For what it's worth, during the years I actually had these conversations, I doubt I ever made as much as a Customs clerk. I'd bring in maybe $20k in consulting and product income over the course of a year, which was enough to travel on but likely not enough to pay for, say, the apartment that the clerk lived in.

There's no requirement for privilege, or even "living wage" to lead such a lifestyle. As such, I appreciate that you thought I was somehow successful, but by most objective standards, I was just a homeless guy.