How to Burn Cash and Alienate People: Behind The Messenger’s Implosion

In the basement of a car dealership in Manhattan’s Meatpacking District last spring, The Messenger chairman and CEO Jimmy Finkelstein addressed a throng of New York’s media elite. Finkelstein was there to unveil his grand plans for a new website that he claimed would revolutionize the news, talking a big game in the process.

“When I was at The Hill, we did 125 million visits a month,” he told the gathering that featured media heavyweights Barry Diller, Kara Swisher, Chris Licht and Jen Psaki. “It was the second highest political site next to CNN. That’s with 70ish journalists and maybe 90 people in the editorial. Here, we are going to have hundreds of journalists. We are not just covering politics, we are covering sports, we are covering business, we are covering entertainment. So it’s hard to imagine why we couldn’t do it.”

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Sitting in the crowd watching at the Semafor Media Summit were The Messenger’s editor in chief Dan Wakeford, chief revenue officer Mia Libby and chief communications officer Kimberly Bernhardt, who appeared increasingly uncomfortable as Finkelstein riffed about his grand plans. Less than a year after making wild predictions of generating $100 million in revenue by attracting 100 million readers with a newsroom of 550 journalists, The Messenger has crashed and burned in spectacular fashion, leaving in its wake 300 staffers tossed to the media scrapheap without severance or health insurance in a failure that marks the end of the splashy media startup era. The money owed to freelancers and vendors is expected to balloon out to seven figures, The Hollywood Reporter has learned.

Throughout 2022, Finkelstein had turned to several swashbuckling editors to lead the site, courting former Vanity Fair and New Yorker editor Tina Brown, former Us Weekly and THR editor Janice Min, and former Cosmopolitan editor in chief Joanna Coles, who all turned down his overtures. Finally, Finkelstein hired Wakeford, a former editor of People magazine, to lead the site.

On the business side, he linked back up with former Condé Nast Media Group president Richard Beckman, who had been president of The Hill before Finkelstein sold it to Nexstar for $130 million in 2021, and who was given the nickname “Mad Dog” by former Condé Nast CEO Steve Florio, due to his hard-charging — and at times out of control — nature.

Florio had borrowed the nickname from former Drexel Burnham Lambert M&A specialist Jeffrey Beck, who as The New York Times wrote in his obituary, would howl through the corridors at the now-defunct investment bank when he succeeded in a money-making deal, like a mad dog.

Condé was forced to pay a reported multimillion-dollar settlement after Beckman, as a joke, tried to force two female employees to kiss, slamming one woman’s head into the other’s forehead and leaving one executive with a broken nose.

At The Messenger, Finkelstein, Beckman and Wakeford went on a hiring spree, offering to double prospective employees’ salaries, in one case trying to entice an editor with a more than $500,000 offer to run a vertical. By the time all three men posed in ill-fitting suits in March of last year, looking like a trio of ambulance-chasing lawyers, for a buzzy New York Times profile, many seasoned media observers were already highly skeptical of The Messenger.

The site launched in mid-May, and by then Beckman had already offended several colleagues by using phrases like “intellectual masturbation” on an almost daily basis to describe when he felt people were overthinking things, according to two people familiar with the matter. It was one of a number of allegedly crude sayings by the Brit, who worked with Finkelstein in relaunching THR more than a decade ago.

Two staffers filed HR complaints against Beckman for creating a toxic work environment, according to three people familiar with the matter. Beckman’s behavior and reputation resulted in several prospective advertisers refusing to work with The Messenger, according to the people familiar with the events.

“If you did something without him, you’d get a full tongue lashing,” a former Messenger staffer, who asked to remain anonymous for fear of retaliation, says. “It was bullying behavior. He would single people out. He would belittle them. He would use the old-school tactics to make people feel terrible. It was fear and intimidation.”

“I’ve always been a hard-driving leader, and I did my best to make this business work,” Beckman tells THR, while declining to specifically address the allegations. “I’m sure some people don’t like being challenged and pushed.”

Former staffers tell THR that Beckman displayed a complete lack of understanding about digital media and showed little interest in learning or taking input from the team of talented staff he hired. Worse still, those that worked with him say he was stuck in a bygone era, circa Condé Nast in the 1990s, believing he could secure million-dollar deals from advertisers. “If you were trying to comment on something or tell him something, he would cut you off and say, ‘Do not open your mouth, I don’t wanna hear it’ and then go on long tirades about his brilliance,” another former staffer says.

Ultimately, Beckman and Finkelstein, who were both paying themselves seven-figure salaries and spent big on multiple offices in three cities, failed to generate revenue streams or communicate a coherent business strategy to staff. Just how do you monetize commodity news that at times appeared to be a poor man’s Daily Mail online, without the sexy photos and sidebar of shame?

“The brand promise of creating a product that was balanced is a rock-solid idea,” Beckman tells THR. “Unfortunately, I don’t think the product had yet delivered to a point where it was going to take off. From an advertising perspective, we launched at the worst possible time, in the middle of the most challenging ad market since ‘09.”

The editorial side, led by Wakeford and former New York Post digital editor-in-chief Michelle Gotthelf, did break several stories, but a number of journalists, many of whom had given up stable jobs at legacy media brands, felt they had been conned by Finkelstein. “Most of us came in under the promise that we were going to get to build something, and then quickly it became clear that we were basically an army of rebloggers,” Amanda Bell, The Messenger’s TV editor, says. “Our original ideas were put to the side to accommodate this content factory.”

Finkelstein told prospective employees that he would not let The Messenger fail, as it was his legacy — a publication, he told friends, that would far outlive him. It was a point he touched on when being interviewed by Semafor editor-in-chief Ben Smith at the April event. “We are doing this because I really feel that if I have a legacy, it is to create a media site that is not only enjoyable to go to, but is completely fair,” Finkelstein said.

His father, Jerry Finkelstein, was a New York power-broker who owned The Hill and the New York Law Journal, which he turned into a lucrative cash cow. Jimmy’s brother, Andrew Stein, would go on to be New York City Council president. So, what now is to be made of Jimmy Finkelstein’s legacy?

“Talking about legacy it is interesting how you are writing from a publication whose greatness I created,” Finkelstein wrote in a statement to THR. “I was Chairman of The Hollywood Reporter. When I bought it it was a few pages of newsprint with a tiny web site that no one read. When I sold it it was one of the great publications in America.” (In 2009, then-THR owner Nielsen sold the publication to a consortium called e5 Global Media that included Finkelstein as chairman. In 2013, one of those partners, Guggenheim Digital Media, acquired the stake owned by Finkelstein’s firm.)

“My father was a wonderful man with his own great legacy, but mine is my own,” Finkelstein says. “I have always taken publications and grew and improved them.”

A version of this story appeared in the Feb. 7 issue of The Hollywood Reporter magazine. Click here to subscribe.

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