How new tech publication 404 Media is pitching itself to advertisers

In mid-November, Jason Koebler, co-founder of tech publication 404 Media, wrote on LinkedIn that the news site was looking for advertisers. That wouldn’t be all that notable—except for the fact that a few days earlier, Koebler authored a piece about the shutdown of the feminist website Jezebel, calling brands and the brand safety industry out for being “overwhelmingly conservative about advertising against news content, in a way that has been devastating to ad-supported news sites.”

404 Media, a worker-owned publication founded and operated by a team of reporters and editors that left Vice’s tech-focused pub Motherboard in August, has faced its own brand safety hurdles, since it covers everything from sex tech to surveillance tech, Koebler told Marketing Brew. That doesn’t mean it isn’t open to finding the right partners; the site’s investigative journalism doesn’t have to be incompatible with advertisers.

“I think we’re pretty unapologetic about what we cover. We’re not frivolously trying to terrify brands,” he said. “We are writing about these things in a responsible way, and audiences are responding to that.”

New new media

404 Media adds to a growing crop of worker-owned publications, like the New York City-centric Hell Gate and the (mostly) sports site Defector, which made headlines when its staff broke away from Deadspin in 2019 after new ownership told them to “stick to sports.”

Many of those worker-owned publications, though, have largely opted to monetize their publications without advertising. Defector, for example, disclosed that in its first year, 95% of its revenue came from subscribers and noted that outside of a few small, DTC brands, the company was focusing on other areas of the business rather than advertising; a year later, Defector said it had “largely stopped” running ads on its site and in its newsletters. (The company put “minimal effort toward sales” in 2023, according to another annual report, but has noted that it remains “very much open to inbound inquiries from brands.”)

But 404 Media is seeking out advertiser support. The site recently struck up a partnership with ad sales company BuySellAds, which helped 404 Media plug into the programmatic ad ecosystem in mid-October.

Those programmatic ads still represent a “very small portion” of the publication’s revenue, and for a newsroom that covers surveillance and data collection, Koebler acknowledged the less savory parts of programmatic advertising. With that said, “I approach it from a we-live-in-society sort of way; the entire internet has ads, and a lot of them are programmatic,” he told us.

“I don’t think that programmatic is our future,” he said. “I think that a brand that proactively decides to buy ads on our site is going to be better for our readers than ads that are just randomly programmatically placed there.”

404 Media has inked some direct deals through its partnership with BuySellAds, too, including with the PR agency Codeword and data protection service DeleteMe, Koebler said. (As part of the arrangement, BuySellAds gets a cut of the revenue.) A banner ad on the site for Codeword is customized, reading “the only marketing agency where everyone reads 404 Media.”

From Vice to virtue?

Before co-founding 404 Media, Koebler served as editor-in-chief of Motherboard, Vice’s tech vertical, where he saw firsthand that advertising and sponsored content were bringing in “very real money” for Vice. (Vice declared bankruptcy in May, and its financial woes have been attributed to a number of eyebrow-raising business decisions; Koebler noted that Motherboard didn’t have a dedicated salesperson the last few years he worked there.)

Seeing how sponsored packages and pre-roll ads could help monetize the work of journalists helped inform how he thought about bringing ads to 404 Media. “Having seen that there is potentially real money to be made from advertising, I didn’t want to discount that as a possible revenue stream,” he said.

Given 404’s small size—it’s just four full-time journalists—everyone has pitched in to help work with BuySellAds. 404 Media’s approach, Koebler said, is to be transparent and honest with readers.

“They know where we stand and can see we’re doing important journalistic work, but we also need to pay our rent, and we also need to make ends meet,” he said.

As the team works on growing out site monetization, the site remains “pretty unapologetic” about what it chooses to cover, which has included a scoop about an “aircraft-killing drone” and an investigation into an AI platform creating content that “could be categorized as child pornography.”

Like he wrote in November, Koebler said brand safety companies’ algorithms pose a risk to entirely ad-supported sites that choose to cover serious topics. Plus, “I don’t think brand safety matters to our readers,” he added.

That means that diversifying revenue is key. Brand safety limitations don’t have any impact on subscription revenue, and other ad-supported work can fund other projects readers might care about.

“There is a way for advertising to support journalism in a way that is not gross and in a way that doesn’t influence the journalism,” Koebler said.