>but it's really difficult to bootstrap when you don't have the means.

You have to aim a couple rungs up, not all the way up.

Starting from literally zero you can probably retire modestly but comfortably the owner of a respectable tax dodging container storage and dumpster rental business assuming a little luck and work in your formative years (maybe the local street gang will install the love of hustling for a buck into you) to set you down the right path.

Going from zero to C-suite manager type, not so tractable.