Back when, he was your typical shy geek. He liked girls, a lot. But didn't have the confidence, nor the "signalling", and they didn't like him.
He went to work in Silicon Valley just before the dot.com boom. And he hit the options lottery in a successful startup. He hit it out of the park, so to speak. Fully post-economic. Probably 8 digits post-economic.
Suddenly, when before he couldn't get a girl to look at him without sneering, now girls, often the same girls, were coming out of the woodwork to be with him. And it wasn't because he was any better looking, either.
Fortunately for him, he saw what was happening, and didn't get caught by a gold digger. He left Silicon Valley, moved to a flyover state, bought a nice snug little condo, starting going by his middle name, and tells people that he "consults". He tells nobody there how well off he is.