Cory has a great article (it sounds like it could/should be a conference keynote address) at O'reillynet about the intersection of internet reliability and the business world. I remember at KnowNow, we used to have a lot of arguments about what the term "reliable" meant to users and potential customers. The people that matured during the age of the web figured "works most of the time" was sufficient uptime for an internet or intranet service, while the people from the software age argued that everything the company did had to be "enterprise class" and it meant paging four people if the network response time varied by more than 100ms. Cory's article discusses the folly of such an attitude.
It also reminded me of an old mantra that could also explain why napster worked, why buggy implementations win out if they work most of the time, and why windows became the dominant OS on the desktop: Worse is Better.