How To Succeed in Podcasting Without Really Trying

By Ben Roazen
Photos by Tory Rust

Most podcasts are intricately tailored listening experiences: hosts speak in measured tones; guests take turns talking and everybody gets their shot at the mic. Not so on Failing Upwards, the self-proclaimed “Only Podcast That Matters.” Hosts James Harris and Lawrence Schlossman often overpower their guests, so much so that their dynamic has become one of the infinite in-jokes from the Failing Upwards Universe (or FUniverse, as I have just dubbed it).

There are some regular segments on the show, but it’s not uncommon for the two hosts (and their production team) to veer wildly off-script at any given point. “We go full turbo, every time,” says Harris. “Listening to us is like pouring Mountain Dew Code Red directly into your ears.”

The pod’s ad-reads are hilarious and absolutely unfit for print. Every single brand that gets name-dropped on the program is implored to “sponsor the pod.” The show’s first on-air sponsorship came from Complex’s food vertical First We Feast, who bought the gang their first piece of audio equipment — a basic sound mixer (estimated retail price: $150) — in exchange for an ad-read where James and Lawrence repeatedly called Hot Ones host Sean Evans a “beautiful, bald bitch.”

Lawrence wears the Jetsetter Stretch Italian Wool Suit (Brilliant Navy) and the Thaddeus x Bonobos Cabana Shirt (Blue Seashore Seagulls), James wears the Jetsetter Stretch Italian Wool Suit (Light Navy) and the Thaddeus x Bonobos Cabana Shirt (Navy Windowpane)

“We find the pockets and we just exist in them,” says Schlossman, of their ad-reads: “it’s like jazz.”

We met up with Failing Upwards’ hosts in Soho to talk about the pod, how they turned a hobby into a part-time job, and how they got Jonah Hill to show up to Jonah Hill Day.

When we first start recording, the duo is motor-mouthed and talking over each other — right in step with their signature interview style. Eventually, though, they settle into a routine: Schlossman talks at a feverish clip — at around a million miles-a-minute — with parentheticals and tangents that jump from memes to business buzzwords like “audience momentum;” Harris, meanwhile, is relatively laconic, naturally playing off Schlossman’s colorful commentary.

Failing Upwards started in May 2016. “We were doing this bullshit on our own in the old Grailed offices,” Schlossman pointing out the window of Grailed’s newer SoHo HQ: “after hours, just putting in work in the gym, bro.” Harris remembers raiding the Grailed kitchen for Zapp’s Hot Voodoo potato chips.

“We were clout-chasing,” corrects James. “When we work together, whether we’re working hard or just fucking around, we do produce a very specific kind of content that a very specific kind of kid enjoys. We were having a good time. Our show is all about doing the bare minimum, hence the whole Failing Upwards moniker.” James and Lawrence then depart on a tangent about the gall of them turning their hobby into a part-time job. “Like, think of anyone doing a podcast: you really think you’re worthy of recording a conversation? That other people are going to listen to in their free time?” At this, James leans into the mic recording our conversation and shouts: “Yeah, who the fuck do you think you are?!”

James wears the Jetsetter Stretch Italian Wool Suit (Light Navy) and the Thaddeus x Bonobos Cabana Shirt (Navy Windowpane), Lawrence wears the Jetsetter Stretch Italian Wool Suit (Brilliant Navy) and the Thaddeus x Bonobos Cabana Shirt (Blue Seashore Seagulls)

The original Failing Upwards show touched on fashion, sure, but Schlossman points to the show’s early, conversations of something a little deeper than that: “this was not a podcast about how to tie a fucking four-in-hand knot, okay?”

There are many early episodes of Failing Upwards that touch on bigger themes: responding to the headlines, hating the holidays, personal stories about Kanye West, and 9/11. But it quickly it pivoted to being more of a guest-interview setup. The guests on FU are sometimes-fashion-adjacent media types: Hot Ones host Sean Evans; former Complex producer and KITH creative director Emily Oberg was the show’s first guest; Fashionista EIC Alyssa Vingan Klein has been on a couple of times; The New York Times’ Popcast host Jon Caramanica. (Full disclosure: your author has also appeared on the pod.) The guests are all “the homies,” says Schlossman, “apart from the occasional Bravolebrity, that we’re able to wrangle because James and I are passionate about Bravo Original Programming.”

The show’s subject matter, as described by Schlossman is “enlightened bro shit,” a term he coined and one Harris does not like. Their audience of enlightened bros is just as likely to discuss the details of kimonos as they are the politics of Kanye West’s ye,for example. (They are men of culture, after all.)

