Great cities attract ambitious people. You can sense it when you walk around one. In a hundred subtle ways, the city sends you a message: you could do more; you should try harder.And from footnote : How many times have you read about startup founders who continued to live inexpensively as their companies took off? Who continued to dress in jeans and t-shirts, to drive the old car they had in grad school, and so on? If you did that in New York, people would treat you like shit. If you walk into a fancy restaurant in San Francisco wearing a jeans and a t-shirt, they're nice to you; who knows who you might be? Not in New York.
The surprising thing is how different these messages can be. New York tells you, above all: you should make more money. There are other messages too, of course. You should be hipper. You should be better looking. But the clearest message is that you should be richer.
What I like about Boston (or rather Cambridge) is that the message there is: you should be smarter. You really should get around to reading all those books you've been meaning to.
I'd always imagined Berkeley would be the ideal place—that it would basically be Cambridge with good weather. But when I finally tried living there a couple years ago, it turned out not to be. The message Berkeley sends is: you should live better. Life in Berkeley is very civilized. It's probably the place in America where someone from Northern Europe would feel most at home. But it's not humming with ambition.
In retrospect it shouldn't have been surprising that a place so pleasant would attract people interested above all in quality of life. Cambridge with good weather, it turns out, is not Cambridge. The people you find in Cambridge are not there by accident. You have to make sacrifices to live there. It's expensive and somewhat grubby, and the weather's often bad. So the kind of people you find in Cambridge are the kind of people who want to live where the smartest people are, even if that means living in an expensive, grubby place with bad weather.
One sign of a city's potential as a technology center is the number of restaurants that still require jackets for men. According to Zagat's there are none in San Francisco, LA, Boston, or Seattle, 4 in DC, 6 in Chicago, 8 in London, 13 in New York, and 20 in Paris.
(Also, the comments are amusing, particularly for the one-line descriptions of places.)