Really interesting post. My suggestion: Hacking the stock market with AI's, algos, and current results from neural-science research, and large, accurate historical datasets and analytic models. There are lots of regs that mandate "prudent man" behaviour for agents and brokers, and myriad regs around capital required to execute or margin trades - but the domain of research-gathering prior to trade execution - is essentially wide open for "outsiders". Company officers face restrictions on when they can buy or sell company stock - but non-insiders have wide latitude, and in most cases are free to make buy/sell decisions whenever, and at any rate they wish to pay for. You are free to invest and speculate - and lose - your own money. And the neural-science on this is interesting. Most wealthy speculators in commodity markets, mostly lose. Most gamblers at casinos mostly lose. If you have wealth, you are able to give it away (or piss it away), without restriction, unless your family members can get you declared "mentally not competent". Also, environments where very complex regulations exist, allow and encourage "regulatory arbitrage" - structures can be created which take advantage of various regime differences. But the fact remains, few regulations exist which can effectively prevent someone giving away, or destroying their own wealth. (I recall a fellow in Sweden, who was ordered by a divorce court to turn over half his wealth to a former wife. He withdrew over $100,000 in life savings in cash, and carefully burned it all.) People face few restrictions in disposing of wealth. Charities exploit this fact relentlessly. Also, there are few restrictions on attending school, or gaining education - except in truly horrible societies, such as religiously deluded cultures, which for example, prevent women from gaining education to maintain breeding stock. But civilized societies encourage education, and often subsidize it. The existence of unlocked libraries (in ancient times, they were almost always locked), and our western-cultural concept of freely available science information, remains the greatest unregulated open space. It is also where the greatest opportunity resides. Western culture is unique, in that it "deregulated" knowledge acquisition, and scientific inquiry in the early 1600's. And there remains a risk of "re-regulation" of science inquiry. Imagine a world run by book-burning god-believers. You don't have to imagine. You can study the historical examples. Quite possible that science knowledge may be restricted and access regulated in the future. But for now, gaining knowledge, using that knowledge to get rich, and then giving away the wealth accumulated, remains an essentially unregulated activity.