Back in April, 1966, Time magazine famously asked America the big question: “Is God Dead?”

Thirty years later, as Time Inc.’s Corporate Editor at Large, Dan Okrent posed an equally existential question: “Is Print Dead?” His answer: An unequivocal “yes.”

“Finished. Over. Full stop,” he declared in a 1999 lecture at the Columbia School of Journalism.

Despite that, it’d be unfair to call Okrent the Grim Reaper. (Just don’t ask what he said about Detroit in the early 2000s). A lifelong realist, Okrent simply viewed digital delivery as the most sustainable path forward for magazines, thanks to the skyrocketing cost of paper, printing, and postage. Publishers, however, ignored Okrent’s prophecy, and continued to feast on their circulation revenues while treating their digital efforts purely as supplemental to print.

“How do you say goodbye to that cash? You don't. And then you end up seeing what happened in the slaughter of the next 10, 15 years. And this was before the smartphone!”

Okrent made his name as the cofounder of the highly-acclaimed regional, New England Monthly, in 1984—his first job as a magazine editor. He went on to work at Time Inc., Life magazine, and The New York Times, where he served as ombudsman in the wake of the Jayson Blair plagiarism scandal.

He’s the author of numerous books, including Great Fortune, a 2003 history of Rockefeller Center that was shortlisted for a Pulitzer Prize.

In this episode, Okrent talks about his personal board of advisors and the roles they’ve played in his life, about his career highs and low—including a “humiliating” bake-off he was part of when Sports Illustrated was looking for a new editor, about how he introduced the world to fantasy sports, but didn’t make a dime, and how he later pivoted to fame and fortune “off” Broadway.

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