“Time is precious,” Hughes tells me over coffee at the Library bar at the NoMad hotel—someone’s Wi-Fi-enabled, book-lined Edwardian fantasy. (He loves the place.) Maybe some of his unslackerishness—he seems to have completely skipped his feckless twenties—comes from the fact of his parents being older (his father turned 80 this year). Certainly being the son of a traveling paper salesman and a public-school teacher in an area that was once said to produce over half of the country’s furniture and now markets itself as an ideal home for data centers (Google, Apple, and even Facebook operate server farms there today) would quicken your appetite for neo-Balzacian self-invention. “I didn’t feel like I was necessarily in sync with a lot of people I was around,” Hughes has said, with some understatement. “He hates where he’s from with a passion,” observes an acquaintance.
While at Andover, Hughes polished away his accent (though it can come back a bit, sweetly, when he’s comfortable with a person) and conservative religious upbringing, became president of the Young Democrats, and came out of the closet. He was also the news director of the school paper and, in his senior year, he wrote that melancholic but determined essay, titled “Deprived of Indulgence, but Granted an Edge.” It is mostly in the first-person plural—a defensive posture for a guarded young man—and describes how students at the school coped “by working harder or doing more activities, distancing ourselves from the persistently returning loneliness, hesitancy and confusion.” As for what Andover did for them: “It has shattered any hopes of a pure world of perfect beauty and of complete success in its teaching us—even though perhaps inadvertently—that we are condemned to live in a world with flitting moments of satiation … Whether we wanted it or not, we have the edge.”
Olivia Ma, today the news manager at YouTube, remembers seeing him in the cafeteria his first week at Harvard, when she was recruiting for Current, a collegiate newsmagazine. Even as most freshmen looked away, she remembers, “He locked eyes with me.” Hughes joined, and later he and some friends also started Queer, a gay-culture journal.
Sophomore year, Hughes found himself in one of the smallest suites in Kirkland House with Zuckerberg, Dustin Moscovitz, and Zuckerberg’s eight-foot-long whiteboard. At the time, Hughes didn’t have much interest in computers but soon was swept up. He and Zuckerberg were an unusual pair: Ben Mezrich reports in The Accidental Billionaires that Zuckerberg nicknamed Hughes “Prada” because he dressed fashionably. According to David Kirkpatrick’s The Facebook Effect, in addition to selling the site to the press, Hughes helped Zuckerberg appreciate the user’s perspective and had such a hold on his roommate that Zuckerberg would often marshal Hughes’s arguments to make a point. After Harvard, Hughes worked for a time at Facebook, then in Palo Alto—the company preferred that employees live within a mile of the office—and became one of the only nontechnical people there with any real authority.
Another then-employee, Katherine Losse, published a memoir of her time in Palo Alto called The Boy Kings. She always felt that her own skills, as an English major, were considered “woefully unscalable” in a company whose founder, Zuckerberg, listed in his own profile, under “Favorite Books,” “I don’t read.” For unscalables like her, Hughes was a beacon of hope: He’d talk about James Baldwin, and when she moved into his former apartment in a Deco building, he even mused with her about the lives of the people who used to live there—not something the programming people were programmed to do.
“In stark contrast to these boys who were on the floor playing with their trucks,” Losse says, Hughes “was the 50-year-old man in nicely cut jeans and a little sweater.” His hygiene was much better too.
Most got-in-on-the-ground-floor digital millionaires get bored or frustrated, jump ship, and go cook up new tech schemes. Hughes decided to join another type of start-up: the Obama campaign. It turned out to be quite scalable. (The then freshman senator’s “body man,” Reggie Love, had worked with Hughes to help create Obama’s first Facebook profile.) “He didn’t seem overtly political, and he still doesn’t,” notes one Washington operative who met Hughes around then and still knows him. “But he’s been drawn into that world to seize the opportunity.”
Amid the decorative stacks at the NoMad, I ask him why he left Facebook for Obama. He sighs. “There were several factors at play,” he explains carefully. “I really wanted to do something that had a direct and positive impact on the world, and though Facebook has had a positive impact on the world, Facebook doesn’t have any normative disposition. It’s a company that’s trying to connect people so they can share, but what they’re sharing is up to them.” Bullet point: He wanted meaningful work. His project, my.barackobama.com, applied some Facebook lessons to make campaigning more “user-centric.”