What magnitude of money are we talking about? A large enough pile to relieve one of the necessity of ever again depending on work to pay the bills, or something less, say a few years' worth of living expenses?
How about a year's worth of expenses (post edited to reflect this).
In the open thread, moridinamael hypothesized that LWers would be willing to take more risks in order to become rich if they had a financial safety net. This seems like an idea worth exploring further.
What would you do if you had a financial safety net (maybe a year's worth of living expenses) to fall back on if your venture failed?