Merrill Chapman's book, In Search of Stupidity: Over 20 Years of High-Tech Marketing Disasters, is a guilty pleasure. Chapman has tiptoed through the tulips of high tech over the years -- he was a group product manager of WordStar at MicroPro, product manager at Ashton-Tate, and a consultant to Microsoft, Novell, Teradata, and others. The book is his recounting of high-tech marketing disasters he was involved with, as well as others, such as Microsoft vs. Netscape.
It's funny in parts -- and having worked in high tech for 30 years, all too accurate -- but it's also snarky. In retelling the stories, Chapman often comes across as the only bright one in the room -- everyone else makes mistakes he avoids. Part of this comes from hindsight -- how things were going to play out were not apparent at the time. Consequently, Chapman's judgments get shakier the closer he gets to today. For example, he disses Software as a Service after the dot.com bust, but doesn't predict its current resurgence.
In short, a funny read that needs to be taken with a grain of salt.