Everyone agrees Hughes worked very hard, explained things well, followed up. But as much as anything, he himself became part of what the campaign was communicating: He lent Obama some of Facebook’s kids-from-Tomorrowland aura, merging its story with Obama’s, even though he was never one of the social network’s lead futurists. In May 2007, The Wall Street Journal put him on its front page, his hair a shaggy sweep like Justin Bieber’s used to be. The LOL (but totally off-target) headline: “BO, U R So Gr8.” After a Chicago Sun-Times columnist labeled him a “youthful web legend,” his co-workers in the Michigan Avenue campaign headquarters made him a bright-red sweatshirt with those words on it, which he wore. He knew he was acting as a kind of mascot for tech inevitability.
“This is probably a parallel to Facebook and The New Republic,” says Michael Slaby, who started right after Hughes as the campaign’s CTO, returning in 2012. “There’s a certain kind of—arrogance is not the right word. He brought a bit of that Facebook gravitas to the campaign, that sense of the invincibility of your ideas.”
Post-Obama, some of his ideas didn’t turn out to be so invincible. One was Jumo: With the backing of the Knight Foundation and others, Hughes started the company in 2010, promising that it would do for nonprofits “what Yelp did for restaurants.” The user was supposed to connect to NGOs and charities through Facebook. It quickly proved to be more higher purposeful than practical, and he’s no longer involved.
The more important lesson for Hughes of that start-up was that he wasn’t really a tech entrepreneur after all but a guy whose special talent is the ability to speak in the language of liberal arts to those in Silicon Valley, and in the language of Silicon Valley to those in the liberal arts. And whose humble demeanor, combined with great cyberwealth, allows him to come across as interested rather than domineering. That curious cipher-ness is a mark of success in the social-media era, and people tend to defer to him: Even Stephen Colbert, who had him on to launch Jumo, led him gently through the comedy routine, while Hughes, thrown off his usual bullet points, laughed along. The fact is, people want to see what’s next from him and for him to succeed.
That question is now mixed up with his being a member of a handsome, and quite public, couple. Eldridge, who’s two years younger, grew up in Toledo, Ohio, the son of doctors. When they met, Eldridge had just left Deep Springs College, an all-male two-year institution in the California desert that emphasizes cowboy intellectualism, self-governance, self-denial, and chores. He’d taken some time off to work in Boston before finishing college at Brown, and mutual friends got them together. Among the things the two found they shared was a desire to have, Hughes has said, “a serious impact on the world.”
Eldridge is the less socially limber of the two. He’s far more of a dude than Hughes, and with a narrower set of interests—mostly political. “We’re monogamous, committed, dare I use the word traditional,” Eldridge told the Advocate when they appeared together on the cover. Through a friend, they met Senator Kirsten Gillibrand, who then began to introduce them around.
In December 2009, after the New York State Senate voted down gay marriage, Eldridge quit law school to work with a group called Freedom to Marry. Richard Socarides, who worked as liaison to the gay community under President Clinton and remains an activist, met them around then, too. “Even though they are young, they quickly became among the more prominent funders of gay-rights causes in the country,” he says. Hughes and Eldridge donated $250,000 to Freedom to Marry; Eldridge was named its political director.
They threw fund-raisers for politicians and dinners for notables at their apartment on Crosby Street (or “venue,” as one politico who’s been there for events and dinners calls it). And their efforts helped Governor Cuomo pass the state gay-marriage bill through the legislature. Guests the night it carried included Charlie Rose, Tony Kushner, and Nation editor Katrina vanden Heuvel. Their marriage, last summer, was a kind of political celebration. Senator Schumer did his best Saturday Night Fever finger-point on the dance floor in full view of Zuckerberg, Sean Parker, Cory Booker, Gayle King, and Mo Rocca (who came as someone’s date). When I ask Hughes if he thought that the event was, perhaps, a bit much, he looked like that hadn’t crossed his mind. These are the people they hang out with, he says. “We’ve seen Nancy Pelosi twice since then, once at her house in Napa. It was sort of like most weddings in that regard: It was a convergence of many worlds.”