I would like to hear the stories of startups that created a software product of any category that didn't take off for the simple reason that no one wanted it. One of the examples could be Microsoft Bob. Can you please share a similar story?
Check TC's Deadpool section
Apple is a great candidate for answering this question because so many people think of Apple as the 'can't miss' company that always wins. Not true!
Here's a great article on Top 10 Apple Products that flopped.