>On our last team Vegas trip I kept track of how much everyone was gambling as a proxy for their risk appetite

Yikes. Gambling is just a dumb idea in general (it is literally designed to make you lose money)... unless you are gambling with other's money. ;)

There is a diff between "With enough work, this risky thing could work out" and "With enough luck, this risky thing could work out if I stop while I am ahead"