It is true, when you have a safety net, it is easier to recover after failing (multiple times). On the other hand, I wonder how many of the billionaires, enter a wealth-protection mode after they made their wealth, rather than taking on more risks. I'd say their risks are in many cases at least partially covered somehow, either because they use other people's money, or because they use non-public information that give them a leverage or because they go into 99.99% no-lose deals.