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

Summary

Podcast Summary: On with Kara Swisher – Graydon Carter on Vanity Fair, Editing & a Short-Fingered Vulgarian Named Trump

Introduction

In the March 27, 2025 episode of "On with Kara Swisher", host Kara Swisher engages in an in-depth conversation with Graydon Carter, the legendary magazine editor renowned for co-founding Spy magazine in the 1980s and serving as the top editor for Vanity Fair for 25 years. Carter also discusses his new memoir, "When the Going Wasan Editor's Adventure during the Last Golden Age of Magazines," and his latest digital venture, Airmail.

Graydon Carter's Career and Memoir

Carter opens up about his extensive career in the magazine industry, highlighting his early days and the trajectory that led him to become a pivotal figure in journalism. He reflects on his memoir, where he portrays the golden era of magazines and details the transition from print to digital media.

Notable Quote:

"I've had many dinners with him [Kara], and just a very funny, interesting and erudite person." (04:00)

Relationship with Donald Trump

A significant portion of the conversation centers around Carter's longstanding relationship with Donald Trump. Carter recounts writing one of the first major profiles of Trump for GQ in the 1980s, where he dubbed him a "short-fingered Bulgarian," a nickname that has endured over the years. He contrasts the Trump of the 1980s with the man he observes today, expressing surprise and disappointment at Trump's unchanged nature.

Notable Quote:

"He bears no relationship to the man I met and the man I knew over 40 years. It's... he hasn't grown." (11:13)

Transition from Spy to Vanity Fair

Carter discusses his departure from Spy magazine after its sale to Johnny Pagozzi and Charles Saatchi, citing editorial meddling by the new owners as a primary reason. He then narrates his journey to becoming the editor of Vanity Fair, a role he initially did not anticipate but embraced wholeheartedly. Carter emphasizes the changes he implemented to cultivate a collegial and drama-free office environment.

Notable Quote:

"I like a collegial, convivial office with very little drama." (29:56)

Ownership in Media and Conde Nast

A significant discussion revolves around media ownership, specifically Carter's views on Cy Newhouse of Conde Nast. Carter praises Newhouse's hands-off approach, trusting editors to maintain editorial integrity without interference. He contrasts this with contemporary media owners like Jeff Bezos, critiquing Bezos's involvement in editorial processes as detrimental to the integrity of publications.

Notable Quote:

"Cy had trust in his editors, and if he felt the editors were not doing the proper job, he changed them." (33:05)

Anxiety and Failure in Editing

Carter delves into the role of anxiety and failure in shaping a successful editorial career. He shares personal anecdotes, including the anxiety surrounding Vanity Fair's revelation of Mark Felt as Deep Throat, highlighting how high-stakes situations can drive editors to produce their best work. Carter asserts that anxiety fuels a constant need for improvement, preventing complacency.

Notable Quote:

"Anxiety is the friend of doing something well." (38:22)

Innovation and the Golden Age of Magazines

Reflecting on the golden age of magazines, Carter discusses the innovative features he introduced at Vanity Fair, such as the Hollywood issue, the Vanity Fair Oscar Party, and the Summit showcasing emerging entrepreneurs. These initiatives expanded the magazine's cultural footprint and fostered a vibrant community among staff and contributors.

Notable Quote:

"We thought Spy was going to be a magazine of funny reported journalism about the central figures of New York at the time." (40:10)

Current State of Magazines and Digital Transition

Carter evaluates the current landscape of the magazine industry, acknowledging the significant decline in ad revenue from $19 billion in 2007 to $6 billion in 2023. He observes that while print magazines face challenges, the best publications like The New Yorker, The Atlantic, and The Economist continue to thrive by offering exceptional content and robust online experiences. Carter emphasizes that editorial quality remains paramount for longevity.

Notable Quote:

"The good ones are still in pretty great shape." (46:06)

Launching Airmail

Transitioning to his latest project, Carter introduces Airmail, a digital weekly publication. He explains the inspiration behind Airmail—a desire to create a magazine-like experience that diverges from the relentless pace of hourly news cycles. Airmail aims to deliver curated, high-quality stories every Saturday morning, blending European and American content to engage readers seeking thoughtful journalism.

