> there's a difference between taking a calculated risk, and being reckless -- and reckless people more often than not believe they were taking a calculated risk. This is especially true of people with gambler personality.

Just quoting this because it deserves to be read twice.

You're not wrong -- I just wanted to delineate between 'failure' and 'bankruptcy'. Clearly, if Bill Gates wanted to start a new company, the likelihood that it would bankrupt him is indeed minuscule, though not impossible. I would wager though, that unless it was exceedingly ambitious (e.g., very high risk), the possibility of him going bankrupt from any new venture is infinitesimal.

It's also perhaps worth noting that yeah, I'm also not making any value judgements on the OP, except to say that sometimes, even calculated risks are subject to sheer and utter failure, and that even playing things extremely safe, unless one has piles and piles of money, could easily lead to bankruptcy-worthy situations.