Media People: Graydon Carter and Alessandra Stanley of Air Mail

Perched in front of a large framed historic map of Paris in his home office in Manhattan’s Greenwich Village, Graydon Carter is patting down his trademark mop of unruly white hair, always parted on the left side. “I just got my hair cut today so you know when you have little bits of hair and it’s driving you slightly crazy?”

Carter, almost as famous for his hair as he is for his 25 years leading Condé Nast-owned Vanity Fair, has been back in the city for a few months, having spent much of the pandemic at his new apartment in Provence with his wife and youngest daughter, who even enrolled in a local school during their time in the picturesque region.

More from WWD

• François Pinault’s New Contemporary Art Museum Bourse de Commerce in Paris

“I think you went to France to get away from us,” jokes Alessandra Stanley, a former Moscow and Rome bureau chief for The New York Times who is now his coeditor at Air Mail, the weekly online newsletter he founded in 2019.

The two, both warm and friendly, have an easy and convivial relationship — the result of a 40-plus year friendship. Stanley, who was also at one point The Times’ TV critic, was the first person Carter approached about Air Mail, the idea for which germinated when he was mulling retirement in France after stepping down from Vanity Fair. “We were in France. We came back for a period and there was only one person I wanted to do this with and it was Alessandra and we went to dinner at the Waverly Inn [Carter’s restaurant] and God bless her she said yes on the spot.”

Since then, Air Mail has grown from its flagship Saturday weekly newsletter to several, including a Wednesday culture newsletter, a Thursday book report one, and a Friday newsletter for kids. There are also podcasts and an e-commerce arm Air Supply, featuring curated products across men’s and women’s fashion, books, tech, home and automotive.

But when it comes to discussing Air Mail’s performance almost two years in, with a large chunk of that time being a pandemic, both Carter and Stanley admit to not being stats people. A p.r. representative is on hand, though, with some figures showing that the site, whose subscriptions range from $80 a year to $10 a month, has 1.5 million monthly page views and 385,000 monthly uniques.

While the rep. declines to discuss financial details, she does reveal that the title’s subscription revenue is up over 183 percent in the first quarter of 2021 compared to a year ago and that advertising revenue is up over 50 percent (Air Mail has one advertiser per issue). All in all, it’s not yet profitable, but the hope is that it will be in about three years.

Here, Carter and Stanley chat to WWD about their careers, Air Mail’s inception and plans for post-pandemic coverage — anything but stats.

WWD: How did you two meet?

Alessandra Stanley: We met years ago at Time magazine. A bunch of people ended up being friends like Walter Isaacson and Michiko Kakutani. Graydon was a very dashing correspondent and that’s when we met and I was much too intimidated to talk to him.

Graydon Carter: That’s not true. I was a writer not a correspondent, which means I was a desk jockey. I had the trappings of a correspondent.

WWD: What year was this?

G.C: I got there in ’78. I think [Alessandra] got there in ’79/’80.

A.S.: ’80.

WWD: Those were the good times of journalism. Graydon, is it true that you actually had someone come to your lunches to take notes for you?

G.C.: I remember going to lunch with Sophia Loren and in those days you took your researcher along and they took notes for you. It was a very sheltered, cosseted life at Time during those days. We used to have a drinks trolley that they would put at the end of each hallway on Thursday/Friday nights. They’d bring dinner on a trolley to your desk with wine. The company was rolling in money in those days.

WWD: Can you explain your journey from Time to Vanity Fair?

G.C.: I went from Time to Life, started Spy magazine in 1986 with Kurt Andersen, who also worked at Time in the late ’70s/early ’80s and we sold that. I spent a year rejiggering the New York Observer, which was a slightly boring pink broadsheet at the time. And then Si [Newhouse] hired me for Vanity Fair and I spent 25 years there.

WWD: You almost became the editor of The New Yorker and not Vanity Fair, though, right?

