Hosts Lawrence Schlossman and James Harris bring quick, irreverent humor to the niche world of menswear podcasting. (Illustration by Yunyi Dai, Maryland Institute College of Art)

The Emperor Has No Jawns: How ‘Failing Upwards’ Demystified the Fashion World

Using transparency and self-deprecating humor, hosts Lawrence Schlossman and James Harris are democratizing style.

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Hosts Lawrence Schlossman and James Harris bring quick, irreverent humor to the niche world of menswear podcasting. (Illustration by Yunyi Dai, Maryland Institute College of Art)

Using transparency and self-deprecating humor, hosts Lawrence Schlossman and James Harris are democratizing style.

On the Season 7 premiere of “Failing Upwards,” podcast hosts Lawrence Schlossman and James Harris were introducing their guest, Chris Gibbs, the proprietor of the Los Angeles clothing store Union, to listeners. As they launched into the episode’s first segment, a bit called “Fit Check” wherein the guest describes, from head to toe, the outfit that they wore to the studio, Gibbs gave pause.

Harris, sensing their interviewee’s hesitation, probed, “Oh you’ve never actually listened to the podcast?” Gibbs demurred, admitting that he had, in fact, never actually listened to the fashion-cum-entertainment program before. “That’s okay,” responded Schlossman, “You wouldn’t have agreed to come on if you had.”

Over the course of the next hour and a half, Schlossman and Harris, with occasional input from their intern and stoic fall guy Charlie Franco, subjected Gibbs to a gauntlet of uncouth questions, roasts and gags. Fans of the podcast, known affectionately as the Fail Gang, would recognize the ordeal as the basic template for every episode.

Though the exact format has fluctuated over the course of the podcast’s eight seasons, most episodes now follow a basic blueprint: begin with Fit Check, segue into Fuck With/Not Fuck With (a working title), then launch into the three, self-proclaimed subjects of the program: Money, Ourselves and Dat Ass, which themselves contain a number of preset questions.

Though every episode does ostensibly follow this formula, the real star of the show, as is the case with almost any good podcast, is the banter. Schlossman and Harris both hail from the media world, as the two met while writing for Complex and remained friends even as they both left the pop culture bastion for different jobs. Whether you have read their work or not though, their background in the literary world makes itself clear relatively quickly.

The two are notoriously quick-witted, leaping from obscene joke to double entendre to political jibe to obscure reference with ease. And, when this improvisational humor is paired with their obsession with pop culture and the world of fashion, the result is an intimidating blend of high- and low-brow culture, gilded with an internet-savvy salvo of crass jokes and memes.

Their guests, in the face of the hosts’ chaotic energy, sink or swim. Chris Gibbs, for example, despite his comparatively lower words per minute, turned out to be one of the best guests of the season. As the “Failing Upwards” creators will attest to, because of the miscellaneous nature of the topics they cover, the best visitors are not necessarily the most pedigreed ones, but the ones most willing to play along. “A good guest,” Schlossman told me, “can come in and, yes, they might be a little shocked, but they’ll have an open mind and won’t take themselves too seriously.”

Indeed, the quality that Schlossman claims is the common denominator of good guests — a willingness to laugh at themselves — is the same quality that has attracted nearly 10 million listeners (give or take a million) to “Failing Upwards.” At its most fundamental, the podcast explores the ins and outs of the fashion world; it does this through a variety of ways, some more roundabout than others, but clothing is at the heart of every discussion.

However, fashion has always been one of the most self-serious of all the creative pursuits, and as a result it has generally attracted a very anal fanbase. From media like “The Devil Wears Prada” and “Zoolander,” to eccentric figures like Karl Lagerfeld and even Kanye West, the stereotype surrounding the industry is one of people who take themselves too seriously.

“Failing Upwards,” then, which was born of a doomed video series Schlossman and Harris created at Complex, illuminatingly called “Fashion Bros,” is predicated on upending that stereotype. The two riff on each other, seemingly to no end; they riff on their guests to whatever degree they feel appropriate; and they riff on the shibboleths of the fashion world, making it to no degree unclear that they consider all subjects fair game and no criticism too heretical. Through their humor, Schlossman and Harris are democratizing an industry that has historically been an insular one and opening the doors of a world that has long been rooted in exclusivity.

