I suppose there are correlations between his life and founders. He failed as a political cartoonist right out of college, and failed for a couple of years drawing C&H...not a lot of newspapers wanted to take his work.
The most amazing thing to me, though is that he chose a stopping point. He stopped C&H at what one might call the pinnacle of his popularity because he felt he had completely explored what he wanted to explore with the medium, unlike those long running one-liner and uninspired strips like Garfield.
Software might be amendable to the same time of attitude--they only should go up to a certain point, instead of add feature after feature, ad nauseum, creating an uninspired pile of features.
It might be like how the Ilwrath just got a little bit too good and wrapped around to evil.