Graydon Carter on Vanity Fair, Editing & a Short-Fingered Vulgarian Named Trump

Graydon Carter is the co-founder of Spy Magazine and Air Mail, and for 25 years, he was the editor of Vanity Fair. His memoir, When The Going Was Good, chronicles a time when the going was extremely good for glossy magazines and their star editors. During the golden age of magazines, Vanity Fair combined celebrity profiles with deeply reported journalism to great acclaim, and Carter, arguably, became more famous than many of his extremely talented writers. He and Kara discuss everything from office politics at Vanity Fair to Canadian politics, including President Trump’s (possible) descent into madness, the artistry involved in making a restaurant cool (as opposed to hot), and why anxiety is an essential ingredient for editors. Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:12Kara Swisher?

  Hi, everyone. From New York Magazine and the Vox Media Podcast Network, this is "On" with Kara Swisher, and I'm Kara Swisher. My guest today is Graydon Carter, the storied magazine editor who is best known for co-creating Spy magazine in the 1980s and being the top editor for Vanity Fair for 25 years. I met Carter-- well, I knew about Carter before I met him. He was obviously a legend in the magazine industry. And I worked for Vanity Fair for a very short time, largely to get an invitation to the Vanity Fair Oscar party, and that is why I did it, and that's the way it goes. But he was always legendary, always interesting raconteur. I've had many dinners with him, and just a very funny, interesting, and erudite person. Even before Spy, Carter was an early critic of then-real estate mogul Donald Trump. He

• 0:54Kara Swisher?

  wrote one of the first major profiles of him for GQ in the 1980s, and his criticism of the man he called "the short-fingered Bulgarian" was fitting then as it is today. Carter's work as both a writer and editor was never lacking in witty commentary. He helped define the voice of publications he touched, for sure, and he was possibly more famous than many of his famous writers. That voice and many, many other stories are the subject of his new memoir, When the Going Was Good: An Editor's Adventure During the Last Golden Age of Magazines. We're going to talk about that golden age and how he's transformed the print legacy into digital in his latest publication, Airmail. And our expert question this week comes from Carter's co-founder and co-conspirator at Spy, Kurt Anderson.

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• 3:57Kara Swisher?

  Graydon Carter, welcome. Thanks for being on ON.

• 4:00Speaker 06

  A pleasure. Always nice to see you.

• 4:02Kara Swisher?

  I know. You talk about your new memoir, When the Going Was Good, an editor's adventure during the last golden era of magazines, which I'd love to understand where it is right now from you, but we have a lot to talk about. So your memoir reads like a who's who of literati, journalism, even Hollywood. And thank you for naming me in your pantheon of reporters. I don't think I did very much for you, but I appreciate it.

• 4:25Speaker 06

  You're very entertaining, though, in meetings.

• 4:26Kara Swisher?

  I am entertaining in meetings. You have a lot of stories of your first meetings with various people. Do you remember how we met?

• 4:34Speaker 06

  I wrote to you, and I think you were doing the thing with Walt. And you came in, and usually I'm not a big one for meetings. And it was supposed to last, I don't know, five or 10 minutes just to say hello. And you stayed an hour and a half, and I thought it was a great hour and a half.

• 4:51Kara Swisher?

  Do you know what you said to me when I walked in?

• 4:54Speaker 06

  What?

• 4:55Kara Swisher?

  You said, "I'm gonna make you famous."

• 4:57Speaker 06

  I didn't say that. There's no way I said that.

• 5:00Kara Swisher?

  You did. You did. You were joking.

• 5:01Speaker 06

  Okay.

• 5:02Kara Swisher?

  It was very funny. But at the time, tech was a big deal, and you guys were sort of shifting into the idea of who's establishment and who's not. And you started to really start to pay attention to those people. I want you to talk a little bit about the beginning. You went from working on a railroad to editing a Canadian magazine to starting a Time magazine, which even by then was starting to see sort of edges to it. So talk a little bit about this trajectory.

• 5:30Speaker 06

  Well, I grew up in Canada, and we spent five years in Europe. And we came back. I was about six years old. And I loved growing up in Canada. It was really cold. And your life for seven months of the year revolved around skiing and hockey, both of which I loved. And I had no real notion of what I wanted to do. But I did love magazines because they brought the outside world into us. When I was growing up, my parents ascribed to Time and Life and The New Yorker, and later Esquire. And magazines do a certain thing. Newspapers tell you about the news of the past day or the past week. And magazines tell you about a time and place.

• 6:14Speaker 06

  And I love magazines. I devour them. And so, and when I was in, uh, my adventure on the railroad was basically, a lot of my parents' friends and my parents send their kids off west to, um, to toughen them up and get them out of their so-called comfort zones. And, um, I spent six months working as a lineman for the Canadian National Railway. And it was one of the greatest six-month periods of my life. I, I loved living in a boxcar on the Saskatchewan Prairie with a bunch of guys, many of whom had criminal records, but were otherwise really decent people and just got into a spot of trouble along the way. So then I come back and then I, um, I go to, I go to college and I stumble into this office

• 6:59Speaker 06

  where a bunch of kids were putting together a literary magazine and they'd gotten funding from the university and, uh, and office space from the university. And they, they said they were looking for an art director. I said, well, I can draw a bit. And they, so they made me the art director. And then one of the editor, the top editor left a year later and I became the editor. And it was, it consumed all my days. I, we, nobody knew what they were doing. But it, um, I, I was stuck at it for four years.

• 7:31Kara Swisher?

  Why editor and not writer necessarily? Though you're a very good writer.

• 7:35Speaker 06

  I'm not, um, I'm not as adventurous as most reporters. I, I don't, you know, I don't savor going to far corners of the world to bad republics and, um, and, and doing that sort of thing. I liked, uh, I liked the, the business of ordering a number of stories into a package that I hope would please a reader. And I, I love being an editor. So I've been an editor now for 52 years. And when I started, I was probably one of the youngest editors in the business. And at this stage, I'm probably one of the oldest editors in the business.

