There Are Just Two Lessons We Can Learn From The Messenger’s Sudden Implosion

The logo for The Messenger with part of it obscured with a black smear so it reads "The Mess."

The Messenger, a digital news outlet that launched in May 2023, had grand plans. Its founder spoke often about a desire to not just build a thriving newsroom but to restore trust in media itself with a no-frills approach to reporting the news fairly and at scale. The Messenger would hire hundreds of journalists, it proclaimed (and then did), making itself one of the bigger news organizations in the country. And for about seven months, it was. Then, on Wednesday, it died a swift death, its employees all left without jobs and the website they worked for excised from the internet altogether. The only people surprised are the roughly 8 billion who did not design its business plan.

The outlet’s approach was shockingly vintage. The Messenger did not sell subscriptions. It did not launch a podcasting operation. It did not shill partnerships with brands in an effort to become a hub of sponsored content that passes for journalism-adjacent. Instead, the Messenger played the hits. Its leaders, led by longtime media entrepreneur Jimmy Finkelstein, planned out a website that would supposedly get tons of page views and make money by selling standard digital advertising that would appear alongside articles. That was a popular concept in 2010 or so, before tech giants swallowed up the vast majority of the digital advertising market that the Messenger declared would be its lifeblood. The Messenger projected that it would make $100 million in advertising revenue in 2023. It wound up bringing in between $3 million and $4 million, according to various reports over the past few weeks. The Messenger had $50 million in startup funding. Its loss in seven months was nearly all of that.

The failure was one of vision, not execution by a talented team of roughly 300 writers and editors. The Messenger’s founders built a website for a world that no longer exists. They played stupid games and won stupid prizes. The site’s biggest achievement in its nascency was being the first to report that Taylor Swift and Travis Kelce were “quietly hanging out” last fall. That story, like all the Messenger’s other stories, is now impossible to access unless you saved a copy somewhere.

It might be tempting, given the talent of the Messenger’s staff and the inevitable failure of the publication anyway, to take the end of the outlet as some kind of lesson on the state of the news media. But there’s no lesson here that attentive people didn’t learn many years ago. The first lesson is that time machines remain hard to acquire on any media company’s budget, even one with such generous funding. And the other lesson is that not all extremely rich people should be allowed to start media companies.

Before delving into the breathtaking naïveté and incompetence of the Messenger’s management, it’s worth foregrounding the wreckage those leaders have left in the wake of their mindless experiment. The Messenger either ran out of money this week to continue operating or decided to cut its losses before its accounts truly hit zeroes. Either way, the company’s leaders decided that their hundreds of employees would not get severance, nor even a few weeks to figure things out. Their jobs disintegrated on the last day of January, which is particularly cruel because it requires rapid action for employees to enroll in new health plans. In a memo to the departing workforce, the Messenger said employees would be eligible for COBRA “while there is an active plan.” But with no time left in their January coverage, enrolling in new plans became an immediate concern. One woman in the company’s Slack channel posted a question about what would happen to a planned surgery she had put on the books, Jordan Hoffman, a senior writer and critic at the Messenger, said. He didn’t have time to make out the woman’s name, he told me, before the company turned off employee access to Slack on Wednesday afternoon.

The Messenger’s leaders exited as they entered: without a workable plan. Hoffman told me that in the middle of the night before Wednesday, the company’s California employees got direct deposits that they quickly reasoned were paid-time-off days the company owed them upon cutting them under California law. (Hoffman isn’t in California, but word quickly spread around the company.) Most Messenger employees, he said, learned what was happening in the New York Times. “So first thing everyone is like ‘uhhhhh … any word from management?’ ” he explained to me in a message on X. “No word. Until the NYT story breaks and then a few mins of mayhem and we all get booted. The end.” Hoffman later wrote about the mess of the final few days for New York magazine, and by god, was it a messy final few days.

While Messenger employees did not learn about the end of their workplace from Finkelstein, he did send them an email expressing personal devastation about the end of his site, and he said he was “proud of what we achieved.” Evidently not so proud as to preserve any of it going forward: The website’s outright disappearance within hours denied the Messenger’s journalists a chance to preserve copies of their own work. No severance, no notice, and no access to their own portfolios. For that, Finkelstein is an absolute villain. His villainy appears to have been born from incompetence rather than malice, but the origin story doesn’t change what he’s done to the careers of hundreds of people.

One of the greatest tragedies of the Messenger is a hypothetical left unfulfilled: What could someone who wasn’t a complete naïf have done with a $50 million investment in a media company? What if an actual innovator with some regard for people’s careers had gotten a crack at building a sustainable media business with that kind of funding? We’ll never know, but we will at least have a new cautionary tale to teach in business classes about how to light $50 million on fire.

Finkelstein appears to have been under the impression not only that old-school advertising dollars would be easy to come by, but that the American public yearned for a website that was neither right nor left and had no viewpoint other than that of detached omniscience. To Finkelstein, that meant keeping coverage of Donald Trump’s civil fraud trial off of the site’s homepage, Semafor reported. (Finkelstein is also a longtime friend of Trump’s.) The move did not, in fact, result in droves of conservative readers becoming unyielding Messenger loyalists who could carry the company to profitability.

Finkelstein had reason to believe in a centrist news outlet built around some measure of objectivity. He helped found the Hill in 1994, and it became a reputable Beltway paper and later digital outlet that still exists today. Finkelstein took a controlling stake in 2014 and sold it at a $130 million valuation in 2021.

But the Hill began as a literal print newspaper, and the business has changed a bit since Finkelstein started it. The Hill also picked out a defined audience—political addicts who want to know what’s happening in the Senate cloakrooms at all times—and catered to its needs. The Messenger never had a constituency because nobody was dying for a middle-of-the-road outlet that covered a little bit of everything without one guy’s version of bias. Even with a business plan that wasn’t from the time of the Obama administration, it was hard to see any path to a successful business at scale.

The big problem was that the business plan was comical. Finkelstein reportedly paid the site’s editor in chief $900,000, the journalism world’s equivalent of an NFL team paying a long snapper $22 million. Maybe worse than that, Puck News reported that Finkelstein had suggested that if he stepped down as CEO, the company would save $1 million a year. Was the Messenger spending $1.9 million of its $50 million in funding on one editor and one CEO who gave himself the job? Whatever the answer, Finkelstein seemed intent on being a one-man stimulus package for a struggling corporate real estate industry. The Messenger had offices in New York, D.C., and Florida, and the Times reported it had spent more than $8 million on those spaces. Speaking as someone currently writing from the comfort of a home that Slate pays zero dollars for every year: How? The Messenger didn’t even force employees to work in those pricey offices. If this wasn’t a money-laundering operation, it wasn’t a good plan.

The one solace in the Messenger dying so quickly is that its employees and the rest of the world will not have to sit through more vanity exercises in hearing about what the outlet might become. As recently as three weeks ago, the company projected to potential investors that its advertising revenues would grow from $3.8 million in 2023 to $55 million in 2024, a multiple of more than 14 times year over year, per a pitch deck CNBC obtained. It was an exceptional display of charlatanism by people who transparently did not know what they were doing. The Messenger’s decline doesn’t tell us anything about what can work in media in 2024, or even what can’t, because regular people already knew that the Messenger’s strategy was an impending bust. That it then met its natural endpoint would be amusing if the people in charge hadn’t screwed so many good workers in pursuing their abject fantasy.