The thing with not being bothered by losing (huge amounts) is, that it will also make you lazy and not being focused. You just want to have fun and don't work on improving your game. Being pressured and alert is necessary to keep your concentration up. So, if you don't bother, you are likely to make bad decisions
Fully support this reasoning
And it goes far beyond just poker or gambling in general. Such an attitude, in its generalized form, is applicable to how we live our lives, altogether. To be more specific, you can be very well off overall like having a handsome stash of bitcoins (let's talk cryptocurrency here as it seems appropriate), but you may still be somewhat short of cash money, and that will keep you extremely focused and alert on looking out for earning opportunities even if you could just spend your bitcoins and fill your boots to your liking (though that would make you lazy and idle)