Both has something to lose.
But the advantage of the rich is that they've got more resources but still if they're losing, they lose money as well and they're just more capable of losing more than the poor ones.
It's still painful to lose money and I think that the rich folks also contemplate that moment and when they do, they just choose not to stick to that feeling for so long if it's not going to lose their entire riches.
It's easier for them to let go, you are right

Because they know that they still have something left but the pain is there.
We can see the perfect example through Drake. He's rich and yet he's losing a lot of money from his bet. He can easier go back whenever he's been left by his losses.
But for sure there's a feeling like pain of losing it but it doesn't stay for so long.