I wouldn't be surprised if this guy had a tough time dealing with people and couldn't stand working for anyone or managing employees. I think if he was born 20 years later he would have gambled all his money away on day trading schemes.
There are a lot of losers out there -- isolated, paranoid and looking for their loophole in the system. They'd be just fine if they'd realize that getting some social skills and learning to work well with others would fix most of their problems with the world.