Moss is about to pack up his corner office in lower Manhattan. David Haskell -- who has worked at the magazine since 2007 -- will be taking his place at the end of the month.
Throughout his 15-year run as editor in chief, Moss has borne witness to the magazine industry's digital makeover and he's a fan of what's been happening.
"The business changed so much," Moss told CNN's Brian Stelter on this week's Reliable Sources. "And from my point of view it was just all opportunity."
Moss thinks that opportunity still exists. He said there's never been a more exciting time to be in the "storytelling" business.
Platform agnostic
"I don't think it matters whether you call this a magazine or a digital website -- they are all just ways to do what journalism has always done," he said.
"I think you have to be a little crazy to do this job," he said, and "I didn't have that anymore. I also kind of felt that it was 15 years. It's good for the organization to get new blood, or get a sense of rejuvenation."
He said he expected to have some regrets about exiting, but hasn't felt any yet. When asked what was the best thing about being editor, he compared it to childlike fun.
"You're like a kid in kindergarten," he said. "You're playing with a bunch of people and you're making something together."
Managing people
But, he said, the worst part of the job was being the boss.
"I have over the years just, you know, become less and less interested in like, the bossness, the management, all that kind of stuff," he said.
The walls outside Moss's office are lined with famous covers from New York magazine during his time. He said he takes particular pride in the 2015 Bill Cosby cover, with 35 of his accusers seated in rows; an Eliot Spitzer cover with a "BRAIN" label pointing to his crotch; and a cover after Superstorm Sandy showing lower Manhattan in the dark.
Over the years Donald Trump has been "on the cover more than any single individual," he said, because of Trump's stature in New York.
So Moss surely saw Trump's electoral victory coming, right?
"Absolutely not," he commented.
One cover Moss wished got more attention was for a story on the history of the hamburger.
"We made a cow out of hamburger meat, which is a great cover and it thoroughly grossed out at least half the people who saw the cover. There was a kind of life to it that is, I think, just great," he said.
Print covers now have a chance to go viral on the web. But emerging mediums, like social media, also came with new challenges.
"You just had to jump into businesses that you didn't yet understand and figure them out as you're going along," Moss said. "And that is exhilarating, but it was, you know, it sort of a took a toll on focus."
The magazine's parent company, he noted, "crossed the line where we were making more digital revenue than we were in print revenue several years ago. So that insulated us from some of the pain" other magazines have felt.
New York Media is owned by the Wasserstein family and run by CEO Pam Wasserstein. She recently considered a sale and other strategic options, but told staffers that the company "has decided not to move ahead with a sale," Dow Jones reported. CNN has not confirmed this detail.
One month ahead of his departure date, American Society of Magazine Editors announced that Moss is joining the Magazine Editors' Hall of Fame.
In the interview, he didn't express the kind of wistfulness for print that other editors might expect.
"Don't get me wrong," he told Stelter, "I love print and I will be a print reader forever." But, he said, "you can't look back. You really just have to see what is the opportunity. And there's so much good."
Thanks to the web, "you can reach more people now than you ever could before; you can find people; there's no distribution walls really at all; you can just reach anyone anywhere in the globe. You can tell stories with words, with pictures, with animated pictures, with sound, and there'll be all sorts of new things that will happen over the next 10, 20, 30 years. And I think you just have to embrace all those opportunities."
That same view came through when Stelter asked what advice Moss has for his successor.
"Make this your own. Forget about me," he said. "It would be a big mistake to try to be too reverential toward the past. And I think that media is always about what is next. What is new, what is next. "
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