I'd add that the industry really does not celebrate nor embrace failure the way that we're told it does. For those of us without the cushion of prior success or financial runway, repeating attempts to "get back on the horse" is an embarrassing exercise in futility.
With a failed enterprise, you lower your value in the eyes of many gatekeepers and peers, especially those who never tried running their own business.
But after repeatedly attempting to jumpstart businesses without capital, and subsequent failures, eventually you are more or less cast as foolish.
And god forbid you start to become pragmatic or slightly cynical in the world of tech startups! Because the moment your idealistic optimism comes into question, your "cultural fit" is permanently deemed negative. And bonus catch-22, having led startups also puts "cultural fit" into question for big cos as well.
Basically the personality changes that result from repeated business failure can begin to taint and poison your business relationships, and that can follow you around forever like a little dark cloud you just can't shake.
Psychological stamina is something nobody tells you about needing as a prerequisite for being an entrepreneur, but most of us don't learn that lesson until it's far too late...