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Welcome back to In the Room. I’m Dylan Byers. In tonight’s email, we focus on the predictable decline and collapse of The Messenger, which Jimmy Finkelstein finally put out of its misery on Wednesday. In doing so, Finkelstein made a weak attempt to pin the company’s failure on the aforementioned economic headwinds. Of course, as everyone and their mother knows, this failure was written from the jump.
 ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ 
In The Room

Welcome back to In the Room. I’m Dylan Byers.

It’s a season of new beginnings here at Puck. On Tuesday, our West Coast contingent celebrated the arrival of new C.E.O. Sarah Personette with a lively and spirited dinner at Evan Funke’s Mother Wolf. A few hours earlier, John Ourand, the newest addition to Puck’s talent roster, preempted the launch of his highly anticipated sports business franchise, The Varsity, with a market-moving scoop about the sale of the Baltimore Orioles to private equity giants David Rubenstein and Mike Arougheti.

Even by the kinetic standards of startup life, this was one of those weeks when you really feel the momentum at your back, and it’s inspiring to see Sarah and John jumping on board at full throttle. (Note to Inner Circle members: John will be hosting a private call about the future of the sports business tomorrow with Jon Kelly. Everyone else: You can upgrade your subscription here, and email fritz@puck.news for a link to their conversation.)

Alas, the broader media industry is still facing extraordinary headwinds, as evidenced by the slew of layoffs that continued apace at a great many companies. Impending staff cuts at The Wall Street Journal’s Washington bureau, which I first reported last Wednesday, will officially commence this week. This comes amid broader cuts to D.C. bureaus across the legacy media landscape, as beleaguered regional newspapers struggle to justify the expense of competing in an already oversaturated market.

In tonight’s email, however, we focus on the predictable decline and collapse of The Messenger, which Jimmy Finkelstein finally put out of its misery on Wednesday. In doing so, Finkelstein made a weak attempt to pin the company’s failure on the aforementioned economic headwinds. Of course, as everyone and their mother knows, this failure was written from the jump.

But first …

🗞️ Will Lewis watch: New Washington Post C.E.O. Will Lewis told staff this week that he won’t outline his specific, detailed plans for growing the paper’s business until May. In the meantime, he plans to create nine working groups to focus on fixing the business’s most pressing challenges, starting next week. This is the first step in the TED Talk-ready business formula he devised that I first reported on last week: “Fix It” (address existing challenges), “Build It” (launch new initiatives), and “Scale It” (self-explanatory).

🐎 Zucker’s Telegraph chase, cont’d: U.K. regulators, presumably miffed at Jeff Zucker’s RedBird IMI for tweaking the terms of their proposed Telegraph and Spectator takeover, have issued a legal order preventing the Abu Dhabi-backed firm from making any further changes to the deal while they conduct their probe. For those who missed it, I reported on Zucker’s latest strategic moves last week—as well as the latest Oliver Stone-style conspiracy theory about his endgame.

🎙️ Linear’s NFL lifeline: On today’s edition of The Powers That Be, Peter Hamby and I discuss the NFL’s role in delaying the decline of pay TV, and what might come next. Plus, stick around for Eriq Gardner’s take on a surprise ruling in a Murdoch defamation case. Listen here.

Jimmy’s Quibi
Jimmy’s Quibi
News, notes, and reflections on a totally predictable, ego-driven, anachronistic media tragedy.
DYLAN BYERS DYLAN BYERS
In mid-January, Jimmy Finkelstein privately conceded to some friends and business associates that his last-ditch efforts to save The Messenger, his media startup built on a decidedly anachronistic business strategy, might not pan out. By that point, of course, the full scope of his mediaco’s rapid yet entirely predictable demise had been laid bare for all to see. The company that he brought to market in May 2023, propped up by $50 million in funding and an audacious business plan to make $100 million in annual revenue, never passed the smell test. Not only was it predicated on the sort of disintermediated, traffic-at-all costs strategy that nearly euthanized the entire industry, and run incredulously by the indestructible Richard “Mad Dog” Beckman, but it was… nowhere. Did you ever read a Messenger story? I didn’t.

In many ways, in this very public industry, the story of The Messenger was akin to a chronicle of a death foretold. Sure, there were rumors about the company’s exorbitant burn rate, but no one thought it would burn out so quickly. Instead, over eight painful and humiliating months, The Messenger spent around $43 million, generated a mere $3 million in annual revenue, and, by the end of 2023, had less than $1 million in cash on hand. Needless to say, this was well short of the necessary cash to sustain its $5-million-a-month burn rate. And the horrific governance and cash management made it a D.O.A. rescue or bridge investment opportunity, even to Finkelstein’s many well-heeled Palm Beach friends.

The Chronicle
To the rest of the industry, of course, this dire financial picture was the inevitable result of Finkelstein’s misguided investment thesis and his illogical faith in an outdated traffic-and-display advertising business model built on the back of a 300-person newsroom. Even his cri de coeur that The Messenger strove to be a trustworthy and nonpartisan media organization seemed ill-considered. A slightly more curious entrepreneur might have noticed that Axios, the AP, the FT, Yahoo, and other media companies have already overtaken that turf.

