The Weird, Fun Outlet Won’t Always Pay You

Willy Blackmore ponders how The Stopgap, a new blog, is rethinking the refrain of “pay your writers.”

In 2015, Jo Livingstone was still getting their footing in media. While working an internship at Slate, they were freelancing on the side too, writing when and where they could. Livingstone had an idea for a story about rain and pitched it to Matt Buchanan, who was at the time co-editor of The Awl. He suggested they do it as a listicle, which Livingstone ran with, writing a beautiful consideration of the various types of rain they had encountered throughout their life, from Brooklyn to London to Namibia. 

“I had no idea where it came from, it was like a late-night fuzzy thought,” Livingstone told me about the initial impetus for the piece. But it clicked with readers, and ultimately ended up being recommended by a guest on the same Slate podcast that Livingstone was working on in their internship. 

At that moment, Livingstone felt like they bypassed their internship completely. Back then, Livingstone had never made more than $50 from a piece of writing, and did plenty that didn’t pay at all; two years later, they started working full-time as the book critic at The New Republic.

This kind of thing used to be not all that uncommon in digital media: a young writer comes out with a kinda weird, kinda fun story in a smaller, but well-read publication, gets read by the right people, and the author sort of goes pop. There were podcast invitations, assignments from other publications, even jobs, eventually. But as the industry has contracted and is now outright imploding, a lot of those weird, fun outlets that were once the breeding ground for a generation (give or take) of writers have disappeared: The Awl, The Toast, The Hairpin, Gawker, The Outline, and others have all closed. And that’s left fewer outlets that are in part geared toward being a place to get your start, or to just publish something odd and interesting that falls outside the churn-and-burn of the news cycle, and might not be able to find a home anywhere else. 

Livingstone’s latest project, co-founded with the writer Daniel Lavery (who was also a part of the beloved blog The Toast), aims to change that at least a bit: it’s a blog in the purest sense called The Stopgap, which bills itself as “better than nothing.” The site thus far is very eclectic — recent posts include “Songs, Movies, Etc. That Are Actually About Butch Flight” and “Questions and Answers in Practical Seamanship” — and features many more bitsy-type stories that were a mainstay of the blogs of yore, like lists, as well as the occasional longer essay by a guest author. There is also essentially no money involved beyond a monthly web hosting fee: no ads, no salaries, no traditional payment to anyone who writes a guest post. Rather, The Stopgap uses a tip jar model that makes it possible for readers to pay a small amount directly to the writer of a piece via PayPal. The Stopgap isn’t a business endeavor that’s trying to upend or innovate or disrupt or do any other kind of jazz-hands techspeak; it’s not really a business at all. Rather, it’s a purely creative enterprise through and through. 

“We were both struck by how comparatively empty the internet seems now compared to five or ten years ago,” Lavery wrote in an email. Lavery and Livingstone worked together to fill this void. And by deliberately doing so without any real money, as a blog rather than a business, The Stopgap offers an opportunity to reassess one of the leading truisms in digital media: never write solely for free.

Both Livingstone and Lavery did their fair share of writing without pay, or close to it. “If I remember right, I think all of my writing for The Hairpin and The Awl was for free, which paid off enormously,” Lavery said.It led to paid writing gigs, an agent and later a first book deal, and connected him with Nicole Cliffe, who Lavery started The Toast with in 2013. (Lavery also turned down plenty of unpaid work.) 

But as digital media grew up, and venture capital money started flowing into Vox properties, Vice, BuzzFeed News, and elsewhere, getting paid became not only the standard, but the rates improved too. And once there was a $1/word out there somewhere, more and more writers started putting their foot down: no more writing for exposure only. 

It’s a notion that was repeated many times last week, after a story about Byline, a new site from the co-founder of Drunken Canal, ran in the New York Times Style section. The story reported, in close proximity to a line about Gutes Guterman wearing Gucci slides, “For now, contributors to Byline will be unpaid.” 

It goes without saying that labor should be paid for, and paid fairly. But in hindsight it seems that something has been lost between the early 2010s and now, as both the desire and opportunities to write a weird thing have disappeared. Until the media industry, indie or not, can provide those opportunities again, and pay for them, The Stopgap wants to be a stopgap — not a solution, per se, or an enterprise sponsored by Co-Star and Feeld (as Byline aspires to be), but better than nothing.

