The NY Times proposes a technological metaphor and asks "Is Obama a Mac and Clinton a PC?" It's not hard to see the analogy - Obama is young and hip, Clinton is the establishment candidate.
But I think a better analogy is between the candidates and search engines. In this comparison, Clinton is Yahoo and Obama is Google. I like both sites and I use email at both. I started out at Hotmail (which I still use), switched to Yahoo, and just recently started using Google. The differences are clear. Yahoo is superior to Hotmail, which feels a little creaky at this point, but Gmail is much better than Yahoo (except that Gmail, for reasons that seem to be utterly inexplicable, does not use folders. It uses "labels" to sort emails. I find this very frustrating.)
Clinton and Yahoo are both products of the 90's. They were both insurgents once upon a time. Both have become, in a very short time, the embodiment of a traditional way of doing things. Obama and Google, on the other hand, are both products of the 21st century. Both came from nowhere to challenge the established order.
Clinton and Yahoo both made the mistake of taking their supporters for granted, and not empowering them. I like Yahoo for a lot of things. I buy all my domain names through it, because it's ridiculously easy. I once bought dingbathermeneutics.com because I thot that sounded cool. But this blog is hosted at Blogger, which is owned by Google. I use it because I tried to set up a blog on Yahoo, and ended up feeling totally overwhelmed by the technical details. Blogger makes maintaining a blog very easy.
Clinton and Yahoo have both concentrated on media rather than technical superiority and executing a superior strategy. Hillary assumed that the air campaign, i.e. advertising, would win her the nomination. Obama, the former community organizer, understood that having people knocking on doors in their neighborhoods and making phone calls for you is vastly more effective than just paying for ads. His ground game, which requires more attention to detail, is better. Yahoo made the same mistake that Clinton did - they hired Terry Semel, a movie studio executive, to run the company. The Yahoo home page is chockablock with media items that visitors can click on and watch or read. It's a good strategy - I occasionally click on things I see there. And Hillary's strategy would have been a good one as well - if Barack Obama hadn't had a better one.
Google's strategy is obviously different just from the home page, which is almost pristine. No clutter or mess there! Unless you have an iGoogle page. But behind that pale facade, Google is much more technologically advanced than Yahoo. Most important, Google uses the technology to empower users. This blog is a great example. I once even almost sort of kind of had a blog at Yahoo - I had a Geocities account for years. But I put up all of two posts before I abandoned it, and that was years ago. Yahoo paid a fair chunk of change for Geocities way back when, but then never did anything with it. Even after other social networking sites like Friendster, MySpace or Facebook took off, Yahoo let Geocities languish. Google, of course, owns YouTube, one of the best user-enabling Web sites ever.
Obama's Web strategy, as the Times article points out, set the standard for empowering volunteers, giving them the tools to connect with other Obama fans, set up parties, raise money, etc. Very Googlish - develop cutting-edge technology, and let it loose into the world for the masses to have fun with it.
How far can I take this analogy? I'm only vaguely familiar with the different technologies that each site uses, but what I do know is that Google takes advantage of the networked aspect of the Web to find Web sites - the more links to something, the higher it is in the Google results (or so I understand). Obama's campaign is, again, something like this - by empowering individuals, it encourages them to take advantage of their own, preexisting, networks. Clinton, on the other hand, took advantage of the network that she and Bill have. That's incredibly extensive, but there are limits to how many people a couple can connect with. The Clintons have a great machine, but Obama's campaign was more organic. And it blossomed, when the Clinton's machine started to break down.
I actually got an email from Yahoo the other day about my Geocities account. It was a notice that, since I haven't used it in years, it will be deactivated in three days if I don't do something with it. Apparently someone at Yahoo is cleaning house, clearing out the old Geocities accounts that have been taking up server space for years. It's about time.
And now Microsoft wants to buy Yahoo. I have no idea why, but I'm not optimistic - Microsoft doesn't exactly have a great reputation for moving fast these days or for empowering users. Maybe Yahoo and Hillary Clinton's Presidential ambitions will have the same fate this year, one disappearing forever, one being absorbed into a vastly larger enterprise. Personally, I would be psyched if Apple bought Yahoo, but I doubt that's going to happen. All I know is that I ignored the email from Yahoo about an account I had almost forgotten that I had. Go ahead, delete my Geocities account. I like Yahoo. I have a lot of respect for Hillary Clinton. But I live in the 21st century.