As an entrepreneur, try to be a subversive, not a rebel.
Here’s how I differentiate between the two:
1) A rebel breaks the rules because he or she hates being told what to do. A rebel’s defiance is open, and being identified as a rebel is a feature, not a bug.
2) A subversive breaks the rules because he or she is trying to accomplish a goal, and breaking the rules is the best way to accomplish that goal. A subversive’s defiance may be secret or open, depending on which is most likely to help accomplish the desired goal.
Subversion is rebellion with subtlety and purpose.
Napster was about rebellion–it was clearly illegal and the company didn’t bother concealing it.
Pandora was about subversion–finding a loophole around streaming royalty rules.
Rebellion can change the world, but it often flames out. Subversion is subtler, but has a higher chance of success.
(This post inspired in part by a conversation with Martin Bogomolni)