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 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.
To me you're a millionaire when you have one million of assets excluding your residence.
That's a lot of money but that's not quite the same as having forty millions.
Reaching the one-million bar requires a lot of hard work, reaching the forty-millions bar requires a lot of hard work and sacrifices.
If your friends still have a regular job they're most likely at the first bar only.