Almost every millionaire I know is married with kids and living in the suburbs. Unless you win the lottery or are a professional skateboarder, becoming rich is more like boring suburban reality than being an international flaneur. (Interestingly, the rich pro skaters I know all live in the suburbs with their kids, too)
As someone who has also floated around a lot, even through Japan, it's an interesting lifestyle but sort of the opposite of how to get rich.
I don't think he's talking about being rich, although he does reference money a lot. I interpreted the money references as a simple way to keep score (and one deeply ingrained in many cultures).
I think he's talking about the modern entrepreneur. Specifically, the people who are creating new markets, or are disrupting old markets. In order to do that, you need to be different than other people. I think he's saying that separates him from others because the drive for being fundamentally different (not the "color your hair" type, but the "visionary entrepreneur") is at odds with the human need for commiseration or comparability.
As someone who has also floated around a lot, even through Japan, it's an interesting lifestyle but sort of the opposite of how to get rich.