Inside the Messenger's money-torching bet to make media great again – The Washington Post

NEW YORK — Seated in a private room of a Manhattan club so exclusive that the public relations flack in the room asked it not be named, Jimmy Finkelstein insisted that all was well at the new publication he started with a mission of restoring America’s trust in media.

“Advertisers are more and more coming on,” the veteran publishing executive said. “The audience is growing very nicely, and I think we’re on the road to success.”

That was September, and his vote of confidence was a rebuke to doubters who had questioned the Messenger’s entire premise from the start.

When the Messenger launched in May — with a $50 million investment that swiveled heads across the media industry — Finkelstein projected that it would have as many employees as the Los Angeles Times and traffic to rival the New York Times within a year. He promised his site would stand apart in a crowded, struggling mediasphere by being nonpartisan, unbiased, purely objective.

The dream seemed far-fetched to industry observers familiar with the layered challenges facing the news business, but Finkelstein dismissed the haters. After all, he had turned his last media venture, the Hill, into a Beltway juggernaut, sold in 2021 for $130 million. As he told Vanity Fair in May, “It’s hard to imagine that we can’t do it.”

Now, just eight months after its launch, it’s no longer hard to imagine. Two weeks ago, the company laid off about 20 employees, 7 percent of its staff; its president announced his departure; and Finkelstein told panicked staffers that he was trying to secure more funding to keep it afloat. The New York Times reported that the Messenger was down to its last $1.8 million, after only earning $3 million last year. CNBC cited a leaked document predicting that it could be $16 million in the hole by June.

The Messenger declined to comment on specific figures but said it recently raised another $10 million and plans to launch a revenue-generating TV division this year.

Throw a stick and you’ll hit someone trying to save journalism. From grizzled publishers of legacy newspapers to scrappy founders of local news nonprofits, every media player is looking for new ways to make money and renew the public’s faith. Surely, there are lessons to be gleaned from the Messenger’s trajectory.

But as of last week, Finkelstein didn’t seem ready to entertain them.

“The world is saying that we have a great site, the world is saying that it’s a fair site, and the world is believing in our mission. And revenue will come,” he said in an interview Tuesday. “We’re as far to the left as the right will go and we’re as far to the right as the left will go, and I think that is one of the secrets to our success.”

A few weeks after the Messenger launched, news director Neil Sloane spotted an item on a list of story assignments that struck him as dubious.

It was a report picked up from a Las Vegas TV station about a Nevada family who told police that an alien spacecraft had crashed in their backyard, producing two big-eyed, eight-foot-tall “nonhuman” creatures. Officers arrived on the scene to find zero evidence of interstellar visitors.

Sloane, a veteran of the New York Post, dismissed it in a short note that he appended to the list, viewed by The Washington Post: “This is BS and we should not run [it].”

Hours later, though, this headline appeared on the Messenger’s site: “‘Terrified’ Family Calls 911 … Over ‘Aliens’ Crash Landing in Backyard.”

The Messenger had promised to “champion balanced journalism in an era of bias, subjectivity, and misinformation,” and Finkelstein, in his early hype, had spoken of golden-age “60 Minutes” and Vanity Fair as role models.

In practice, the Messenger often functions like a “content farm” where teams of reporters aggregate stories from other news outlets and social media, according to current and former staffers.

“Their motto was ‘post now, correct later.’ Flood the zone,” said Kristin Bender, one of several editors who quit within weeks of the site’s formal launch. “Basically all they were doing was taking stories from other news publications.”

Though Finkelstein said the Messenger would reduce its reliance on news aggregation as it hired more reporters, the site’s business plan has always been hitched to a high-volume publishing strategy.

To oversee it, Finkelstein tapped digital guru Neetzan Zimmerman, who made his name a decade ago as a one-man traffic machine at Gawker — where he had a mandate to post any story he thought could go viral — and later at the Hill. (“Neetzan’s peculiar brand of expertise allowed me to not worry about traffic numbers and give the rest of the staff an opportunity to do more creative and satisfying work,” former Gawker editor A.J. Daulerio said.)

Yet staff noticed that the impulse could lead the Messenger to questionable places. In September, it published a story built around a post from Libs of Tik Tok — a controversial anti-LGBTQ+ social media account — citing an unnamed hospital employee offended by diversity training that featured interviews with people who said they knew they were trans from a young age.

“If the New York Post or the Daily Mail covers something, editors here think it’s worth covering and they don’t seem to stop to consider, well, is this an actual news story or is this an invented culture war thing?” a staffer said, speaking on the condition of anonymity to preserve relationships.

