You don't need to teach people to break all the rules. That's not what you want. You want people to take calculated risks, and break the rules that need breaking.
You could teach the history of rule-breaking, and explain how why those rules needed to be broken. Teachers could do that pretty well.
Entrepreneuship is not a really "calculated risk", its a deeply uncalculated one on the contrary: leave your job (or your normal career track), get no revenues for an undefined while, bet most of your credibility on idea that may change or become irrelevant, etc...
Teachers can tell stories about all of those, but they won't really "teach" them, since there are too personnal to be replicated.
You don't need to teach people to break all the rules. That's not what you want. You want people to take calculated risks, and break the rules that need breaking.
You could teach the history of rule-breaking, and explain how why those rules needed to be broken. Teachers could do that pretty well.