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Do I need to be so uncool as to list all the reasons why New York is cool? It is cool in a way that Los Angeles, with its movies and music scene misses. It’s the edgy edge. London has it as well. Berlin has it. It’s a city thing. Sorry, San Jose and Palo Alto, suburbs are not cool. Provincial cities like Austin and Boston are also not cool. Why does this matter to web technology? Web 2.0 is a consumer wave. The web really is replacing, surrounding, augmenting and extending all traditional forms of entertainment. And to make it in entertainment, you have to be cool, or hot, or whatever is the cool or hot word. Cool is a sustainable competitive advantage. No person can be cool for very long, but a city can be cool for a long time. New York is as cool today as it was when Frank Sinatra was doing his thing or when the New York Dolls were inventing punk music. New York has that unique mix of media, fashion, and money that enables cool to thrive.