Perhaps being the guy no one thinks can win is HELPFUL on the Democratic side. Then you don’t have the old Dem consultant class giving you bad advice, charging you millions and weighing you down.

Look at Uncle Bill — no one would take on Bush the First after his victory in the Persian Gulf War. Clinton was a dark horse, no one took him seriously. Therefore he was ignored by the top-shelf consultants and Bill’s campaign was run by
hungry-time-to-make-a-name-for-myself folks. The Dem establishment picks either evaporated — or, in the case of Gore, became Bill’s running mate.

So — Barack wasn’t weighed down by the top guys, he could make different choices, and he used his local organizing experience to really build an on- and off-line team of passionate supporters.

Understanding community organizing was probably a great help in being comfortable with Web 2.0. After all, you don’t walk into a public housing project and start bossing everyone around about how to create change (believe me, I’ve tried). You listen to a LOT of bitching and you earn trust by being responsive to folks’ concerns, promoting their agenda(s), learning to dovetail them with your own.

Very Web 2.0.

It’s good I don’t have a thing for Trekkie geeks. Especially when they’re Republican.