to piggyback that John Mulaney bit

he's kind of a rogue rich guy and there's an almost outlaw appeal to a certain type of american to the in your face anti-intellectual guy doing things his own way. They don't believe they're being scammed because they think he's one of them, especially once he dove more into the fed up white man thing.
Same people who can't stand those darn flashy rappers in front of their planes and bentleys are all good with the NYer who shits in a gold toilet.