G.C.: Si had hired me to be the editor of The New Yorker. Actually, he offered me both and I chose The New Yorker and I worked on a plan to energize it over a two-week period and then the day it was supposed to be announced I got a call from Anna Wintour, who said it’s not [The New Yorker] it’s [Vanity Fair] so I was surprised. Si called me 10 minutes later and he said it’s going to be Vanity Fair and I was making no money at the time so I thought that this is great for the life of my family. I had three children at the time. So I jumped at the Vanity Fair job and spent two miserable years there until I managed to get my feet really under the desk and then it became 23 years of the nicest years of my life.

WWD: When Graydon was at Spy and Vanity Fair, Alessandra you were in Moscow and Rome. What years were you there? Were you in Russia during the 1991 coup d’état attempt?

A.S.: I was overseas from say ’93 to 2001. I got [to Moscow] at the end of ’93 and it was Boris Yeltsin by then and so it was fighting, but it was different. It was the discovery of capitalism as opposed to the death of communism. Well, communism was still there but they were trying to dismantle it.

WWD: Do you think it was easier and perhaps safer to be a foreign reporter back then than it is now?

A.S.: Yes. It was dangerous for business people at that time. It was sort of the Chicago years of the ’30s. Journalists were relatively safe and even Chechnya — we had two wars in Chechnya while I was there — it was scary but journalists weren’t being kidnapped and held for ransom. That happened later. I’m very impressed by people who are going places like Iran, Iraq, anywhere now. It was just different.

G.C.: Especially when you have a former U.S. president trashing journalists to the world and saying this is acceptable to attack journalists.

WWD: I know some reporters in Russia and they’re convinced that their offices are bugged. Was that ever a concern for you when you were in Russia?

A.S.: It was exactly the opposite. It was bugged because nobody knew how to remove the bug, but nobody was listening. So no that wasn’t the fear.

WWD: Were you still there when Vladimir Putin came to power or had you already moved to Rome?

A.S.: I’m embarrassed to say that I knew who he was and he was probably the last person I would ever have guessed would have become president for life. But I left.

WWD: How did Air Mail come about?

G.C.: We were in France and my wife and I always used to pick up all the foreign papers on Saturday and Sunday and go through them and tear things out to share to each other and when we were over there I thought that there are so many great stories that I don’t see in the American papers, which are quite obsessed with that Boston to Washington corridor and then stories in the Midwest. I developed this notion of putting together first of all a newsletter and then it evolved into a proper handsomely designed digital weekly and we came back and raised the money and hired the staff and the staff is made up of a lot of young people. Some people from Vanity Fair, some people from Spy, two people from our days at Time.

WWD: You’re both coeditors. Do you have specific things that each one does in the business?

G.C: It sort of evolved naturally. There are things Alessandra’s better at than I am. I spend a lot of time also in design.

A.S.: I have a little bit to do with editing stories, but nothing to do with what I think is so great about Air Mail, which is the design.

WWD: How many staff do you have right now?

G.C.: Probably 30-ish.

WWD: And you have some growth plans for that?

G.C.: Yeah, we’re not just adding people on for the sake of adding people on. There are more engineers we’re going to take on. We’ll probably bring on another editor at some point. That person will probably be in Europe. We’re going to do a French edition, a Spanish language edition. We’re going to have two or three podcasts by the end of the year. We do these weekly newsletters — one on Wednesday about culture, one on Thursday about books, one on Friday for children. We’re going to do another on Sunday so there’s growth plans.

WWD: Is your son, Ash Carter, following in your footsteps?

G.C.: Yes. I’ve tried to dissuade him from that, but yes he’s an editor at Air Mail. He’s a beautiful writer. He had a book out two years ago on Mike Nichols. Actually, I’ve got five kids and two of the other ones write for Air Mail on a regular basis — one on spirits and one’s a book critic.

WWD: I’m interested to know what different companies are thinking about return to the office. Are you going to have everyone back in New York? Are you keeping your office?

