One day in the mid-1980s, Alex Liberman was standing in the Vogue art department as an executive tried to show him how to use a newly purchased digital layout system. After a few minutes, he lost his patience.
“Computers!” Alex declared, with his usual haughty flourish. “It’s a phase.”
Joan Juliet Buck, editor of Vogue Paris in the 1990s, once asked an executive at Condé Nast’s French headquarters to purchase computers for the staff.
“Non,” came the reply.
Flummoxed, Buck argued that her editors needed internet access to stay in electronic touch with designers and their colleagues in New York, London, and Milan. The executive sniffed, “They’ll be playing solitaire all day long.”
By 1994, the fashion team at Allure had made a great leap forward: a single computer was installed, for the use of the entire department. In 1995, Steve Florio was asked by Charlie Rose if he had concerns about the coming world of “electronic publishing.” “I don’t worry about it,” Florio replied. “I mean, the fact of the matter is, what we’re talking about here are ideas. And whether the record is on a 78 or a cassette or a CD-ROM, or whatever, you still want to hear the music.”
“When the electronic revolution is here,” Florio added, “we will have the content that the people that develop the system will want.”
The internet broke Condé Nast. No major magazine publisher anticipated the profound changes that the web would bring to the ways that people consumed news and information, images and words. But in Condé’s case, the dawn of the digital world carried an extra payload, perhaps the most lethal of all: it introduced the means of cultural curation to the masses. For a company founded on the precept of exclusivity, whose business model and social clout hinged on its perceived expertise in taste, this was existential. Looking back, the moments when Condé did innovate on the web—when it published early online recipes and the first online slideshows from fashion shows in Europe—are all the more agonizing because Si and his deputies never pursued them to their logical, profitable ends. For years, the company’s web teams were starved for resources, even as editors dreamed up innovations that, if nurtured correctly, might have secured Condé’s pre-eminence for a new generation. “You’re going to have to go a long way on the Internet to compete with the way we produce words and images in the magazines,” Thomas J. Wallace, Condé Nast’s editorial director, confidently told The New York Times.
He uttered those words in the summer of 2008.
“The digital world wasn’t the Condé Nast world,” said Deborah Needleman, whose ideas for online growth at Domino, a beloved and short-lived Condé magazine that she oversaw in the 2000s, were met with ambivalence and neglect. “They wanted to stay on the mountaintop.”
SI HAD ANTICIPATED the consumer capitalism explosion of the 1980s. But when it came to the internet, he was a skeptic. In the early 1990s, it seemed axiomatic to Si that the lushness and sheen of physical magazines was what announced Condé’s authority to the world and enticed high-spending advertisers to show off luxury goods in immaculately art-directed pages. He was also a wealthy magnate in his late sixties, who from childhood had loved the ink-and-pulp romance of print. The early internet, with its janky visuals and fragile dial-up connections, hardly seemed like much of a threat.
One Newhouse, however, was intrigued.
Steven O. Newhouse was the oldest son of Si’s brother, Donald, and he had grown up in the Park Avenue apartment directly underneath Sam and Mitzi. Steven attended Collegiate and Yale, the old-line elite education that had eluded his father and uncle, and as a teenager he worked classifieds at the Newhouse-owned Newark Star-Ledger. Like Donald, Steven had an unassuming side. Touring one of his family’s newsrooms, he reported feeling self-conscious, as if he “was being shown off as a curiosity”; when he transferred to a Newhouse-owned paper in Springfield, Massachusetts, he insisted on working the night shift. In 1983, at age twenty-six, Steven took over as editor of The Jersey Journal, a community paper covering the North Jersey suburbs, where he would remain for a decade, toiling in a nondescript Jersey City office that was a river and a world away from his uncle’s Condé Nast kingdom.