None of this, it should be noted, is an accident. For starters, if we’re being specific, “Failing Upwards” is much more concerned with the world of streetwear, a subset of the larger fashion world that arose from the skating and surfing subcultures of the 1990s, than it is with esteemed clothing houses of old. In fact, Schlossman, Harris and Franco, who occasionally functions as the podcast’s third mic, share an obsession with several of the same brands, whose products they routinely plug.

Blundstones, for one, and the concept of wearing Blundstones (or Blunnies, as they call them), have become a meme of the program simply because of how often the podcasters mention them. Other brands, such as Online Ceramics and Our Legacy, are also favorites. Their predilection for these non-canon clothiers has helped establish the podcast as a haven for sartorial underdogs, which further underscores their reputation as a fashion podcast for fashion outsiders.

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What’s more, Schlossman and Harris themselves lack the pretense typically associated with couture culture. Unlike the starched talking heads that generally expound on the latest clothing trends, the podcast hosts are informal, even bro-ish. They talk openly, and self-deprecatingly, about their “jawns addictions,” making frequent jokes about the Sisyphean nature of buying clothes to fill the existential holes in their lives.

Many of the memes they circulate on their social media express a self-awareness about the superficiality of their passion, but they don’t feel the need to dress up their hobby as some transcendent act of self-expression; they like fashion, but it isn’t a life or death endeavor. One running joke concerns their fear of posting a fit pic that fails to get enough likes on Instagram.

By planting their flag firmly in the ground of egalitarianism, “Failing Upwards” has enjoyed immense, and nearly immediate success. Who knew there were so many people interested in fashion who were just too intimidated to say so? The podcast’s fans are a rabidly devoted group of listeners, and Schlossman and Harris routinely employ their listenership for their own interests, such as spamming Jonah Hill’s Instagram with comments or pestering the social media feeds of “rival” podcasts.

The two speak frequently of the “Failing Upwards” difference, or of their ability to mobilize “FU” fans, and the numbers back up their claims. At least in easily measurable metrics, such as the social media followings of their guests, appearing on “Failing Upwards” correlates neatly with a massive upswing in followers.

This phenomenon dovetails nicely with their identity as gatekeepers of new media, because they intentionally choose guests who often have, by celebrity standards, paltry social media presences. “We want to continue this formula,” says Harris, “of finding people who, when we put their names on Instagram on Tuesday night for the preview, people are like, ‘Who the fuck is this?’” They pride themselves on bringing to light industry figures who are important movers and shakers behind the scenes, but might not enjoy the same level of public reception as their Kylie Jenner counterparts.

Indeed, when I first heard about the podcast from a well-dressed friend of mine, I was apprehensive. I like to think I dress passably well, but I am by no means a fashion savant. But, when I first began listening, I found myself immediately attracted to a component of their appeal that even the podcast hosts themselves rarely mention.

Because they have worked in the media industry for more than a decade, and because the guests they bring in often hail from the media industry, “Failing Upwards” is also, in many ways, a media podcast. In just this last season, alongside guests from the fashion world, the podcast also played host to writers from Complex, The Ringer, Bonobos, Futurism, Gawker and Barstool Sports — the last one being the putative and controversial employer of “Failing Upwards.”

Schlossman and Harris are aware of their podcast’s habit of moonlighting as a glimpse into the world of East Coast media elites, but the effect to them is just a byproduct — not an unwelcome one, but certainly not the thrust of their program. “Because we were able to rise,” says Schlossman, “to ‘fail upwards’ through the unforgiving landscape of new media, we can now look back with 20/20 hindsight on it. As a result, we’re able to pull out those insightful nuggets, while at the same time we’re not cutting an NPR-style interview. I imagine that would be very interesting for anyone who cares about the media industry.”

Intentional or not, the effect adds to the podcast’s air of transparency. Rather than focus on the glamor of the fashion world, their tendency to interview the figures behind the curtain, and to conduct the interview in a familial, office-gossip type of tone, demystifies a world that has long prided itself on its inscrutability.

“James and I have always said, ‘This world, while seemingly sexy to an outsider, is not really the most interesting world with the most interesting people,’” says Schlossman. Perhaps, one might be inclined to believe, it actually is; we’ve just been focusing on the wrong people.

