolis. We met Eric. I was like, “I would love to do this funny idea where we listened to the music from the label,. So you guys own it. So it’s super easy.” And then we just talk about it. We put it on a double CD, and it’s funny for everybody and fun for everyone. And they were just like, “Yeah. Let’s rock. Let’s do it.”

Ben Smith:
It’s funny, the canned coffee thing, because I remember when we were introduced, I asked somebody, “Who is he? What does he do for a living?” And it was inexplicable. What were you telling people before you were I’m a famous podcaster.

Chris Black:
I don’t lead with podcasting to this day if I could help it.

Ben Smith:
So what do you do for a living, Chris?

Max Tani:
Why? Is it shameful?

Chris Black:
No. It’s a joke, but I think it’s different, honestly. We started this during COVID. It’s changed that much where everybody knows what this is now, not how long podcasting as an industry. You know what I mean? Thanks to call her daddy and Joe Rogan and SmartLess everybody knows.
I would say I was a consultant. I’ve had my own business for, at this point, Jesus, 18 years. I started in the music business. I was a manager, had some success with that and then moved to New York and just fell backwards into working with Vice and New Balance.
And then as we get along it’s like Thom Browne, Stussy, J.Crew. I just think that I’m an outside person who can come in and I wouldn’t say make a decision, but I think have a clear point of view and be like, “That’s good. That’s bad.”
And I think when you’re in-house somewhere, the politics of how things work internally prevent people sometimes from being as honest as they should be, and I think that’s something I’ve greatly benefited from. And also, I started doing this before everyone now doesn’t want a job. Everyone thinks they can get on TikTok and be a millionaire. Everyone thinks they should be a consultant so they can go travel the world all the time and work from their laptop. I tell people all the time, it’s like, “Yeah, it’s cool, it’s fun, but you have to have the stomach for everything to disappear.” And I think most people don’t have that and that’s like this weird bottom line factor for me.

Max Tani:
So is part of that job is like I’m better at having difficult conversations with brands or fashion labels, or whatever.

Chris Black:
I don’t think it’s even difficult. I think it’s more just decisive because what happens in these situations, I’m sure you guys experienced this in your careers, people just talk in fucking circles. People just talk and talk and talk. And it’s like, “That’s fine.” And I understand that there’s some of that that’s necessary to get to the end goal.
But for me, it’s about making a decision and then working on it. It’s a very clear path. I also have found a niche where I’m able to... I like a lot of creative people, like true, true creative people have to be brought back down to earth a little bit for things to monetize so that we can all continue to do this for a living.
There’s a level where it has to come down a little bit for the masses to understand it and for it to work on a financial level to keep everything going. And that’s something that I think I learned to really understand, appreciate and support the creativity, but also understand there’s a bottom line, and we got to remember that that keeps us all here.

Ben Smith:
Yeah. Yeah. I think one of the reasons that we’re excited to talk to you is because you think a lot, I think about taste and about tastemaking and that’s something... We’re in this funny moment, I think, where the internet has obviously for decades now really democratized these questions that used to be decided as Conde Nast headquarters, and people take more cues from influencers, random people on TikTok than from the official arbiters of taste. I’m curious how that process, which basically is in some sense your whole career has changed how you think about what’s cool and interesting. And how many advice you give clients?

Chris Black:
I think the more saturated it gets, the easier it is in some ways. I think there’s just too much. I, famously to the detriment of my bank account, respect the institutions quite a lot. I do a weekly column at GQ, and I could go do that on Substack and make a lot of money, but I don’t think Substack is cool. I think it serves a purpose. I subscribe to a lot of them.

Ben Smith:
Are institutions cool again or is it that they never stop being cool?

Chris Black:
Institutions never stop being cool. I think we’re seeing this a little bit with the Graydon Carter memoir and this new Conde Nast book that’s come. People are like, “This shit is cool.” Obviously, it’s changed. You know what I mean? You don’t have a car service and a $400,000 a year contract for four stories, but it’s still, there’s just some glamour attached to it where I think there’s no glamour attached to a lot of this shit that’s happening online.
That’s similar with How Long Gone. We don’t want to be beholden to the listener. I don’t want Patreon to own me. We’re very consistent, but we put that podcast out three times a week because we want to, and we have advertisers that want to get in bed with us and our ads sell out, and that’s our business, and we’re working on TV and video, all this other stuff. But the reality is that, again, we could make a lot more money if we were doing a paywall of some kind. But for whatever reason, it doesn’t speak to me.

Ben Smith:
It’s funny, we had a CMO on the show last season who was saying that she really sees her job as being totally dialed into TikTok. And then when something goes viral on TikTok being the first brand to get in that creator’s ear and associate with them. And I think that is a big culture right now in the ad business.

Chris Black:
Totally.

Ben Smith:
Do you think that’s totally misguided?

Chris Black:
I think it depends on the brand. That’s the thing. If that’s the game you’re in, then it can probably work. But I think the issue that arises, a lot of people that aren’t in that game think they need to be, and I’ve had meetings about TikTok strategy.
I’m like, “Why are you talking to me?” I’m 42 years old. I don’t use TikTok. Let’s bring in the 23-year olds that work at this company and talk to them about it. That’s where the information is. There’s a certain age threshold for stuff like that where it’s like you have to entrust it into the younger generation because that is their thing. That’s what they’ve given us, and I think that is where some of the mistakes happen.

