It's fun to look at rule breaking entrepreneurs, and imagine ourselves being like them. Who doesn't admire Richard Branson?
The same is true of writers. Stephen King, for instance, can't seem to go for a single page without breaking some rule of grammar, or roasting some sacred cow.
But rule breaking just for the sake of breaking the rules is not a smart idea. Yes, to succeed at extraordinary levels you will probably need to break the rules; but first, you need to understand them.