How Jimmy Finkelstein’s The Messenger Burned $50M In Less Than a Year

The Messenger founder Jimmy Finkelstein and journalist Ben Smith.
The Messenger founder Jimmy Finkelstein (L) and journalist Ben Smith (R). Michael Loccisano/Getty Images for Semafor

The digital news startup The Messenger officially shuttered on the last day of January after less than a year in operation. Its website was a blank page as of yesterday (Jan. 31), and the publication has let go of its approximately 300 staffers. The ambitious undertaking by the media investor Jimmy Finkelstein cost $50 million to launch last year, which raised eyebrows in the industry as skeptics questioned how sustainable the endeavor could be.  

The Messenger’s shuttering is another hit to the digital news industry, and Finkelstein’s letter to staff citing “economic headwinds” for the publication’s failure feels familiar to those following media news. But Finkelstein’s exorbitant spending on the site is unusual by industry standards. His plan to achieve $100 million in revenue relied heavily on old-school digital advertising (and an events sector) at a time where many news organizations were looking for alternative revenue streams. He also pledged to hire 550 journalists within a year in order to compete with heavily-staffed papers like The Los Angeles Times and The Washington Post. 

Axios founder Jim VandeHei told Puck News that The Messenger was a “dumb idea.”  Axios was the first outlet to report about Finkelstein’s venture last year. “It was business malpractice and human cruelty at an epic scale,” VandeHei said. “Anyone who knew anything about the economics of media knew it would die quickly, spectacularly, and sadly.” 

Finkelstein previously owned The Hill. He sold the political news site to Nexstar Media Group in 2021 for $130 million, which he used as justification for The Messenger’s lofty goals. He also co-owned The Hollywood Reporter and has tried his hand at other media buys like The New York Daily News. 

In a letter to staffers, Finklestein said, “Over the past few weeks, literally until earlier today, we exhausted every option available and have endeavored to raise sufficient capital to reach profitability.” The last-ditch efforts made by Finkelstein including an unsuccessful attempt to raise up to $20 million in two weeks, according to Semafor, and a failed bid to sell The Messenger to the LA Times

The Messenger appeared to have given little notice to its employees. Many found out about the closure through The New York Times and Semafor, which first reported the news. Dan Wakeford, The Messenger’s editor in chief, reportedly posted in company Slack that he was “not in the loop” when employees pressed him for information. Semafor reported some employees had received an extra paycheck yesterday labeled “vacation day payout,” an eerie signal that bad news was on the way. Many workers said they would not receive severance checks or health insurance.  

Film critic Jordan Hoffman, a former staff writer for The Messenger, shared his experience in the end days of the publication in an op-ed for the New York Magazine today. He said he and other journalists who worked there knew the publication was a risky bet, but it offered something that many publications don’t have much of anymore: a full-time staff job. 

“Though I have bylines everywhere, it’s been a while since I had a staff position. Sure, this Finkelstein character seemed a little questionable (my God, his wife came up with Melania’s Be Best campaign), but they were offering a dental plan,” Hoffman wrote. 

How Jimmy Finkelstein’s The Messenger Burned $50M In Less Than a Year

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