Max Tani:
I think it’s interesting that you guys have decided or you’ve decided not to do the Substack thing and left some money on the table by doing stuff for New York Magazine and GQ. But in some ways, it makes sense. If you look at a lot of Substacks, they look exactly the same. The quality is definitely shittier in many ways. There’s some amazingly talented writers, but there’s a lot of poor editing. It doesn’t look great. It’s like utility, but it’s not tasteful. It’s not stylish.

Chris Black:
I think that’s the thing. We’re reengineering the magazine at this point. One of the more popular fashion newsletters is called [inaudible 00:12:01], and it’s shopping. It’s really about shopping, and it’s really heavy links. It’s really great information if you care about clothes. She hired a menswear writer. She hired a design writer. It’s like, “Oh, that’s just a magazine.” And that’s great. I just don’t know if there’s a single voice that I want to hear from that much.

Ben Smith:
Yeah. Is it just you? I think the whole culture is getting a little tired of this. This moment is maybe coming to an end of this total fragmentation.

Chris Black:
I just think if you have an audience, they’re going to listen to you, but how do you grow it beyond that? You know what I mean? How do you really grow basically talking about yourself? It’s hard. It’s really hard, especially if there’s no sense of humor or no self-awareness.

Ben Smith:
Yeah.

Chris Black:
This is what happened with music too. There’s just too much of it because they made it too easy.

Ben Smith:
Yeah. How do we fix that? How do we make it harder?

Chris Black:
Gatekeeping is something that I just respect. I think there are people that know more than me and I want them to help inform what I’m seeing and listening to and hearing. I don’t understand why that’s become a negative really.

Max Tani:
I also think that having people who are editing your stuff at New York Magazine or at GQ or these places are actually bringing another perspective or point of view that sometimes you lose when you’re a Substack writer blogging on your own. You could be amazing at it, but you only have so many good ideas in a day.

Chris Black:
No. I talk to my editors at GQ, Nick Catucci and Alex Pappademas. I talk to them all the time, and they let me do whatever I want, but if I am running low, if the tank is on E, they’re like, “How about this?” And I’m like, “Sick. Perfect,” because we’ve worked together long enough where they know what will trigger my brain and get me to operate the way that they want me to, and that’s what that relationship is about. They make you better.
And I think that it’s a necessary expenditure if you’re doing your own thing. You hire an editor that’s going to make everything better, even if it costs upfront.

Ben Smith:
Yeah. A lot of our listeners who are in the gatekeeping at editing businesses are going to be very happy to hear this.

Chris Black:
The gatekeeping business.

Max Tani:
That is true. We over index with gatekeepers. I’ll say that.

Chris Black:
No. I think that it’s just there’s a level of professionalism that you guys brings to the table with what you do with what airmail does with [inaudible 00:14:24]. There’s a level of professionalism and design and thought to it that makes it just inherently more interesting to me personally.

Ben Smith:
It’s funny that you mentioned those new outlets. Do you feel like the old ones have abandoned that a little bit, that they’ve democratized places like the New York Times, the TV networks have almost democratized too much.

Chris Black:
To some extent, and as someone who’s personally benefited from this, a style section piece about a newsletter happens once a week. It’s really there. But then I like to remind myself that all of the newspapers, they’re talking to an audience that maybe isn’t quite as hyper online as the three of us.
So I understand I’m not going to lampoon them for being quote, unquote, “late,” because they’re reporting to my parents. I was home over the weekend, and my dad is a lifelong Wall Street Journal subscriber, and he was like, “Have you heard of this New York fashion brand called Callie Mayer?” And I was like, “How the fuck do you know about this?” He’s like, “I just read this great story about...” And that is the purpose of the newspaper. The newspaper, I think we look at it differently because we’re just ingesting information so much and so rapidly. I think that’s the difference.

Max Tani:
This is actually how Ben talked me out almost taking a job at another publication that offered me this exact job explaining Substacks to older people.

Chris Black:
And I think that is a real service that’s provided. Honestly, that’s what you’re paying for. I subscribe to the New York Times and the Financial Times, and it’s like the Financial Times to me and how to spend it is arguably the best publication out as far as that goes. And what she’s been able to do with that is just really impressive.

Max Tani:
Totally.

Ben Smith:
Yeah, it’s extraordinary.

Chris Black:
I feel like that’s a product that has to come from Europe.

Ben Smith:
Yeah, well, when I was at BuzzFeed for eight years and I did leave thinking, “Wow, we’ve really managed to pull our mainstream competitors down market to compete with us,” and not just us, but the whole social media era pulled the New York Times, the Washington Post, the Wall Street Journal into this competition with social media and left a lot of space above it, which honestly is where the FT stayed and certainly is where Semafor saw ourselves is going.

Chris Black:
No, I know exactly. I think you’re completely right. I think it’s just once everything became a race for clicks, it’s like no one is immune to that. The bottom line is just too strong.

