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

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 wrote one of the first major profiles for GQ in the 1980s, and his criticism of the man he called the short figure 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 Men May and 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. Support for On with Kara Swisher comes from Arm.
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Graydon Carter, welcome. Thanks for being on On.
A pleasure. Always nice to see you.
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 and your pantheon of reporters.
I don't think I did very much for you, but I appreciate it. You're very entertaining, though, in meetings.
I am entertaining in meetings. You have a lot of stories of your first meetings with various people.
Do you remember how we met? 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. Do you know what you said to me when I walked in? What? You said, I'm going to make you famous.
I didn't say that. There's no way I heard that.
You did. You did.
You were joking. Okay.
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 adding 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.

Well, I grew up in Canada, and we'd 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 do a certain thing.
Newspapers tell you about the news of the past day or the past week. And magazines tell you about time and place.
And I love magazines.

I devoured them. 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, I loved living in a box car 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 draw a bit and they so they made me the art director and then one of the other 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 was stuck at it for four years why editor and not, necessarily? You're a very good writer. I'm not as adventurous as most reporters.
I don't savor 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.
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? Well, Brian would have been a 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, uh, try to inspire the writer and, and, you know, the job of the editor is to, to sit you down Cara on, on Monday and say the job, the, 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 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.
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. I mean, I suppose at some point AI is going to replace them, but I think that 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.

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? Yeah, I can.
Go ahead. 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 striver from an outer borough are his cufflings, huge mosques of gold and stone the size of half dollars.
So you kind of nailed them right then as an outsider, obviously, to the Manhattan world. And 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. 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.

People don't get that part of him.

He's actually very charming.

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 the man I knew over 40 years. it's um he was he was he was transactional and he was

you to the man I met and the man I knew over 40 years.

He was transactional and he was always on, you know,

not the make, but, you know, looking for the advantage.

But this sort of scattershot last two months are not what I expected at all.

But 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.
Right. So talk about that original man, though.
Where are the similarities? Because you seem to have nailed him pretty closely about what people think of him now. A 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.
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 same time so that it would seem like it was one of their bestsellers of all time.

And I think, strangely enough, years later, I was working for Cy Newhouse,

who owned Random House and Condé 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

Thank you. 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. It's all your fault.
Yeah, 100%. 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. 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 there.
So you and Kurt Lade 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.
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, and it's the world that Tom Wolfe captured in… Bonfire of the Bandits. and so and was a, you know, he wanted to be out there.
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. It was sort of the beginning of your very public.
Some people think it's a feud. You called it an enduring love fest in 2013.
And you were interviewed about him for this 1991 documentary. Let's listen to what you said.
I want to get an idea of what he represented versus what you were doing at SPY. The only end to this road is sort of ultimate madness.
You know, living alone in an apartment complex in Panama and growing your fingernails long and stirring your urine in mason jars. 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 going to, you're not going to catch him out, you know, with a taro 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. Well, that's very prescient.
I might have got both points right. 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 Bonneville in part.
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. He just bought one.
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 he's just a kind 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. Yeah.
Do you think your attack's 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? 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, um, 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'm talking about the overall encroaching bro culture, which I hate. 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. It's 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 think about what's happening there and also the snap elections that Mark Carney just called? He's done wonders for liberal democracies around the world, and in terms of unifying them and making 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 similar 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 a hitting 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. Do you imagine it could happen? This could actually happen? No, I don't know.
I don't understand what the end game is here. Well, 51st state.
No, no. That's like saying, I'd like to take your house, but without paying for it.
And I just don't see it happening. I mean, the Panama situation may be different, but I don't see Greenland or Canada happening.
And do you have any idea why he wants to do this from many of the years of observing him? Because I think he loves to flood the headline zone. You know, since he's been elected, there are 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. 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. You're Taylor 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. 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 jump suits during the war.
I mean, this is a man who's been at war for the last two years or so. And 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.
I say he looks like a lesbian I used to date in the 1980s. Yeah, no, like a heavy metal loving lesbian.
Yeah. We'll be back in a minute.
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Download Thumbtack today. 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.

I'm Kurt Anderson, 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, try to start another publication, go into show business, what? 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 Diefen Bakery that specialized in butter tart bars and beaver tails. But seriously, what is your career path, do you think, absence by? Congratulations on the book, and see you soon.
For people who don't know, Diefen Baker was a prime minister of Canada. Kurt's making a Canadian joke.
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 don't know.
But I'd probably somehow find a way back into editing. So you left Spy after a brief interlude for the New York Observer before being tapped by Cy Newhouse to become editor of Vanity Fair.
And one of the reasons you left Spy was the new owners started meddling editorially. You talked about it.
You say Psy 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 Psy Newhouse did that was different.
Well, at Spy, so Kurt Neiss and our partner, Tom Fellows, we sold it to Johnny Pagazzi and Charles Saatchi. And as is their right, they wanted certain people on the cover, and they wanted us to do this and 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 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 can get this to be a kind of thing. And I had a six month and a 12 month and an 18 month plan.
And by about the sixth 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.
And so Cy, 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 calls 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 he anyway he he got right to the take out to the chase and he said would you um i've got two magazines and wonder if you'd be interested in either of them he And he said, The New Yorker and Vanity Fair.
And I 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 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 six-month, 12-month, 18-month plan of what do I do to change the New Yorker. It would not be in dramatic shape in any way.
More just slow sort of changes. 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. 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 been confided with Anna because I think she was his closest confidant.
I understand her point of view but I know that my story

is correct as well. But I had no plan 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. So it was a job you didn't want but got anyway, essentially.
No, it's not that I didn't want it. It's just that it surprised me.
Right. And then, and after the two-year period, and this is a long period in, you know,