Livingstone recalled how when they first moved to New York in 2010 and began dabbling in writing outside of their medieval studies PhD program, “there was zero gatekeeping, zero professionalism, zero money.” Certainly not everyone who was writing during that time experienced the kind of viral success that Livingstone did with their rain story (as I can personally attest), but the feeling that it could happen was much more visceral than it seems to be today. With social media ascendant (rather than crumbling), it was almost a daily occurrence that one story would take off, and while that sometimes happened for all of the wrong reasons, when Twitter latched on to good, inventive writing it was often career-making. Stories still can and do go viral, though not as routinely. But it’s the infrastructure of publications and social media that have changed — not writers and readers, who still have their strange passions and the desire to read about them, respectively.

“I think if you’re going to ask people for their work and not pay them it has to be for a really good reason,” Livingstone said. For The Stopgap, that reason is the tip jar, which, if successful, really could present a new way to think about writing and money on the internet.

But even the tip jar has some journalists upset — and they’re posting about it, for free, on Twitter.

INSIDE BUSINESS OUTSIDER

The Insider Union is writing its own news with its new strike publication, Business Outsider. According to the site, the “publication will be shut down at the resolution of the labor disputes.”

So far, a lot of the Business Outsider articles emulate the style and content of Insider pieces: all articles have TLDR bullet points, for one. The outlet has published an SEO friendly listicle of pets supporting the strike, an exclusive story from the White House, and a first person account from a media worker’s initial experience at the picket line. 

“It’s a great opportunity to be able to do the things that we as reporters and editors are really good at already, and being able to flex those muscles even while out on strike,” Palmer Haasch, an entertainment reporter at Insider, told Study Hall. For Business Outsider, she wrote a poignant essay about paying homage to Kendall Roy at Battery Park following a day of picketing in front of One Liberty Plaza. Haasch says that editing and writing Outsider content has helped her connect with people who she may not typically work with at Insider. 

Business Outsider isn’t the first of its kind. The Pittsburgh Post-Gazette Union, which has been on strike since October 18, launched Pittsburgh Union Progress to cover both strike updates and community and sports news. Haasch said that Business Outsider was inspired by other striking publications like the Detroit Sunday Journal, a newspaper run by striking journalists at the Detroit News and Detroit Free Press in the mid-1990s. 

Hopefully, Outsider’s tongue-in-cheek homage to Insider’s signature style helps casual readers understand a crucial point: it’s the writers, not the management, who are the heart of all content. And for the love of God, don’t click on an Insider link. —Daniel Spielberger 

COMINGS AND GOINGS

—Anna Medaris, a health and lifestyle reporter, is leaving Insider.
—Charles Forelle was promoted to deputy editor in chief of the Wall Street Journal.
—Lindsey Choo joined The Wall Street Journal’s tech team in their San Francisco bureau.
—Wolfgang Ruth, who was previously Vulture’s social media manager, started a new role as social lead at Apple News.
—Fred Ryan, the chief executive at The Washington Post, is leaving the newspaper on August 1, and will lead the Reagan Institute’s Center on Public Civility (allegedly its nonpartisan). Jeff Bezos, the Post’s daddy, named Patty Stonesifer, a former Microsoft executive, as interim CEO.
—Queenie Wong is now a state politics reporter covering tech and entertainment policy at the Los Angeles Times.
—Matt Karolian and Michelle Micone are joining the Boston Globe to lead AI strategy, product, and content.
—Katie Fehrenbacher is joining Axios as a co-author of the Axios Pro newsletter on climate tech deals.

EVERYTHING ELSE

—On Monday, the New York Times laid off 20 reporters from The Athletic, a subscription sports website owned by The Gray Lady. Former beat writers of the sports pub were also moved into more general assignment roles.
—Last week, the Forbes Union said management “abruptly” canceled a bargaining meeting in a “last-minute email” after they asked the company to “provide a remote attendance option for an upcoming in-person session.” On Monday, the Forbes Union picketed in front of the Forbes Iconoclast Summit in New York City.
—Morning Consultant dissolved its newsroom, laying off seven journalists. An additional eight journalists transitioned to working on the analyst team.
—According to Reuters, Axel-Springer, the German media conglomerate which owns Politico and Insider, is starting a mergers-and-acquisition team dedicated to firms working with AI.