“We Didn’t Understand the Language”
In this (potentially triggering) excerpt from his excellent book, Dilettante, author Dana Brown describes the beginning of the end in gory detail.
ILLUSTRATION BY NEIL JAMIESON/THE SPORTING PRESS
As the 2000s came to a close, and the new decade began to come into focus, I was on the cusp of turning 40. Middle age. A scary time, especially for someone with two kids under 10 and a hefty mortgage on a Chelsea loft I could barely afford. New York had gotten increasingly expensive over the previous decade, as Wall Street exploded during the Bush years. The city was awash in banker and hedge-fund cash and the cost of living was adjusting to this new reality.
The creative class, of which I had been part of for the previous 15 years as an editor at Vanity Fair, was on a downward trajectory, our salaries no match for a city catering more and more to the wealthy and super rich. And I suddenly had an under-siege expense account, as budget cuts at Condé Nast put increased scrutiny on them. I don’t expect any sympathy over that, I just thought I’d mention it.
It was a scary time in the magazine business. We had been going through what was kindly being referred to as a correction since the 2008 crash, but it was becoming clearer there was something more going on. Newsstand sales had been falling, advertisers were fleeing print. We were always on the verge of turning a corner, or so we were being told, but in reality, we had been bleeding out slowly. We were living through the industry’s descent into a dark age.
Obviously, the financial crisis, the worst since the Great Depression, which began with the collapse of Lehman Brothers on September 15, 2008, took its toll. With most content free online, suddenly spending a few dollars on a magazine seemed like an unnecessary expense. Advertisers got cautious, shut off the spigot. But economic downturns and recessions happen, industries and businesses take a hit, make some adjustments, cut some costs, ride it out until the next boom. This was different. And it was becoming clear why.
A year before the economic collapse, in 2007, the iPhone had been introduced, instantly accelerating the explosion of mobile technology and the rise of social media. Twitter arrived the year before that. Facebook’s users grew from 100,000,000 to 240,000,000 in 2008. It was a perfect storm. The financial crisis, the iPhone, Facebook, Twitter: the four horsemen of the magazine apocalypse. Instagram and Snapchat would launch in 2010 and 2011, respectively. Two more horsemen in what would soon become a marauding cavalry.
Suddenly everyone was on their phones, and social media, instantly connecting with the world, posting and tweeting and tagging and sharing, creating their own little social ecosystems, curating their own little magazines and stories, some even turning themselves into celebrities.
“We were living through the industry’s descent into a dark age.”
Along with the rest of the industry, Vanity Fair’s newsstand sales were in free fall. We were averaging under 200,000 copies a month. When I began in 1994, and throughout much of the 2000s, our average monthly newsstand sales were somewhere in the 350,000 to 400,000 range. A sale under 200,000 would have been cause for alarm. Hollywood issues would regularly edge into the 500,000 or even 600,000 territory, and a blockbuster issue could get into the 700,000s.
September 2005’s cover of Jennifer Aniston, the issue in which she broke down during the interview about her split from Brad Pitt, sold more than 738,929 copies. Tom Cruise, Katie Holmes, and Suri’s October 2006 cover sold 713,776. But beginning in 2008, newsstand sales began to tank. For the next decade, they would fall by at least 10% a year industry wide. By 2018, they had fallen by 60%.
And digital advertising and print advertising weren’t just on two different tracks, they were on two different trains, one modern, sleek and high speed, the other an old steam engine grinding down the tracks. In 2012, Google and their algorithms collected more advertising revenue than the whole print industry—magazines and newspapers—combined. Just a few years later, advertisers would spend more on digital advertising than print and television combined, and the digital market was on pace to capture two thirds of all advertising dollars by 2023—and right on schedule, it did. The shift was quick, and profound.
Facebook, which began selling ads in 2007, and Google, were able to target advertising at very specific demographics, and then show advertisers actual figures of who saw the ad, who clicked on it, and who made a purchase. They were data-driven businesses. We would sell you a page of advertising for $100,000, tell you it was going to reach a lot of influential and wealthy people, take you out to dinner, dangle an invite to the Oscar Party, order expensive wine, get you drunk, and hope you forgot to ask any questions.
• • •
The Boss: Graydon Carter with celebrity chef Ken Friedman (left) in Carter’s Vanity Fair office.
