The Cost of Entrenchment: Why CEOs Are Rarely Fired
knowledge.wharton.upenn.edu
knowledge.wharton.upenn.edu
Assuming that the board isn't certain of hiring the best candidate, lots of space at the top is going to make any individual companies' talent pool worse by ensuring that other companies snag some of the best available talent for their own vacancies.
This selection problem (and your argument about signalling) might partly explain why larger companies are more willing to fire and loss-making companies are apparently no more likely to fire than profitable ones - a loss-making small company is much less confident in their ability to hire an outstanding replacement than a profit-making larger company with a board perceived as trigger-happy.
How are you identifying "trustfunded hipsters" and how do you know that you're correct? Or, are you just assuming something about people whom you don't like that lets you feel good about yourself?
Data point - I don't have a trust fund and I'm too old to be a hipster. My parents are comfortable now but grew up below "dirt-poor".