Notable Quote:

"It will just survive beyond me." (48:28)

Life Lessons for Aspiring Journalists

Towards the end of the episode, Carter offers valuable life lessons for those aspiring to enter journalism. He underscores the importance of having a clear purpose in one's work, noting that a defined mission increases the likelihood of success. Carter also highlights that quality content will always outlast fleeting trends, advocating for perseverance and resilience in the face of failures.

Notable Quote:

"If you have a point, you have a better chance of success." (40:14)

Conclusion

In closing, Carter shares his thoughts on the enduring impact of his work and the future of journalism. He remains optimistic about the potential of digital publications like Airmail to carve out unique niches in the media landscape. Carter's candid reflections provide a comprehensive look into the evolution of magazine journalism, the challenges of modern media ownership, and the personal experiences that have shaped his illustrious career.

Notable Quote:

"Quality will always win. It's a slower build, but it's a more lasting build." (50:43)

Final Thoughts

This episode of "On with Kara Swisher" offers a rich and engaging exploration of Graydon Carter's influential role in journalism, his nuanced relationship with Donald Trump, and his insights into the evolving media landscape. Carter's anecdotes and reflections provide valuable lessons for media professionals and enthusiasts alike, highlighting the enduring significance of quality editorial work amidst a rapidly changing industry.

Transcript

[Graydon Carter]

It's on.

[Kara 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's 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 poor spy. Carter was an early critic of then real estate mogul Donald Trump. He wrote one of the first major profiles for GQ in the 1980s. And his criticism of the man he called the short figured 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 in many other stories are the subject of his new memoir, when the Going Was 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, co founder and co conspirator at spy. Kurt Anderson. Support for on with Kara Swisher comes from arm. Have you ever wondered what's powering your smartphone and the other devices we interact with daily? Or what lies at the heart of life saving drug discoveries and robotic surgeries? The answer is arm. ARM technology is moving the world forward in enabling AI to create a more meaningful, more connected life for everyone everywhere. ARM believes the future isn't about technology. It's about people and the possibilities technology can offer us all. The future is built on ARM. You can discover [e-mail] Discover support for this show comes from Smartsheet. Have you ever wondered about all the incremental steps it takes to launch a rocket ship or maybe get a race car around a track or perform a life changing surgery? These feats of human ingenuity are executed by many people, taking many steps that lead up to one big goal, making the seemingly impossible possible. Whether you're organizing a team scaling a business or sending a rover across the solar system. Smartsheet is a work management platform that helps though all those details turn into One big leap. Smartsheet, the place where work flows. Learn [e-mail] box.

[Unknown]

Support for the show comes from the ACLU. The Trump administration is pushing a dangerous and sweeping attempt to control our bodies, our families, and our lives at the same time. A Supreme Court case this term could shape the future of bodily autonomy for all. Tennessee wants to take away transgender people's autonomy over their own bodies. They think the ruling that overturned Roe versus Wade allows them to do it. This would hurt everyone's freedom to control their bodies and lives. The government has no right to deny a transgender person the health care they need, just as they have no right to tell someone if, when, or how they start a family. The ACLU told the court that everyone deserves the freedom to control their bodies. Learn [e-mail] autonomy.

[Graydon Carter]

It is on.

[Kara Swisher]

Graydon Carter, welcome. Thanks for being on on a pleasure.

[Graydon Carter]

Always nice to see you.

[Kara Swisher]

I know you talk about your new memoir, when the Going Was 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.

[Graydon Carter]

I'm very entertaining, though, in meetings.

[Kara 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?

[Graydon Carter]

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 ten minutes just to say hello. And you stayed an hour and a half. And I thought it was a great hour and a half.

[Kara Swisher]

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

[Graydon Carter]

What?

[Kara Swisher]

You said, I'm gonna make you famous.

[Graydon Carter]

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

[Kara Swisher]

You did. You did. You were joking.

[Graydon Carter]

Okay?

