I think the education, Jane St, etc... is what allowed him to be naive. He never had to do the grunt work of running ops at Goldman Sachs to earn his stripes.

I think the education, Jane St, etc... is what allowed him to be naive. He never had to do the grunt work of running ops at Goldman Sachs to earn his stripes. He just skipped to the fun part of mansions and TED talks. Anyway, it's clearly fraud and he should go to prison. And in some ways maybe the callous disregard for bureaucracy and controls (we don't need these, it's a waste) is worse than if he had malicious intent (I'm going to take all this money and run). For the person with malicious intent, there's not much to do other than build rules to constrain future people like that since they won't learn from the punishment of others. For the person with disdain for mechanistic controls and regulation however, we do need to show that it's just not acceptable to bypass that stuff and that society will punish you severely.