ROB GREGORY’S career is, among other fine things, a case study in how to survive the media anarchy of the twenty-first century. Now he sits upon a lofty digital perch—that of chief revenue officer of WhoSay, a revolutionary celebrity social media company that we shall learn about soon. But his work life began among those traditional objects called magazines. He clambered up the print-world ladder with athletic grace, going from advertising director of Gourmet in 1993 to launch-publisher of Travel & Leisure Golf in 1998 to publisher of Rolling Stone in 2000—“when it was still a real arbiter of the culture.” Gregory flashes his boyish grin and says, like you or I would say, “Just having a business card that said ‘publisher of Rolling Stone’ on it was pretty cool.”
Then things got a little strange, though in an interesting way. In 2004 Gregory won the job of group publisher at Maxim. Remember Maxim? For a while it reigned atop the men’s category, displacing Esquire and GQ with its gleefully unreconstructed “beer and babes” ethos. The king of the Maxim empire was a Brit named Felix Dennis, a sort of wild-haired, crack-addicted, poetry-obsessed Hugh Hefner. For all his unruliness, Dennis was a publishing savant. “He was able to time the zeitgeist perfectly,” Gregory says. “Maxim was probably the second most profitable magazine in the country, after People. It was tribal, how much guys loved Maxim. It defined their natural habitat. It was the antidote to political correctness. Guys could be guys on their own turf, on their own terms. It was like a movement.”
Then, almost overnight, it wasn’t. “We ran smack up against broadband Internet,” Gregory recalls with a vestigial grimace. “All of a sudden the jokes, the humor, the girls, the gadgets, the cultural irreverence, all of those things were in your in-box every day.” Dennis wisely unloaded the U.S. edition of Maxim in 2007; it has since changed hands twice again. The magazine struggles bravely on, but its mojo has long since floated away. “It’s completely irrelevant now,” Gregory says with a wave of the hand. “It’s an afterthought.”
Maxim’s story is not unique. During Gregory’s four years there, he witnessed the arrival of Facebook, YouTube, Twitter and the iPhone—four horsemen of the print-world apocalypse. The tipping point, he believes, came in 2005, the year dial-up Internet access ceded dominance to broadband, which let moving pictures, graphics and sound flow instantaneously to our computers. The smartphone then swooped in, making this brave new world portable—to the point where the dominant public posture has become the bent-necked squint. How could magazines compete?
Gregory does not side with those who believe print is dead. “I think there are some very well-niched magazines out there. GREENWICH magazine is a great example. So is Vogue. So is Men’s Health. They’ll survive in print for, I don’t know, at least another generation.”
But he did watch the magazine ecosystem shrink alarmingly as ad dollars flew off to the Internet. During that capricious decade, popular magazines in all categories dropped to the great windowsill in the sky. A small sampling of closures includes Metropolitan Home, Blender, Nickelodeon, Portfolio, Teen, PC Magazine, Men’s Vogue, Playgirl, Jane, Premiere, and Gregory’s alma maters Travel & Leisure Golf and Gourmet. A great many others, notably TIME and the rest of the newsweekly category, saw their influence diminish sharply.
We can thus imagine Rob Gregory circa New Year’s Eve 2008, standing at a bleak crossroads. He was then approaching fifty, an age when most of us no longer want to learn new tricks. That spring, Gregory left the slumping magazine industry to join Plum TV, a PBS-like cable network started in 2004 by Greenwich resident and Nantucket Nectars cofounder Tom Scott. Plum should have been a savvy career move: Targeted to the affluent and “dedicated to the best things in life,” the network won high praise in its markets—Nantucket, Martha’s Vineyard, the Hamptons, Aspen and Miami. And Gregory took well to his new medium: “The good ones are not just salesmen,” Scott observes. “They’re skilled communicators. Rob could package and deliver an idea as well as anybody I’ve ever seen.” But his timing was awful. The Great Recession hit in the fall.
LIFE OF A SALESMAN
Gregory, an affable, quick-witted, live-wire man of fifty-seven, brews two cups of coffee and takes a seat at the island counter in his sunny kitchen. He lives in a lovely stone-and-shingle Colonial in Old Greenwich with his wife, Linda, a cofounder of Cyber Shop, an online department store, and their daughter, Kendall, a senior at Greenwich High School. There’s also Franklin the Dachsund, who, bored with the adult conversation, wanders off to bark some well-meaning advice at a work crew taking down a tree in the front yard.