“Failing Upwards” Interview (Edited for Clarity)

Mark Stenberg: So Season 8 officially premiered today. Do y’all have plans to tweak the formula at all?

Lawrence Schlossman: No, James and I are pretty fucking lazy, so we try not to change anything unless someone forces us too.

James Harris: This might be conjecture, but it seems like we’ve hit a stride and we’re in a nice patch of booking guests. In the prior seven seasons it’s been week to week, but as the pod grows and we expand beyond the immediate homies, we have been able to get a lot of nice guests lined up.

LS: I don’t know when this is going to happen, but I think there’s a world ahead where Chuck features more prominently, but I don’t know if that is coming any time soon.

MS: You recently got chewed out for your ad reads. Are things smoothed over with Barstool?

JH: Well I guess that’s something that’s going to change this season: for the foreseeable future we’re going to be good boys when it comes to ad reads.

LS: Yeah we’re going to stop fucking around.

JH: Back when we were doing [“Failing Upwards”] once every two months in Lawrence’s office, [Barstool] were the only ones to give us a shot, and they’ve been absolutely great. Obviously they have a certain reputation, but they’ve been really hands-off with us. At other editorial places you always have to play ball and sometimes can’t do what you truly what you want to do; at Barstool, they’ve been like, “Fuck it, do whatever you want to do.”

LS: The ad-read controversy actually proves James’ point: look how wildly out of pocket we have to be to get literally any kind of blowback. With everything else we’ve done, which has been pretty egregious by almost any standard, there has never been an issue — that speaks to a certain integrity that Barstool has. I’m not here to defend the reprehensible things they’ve done in the past, but Barstool, and specifically Erika Nardini, believes in us. We’re aboard the pirate ship and trying to play ball.

Mark: What were some of your favorite episodes from Season 7?

JH: I think my favorite episode was the premiere with Chris Gibbs, who’s a fucking legend in the streetwear scene and was a huge guest for us. He also played ball so well. I was worried we were going to turn him off by being ourselves, or that the episode was going to be too clothing-related. And then the season finale, which was this relatively unknown meme account person, Patia, who is tangentially related to the art and fashion world, that was the best time I had in the studio.

LS: With the Chris Gibbs episode, there are a lot of followers who know us from our fashion pedigrees, working at Complex and “Fashion Bros,” and expect us to focus on that world more than we do, because that’s what they tune in for. But we’ve always made the argument that, even though Complex claimed out of the gate that we were a fashion podcast, James and I have always said, “This world, while seemingly sexy to an outsider, is not really the most interesting world with the most interesting people.”

But what was awesome about the Gibbs episode was that it proved what fashion podcasting could be from an entertainment standpoint. Yes, we can help sell this guy to kids who are very interested, but at the same time, there’s going to be personalities, jokes and we’re going to put him in a compromising position — to a degree, obviously — but James and I are going to get the requisite entertainment value.

Regardless of whether you see us as a fashion podcast, a Barstool podcast, a media podcast — whatever the fuck you come to the pod for, at the end of the day, that’s the kind of episode where you get all of the stuff that makes what we do special. If there was a kid who asked me what episode I should start with, that would most accurately introduce me to the “FU” Extended Universe, as we like to call it, I would point him to that episode.

Also, we loved the Big Cat episode. Obviously Big Cat is one of the biggest personalities at Barstool, and he’s one of the most successful podcasters in the world with “Pardon My Take.” Since that episode, we have developed a close personal relationship with him, and he’s begun serving as a kind of mentor/consigliere.

He was so receptive to our shtick, it was such a good time and that episode went nuclear. More people listened to that episode than they have to any other episode, including our Jonah Hill episode. I think that proves that a podcast like “FU,” that might be a bit niche, does have some kind of broader appeal.

JH: One thing that was really interesting was that we had some guests with really big social followings, some big clout, but they didn’t necessarily put together the best episodes. Whereas the Chris Gibbs episode, and the Patia episode, who have either no social following or a small social following, show that just because you have hundreds of thousands of followers doesn’t mean that you’re going to have a great time with us. Big Cat is the anomaly there, of course.

MS: What would you say makes a good guest?