As the site developed, it produced more original stories. The Messenger broke news of Vivek Ramaswamy’s political director jumping ship for the Trump campaign; and the New York Police Department conducting a wellness check at the home of a top fundraiser of Mayor Eric Adams (D), hours before the FBI raided it in a campaign-finance corruption probe. In July, it scooped the world on Taylor Swift and Travis Kelce “quietly hanging out.”

“There’s a group of people who are actually attempting to do the kind of reporting you would expect from an aspiring national news outlet,” said a staffer who also spoke on the condition of anonymity to maintain work relationships. “It just gets drowned out by chum.”

The thing about chum, though, is that a lot of fish are willing to bite. Recent headlines have included: “TikTok Influencer Says She Was Shamed For Wearing ‘Inappropriate’ Amazon Dress to a Wedding,” “Florida Man ‘Launched’ Into Garbage Truck During Trash Pickup Gone Wrong” “Mom of Three Says ‘Crackling’ Noise Inside Her Ear Turned Out To Be a Spider’s Nest.”

Finkelstein’s new business idea was vintage, harking back to the early 2010s when publishers wanted two things: content and more content. The operating idea back then was that more stories meant more clicks meant more ad sales and, eventually, profitability.

“There’s a direct correlation between traffic and revenue,” he said last week, “because you bring in programmatic revenue by increasing your traffic.”

Yet it’s a business model that many other publishers have lately steered away from.

“The relationship between traffic and sustainable revenue, let alone profit, is not as obvious as it once was,” said Caitlin Petre, author of “All the News That’s Fit to Click” and a Rutgers University professor of media studies. She cited a number of reasons businesses are hesitant to advertise on news sites — social media platforms that have de-emphasized news, privacy-minded regulations that made it harder to target specific reader niches, fear of wasting ad dollars on what might turn out to be junky AI-generated sites.

There is still money to be made from digital advertising, she added. “The question is whether it can keep a media business afloat.”

It’s the reason many other media start-ups — sites like Puck, Punchbowl and Semafor — have instead targeted refined audiences that they hope will buy subscriptions or attend their events where they can be exposed to the branded generosity of blue-chip corporate sponsors.

Finkelstein insisted last week that the Messenger’s massive news offering — from national politics and lurid crime to sports and celebrity gossip, with dollops of heartwarming fluff (“Firefighters Rescue Three-Week-Old Puppy Who Got His Head Stuck in a Can”) — was working. In December, he said, it racked up 24 million visitors, only about a quarter of the way to their goal of 100 million but significant for a site building an audience from scratch.

Ad revenue was a different story. Finkelstein declined to comment on specific numbers, “but I will say that we’ve sold in this one month almost as much as we have sold in the last year.”

In October, the Messenger announced that it was “doubling down on our commitment to fact-based journalism standards” by partnering with an artificial intelligence start-up.

While other media companies have dabbled in AI to build out their offerings of news-adjacent content — product reviews, listicles, how-to guides or sports recaps, with some disastrous results — Finkelstein’s company advanced a somewhat different proposition: It would use AI to ferret out subjectivity in its articles and rate stories on a “reliability” scale, from “very low” to “very high,” and on a “political lean” scale, from “left” to “right.”

“We believe Seekr’s responsible AI technology will help hold our newsroom accountable to our core mission,” the company’s then-president, Richard Beckman, said in a statement announcing the partnership with the Virginia-based company.

Staffers were surprised and confused. And a closer look at Seekr’s patented evaluation tools raised more questions.

How exactly would its AI technology determine political lean? According to Seekr’s website, the software tracks “expressions, keywords, and semantics strongly associated with a particular political lean” — offering, as an example, that the word “woke” typically appears “in right-leaning content used to describe left-leaning agendas.”

That’s an unusually frank understanding of the word. But simply including any single word in a story doesn’t necessarily point to political bias. Seekr did not respond to The Post’s request for comment.

Editor in Chief Dan Wakeford reassured staff in an email that they were “not mandating the use of Seekr’s technology in our newsroom.” Instead, he wrote, the Messenger would simply apply its results to “a small selection of our stories” and showcase them on the site to demonstrate how Seekr works. The partnership was essentially an advertising deal.

Around the same time, the Messenger was the subject of several news stories about its travails that stirred schadenfreude in media-gossip circles. One in the Daily Beast claimed that Beckman had been telling his own staffers that the Messenger was “running out of money.”

The Messenger denied the report. Seekr’s AI-powered evaluator, though, gave the Daily Beast story a “reliability” rating of “very high.”

Kimberly Bernhardt, a representative for the Messenger, said its partnership with Seekr “has been very successful.”

The Messenger’s messaging has hinged on the idea that it has no point of view, no thumb-on-the-scale bias — that it’s merely serving up informative, accurate, agenda-free news for audiences of all stripes.