Gregory’s career path has been somewhat accidental. He grew up in Briarcliff Manor, New York, the son of Al Gregory, a textile salesman, and his wife, Carolyn; but he saw his dreams personified in his uncle and namesake, Robert F. Gregory, an ad man who handled the Pepsi account for the storied agency Foote, Cone & Belding. In Rob’s early teens, advertising still had the glamour we associate with Mad Men, combining the creativity of the artist and the glitz of the high-end businessman. But by the time he stepped out of Boston University, in 1980, some of the bloom had come off the industry and the economy was sluggish. With ad jobs scarce, Gregory landed at McGraw-Hill’s Popular Computing magazine.
Magazines, Gregory discovered, allowed him to exercise a surprising degree of creativity in pumping up a brand. He would later preside over Rolling Stone’s turnaround—at a time of plummeting revenues in the music industry—and produce the fattest issue ever, “the 500 Greatest Albums of All Time.” At Maxim, he oversaw annual profits of $50 million and monthly newsstand sales of $2 million—plus the advent of Maxim Radio on Sirius XM—before the digital shadow fell.
A few print magazines, like The New Yorker, Wired and Forbes, managed to excel in the newly dangerous habitat by creating vibrant web presences. (A New Yorker subscriber, for instance, can go online to access extra stories, blogs, podcasts and archives—an enormous value added.) Today it’s the aim of every wide-circulation magazine to stay relevant with digital editions and extras. A curious variation on the print-digital hybrid was the marriage of The Daily Beast website and the tottering Newsweek magazine. Tina Brown, former editor of Vanity Fair and The New Yorker, started The Daily Beast (named for the newspaper in Evelyn Waugh’s novel Scoop) in the fall of 2008, backed by media billionaire Barry Diller. Brown described The Daily Beast as “a speedy, smart edit of the web from the merciless point of view of what interests the editors.” Its brash take on the news found instant popularity.
Two years later, Diller and Sidney Harman—the stereo magnate who had just bought Newsweek for $1 from the Washington Post—formed a partnership called The Newsweek Daily Beast Company. The deal made sense on paper. It gave Diller a foothold in print with a prominent brand and access to the White House, the Kremlin, and other loci of power, and it gave Harman a sorely needed dose of digital cool. But when Newsweek and The Daily Beast failed to mate felicitously, they called in Rob Gregory. “Rob likes nothing more than a battle with high stakes,” Tina Brown says by email, “so he plunged right in.”
Gregory saw that the digital half of the business was sound. “The Daily Beast had its own attitude,” he says now. “It was ferocious, it was irreverent, it had Tina’s ‘high-low’ signature, which she used to do at Vanity Fair: the salacious with the highbrow, and the gossipy with the serious. She’s just brilliant at that. The Daily Beast was tracking to be a great business and a great brand.”
Newsweek, on the other hand, was going nowhere fast. Brown recalls, “The bottom dropped out of the print advertising market within months of the purchase. The sales staff were walking into offices where the first words were ‘The magazine is so improved, but we aren’t buying print.’ Even worse was the frequency [of publication]. We used to curse that the title ‘Newsweek’ made it hard to turn it into a monthly, a frequency which could have worked.”
By the time Gregory got there, in the fall of 2011, recovery was probably impossible. “Newsweek and The Daily Beast, rather than mesh cohesively, just kind of clanked against each other,” he says. “It was just a colossally bad idea.”
But Gregory did have his victories. One was to put out a retro Mad Men-themed issue of Newsweek—Brown’s idea, capitalizing on the TV series’ ballyhooed return after a hiatus in 2011. The issue included a perceptive father-son portrait of Mitt and George Romney by speechwriter David Frum (Mitt was then running for President, and George had run in 1968) and sixties-style ads featuring still-thriving businesses like Dunkin’ Donuts, Estee Lauder and Johnnie Walker. “We even used the old Newsweek typeface and vintage drawings,” Brown notes. “It was a perfect flashback with modern content, one of the best things I ever did as a magazine editor, and Rob did an incredible job of marketing it and making it our most profitable issue. Rob always loved a high concept to sell.”