Steven appeared destined to succeed his father in overseeing the sleepy, if dependable, newspaper side of the Newhouse family dynasty. But in the early 1990s, Steven, seemingly alone among his family members, took an interest in the internet. “No one else in the business really cared or wanted to pursue new media,” he recalled. “I elected myself.” Steven joined a program at MIT’s Media Lab examining the effects of digital technology on the news business, where he encountered an early version of a web browser. At the urging of the lab’s director, Nicholas Negroponte, Steven persuaded his family to invest $3 million, reportedly in exchange for a 15 percent stake, in Wired, a new magazine in San Francisco about technology. Wired was in the process of creating HotWired, the first commercial online magazine, and Steven decided the local Newhouse newspapers should go online, too. In those early internet days, he had little trouble securing domain names like NJ.com, Cleveland.com, and Syracuse.com, all of which were still readily available. “If I had been really smart, I would have bought a thousand of the best URLs and made hundreds of millions of dollars,” Steven said years later.
It was right around then that Rochelle Udell ran into trouble with a turkey.
Udell, a longtime editorial director at Condé Nast, was hosting Thanksgiving dinner at home in 1994 when she realized she could not fit two whole birds into her oven. Was it possible to roast a turkey on an outdoor grill? Her collection of Gourmet and Bon Appétit back issues yielded no answers, so Udell logged on to America Online, a dial-up internet service just starting to attract a following. At 6:20 a.m. on Thanksgiving Day, Udell posed her question to a chat room called “AOL Talk Turkey.” Within minutes, she had more than twenty answers. Users followed up throughout the day to see how her meal was turning out.
Dashing between her kitchen and desktop computer, Udell was struck by an insight that many of her peers in publishing would take years, even decades, to fully comprehend. The internet was a wellspring of spontaneous communities, like-minded groups of people bonding across time and space over shared interests and desires—not unlike the readers of a magazine. Monthly subscribers were essentially signing up for a club, their membership (and whatever perceived status it conferred) signaled by the titles they kept on the coffee table. But instead of the one-way direction of editors declaring what to do and think—with feedback limited to the slow and highly mediated format of letters to the editor—the web allowed for instantaneous and interactive connections. It was a conversation, not a decree. And Udell, who had helped create the visual identities of Self, Vogue, and Robert Gottlieb’s New Yorker, believed there was no company better positioned to spark a conversation than Condé Nast.
After the holiday break, Udell approached the Newhouses. Condé was sitting on an incredible archive of recipes from Gourmet and Bon Appétit; why not put them online? Time Inc. had just launched Pathfinder, a website with articles and photographs from Time, People, and Fortune; other magazine publishers were experimenting with packaging CD-ROMs with print issues. Udell explained how recipes could be indexed based on ingredients, letting readers quickly sift through thousands of options. A website about food and beverage, she argued, could promote Condé’s lifestyle expertise. Steven endorsed her plan, and Si agreed—to a point. He told Udell that Condé would pay for the site, but it needed a unique name. Gourmet.com or BonAppetit.com, Si declared, were off-limits.
It was, in hindsight, a grievous error. Condé Nast controlled some of the most powerful brands in the world of lifestyle journalism. Yet, given the opportunity, it declined to plant those brands in the virgin soil of the web. Si, who did not use the internet, viewed the online world as untamed territory. He had built his empire on the mantra that perception was everything, and the potential of tarnishing Gourmet’s immaculate image by tossing it onto the web—an inchoate realm of gossip, porn, and god knows what else—seemed too big a gamble. He didn’t want to undermine the lucrative ad sales for his print magazines, either.
“The safe way of doing it was not to risk any brands, because you didn’t know what was going to happen with the internet,” Udell recalled. “We decided that it would be safer at that moment in time to call it something else.”
