We live in the same town and I happen to know people who rent from him and who work for his merch company (they successfully unionized recently). He owns at least 3 properties in a town where those houses sell for $500,000+. I don’t remember if he inherited those through family or not and those are the only residential properties he owns that I am aware of.

His union busting was with DFTBA (Don’t forget to be awesome). You won’t find any of this in the news or Wikipedia because it’s local stuff, low-profile, and he’s treated like he’s some saint by locals. I could drop the address of his house and the rentals he has on the same block.

My main point is that of course these are his takes on economics, he benefits from the system.