This is a really good question and one I ask myself all the time. I also am an entrepreneur and have owned my own businesses off and on for the past 15+ years. During the times that I was looking for work, I also found myself pigeon holed because I was not the "cookie cutter" Enterprise Account Exec for Salesforce then Oracle, etc. It seemed to me that it became a detriment as potential employers see you as a flight risk. I would steer away from being overly entrepreneurial. HOWEVER, with that being said, I wear the entrepreneur title as a badge of honor. I am battle tested, been in the trenches, worked for no money at length and can walk the walk. At the end of the day it is a monetary decision. Good Luck!