You Don’t Know Much About Jay Penske. And He’s Fine With That.

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

After the company bought a controlling stake in Vibe and Billboard, which have offices in New York, he flew there to meet with each new employee. “This was in the middle of the pandemic, and so I thought, ‘Wow, this guy is serious!’” said Datwon Thomas, the editor in chief of Vibe. 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 practice of meeting with each of his new employees soon after acquiring a property.

Mr. Penske will sometimes play hardball with the staff. When Tatiana Siegel, a longtime Hollywood Reporter journalist, accepted a job at The Ankler, a subscription newsletter started by the show business writer Richard Rushfield that has expanded under the former Hollywood Reporter top editor Janice Min, Mr. Penske put a stop to the move. Ms. Siegel’s contract included a noncompete clause, and Mr. Penske held her to it. The parties eventually agreed that Ms. Siegel would decamp to Rolling Stone, committing 80 percent of her work to it, with the remainder going to The Ankler.

“Jay has been 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 hold on entertainment coverage. The competition is reminiscent of what took place more than a decade ago, when Deadline had the old guard quaking. Mr. Rushfield said that start-ups may have an advantage over entrenched publications, because they are not beholden to anyone.

“If you’re at a publication like Variety, for example, the number of things a studio has over you is hard to keep track of,” Mr. Rushfield said. “You need friendly access to studio executives and agents gift wrapping your scoops. You need people for covers. You need people to speak at your conferences.” The result, he continued, is that “publications with different business models, and more aggressive reporting, can elbow their way in.”