Founders at Work is a fantastic book with a huge array of internet talent on display, discussing the way their startups worked (and in some cases crashed and burned) in fascinating technical, social and economic detail. This is essential reading for anyone in the area - a few (amazon) reviewers commented that the book lacks analysis - it is true there's no pontification, but all the interviews are structured similarly, so that the analysis is emergent by seeing different gurus give their respective answers to similar questions.
For me, one crucial area is how these folks often didn't have insight into their own success (reasons for) until afterwards! e.g.
how many of the cool companies built 3 (or more) things before they
actually found the thing that made it big? often they didn't even
realize or understand what it was they had that made the thing succeed!
paypal's fraud detection, (not the e-cash)
hotmail's bottom of email banner viral advert/market, not the firewall busting
gmail too: auto-completion, not the search (wasn't even new - i was using
glimpse to search my mail and desktop/file systems for years before)
yeah, even google's click-thru advertising (not page-rank, which was only
marginally better than altavista at stoping people artificially boosting their site)
and, landsakes, RIM started by building realtime LANs before realising Mobile Email might be quite big:)
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