Paul Graham’s most recent essay touches on what a city says to you. One few points stood out: NYC is expensive, and unless you’re donning a suit, most wont take you seriously.
This suggests an answer to a question people in New York have wondered about since the Bubble: whether New York could grow into a startup hub to rival Silicon Valley. One reason that’s unlikely is that someone starting a startup in New York would feel like a second class citizen.  There’s already something else people in New York admire more.
In the long term, that could be a bad thing for New York. The power of an important new technology does eventually convert to money. So by caring more about money and less about power than Silicon Valley, New York is recognizing the same thing, but slower.  And in fact it has been losing to Silicon Valley at its own game: the ratio of New York to California residents in the Forbes 400 has decreased from 1.45 (81:56) when the list was first published in 1982 to .83 (73:88) in 2007.
Sad, but true. He talks about Cambridge, MA (Boston) and Silicon Valley, CA. Being raised in the great city of NY, I’ve always thought this, but never had any real evidence. Comparing a Forbes lists from 1982 to 2007 is a start. Anyway, it’s a good read, check it out.