I don't think Phil understands that the way he speaks seems condescending to most people, and beyond that it turns a simple statement into an incorrect one because he doesn't know what the words he says actually mean.
"Paypal is an ahnline currency system" lol wut?
Phil refuses to understand that his problems could be fixed by internalizing one phrase. "I'm not as smart as I think I am." That goes for money management, business management, marketing and anything law related. That's why he isn't losing his shit like most of us would be if we were in his shoes. He thinks he got over, because ignorance is bliss.