Tune In to Pineapple Street’s Podcasting Revolution

On a Monday so windy even the Brooklyn Bridge seemed to sway, two of New York’s leading cultural critics sat on matching chairs in a DUMBO studio, perched on their heels like kids at story time. Jenna Wortham, wearing all black cut with a graphic button-down, grinned. On the floor beside her lay a folded copy of the New York Times. Across sat Wesley Morris, her Times colleague.

The near symmetry felt sibling-like, same-same but different. Morris looked less Vogue, more Broadway, with his boxer’s build clad in a sweater, khakis, and a flat-billed hat that Wortham was making fun of. The contrast between chic and earnest extends to other aspects of their chemistry. “One of the funny dynamics” of the duo, says Samantha Henig, who heads the podcast division at the Times, “is that Jenna is so of the internet and Wesley is really not. But he’s also unbelievably plugged in,” she adds, “so I don’t know how he does that.”

They’d come for their weekly appointment at Pineapple Street Media, a dynamic young podcast agency that boasts clients like Hillary Clinton and Lena Dunham, who calls PSM founders Max Linsky and Jenna Weiss-Berman the “funniest, smartest people in Brooklyn.” On the Monday in question, Weiss-Berman was in New Orleans on a project but would return to edit the audio. She’s said to have an artist’s touch; “film editor meets poet meets DJ,” in Dunham’s words. Linsky plays director: He leaned in a chair and threw out notes — “I’d really like to hear you guys on why it’s so hard to talk about Shyamalan, because you have to give away the ending” — and made fun of the hat, which would cameo in the week’s installment of their podcast, Still Processing.

“So, I’m Fat Albert,” Morris says, after Wortham launches with an impression, to which she responds, “You are wearing a newsboy cap.” Morris counters that “we live in a world where the opposite of what is true can be true. I am a living alternative fact.” Wortham: “That hat is an alternative fact.”

Few mediums are more personal than the podcast. Audio — accessible anywhere, recordable anywhere — suggests the thrill of anonymous phone sex, the purity of lifelong pen pal–dom. Earbuds in, listeners can shut out the external cacophony of the modern world, seduced by a voice traveling through those thin white tendrils. “What’s more intimate than being whispered to?” as Dunham says, on the allure of the form. In the debut episode of Clinton’s podcast with Linsky, which aired November 6, she hints at vulnerability when she says, “Contrary to some opinion, I do have feelings. I can get hurt.” Linsky, who told me he loved her more with every meeting, and was set to continue with the podcast from the White House, deadpans: “I think we just broke news here.”

Hence the allure. And yet most of the top podcasts on iTunes are led by white male hosts. Homogeneity spreads; people take cues. For a generation raised on a monolithic radio culture, the temptation to mimic can be strong. Robert Boynton, an NYU professor focused on audio journalism, draws a through line across media. “In the Seventies and Eighties, every newscaster had a certain kind of sound. Then there was a period when everyone was trying to sound like Ira Glass. It’s amazing how many guys are out there — nerdy Jewish guys with nasal voices — and they all sound like him. Including the guy from Gimlet, who even says, ‘I’m the guy who’s confused for Ira Glass.’ ”

Monoculturalism in podcasting reflects the “built-in advantages and disadvantages of the existing world,” says Shaun Lau, a Chinese-Japanese-American podcast host who has sought to raise awareness of homogeneity in the industry. Podcasting could theoretically raise up outsiders, but its economics are tricky: low barriers to entry, but high standards for success. To sell advertising, a show must be popular (and thus findable), featured on the iTunes homepage, or given press. Hosts with built-in fan bases, or backing, tend to triumph in this sphere. “It’s not that listeners necessarily prefer [white male hosts], but they gravitate toward them,” Lau says, “because there’s money and resources behind established traditional media.”

Still Processing — and Wortham, and Morris — twists the rules. A product of one of the most established media properties in the world, it stars two people who differ from the podcasting mainstream in obvious ways: They are both black, and they both identify publicly as queer. The show was inspired by Another Round, the BuzzFeed interview series hosted by Tracy Clayton and Heben Nigatu (and produced by Weiss-Berman, who was formerly at BuzzFeed), but the goal was never “to make a show about being black in America,” says the Times‘ Henig, who was instrumental in launching Still Processing and signing on Pineapple. (Clayton and Nigatu are also black.) The point is the “passions of Wesley and Jenna,” Henig says. This has something to do with “the fact that they’re young and that they’re people of color. But also, they’re so cool. It’s basically inevitable that — if you have a conversation with one of them — it is the most insightful conversation you have that day. We’ve been lucky enough to experience that in the office, but we wanted to broaden the audience.”