So Epicurious.com was born. In May 1995, Udell became the founder and president of CondéNet, a new digital publishing arm for the company. (It would be another ten years before Condé Nast deigned to officially absorb CondéNet; until then, it remained a parallel unit under the Newhouses’ Advance Publications umbrella.) Udell had a budget—minuscule by Condé standards—and a modest office on East Forty-fifth Street, around the corner from the 350 Madison mothership. Her internet connection had to be beamed in from 350 via radio waves; when the service kept dropping out, Udell discovered that a secretary was blocking the signal with a potted plant on a windowsill. CondéNet’s servers were stored in Jersey City, sharing a floor with a local dental office; when the dentist’s drill blew a fuse, CondéNet’s servers went dead, and any unsaved work was lost. Si had granted Epicurious the rights to digitize five thousand recipes. But in the bizarre, every-tub-on-its-own-bottom culture of Condé Nast, he barred the site from publishing any of the lush photographs from the Gourmet archives.
Epicurious’s launch, in August 1995, came without the fanfare that usually accompanied a new Condé publication, but it proved a modest success. A database allowed users to plug in specific ingredients—say, what they had sitting around the pantry—and find matching recipes. “Gail’s Recipe Swap,” a community board feature, attracted hundreds of dedicated commenters, some of whom met up in person for “IRL” dinner parties. This was a breakthrough in digital food media; Eater.com would not exist for another decade. Still, the message from the powers at Condé Nast was one of ambivalence, bordering on contempt. In July 1997, James Truman, Si’s editorial director, grew bored during a meeting of editors and executives discussing the future of Epicurious. Less than halfway through the gathering, Truman stood up.
“This is just too interesting for me,” Truman said, and left.
SI DID ULTIMATELY INVEST in the 1990s dot-com boom, but it was in the form of his favorite medium: a print magazine. In 1998, Condé Nast paid about $80 million to purchase Wired outright. According to Linda Rice, a senior Condé executive who was involved in the deal, Si refused to spend an extra $100,000 to secure the rights to Wired’s website and its other digital offshoots. At the time, the Wired website was losing money and dragging down the brand’s overall finances. Eight years later, Condé Nast would pay $25 million to reunite Wired and Wired.com. “Si would not spend the money,” Rice recalled, saying that the lawyers advising the deal were “practically crying” that Si could not see the long-term benefit. “When you have a family-owned business, you can do what you want,” Rice said, “and sometimes you are going to make mistakes.”
The combination of Condé’s shimmering Manhattanites with Silicon Valley–based Wired, a start-up whose workers ate lunch in an illegal loft kitchen, proved awkward. When Steve Florio flew to San Francisco to welcome the staff, he quipped, “Think of us as your rich uncles in New York.” The uncles did not disappoint. Wired’s then editor, Katrina Heron, was dumbfounded to be offered a $40,000 annual clothing allowance, an amount considered modest by Condé editor in chief standards. (She barely spent any of it.) Si encouraged Heron to accept an interest-free loan for a down payment on an apartment in San Francisco; when she left Condé Nast in 2001, no one at the company asked for the money back. “This is the worst-run business,” Heron remembered thinking to herself. “These people are idiotic.” Later, after she sold the apartment, Heron mailed a cashier’s check to Condé Nast for the amount she had borrowed. The accounting office called, befuddled, and asked Heron what the money was for. They had no record of it.
Meanwhile, the editors at Condé’s print titles in New York were given little incentive to familiarize themselves with the internet. When a features editor joined Vogue in 1994, he sent an email to the staff introducing himself. A response arrived from Anna Wintour—in the form of a fax. “This is Vogue,” Anna wrote. “We don’t email. It’s so impersonal.”
