It’s pretty hard to feel bad for billionaires, but according to a host of incredibly wealthy people there’s one aspect of being filthy rich that is no fun at all: deciding what to do when friends and family ask you for money. 

How do those who can afford almost anything choose how to respond when someone they love comes looking for cash? Is there a way to balance a desire to help with a need to keep financial ties from spoiling your relationships? Shark Tank investor Kevin O’Leary recently talked about how billionaires think through these requests on a podcast. 

His words offer a peek into the hidden world of the super rich. But according to financial planners, they suggest a framework regular people can use to think through how and when to offer financial help to loved ones too. 

Before we get into O’Leary’s comments, let me take a moment to try to convince you that the ability to cut a huge check to loved ones is actually a problem. Having nearly limitless resources has tremendous upsides, but several very wealthy people have spoken publicly about how being a potential piggy bank to everyone you meet can spoil relationships.

Bill Gates, for instance, told The New York Times how relieved he was that his daughter didn’t ask him for money when she was fundraising for her (now scandal-plagued) e-commerce startup. 

“I would have kept her on a short leash and be doing business reviews, which I would have found tricky, and I probably would have been overly nice but wondered if it was the right thing to do.

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