It's an interesting question, but I don't know of any books that
specialize on the mistakes of founders/projects, save for the Mythical
Man Month [1] by Fred Brooks. HN does get a lot of "X is closing down"
submissions, and some of them give interesting reasons for why the
company didn't make it.
On a general level, there are usually more ways to make fatal mistakes than there are ways to make things successful.