G.C.: We’re not forcing anybody back until they’re ready. The office was too crowded before the pandemic. There’s 30 people in them and I think it would be better if we staggered them. You go into an office not to work. You go into an office to talk to other people and plan things. Working now we’ve discovered is much better done at home. I know for me when I was at Vanity Fair I got all my work done before I got to the office. I got all my manuscripts edited, all my emails. When I went to the office it was to talk to writers and photographers, and editors. That’s what will happen here.

WWD: Can you talk me through some of the main changes that you have had to make to your strategy from when you first launched to now, mainly due to the pandemic?

G.C.: Actually, almost nothing. Other than the working conditions.

A.S.: The only thing you and I — because we’re of a different generation — didn’t think of at the time was social media and how important it is. So we kind of had to retrofit social media to Air Mail and that was a valuable lesson, which took me a while to get a handle on. It just wasn’t part of what I thought was creating a great publication. But it turns out it was essential so that was a big change.

WWD: Do you have a specialist social media employee now?

G.C: We did, but she just left to join an NGO centered on the environment so we’re in the process of looking for a new person.

WWD: Who is Air Mail’s target audience? Is it a Vanity Fair reader or is it someone else?

G.C.: Very much a Vanity Fair reader. Every young person I know in Europe and America, the vast majority read it. Vanity Fair’s audience was about 1 million, but around 80,000 were the key readers and then you’ve got a huge aspirational audience as well. We don’t have that huge aspirational audience, but it will come. We do have the key readers and those are the readers that the advertisers like and I think that they feel part of a community — the readers. This was never intended to be gigantic. It was intended to be more class than mass. It’s intended to grow over the long term. I’d like this to be thought of as Hermès. It’s more Brunello Cucinelli. Not like H&M or Zara.

WWD: No fast fashion here.

G.C.: No fast fashion. No fast anything.

WWD: There have been so many other launches in this arena like Substack. How do you feel about all of this and do you view them as competition?

A.S.: No. On the contrary I think it’s a huge help because it’s balkanizing where you go for writers. You don’t have to always be at The New York Times, The New Yorker or The Atlantic. You can look here, there and there so a lot of people are coming to us from Substack because someone recommends something from Air Mail. I think that the big institutions lose a little bit of something with Substack and the smaller ones benefit from it.

G.C.: The great thing about today is that in the olden days — and that is like 25 years ago — if you didn’t have the means of production or a connection to the means of production — whether it’s a newspaper or a magazine — you didn’t have a voice. And the internet gives everybody the means of production and your job is just to produce something of quality that people are going to want to read or listen or watch. So it has democratized thought to a great extent and there’s upsides to that and downsides to that, but that is a great thing. If you have a specific voice that is original you will find an audience. It will just take longer.

WWD: Graydon, have you had any involvement in Jon Kelly, the former editor of Vanity Fair’s Hive’s new venture, which has been described by The New York Times as a Vanity Fair for the Substack era, even on the advisory side? I know that you have the same backers — TPG. (As first reported by Insider, Air Mail is in the process of raising an additional $15 million in funding).

G.C.: One of the same backers. This is going to be Jon’s project. I was sort of in the bleachers encouraging them from the sidelines. It will be a version of what we built at Vanity Fair. It will be a version of The Hive, but different. No, I’ve got my hands full with Air Mail.

WWD: What makes Air Mail stand out in this space?

G.C.: It was the first properly designed digital weekly that looks like a magazine. It doesn’t have a gazillion ads jumping all around it. Right from the beginning we wanted one sponsor per issue — it’s Hermès and Prada and Ralph Lauren and Brunello Cucinelli and Tod’s and HBO and Apple and things like that. They’re beautiful ads. They actually make Air Mail look better. Air Mail is the most beautifully designed digital journalistic entity out there because we care.

A.S.: We try to find stories that haven’t been reported a lot in the States. So it gives people a reason to look at Air Mail because they’re not going to read that story in The Wall Street Journal.

G.C.: If a story has been covered heavily in the Journal or The Times or The New York Post, we won’t do it. Most of the stuff we try to make it as fresh and interesting as possible to an American audience.

