The second job thing is interesting, it's like he doesn't understand that the economic situation of a society as a whole (generally a country) dictates what % of people can afford to have nice things.

As a result of that, if your society is in a bad economic situation it may very well be the case that even if everybody was working the same number of multiple jobs, advocating for themselves, and busting their butts, most of those people are still going to be in a shitty situation due to things entirely out of their control. Furthermore, the ones that got out of the shitty situation, even though they're doing all of the same things, only did it due to dumb luck / being in the right place at the right time.