The only reason he might not be afraid of prison is because he never believed he would be sent there. We are talking about a guy who, with his *extremely* close relationship with Stuart Fraser, had spent the preceding years dreaming himself to be a Gates/Musk/Jobs/Satoshi future-tech visionary and had conned Fraser into throwing money at his shitty business schemes.

He is a narcissistic nobody who was fortunate enough to gain a personal connection to a very wealthy man who believed the crap he was spouting about how clever his ideas were.

Once the expensive cars and private jets started coming into the mix he probably started to believe his own bullshit. Sure, when the alphabet agencies have him against the wall, he'll just give 'em that dumb-fuck squinty-eyed grin and say sorry for making some bad business decisions and losing the muggles a great deal of money. They'll shrug their shoulders and be all, "Awww, hey, that's ok Joshie, this is the land of the free, home of the brave, you just be living the 'Mercan Dream, son!" and then send him on his way, right? Right? RIGHT? I mean, he's a good religious boy who loves himself some Jesus and fears himself some God, the 'right' god, of course, so nobody is going to be sending him to prison just for being an honest entrepreneur.

Cocaine's a hell of a drug.