A more astute entrepreneur would have also appreciated the more macro trends in the industry. First and foremost among them: The decade-long disruption to the front line of American media—the Times, The Washington Post, the aforementioned FT, and more—has largely been settled. The incumbents generally fought off the insurgents, and yet even they are being forced to resize into a crowded and low-margin market. The Washington Post just laid off 240 people. The L.A. Times is in utter free fall and will almost certainly never justify the $500 million its owner paid for it and other assets. Even Business Insider, the only aughts pure-play to truly rival the legacy general-interest publishers, just cut nearly 10 percent of its workforce.

Finkelstein may have conceived a bad business idea in an unfriendly market, but nevertheless maintained his faith until the end, and went searching for an infusion of emergency funding to keep the business on life support. He set a target of $20 million, enough to sustain the business for at least four more months and, presumably, allow himself time to find a buyer.

To media executives looking from the outside, this always seemed Sisyphean. How could even a connected and wealthy guy credibly ask investors to throw good money after bad? How could he not have reduced the burn rate to a more responsible number? Why would even the sharkiest or most sympathetic investor partake in an opportunity that had yet to establish product-market fit?

In those mid-January conversations, according to people he solicited, Finkelstein said he had managed to secure guarantees for about half of the funds needed. (Was he talking about his own money, one wonders?) He also said that he was willing to take some drastic measures to avoid a shutdown—including stepping down as C.E.O., which he suggested could save the company around $1 million in annual expenses, a darkly comical admission. (Finkelstein did not respond to my request to speak; a spokesperson for The Messenger declined to comment.) Delusional as it may have been, Finkelstein saw The Messenger as his legacy and didn’t want it to fail, sources familiar with this thinking said.

Alas, fail it did, and in predictably chaotic fashion. On Wednesday, shortly after The New York Times broke the news of his decision, Finkelstein sent a memo to staff: “I am personally devastated to share that we have made the painfully hard decision to shut down The Messenger, effective immediately,” he wrote. “Over the past few weeks, literally until earlier today, we exhausted every option available and have endeavored to raise sufficient capital to reach profitability. Unfortunately, we have been unable to do so, which is why we haven’t shared the news with you until now. This is truly the last thing I wanted, and I am deeply sorry.” Shortly thereafter, Messenger employees were locked out of their Slack and email accounts. By Wednesday night, the site itself had been taken down, and the 300 newly unemployed journalists learned that they would not be receiving any severance.

Another One Bites the Dust
The ensuing schadenfreude came fast and furious, not least because The Messenger’s failure was both foreseeable and foreseen. Indeed, even the very first Times story breaking news of the venture seemed like a sort of media Space Cowboys spoof, indicating that the company was a relevance vehicle for Finkelstein and Beckman, who cashed out of the last era of digital media too early to appreciate its eventual demise. The duo sold The Hill to Nexstar Media Group in 2021 for $130 million, or $100 million-plus more than the current market cap of BuzzFeed. Business model aside, Finkelstein’s stated nostalgia for legacy media brands like 60 Minutes and Vanity Fair should have been its own red flag.

Nevertheless, in one final display of tone-deaf ineptitude, Finkelstein on Wednesday sought to place the blame for his failure on the broader economic forces that have precipitated a slew of layoffs across the industry. “The industry has faced extraordinary challenges this past year,” he wrote in his memo. “The economic headwinds have left many media companies fighting for survival. Unfortunately, as a new company, we encountered even more significant challenges than others and could not survive those headwinds.” That’s a brave thing to say to 300 journalists you’ve just put out of work because of your own delusional business plan, and, of course, it’s an explanation no one in the industry buys.

“You know the facts: No one who knew anything would think you can make money off traffic and hit the dumbass numbers he put out there,” Jim VandeHei, the co-founder of Axios and Politico, told me on Wednesday. “I was pissed the moment I heard about this dumb idea. It was business malpractice and human cruelty at an epic scale. Anyone who knew anything about the economics of media knew it would die quickly, spectacularly, and sadly. I am pissed on behalf of the journalists sold snake oil.”

On the bright side, The Messenger quickly finds itself in rare company, alongside Quibi and Luminary, in particular, as exorbitantly expensive, head-scratching media companies that quickly met their demise. What’s one thing all have in common? Quibi, of course, was brought to life by Jeffrey Katzenberg, a billionaire who defined his generation in Hollywood and became perhaps the most important player in Democratic politics, and Meg Whitman, a public company C.E.O. and political aspirant. Luminary was the brainchild of Matt Sacks, the son of billionaire investor Michael Sacks. And Jimmy Finkelstein, the son of a self-made publisher and New York political mucketty muck, has already made his fortune. The Messenger may be toast, but he’ll be just fine.

FOUR STORIES WE’RE TALKING ABOUT
Biden’s Dry Powder
Biden’s Dry Powder
The Blob gossip surrounding Biden’s Iran response.
JULIA IOFFE
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Streaming’s Sports Groupthink
Interrogating the conventional wisdom surrounding the sports doc boom.
JULIA ALEXANDER
Haley’s Donor Lasso
Haley’s Donor Lasso
Updates from the Four Season Palm Beach donor summit.
TEDDY SCHLEIFER
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Leather Heads
On the unassailable fashion dominance of Hermès.
LAUREN SHERMAN
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