I'm inclined to split the difference. He had legitimate criticisms and for the most part his ultimate goals seem beneficial, but at the same time he's self-interested and seems happy to ensure he's the one making the buck in the process.
Maintaining the vacuum of the hyperloop would have used more energy than it would have saved from friction and reducing air friction would not have gained any noticeable speed over a well designed bullet train
Plus have you seen the weird top heavy transportation thing he suggested lately? It's entirely absurd
That's besides the fact that he makes wild claims about his car tech while they have numerous quality control issues and never live up to those claims.
He's just a profiteer and I don't know why anyone listens to him