The team had elite and, for tech, senior talent — by which I mean that most of them were in their 30s — from Twitter, Google, Facebook, Craigslist, Quora, and some of Chicago’s own software companies such as Orbitz and Threadless, where Reed had been CTO. But even these people, maybe *especially* these people, knew enough about technology not to trust it. “I think the Republicans fucked up in the hubris department,” Reed told me. “I know we had the best technology team I’ve ever worked with, but we didn’t know if it would work. I was incredibly confident it would work. I was betting a lot on it. We had time. We had resources. We had done what we thought would work, and it still could have broken. Something could have happened.” …
We now know what happened. The grand technology experiment worked. So little went wrong that Trammell and Reed even had time to cook up a little pin to celebrate. It said, “YOLO,” short for “You Only Live Once,” with the Obama Os.
When Obama campaign chief Jim Messina signed off on hiring Reed, he told him, “Welcome to the team. Don’t fuck it up.” As Election Day ended and the dust settled, it was clear: Reed had not fucked it up.
The campaign had turned out more volunteers and gotten more donors than in 2008. Sure, the field organization was more entrenched and experienced, but the difference stemmed in large part from better technology. The tech team’s key products — Dashboard, the Call Tool, the Facebook Blaster, the PeopleMatcher, and Narwhal — made it simpler and easier for anyone to engage with the President’s reelection effort.