Looking back, I think if YC had existed, I almost certainly would have applied. But nothing like that existed back then and so I wound up making my own mistakes and then writing about them.
I've always thought that it's not entirely good idea to not make your own mistakes. While painful it provides a better gut than simply being told or reading about things and getting quick answers.
You know in traditional businesses there is a reason that even in many cases family members (in family businesses) spend time at the bottom before they are put into higher level positions. It gives you a chance to see exactly why and how things are done and to experience them and fully understand nuance. Things that can't be learned in school or passed by anecdote.