We weren’t data people. There was never anything scientific about how we made editorial decisions. An established actor had a big movie coming out, they’d sold well in the past, so we’d put them on a cover, or an up-and-coming actor had such a breakout performance that we knew would be talked about, so we would take a chance and give them a cover. When it came to stories, for the most part, it was a meritocracy—best stories win, and make it into the issue. Maybe there’d be some office politics involved, internal discussions, but there were never any focus groups or anything like that.
Magazine editors didn’t need focus groups—we were above that, we were our own focus group, cultural curators. Decisions were made on instinct and gut feeling alone, maybe some history. We’d put the issue on the stands, and let the market dictate what happened. Then we’d move onto the next issue. Sometimes we guessed right, sometimes we guessed wrong. Sometimes we’d experiment, like when we put a fresh-faced Justin Bieber on the cover in 2011 in a desperate and transparently cynical attempt to appeal to younger readers. It bombed.
Suddenly, you could look at web traffic, actual numbers and analytics, and you could see what people clicked on, where they spent the most time—engagement—where they were. And worse, advertisers were able to see that information. Overnight, there was science available to what we did. Content and distribution quickly meant something different than simply putting a magazine on the newsstands every month and hoping for the best.
As a result of the tectonic shift in advertising from print to digital, there was a bloodletting going on in the industry, especially on the print side; magazines were downsizing, jobs were being eliminated, and there was nowhere to go—it was a game of musical chairs, and the music was stopping more often and the chairs were disappearing quicker.
The booming digital media platforms with their inflated valuations and stock prices and—fleeting, it turns out—“success,” or optics of success, weren’t looking to hire an overpaid middle-aged print magazine editor who drank at lunch, bristled at open office plans, and thought CMS had something to do with country music. They were hiring kids who spoke this new digital language.
• • •
Carter in production mode with Vanity Fair’s art director David Harris.
By 2011, three years after the financial meltdown, it had become clear that this was more than just a correction. Our business was going through fundamental changes, or worse, an end-of-days comeuppance for our excess and arrogance. After the 2008 economic collapse, Condé Nast brought in McKinsey, the corporate consulting firm, to “study” how to transform the company from a print-based dinosaur into the digital media age, but that transformation led to massive cost cutting and layoffs and very few solutions, if any. Every few years after that Condé Nast would bring in another consulting firm, or excitedly announce some great company-wide realignment, which had the same outcome.
The good old days weren’t just behind us, they were reaching out of the grave, strangling us one by one. Print, at least of the daily, weekly, and monthly variety, was dying. Two decades into that Information Age that Vanity Fair had helped define, and was so closely tied to, this journey that I was on was faltering. We were of course no longer a magazine by then. We couldn’t be.
The magazine business, at least what it had been for more than a century, a print-based, subscription and sales, ad-selling business, was becoming less and less of a viable industry. Newsstand sales continued to fall, advertisers continued to flee, revenue was dropping. We were now a brand, focused on growing our digital footprint and finding other sources of revenue. Everything was increasingly digital, especially advertising, our lifeblood.
“As a result of the tectonic shift in advertising from print to digital, there was a bloodletting going on in the industry, especially on the print side.”
Digital advertising, and specifically digital video advertising, was rising at such a rapid rate, that it couldn’t be ignored. And social media was becoming a powerful marketing and distribution tool for brands, and video is shared at a rate that’s more than 1,000 times greater than a written piece of content. Consumers had short attention spans, audiences were getting younger, so advertisers, and therefore media brands, were beginning to chase Millennials and Gen Z. They weren’t reading the long-form stories on their phone, if at all, and digital really began to mean a phone, thanks to the iPhone, with most online traffic coming from mobile devices and shared via social media and other links. So this meant creating video, short videos, and lots of them, and building a distribution network while hoping something went viral.
In 2011, out of necessity in an effort to find some of those new sources of digital revenue, Condé Nast had hired a woman named Dawn Ostroff to head up a new division of the company, called Condé Nast Entertainment. The company was losing money at this point. Well, apparently. According to some press reports, it was estimated that Condé Nast was losing more than $100 million a year, but I heard whispers from reliable corporate sources that it might have been double that. And there was no end in sight.
• • •
Condé Nast Entertainment was created to try to capitalize on the power of Condé Nast’s brands, and the gold rush into digital video advertising. So the idea was simple, to create shareable—or “snackable,” a word that was thrown around a lot—video for Condé Nast’s brands, and reap the rewards of some of those ad dollars. To diversify, continue moving away from print. Which from a business standpoint makes total sense, and something we should have begun much earlier.