[Kara Swisher]

It was very funny. But at Time, Tech was a big deal, and you guys were sort of shifting into the idea of whose establishment and who's not. And it was. 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 is starting to see sort of edges to it. So talk a little bit about this trajectory.

[Graydon Carter]

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. And when I was growing up my parents subscribed to Time and Life and the New Yorker and later Esquire. And magazines did us do a certain thing. They tell you, newspapers tell you about the news of the past day or the past week and magazines tell you about a time and place. And I love magazines. I devoured them. And so when I was in my adventure on the railroad was basically a lot of my parents friends and my parents send their kids off west to toughen them up and get them out of their so called comfort zones. And 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 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 go to college and I stumble into this office where a bunch of kids were putting together a literary magazine and they'd gotten funding from the university and office space from the university. And they said they were looking for an art director. I said well, I can draw a bit. And 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, I was stuck at it for four years.

[Kara Swisher]

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

[Graydon Carter]

I'm not, I'm not as adventurous as most reporters. I don't, you know, I don't say we're going to far corners of the world to bad republics and doing that sort of thing. I like the business of ordering a number of stories into a package that I hope would please a reader. And 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.

[Kara Swisher]

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

[Graydon Carter]

Well, Brian would have been star. He was a star before 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. The job of the editor is to sit you down, Kara, on Monday and say the assignment you're about to take on is the most important one of your career. And you're going 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 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.

[Kara 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.

[Graydon Carter]

I mean, I suppose at some point AI is going to replace them, but I think you can tell a well made hand built publication over something that was done through programmatic 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.

[Kara Swisher]

All right, I wanna 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 and Jiku in 1984. He and you have had quite a long experience together. Ups and downs. Essentially, who's 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 or actually why don't you read it?

[Graydon Carter]

Yeah, I can.

[Kara Swisher]

Go ahead.

[Graydon Carter]

The 6 foot 2 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. About the only thing that gives away this striver from an Outer burrow are his cufflinks, huge mollusks of golden stone the size of half dollars.

[Kara Swisher]

So you kind of nailed him right then as an outsider, obviously, to the Manhattan world. And you, in a lot of ways, were outside of 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 in the entire thing. Although everyone focuses on the small hands. But talk a little bit about that story.

[Graydon Carter]

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.

[Kara Swisher]

You know, people don't get that part of him. He's actually very charming.

[Graydon Carter]

Oh, no, he can be charming. And I, you know, but I literally don't recognize the Trump I see on TV now. He bears no relationship to the man I met and the man I knew over 40 years. It's. He was transactional, and he was always on. Not the make, but looking for the advantage. But 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 that's how I don't recognize him.

[Kara Swisher]

Right. So talk about that original man, though. Where are the similarities? Cause you seem to have nailed him 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.

[Graydon Carter]

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 at the same time, so that it would seem like it was one of their bestsellers of all time. And I think it strange enough, years later, I was working for Cy Newhouse, who published Random House, owned Random House and Connie Nast. And he said that the sales of that GQ cover inspired him to approach 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.

[Kara Swisher]

It's all your fault.

[Graydon Carter]

Yeah, 100%. No, no butterflies 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.

[Kara 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 the 10 most embarrassing new Yorkers. Way to make a splash. I see what you did there. So you and Curt lady 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.

[Graydon Carter]

Well, New York had just come out of near bankruptcy or 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 of floats. And Trump was one of those. And people like Leona Helmsley and the ladies who lunch, it's the world that Tom Wolf captured in Bonfire of the Vanities. And Trump was a. 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.

[Kara Swisher]

It was sort of the beginning of your very public. 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 listen to what you said that I wanna get an idea of what he represented versus what you were doing at Spy.

[Unknown]

The only end to this road is sort of ultimate madness. Living alone in an apartment complex in Panama and growing your fingernails long and storing your urine in Mason jars.

[Graydon Carter]

He just.

[Unknown]

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. You're not going to catch him with a Toro on a Sunday afternoon cutting the lawn somewhere. It's going to be one extreme or Another either the greatest Bond villain of all time or Howard Hughes.

