to be overflowing with money
The Spanish phrase 'andar sobrado de dinero' is colloquially used to indicate that someone is well-off financially or has a lot of money. It is often used to describe someone who is not only affluent, but also conspicuously displays their wealth.
Juan is always rolling in money.
This means that Juan always has lots of money.
You shouldn't be rolling in money and then have nothing to eat.
This implies that you should not flaunt extravagant wealth while neglecting basic needs like food.
If one can be rolling in money, one can handle any situation.
This indicates that having a lot of money can empower one to tackle any situation.