With the same set of actions & work, pointing in a different direction, he could have done quite well for himself working on another idea.
I'm guessing his biggest downfall really was in having an aversion to working with others. He could work with others at a startup and make some great stuff & quite possibly do well. Instead, he chose a more sure fire approach to making money on his own -- with the morality and legality of what he was doing as the cost.