Alpert—a small man with an impish grin who goes most places in shorts and sandals—works out of the cheerily blue-painted Church Street NW rowhouse he bought for $1.3 million in 2008. The bookshelves are lined with science fiction, old math textbooks, and seminal works on urban planning. His home office has one map of D.C.’s Comprehensive Plan and another of the District’s World War II-era downtown. His laptop is plastered with stickers of his own creation: The iconic Obama logo, one with a stylized train coming out of the center, and another with two “O”s as the wheels of a bicycle.
For all his big-city urbanism, Alpert started life in the most suburban of places: Acton, Mass., the son of a lawyer and a homemaker who did interior design on the side. Early on, his father brought home an Apple IIe, which little David used to learn programming instead of playing games. Though interested in government, Alpert studied computer science at Harvard, figuring he’d rather write code than write history papers.
Graduating at the height of the tech bubble in 2000, he joined a startup and moved to Silicon Valley. The enterprise tanked, but Alpert landed on his feet as a project manager at Google. (The little intra-site bullets that come up under each homepage when you Google something? Alpert made those.)
Within a few years, though, the monoculture of Google’s suburban Mountain View, Calif., campus became stifling. Alpert convinced the company to let him move to its New York City office. At a 2004 State of the Union watch party in Manhattan, he hit on his first foray into Web organizing: The early form of Drinking Liberally, a group of lefty friends who got together to imbibe and commiserate at the height of the Bush administration. (Alpert, who doesn’t drink much, is proof that you don’t have to be an alcoholic to join). In his spare time, Alpert built the website for what would become Living Liberally, a social-political organization with chapters all over the country.
“He immediately got it,” says founder Justin Krebs. “His role was thinking about how to build something that could scale nationally.”
In 2007, Alpert’s future wife Stefanie got a job in the D.C. office of law firm Wilmer Hale. The couple decided to move, and Alpert left Google behind. “When I started at Google, if you had an idea, you could run it by Larry or Sergey at lunch,” Alpert says, referring to company founders Larry Page and Sergey Brin. “By the time I left, it was 15,000 people, and there was a lot more process…Getting a product done was more about navigating this process and navigating the bureaucracy or the competing interests, as opposed to spending your time coming up with ideas.”
Of course, it wasn’t quite as scary for Alpert to quit his job as it might be for most people: Though he declined to elaborate on his personal finances, let’s just say that six years at Google left Alpert sufficiently well off that he wouldn’t need to scour the want-ads for a long, long time.
Alpert’s first idea for using his stock-option-subsidized free time was a failure. Building on the Google ethos, he started a blog called IPac with the goal of advancing Internet freedom; one campaign involved sending iPods to recalcitrant senators so they could appreciate the value of downloadable music. With insufficient enthusiasm, IPac fizzled, and Alpert needed a new project.
It arrived in the form of a void: D.C. had development blogs and neighborhood blogs, but nothing like a Streetsblog, the influential nonprofit-funded website that focuses on progressive urban planning and design. Urban geekery had become a side interest of Alpert’s in New York, where he absorbed knowledge about the city’s subway system and worked on efforts to rethink Park Slope’s pedestrian-unfriendly Grand Army Plaza. He read books by Jane Jacobs, the pioneering grassroots activist who fought 1960s urban renewal and extolled walkable, 19th-century neighborhoods. So in February 2008, Alpert designed a website, posting several items a day on things like traffic waves and environmental impact statements.
GGW grew steadily from there. National bloggers who Alpert knew from his netroots life, like Matthew Yglesias and Duncan Black—a.k.a. Atrios, who writes at Eschaton—drove traffic his way. A popular early feature was a series of fantasy Metro maps, depicting the transit system with extended lines and different options. At one point, WMATA’s director of long-range planning asked if he could use one of them for a presentation; Alpert gladly obliged.