When I ask what made the two friends, busy as they were with their day jobs, sit down and shoot the shit for literal hours on end, James gets pensive. “I do think the biggest motivator initially was to sit down and talk shit and hang out,” says James. He goes on to talk about how it was an opportunity to be unapologetically real, when others may not have been so assertive (or aggressive). Blogs would never put a designer on the spot and ask them how much they made, for example. “No one was being honest about what they thought or how they felt. We could go on here and say we actually think that fucking sucks. Or we could say that the reason no one was saying that this fucking sucked is because they paid whoever, blah blah blah.”

“Beneath the jokes and the hot fashion takes,” says Lawrence, “I think because we’ve worked in fashion for so long and we do care about clothes, there’s a sincere level of criticism, both of media and of fashion.” He gets careful here: “I don’t wanna present ourselves as some kind of deep, profound podcast,” he says, “but we do care. We wanna be critical in a fun way that is hopefully harmless, but also sincere.” James tags back in: “Cynical-slash-sincere honesty. Four Pins embodied a lot of that; Complex Style when I was running it had its moments of speaking freely. Now that we don’t work at those places anymore, we needed a platform.”

Eventually, media companies that had once pivoted to video and cut their editorial staffs ended up pivoting to the pod — Barstool Sports was among them. “It was a perfect time for us,” says Lawrence, “Barstool were building their podcast presence off the strength of Pardon My Take (Barstool’s flagship sports show).” Some conversations later, the boys sold their souls to the Stool.

Schlossman recalls: “I saw that Barstool had a million things floating in the ether, so I just told them that I did a podcast with the same guy from Fashion Bros. It’s low-quality, low-budget, but with some support and incentivizing (read: put a little money in our pockets), and we’d be motivated to work on the pod.”

When Barstool relaunched the pod in September 2017, Dave “El Presidente” Portnoy proclaimed: “If You Care About Fashion (You Should) Our New Fashion Podcast Failing Upwards Launched Today.” Being labeled a fashion podcast on a sports platform — especially given fashion’s obsession with visuals — has been a challenge for the hosts. “They shot us in the foot with that,” says Harris, “Because we’re not a fashion podcast. But I think that the Stoolies that did give us a shot have stuck with us because it’s just an entertaining show.”

Earlier this summer, menswear media embraced the most unlikely of icons in Superbad star Jonah Hill. The Summer Of Hill brought an insane level of scrutiny to the Moneyball star’s every sartorial move: there was the Jonah Hill Fit Watch on Twitter, spearheaded by Lawrence’s Four Pins account; then there’s the @jonahfits Instagram account, which is run by a friend of the pod. But as Hill cultivated a super-sincere, super-earnest Instagram presence, it seemed like you couldn’t escape him: here he was dyeing his hair Manic Panic pink; there he is blasting a cig while wearing Palace and Grateful Dead tees; his oversized water bottle became a literal must-have item; he became the Biggest Mood. And through it all, the Fail Gang swarmed in Hill’s Instagram comments, flooding it with jokes and invitations to come on the show.

The Summer of Hill hit its zenith at James and Lawrence’s “bad idea for a great day party,” the second annual Jonah Hill Appreciation Day. The meme had become self-aware: Jonah Hill showed up to his own party, creating an absolute scene. The actor shook hands, took selfies, and generally had a great time in a room full of fans. “The party was set up to be fun. But then Jonah shows up and the whole thing goes full nuclear viral,” recalls Schlossman. “We’re on the front page of Reddit, proper.” Then Hill appeared on Jimmy Kimmel to talk about the party. It’s perfect late-night fodder: Hill admits that he knew of the first year’s party, but couldn’t bring himself to attend; when he caught wind of the second annual event, he forced himself to overcome his anxiety. Enlightened bro shit had gone mainstream.

In an interview about the party with The Cut,James held Jonah up as an ideal. Lawrence makes a pointed observation about Jonah being an avatar for a lot of young men, particularly in the Fail Gang: “You can naturally become a better version of yourself through self-improvement, through confidence, through supporting the homies.”

James and Lawrence also recognize that Hill could be an avatar for the hosts themselves. “We’re relatively the same age — we’re 31, he’s 34 — look, we get it,” admits Schlossman, “and his career trajectory of going from a goofy dude that is now taken seriously is something we can relate to.” Everyone loves a good underdog; in these trying times, the best soundtrack for your morning commute might not be the measured tones of Terry Gross, but a mumbling, bumbling success story, told in real time. Because sometimes, as Schlossman notes, “if you call yourself a professional podcaster for long enough, it’ll actually happen.”

“Yeah,” says James, “we’re proof.”

Ben Roazen is a writer, editor and producer in New York City. He has written for HYPEBEAST, The FADER, and GQ. He is on Twitter.

Ben Roazen