[Kara Swisher]

Well, that's very prescient.

[Graydon Carter]

I might have got both rights points.

[Kara Swisher]

Right, right, right. So talk a little bit about this cuz 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, because I.

[Graydon Carter]

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

[Kara Swisher]

He just bought one.

[Graydon Carter]

I saw that. Wait till you see it. See if he ever drives it. I don't think he can drive and I think the golf carts are one thing, but a three year old can drive a golf cart. But 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 he is that. But he's just a kind of a unique person. And I thought I was sort of being glib in this interview, but I think he had larger aspirations than most people gave him credit for.

[Kara Swisher]

Yeah. Do you think your attacks had anything 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?

[Graydon Carter]

Well, his nicknames are so clumsy and sort of unliterate. Ours were at least clever and so I don't take any credit for that. I think 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. That's not in any dictionary in the world under the definition of masculinism. And I'm talking about the sort of the overall encroaching bro culture which I hate.

[Kara Swisher]

So what do you make of his calls? Obviously I have to 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 gonna blame you for it, calling him short fingered Bulgarian as a Canadian. But what do you think about what's happening there? And also the snap elections that Mark Carney just called.

[Graydon Carter]

He's done wonders for liberal democracies 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, but I admired him from afar, and I think that he will. Trump would be wise to be cautious of this man if he gets into the same room over a negotiation. And the fact of, the simple fact of the matter is Canadians don't want to be Americans. They like being Canadians. And I'm not sure how he thinks this is going to happen, but if it involves, if it involves anything in the way of troops, 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.

[Kara Swisher]

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

[Graydon Carter]

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

[Kara Swisher]

Well, 51st state.

[Graydon Carter]

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

[Kara Swisher]

And do you have any idea why he wants to do this from many of the years of observing him?

[Graydon Carter]

Because I think he loves to flood the headline zone since he's been elected, 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 a half dozen, sometimes a dozen headlines. And that I think he likes also. I think if you just spray the populace with all these changes and some of these crazy ideas, they lose track of what's actually important.

[Kara Swisher]

One last question about Trump. 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. Your tailor in London. 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 get up baseball hat, black shirts.

[Graydon Carter]

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

[Kara Swisher]

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

[Graydon Carter]

Yeah. No, like a heavy metal loving lesbian.

[Kara Swisher]

Yeah. We'll be back in a minute. Support for on with Kara swisher comes from NerdWallet. Folks, if you're anything like me, your day is a non stop balancing act. You've got things to do, places to be. And honestly, hunting for the best auto insurance deal is not exactly the top of the list. That's where the nerds at NerdWallet come in. They've already crunched the numbers so you don't have to. You want a lower auto insurance rate, right? But you've also got your life. You've got to write that speech for your friend's wedding, your new business to grow. And in between all of this, you've got to figure out when you're taking your dog to the vet. NerdWallet makes it easy. Answer a few quick questions and boom. Your best insurance match right then and there. Looks like you have the time to hit up the vet and grab a nice leisurely cup of coffee while you're out using your brain power on what actually matters. Smart. Letting the nerds use their brainpower on helping you find the right financial products. Genius. Get matched with lower auto insurance rates [e-mail] not all applicants will qualify for the lowest monthly payments. Nerd Wallet Insurance Services, California resident license number OK 92033.

[Unknown]

Support for the show comes from the ACLU. The Trump administration is pushing a dangerous and sweeping attempt to control our bodies, our families, and our. At the same time, a Supreme Court case this term could shape the future of bodily autonomy for all. Tennessee wants to take away transgender people's autonomy over their own bodies. They think the ruling that overturned Roe v. Wade allows them to do it. This would hurt everyone's freedom to control their bodies and lives. The government has no right to deny a transgender person the health care they need, just as they have no right to tell someone if, if, when or how they start a family. The ACLU told the court that everyone deserves the freedom to control their bodies. Learn [e-mail] Autonomy.

