I have a horrible thought.
Most (legally acquired) debts are dischargeable in bankruptcy. That puts a floor on the amount of money one can lose. If your net worth is "almost nothing" and you can find suckers, er, I mean, organizations with loose standards that are willing to lend you money, then the expected utility of risky bets changes in a way that favors you - because going bankrupt while owing $10,000 isn't much different than going bankrupt while owing $500,000. Of course, going bankrupt is still pretty bad either way, but the upside of winning a risky, highly leveraged bet can also be correspondingly large...
Personally, I don't think this is a good idea and is probably unethical anyway, but it is the kind of crazy thing a certain kind of munchkin would do...
I knew someone who did this: bought large amounts of jewelry-making and other crafting supplies on credit, went bankrupt, and then made a living by using the supplies. It feels like theft to me.
Thus spake Eliezer:
It seems that many here might have outlandish ideas for ways of improving our lives. For instance, a recent post advocated installing really bright lights as a way to boost alertness and productivity. We should not adopt such hacks into our dogma until we're pretty sure they work; however, one way of knowing whether a crazy idea works is to try implementing it, and you may have more ideas than you're planning to implement.
So: please post all such lifehack ideas! Even if you haven't tried them, even if they seem unlikely to work. Post them separately, unless some other way would be more appropriate. If you've tried some idea and it hasn't worked, it would be useful to post that too.