I remember how the banks used bailout money to pay out bonuses. There was an uproar about it, and they scaled it back, but I remember the banks arguing that if they were going to survive these turbulent times, they'd need to keep the top talent, and that meant bonuses. There was that indignant letter to the nytimes from an AIG employee (salary + bonus around 700K) who was angry that people were angry about his bonus, since he had "nothing to do" with the people who ruined the company (his analogy was that it was like blaming the plumber when the electrician burns the house down).
I worked for a startup that tanked. Lots of people put a lot of their lives into it. Options were worthless (and I knew people who had worked for 7 years or more) The startup kind of made the last payroll. We got our regular paychecks, but they failed to pay out all of the vacation time. We found new jobs, and moved on with our lives.
Nice thing about high tech culture is that the experience (even the failure) made more more employable, not less. So in that sense, you can fail in the valley.
It depends, only a small number of PhD's get paid a lot of money in Finance. They work primarily for quant funds if they make a lot and more than likely work for risk management which pays much less.
Risk aversion is certainly one factor, but another is that Wall St. (and local equivalents) offer some genuinely interesting and hard problems to play with and are generally pretty good about letting their smart people have pretty free reign to play with those problems.
I know among my mathematician friends finance has been a popular career avenue, not because of the money, but because finance was the only industry they felt genuinely respected mathematicians and was willing to hire mathematicians to work on mathematics.