• 8:05Kara Swisher?

  And what do you think the editor does for the writer? Cause often, uh, writers are sort of made. And I know that, uh, various writers, uh, Brian Burrows, were talking about the impact you had on them as writers. What do you think your overall role was for them?

• 8:21Speaker 06

  Well, Brian would have been a star. He was a star before I, I took him on and he would have been a star without me. Editors serve a variety of functions. Some are great pencil editors. They're sort of copy editors. Some try to inspire the writer. And, you know, the job of the editors to sit you down, Kara, on Monday and say, the job, the assignment you're about to take on is the most important one of your career. And you're going to do the story, then you turn it in, and then me to sit down with you on a Monday or Tuesday, four months from now, and tell you the same story about the assignment you're going to take on then. So it was about trying to get the best out of people and treating them well. I think

• 9:05Speaker 06

  that you get much more out of people if you show appreciation for what they do, because being a writer is much more difficult than being an editor. So, yeah, that's what it is.

• 9:16Kara Swisher?

  Do you think, in today's times, when you think about it, you've since started Airmail, is there a point to editors now? They seem to be cutting them, and they don't occupy the same mind space, especially magazine editors?

• 9:29Speaker 06

  I mean, I suppose at some point, AI is going to replace them. But I think that the, I think you can tell a well-made, hand-built publication over something that was done through programmatic, you know, selection or some algorithm. It's not the same, because the algorithm won't find something that you didn't think you were interested in, and you wind up being interested in.

• 9:52Kara Swisher?

  All right. I want to go back to some of your early days. You wrote about one of your first cover stories of then-real estate up-and-comer Donald Trump in GQ in 1984. He and you have had quite a long experience together, ups and downs, essentially. It was called Donald Trump Gets What He Wants. Kind of a great headline. But let me, I'm going to read a paragraph for you, and I'd just love you to talk about it a little bit. Actually, why don't you read it?

• 10:18Speaker 06

  Yeah, I can.

• 10:19Kara Swisher?

  Go ahead.

• 10:20Speaker 06

  "The six-foot-two-inch frame is trim but well-nourished. The hands small and neatly groomed. The suit is blue and stylish, maybe a little too flared in the legs for someone who lives east of the Hudson." But the only thing that gives away this driver from an outer borough are his cufflinks, huge mollusks of gold and stone the size of half dollars.

• 10:40Kara Swisher?

  So you kind of nailed them right then, as an outsider, obviously to the Manhattan world, and you know, you, in a lot of ways, were outsider yourself, coming from Canada. Did you relate to Trump? Can you talk about that? And why you picked "well nourished"? I thought was my favorite word, the entire thing, although everyone focuses on the small hands, but talk a little bit about that story.

• 11:01Speaker 06

  Well, I spent three weeks with him, and this was his first bit of national exposure. And it was hard not to be somewhat charmed by him. He's not without his charms, and they're, you know...

• 11:12Kara Swisher?

  People don't get that part of him. He's actually very charming.

• 11:15Speaker 06

  Oh, no, he can be charming. And, you know, but I literally don't recognize the Trump I see on TV now. It bears no relationship to the man I met and man I knew over 40 years. He was transactional, and he was always on, you know, not to make, but, you know, looking for the advantage. But these, this sort of scattershot last two months are not what I expected at all. That he hasn't grown, he's not wiser, the way people get wise. You lose a lot of steps along the way as you get older, but he's the same man, and

• 12:00Speaker 06

  that's how I don't recognize him.

• 12:01Kara Swisher?

  Right, so talk about that original man, though. Where are the similarities? Because you seem to have nailed them pretty closely about what people think of him now. Little too flared, well nourished, small hands, like trying to impress. I mean, you sort of nailed every single critical aspect of this person. The cruelty, I don't think you have in there.

• 12:21Speaker 06

  He sent staff out to buy up all the copies of GQ on the newsstands in New York. Now, I think it was in part to get it out of people's hands so they wouldn't see it, and at the same time, so that it would seem like it was one of their best sellers of all time. And I think, strangely enough, years later, I was working for Cy Newhouse, who published Random House, owned Random House and Conde Nast, and he said that the sales of that GQ cover inspired him to...

• 12:50Speaker 06

  See, approached Trump to do a book and the book became The Art of the Deal and then The Art of the Deal led to The Apprentice and then The Apprentice led us to where we are now.

• 13:01Kara Swisher?

  It's all your fault.

• 13:02Speaker 06

  Yeah, one hundred percent. No, no, butterfly's wings and I liked him. I'll be honest. I thought I didn't want, I mean, we weren't chums or anything like that. When I became editor of Vanity Fair, he tried to bring me into his circle, but it couldn't hold.

• 13:18Kara Swisher?

  Now, the story is not a total takedown. It definitely has snark. Obviously, when you moved on to Spy Magazine, the magazine you co-founded with Kurt Anderson a few years later, Trump was part of the magazine's first cover story called Jerks, The Ten Most Embarrassing New Yorkers. Way to make a splash. I see what you did. I see what you did there. So, you and Kurt later famously dubbed Trump the short-fingered Bulgarian, which of course has stuck forever. So, talk a little bit about what the role for Trump and people like him played for you as an editor and what Spy meant in that regard.

• 13:50Speaker 06

  Well, New York had just come out of near bankruptcy or war bankruptcy in the 1970s and the 1980s was starting to build and all of a sudden, the city had this new influx of money and largely from investment banks, which had not really been a factor in the past. And there was a lot of money and the people who had the money weren't afraid to parade it, which is great for journalism. And so, it was like an ongoing daily Macy's Day parade floats. And Trump was one of those and people like Leona Helmsley and the ladies who lunch and it's the world that Tom Wolfe captured in.

• 14:30Kara Swisher?

  Bonfire of the Vanities.