In hindsight, the ambitions of Condé’s tiny web team look prescient. One idea at Epicurious, never acted upon, was to post menus from restaurants across the country and allow users to place food orders. Another site, Swoon, featured an online dating section; a travel site called Concierge.com, an arm of Condé Nast Traveler, provided hotel suggestions based on users’ preferences (beach, city, golf). The basic tenets of Seamless, Tinder, Goop, and other future tech behemoths were there, but Condé’s leadership did not grasp the long-term potential. Instead, Si was content with small, minimally funded websites that were essentially cordoned off from his most lucrative magazine brands. By 1997, Vogue, Vanity Fair, GQ, and The New Yorker still did not have websites. “We are uninterested in making electronic versions of our print titles,” Joan Feeney, the editorial director of CondéNet, said that year. “That doesn’t make sense to us; it seems more a vanity operation than anything else.” She added, “People say, ‘Why isn’t Vogue online?’ And I say, ‘Why would it be?’ ”
In 1999, Anna agreed to experiment with a website. Ironically, her efforts, forward-looking and well-intentioned as they were, sowed the seeds of the digital fashion revolution that decades later would leave her and her magazine struggling for relevance.
Vogue.com launched in September 1999, and it became the first internet site to publish photographs of every look from high-fashion runway shows in near real time. Back then, shows in Paris, Milan, and New York were highly exclusive, and designers put strict limits on which of their looks could be photographed for public consumption; sometimes, fewer than half a dozen images were released. Anna took it upon herself to persuade designers to shed their concerns about piracy and exclusivity. She dispatched Joan Feeney of CondéNet to ateliers in Paris, armed with a laptop to show designers firsthand how their clothes would appear on the site. Many of the designers had never even used the internet; after some initial reluctance, they fell in line. “Because Anna blessed it, it came to pass,” Feeney recalled. Readers on Vogue.com were invited to sort photos by individual designers and specific categories, like swimsuits, lamé, and hot pants. (“Choose over 5000 looks from the world’s top designers.”) Thus Condé Nast pioneered the instantaneous digital coverage that would eventually undo its own authority in the fashion world.
Feeney had pitched her bosses on charging a twelve-dollar annual fee, about the same cost as a print subscription, but the sales executives said no. Their bonuses were based on print ad sales, and anything that threatened that revenue was anathema. Vogue.com would be further undermined a year later, when Condé introduced a new website that combined its magazines’ fashion coverage under one roof. Once again, Si set aside the company’s globally renowned brand names and instead created a new one: Style.com, a URL that Condé purchased from Leslie Wexner’s retail conglomerate, Limited Brands. On launch day, in September 2000, Style.com included a rudimentary revenue-sharing agreement with Neiman Marcus, whereby Condé Nast earned a cut of sales from merchandise purchased on the site. The soon-to-be-multibillion-dollar e-commerce market was in its nascent stages; Net-a-Porter had started just three months before. But in another so-close-yet-so-far moment, Condé let the opportunity pass by. It would be another fifteen years before the company embarked on a belated effort to convert Style.com into a full-blown retail destination. By then, in part because of its own hesitation to embrace the web, Condé Nast was no longer the paramount power in fashion. An entire generation of consumers raised on smartphones trusted the taste of amateur Instagram influencers and upstart retailers like Ssense over the expertise of editors at a single company in New York. Condé Nast invested more than $100 million in the new Style.com, which launched near the end of 2016. The site shut down after nine months.
AGAIN AND AGAIN, EDITORS CAME to feel that Condé—hindered by a combination of caution, arrogance, incuriosity, and incompetence—was years behind where it should be on the digital front. In December 2003, two years after The New Yorker launched its website, the magazine’s managing editor, Pamela Maffei McCarthy, wanted to post an online conversation between Philip Gourevitch and George Packer about the discovery of the deposed Saddam Hussein in a spider hole in Iraq. This was major breaking news, and McCarthy wanted the audio posted right away—but it was a Sunday, and she discovered that CondéNet did not operate on the weekends. At that time, The New Yorker had no capability to publish a story on its website on its own. McCarthy had to dig out a phone book to look up the home number of a CondéNet executive who could help.
