What I got from the article is that there's levels of rich, and always someone richer. Also, that a lot of stuff he felt in hindsight he should have paid attention to he dismissed as normal at the time because weird is normal in those circles, and stuff gets weirder as you get into richer circles, at least certain types of them. In other words, he didn't see it as risky business because risky means weird, and it's always weird business.