• 14:32Speaker 06

  And so, and Trump was a, you know, he wanted to be out there. He was, you know, he'd be calling into the tabloids gossip about himself under an assumed name and he loved being a tabloid fixture. And this is when we had two very vibrant competitive tabloids, the Daily News and the New York Post. And he was very much the poster boy for those two tabloids.

• 14:55Kara Swisher?

  It was sort of the beginning of your very public, I would, some people could think it's a feud, you called it Enduring Love Fest in 2013, and you were interviewed about him for this 1991 documentary, let's, let's listen to what you said, I want to get an idea of what he represented versus what you were doing at Spy.

• 15:14Speaker 07

  The only end to this road is sort of ultimate madness, and you know, living alone in an apartment complex in Panama and growing your fingernails long and storing your urine in mason jars, he, he just, there's no other way, I mean, that or taking over the world, one or the other, it's either the most public life in the world or the most private at the end of this, there's no in-between, he's not gonna, you're not gonna catch him out, you know, with a Toro on a Sunday afternoon, cutting the lawn somewhere, it is, it's gonna be some, one extreme or another, either the greatest Bond villain of all time, or Howard Hughes.

• 15:48Kara Swisher?

  Well, that's very prescient.

• 15:50Speaker 07

  I might have got both rights, points right.

• 15:53Kara Swisher?

  Right, right, so talk a little bit about this, because revenge and retribution obviously have been major motivations for Trump, why did you think this at the time? Because you were right, pretty much, pretty much, well, the Bond villain part.

• 16:05Speaker 06

  Because I don't, you know, I can't ever see, I don't think I've ever seen a picture of Trump driving a car.

• 16:10Kara Swisher?

  He just bought one.

• 16:11Speaker 06

  Wait till you see it, see if he ever drives it, I don't think he can drive, and I think, I mean, the golf carts are one thing, but a three-year-old can drive a golf cart, and, but I don't, I don't think he's probably ever done anything that a normal father has done at his age, I think he's a very good family man, I think that, that, he is that, but he, he's just a kind of a unique person, and I thought, I was sort of being glib in this interview, but it.

• 16:40Speaker 06

  I think he had larger aspirations than most people gave him credit for.

• 16:45Kara Swisher?

  Yeah. Do you think your tax setting to do with creating the person he is today? I mean, he loves giving people nicknames and you certainly were good at that. Do you have any, do you feel any like that you helped make him even by villainizing him in some fashion?

• 17:00Speaker 06

  Well, his nicknames are so clumsy and sort of un-literate. Always were clever and so I don't take any credit for that. I think it's those are the typical things a schoolyard bully does. And I think that how masculine is it to whine all the time? To bully the little guy and to treat women as non-equals? I, that's not in any dictionary in the world under the definition of masculinism. And it's, I'm talking about the sort of the overall encroaching bro culture, which I hate.

• 17:37Kara Swisher?

  So what do you make of his calls on his, I'd ask you as a Canadian to annex Canada? And now Carney, the Prime Minister is making hay of it. Is actually, he looks like he may win and beat the Conservative because of it. What do you think about it? I'm not going to blame you for it, calling him short-fingered Bulgarian as a Canadian. But what do you, what do you think about what's happening there? And also the snap elections that Mark Carney just called?

• 18:01Speaker 06

  He's done wonders for liberal democracies around the, around the world. And in terms of unifying them and making the, the left of center wing of their politics rise. I mean, the Liberal Party in Canada was in deep trouble six months ago. And Mark Carney, first of all, Mark Carney is, he's handled people like this for decades in his job. He's so smart. He's got a wonderful dry sense of humor. I don't know him well, I've met him once. And, but I admired him from afar. And I think that he will, Trump would be wise to be cautious of this man when he, if he gets into the same room over a negotiation. And the fact of the, similar fact of the matter is Canadians don't want to be Americans. They like being Canadians.

• 18:47Speaker 06

  And I'm not sure how he thinks this is going to happen, but if it involves if it involves a hanging in the way of troops, um, he should not do it in the wintertime because the Canadians are really good in winter and they're strong on ice and they can handle the cold.

• 19:03Kara Swisher?

  Do you imagine it could happen? This could actually happen?

• 19:06Speaker 06

  No, I don't know. I don't understand what the end game is here.

• 19:10Kara Swisher?

  Well, 51st day.

• 19:11Speaker 06

  No, no, that's, that's like saying, you know, I'd like to take your house without paying for it. And, and I just don't see it happening. I could, you know, maybe, I mean, the Panama situation may be different, but I don't see Greenland or Canada happening.

• 19:24Kara Swisher?

  Mm hmm. And would you have any idea why he wants to do this from how many of the years of observing him?

• 19:31Speaker 06

  Because I think he loves to flood the headline zone. You'll, you know, since he's been elected, there, you know, all these executive orders and everything like that. So if you pick up a copy of the Times or the Journal in the morning, he's in, he's in a half dozen, sometimes a dozen headlines. And that I think he likes. Also, I think if you just spray the, the, the populace with all these changes and these, some of these crazy ideas, they lose track of what's actually important.

• 20:00Kara Swisher?

  Um, one last question about Trump. Uh, in the GQ article, you also mocked his suit. Suits are a big deal to you. You write a lot about the ones you bought. You're Taylor in London. Um, do you have any thoughts about what he did to Ukrainian President Vladimir Zelensky for not wearing a suit? And I'd love to know what you think of Elon's getup, baseball hat, black shirts.

• 20:19Speaker 06

  Well, I mean, first I thought that that meeting in the Oval Office was absolutely atrocious. And, um, that's Zelensky's look. I mean, Churchill visited Roosevelt during the war, wearing his sort of, um, his jumpsuits during the war. Um, I mean, this is a man who's been, you know, at, at war for the last, you know, two years or so. And I thought, I thought J D Vance was even worse. I, I thought he, his behavior was appalling. And as for Elon Musk, I mean, he did, it's, that's not a good look for a man, looking like a, um.