“It ended up being one of the coolest things I’ve ever done in my career,” Gregory says. “The ad agency creatives loved that show, and they went crazy designing ads for the Mad Men issue of Newsweek. We had a launch party, John Hamm and the whole cast of the show were there, January Jones, it was fantastic.” He shrugs, smiles. “It turned out to be a dead-cat bounce, because Newsweek was dying.”
It might come as news to some readers that Newsweek never actually died, despite Barry Diller killing the eighty-year-old print edition on December 31, 2012. A chaotic 2013 saw Brown and Gregory leave the company and Diller sell Newsweek to International Business Times. IBT revived the print edition in 2014, but did so with a cover story claiming to have unmasked the elusive founder of bitcoin. It got the wrong man.
And so we find Gregory having passed through an extended period of turbulence—Maxim, Plum and Newsweek Daily Beast—wondering what the devil comes next. But he always had a remarkable ability to adapt. “It’s uncanny how he can metamorphose into the ‘product’ that he works for, whether it’s Scientific American or Gourmet or Garden Design,” says his wife, Linda. “He’s almost a chameleon in that way.” (She took special delight in the Gourmet and Garden Design phases of Rob’s career, since he brought his work home in the form of passionate hobbyism.) Tom Scott adds, “He’s an innately curious guy who’s pretty tuned in with where the world is going. A lot of people will hold out, waiting for things to come back. I’m not sure anything’s coming back.”
Gregory, thinking likewise, willed himself to embrace the digital. “There were times at The Daily Beast where I would just smile during meetings, and I’d be thinking, I have no idea what that person just said,” he admits. Though by the time he got to WhoSay, he’d learned enough to be “dangerous.” “To be totally honest, I’m not sure I moved into digital because I wanted to. I kind of had to, because I saw the writing on the wall. Not only did I have to get out of my comfort zone, I had to get firmly into my discomfort zone for a couple of years. You spend twenty-plus years thinking analog, and then it’s like going into an ice-cold shower.”
If going digital was Gregory’s plank-walk into the cold, it was also, in the end, exhilarating. WhoSay lives at the intersection of celebrity and digital culture. Its various dimensions, however, are not easy to put across in ten words or fewer. “Yeah, the elevator pitch,” Gregory says with a sigh. “When I was publisher at Rolling Stone, it was easy. WhoSay is a lot tougher.” He describes it as part publisher, part talent agency, part social media company, part celebrity company and part data company. “I had to figure out how all the pieces of WhoSay worked, which took me six months, and then I had to figure out how to assemble those pieces into a coherent story that a brand manager at, say, Proctor & Gamble could understand. I had to dumb down a very complex offering.”
Let’s begin with the WhoSay app. Company founder Steve Ellis, a former rock guitarist and online music entrepreneur, developed the app in 2010 at the behest of talent giant CAA. With one tap of a key, it lets celebrities post their content—videos, pictures, commentary—to any social media they like, plus People.com and the Huffington Post. (The content also gets posted to WhoSay’s own site, whosay.com, which Ellis likens to “a People magazine written by the people themselves,” but would probably strike most as a cross between Facebook and Buzzfeed.) Tom Hanks was the first big celebrity to sign on. Matthew McConaughey, Sofia Vergara, Kevin Spacey, Bill Maher, Common, Reese Witherspoon, Buzz Aldrin, Chris Rock, Gwyneth Paltrow, James Taylor, Neil Gaiman, and about two thousand others quickly followed.
WhoSay curates the image it projects with surprising deliberation. Not any celebrity can join, for instance; one has to be invited. “We want the whole thing to be premium,” Gregory says. “That’s why we don’t work with Justin Bieber and Miley Cyrus and Kanye West and all that stuff. We want it to be quality and smart.” It’s not that WhoSay is allergic to controversy. It published a series of essays by Caitlyn Jenner about her sexual transformation. And celebrities are never discouraged from speaking their minds, especially in political season. Bette Midler: “Game of Thrones returning soon! As a story of aggressive power struggles, it reminds me of the GOP primary. But a whole lot more civilized.”
But what makes WhoSay revolutionary? In “the wild, wild West” of digital space, Gregory says, WhoSay copyrights all the content created by the celebrities. “The big idea there was that celebrities had been monetized by other parties for a hundred years. The gossip press, paparazzi, TMZ, all these things. Now the Internet and the smartphone can give them the power not only to control their narrative and build their brand, but to literally own their stories. This has never happened before. If Matthew McConaughey took a selfie at the Oscars and the picture blew up, he would own the intellectual property. Paparazzi couldn’t sell it, or People magazine couldn’t run it on the cover without his permission. So it was a power-giving tool for celebrities, was the original idea.”