This episode is brought to you by 20th Century Studios. The Amateur when his wife is murdered, Charlie Heller, the CIA's most brilliant computer analyst, must trek across the globe and use his only weapon. His Intelligence to hunt down her killers and enact revenge. Starring Academy Award winner Rami Malek and Academy Award nominee Laurence Fishburne. The amateur. Rated PG13. Only in theaters April 11th.

[Kara Swisher]

So I wanna 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.

[Kurt Andersen]

I'm Kurt Andersen and I met Graydon 44 years ago when I came to Time magazine as a writer. And five years later, we launched Spy magazine together. And my question, Graydon, 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? Tried to start another publication? Gone into show business?

[Graydon Carter]

What?

[Kurt Andersen]

Or maybe spitballing here? Gone 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 Diefin B that specialized in butter tart bars and beaver tales. But seriously, what is your career path, do you think? Absence by. Congratulations on the book and see you soon.

[Kara Swisher]

For people who don't know Diefenbaker was a prime minister of Canada. Kurt's making a Canadian joke.

[Graydon Carter]

Oh, God, that's impossible to answer. I think because I couldn't have stayed at Life magazine, 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 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 know. Book, I don't know, but I'd probably somehow find a way back into editing.

[Kara Swisher]

So you left Spy after a brief interlude for the New York observer before being tapped by Cy Newhouse, become editor of Vanity Fair. And one of the reasons you left Spy was that 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.

[Graydon Carter]

Well, Spy, so Kurt, Nice. And our partner, Tom Felips, we sold it to Johnny Pagozzi and Charles Saatchi. And as is their right, they wanted certain people on the COVID They wanted to do this and want 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 Pagozzi, 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 take this over? So I did that for a year and that was a great experience. I absolutely loved the job. I loved the people I worked with. I thought I couldn't get this to become a thing. And I had a 6 month and a 12 month and an 18 month plan. And by about the 6th month things were starting to gel and I started sending comp copies to friends of mine in Europe who were editors over there because other people were starting to read it. And my focus was on Greenwich Village and the Upper east side of New York. And so psy was 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, could you like to have a conversation? And so I go to his apartment 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 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. And so anyway, he got right to the chase. He cut to the chase and he said, would you. I've got two magazines and wonder if you'd be interested in either of them. And he said, the New Yorker and Vanity Fair and almost choked. And so we talked for a while and I said, I explained to him that we 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 Tina Brown, who had far greater seniority at Conde Nast, said she decided that she wanted to be the editor of the New Yorker. And I Couldn't blame her for that. And so the day before this was to be announced, Anna Winter called me and said, it's going to be the other magazine, that is to say Vanity Fair, but act surprised when Cy calls you. So after we decided on the New Yorker, I'd worked on a 6 month, 12 month, 18 month plan of what do I do to change the New Yorker. And would not be in dramatic shape in any way. More just slow sort of changes.

[Kara Swisher]

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

[Graydon Carter]

No, I think actually, no, I saw that. Actually both stories can be true because Cy never discussed editorial changes with other editors. So he might have confided with Anna because I think she was his closest confidant. No, I think I understand her point of view, but I know that my story is correct as well. But I had no plan for. For Vanity Fair, but I didn't think Cy would pay me unless I was actually at the wheel driving the magazine. So I started about a week later. And it took me a full two years to fully get my feet under the table and to get issues pulled together that I wanted rather than just things I could get my hands on.

[Kara Swisher]

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

[Graydon Carter]

No, it's not that I didn't want it, it's just that it surprised me. And. And then after the two year period, this is a long period, I wouldn't bring my kids in 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. I like a collegial, convivial office with very little drama. There's enough drama out on the streets of New York rather than having it in your actual office. And so all of a sudden I can bring my children to work, my wife and my colleagues start saying please and thank you after discussions. And it changed the whole temperature of the office.

[Kara 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. Mostly it's. Cause 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 a relatively okay one. 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 Sy Newhouse. There's Marc Benioff at time, Lorraine Powell, jobs at the Atlantic, who seems to be doing a pretty good job. Patrick soon shong at the Los Angeles Times, who seems insane to me, allegedly. But talk a little bit about ownership and what it means to be an owner. 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.

