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Same as the reason for the failure of Upcoming (v1) and underperformance of Flickr: Yahoo & its frothy brew of money plus strategic blindness.

You might also throw the fate of ~pg's Viaweb, once it became Yahoo Stores, into that same class of fumbled opportunities. And so you can read Graham on Yahoo & get a good idea of the issues:

http://www.paulgraham.com/yahoo.html




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