It's not just the amount, it's the action, particularly when in context of some of the other waste. Gambling away the same amount of money that people get for

It's not just the amount, it's the action, particularly when in context of some of the other waste. Gambling away the same amount of money that people get for doing a YC round is not the right sort of thinking for long-term success. It's also the pervasive attitude of using money as a means to impress others. No amount of money will fix that, because there's always someone richer to impress. You mightn't think wasting 30k in vegas was fun, but I'd ask if he would do the same thing in a less 'glamorous' place. Frankly I would see the cars as less of a waste because presumably they still have some resale value. edit : I'll just add to that, think of any mentor you can. Now ask yourself : would that mentor suggest blowing that cash on gambling, strippers and expensive gifts for an (obviously) fair-weather girlfriend was a good idea?