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, cause I like a, I, uh, 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, uh, rather than having it in your, your actual office. And so I, you know, all of a sudden I can bring my children to work, my wife, and my colleagues started saying please and thank you after discussions.
And it changed the whole temperature of the office. 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. 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 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 Cy Newhouse.
There's Mark Benny off at Time, Lorraine Powell Jobs at Atlantic, who seems to be doing a pretty good job, Patrick Asun-Shang 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 they're losing a lot of money, and so there's a little different situation going on. 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 element 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 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 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 an owner getting too involved in the editorial process, I don't know of an instance other than small magazines where that works. How do you assess current owners like Bezos, for example? 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.
They're going to pay you. It was like $10 for a year.
And I thought, okay, that's not a business anymore. Right.
And whereas 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. Right, right.
Well, he's already sort of burned that bridge with that piece he wrote, I think. If I was Jeff, I would suck it up and see if I could bring him back.
Well, he needs both a CEO and an editor. Right.
So wouldn't 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 Fair revealing Mark Felt as Deep Throat, Woodward 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. 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 if 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 got a phone call from a lawyer who said that he represented the man who was deepthropped. 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, nor had the editor David Friend.
But we thought, okay, let's proceed with this. And so there were issues here.
There were problems here. First of all, 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 throw.
And so this went on for two months, and we weren't 100% sure that it was him. And anyway, we closed the story.
I get married. I go on my honeymoon, and I'd forgotten all about this story.
And we were in the airport in Nassau 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 newsstands 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-throated. 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.
Anxiety. Anxiety.
Well, this is kind of interesting. You talk about it.
You were very anxious to the whole thing. 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 fired. You also write about 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 that stewing and worry. So talk a little bit about the idea of anxiety and failure.
Well, I mean, I do think, I have a feeling that even johnny carson who did the tine show every night for decades that he would get anxious before going on stage and i remember reading the laurence olivier even laurence olivier would get anxious before um going on stage so i think that uh 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 wish I wasn't this way, but I am.
So was there one thing that you, a failure from those early days that you remember? 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 out by a bunch of college kids who didn't know what they were doing.
And 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, the Waverly Inn, which we took over.
I've been there with you. 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 banquette type restaurants, very few with white tablecloths and with low lighting. And so the restaurant had a point and it's, it's continues to do well.
Um, and with Spike, 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.
So having a point, it got you to have a point when you didn't have a point before. Yeah, if you have a point, you'll have a better chance of success.
Success. So speaking of that, one of the things, you were at 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. We won't be a copy from the best, Karen.
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.
I mean, I didn't think of these as innovations. I thought of them as sort of organic extensions of the magazine, not all were my ideas some of them i went kicking and screaming on and but it um they did expand the the magazine sort of um 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 franc then we also did, I did an annual dinner and party with Mike Bloomberg around the White House Correspondents Dinner.
And, you know, 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 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.
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 Condé Nast, no bottom, no ceiling. You flew a correspondence all over the world, all expenses pay.
You put Dominic Dunn up at the Chateau Marmont for months when he was covering the O.J. Simpson trial, probably money well spent.
Condé gave out industry loans for apartments, leased cars. Writers gave him weeks, months to write.
Brian Burrow wrote a review of your memoir titled Manity Fair's Hay Day. I was once paid 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. 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 at Condé Nast in the 1970s, it was the third-tier publisher.
There was Time Incorporated that came first. Hearst came second.
And Condé 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.

We'll be back in a minute. it.
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Peloton. Ad revenue for print magazines was reported in 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 Condé Nast.
And when I did an interview with Roger Lynch, he told me that Condé Nast is no longer a magazine company. If Condé Nast is no longer a magazine company, what does that mean? I don't know.
I want to know. What do you think it means? I have no idea.
It's a content company. I believe that's what he meant.
Multi-platform. Multi-platform.
Multi-platform. Omnimedia.
Martha Stewart was right all along. But 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. 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've got Private Eye from England and World of Interiors, and you would never know there was a recession with some of these magazines, with the exception of the English Papers magazines.
They're great online experiences. So, I think that know certain types of magazines will do well and a lot of it depends on the the editors um 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 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. 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? You obviously don't pay people six figures, etc.
What is the thought of when you were starting that, and why? 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 cycle and 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 Alessandra Stanley. We worked together at Time Magazine 40-odd years ago.
And my friend Jim Kelly was their book setter. 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. And what's your goal in this?

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

Yes, exactly.

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.
So you're known as the editor of Banffier, 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 and a Peabody.
You produced a Broadway show with Bev 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? I do love having the bricks and mortar. I love our shop 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 it. The nice thing is 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.
I didn't vote for him. Back to Trump, yeah.
So 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 had them in the shop, and we had 500 made.
They were sold out in three or four days. So now we have constant reorder.
Do you think of yourself as an entrepreneur? No, I think of myself, but just sort of open for ideas and willing to dive in and not be afraid to make a complete fool of myself. 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? 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 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 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. So my last question, where do you think the Trump story ends?

Mason jars in Haiti or Guatemala. That's too depressing to think of.

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

Thanks so much thanks so much Cara if you're in New York on Monday April 7th join me for a live taping of on with Cara 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 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 Yoakum, Dave Shaw, Megan Burney, Megan Cunane, and Kaylin 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.

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