[Graydon Carter]

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 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 for counsel, and he had his own Socratic method of working through a problem. But he never, never interfered. And he. 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. 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. He felt the editors were not doing the proper job, he changed 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.

[Kara Swisher]

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

[Graydon Carter]

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 he's every. 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.

[Kara Swisher]

I think it was like, they're going to pay you.

[Graydon Carter]

It was like $10 for a year. And I thought, okay, that's not a business anymore. Right. Whereas the, you know, the Wall street journal is like, $400 for the year. And I just think I don't follow the LA Times closely enough, but I think that staying out of editorial matters is important. And I think he's. I don't know Will Lewis, but I have a feeling his days should be numbered because it has not gone well for Jeff on this. And, you know, too bad he can't bring back Marty Baron, who was.

[Kara Swisher]

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

[Graydon Carter]

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

[Kara Swisher]

Well, he needs both a CEO and an editor. So when you think one of the things that's important, obviously, for creating buzz around an editor is a big story. And speaking of the Washington Post, your book opens with the story of Vanity Veer revealing Mark Felt as Deep Throat Woodward and 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 were right, 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.

[Graydon Carter]

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 probably close to two years to pull together. I'd gotten 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 anybody just in case there was a lead on a story. And so I assigned an editor to talk to him further. And after about six months of 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 proceed with this. And so 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 NASA on our way back. I didn't even own a cell phone 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, right? 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 newsstand for another three weeks or so. And so anxiety took over. We'd been anxious about the story for the past six months because we weren't 100% sure. We were 96% sure or 5% sure. And so my wife had an old flip phone and 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. And I remember giving the phone back to my wife and just tears welling up in my eyes, both from happiness, but also just extreme relief.

[Kara Swisher]

Anxiety. Anxiety. Well, this is kind of interesting. You talk about you were very anxious to the whole thing and it is anxiety producing and 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 fire. The anxious editors are good editors. I want you to talk a little bit about this. Does it make you a better editor? And you also wrote that a worthwhile professional life is built over the boneyard of failures. The trick is to keep them minor, to figure out what went wrong and why. You also write that a failure can 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.

[Graydon Carter]

Well, I mean I, I, I do think if you, I have a feeling that even Johnny Carson, who had did the Tonight show every night for decades, that he would get anxious before going on stage. And I remember reading the Lawrence Olivier, even Lawrence Olivier would get anxious before going on stage. 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 it never. I'm anxious before I start writing a story. I'm anxious before I edit a story. I wish I wasn't this way, but I am.

[Kara Swisher]

So was there one thing that you. A failure from those early days that you remember?

[Graydon Carter]

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 high brow. 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 I sold the assets to our closest competitor. But I came out of it knowing that whatever you do the thing you do, it has to have a point. And using that as guidance along the way. It's had a big effect in my career. When we had a restaurant in New York at the Waverly Inn, which we took over.

[Kara Swisher]

I've been there with you.

[Graydon Carter]

There you go. So when we took that over 20 years ago, there were very few American food, comfort food restaurants in New York in the Village, very few banquette type restaurants, very few with white tablecloths and with low lighting. And so the restaurant had a point, and 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 New York at the time.

[Kara Swisher]

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

[Graydon Carter]

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

[Kara Swisher]

Success. So speaking of that, one of the things, you were at vanny fair for 25 years, you launched a number of signature. 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 we only.

[Graydon Carter]

Copy from the best Carol I know.

[Kara Swisher]

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

[Graydon Carter]

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, but it, they did expand the magazine 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, I did an annual dinner and party with Mike Bloomberg around the White House. Correspondence dinner and a social life was a part of what Vanity Fair was in the day. And I think it was important and I think that also it made it fun for the staff because every year at the Oscar parties, 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, and I think that was sort of a great sort of bonus for all of them.

[Kara Swisher]

Definitely that'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 pay. You put Dominic Dunne up at the Chateau Marmont for months when he was covering the O.J. simpson trial. Probably money well spent. Conde gave out interest free loans for apartments, leased cars, writers giving him 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.