• 20:51Kara Swisher?

  Lesbian. I say he looks like a lesbian I used to date in the 1980s.

• 20:56Speaker 06

  Yeah, no, like a heavy metal loving lesbian.

• 20:58Kara Swisher?

  Yeah. We'll be back in a minute.

• 21:12Speaker 01

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• 24:16Kara Swisher?

  So I want to shift gears a bit to get back to your career in the magazine industry. There's so much going on right now, but let's go backwards a little bit. Every interview, we have someone call in with a question. Have a listen to this one.

• 24:27Speaker 08

  I'm Kurt Anderson, and I met Grayden 44 years ago when I came to Time Magazine as a writer. And five years later, we launched Spy Magazine together. And my question, Grayden, is this: if we hadn't started Spy, or if instead of creating the most important, beloved, enduringly influential new magazines of its era, it had just fizzled out right away, how do you think your life would have proceeded? Would you stay a writer, stay an editor, try to start another publication, go on into show business? What?

• 25:07Speaker 08

  Or maybe, spitballing here, going back to Ottawa, got your college degree, become the prime minister's press secretary, and started a retro 1950s, 60s-style restaurant chain called The Deefen Bakery that specialized in butter tart bars and beaver tails? But seriously, what is your career path, do you think, absent Spy?

• 25:35Speaker 08

  Congratulations on the book and see you soon.

• 25:39Kara Swisher?

  For people don't know, Deifan Baker was a Prime Minister of Canada. Kurt's making a Canadian joke.

• 25:44Speaker 06

  Oh, God. That's impossible to answer. I think, because I couldn't have stayed at Life magazine, because where I was at the time, because I just wasn't going anywhere there. I probably would have become, I had a decent little side career as a writer for magazines. I mean, Kurt would have gone on to far greater things than I would have. But I probably would have, you know, I would have been open for business to do almost anything. I would have written for magazines and then, I don't know. But I'd probably somehow find a way back into editing.

• 26:15Kara Swisher?

  So you left Spy after a brief interview for the New York Observer before being tapped by Cy Newhouse, who became editor of Vanity Fair. And one of the reasons you left Spy was the new owners started meddling editorial. You talked about it. You say Cy didn't, for the most part. You call him the great billionaire proprietor. I want to talk about those different approaches of owners and how they affected your work. Talk a little bit about what happened at Spy and then what Cy Newhouse did that was different.

• 26:40Speaker 06

  Well, Spy, so Kurt Neitz and our partner, Tom Fellows, we sold it to Johnny Pagazzi and Charles Saucy. And as is their right, they wanted certain people on the cover and they wanted us to do this and they wanted us to do that. And it's one thing editing this magazine when you co-founded it, and it's another thing to be under the thumb of somebody else. I'm still very close to Johnny Pagazzi, but it just didn't work for me. And I had this idea for a twice-weekly newspaper that would focus on all the professional aspects of New York City life. And I was going around trying to raise money for it. And this man, Arthur Carter, who owned the New York Observer, he said, why don't you come and take this over? So I did that for a year. And that was a great experience. I

• 27:24Speaker 06

  absolutely loved the job. I loved the people I worked with. I thought I can get this to become a thing. And I had a six-month and a 12-month and an 18-month plan. And by about the six-month, things were starting to gel. And I started sending comp copies to friends of mine in Europe who were editors over there. And because other people were starting to read it. And my focus was on Greenwich Village and the Upper East Side of New York.

• 27:50Speaker 06

  And so Psy, I didn't know this at the time, he would make twice yearly visits to all his properties in Europe and he'd stop off in London and Paris and Milan. And he comes back, he sees copies of the New York Observer and all his editors in baskets. And he comes back thinking this is some huge international success. And he called me and says, would you like, um, could you would like to have a conversation? And so I go to his apartment, um, about a week later, I was very nervous. I was nervous because I thought he was going to offer me something like GQ or Details, which I, I knew I would not be able to do a very good job of. And also was very happy where I was. I wasn't making much money, but I was really happy doing the job.

• 28:34Speaker 06

  And so anyway, he, he got right to the chase, to the chase and he said, uh, would you, um, I've got two magazines and wonder if you'd be interested in either of them. He said, The New Yorker and Vanity Fair. And I almost choked. And so we, um, we, we talked for a while and I, I said, I explained to him that we'd made such fun of Vanity Fair when we were at Spy that that might be a bit difficult. And he said, okay, it's The New Yorker. And then obviously, you know, Tina Brown, who had far greater, uh, seniority at Conde Nast, said, you know, she, she, she decided that she wanted to be the editor of New Yorker and I, I couldn't blame her for that. And so the day before this was to be announced,

• 29:14Speaker 06

  um, Anna Wintor called me and said, it's going to be the other magazine, that is to say Vanity Fair. And so, but act surprised when Psy calls you. So after we decided on The New Yorker, I'd worked on a six month, 12 month, 18 month plan of what do I do to change The New Yorker and would not be in dramatic, uh, shape in any way. Um, and more, uh, just slow sort of, um, changes.

• 29:40Kara Swisher?

  Tina seems to have a different take on the Vanity Fair and New Yorker story. She told the New York Times, your name didn't come up to her among the names of possible candidates.

• 29:47Speaker 06

  No, I think actually, no, I saw that. Actually, both stories can be true because, uh, Psy never discussed, um, editorial changes with other editors. So, um, he might've been confided with Anna, because I think she was his closest confidant. Um, no, I think, I, I understand her, her point of view, but I know that what my story is, is correct as well. But I had no plan for Vanity Fair, but I didn't think Psy would pay me unless I was actually at the wheel. Um, driving the magazine. So I started about a week later and it took me a full two years to, you know, fully get my, my little feet under the table and to get issues pulled

• 30:30Speaker 06

  together that, that I wanted rather than just things I could, I could get my hands on.