Max Tani:
So getting back to some of the work that you’re doing, you’ve mentioned you’ve done a lot of consulting advising for places like J.Crew, Thom Browne. You mentioned Stussy. Who’s really impressing you recently, and what’s been interesting to you?

Chris Black:
The brand is called Carter Young.

Max Tani:
Oh yeah.

Chris Black:
He’s a guy from Detroit who went to NYU, and we met when he was not fully getting started, but a while back. And I wrote about him for airmail actually when we first met because this is so great, and he’s really hit a stride, and I think it’s really, really going to work.

Ben Smith:
Just explain this to me like I’m a golden shepherd. What is this?

Chris Black:
It’s basically just great American clothes that are interesting and feel fresh, but it’s ideas like silhouettes that you recognize. You know what I mean?

Ben Smith:
Yeah.

Chris Black:
So it’s like I have a plaid cowboy style shirt basically with the three buttons here, but it’s gauzy. It’s almost see-through, like these modern twists on. I think he’s doing such a great job. The photography looks great. The price point is really good. It’s a real business. I think a lot of fashion especially when you go to a runway show, it’s just kind like, “What is this?”
That’s always my, I’m like, “What is this? What’s the point?” And you have to remember, and Thom Browne taught me this, it’s like a performance. You think of it more as theater than you do commerce. And I think that that’s why a lot of the stuff you’ve see in runway is never for sale, and that’s not the point. It’s to show what the brand is and what it stands for, and what it aspires to be. But brand-wise, Auralee, Apres, there’s all this stuff coming from Japan. There’s a new store in Fort Greene called Ven. Space that a guy Chris Greene opened that it’s like-

Max Tani:
That place is amazing. No website. Just, literally, you have to go there.

Chris Black:
I was in a meeting yesterday with some guys, and we were talking about how I think retail is important again. I think we’re all fatigued of getting every single thing online, every single thing in a package. And I remember the first time I made a little bit of money and went to Neiman Marcus at Lenox Square and spent $800 on a pair of shoes or whatever. I felt like a fucking king. They’re bringing you champagne. Post-COVID, it’s a little different. If you walk into a Prada store... I was in Singapore and all there is to do there is go to the mall obviously.
So I went into all these designer stores. And now, it’s like they assign someone to you and follow you around like you’re going to steal. It’s not the experience it used to be. Hopefully, we’ll get back to that because I think it’s valuable. I think it’s an experience thing.

Ben Smith:
Yeah. I think your impulse, and I think everybody’s impulse right now is to look to these small downtown things. Are there any big American brands, big advertisers who you feel have figured this out or is it hard to be big in this ,ind of fenvironment?

Chris Black:
I think it’s hard to be big and move the needle. I think it’s easy to be big as far as selling stuff. Yeah, Ralph Lauren recreating Polo Bar for one day for the show in the Hamptons is like, “That’s cool. That’s not inventing something new. But that’s a big swing and it’s cool. And it’s interesting.” I think what we’ve done at J.Crew, especially I work on the men’s side, I think we’ve been able to... When we shot Patrick Radden Keefe-

Ben Smith:
This is the great non-fiction writer, Patrick Radden.

Chris Black:
Yeah. Exactly, exactly. And that was really well received because it’s nice to highlight people who are good at something. It’s nice to highlight people that are part of the conversation, that are part of culture, that are doing something that is agreed upon as being interesting and important.

Ben Smith:
Not enough journalists model. I think that’s-

Chris Black:
No. That’s why there was a New York Times story about it because it literally was like, “This is wild. Why did you do this?” And he was like, “Well, why would I not do it?” It’s fun. It’s an interesting thing to do. I think that John Lobb, which is a old school British shoemaker, their print advertising is amazing, way better than it needs to be, but you only see it in fantastic manner how to spend it. They put it in the right places. They put it in the right places.
And I think that the bigger the brand.... My wife works at Calvin Klein. I walk by that billboard every day. That shit works. You know what I’m saying? That shit works.

Ben Smith:
No, for sure.

Chris Black:
The classic put Jeremy Allen White or Bad Bunny in their underwear, that’s going work.

Ben Smith:
That’s a relief.

Chris Black:
If you’re a brand like that, why would you ever change? That’s what works. You’ve been doing it for 30 years.

Ben Smith:
And maybe COVID era belief in the industry, which maybe Nike embodied most of all that actually forget all this stuff. We’re just going to have these direct, mostly email relationships, consumers do away with all this brand stuff, just be in this tight loop where we’re sending you shoes in the mail every three weeks. What do you make of that, that direct-to-consumer stuff?

Chris Black:
That’s very real, and I think that that’s a customer attention game as well. You get people really locked in. I think for me, it’s hard to imagine. Everybody I know is buying what they want because they want it. There’s not a convenience factor. Sure. There’s a price factor, but I just think there’s a certain shopping that happens based solely on utility,
And I think that’s what that approach was. And I think during certain times in America, that will work, but I think that in reality, advertising almost no matter what it is, should be aspirational. Even if it’s an email, if it’s an Instagram post, if it’s a tweet, whatever it is, it should feel aspirational in some way, and that’s what will always keep people locked in.