LS: A willingness to play ball. Most guests who come in are familiar with James and I, the real people, less so much James and I the characters, or the extreme versions of ourselves that we play on the podcast. A good guest can come in and, yes, they might be a little shocked, but they’ll have an open mind and won’t take themselves too seriously.

JH: You have to not take yourself too seriously, and you have to be able to express opinions. The whole conceit of the show is that, yes, it’s ostensibly a fashion podcast, but as we all know it’s not just the garments and clothing; it’s everything surrounding that: music, news, lifestyle, culture. If you’re able to provide an opinion on that, you’re going to be able to keep the conversation going. If you’re a closed-off person who’s too scared to have an opinion on things, whether we agree or disagree, it’s just going to be boring; it’s like talking to a wall.

LS: You don’t even have to be versed in our world or language. Look at Big Cat. He’s someone who could care less about the things we care about in our professional and personal lives, but at the same time, what we talk about when we talk about clothes is everything that’s besides the clothes: lifestyle, news, etc. If you’re willing to express opinions about that stuff, or probe James and I to understand the world they’ve entered for these two hours, that kind of person, who’s willing to be a little intrepid, that’s going to provide the best content for us.

MS: What guests can listeners expect in the next few weeks?

JH: The Season 8 premiere is going to be with Adam Friedland who’s a stand-up comedian in New York and one of the three mics on the podcast “Cum Town,” which is my favorite podcast and Chuck’s favorite podcast. Adam, like a lot of other comedians we’ve had on the show, is a budding jawns enthusiast and has a distinct personal look, a la Brandon Wardell, Dan Levy or Adam Pally. We’re hoping it’s going to be be really fun.

Even though “Failing Upwards” is wildly smaller than “Cum Town,” I like to think we have a lot of crossover. So my goal, besides selfishly getting to hang out with Adam for two hours, is to have a synergist moment between a true comedy podcast and our kind of weird, comedy/streetwear podcast.

JH: And the week after that, we’re bringing in the man behind my hands-down favorite brand, the Swedish brand Our Legacy, founded by Jockum Hallin. When Lawrence and I were first starting out, one of the first things we had to do was put on a tradeshow for emerging menswear brands. We developed a few relationships with these brands, and one was Our Legacy. When I was at Complex I would follow them and write about them, and through the internet got to talking to the designer.

When I was in Sweden last summer we hung out, and he said, “What’s up with ‘Fashion Bros’?” And I said, “Yo, we do a podcast now,” and he goes, “What the fuck?” Then I blew thousands of dollars at the Our Legacy store, and all of a sudden he starts DMing me jokes from the episodes. And if you can imagine a Swedish, cool, creative guy DMing me, “My G!!!!!!!!!” it’s hilarious. So we’ve kept in touch.

I literally wear Our Legacy like every day; I’m wearing two items of theirs right now, but usually it’s like three or more. So Jockum’s coming to New York and coming on the pod. He’s so fucking cool, has the best taste in the world, is a huge fan of “Failing Upwards” and has a self-deprecating sense of humor, so I’m confident that it’s going to be on the same level as the Chris Gibbs episode: super cool legend that’s really successful, a guy who everything he touches turns to fire. He’s going to come and we’re going to put him through the gauntlet.

LS: The cool thing about Jockum, and we’ve had guests like this in the past — a great example of this would be Sam Lerner — is when we have a guest who’s familiar with the show. Whether they’re a super guest like Sam Lerner or just tangentially aware of the segments, that to me always makes a great episode. Not just because James and I like getting our dicks sucked on the microphone, but if they’re already familiar with the “FU” extended universe it makes for these special moments for the fans.

JH: Looking ahead, we’re going to continue this recipe of finding people who, when we put their names on Instagram on Tuesday night for the preview, people are like, “Who the fuck is this?” We’re not going to put someone on the show who isn’t going to cut a slap. Lawrence and I like what we like, so we’re going to keep bringing people in from those worlds. So if it’s a D-list reality show on Bravo but we like it, we’re going to bring them on. If it’s one of the biggest rappers in the world who we like, we’re going to try and bring them on.

MS: Do y’all consider yourselves writers first and fashion-heads second, or fashion-heads first and writers second?

JH: I mean we’re both in the content world, but to your earlier point, nothing exists in a vacuum anymore. To Complex’s credit, they were the early pushers of convergence culture: you’re not just a music fan, you’re not just a fashion person. For me though, I would say it’s fashion first, then media.

