Aaron, I'm so glad I read this today!
It's not quite a "work for other businesses" strategy, but I made the decision to jump from running start-ups as a teenager into a full professional services career (audit) to gain behind the scenes insights into what made businesses work... or fail.
Ironically, that decision has left me challenged with a distinct stigma from the VC and start up world! Turns out I'm not one of the cool kids anymore? ;)