As late as October 2009, editors at GQ and Details could only share “print” articles with Condé’s online menswear portal, men.style.com, twice a month. The site had no blog posts, and users couldn’t write comments. “We’re very 2002 right now,” a GQ editor quipped at the time. Linda Wells, the editor of Allure, recalled how difficult it was to get the attention of CondéNet or to secure a budget for a website. At one point, she pitched a digital “product finder” that would help readers sift through cosmetics products online. “I couldn’t get the tech or the support,” she said. Internally, magazine websites were often viewed as virtual advertisements that could attract subscribers to the “real deal” in print. In 2008, just 3 percent of Condé’s overall ad revenue stemmed from digital sales, less than rivals like Time Inc. Condé Nast did not appoint a chief technology officer until 2010.
“They just felt there was no point in being a leader,” recalled Dominique Browning, who edited House & Garden until 2007. “They would wait and see how things unfolded. I think that ultimately was a catastrophic decision, in terms of catching up with where the world was going. We were very, very slow.”
In Si’s defense, virtually no one in publishing at the time could predict the future. James Truman pointed out to me that the dot-com crash in 2000 had reinforced the broader institutional resistance to expanding on the internet. “Si thought [the web] was a giant money pit,” Truman recalled. After the late-1990s tech bubble burst, “people like Si looked like they had been right all along.”
Ruth Reichl, who became editor of Gourmet in 1999, nudged Si to create Gourmet.com for years. She and her staff had watched as online foodie culture blossomed and their magazine, the grande dame of epicurean glossies, was left behind. (Gourmet was first published in 1941, and purchased by Condé Nast in 1983.) Because Gourmet’s recipes appeared online under the Epicurious banner, Reichl believed she was missing a crucial opportunity to entice the next generation of food enthusiasts to read her magazine. By 2007, Si had relented and agreed to start a website, but he included a proviso that left Reichl dumbstruck: Gourmet’s own recipes were off-limits. Now it was Epicurious’s success that Si was worried about cannibalizing.
By 2011, Condé had created a new division, Condé Nast Entertainment, to focus on creating online video and bulking up digital revenues. But it could be hard to persuade some editors to pay attention. At one meeting with the division, Graydon Carter became distracted by a pair of ugly leather clogs worn by one of its top executives; afterward, the offending footwear was all he could talk about. “They were really bad shoes, and we had a standard to uphold,” recalled Dana Brown, defending his boss. “It was Vanity Fair and Condé Nast after all.” Around 2015, Vanity Fair put up a poster in its office that read, “Think Like a Start-Up.”
When James Truman and the editor Kim France founded a magazine in 2000 called Lucky, which celebrated shopping and included price tags on every item it featured, Truman saw an easy opportunity to expand into e-commerce. But Condé never took the last logical step and converted it to an online marketplace. Truman faced stern opposition from top sales executives, who believed a Condé-owned shopping site would compete against, and therefore alienate, the department stores that spent tens of millions of dollars on print advertising. (Lucky ceased publication in 2015.) A similar fate befell Domino, the DIY decoration magazine founded by Deborah Needleman in 2005. Domino celebrated a proto-Instagram aesthetic of Lucite coffee tables and eye-popping Jonathan Adler–style prints. Early on, when Needleman asked her Condé Nast bosses to hire a web editor, she was told not to bother: her magazine’s budget covered thirty employees, and a web person would be “a waste of a headcount.” Undeterred, Needleman developed a business plan for a website where users could collect images from anywhere on the web and store them in folders, creating custom mood boards for decorating ideas that could be shared with friends. The site, called My Deco File, went live in August 2008. Condé Nast was paying Needleman about $500,000 a year, plus a clothing allowance and a free car—but the company refused to hire a Deco Files support staff. “I was on my own,” Needleman recalled. “No one cared.” Domino, along with Deco Files, was abruptly shut down by Condé Nast five months later, and Needleman left the company. (Condé let her keep the car.)
In 2010, a site called Pinterest, remarkably similar to the one Needleman had envisioned, debuted. In 2019, it went public. In January 2025, its market capitalization was $22 billion.