You don’t know much about Jay Penske. And he likes that.

Ten Penske Media employees interviewed for this article describe their boss as someone who stood up for troubled publications. “Jay Penske came in and saved this company,” said Dea Lawrence, Variety’s chief operating and marketing officer. “He is a hero to the publishing world.” His company has more than 1,350 employees, according to Penske Media vice chairman Gerry Byrne, nearly half of them journalists and content creators.

After the company bought a majority stake in Vibe and Billboard, which have offices in New York, he flew there to meet every new employee. “This was in the middle of the pandemic, so I was like, ‘Wow, this guy means it!'” said Datwon Thomas, Vibe’s editor-in-chief. Mr. Thomas met Mr. Penske for lunch at Bryant Park Grill in Midtown. “Jay knew a lot about me and my background,” he said, “and he knew a lot about Vibe.” Four other Penske Media employees said that Mr. Penske makes a habit of meeting all his new employees shortly after acquiring a property.

Mr. Penske sometimes plays hard with the staff. When Tatiana Siegel, a regular Hollywood Reporter journalist, took a job with The Ankler, a subscription newsletter started by show business writer Richard Rushfield and expanded under former Hollywood Reporter editor Janice Min, Mr. Penske put an end to the move. Mrs. Siegel’s contract contained a non-compete clause and Mr. Penske kept her to it. The parties eventually agreed that Ms. Siegel would leave for Rolling Stone, where she would spend 80 percent of her work, with the rest going to The Ankler.

“Jay is by far the best owner I’ve worked under at The Hollywood Reporter,” said Ms. Siegel, who joined the magazine in 2003. “My situation was unique and it was resolved amicably.”

The upstart publications Puck and The Ankler pose a new threat to Penske Media’s grip on entertainment reporting. The match is reminiscent of what happened more than ten years ago, when Deadline was shaking the old guard. Mr Rushfield said start-ups can have an advantage over entrenched publications because they are not obligated to anyone.

“For example, if you’re on a publication like Variety, it’s hard to keep track of the number of things a studio has about you,” said Mr. Rushfield. “You need friendly access to studio managers and agents who will gift you firsts. You need people for covers. You need people to speak at your conferences.” The upshot, he continued, is that “publications with different business models and more aggressive reporting can work their way in.”

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