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Aug. 31, 2020, 9:03 a.m.
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Study Hall, the gossipy media site for freelancers, sees Gawker as its editorial north star

“We feel like we have to create the future of media, as we advocate for the people who work in it.”

Study Hall doesn’t want to be Nieman Lab, nor does it have any interest in aping Mediaite, Digiday, or the Columbia Journalism Review. No offense should be taken by any of those publications — they do good work and serve their readers well — but Study Hall aspires to a niche that no Ivy League-backed nonprofit or VC-funded startup could ever hope to appease. Instead, the company wants to speak to journalists in the same way that they schmooze at happy hour.

Study Hall co-founders P.E. Moskowitz and Kyle Chayka are career freelance writers, and managing editor Erin Schwartz is a recent Vice refugee. Together, they have years of experience battling media’s institutional deterioration, and they are fluent in the Twitter-addled network of names, references, and jargon that gives the freelance subculture its life. Study Hall was first established as a Patreon-funded newsletter and listserv to keep freelancers informed on the scuttlebutt around the industry, but last month, the company launched its own website, officially giving the staff a permanent editorial outpost. The hope is that media gossip can be interesting enough to support a self-sustaining business. If Gawker was pitched as an antidote for bored office yuppies, as one staffer puts it, Study Hall can do the same for precarious gig workers.

“We’re more irreverent, and more bloggy. As an editor, it’s a lot simpler to make content primarily for 4,000 people who talk to us all the time, versus attempting to hit crazy growth targets,” adds Schwartz, who was hired in 2019 and is the company’s only full-time employee. “We’re trying to make things that reflect and refine the sensibility that is already there in the community. Sometimes that means a report on racism in the travel industry, and sometimes it means a really dumb joke.”

A full subscription to Study Hall, at $11 per month (lower-priced options, with less access, start at $1 per month), will net you the following perks: The weekly email digest, which recounts the latest news, trends, and disasters in the media writ large. An “Opportunities” newsletter, which signal-boosts different employment openings, contract jobs, and freelance calls for pitches around the industry. Membership to the listserv and Slack channel, where colleagues congregate every day to workshop feature ideas, plug their best work, or, sometimes, just vent about problem editors and delayed payments. And, of course, access to the website and its archive of essays and investigations that are tuned, specifically, to the beleaguered freelance class.

It is on that homepage where Study Hall’s praxis is most apparent; the coverage ranges from the gleefully frivolous to the comprehensively astute. Recently, the site published a wide-ranging profile on New York Times style section czar Choire Sicha, and last year, I wrote an essay for the newsletter about, essentially, the importance of wearing shoes when working from home. Study Hall makes a real effort to serve a wide-ranging suite of journalists — it promotes job postings from all over the world, and offers a subsidized $1/month membership for media workers of color — but from my own anecdotal experience as a subscriber, the service has a distinctly millennial, New York bent. Case in point: Nearly everyone I interviewed for this story mentioned the golden days of Gawker as their editorial true north.

About 4,500 people currently pay for a subscription. That is a reassuring number; it proves that the staff isn’t crazy to believe that there is a genuine, commercial thirst for a heavily insulated media-focused vertical. There is an understanding among the Study Hall staff that the bulk of its published stories would never be able to find a home at any other publication. That itself is a sign that they’re onto something special. But outside of those vectors, Study Hall also represents a protest against the overwhelming grimness coursing through the rest of the media community. The Covid crisis has revealed a looming truth about the news business: ad-driven revenue models simply do not work. Every day, those within the circuit wake up to more headlines about frozen freelance budgets and a rising tide of layoffs at relatively sturdy fixtures like Vox and Buzzfeed. That puts Study Hall in an interesting position: It aims to speak for all those weathering the current storm, but as an ad-free, worker-owned, subscription-based publication, it also hopes to set a precedent and serve as a model for others who want to rebuild the industry.

“The mission was to experiment with different forms of writing, content, and revenue models. That’s the dual purpose. We are here to serve media workers, but it would be irresponsible to do that while the rest of the industry collapses. What would be the point of a newsletter if there was nowhere to write for?” Moskowitz says. “We feel like we have to create the future of media, as we advocate for the people who work in it.”

Nowhere is that attitude more apparent than on the Study Hall listserv. Freelance writing is alienating work, which is what makes the forum such a revelatory social experience. Here, the isolated dialogues I carry on with myself — my paranoia about the dwindling funds in a certain publication’s contract canopy or whatever — finally find a reciprocating force. The discussions on the listserv are helpful on a purely utilitarian level; frequent topics include pay rates, editorial contacts, and pitch etiquette. But more spiritually, the listserv is a gossipy, ad hoc grapevine for a community that’s never really had one.

“Over the first few months we hit 300, 500 subscribers, and when you have enough of this crowd of people in the same place, it becomes a barometer,” Chayka says. “It’s more private. It’s not just a free-for-all. I think providing that alternative space for discussion helped it grow.”

That’s the paradox facing Study Hall down the line. Is it possible to be a professionalized editorial brand while also maintaining status as the premier, off-the-cuff backchannel for the media underworld? Anna Maltby, executive editor at Medium’s health and wellness publication Elemental, told me that a few months ago, she was informed that a writer had alleged on the Study Hall listserv that she’d stolen their pitch and assigned it to a different freelancer. “I was so alarmed to hear that, because that’s not something I would ever do, and clearly this person was hurting,” Maltby says.

Maltby says she reached out to that freelancer to talk things out over the phone. They had a productive conversation, which led to a new assignment for the writer, and the two are still working together to this day. Maltby is a former freelancer herself, and says she is absolutely in favor of the notes-sharing and solidarity that occurs in a place like Study Hall, but she also hopes that its denizens “take [the] posts with a grain of salt.”

“What they’re reading is, of course, only one side of the story. And if you have a question or concern about your work or interactions with an editor, it’s worth trying to sort it out one on one first before turning to a larger network for help,” continues Maltby. “When all our interactions are digital, it can be hard for both writers and editors to remember that there’s a person on the other end of the line. Ultimately, though, I’m glad these networks exist, even if it would be nice for them to be a bit more regulated.”

The Study Hall team understands her perspective. The staff consists of only seven people, just one of whom — community lead Evan Kleekamp — focuses primarily on moderation. All of the staff members, though, have been thrust into leadership roles for a collective of journalists who’ve been promised plausible deniability on the listserv. That’s only going to get tougher as more people sign up for the service. “Study Hall has done this weird thing where we’ve formalized this backchannel, and people know it’s a backchannel. Before, it might just be a Slack full of ex-Gawker people,” explains Chayka. “The thing about the listserv is that, yes, it’s private, but sometimes stuff gets out and it’s uncontrollable.”

Chaykra reminded me that leaking anything posted on the listserv is a violation of policy. If they knew who tipped off Maltby about the thread about her, the leaker would be banned. Study Hall puts freelancers first, but with a fresh new website and exponential growth, will it be able to maintain the after-hours environment that drew people to the company in the first place?

Scandalizing an editor with a few friends in an email chain is one thing. Doing it for a gathering of thousands is quite another. Can Study Hall strike the right balance? Its subscribers certainly hope so. The gossip must thrive, by any means necessary.

Luke Winkie is a journalist and former pizza maker based in New York City. In addition to Nieman Lab, he’s contributed to The New York Times, The Washington Post, and The Atlantic.

High school notes courtesy of Laura Hazard Owen.

POSTED     Aug. 31, 2020, 9:03 a.m.
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