• 30:35Kara Swisher?

  So it was a job you didn't want, but got anyway, essentially.

• 30:38Speaker 06

  It's not that I didn't want it. It's just that it surprised me and, um, and then I, and it, and after the two-year period, this is a long period in, in, you know, I wouldn't bring my kids into the office because it was so poisonous. Everything changed one day. I got rid of three of the troublemakers. I didn't fire anybody for two years and I got rid of three of the people who had been left behind who were troublemakers. I did that all in one week. That was more people than I'd fired in my lifetime and things changed and I wanted, because I like a, a, I like a collegial, convivial office with very little drama. Um, there's enough drama, you know, out on the streets of New York to, rather than having it in your, your actual office. And so I, you know, all of a sudden

• 31:21Speaker 06

  I could bring my children to work, my wife and I, my colleagues started saying please and thank you after, um, uh, discussions and it, it changed the whole, um, temperature of the office.

• 31:34Kara Swisher?

  So talk about the ownership though, because that's more important. I know you know about my bid to buy the Washington Post, which is not for sale, by the way. Um, mostly it's because I don't think Jeff Bezos is doing a good job staying out of the editorial process. I think he's turned into a bad owner from relatively okay one. Um, talk a little bit about what makes a great owner and what lessons you think like he and other billionaire media owners could learn from Cy Newhouse. There's Marc Benioff at Time, Lorraine Powell jobs at The Atlantic, who seems to be doing a pretty good job. Patrick Assunshong at the Los Angeles Times, who seems insane to me, allegedly. But, um, talk a little bit about ownership and what it means to be an owner. It, I know it's a different time and the money is, they're losing a lot of money and so there's a little different situation going on.

• 32:20Speaker 06

  Well, I mean, when you buy a media property, there's elements of public trust about it. It's not like you're buying a furniture factory. And Cy had his own unique way of doing things. A lot of people who did not know him thought of him as eccentric. And I suppose he did have his eccentricities, but he was also incredibly wise. So Cy had a policy of giving his editors all the elements, things they would need to be successful. If they failed, it was because of them, not because of him. He gave them all these things. And then he stepped aside. He would be there to counsel, and he had his own Socratic method of working through a problem. But he never, never interfered.

• 33:04Speaker 06

  And he would not say, please don't do a story on this person, or please do a story on this person. And he would not read magazines in advance of them coming out. So when Cy was making his rounds of, you know, dinner parties and that sort of thing before an issue of any one of his magazines came out, he could honestly say to anybody who asked, I have nothing to do with that part of the business. And so he just basically, he had trust in his editors. And if he felt the editors were not doing the proper job, he'd change them. But you don't want an owner getting too involved in the editorial process. I don't know of an instance, other than small magazines, where that works.

• 33:46Kara Swisher?

  How do you assess current owners like Bezos, for example?

• 33:51Speaker 06

  Well, he was heralded as a hero when he bought into it. And I don't know where he's getting his advice from, but just about every single thing he's done in the past year has served to weaken The Washington Post. I got a subscription offer the other day, I think it was like...

• 34:11Kara Swisher?

  They're gonna pay you?

• 34:12Speaker 06

  It was like $10 for a year. And I thought, okay, that's not a business anymore.

• 34:17Kara Swisher?

  Right.

• 34:17Speaker 06

  And whereas the, you know, Wall Street Journal is like $400 for, uh, for the year. And I just think, um, I, I don't follow the LA Times closely enough, uh, but I think that, um, staying out of editorial matters is important. And I think he's, I don't know Will Lewis, but I have a feeling that his days should be numbered because it has not gone well for, um, for, for Jeff on, on this. And I, you know, uh, too bad he can't bring back Marty Baron, who was-

• 34:45Kara Swisher?

  Right, right. Well, he's had, Marty's sort of burned that bridge with that piece he wrote, I think.

• 34:49Speaker 06

  If I was Jeff, I would suck it up and see if I could bring him back.

• 34:52Kara Swisher?

  Well, he, he needs both a CEO and an editor.

• 34:54Speaker 06

  Right.

• 34:55Kara Swisher?

  Um, so when you think, um, one of the things that's important, obviously, for creating buzz around an editor, um, is, is a big story. And speaking of the Washington Post, your book opens with the story Vanity Fair revealing Mark Feld as Deep Throat, Woodrow Bernstein's informant for the Post Watergate story. It's a really interesting story, and I really appreciated that you wrote about your nervousness. If you are right, I've, oh, I've been in those moments more times than I can count. Talk a little bit about why that was important for your tenure there.

• 35:24Speaker 06

  I mean, in the scope of things, it's not, it wasn't, you know, seismic. In the moment of the contemporary culture of it, it was seismic. And it started like two years beforehand. Also, it goes to the fact that because of we felt secure enough at Vanity Fair, we could play long games on certain stories. And this one, it took, uh, uh, probably close to two years to, to pull together. I got a phone call from a lawyer who said that he represented the man who was Deep Throat. And this was in 2003. I used to take any phone call from any reader or any, anybody that, just in case there was a, a lead on a story. And so I assigned an editor to talk to him further. And after about six months of, of

• 36:08Speaker 06

  talking, we had a name, and the name was Mark Feld. And I had never heard of him, and nor had the editor, David Friend. But we thought, okay, let's, let's, let's proceed with this. And so-

• 36:20Speaker 06

  There were issues here, there were problems were here that first of all, the Mark Feld, he was in his 90s, suffering from dementia and had told only a few family members that he in fact was the basis for Deep Throat. And so this went on for two months and we weren't 100% sure that it was him. And anyway, we close the story. I get married, I go on my honeymoon and I'd forgotten all about this, the story. And we were in the airport in Nassau on our way back. I didn't even own a cellphone in those days. And David Friend called and I thought, oh my God. And we were waiting to see what Bob and Carl would say.