But we were a magazine company—we wrote stories and took pictures. Making video isn’t what we did. We were writers, and photographers, and text editors. This was a completely different skillset. So we needed help, needed someone to come in and do it for us. But of course, we didn’t want help. Were reluctant to give up any control, were being dragged kicking and screaming into this new era. Enter Condé Nast Entertainment.
Dawn had a long career in television, most recently as head of The CW, a successful run that saw the network launch hit shows like Gossip Girl and The Vampire Diaries. Her mandate was twofold. One was to leverage and monetize Condé Nast’s feature stories by turning them into film and television series, something Tina Brown had tried to do with Talk, the second to create an in-house production company for Condé Nast’s magazines to create short-form branded digital video.
The most successful of these videos at Condé Nast would be Vogue’s series 73 Questions, in which celebrities answered 73 rapid-fire questions, all in one take. It launched in 2014 with Sarah Jessica Parker, and is still around—unlike Condé Nast Entertainment, which was shut down in 2023.
No matter how much I protested and pointed out how absurd it was, to Graydon I was still a “kid”—I was 40 now, by the way—who was supposed to be up on all of this new technology stuff, so Graydon put me in charge of Vanity Fair’s move into digital video. I’d also had some experience with screenwriting, had written a few movies and television pilots over the years that had gotten me some meetings in Hollywood, although nothing much came of them. I had recently sold a magazine-set pilot to Hulu, called Disappearing Ink—the working title of my book—that Graydon had read and really liked, although that one didn’t go anywhere either.
The Rooms Where It Happened: In the eighties and early nineties, the Philippe Starck-designed, Ian Schrager-owned Royalton Hotel—especially its restaurant, 44—was where most consequential Condé Nast deals and decisions were made. It’s also where the author, Dana Brown, then a “bar back,” was introduced to his future boss, Graydon Carter.
Our relationship with Dawn Ostroff and her senior executives got off to a bad start. We were still in 4 Times Square, a few years away from moving downtown to One World Trade Center, and were meeting with Dawn and her two senior executives for the first time. After introductions, we sat on the couches in Graydon’s office, and as we sat, I could see Graydon’s eyes drifting down to the floor, to the feet of one of Dawn’s executives, his face recoiling in visible disgust. He was wearing some sort of leather clog, the kind you might see on a chef, or a 19th century Dutch fruit peddler. And Graydon had a thing for bad shoes. He was already mistrustful of these interlopers, who were hired to help translate the magazine to the digital video age, in which he would have to give up some level of control. And now they had offended him sartorially, and aesthetically, sullied the highly-curated mid-century motif of his office. As Dawn and her team went through their vision for our move into digital video, Graydon barely paid attention, his gaze rarely leaving the shoes for half an hour.
After the meeting was over, and I was back in my office, I got a call to come back and see Graydon. Before I could sit down across from him, he immediately got into it.
“Did you see those shoes?”
“Yeah. I know. They were really bad, like a faux-leather Croc.”
“It was a…dirty clog.”
“Can we talk about this video stuff—”
He cut me off and we talked about the shoes for a few minutes, trying to come up with new inventive ways to describe them.
Carter with Nicole Kidman in better times.
“What else is there to do but laugh in the face of your own obsolescence? ”
Now I know this makes us sound like dreadful snobs, even judgmental and cruel. But they were really bad shoes, and we had a standard to uphold. It was Vanity Fair, and Condé Nast after all, we were selling a fantasy, a lifestyle, and that crossed over into the real world, and our appearances. We were expected to be walking billboards for the fantasy we were selling. (Why do you think editor-in-chiefs got clothing allowances?) If I was bringing someone into Graydon’s office who he’d never met before, I would always do a shoe check. If they didn’t pass muster, I’d make sure we sat at his desk, passing up a more casual chat on his couches where the offending loafer or moccasin or dirt-caked work boot would be on full display. If this Condé Nast Entertainment executive was someone who was going to be making aesthetic decisions for us, and he had made the decision that morning to wear those cartoon shoes, well, this might be a problem.
I finally got him to focus on video, and I got my marching orders. Work with Dawn and her team, don’t embarrass the magazine, and “Don’t fuck up.”
The two executives wouldn’t last, but Dawn did, and we grew to really like her. We put her through her paces, as did most of the other titles, but she was clever, began to understand the politics of the building, was patient, persistent, and figured it out, building a new division from scratch, eventually getting hired away to be the head of content for Spotify. I’m proud of the early work we produced, which was upscale, smart and on brand, short documentaries and a few satirical series.