LS: We bring an interesting perspective because we were young, new media go-hards. Because we were able to rise, “to ‘fail upwards” through the unforgiving landscape of new media, we can now look back with 20/20 hindsight on it. As a result, we’re able to pull out those insightful nuggets, while at the same time we’re not cutting an NPR-style interview. I imagine that would be very interesting for anyone who cares about the media industry.

But one of the amazing things we have is that James is a very good interviewer and writes very good questions for our run of shows every week. He’s able to pull that stuff out of people while I lay in the cut being a ridiculous asshole. To James’ point, I consider myself a fashion-guy first, rather than an editor.

JH: There’s really no such thing as a specialist anymore. We’re going to have guys on like Foster Kamer, who can’t talk about the hand-stitched qualities of denim from Japan, but he does fuck with Playboi Carti. Everybody has overlapping interests — I care about music, I care about politics — but my primary interest is jawns. But that doesn’t mean I’m not able to converse about the other things, so we’re going to have people on like Big Cat, who’s a jock through and through, but can talk about sneakers. In this media world, everyone is plugged into everything to some capacity.

LS: This is the age of the multi-hyphenate. Because of social media, everyone is at least an armchair enthusiast for a lot of different things. So it’s always fun for guys like James and I, depending on the guest, to pick different lanes to dive into. The Foster Kamer episode is such a great example — what other Barstool podcast is going to bring in a guest who trashes Barstool? Who is going to talk about the heyday of Gawker, when they were burning shit down from the inside? That’s something that’s special about James and I. If everything else blows up, the episodes we have banked offer an insightful look into a variety of things.

MS: I wanted to avoid asking y’all the questions you ask your guests, but I have to make one exception. What advice would you give to young professionals interested in making it in the media industry?

LS: For me it’s simple: Self-awareness is the greatest commodity of the human condition. A lot of kids will hit me up because they want to be a writer, but if they’re trash writers, maybe don’t try to be a writer. Maybe you could be an editor? Know your strengths, know your weaknesses. Finally, don’t do it. There’s no money, it’s a dying industry.

JH: Be dogged. But also, don’t be annoying. Be opinionated: don’t just trash everything, but if you co-sign everything it’ll be obvious that you’re corny and just chasing clout. To Lawrence’s point, if you want to enter media and make money, the actual money is with brands.

LS: Also, a lot of kids miss the mark on professionalism. They sacrifice decorum to be chill and approachable, so if a kid hits me up and says, “Yo, what up you fucking loser? You want to hire me I’m fucking chicks.” You think that’s what someone like me would want to hear, but at the end of the day James and I are able to book all these guests and have all these relationships because we were always ourselves, but we were still professional and respectful.

I’m not saying people need to kiss the ring, but I do think that a lot of young people miss the forest for the trees. They miss that decorum that is important when you’re reaching out, essentially asking for something, where they’ll be getting nothing for that. You should be quasi-professional, and a lot of kids are missing the mark on that.

MS: Any thoughts on one day moving to a video platform? Or is the dream to stay with the podcast?

JH: Our lives are both pretty miserable; Lawrence just got married so his life just got exponentially more miserable. But the two hours we have every week to pod is this nice oasis where we put our phones down and just talk to people we want to talk to, so I think primarily we’re just focusing on maintaining the quality of guests we’ve had so far.

We’ll turn down people with millions of followers if they suck, and sometimes our favorite people are just busy. We do things that are pod adjacent, like the Bonobos look book — Jonah Hill day last summer was obviously fire — but because we know how time-consuming video is, given the very little time and energy we have now, we’re not really thinking about it at the moment.

LS: Right now the podcast is the perfect amount of getting paid to do something we love, and if we ever wanted to expand, we would just want to be compensated properly. The biggest bummer with “Fashion Bros,” besides that it flamed out, is that we never were properly compensated for it. We were young and hungry and just jumped into it, but now we need to be compensated properly.

One of the best things about the podcast is that we get paid for X amount of work that we do and it feels fair. We’re never turning down offers, though; we want to do cool shit, we want to do things our fans would enjoy and we evaluate things on that scale.

Mark Stenberg

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