• 37:01Kara Swisher?

  Right.

• 37:02Speaker 06

  And while we were closing it, I could have called Carl because Carl was on our masthead, but I thought he would then immediately call Bob and Bob would get it in the Washington Post the next day. And if I called Bob, the same thing would happen. And here we were, a monthly magazine, it wouldn't be on the newsstands for another three weeks or so. And so anxiety took over. I'd been, we'd been anxious about the story for the past six months because we weren't 100% sure, we were 96% sure, or 55% sure. And so my wife had an old flip phone and it was, the battery was going dead and I was praying that I'd hear what Bob and Carl had to say about this. And just before we got on the plane, they made an announcement and said, yes, Mark Feld is Deep Throat.

• 37:47Speaker 06

  And I remember giving the phone back to my wife and, you know, just tears welling up in my eyes, both from happiness but also just extreme relief.

• 37:58Kara Swisher?

  Anxiety, anxiety. Well, this is kind of, as you talk about, you were, you were very anxious to the whole thing and it is anxiety producing and there is, there is a through line of anxiety in your memoir. You call yourself a wobbly steward of Vanity Fair during your early years. You write about constant fear of being fired. You also write about the anxious editors are good editors. How would you talk a little bit about this? Does it make you a better editor? And you also wrote that worthwhile, a worthwhile professional life is built over the boneyard of failures. The trick is to keep them minor to figure out what, what went wrong and why. You also write that a failure can be, become a thinking field for years. Just make sure something good comes out of all of that stewing and worry. So talk a little bit about the idea of anxiety and failure.

• 38:41Speaker 06

  Well, I mean, I do think if you, I have a feeling that even Johnny Carson, who had did the Thai show every night for decades, that he would get anxious before going onstage. And I remember reading that Laurence Olivier, even Laurence Olivier would get anxious before going onstage. So I think that complacency would be the enemy of quality and anxiety is, is the friend of doing something well because through anxiety comes a constant need to try to be better than you actually are. And I'm anxious before I start writing a story. I'm anxious before I edit a story. I'm, I wish I wasn't this way, but I am.

• 39:22Kara Swisher?

  So was there one thing that you, a failure from those early days that you remember?

• 39:26Speaker 06

  I had this college magazine that caused me to be thrown out of school. I'd spent so much time on it. And I'd had it for five years and it was neither, it didn't really have a point. It was a literary political magazine. It wasn't all that far left and it wasn't far right. It wasn't all that highbrow. It wasn't lowbrow. It was just a magazine put up by a bunch of college kids who didn't know what they were doing. And when it, I sold the assets to our closest competitor, but I came out of it knowing that whatever you do, you, the thing you do, it has to have a point. And using that as guidance

• 40:08Speaker 06

  along the way, it's had a big effect in my career. When we had a restaurant in New York, the Waverly Inn, which we took over.

• 40:17Kara Swisher?

  I've been there with you.

• 40:18Speaker 06

  There you go. So when we took that over 20 years ago, there were very few American food, comfort food restaurants in New York and in the Village, very few banquet type restaurants, very few with white tablecloths and with low lighting. And so the restaurant had a point and it's, it continues to do well. And with Spy, Kurt and I cooked up a magazine that did have a point. It was going to be a magazine of funny, reported journalism about the central figures of.

• 40:50Speaker 06

  New York at the time.

• 40:51Kara Swisher?

  So having a point, it got you to have a point when you didn't have a point before.

• 40:55Speaker 06

  Yeah, if you have a point, you'll you have a better chance of success.

• 40:59Kara Swisher?

  Success. So speaking of that, one of the things you were Vanity Fair for 25 years, you launched a number of signature products. You were always innovating, which I thought was interesting. Features, live events, you had the Hollywood issue, the Vanity Fair Oscar Party, obviously, the new establishment issue and summit where you'd showcase emerging inventors and entrepreneurs. Walt Mossberg and I were in there. We also ran a conference that you kind of did one like, which was fine, which was fine by us. We don't mind. Flattery. So.

• 41:25Speaker 06

  We need copy from the best, Karen.

• 41:27Kara Swisher?

  I know. Thank you. Thank you. It's no problem. We continued. Talk a little bit about being innovative as a magazine, because people don't think of magazines as innovative, really, in many ways.

• 41:37Speaker 06

  I mean, we, I didn't think of these as innovations. I thought of them as sort of organic extensions of the magazine, and not all were my ideas. Some of them I went kicking and screaming on. And but it they did expand the magazine's sort of cultural footprint in terms of whether it's the Hollywood issue and the Oscar Party or the the new establishment summit we did in San Francisco. But then we also did, we I did a an annual dinner and party with Mike Bloomberg around the Buenos Correspondence Dinner. And, you know, a social life was a part of what Vanity Fair was in the in the day. And I think it was I think

• 42:19Speaker 06

  it was important. And I think that also it made it fun for the staff because every year the Oscar Party say I would take probably, I don't know, 15 or 20 of the writers out there and have them come to the Oscar Party. And I think that was sort of a great sort of bonus for all of them.

• 42:34Kara Swisher?

  Definitely. It's the only reason I wrote for you. So when you talk about the golden age of magazines, you didn't mention money. And it was the Gilded Age, really. And you do write about the expense accounts at Conde Nast, no bottom, no ceiling. You flew a correspondence all over the world, all expenses paid. You put Dominic Dunn up at the Chateau Marmont for months when he was covering the OJ Simpson trail, probably money well spent. Conde gave out interest-free loans for apartments, leased cars. Writers given weeks, months to write. Brian Burrow wrote a review of your memoir titled Vanity Fair's Heyday: I Was Once Paid Five Figures, Six Figures to Write an Article, Now What? Talk a little bit about what this was and why and what you think it is now.

