From Gail Collins doing the Hillaryland postmortem in this month's Vanity Fair:
Such was the hubris of Hillary’s team that they discounted Obama as a passing pop star to non-voters. Politico.com reported that at a November 2007 Jefferson-Jackson dinner in Iowa, where 9,000 people showed up, 3,000 were already for Obama. “Our people look like caucus-goers,” Mandy Grunwald sniffed, “and his [Obama’s] people look like they are 18. Penn said they look like Facebook.”
“Did they sleep through the 2003–4 election cycle?” asks an incredulous Joe Trippi, referring to Howard Dean and his new form of communication. As the pioneer who kick-started the bottom-up, low-dollar style of campaigning, tapping grassroots organizers and “newbies” for Dean through the Internet, Trippi was appalled that the Clinton machine stuck with a top-down, status-quo campaign. But the Clintons were out of touch with new forms of communication. Bill Clinton still doesn’t use e-mail or own a BlackBerry.
Why hadn’t they been using the Internet all along as a bulging cash register the way the Obama forces were doing? Hillary’s team had held a retreat in the fall of ’07 to huddle with propeller heads from Google and Yahoo, hoping to update their Internet savvy, but basically gave up on trying. “We tried direct mail but we couldn’t come close to him,” admits one member of Clinton’s brain trust. “Obama tapped a different sensibility. They had a more, uh, viral [i.e., spreads by itself] campaign.” The very word “viral” in his mouth sounded foreign.

