Basically, it was developed and tested internally. Features that came about because of other design decisions were seen as fantastic and clever. Googlers assumed The Great Unwashed would find the same features amazing.
They didn't. Cue corporate stumble.
In all likelihood, Jobs was probably quite serious when he said "don't hold it that way". The Applers around him would not have had a problem and would be capable of re-training themselves. Unfortunately, The Great Unwashed are rather further away from his RDF than his employees and this created a disconnect between the two realities.
Jobs has done a lot of great things for Apple. But that's only part of the story.
Wade.