I’ve thought about this too. Like the stories about fairly normal people that hit it big in the lottery and then are destitute and living on the streets in less than two years. It’s tragic but it’s their money that they made horrible decisions with. But to do this with other peoples’ money just blows my mind. Bernie Madoff did it in the most coldly calculating way. But this guy and the WeWork couple spent other peoples’ money like it was normal to buy jets and mansions instead of paying the electric bill.

My girlfriend and I take turns buying each lottery tickets. It’s our inside joke that we want to see how the other would handle a big windfall.