Pop Culture

Jimmy Finkelstein, Low-Key Media Tycoon, Looks Beyond The Messenger’s Rocky Start

Jimmy Finkelstein, the veteran media investor, former owner of The Hill, and recent founder of digital news start-up The Messenger, prefers to stay at one of two places when he comes back to New York. The first is the Harvard Club, the 129-year-old members-only joint in Midtown. (His wife, former CNN producer Pamela Gross, is an alum.) The other is The Carlyle, to which Finkelstein invited me after I twisted his arm into sitting for an interview. When I arrived at the storied hotel on Tuesday morning, about 20 minutes late because traffic on the Upper East Side was a nightmare, The Messenger’s chief communications officer met me out front and took us up to her boss’s suite, where the towering (literally) 74-year-old tycoon greeted us in a black suit and purple tie. 

I had talked to Finkelstein, who spends most of his time these days in Palm Beach, at different points over the years, usually when his name was in the mix to buy some storied journalism institution that had fallen on hard times. (See: the Daily News; Time Inc.) This was our first in-person encounter. He’s mild and soft-spoken, to the point where I worried about his voice registering on my recorder, which I placed on a coffee table accompanying the couch into which Finkelstein lowered his 6-foot-4-inch frame. He told me his parents had lived in The Carlyle for 10 years and that he had a sentimental connection to the place. “I know so many of the people here,” he said.

On to the subject at hand: The Messenger had lifted off just more than a week earlier, with $50 million in funding, a $100 million revenue projection for 2024, and big plans for a 550-person newsroom. The prelaunch phase reminded me of the buzz preceding The Daily, the Rupert Murdoch–made iPad “newspaper” that chugged along for almost two years in the early 2010s—a lot of money and manpower being poured into a venture that people couldn’t quite wrap their heads around. But whereas The Daily debuted with a carefully choreographed, high-gloss presentation at the Guggenheim, with Murdoch onstage beside Apple’s Eddy Cue, The Messenger entered the world as a sort of beta-mode work in progress, essentially ironing out the kinks in real time. 

There’s no sugarcoating it: The reception among the media cognoscenti was downright savage, perhaps a little too savage (and a little too gleeful) considering this is a place hiring oodles of journalists (including some prominent ones) at respectable salaries, on the heels of a brutal season of layoffs that rattled publications far and wide. Reports about three editors handing in their resignations as if storming off of a content farm haven’t helped matters. (Gregg Birnbaum, a CNN and NBC News alum, excoriated the site for its “rapacious and blind desperate chasing of traffic” on his way out the door.)

I read Finkelstein a few sentences from Joshua Benton’s widely circulated takedown for Nieman Lab: “The thing that’s confusing about The Messenger to everyone else in the media world is that its ideas don’t make any sense. It’s in an aggressive sort of denial about the world of digital news publishing in 2023. It’s LARPing an earlier time. The Messenger thinks it will reach 100 million monthly uniques on the back of bland aggregation…. It thinks it can support a 550-person newsroom on programmatic advertising. The Messenger thinks the right pitch for a site funded by Republican mega-donors and run by the guy who brought the world John Solomon is: ‘We’re the unbiased ones!’” 

Finkelstein countered with an adamant response: “I sold The Hill a year and a half ago.” (To Nexstar for $130 million.) “The Hill made about $18 million [in profit]. We had 120 million visitors on average a month, with about 70 reporters and 90 people in the editorial department. Clearly, it wasn’t impossible, because we did it. Now we’re not only gonna have as large, if not larger, a political [audience], but we’re also gonna have sports and business and general news. So, I mean, it’s hard to imagine that we can’t do it.”

What seems to be tripping people up, I suggested, is that The Messenger’s hefty cost structure belies the mass-traffic CPM strategy it appears to be dabbling in, especially in a landscape where advertising-supported digital brands are, to put it mildly, having a rough go of it. Here’s where Finkelstein wanted to set the record straight. He gave me an earful about the business model he’s been hammering out with Richard Beckman, The Messenger’s president (as well as a memorable and controversial personality from the glory days of Condé Nast, who worked with Finkelstein both at The Hill and on Prometheus Global Media’s reinventions of The Hollywood Reporter, Billboard, and Adweek.) Addressing the barrage of early criticism, Finkelstein said, “Nobody bothered to ask about the model!” 

Fair enough, so let’s hear the guy out. Programmatic advertising—that’s the cheap and automated stuff—is just one piece of the puzzle, said Finkelstein, whose official title is chairman and CEO. Direct sales will begin this summer, as The Messenger rolls out verticals including news, politics, business, sports, entertainment, technology, health/wellness, food, travel, and style. “We’re going after very large advertisers. We expect to have tens of millions of dollars in direct sales in the first year.” 

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