Max Tani:
Yeah. And the Nike thing famously didn’t work. Ben, you’re obsessed with this that it actually worked. It’s fucking terrible.

Ben Smith:
Yeah, it was one of the great catastrophes of modern marketing. And now, they’re back to trying to figure out a story.

Chris Black:
Nike’s my favorite. If you’re our general age, you grew up in the absolute golden era of Nike, of Jordan, and all that stuff. And to me, it’s like that is the brand. That is it. And to watch them falter and try to... They have to figure it out. It’s Nike, but they got their lunch ate for years, whether it’s Adidas or on running or whatever, they got killed. And I think that that’s just proof that no one’s safe. No one is safe.

Max Tani:
Well, we’re going to talk a little bit more about How Long Gone right after this quick break. To get back to How Long Gone, you’ve been in a lot of rooms with famous people and you guys have a pretty wide variety of people who come on the show. It’s hilarious to see you have somebody like This Is Lorelei or something like that, which is still a pretty niche.
I don’t know if you even call them indie artists anymore, but what we used to call an indie artist, and then you’ll have Andy Cohen on the show.

Ben Smith:
Jake Tapper.

Max Tani:
Jake Tapper, right. A friend of How Long Gone and also of Semafor, Nate Friedman, I was with him at the UTA party a few weeks ago in DC, and he went up to Jake Tapper and he said, “Oh, I loved your appearance on How Long Gone.” And Jake Tapper was like, “You’re literally the only person to tell me that,” which is incredible.

Ben Smith:
I told him that.

Max Tani:
You him that. Exactly.

Chris Black:
Thank you, Ben. That’s what Jason and I are interested. We have a lot of interest. I think most people do. You know what I mean? I think most people are interested in a lot of things.

Max Tani:
Has there anybody who’s been on the show who’s been actually intimidating you? Is there anybody who you’ve been nervous for having on as a guest?

Chris Black:
Yes, but not like Johnny Marr because he’s been in the fucking Smiths, and they’re like the greatest band of all time. I’m like, “This is pretty wild.”

Max Tani:
That’s right.

Chris Black:
You know what I mean? And that’s an example of one that probably took a year and a half to get it actually on the calendar from when the first email comes and then you keep going. But it’s usually more something like that or Cat Power or something that I’ve just spent so much time with personally and love so much that feels a little more heavy than someone who’s just straight up like I’m popular.

Ben Smith:
That’s how Max feels about this episode.

Chris Black:
That’s true. That’s true.

Ben Smith:
Is there anybody who surprised you or impressed you most that you’ve had on?

Chris Black:
Honestly, someone like Nancy Silverton, for example.

Max Tani:
Nancy Silverton, the very, very famous American chef.

Chris Black:
When someone who’s a little older and has nothing to lose and doesn’t really understand or care what they’re doing with us, that is the dream How Long Gone scenario where it’s like, “I don’t know what you guys are talking about. I don’t know why I’m here.”
With a lot of instances in our past, there’s somebody that works for this person that’s like, “You got to do this. You got to do this. You got to do this.” And they end up giving in, and then we benefit from that because them having no idea who we are or what we’re talking about is the perfect situation.

Max Tani:
You guys had on the lead singer of Broken Social Scene maybe a year ago, and I thought that that was a really fun episode because he clearly falls into that camp of somebody told him to go on the show.

Chris Black:
Yeah. Totally. Yeah.

Max Tani:
He listened to one of them, but he brought in a level of earnestness that isn’t always there. It was actually a very sweet-

Chris Black:
Agreed.

Max Tani:
It was a very sweet episode. It brought out something different, and it was clearly unexpected. It was fun.

Chris Black:
The earnestness thing is something that I’m publicly allergic to, but privately a big part of my life. I think for a show like ours, to have emotional diversity of any kind is really important. And we’re obviously just trying to laugh and entertain, and that’s the point. But if things take a turn, I think we’re able to go there. I think we’re able to go there and not be afraid of it and get in the mud with someone about whatever the subject may be.

Max Tani:
Yeah. And guys, I mentioned that you guys had on Andy Cohen. It was really, really, really fun. You could tell during that episode that he walked into it a little bit timid, maybe tentatively didn’t quite get you guys’ vibe, but then maybe slightly confused.

Chris Black:
Yeah.

Max Tani:
But then I feel like over the course of the episode, he really started to cook a little bit. He started to understand-

Chris Black:
Totally.

Max Tani:
... what you guys’ whole the vibe, the dynamic.

Chris Black:
I see it physically happen. I see the first 10 minutes or 15 minutes being like, “What the fuck?” Graydon Carter was literally, “What the fuck?” And then 15, 20 minutes in, it’s like, “All right. I get what these guys are doing. I’ll play ball. I’ll lower myself to their level because I know that’s what the audience wants to some extent.” They want to hear that, and I think that that’s always our goal, is to get a side of someone that you’re not going to get from a major interview or a major profile.

Ben Smith:
It’s been a very political. You launched into a very intensely political moment, and it feels like you guys maybe deliberately avoid talking politics on the show. And I’m curious how you think about that. Is it not your interest or are you trying not to alienate some subset of listeners?

