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Oct. 11, 2018, 10:45 a.m.
Business Models

The Outline built itself on being “weird.” But is it weird enough to survive?

“We’re not the enemy. This is a really shitty industry for writers.”

There are some sites that everyone roots for. Scrappy, beloved. See: The Awl. The Toast. Or not so scrappy, but beloved still. See: Grantland. When they shut down, people mourn them.

Then there’s The Outline.

In April 2016, Joshua Topolsky wrote a Medium post entitled “Your media business will not be saved.” Topolsky, the cofounder of The Verge, had left his position as Bloomberg’s top digital editor several months before.

“Your problem,” he told his fellow media people, “is that you make shit”:

A lot of shit. Cheap shit. And no one cares about you or your cheap shit. And an increasingly aware, connected, and mutable audience is onto your cheap shit. They don’t want your cheap shit. They want the good shit. And they will go to find it somewhere. Hell, they’ll even pay for it.

The truth is that the best and most important things the media (let’s say specifically the news media) has ever made were not made to reach the most people — they were made to reach the right people.

At the time of writing the Medium post, Topolsky was in the process of raising money for his own media company, The Outline, which launched at the end of the year as a “weird new adventure.” (The word “weird” appears five times in the announcement.) “No games, just something fucking interesting,” Topolsky wrote. One of its investors, RRE Ventures, called it, without any apparent irony, “the first new media company ever.”

Nearly two years later, The Outline is half the size it was at launch. It’s the subject of freelancer boycotts and subtweets. It took venture capital and then it laid people off, not once but twice.

It is still, however, doing what Topolsky said it would do at the beginning: publishing articles that fit loosely into the themes of “power” (“The million-dollar brownstone that no one owned,” “French girl fashion is…how do you say…le bullshit), “culture” (“My dad painted the iconic cover for Jethro Tull’s ‘Aqualung,’ and it’s haunted him ever since,” “The unbearable wrongness of Gwyneth Paltrow“), and “the future” (“I had a mastectomy to lessen my risk of breast cancer. Does new science say that was a mistake?”, “Better birth control options already exist, but we’re not allowed to have them.”)

So what happened to The Outline? Did it try to make the good shit and stumble by mistake into cheap shit? Did it overestimate how unique its editorial voice actually was? Or has it faced the same set of roadblocks the rest of the digital media industry has, only without much goodwill from all those cheap-shit producers?

“We’re not the enemy. This is a really shitty industry for writers,” Topolsky told me. “We should make it better, and we have been trying really hard to make it better here.” The Outline’s traffic has doubled year over year, he said, with upticks in returning visitors, time spent on site, and overall pageviews.

He acknowledges that the company “got over its skis” (starting out with ambitious video efforts that had to be scaled back, that team laid off), that it tried to do too much too fast. His goal for The Outline is still that it be break-even, sustainable, and advertising-supported.

“No one here is like, ‘Oh my God, guys, we’re gonna be billionaires,'” he told me. “The investors aren’t like, ‘Oh my god, you guys are gonna be billionaires.’ It’s very realistic. What would it be like to be in a business where the CEO is the editor-in-chief, and we’re not looking over our shoulders at some weird demand from somebody who doesn’t know how this stuff gets made? What would it be like to have a sustainable business where you tell stories that you really care about, and you don’t feel those enormous market pressures? How do we make another kind of business in an era of media that is, for lack of a better way to say it, completely fucked up?”

The Outline now has 16 full-time employees, down from 30 at launch. The most recent round of layoffs included the site’s only two remaining staff writers, and it was this fact in particular that led Study Hall (a sort of digital collective/support network/listserv for “media workers,” most of whom are freelancers, now with 1,100 paying members) to issue this statement announcing a boycott of The Outline. It was signed by 115 (unnamed) Study Hall members. From that letter:

When venture capitalists, which media companies increasingly rely on to survive, demand profit, it is staff writers and freelancers who pay the price. There would be no Outline (or any publication) without the labor of the editorial staff who shape it, and it’s disheartening to see management dismiss/toss aside their employees so blatantly.

This is why several dozen members of the media worker collective Study Hall will no longer write for The Outline until there are significant changes made at the company.

We are not happy to do this. Many of us have contributed to the site, which has a unique voice and, unlike many publications, pays both decently and promptly, rarities in this industry. But we cannot allow Josh Topolsky and his investors to rely on our loyalty to The Outline’s vision when they choose to devalue writers’ work and treat our ability to survive as externalities. The Outline started with a focus on power, culture, and the future; they’ve since created a workplace culture that doesn’t seem to value the labor that makes the site function, have fallen back on typical power structures, and are building a future we want no part of.

