After Cher, rapper T-Pain is probably the person most responsible for Auto-Tune becoming a thing (and let’s face it, anything of cultural importance comes after Cher). And for a while there, his innovations in the arts of vocal distortion paid him handsomely. At one point T-Pain amassed a $40 million fortune. And then he lost it all. Well, he didn’t technically lose it, he spent it all on stupid shit like a $400K Big Ass Chain and a shit-ton of bad real estate investments in South Florida. At one point T-Pain was so broke he had to borrow money to get his kids some Burger King. Appearing on The Breakfast Club, T-Pain explained how he lost it all, but found himself. Say it louder Pain so Drake can hear you over the tick tock of his sex watch!
For T-Pain, the beginning of the end started when he bought a $1.2 million Bugatti which he “broke” about 5 months later. He put a hole in the radiator driving it too fast and his accountant had to tell him he couldn’t afford to get it fixed. So he sold it back to the dealer for $800K. According to Complex:
“That’s when I was running out of money,” T-Pain recalled, noting that—at the time—he had himself under the impression that a hands-off approach to his accounts was the way to go.
“Just started going crazy with the money,” he said. “I wasn’t paying attention to it. I thought if I didn’t have access to my own accounts I wouldn’t have to look at it, so it was bad business choices.” Elaborating further when Charlamagne tha God asked if he was ever truly “zero dollars broke,” T-Pain confirmed he was.
“I had to borrow money to get my kids Burger King,” he said, estimating that the most he ever had in his account at one time prior to that temporary setback was $40 million.
Pain also says that he let his manager buy up real estate for him as investments. And it sounds like his manager was chasing Nicolas Cage in the quest for the Holy Grail.
“Yeah, yeah, It was a lot of bad investments, a lot of things . . . Real estate. I was letting my manager do it and he was way more optimistic than I was,” he said. “He would just buy complete dumps and think that we can just paint and then we should be fine. Never sold anything that we bought.”
Pain says they were all worthless flop houses around where his manager lived. I mean, a South Florida flop house is as likely a place for the Grail as Rhode Island. And Pain also has his own version of Nic’s dinosaur skull; a gold and diamond chain “worth” nearly half a million dollars.
Pain says he had that shit melted down for the cash and then had a replica made that he’s going to hang in his house. So T-Pain learned about money in the most T-painful way. But losing it all also made him realize that his family is the most important thing in his life and he’s no longer trying to get rich. And he’s since fired all his staff, including all the “country cousins from Alabama” who “didn’t know how to do anything”.
Here’s T-Pain talking about his finances starting at about the 31:00 mark.