The hosts speak with casual authority on vital topics, as any critic might aspire to (though many can’t). But their scope is as varied as their work, their chemistry as electric as any great duo’s. Morris is a wonk and a populist, able to “look at the world from an airplane but also a microscope,” as Wortham puts it. Her writing is finer-boned, crafted with referential architectures strong enough for the far reaches of Twitter. Linsky reminds them not to forget their “veggies” — their written work — but otherwise they have no directives. Some segments could double around a dining table in a black home, such as a recent one on saying bye to Obama (the “ultimate black dad”) or another on Kanye’s erraticism. Meanwhile, the hat episode seems built for an Indian uncle: swerving from a Wortham-essay-pegged breakdown of the creepiness of Amazon’s Alexa to the legacy of M. Night Shyamalan, defended by Morris — against his co-host’s protestations — as a fun “paranoid moralist.”

Increasingly in today’s world, one wonders what is universal and who is central. Wortham, an alum of wired.com, skirts the edges of tech, culture, and identity in her writing — carving out her own corner of the internet wherein she is a rightful star. (A shimmering Lemonade essay prompted a thank-you note from the Queen herself, signed “Love, Beyoncé” and ‘grammed by Wortham.) Morris was forged in that other crucible: the print world. After winning a Pulitzer for his film criticism at the Boston Globe, he moved on to pen dense, sardonic crit for Grantland. Linsky points to Morris’s essay on Hollywood’s treatment of the black penis — dropped by the Times with the surprise factor and gotta-have-it feel of an album release — as an example of his uniqueness in media. Morris worked on the essay for months; Linsky recalls congratulating him on his viral success the day it was published. “[Morris] said, ‘Oh, did people like it?’ ” Linsky remembers. “He hadn’t looked at his Twitter, his Facebook, his email.” Weiss-Berman agrees. “He’s so mentally healthy,” she says, sounding awestruck.

Wortham calls him “focused.” Meanwhile, Morris says he’s learning from Wortham how to live online; only recently has he had the urge, after snapping a picture, to share it on Instagram. Since the podcast’s launch, the two have become constantly connected, when not in person, through machines. “She’s an elemental part of my life,” Morris says. “I talk to Wesley before I go to bed,” Wortham echoes. “And when I wake up I email him.” Morris partly puts down their canny performance skills to a lifetime of code-switching. “Any person who has learned to be fluent socially in different environments — racially, sexually, whatever — you learn how to be a version of yourself depending on context.”

There’s an argument to be made that the nature of a critic’s existence matters, that in a field that maps vision and empathy, the old view of authority turns illogical. The latest episode of Still Processing holds a gem of a segment suggestive of this idea. The subject is tired enough: Dunham’s own Girls, the final season of which debuted last Sunday. To Morris’s broad insights (Marnie is a drag, Zosia Mamet a genius), Wortham — who wrote the definitive critique of the show’s psychic narrowness years ago — drills to the core of the Girls hot-take industry, using her life to explain larger shifts. “If you are a black woman like I am, you deal with these women the moment you wake up to the moment you go to bed,” she says, evoking clueless girls flicking their wet hair on her face on the train. She cites Insecure, Atlanta, and Broad City as palliatives. In the past, “spending my leisure time with these women was not something I wanted to do.” Today, watching the credits roll the names of twenty-year-old women, Wortham has reconsidered: “My cold heart beats with pride.”

Still Processing, like most shows in the Pineapple Street stable, is de facto progressive. If the agency has an ethos, it might be locational. Clinton and Dunham respectively claim headquarters and a home mere blocks from the studio. And it was in the borough that Morris and Wortham were first introduced, by the New York magazine writer Rembert Browne, at an anniversary party for the Awl. (There is something of the young media nerd’s fever dream to the entire operation.) It was prickly love at first sight. “We both were excited and intimidated by each other,” Wortham says. “Like, we wanted to talk to each other more, but we’re both like, ‘Oh no. That person’s too cool for me.’ ” Morris was blunter: “I thought you didn’t like me. Or just that you had better things to do.”

