My point does seem obvious after re-reading. What I really wanted to imply is that the current startup system basically penalizes experienced people. Is that a good thing? Is it even possible to change that?
This only applies if you have optimized your career around being an employee, though. Someone who makes $300K/year obviously has, and has picked up quite a few skills on being productive and navigating office politics. But a 50-year-old homeless bum who just got his life back together faces the same incentives as the 22-year-old startup founder - perhaps even moreso, because employers will look at a gap in work experience with suspicion.
And it seems like many of the businesses started by older founders fit this pattern - either they've just been fired and lost everything, or they're housewives returning to the workforce, or they're senior citizens looking for a career change. Once you've got nothing to lose, you've got everything to gain.
For young folks, there's little risk and opportunity cost but with zero experience likelihood of success is small.
For older folks, there's more risk and opportunity cost but with more experience and connections likelihood of success is greater.
This isn't a penal system, this is a distribution system. Being young isn't the prerequisite to success. Everyone harps and focuses on it because of that trait is unique (remember, likelihood is small) in an otherwise older folks dominated field (remember, likelihood is bigger).