[Graydon Carter]

Sy 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 Connie Nast in the, 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 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, you know, Kurt and I did Spy on a shoestring and I did the observer on a shoestring. Doing it on a shoestring or having all the resources you could humanly imagine, it didn't take away. Both jobs were fun.

[Kara Swisher]

We'll be back in a minute.

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[Kara Swisher]

Oh wow, a real person.

[Graydon Carter]

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[Kara Swisher]

Well, I've got a complicated project.

[Graydon Carter]

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Hmm, I just might have to do more.

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[Kara Swisher]

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[Graydon Carter]

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[Kara 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.

[Graydon Carter]

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

[Kara Swisher]

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

[Graydon Carter]

I have no idea.

[Kara Swisher]

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

[Graydon Carter]

Multi platform.

[Kara Swisher]

Multi platform. Multi platform Omnimedia. Martha Stewart was right all along. Talk a little bit about how you look at 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.

[Graydon Carter]

Well, the good ones are still in pretty great shape. I look at the magazines we get in here and it's the New Yorker, the Atlantic, New York Magazine, the Economist. We get Private Eye from England and World of Interiors. And you would never know there was recession with some of these magazines. With the exception of the English papers magazines, they have 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 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 exhilaration, the desire to do good work, have an interesting life and maybe make a bit of money.

[Kara 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 the most egregious attention seekers of the week. What were you going for and, and how do you run it differently? Like what do you. You obviously don't pay people six figures, et cetera. What is the thought of when you were starting that and why?

[Graydon Carter]

Well, we were living in the south of France and I read all the foreign papers and 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 cyc, the horrors of the outside world. Something that looked as close to a magazine as humanly possible and I think air mail does that. And I had a great partner in Alessandro Stanley. We worked together at Time magazine 40 odd years ago and my friend Jim Kelly who's their books editor and everybody else is in their 20s pretty much. 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.

[Kara Swisher]

And what's your goal in this?

[Graydon Carter]

The goal in this is to. What do you mean the goal? The goal for Airmail?

[Kara Swisher]

Yes, exactly.

[Graydon Carter]

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 to survive beyond me.

[Kara Swisher]

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

[Graydon Carter]

I do love having the bricks and mortar. I love our shop and down in the Village, and we're. 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 pin for when people were traveling this summer to separate them from the hordes. And it's this right here.

[Kara Swisher]

I didn't vote for him. Back to Trump. Yeah, you put that.

[Graydon Carter]

And so I think it'd make it a little easier when you're traveling around and you talked with 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 had them in the shop and we had 500 made. They were sold out in three or four days. So now we on constant reorder.

[Kara Swisher]

Do you think of yourself as an entrepreneur?

[Graydon Carter]

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

[Kara 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. 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?

[Graydon Carter]

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 living out of this and maybe have children and raise a family. Quality 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, 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 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.

[Kara Swisher]

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

[Graydon Carter]

Mason jars in Haiti or Guatemala? Oh, gosh, I don't know. That's too depressing to think of.

[Kara Swisher]

All right, that's great, Graydon. Thank you so much.

[Graydon Carter]

Thanks so much, Kara.

[Kara Swisher]

If you're in New York on Monday, April 7, 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 Missell, guitarist Mary Yocum, Dave Shaw, Megan Birney, Megan Cunane, and Kalyn Lynch. Nishat Kirwa is Vox Media's executive producer of audio. Special thanks to Claire Hyman. Our engineers are Rick Kwan and Fernando Arruda 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 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.

[Unknown]

Support for the show comes from the aclu. The Trump administration is pushing a dangerous and sweeping attempt to control our bodies, our families, and our lives. At the same time, a Supreme Court case this term could shape the future of bodily autonomy for all. All Tennessee wants to take away transgender people's autonomy over their own bodies. They think the ruling that overturned Roe v. Wade allows them to do it. This would hurt everyone's freedom to control their bodies and lives. The government has no right to deny a transgender person the health care they need, just as they have no right to tell someone if, when, or how they start a family. The ACLU told the court that everyone deserves the freedom to control their bodies. Learn [e-mail] autonomy.