I dunno, I think he might have figured out how to bottle lightning because he had another show after The Room that was the same kind of "so bad it's good" as The Room was. He'd have to be pretty delusional to think he was making high art after the way The Room was received, so to realize what people liked about his art (assuming he didn't know that in the first place) and not immediately just churning out garbage instead tells me he does have talent. Entertainingly bad is a hard line to deliberately walk.

Plus there's no evidence he was born into money. Maybe a bunch fell out of a plane with him.