• 43:17Speaker 06

  Cy was a very generous employer, but he wasn't throwing money out the window just to throw it out the window. He knew that it took money to create the magazines that he loved. And when he took over Conde Nast in the 1970s, it was the third-tier publisher. There was Time Incorporated that came first, Hearst came second, and Conde Nast came third. It was largely a magazine or company of finishing school magazines. And so he, through acquisitions and through startups and relaunches of magazines, he built it into the number-one magazine company. He spent money on his editors and the photographers

• 43:57Speaker 06

  and writers because he wanted them to be the best he could get his hands on. And they were extreme, but at the same time Kurt and I did Spy on a shoestring, and I did The Observer on a shoestring. Digging on a shoestring or having all the resources you could humanly imagine, it didn't take away. Both jobs were fun.

• 44:18Speaker 09

  We'll be back in a minute.

• 44:30Speaker 09

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• 45:41Speaker 02

  Support for the show comes from TikTok. There is a scientifically documented correlation between listening to podcasts and curiosity. So since you're here, you probably enjoy discovering new things. One great place to indulge your curiosity is TikTok. Whether it's how to forecast volcanic eruptions, strange phenomena that the James Webb Space Telescope picked up near the beginning of time, or a literal deep dive on the ocean's deepest reefs. TikTok has a wealth of fascinating videos just waiting to be discovered. Your next discovery is waiting on TikTok. Learn more at tiktok.com/discovermore.

• 46:25Speaker 03

  I'm Josh Mucio, host of The Pitch, where startup founders raise millions and listeners can invest. For our sweet season 16, we're giving you more of what you love and less of what you don't.

• 46:36Speaker 10

  I definitely start to blank out when we're talking about like middleware AI wrappers.

• 46:41Speaker 03

  Software is out. Actual cool stuff is in. We've got consumer brands. We're building Eight Sleep for daytime. Hardware that helps blind people see. They kept asking for middle finger. Next thing we knew, we had like 10 students running around flipping each other off. We've got deep tech to change the weather.

• 46:58Speaker 04

  Our big vision is to make it rain and snow on demand.

• 47:02Speaker 11

  What if you wanted to not make it rain somewhere else? Like one day, we're just like, screw Arizona.

• 47:09Speaker 03

  And dairy?

• 47:11Speaker 05

  I never imagined my life journey would be milk.

• 47:13Speaker 03

  Season 16 of The Pitch is out now. Listen wherever you get your podcasts. This season is presented by Engine.

• 47:22Kara Swisher?

  Ad revenue for print magazines was reportedly more than $19 billion at the peak in 2007. In 2023, it's $6 billion for both print and digital. You were scaling back print publications when you were at Conde Nast. And when I did an interview with Roger Lynch, he told me that Conde Nast is no longer a magazine company.

• 47:43Speaker 06

  And if Conde Nast is no longer a magazine company, what does that mean?

• 47:46Kara Swisher?

  I don't know. I don't, I want to know, what do you think it means?

• 47:49Speaker 06

  I have no idea.

• 47:50Kara Swisher?

  It's a content company. I believe that's what he meant.

• 47:53Speaker 06

  Multi-platform.

• 47:54Kara Swisher?

  Multi-platform, multi-platform, omnimedia. Martha Stewart was right all along. But talk a little bit about how you look at the, what magazines are now. There seems to be a little resurgence in some print magazines, but what do you overall think about the magazine industry? Obviously, the downscaling has happened rather substantively.

• 48:12Speaker 06

  Well, the good ones are still in pretty great shape. I look at the magazines we get in here, and at The New Yorker, The Atlantic, New York Magazine, The Economist, we've got Private Eye from, from England and World of Interiors, and you would never know there was recession with, with some of these magazines. With the exception of the English papers, magazines, they have great, they're great online experiences. So I think that, you know, certain types of magazines will do well, and a lot of it depends on the, the editors. I think it's harder now, but it, it's easier, it's an easier way of entry if you're a writer or photographer. In the past, you had to know, you know, the editor

• 48:56Speaker 06

  of a magazine to get a job or to get your work in that magazine. Now you can just put it on the internet, and if you can get noticed and if your work is good, maybe you can make a living out of it. But nobody ever went into journalism for the money. They went into it for the, the exhilaration, the desire to do good work, have an interesting life, and maybe make a bit of money.

• 49:19Kara Swisher?

  When you launched Airmail, which is a digital weekly, it's filled with a lot of voice. You have things like the Attention Whore Index, where readers can vote for most egregious attention seekers of the week. What were you going for? And how do you run it differently? Like, what do you, you know, obviously don't pay people six figures, et cetera. What is the thought when you were starting that and why?

• 49:39Speaker 06

  Well, we were living in the south of France, and I read all the foreign papers. And I thought, I thought I could put together a package of stories about both Europe and America that I thought would interest people. I didn't want to be on the hourly news cycle, and I didn't want to run anything that large. But I thought I could do it if I delivered something on Saturday morning when people sort of are tired of the news cycle and the horrors of the outside world. Something that looked as close to a magazine as humanly possible, and I think Airmail does that. And I had a great partner in Alessandra Stanley. We worked together at Time Magazine forty odd years ago. And my friend Jim Kelly was their books editor. And everybody else is in their twenties, pretty much.

• 50:21Speaker 06

  And so we call it has-beens and rookies. It's one of the great joys of my life to be able to continue doing this.

• 50:28Kara Swisher?

  And what's your goal in this?

• 50:30Speaker 06

  The goal in this is, what do you mean the goal? The goal for Airmail?

• 50:34Kara Swisher?

  Yes, exactly.

• 50:35Speaker 06

  For it to succeed and thrive. It'll never be as big as the New York Times, but I think it can carve its own path. We have the lane almost all to ourselves, and it will just survive beyond me.

• 50:50Kara Swisher?

  So you're known as the advantage here, obviously. The reality is you've always had a lot of fires burning. We talked about Waverly Inn. You've had other restaurants in New York as well. You've made film documentaries. You won an Emmy at a Peabody. You produced a Broadway show with Bob Mettler. Now you have Airmail newsstands in New York, London, and Milan. Is there something you wish you had, a project that you did and wish you had it? And what about what you'd like to do? Do you think you have enough?