A.S.: And another thing — humor. Because the one thing that’s been terrible about the pandemic is not only has it been a terrible pandemic, but it’s very hard to not get very depressed when you’re reading the newspaper or reading a magazine because news at every level has been pretty terrible. So it’s kind of refreshing to read stories that are a little bit off the news and are about art and culture and film and crime and all those things that are different.

WWD: Do you ever see an events, social, party aspect of Air Mail or are you done with parties?

G.C.: Well, I sort of am. But I think that if the right thing came along we may be able to do it. I had such an incredible events team at Vanity Fair and even then I found it a chore. Putting on the Oscars party, it was like one of the longest, most tiresome nights of my working life each year. Everybody else was having fun, but it took a lot of work on my part and my staff’s part to make sure that the other people could have fun. We might do that, but it will have to be the right thing.

WWD: Are there any kind of wild situations you can remember from those parties?

G.C.: We used to do these dinners every year at the Hotel du Cap and one year this very famous French actress who will go nameless had had not enough food and way too much wine and she collapsed and not only had she collapsed, but I saw her lying there and she was the color of asphalt. I thought she was dead. So the hotel quickly had someone come over to her. They tried to revive her. They quietly get her up and into an ambulance and off to the hospital and I mentioned this to Alessandra, but nothing kills a party faster than a dead actress. Actually, we had a similar situation with a very famous older actress at the Hollywood party where she’d had too much to drink, too tight a dress and not enough food and she collapsed.

WWD: Oh, my God.

G.C.: We were prepared for almost anything, but dead movie stars is not something on the plan list necessarily.

WWD: You needed more food at these parties.

G.C.: There was plenty of food. It’s just that when people pour themselves into tight clothing — men and women — then you’ve got to be careful.

WWD: Outside of events I know you’ve been getting into other areas, including podcasting. Are we ever going to have a podcast with you two?

G.C.: Oh, God no. Our families wouldn’t listen to that.

WWD: Can you tell me a bit about the e-commerce side of the business?

G.C.: [David Foxley] started off as my assistant years ago at Vanity Fair and then became an editor at Architectural Digest. I knew he had spectacular taste. We live in the same apartment building strangely enough. And there was one person that when we decided to build it out that I thought who should run it was David. And he does an amazing job and I bet in a year’s time this will be the biggest money earner that we have. The Strategist of New York Magazine almost pays for everything there. This was never on the business plan when we first started.

WWD: We mentioned that you were at Time during the good days. You were also at Condé Nast during the days of town cars and huge expense budgets. Was it hard to go to a start-up without all of that?

G.C.: No, it’s funny — when I left Vanity Fair there’s a price to be paid for all of that. It’s a lot of work and it takes its toll. I thought I would miss my car and driver, but then we moved to France and the offices [in New York City] are two minutes away and if I want to go any further, there’s Uber. So I don’t miss having a car and a driver. I’ll be honest — I’ve been happier at Air Mail than I have been in decades. I love the staff. I’ve known most of them for many years.

WWD: What’s one of the most extravagant expense stories you have?

G.C.: In my first three years [at Vanity Fair], there were no budgets. You spent what you needed. I remember one time Si and I would have lunch every week and we usually talked about something other than the magazine and one time we had started this Hollywood cover that became like Vietnam. It was shot in three panels and the background had to be shipped around the world to get each panel shot and once you shot one panel you were committed to doing two others and we had a shoot in New York and Paris and London. At one point I was having lunch with Si and he said, “Anything going on with the magazine?” I said, “Well, I’ve got some good news and bad news.” He said, “Well, what’s the bad news?” I said, “I think we’re in the process of shooting the most expensive magazine cover of all time.” It was in the hundreds of thousands of dollars. And he said, “What’s the good news?” and I said, “It actually looks like the most expensive.” Si gave you the tools to be successful and so you could either be successful or not be successful, but you could never blame him for it.