Sooner or later, one must ask how WhoSay makes any money, since its celebrities pay no fee to join and its website is uncluttered by ads. “The plan was to organize all the social content from the celebs into a single website, and sell banner ads there, sharing the money with the celebs,” Gregory says. “But we soon realized the days of websites and banners were over.” Banner ads? One is said to be more likely to survive a plane crash than to click on one intentionally. Websites? They’re “over” in the sense that people aren’t likely to stumble upon them in the mega-numbers that advertisers covet, especially in the app age. It’s social media that gets the heavy traffic. “So we focused on creating custom, branded content campaigns, distributed to the Instagram and Facebook feeds of fans.”
This is where WhoSay really breaks new ground—beginning with its fastidious, Moneyball-like aggregation of fan data. Gregory opens his laptop for a demonstration of what might be called the science of celebrity. “This is McConaughey’s app,” he says. The actor talks about football, children’s causes, and, if you look a little deeper, beer. “We sift through and see what content that he creates and shares with his fans resonates the most—what his fans are commenting about it, who his most vocal fans are, who his most influential fans are.”
Fan “engagements”—likes, comments and shares—begin to build a precise portrait of a celebrity’s marketing appeal. Say you like Alec Baldwin. Say too that your social media activity shows an affinity for Chevy. Then, combing through the social media IDs it collects, WhoSay discovers this overlap and uses it as a gateway to the next dimension of its business: targeted social media advertising campaigns.
WhoSay campaigns are not traditional ad campaigns; they can take the form of anything from arty interviews in cool settings to good-natured pranks. Last year, for example, Chevrolet approached WhoSay about doing an April Fool’s Day media stunt known as a “culture bomb.” The idea WhoSay came up with, called “Best Day Ever,” was to have celebrities appear unannounced in college classrooms to guest-teach. Alec Baldwin dressed up as Abraham Lincoln, strutted into a history class at Occidental College, and delivered a lecture, to the surprised delight of the students. The video traveled to Baldwin fans’ social media feeds, got shared and went respectably viral. The strangest thing? Baldwin never so much as whispers the word “Chevrolet” (though we do see Chevy T-shirts getting tossed to the students in the final frame). Actors Norman Reedus (The Walking Dead), Nikki Reed and Ian Somerhalder (The Vampire Diaries), and Olivia Wilde (Vinyl) also took part in the Best Day Ever campaign—and their videos went viral, too.
“That’s the eureka moment,” Gregory declares. “That’s where the brands say, ‘Wait a minute. Not only can you create this great storytelling, use the data to cast the right people to tell the story, and get it to people who have already identified themselves as fans of Alec, or whoever—but you can validate that they saw it.’ As opposed to you or me watching a football game and when the commercials come on, we go and make a sandwich. That’s the old world, and it’s giving way to this world.”
WhoSay now counts BMW, McDonald’s, Diet Coke, Remy Martin, Bank of America, Dunkin’ Donuts, Dodge Ram and Toyota among its clients, and new business is pouring in after a quiet first couple of years. “WhoSay is on a gallop,” Gregory says. “We’re crushing it. And I’m so glad, because it could have gone either way.”
Recognizing that the nature of celebrity is changing, WhoSay now courts not just celebrities but cultural “influencers”—for example, young YouTube stars like comedian-blogger Lilly Singh, whose videos have received over a billion views. Talk of influencers puts Gregory in the mind of Rolling Stone founder Jann Wenner. “Jann used to tell me, sort of wistfully, ‘I once had the power, every two weeks, to decide what the coolest thing in America was.’”
No entity can do that anymore. To the dismay of advertisers and traditional media executives, the culture is different now, fragmented by an explosion of choice. But Gregory believes WhoSay, with its network of admired people reaching the young where they live, has the best shot at doing what Rolling Stone once did—validating what matters in the culture. He foresees the network growing to include physicists, leading journalists and the like, “people of substance and influence.” That is the hope; but who knows? “It’s a new age,” Gregory says. “And we’re all kindergarteners again.”