T-Pain says these are the 2 rules billionaires taught him for sharing money with friends and family

• T-Pain issues an ultimatum when friends and family ask him for money.
• He said they can either work for him to earn the money or take a one-time payment.
• Billionaires like Kevin O'Leary have similar strategies.

T-Pain has no qualms about issuing an ultimatum when it comes to his money.

The "Buy U a Drank" rapper shared how he sets boundaries with friends and family asking for money during a Twitch livestream on August 29. He then shared a clip of the footage on his Nappy Boy Gaming social accounts last week.

"There are two things I do, and I learned them from literal billionaires," T-Pain said.

He said people can either work for him to earn money or receive a one-time payment on the condition that they never ask for another.

T-Pain said he didn't initially have that rule, but adopted it after realizing that his decision to gift money to friends and family wasn't always reciprocated.

"If you want to not be an asshole to everybody, make it their choice," T-Pain said. "That's really what's happening."

Setting financial boundaries with loved ones is a tricky task that folks at all levels, including billionaires, struggle with. In 2025, "Shark Tank" investor Kevin O'Leary said during an interview on "The Fifth Column" podcast that the worst part about being rich is family members asking for money.

"In the beginning, you will feel the guilt of success, and you will give them money, and you will slowly destroy your relationship with those people," O'Leary said. "You'll have horrible Thanksgivings."

O'Leary said he gives people the money they requested only if they agree to never ask him again.

"I don't want to be paid back. I don't want to talk about money. I want to have Thanksgiving dinner and talk about family. Not money," he said at the time.