Chris Black:
It’s just not our interest. I’m interested from a point of view of being informed because I’m a responsible adult, and I want to know what’s going on. And to me, it’s very clear the difference between right and wrong, but I don’t need to do an hour long podcast where someone’s talking about the evil Cheeto man.
We all know this guy is bad. I just don’t think it’s that interesting to be honest, because it’s not like Jason and I are going to be able to dissect policy. It’s just like this person’s stupid. It just doesn’t seem like we would offer much is the reality.

Ben Smith:
The obvious place for you to grow and for anybody in podcasting to grow and you see this happening is becoming television.

Chris Black:
Sure.

Ben Smith:
If you just look at the big podcasts, a lot of them are just actually Piers Morgan and Megyn Kelly, and huge television broadcasters who are basically making television.

Chris Black:
For sure.

Ben Smith:
I came out of blogging world. And at some point, blogging was this cute old-fashioned thing, but really we’re all just journalists on the internet. And I do feel like am I going to wake up one morning and see you guys hosting the NBC morning show or something? Does this eventually essentially become television, what you’re doing?

Chris Black:
I would hope so, Ben. I would really hope so. No. I think that that’s our ambition because, at a certain point, there are limits to the medium. And I think we could do How Long Gone in this version forever. It’s like we love doing it. The schedule is very clear. We’ll never run out of people to talk to, and I’m just the kind of person who needs to know what’s next. And I think that there is some of that. I think we’ve been resistant to video partly because it’s like a shitty set with two cameras isn’t super captivating, and I think Jason and I are both... We have a level of taste that we want to put on everything we do, whether it’s posters for our shows, whether it’s our work for... Everything, it needs to feel like us. And I think putting two cameras up in a garage Theo Von style is not going to work for us.
And so we’ve resisted, but I think that the goal is to do something with a little... We’ve been working on it for two years at this point, but something like what we talked about at the beginning, Max, like, yeah, it’s like a weekend update meets Letterman model where it’s like we’re talking about current events. We’re hanging out with celebrity, doing an activity, and then a band is playing because he music is just such a huge part of How Long Gone and Jason and I’s lives.

Max Tani:
Looking at your guests and thinking about the guests that you guys have on the show, you guys have a pretty wide variety, but it’s narrow in certain senses. You guys don’t have a lot of people from sports, and you don’t have a lot of people from politics. And you actually see this is something that separates you guys from a Theo Von or something like that where Theo Von has obviously made the decision a few years ago basically like I’ll have on the biggest guest possible, which is how you end up with episodes with somebody like Aaron Rodgers or whatnot. You guys pretty much avoid that.

Chris Black:
And to be clear, Theo Von is a master of the form. I don’t listen to it, but the Timothee Chalamet episode of Theo Von is about-

Max Tani:
Insane.

Chris Black:
... as podcasting gets.

Max Tani:
Yeah, totally.

Chris Black:
It’s unbelievable. Jon Caramanica wrote a very long article about this for the New York Times.

Max Tani:
Yeah. That was a great piece.

Chris Black:
That’s a great example of something that really explained it well, even as a person who’s super hyper aware of what it is.

Max Tani:
Yeah.

Chris Black:
And I think that the reason something like that resonates so much and why he can talk to everyone is because he has this ability to just... He can be vulnerable, and he can be a total idiot, and that’s the human condition in a lot of ways. You know what I mean? I think he’s a good example of that, but I think that fame doesn’t interest me as much as being interesting. And that’s why I think we’re happy to talk to a first time novelist or someone like Nate, This is Lorelei.
Those are great examples of like, “Well, I really like what you did.” So I think you’re interesting. So let’s talk about it versus an actor that is doing a different thing every 20 minutes for the next two weeks. And don’t get me wrong, we’ll do some of that obviously, and we’ve seen it over the years, and we’ll probably end up doing more of it. But to us, the ultimate goal is an interesting and entertaining conversation, and that’s the God that we serve. That is it.

Max Tani:
So I’m curious, there’s a lot of talk over the last year about the manosphere. Do you guys feel left out of the manosphere discussion? Nobody’s putting How Long Gone in there with Rogan and Theo Von and these other guys.

Chris Black:
I’m happy to be left out of that conversation, just like many other conversations. I’m happy to be left out. I don’t care about that world of entertainment. I don’t care.

Max Tani:
Yeah.

Chris Black:
Obviously, I’ll watch a Rogan clip when Adam Duritz from Counting Crows is on, but I’m not going to watch him talk to a scientist about how the Earth’s flat. I don’t care. Obviously, Jason and I talk about exercise and food and things that fall into those categories, but we’re not going optimization 4:00 AM Huberman mode. And I think that is you either have to be a Trump supporter or Huberman mode to get placed in the manosphere, and I think those are two things that we aren’t. We’re lucky in that way.

Max Tani:
I do think that what you guys have tapped into is maybe an equivalent version of that for left-leaning guys-

Chris Black:
Totally. Totally.

Max Tani:
... where there’s clearly a male friendship aspect to the show that people feel a similar type of connection to you guys. They feel like they’re just hanging out with people they know.

Chris Black:
Totally.