Since that letter was released on September 5, members of The Binders, the women’s/gender-non-conforming writing community, have launched a boycott of their own. Some freelancers who had pieces accepted by and in the editing process with The Outline pulled them. Neither of the petitions — Study Hall’s or The Binders’ — made specific demands of The Outline; they didn’t explain what, precisely, needed to change for the boycott to end.

“We increasingly feel completely disposable and financially insecure as freelancers,” Enav Emmanuel Moskowitz, a cofounder of Study Hall, told me (acknowledging also that they had been “a big fan of” The Outline.) “It’s one thing if one publication is struggling, but for essentially every publication to switch editorial strategy every month — pivoting to and back from video, longform, essays — it’s becoming harder and harder to make a living in our industry as a freelancer, and harder to know what’s going on.”

Topolsky told me his “understanding — my read of the letter — is that there’s a wave in the industry of people who are replacing full-time people with freelance people, because of the need to trim back budgets. For us, that’s not what we’re doing. We’re not interested in replacing full-timers with part-time workers…We’re doing what we’ve been doing, but we won’t have the added asset of staff writers for the short term. We see this as a short-term change, not a permanent position for The Outline or any business that we’re interested in building.

“The Outline, as a business, has always relied on freelancers for the majority of our work,” he added.

“I’ve written for The Outline once before and I really enjoyed the experience,” Zachary Siegel, a freelance writer who covers public health and criminal justice and has written for publications like The New York Times Magazine, New York Magazine, and Slate, told me in an email. “The editor was attentive, I was paid well and on time. But signing on to Study Hall’s letter felt like an important demonstration of solidarity, more important than a paycheck. Media companies are increasingly run like tech startups, with big valuations and multi-million dollar funding rounds. It’s not just The Outline. These companies rely on our words to fill their pages, generate traffic, and build loyalty among readers. Yet in the eyes of shareholders, hedge funds, and venture capital, we’re expendable. I wanted to take a stand against these dark trends.”

But it’s really not just The Outline. Much larger digital media companies — Vox, BuzzFeed, Vice — have also all taken venture capital and also all had big layoffs (most recently, BuzzFeed’s podcast team). Why not boycott them? I wondered if The Outline felt like an easier target. It was small, so it would suffer more from a boycott than a large company would. Boycotting it might also feel like a safer bet for a freelancer than boycotting a big outlet like BuzzFeed, which seems more guaranteed to stick around in some form or another for the next few years.

Are the kinds of people who read Outline stories really some kind of special demographic? Or are they just thirtysomething news consumers? Before Topolsky launched the site, he told Ken Doctor about the kind of reader The Outline would try to reach:

They live in urban areas. They’re really tech-savvy. They fund Kickstarter projects. They eat farm-to-table food. They care about politics, they’re engaged…The data is really starting to show that there are a lot of people who self-identify as smarter and savvier and less susceptible to bullshit, and are hungry for a story every day, or multiple stories every day, that talk about their world. The world that is important and valuable to them, in a way that serves their intelligence and doesn’t talk down to them. It’s not condescending. It doesn’t dumb things down. It isn’t trying to play for every possible person who might read a story.

Topolsky told Recode earlier this year that “what we’re doing is insane — what we’re doing is not normal, for sure.”

I’m not sure what, exactly, The Outline is doing that is so weird. It wouldn’t be surprising to find any of these articles in any number of places on the web. It is maybe a little unusual to have this sort of motley highbrow-general-interest content be the focus of the site, rather than being a kind of side event with politics and tech news taking the main stage. My sense was also that there is an unusually large amount of women’s health coverage for a site that is not explicitly aimed at women.

I am in The Outline’s demographic, which can basically be summed up as “youngish coastal elites.” And while The Outline’s pitch from the beginning has been that there isn’t enough content for us, it actually seems as if there’s content for us everywhere, too much to ever possibly read all of. Does there need to be a special site aimed at us when pretty much every site — Slate, The New Yorker, The New York Times, The New York Times Magazine, The Washington Post, Mother Jones, The Atlantic, huge sections of Twitter — is aimed at us? The number of people, in 2018, who want farm-to-table food, who think they’re not susceptible to bullshit, don’t want to be talked down to, is huge — and content for this group is everywhere.

Okay, so let’s talk about the venture capital. Even two years ago when The Outline launched, this seemed a little remarkable, a little mockable: Venture capital going to a white dude’s splashy new media company, what a shocker. WWD was at the goofy-sounding, pre-crash-vibe launch party:

Instead of trays, the hors d’oeuvres were nestled on boughs of birch or inserted vertically into holes in white plastic walls so large they required two servers to carry them through the crowd. Soft pretzels dangled from the spokes of an open umbrella ready for guests to pick them.


