To go bankrupt a person has to go deep into dept that they cannot repay. This
is generally something that can happen to rich people when they make
extravagant investments or when something goes wrong in their business. Thus,
it’s very hard for a bagger to end up bankrupt, but it’s not at all impossible
for a bankrupt businessman end up a beggar.

People who have a lot to lose have a lot of worries, but if you are poor you
might sleep better. The rich man contemplating financial disaster or about to
take a major risk might quote this out of bravado, but only to focus his mind
on the consequences of failure.