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.
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Lauren Edmonds is an award-winning reporter on the Business News team. When news isn't breaking, she covers personal finance, kitchen-table economics, and paths to financial freedom, including investing, real estate, side hustles, and small business. She also writes about guaranteed and universal basic income programs in the United States.Lauren has also covered lifestyle and entertainment, digital culture, and more. She has a master's degree from the Columbia University Graduate School of Journalism and resides in New York City.Do you have an interesting story to tell? You can reach Lauren at [email protected] or on Signal at ledmonds0.07.Popular StoriesNetflix wants to be Disney when it grows up Why Hollywood is paying this 17-year-old up to $20,000 to boost film trailers with TikTok editsHere's all the free money Trump's talked about giving Americans during his second term — and where it all standsA 17-year-old earned $72,000 after investing his e-commerce profits into stocks. Here's why he bet on the tech industry.Lawmakers float a nationwide basic income experiment that would cover the cost of a 2-bedroom apartmentNearly 30,000 Americans have received about $335 million in basic income. Here are 5 takeaways. Americans ditch suffocating healthcare costs and divisive politics to retire in Italy: 'It's the way they approach life'From 'road-schooling' to gas that costs $500, this family of 4 shares what it's like living in a solar-powered Greyhound bus
