I've experienced this sort of thing first hand many years ago. After ten years running my own tech startup I decided to go get an engineering job and "depressu

I've experienced this sort of thing first hand many years ago. After ten years running my own tech startup I decided to go get an engineering job and "depressurize". I could not land one. I did not understand what was going on until an HR person clued me in. The message was that with the Internet you can't escape your past. You can't dumb down a resume for the practical purpose of getting a job. If you've been an entrepreneur with any degree of success (or even failures) you are one search away from someone knowing as much about you as they care to. You typically run into two scenarios. The first is a manager --your would-be boss-- who, upon seeing what you've done feels threatened. A CTO might not feel good about hiring an ex-CTO as a rank-and-file engineer. The second scenario is that of a business owner who, upon learning about your entrepreneurial experience is concerned about hiring someone who might come in, learn the business and potentially become a competitor. Yes, there's also the concern about someone pulling anchor early to go off on their own in an unrelated direction. It costs a lot of money to bring someone onboard. My conclusion at the time was that in this fashion entrepreneurship can be a curse. It can be nearly impossible to land a "regular" job because of it. In my case, after much frustration I decided that my only path was to run my own show again and off I went.