Miguel Carrasco's Real World has compiled an amazing (and amusing) top 10 list of computer industry losers, some of them beautiful losers, some just plain dogs. Among the case studies in this walk down memory lane are the the Xerox Alto, the Apple Lisa, IBM's OS/2, and Steve Jobs' NeXT machine. And don't forget that old classic, CP/M:
In 1980, IBM finally realized they needed to put a home computer out on the market extremely fast. However they could not find the time to wait around to build their own operating system. They wanted to buy one, and the best one at the time, Gary Kildall's CP/M operating system. Where was Gary Kildall on this fateful day that the IBM suits came knocking? Out of office flying a private plane. IBM went back to the office's and looked up Microsoft, which they thought had a broad license to sell CP/M. Microsoft came in and negotiated a per licenses model to sell the operating system at 50 dollars per machine. Bill Gates had created the Software Licensing Industry!
Carrasco notes out that many of these mistakes (whether of technology or business judgment) paved the way for later successes. For example, the Xerox Alto and the Lisa led to the Mac, which popularized the notion of a GUI-based OS. The NeXT machine was a flop, but went on to become the basis for OSX, and in the hands of Tim Berners-Lee, it played midwife to the World Wide Web.
On the other hand, the less said about Windows ME and Microsoft BOB, the better.