Let's be fair here
People said Musk was mad when he started Tesla also. Few would argue that SpaceX was an incredibly high-risk investment when he started it also, but it seems to have paid off.
As I understand it, from what I've read about Musk elsewhere, he is more interested in pushing the limits with these sorts of things than in actually making money. The fact that he IS making money on them, I think, is a bit of a surprise. If that is true (which, grain of salt, it may not be since that's just my impression from a few articles I've read) then the whole Hyperloop thing doesn't seem quite so mad. Even if it's not true he's already made a mint from two "mad" ideas so why not go for a third?