But upscale and smart doesn’t really work on the internet, as we discovered—they were judged failures. Over the years Vanity Fair’s videos would have to be adjusted, get even shorter—more “snackable”—celebrity driven, silly and superficial. Give the people what they want. Scale or die.
• • •
A few years after CNE came into existence, I had a meeting on my calendar, along with Graydon, in our conference room on the 22nd Floor of One World Trade soon after we had moved there, with Dawn and her team, which had grown exponentially. It popped up one morning in my Google calendar—which I barely knew how to use, and things would just appear, like magic—as a “CNE/KPI meeting.” There were so many of these meetings that I rarely paid attention to their titles or what they were about, my eyes glazing over at the thought of the endless and confusing PowerPoint presentation that awaited me. I stopped by Graydon’s office, and he saw me outside, nodded with something not even close to approaching enthusiasm, got up, and we started walking down the hall.
“What’s this about?”
“I have no idea. Just nod and smile. And don’t ask any questions. We won’t understand the answers and we’ll never get out of there.”
He nodded. That was our approach to most of these meetings.
We walked into the conference room, and said hello to Dawn. She had a team of maybe six or seven with her, sitting around the big conference table, most of them at least a decade younger than me. They all had laptops. I had a pad of paper and a pen. Graydon and I sat across from them as Dawn suggested they introduce themselves. The first one told us her name, and her title, which was something like “VP of Social Activation,” or maybe “Director of Social Outreach.” We nodded politely and smiled as they went around the table, saying their names and titles that meant nothing to either of us.
“I got my marching orders: Work with Dawn and her team, don’t embarrass the magazine, and ‘Don’t fuck up.’”
With the introductions now over, someone got up and dimmed the lights: it was time for the dreaded deck. This deck was no different than the last one, or the next one: slide after slide of charts, and graphs, and numbers and logos and acronyms. This one had references to KPIs on every slide. It was a KPI meeting after all.
About halfway through the presentation, Graydon grabbed my notepad, then my pen, wrote something down, and slid the pad back to me.
I looked down.
What does KPI stand for?
I was running digital video for Vanity Fair, had been tasked with building this new initiative, was one of Graydon’s trusted deputies, still the one he turned to when he wanted to know what was happening with “the young folks.” Never mind that I was now older than he was when he took over Vanity Fair and had no idea what any of this shit meant or how it actually worked.
I stared at that piece of paper for a few moments, and in that instant knew how much the world had changed, and knew that it had left me behind. The new technology and changes to the industry were coming so fast, it was impossible to keep up. This PowerPoint, these terms and acronyms, the job titles, the business model, this new Millennial and now Gen Z workforce and audience.
While we were making fun of them, the joke was on us. They were raised with this stuff, the internet and social media and new technology were intertwined with their DNA. It was part of the very fiber of their being. The cutting-edge new technology that emerged when I was growing up were things like cordless phones, microwave ovens, and VCRs. If something stopped working properly, we just hit it really hard and hoped for the best. Now we were past our sell-by date before we even got a chance to be put on the shelf. Cassettes in a streaming world.
I scribbled three words on that notepad and slid it back.
No fucking idea.
He smiled, and laughed quietly to himself. I couldn’t help but join in. What else is there to do but laugh in the face of your own obsolescence?
The deck came to an end. We smiled, told them it looked great, and we were ready to move forward with whatever it was they had just pitched, even though we had no idea what had actually been pitched. But we were on board with this KPI thing! Dawn asked us if we had any questions. I shook my head, No, and smiled. But then Graydon spoke up.
“Yeah, I have one question.”
My directive had gone unheeded. It was a pointless exercise. And worse, now we were never getting out of there.
“What does KPI stand for?”
The other side of the table just stared at us with blank looks.
That just about sums up where the industry was by the mid 2010s, and the generational shift that was skipping right past mine. We were supposed to be the translators between the generation ahead of us and the ones behind us before we took over, that’s the way it had always worked in the past. But we didn’t understand the language.
“I stared at that piece of paper for a few moments, and in that instant knew how much the world had changed, and knew that it had left me behind.”
Dilettante author Dana Brown.
Excerpted from Dilettante: True Tales of Excess, Triumph, and Disaster by Dana Brown (Ballantine Books/Penguin Random House, 2022). First edition published August 2, 2016. Get a copy here.