Pineapple operates without v.c. money, a rarity in podcasting. Revenue relies on a Draper-esque hustle for clients, and advertisers, that’s demanded by a market lacking a clear competitive structure. (Theoretically, for podcast production, “all you need is a computer, or even a phone,” Weiss-Berman says.) Agencies tend to favor either a “churn” approach (as seen in the stark and effective fare of Panoply Media, the Slate-affiliated studio that produces podcasts for Condé Nast, the Wall Street Journal, MTV, New York magazine, Rolling Stone, and other old media heavyweights), or lush standardization à la public radio (think Gimlet Media, with a roster of shows as linked-yet-distinct as an haute couture collection). Pineapple is more ad hoc. Self-funding allows freedom, with limits. Branded content supports pro bono work and designer shows like Dunham’s Women of the Hour — which Weiss-Berman launched at BuzzFeed, its first home. Linsky wouldn’t give specifics, but hinted at big projects in
the new year.

A co-founder of the journalism site — now also a podcast — Longform, Linsky once wrote wild features for a Florida alt-weekly, assigned in a haze at the end of the last decade, as the print world collapsed. Weiss-Berman found her way to audio through the nonprofit StoryCorps, where she interned while working in the collections department at a big law firm (“the guy who took my job after me got indicted,” she notes wryly), and started side-hustling. She still edits for Longform, and did through her tenure at BuzzFeed, where she headed audio. Henig, the Times staffer who tapped her for Still Processing, knew her via Longform; Henig is married to Evan Ratliff, a fellow co-founder. She hoped to channel Another Round, and figured Weiss-Berman could help the Times, then a podcasting novice, do so.

The timing — coinciding with Dunham’s desire to strike out on her own — struck Linsky as meaningful. Combined, he and Weiss-Berman share an enviable contact list. “Why shouldn’t we start our own thing right now?” he recalls asking her soon after the Times‘ request. Within weeks, Weiss-Berman had quit and set up a new shop with Linsky, eventually hiring a handful of assistant producers and paid interns and shifting to DUMBO. The office is cozy and spare, with rugs, pineapple-themed décor, a photo of Larry Bird (in honor of Linsky’s Boston roots), and scattered knickknacks donated by Elisabeth Watson, a production assistant on Girls who helps with Dunham’s podcast.

Neither founder came to podcasting with a grand vision, and they say Pineapple’s strategy is equally organic, a matter of placing one foot after the other on a path that feels right. “I think Max correctly has realized that a lot of what any of these enterprises — doing an independent website, or podcast — involves is a kind of ‘going for it’ [mentality],” says Aaron Lammer, another Longform co-founder. “There’s not really a procedure or standards. It’s making things up as you go along. Neither [Weiss-Berman nor Linsky] had to go to podcasting business school.”

In person, the partners project inverse energies of what you might expect. Linsky is intense, whereas Weiss-Berman — the one everyone says knows everyone — seems almost shy. In press, she is spoken of reverently, including and especially by Linsky. (One article refers to her as “the Jenna Weiss-Berman.”) “No one else works like her,” says Dunham, who first met Weiss-Berman at Oberlin when a roommate dated her. The luster of her rep seemed a surprise to Weiss-Berman when I mentioned it, so much so that once Linsky left the room to take a call, she gently asked for details. Like the stars of Still Processing, Linsky and Weiss-Berman were dressed evocatively, if less glamorously. Linsky wore the neutral baseball-hat-and-jeans uniform of “the rube,” as he called himself, explaining his role as the audience stand-in, nudging Morris and Wortham into lines of conversation that might serve listeners perhaps less savvy than they. Weiss-Berman wore a sweatshirt she’d bought online. Like her, it was insidery, playful, and low-key, printed with that unmistakable credit: EXECUTIVE PRODUCER DICK WOLF.

Weiss-Berman admits to an undying love for her roots, but says she’s sensitive to the implications of public radio, particularly of “the white voice.” Speaking naturally and forcefully is something she and Linsky are keen to encourage hosts to do (they laugh that Morris and Wortham are naturals, Morris at times maybe too exuberant).

Still Processing seems cast from a different mold than public radio journalism: that of the buddy comedy, perhaps — or, to step into a genre of the home — of a phone call between brilliant friends. “We’re not looking to be a billion-dollar podcasting company,” Weiss-Berman says. Nor is the point to remake NPR for millennials, exactly, though the closest Pineapple Street has to a mission statement sounds primed for a fundraising callout: “Just good people,” Weiss-Berman says, “and good work.”