WWD: On diversity and inclusion, I know Vanity Fair has come under the spotlight for not being the most diverse and inclusive in the past in terms of staffing and covers. Alessandra, you’ve also been called out for your column at The Times. What are you doing to ensure diversity and inclusion is a priority at Air Mail?

A.S.: The truth is we haven’t said we must have this kind of person. But what we have done — we’ve been very lucky: we have some amazingly talented people from all over the world, who fit the category of diverse whether it’s because they’re South Asian or African or whatever. So it hasn’t really been a problem. But I do think it’s incumbent on us — we couldn’t have an internship program during the pandemic but we’re hoping to build one this summer where we can help kids who don’t have family connections and don’t have tons of money and exposure, but who are talented to have an internship that would be paid. That’s been one of the hardest things and there’s so many incredibly talented people who have fancy parents or whatever, but there are a lot of very talented people who don’t and who actually need a leg up. And I think through NYU journalism school and a couple of other places we can do that and that makes sense and every publication is doing that now. I think we should, too.

WWD: Has the role of editor in chief changed?

G.C.: I’ve been an editor since 1973 and the job is absolutely identical. Your job is to talk to a writer or photographer and convince them that is the most important thing they’re ever going to do and then turn around two months later and tell them that the next thing is the most important thing they’ve ever going to do. And then you have to get everybody — you’re like a choirmaster trying to get everything — different voices and different images and all the rest of it. You have to make it work in unison and not be discordant with each other. I don’t think it’s changed in 200 years. Just the method of delivery has changed.

WWD: Do either of you still read magazines?

A.S.: Online The New Yorker, The Atlantic. What else do I read? That’s it. National Geographic. Le Point.

WWD: No print subscriptions?

A.S.: I don’t have any.

G.C.: I do. I subscribe to Yankee magazine for the Northeast. Oh, and The Oldie, which is this magazine from England started up by the Private Eye people.

WWD: Do you read Vanity Fair since you left?

G.C.: I look at all magazines on Apple News Plus just to see what they’re doing.

WWD: You’re not on social media, are you?

G.C.: No

WWD: You never will be?

G.C.: I did one tweet. I said it was a collector’s item.

A.S.: Air Mail has a social media presence, but I just think that it’s so easy to make a mistake on Twitter. If you’re already writing and publishing things, then the rewards of Twitter are minor.

G.C.: That’s true.

A.S.: It’s very good for marketing.

WWD: Do you still see print magazines still around in 20 years?

G.C.: Yes. I think that the weekly print magazines will have a rough time because you’re competing against the internet. Unless you’re a great-looking magazine and you’re giving something that’s unavailable on the internet in terms of stories like narrative stories I think you’ll have trouble. But I think magazines — already they’re moving for young people into the vinyl stage. They’re cool to have. You go down to the newsstand on Eighth Avenue and there are big $25 magazines beautifully printed, obscure titles from all over the world and they get lapped up because I think young people love magazines. That love will increase as things go on. But you’ve got to become more magazine-y. You can’t look like a leaflet that comes in the mail for free.

WWD: Alessandra, you’re from the newspaper world. In 20 years do you think we’ll have print newspapers?

A.S.: I don’t see why we would but I could be wrong. Especially during the pandemic so many people have canceled their paper subscription. The advantages of reading it online are huge. The one thing that’s missing is what everybody says about newspapers is serendipity of flipping and finding a story that otherwise you wouldn’t have seen and they should come up with a way of doing that.

G.C.: I read everything on my iPad now.

WWD: Graydon, are you writing a book?

G.C.: Yes I am, but it’s slow because I have a day job. Something like a memoir.

For more, see:

Media People: Robin Givhan of The Washington Post

Media People: Kristen Welker of NBC News

Media People: Margaret Brennan, Moderator of ‘Face the Nation’

Media People: Moving On With Suzy Menkes

Sign up for WWD's Newsletter. For the latest news, follow us on Twitter, Facebook, and Instagram.