He also did a media tour after things blew up instead of just shutting up, which from what I gathered isn't the best idea for staying out of jail. Real overconfidence in his charisma?

The fact that he did this instead of executing a planned escape and going to hangout with Ruja Ignatova is the main reason for me to think he believed his own shit.

Either he believed his own shit or he was certain that he was smarter than everyone else.

I suspect the latter. I suspect even worse -- that he believes not only in his own genius, but that everyone else is actively stupid.

Did media tours while out on bail.

Leaked his ex-gf's private diaries in an attempt to intimidate her.

Decided to testify at his own trial.

I'm almost certain that he thought he would give a grand speech and all the jurors would instantly take his side, just like he had experienced with VCs, journalists, employees and other sycophants for the past decade.

Hubris, thy name is psyche.