Max Tani:
It’s very interesting. I wonder if you have this phenomenon. I was having a conversation the other day with a podcast executive who was saying that.. And I’m going to totally butcher this, but, “People, when they introduce themselves to people they know from television, they’ll actually greet themselves and they’ll say hello. They’ll start a conversation.” People when they go up to a podcast host, they enter into a mid-conversation in the sense that they feel like they know you already. They act like they do. For example, I’ve listened to the show a bunch. We’ve met in passing once, but I feel like I could figure out where this conversation was going to go just by having listened to you for hours and hours.

Chris Black:
Oh yeah, for sure. That’s the beauty and the curse of podcasting. The parasocial shit is extremely, extremely real and can get very dark. It’s interesting. Yesterday, a guy came up to me and literally showed me his phone, and he was like, “Holy shit, I’m listening to you right now.” And that happens pretty often.

Ben Smith:
Do you like that?

Chris Black:
Yeah, that’s funny. That’s fine. People say what’s up to me. No one’s trying to engage that much. They want to say hello. They want to shake your hand. But how do you not like that? It’s humbling for someone to care about what you’re doing. Our fans, I think, in a lot of instances, you turn the dial to the left, there are peers. A lot of the time, they’re people I might want to socialize with or we have a lot in common.
I think that’s the beauty of revealing part of your life three times a week. It does attract a person that they have similar views and similar interests. So therefore, it makes those kinds of interactions like that much better and easier.

Ben Smith:
How’s the business of How Long Gone? Has it been life-changing for you?

Chris Black:
I wouldn’t say life changing. I think it’s been good. I’ve always been a very social person, and I was always out, and that was always what I did. I think now, I just get to interface and spend a lot of time with people I really respect what they do, and I really get to be around people that I think are truly at the top of their game. And I don’t think there’s any monetary value you can put on that.
I think that’s enriching in my life in a way that money can’t be. That being said, would at I like to make more money, absolutely, as always. Absolutely. But I think that is really when I step back and look at How Long Gone is and what it’s become, and I think it is like a male friendship thing. Jason and I are real friends. We’ve been friends for a long time. We hang out together. We talk to each other every day. Our wives are friends. That’s real.
I think people feel that, and I think that’s part of the reason we’ve attracted this group of people that a lot we’ve met on the show. You know what I mean? A lot of people we’ve met on the show become real, real friends. And the business of it is good. It’s advertising. It’s as good as it can be. Our ads are sold out. We do a lot of brand partnership stuff, and that does well. We do the red carpet stuff, which is great. I think that the TV thing or the visual thing is the next real hump that we’re going to figure out.

Ben Smith:
Yeah. It sounds like you’re about to level up into a much more expensive world. That’s the thing about TV, is that you can charge a lot more view also. It just costs a lot more. Suddenly, you got half a dozen people running around carrying boxes and lights and things. Do you think this moment both for you but maybe also for the industry is ending this moment of these more informal, lower production, more intimate spaces?

Chris Black:
I hope not because I think there is some charm and value to it. I don’t think it will affect the product. I don’t think people putting cameras down is going to change what they say necessarily. But I think it changes the dynamic, and that’s why we’ve been so resistant to it because we could do it just like we’re doing it right now. You know what I mean?

Ben Smith:
Yeah.

Chris Black:
And have somebody cut it up and make it a thing. Then you’re asking guests to be on camera. Then they’re asking about hair and makeup. Then they’re asking about it. It becomes a whole different challenge.

Ben Smith:
Yeah.

Chris Black:
I think that’s why we want to approach the visual stuff with just a different concept.

Ben Smith:
The thing is you’re going to then force everybody else up market. And pretty soon, Max is going to hair and makeup. I can just see it all coming.

Chris Black:
This thing’s going under quick once Max is asking for a car service and hair makeup.

Max Tani:
Yeah. We’ll ask Think with Google to put that in the next contract. Chris, so how big is the show now? I feel like the last number we saw that you guys put out was that 500,000 people were listening a month. What does that look like now?

Chris Black:
Honestly, I hope it’s more. That’s not my department. I’m not exaggerating. I don’t look at numbers. I don’t look at anything. That’s Jason. It’s weird. I just don’t care. That’s not the point to me. When we do shows, our agents send us ticket sales reports. I don’t want to see it. I don’t want to see any of the shit. I want to show up, do my job and do it to the best of my ability, because I think once you start getting wrapped up in that shit, it’s like... Ian, the guy who owns TalkHouse, our network, he tells us it’s growing, and we’re sold out on ads. That’s the information I need. I’m not a numbers junkie. I’m not a tech guy. I don’t care about that. I just want to do a good job.

Ben Smith:
I came up in a world where what you were saying was what the dinosaurs said and that the response was, “Come on. Don’t you care about your audience?”

Chris Black:
Yeah. No. I care about them because I want them to be there, but I don’t know if understanding... How does me studying the P&L of numbers and reports going to positively affect the performance of the podcast? It’s no. You know what I mean? It’s not. It’s going to get in my head and make me think about things that are going to distract me from actually doing what we’re there to do.
And I think we have a team of people that look at those numbers. That’s why we are represented by CAA and fucking all. We have all the shit because those numbers are good enough. And I assume that if those numbers dip below these standards, somebody’s going to let me know unceremoniously. That’s not how my brain works, is really the simple thing. The simple thing.