Finkelstein — who was born into a wealthy New York publishing family and name-checks dear friends across a political spectrum from Donald Trump to former congresswoman Carolyn B. Maloney (D-N.Y.) — said he leaves editorial decisions in the hands of managers he hired to accomplish the Messenger’s mission.

“The point is, I don’t want my view to be the view of the Messenger,” he said in September.

But in November, amid Trump’s civil fraud trial in New York, Finkelstein did have a little request for his editors.

“Jimmy does not want any Trump trial coverage on the [homepage], period. I’m repeatedly getting calls on it,” Deputy Editor Michelle Gotthelf wrote in an interoffice message to several other editors viewed by The Post. “Please make sure we don’t slip one in.”

In a flurry of exchanges, which were first reported by Semafor, editors expressed concern about the edict.

“Is it the reason i think we’re all assuming — that he doesn’t want bad press for trump?” replied Lisa Letostak, then the homepage editor.

Gotthelf suggested that Letostak contact Finkelstein with questions, which Letostak did. Finkelstein responded that his directions were misunderstood and that coverage of the trial was allowed on the homepage as long as it was balanced.

“All I said is you can’t lead every day with [the Trump trial]. You can put it up top but can’t always lead. It looks completely one sided. … I merely said firmly you need balance, that’s what we are about,” he wrote.

Letostak, who was fired in December, told The Post that “Messenger readers, staff and investors deserve to know how Jimmy Finkelstein has influenced editorial decisions.”

Finkelstein reiterated Tuesday that it had been a miscommunication. Gotthelf told The Post: “The Messenger has covered the Trump trials more than any other U.S. publication, and our stories are always on the front page and often at the top.”

Finkelstein explained in September that achieving impartiality is a straightforward matter of balancing “both sides.”

“This is absolutely true in our opinion section. Our editor actually keeps a record,” he said. “Basically it’s 50 percent on both sides.”

He mentioned that law professor Jonathan Turley (“clearly on the right”) writes a column for the Messenger and that “I know that we’ve asked [legal scholar Laurence] Tribe. We have to convince him, we would like him to write for us. He’s a distinguished constitutional lawyer at Harvard and obviously is more on the left.”

On one topic, though, the Messenger has kept its range of perspectives fairly limited.

Between Oct. 7 and Nov. 1, the Messenger published more than four dozen opinion pieces about the Israel-Gaza war and its ramifications. There have been takes on the evil of Hamas (“exponentially far more evil than the fictional Hannibal Lecter”), defenses of Israel against war-crime charges (“not every civilian death is a war crime”), consternation over a surge in pro-Palestine sentiment among young people (“schooled by professors who have filled their heads with the benefits of socialism”) — and several pieces that argued for a continuation of Israel’s assault on Gaza.

On Oct. 13, the Messenger published a piece by military analyst Harlan Ullman arguing that Israel “has no alternative except to launch a full offensive against Gaza” on par with “Stalingrad, the siege of Warsaw and the battle of Fallujah.” And on Nov. 1, a day after Sen. Dick Durbin (D-Ill.) became the first U.S. senator to call for a cease-fire, the Messenger published an opinion piece by pollster and political strategist Mark Penn (also a Messenger investor) titled “A Ceasefire for Hamas?” The answer: no. “When Hillary Clinton says there can be no ceasefire with Hamas, she knows what she is talking about,” he wrote.

A review of the Messenger’s opinion page shows that it has not published any pieces arguing for a cease-fire or any columns by Palestinian writers.

“Our opinion editors make an effort to ensure we cover a variety of viewpoints on a huge array of topics,” said Bernhardt, the Messenger representative.

A little more than a year before the Messenger launched, another well-financed news start-up with big ideas made its debut. It was called Grid, and it aimed to give readers a “fuller picture” of the news, with in-depth features exploring multiple perspectives.

But Grid struggled to find an audience and make money. Investors grew restless. In March, Finkelstein’s fledgling news company announced it had acquired Grid from its Abu Dhabi-based parent company IMI, which decided to invest in the Messenger instead.

“We are thrilled to be associated with [Grid’s] brand and talented team,” Finkelstein said in a statement at the time.

For now, the Messenger is still hoping to avoid Grid’s fate. But if Finkelstein’s strategy doesn’t pan out, could the company be folded into some other new entity?

A group of conservative investors — including Omeed Malik, the money man behind Tucker Carlson’s new media venture, and George Farmer, the CEO of right-wing social media platform Parler — met with Finkelstein at Trump’s Mar-a-Lago Club in Florida this month to discuss a deal to buy a controlling stake of the company.

It’s a move that could well mean an end to the publisher’s idealistic notion of a “nonpartisan” news hub — and perhaps his own role in it as well.

Finkelstein would only confirm that the company was exploring multiple options.