A post shared by nicole yoko (@nicoley_d) on

The Outline has raised a total of about $10 million in venture funding — $5 million at launch, and another $5 million in a round that closed in May 2018, although the money for that had actually come in October 2017. The reason for the delay in closing the round was that The Outline was in talks about acquiring or merging with another property (reportedly The Observer). That deal didn’t work out. By the time the round officially closed, money that had come in months before was already well in the process of being spent. In Topolsky’s view, he didn’t squander the money, but he was, perhaps, overly ambitious about what The Outline could be at launch.

“I know a lot of people out there talk shit about investors,” Topolsky said. “VC-backed companies, particularly in media, have been a real mess. I think that we happen to have some investors who are truly committed to making something better…Probably one of my mistakes was that I hired a lot of people really fast before we knew exactly what the shape of the business was going to be.” One area where he “got over his skis,” he said, was video.

“We were like: We’re gonna build a new content creation platform, a new ad platform, we’re gonna do this crazy design, we’re gonna put together a brand-new editorial team, we’re going to do video, we’re going to do audio, we’re going to do interactives. In the first year, we had an amazing video team, people I’d worked with when I was at Vox [Media], who I loved. We were doing really good, interesting video. But as we were getting into planning for Year 2…we just felt like, from a focus and budget perspective, we were doing too much.”

“I don’t think the money was misspent,” said Erik Hinton, who was a senior developer at The Outline before he was laid off in early September, and who’s previously worked at The New York Times and The Wall Street Journal, among other places; he recently started at Medium. “They paid high salaries to their developers and their designers. They paid high salaries to their ad team and sales team. They paid good freelance rates. Those things just add up.” Nobody’s eating soft pretzels off umbrella spokes on the reg.

“One of the reasons we’re tightening our belts right now is because we want to speed toward that break-even point,” Topolsky said. “It would really prove something about this type of business. If we can get to break-even with the kind of business we’re running, it’s a really powerful signal. It’s something that few in media, and certainly none in media with the kind of model we have, have done in a very long time.”

Elias Rothblatt, the company’s COO, stressed that break-even for The Outline is based on advertising revenue. “The venture funding was so we could build these numerous pieces really quickly and amp up a new brand,” he said. “But when we talk about getting to a point of break-even or profitability, that’s all based on advertising revenue. That’s not to say we don’t consider other exciting revenue models that are down the road, but right now we’re really focused on advertising and we think we’ve got our best shot there.”

Topolsky compares The Outline’s advertising to the advertising you’d see in a glossy magazine. This is always what everyone says about their digital advertising when it’s the focus of their revenue model. (Also, print magazines are really not doing well.) Maybe a better way to describe it is what you used to see in a glossy magazine. “The model for us is much more like magazine advertising in its heyday,” Topolsky said.

Last year, for instance, The Outline did an ad campaign with Macallan, the expensive scotch. “There’s not that many people in the world who ultimately would think about buying a bottle of scotch, and we just had this perfect match,” Topolsky said. “Our audience is hard to reach.” Other recent ad campaigns include Hewlett Packard Enterprise (with readers spending an average of 2 minutes and 30 seconds on that campaign, Topolsky said) and GE. You will need to turn off your ad blocker to see these ads, which do look nice. Hey, at least it’s not oil companies.

If The Outline can get to a break-even point, what will be next? More podcasts. One-off events. Print. “A physical publication at some point is something I’m very interested in — whether it’s a quarterly or something more frequent than that,” Topolsky said. He also envisions “sister brands” to The Outline. He wasn’t ready to talk about specifics, but a reader survey that The Outline has been running recently asks if, for instance, people would be interested in seeing more cultural, political, or tech content on the site.

Maybe The Outline will fail. If it does, it won’t be because of just one thing. It won’t be only because advertising doesn’t work, or because VC funding doesn’t work, or because freelancers boycotted it, or because its content wasn’t good.

Maybe The Outline will succeed. If it does, it won’t be because advertising works, or because they had the one good VC, or because freelancers got treated better, or because the content was good. It will be because of a lot of little pushes, a lot of little things going right.

“In a lot of businesses, you do the thing you love 20 percent of the time, and 80 percent of the time you’re cranking out some Trump post or whatever,” Topolsky said. “I think there’s just gotta be another way.”

“People want to say, this was the big mistake. This was the bad move. But a lot of this comes out of a culture where it’s believed that what will save the media is some big idea or some new model,” said Erik Hinton, the former Outline developer. “The things that ail the media can’t be saved by one person’s big idea, or one person’s masterful vision…I don’t think media can be saved by the brilliance of individuals.”

Laura Hazard Owen is the editor of Nieman Lab. You can reach her via email ( or Twitter DM (@laurahazardowen).
POSTED     Oct. 11, 2018, 10:45 a.m.
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