It feels kinda dumb!! There are a lot of things he could have done better!! If he can invest in options why would he invest in stocks!! He would get much better returns with options. There is way more risk in them but he already knows the future. Come-on. Instead he goes for auctions and even investing in Real estate!! Come-on, its too much work.
Maybe he might not know about the best way to earn money after time travelling, but he can think about that. He can ask smart people around him, but nah he is supposed to be the smartest of them even if he is dumb.
Going to Military for 2 years . Yeah, I am lost. The above points can be forgiven but this, Haha!!