Max Tani:
Yeah. Are you keeping track of how much money you’re making from the pod? Because Kara Swisher told us that she’s making $20 million from the pod with Scott Galloway. Are you guys in that neighborhood or is it maybe a little less?

Chris Black:
We’re right there. We’re right there. We’re the hair under. The Scott Galloway thing, I don’t get it. He came on How Long Gone. I don’t get it. Those guys have a script, and I respect it, but you cannot get him off it. And that to me is just not fun. I get that, that builds you a following.
Kara Swisher, I’ve never understood. That’s just not my world. But I think that again, they’re making a lot of money also because they’re speaking to an audience that is making a lot of money. That’s the whole point. Our audience makes a lot of money at a certain level. They aren’t guys who have vested at several various tech companies. That’s not necessarily our audience.
The guys who founded Sweetgreen might listen to How Long Gone. But the guys that are C-suite at Google probably aren’t, and that’s fine. But I think that the money thing is, obviously, always on our minds because all we see is people getting rich. Whether it’s SmartLess doing $200 million or fucking Alex Cooper doing her thing or whoever. It’s like we see that more as our world than some of the smaller stuff that we actually get grouped in with because it’s aspirational. SmartLess is doing exactly what we do, but they’re rich, and that bothers me. You know what I mean? That bothers me. They came in with huge audiences, obviously. They’re famous. It’s a different thing, but I think about money all the time, but in a way of how do we increase it without doing stuff we don’t want to do.

Ben Smith:
So what does it bring in a year, if you can say?

Chris Black:
I’m not going to say. I’m not going to say. Honestly, I wouldn’t be that accurate, but it’s like Jason and I, he edits the podcast. He spends a lot of time with the actual product.

Ben Smith:
It sounds great.

Chris Black:
He takes a 60%. I take a 40% because I think that’s fair. I come from the music business where it was like you would hear the story of U2 splits everything equally with your manager, Coldplay. And that’s why they’re together. That’s why they’re successful. You want everything to be right. Business-wise, you want it to feel good. And will I regret that decision if we start pulling in 20 million? Maybe a little bit. But that’s fair. That’s just what’s fair.
And I think that when you have a true creative partner and you feel like you found each other and it’s really positive, I can always go find a way to make money. I’m not going to sacrifice something great to make more money. I’m just not going to do it.

Max Tani:
So let’s end with some recommendations from you because you do that. You do it for The Strategist. You already put our listeners on to Carter Young, Ven. Space. What else are you really interested in right now? What’s been really fun that you are wanting to put people on?

Chris Black:
I really love this new Jon Hamm show on Apple TV.

Ben Smith:
Oh, the Apple TV+ show, Your Friends & Neighbors.

Chris Black:
Yeah. I really like it.

Ben Smith:
Yeah, I like it too.

Chris Black:
The music is really good. I think that Hamilton Leithauser is doing some of the music, but last night, there was a song from this band, Tanlines that is a classic that I was like, “Wow, this is so cool.” And then the Sons band covered Matthew Sweet. There’s little tidbits that really speak to me, but I love the show, and I think Jon Hamm is a national treasure obviously.
Honestly, because I’m in my book writing in that zone, I’ve been reading a lot, and I think that that has become so much harder as I’ve gotten older, and there’s so many more distractions. There’s a book called Rejection I really liked. I’m reading the new Natasha Stagg novel that comes out later this year. Obviously, the Graydon book, the Keith book, the Conde Nast book.

Max Tani:
I do feel like we’re all being kept busy. People who are interested in media are all being kept busy by all of these books about Conde Nast, Michael Grynbaum, which has the one that you’re referencing that’s coming out pretty soon.
Well, Chris, we really appreciate you coming on the show. It’s been really great. You’ll have to come on again and share some actual specific concrete numbers when you guys are hosting.

Chris Black:
Yeah. You know what?

Max Tani:
Actually hosting the Emmy;s.

Chris Black:
I’ll fax over the bank statements once we’re hosting the Emmy’s. And just text me the number, and I’ll fax those over.

Max Tani:
You got to ask.

Chris Black:
No, that’s your job. I appreciate it.

Max Tani:
No, we were surprised though by Kara’s. We asked Kara how much she made.

Ben Smith:
She was so candid. So now we ask everybody else, the Kara Swisher rule.

Chris Black:
Well, guys, let me me explain something. Like I said, if we were making 20 million, I would’ve said 20 million.

Max Tani:
You’d be sharing that.

Chris Black:
Yeah. That’s why she’s sharing it. That’s the coolest thing you can say. It’s like sports contracts are all public. Why not?

Max Tani:
That’s true. That’s true.

Chris Black:
Thank you, guys.

Max Tani:
Thanks again.

Ben Smith:
Thanks, Chris. Good to see you.

Chris Black:
Yeah, good to see you guys too. I’ll see you soon.

Max Tani:
Sounds good.

Chris Black:
All right. Later.

Ben Smith:
So Max, did that live up to your expectations?