• 51:16Speaker 06

  I do love having the bricks and mortar. I love our shop and down in the Village. And we probably will open one in the Brentwood Country Mart at some point in the future in Los Angeles. No, I think we've done, the nice thing is, we just, it's fluid enough that if we come up with an idea for something, for instance, I wanted a pen for when people were traveling this summer to separate them from the hordes, and it's this right here.

• 51:42Kara Swisher?

  Didn't vote for him. Back to Trump, yeah.

• 51:45Speaker 06

  You put that, and so I think it'd make it a little easier when you're traveling around and you talk with an American accent, especially in Europe right now, or in Britain. So, you know, come up with the idea, design it in a day, and three weeks later, we have them in the shop, and they're, we had 500 made, they were sold out in three or four days. So now we can constant reorder.

• 52:06Kara Swisher?

  Do you think of yourself as an entrepreneur?

• 52:10Speaker 06

  No, I think I was myself was just sort of open for ideas and willing to dive in and not be afraid to make a complete fool of myself.

• 52:19Kara Swisher?

  At the end of the book, you have a bunch of life lessons, like avoid the wall of fame. By the way, you had Donald Trump's mean tweets framed and hung on the wall outside your office.

• 52:28Speaker 06

  Yeah.

• 52:28Kara Swisher?

  I guess I could do the same for Elon. I used his hate tweets as blurbs for my book. I'm just wondering, when you think about the life lessons right now for people that are thinking about being in journalism, what would you imagine to be some of the most important of those that you've done?

• 52:49Speaker 06

  Well, as I say, I think the doors to entry into journalism are far more open now than they were certainly when I was younger. But at the same time, only if you want to have a long, long shelf life and make a life living out of this and, you know, maybe have children and raise a family, equality will always win. It's a slower build, but it's a more lasting build. I mean, there's, you know, there are things you can make. There are flash in the pan things that can fade quickly. And in the restaurant business, for instance, it's the hardest thing is to go from being a hot restaurant to a cool restaurant. Hot restaurants often last for about 18 months and then they just disappear because they're

• 53:34Speaker 06

  no longer hot. But to make the transition from hot to cool, and the same thing can be applied to anything on the internet, that is where the artistry lies.

• 53:42Kara Swisher?

  So my last question, where do you think the Trump story ends?

• 53:46Speaker 06

  Mason jars in Haiti or Guatemala. I'll cut it on, you know, that's too depressing to think of.

• 53:58Kara Swisher?

  All right. That's great. Graydon, thank you so much.

• 54:00Speaker 06

  Thanks so much, Kara.

• 54:06Kara Swisher?

  If you're in New York on Monday, April 7th, join me for a live taping of On With Kara Swisher with comedian Josh Johnson of The Daily Show. Josh is absolutely hilarious. The event is free and it's at Cooper Union's Great Hall, a beautiful and historic venue. Google Cooper Union and Josh Johnson to register for the event. On With Kara Swisher is produced by Christian Castor-Russell, Kateri Okum, Dave Shaw, Megan Burney, Megan Cunane, and Kalen Lynch. Nishat Kurwa is Vox Media's executive producer of audio. Special thanks to Claire Hyman. Our engineers are Rick Kwan and Fernando Aruda, and our theme music is by Trackademics. If you're already following the show, you know Canadians will win in a winter war. If not, go take your mason jar and hop on a plane

• 54:50Kara Swisher?

  to Panama. Go wherever you listen to podcasts, search for On With Kara Swisher and hit Follow. Thanks for listening to On With Kara Swisher from New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Monday with more.

• 55:08Speaker 01

  Support for the show comes from Engine. Running a small business means every dollar has to work hard, but if your team is still booking travel the old way, it's costing you more than you think. Engine is the fastest growing travel and spend platform in the country, built specifically for businesses like yours. Book a trip in as little as two and a half minutes, earn up to 10% back on hotels. And in 2025, Engine customers save more than $300 million on travel with zero booking fees, no contracts, and no BS. More than 1,000 businesses join Engine every month. Join them and get $500 when your business signs up and starts traveling at engine.com/vox.

• 55:52Speaker 02

  Support for the show comes from TikTok. There is a scientifically documented correlation between listening to podcasts and curiosity. So since you're here, you probably enjoy discovering new things. One great place to indulge your curiosity is TikTok. Whether it's how to forecast volcanic eruptions, strange phenomena...

• 56:14Speaker 02

  That the James Webb Space Telescope picked up near the beginning of time, or a literal deep dive on the ocean's deepest reefs. TikTok has a wealth of fascinating videos just waiting to be discovered. Your next discovery is waiting on TikTok. Learn more at tiktok.com/discovermore.

• 56:36Speaker 03

  I'm Josh Mucio, host of The Pitch, where startup founders raise millions and listeners can invest. For our sweet season 16, we're giving you more of what you love and less of what you don't.

• 56:47Speaker 10

  I definitely start to blank out when we're talking about like middleware AI wrappers.

• 56:52Speaker 03

  Software is out. Actual cool stuff is in. We've got consumer brands. We're building Eight Sleep for daytime. Hardware that helps blind people see. They kept asking for middle finger. Next thing we knew, we had like 10 students running around flipping each other off. We've got deep tech to change the weather.

• 57:09Speaker 04

  Our big vision is to make it rain and snow on demand.

• 57:13Speaker 11

  What if you wanted to not make it rain somewhere else? Like one day, we're just like, screw Arizona.

• 57:20Speaker 03

  And dairy?

• 57:22Speaker 05

  I never imagined my life journey would be milk.

• 57:24Speaker 03

  Season 16 of The Pitch is out now. Listen wherever you get your podcasts. This season is presented by Engine.