Max Tani:
Yeah, it was really great. One thing about Chris which is really cool, is how generous he is with his time when it comes to media. He’s one of the few people whose job it is to be professionally cool, but also clearly has a love of the game. He’s reading multiple Conde Nast books at once. He has a newsletter that he and one of his business partners publish every day. That’s literally just like a lot of stories, I found it, because he had linked to some Semafor stuff, and he’s clearly just paying a lot of attention, and he’s a lover of media. And so it was really great that he came on and gave us so much time.

Ben Smith:
It’s too bad Conde Nast hasn’t found a way to capitalize on the interest in old stories about Conde Nast. It seems that sometimes outstrips interest in current Conde Nast products and content.

Max Tani:
No, it is true. People really loved the Tina Brown war stories that she was telling on our show, even more so than people want to know about what’s going on there today.

Ben Smith:
But yeah, Chris, it’s funny because as we discussed, I don’t think I totally got what Chris’s deal was. And, in fact, was introduced to him during the pandemic, and we had this mutually total incomprehending encounter in LA.
But I do think the level of clarity with which he’s thinking about media, that impulse that institutions are cool was really, really interesting. And that this social media moment, the Substack moment is running out of steam, I think is a really very interesting observation. It is going to propel a lot of reconsolidation, basically. Gatekeeping,

Max Tani:
Yeah. Right. Gatekeeping is back a little bit. I think that what Chris understands is the value of partnership with powerful institutions, which still have a lot of juice left. And I think part of that is just the fact that he, in some ways, has so much experience in the business world that he’s not averse to collaboration. One of the things that defines a lot of the successful Substacks is it’s full of people who are just really bad at working with larger institutions and have to be on their own to really be fully creative and interesting.
And I think Chris clearly works well within teams settings, which is something that’s valuable in media and institutions. What do you think then?

Ben Smith:
Yeah. I think he also comes out of a world fashion that’s obsessed with quality, with technical quality and with aesthetics over scale, over audience. And that’s a very different impulse, the sense that we’ve got that things have to be crafted. But I think he mentioned the FT. I think there’s something about the FT and FT weekend right now that is very hot, that is a reaction against this every Substack which I love many Substack that could all be 30% shorter, but that takes longer and takes more editing, and I do think that Chris definitely speaks for a tendency that’s pretty real.

Max Tani:
Yeah. Of course, there is a little bit of irony here, which is that How Long Gone is one of the more successful independent podcasts. They’re part of a network but really clearly do most of it themselves, and it’s flourished based on just their independent impulses.

Ben Smith:
Yeah. And it’s shaggy and low production, but beautifully produced actually. His partner is a DJ, an audio producer.

Max Tani:
Yeah. And the question is at what point does it get absorbed into the mainstream? He talked about some of the red carpet stuff they’ve done. They’ve done some partnerships with GQ. I believe that they did some stuff on the red carpet for the Emmy’s as well. The question is at what point does that become more formalized and less like, “Hey, here’s this cool gimmick. We’ve got a few podcasters who are also doing something on the side here.”

Ben Smith:
You see where this is going. They’re getting a band.

Max Tani:
Yeah, right. That’s true.

Ben Smith:
I think that was a scoop they’re basically developing. I think the other word for what he was talking about is they’re developing a television show.

Max Tani:
Yeah. And it actually makes a lot of sense because most of their guests are from music, and so why wouldn’t they play or drop stuff on the show, like an old radio show where you might drop a single for the first time or something. There’s obviously cool interesting potential there. And also, it gives you an incentive to listen and might bring in new audiences and whatnot.

Ben Smith:
I also really liked the sophistication about, I do think that that’s a real wise point about business, that in negotiations, you want to leave a little bit on the table. That’s something one of a mentor of mine told me, and I do think that for long-term partnerships to succeed, you don’t always want to scrap for every penny.

Max Tani:
I disagree with him though, about paying attention to the metrics. I’m refreshing our YouTube page every day to see which shows are going off more. I can’t help myself. I think it’s important.

Ben Smith:
That’s because we haven’t made it yet.

Max Tani:
That’s true. That’s true.

Ben Smith:
It’s easy for him to say.

Max Tani:
Yeah, that’s true. Once you’ve hit a good marker, you can stop paying attention. But before that, you’ve got to be thankful for every hundred extra viewers on Jen Psaki’s YouTube video that come in every week.

Ben Smith:
Well, thank you for bringing Chris by, Max. That was fascinating.

Max Tani:
Yeah. It was so fun. Thanks for listening to Mixed Signals from Semafor Media. Today’s episode was produced by Chris McLeod from Blue Elevator Productions. With special thanks to Max Toomey, Britta Galanis, Chad Lewis, Rachel Oppenheim, Anna Pezzino, Garrett Wiley, Jules Zern, and Tory Core. Our engineer is Rick Kwan, and our theme music is by Billy Libby, who I recently met. Our public editor is Will Welch.

Ben Smith:
And if you like Mixed Signals, please follow us wherever you get your podcasts. Please subscribe to us on YouTube.

Max Tani:
And if you want more, you can sign up for Semafor’s Media Newsletter out every Sunday night.