Diddy Reflects on Being a Self-Made Billionaire: “You Work Hard and You Get What You Deserve”

Sean “Diddy” Combs has achieved many things over the years. He claims titles like rapper, R&B artist, mogul, and man more. Recently, he discussed his billionaire status.

Last night, Combs appeared on Jimmy Kimmel Live to talk about his new album, receiving the key to the city from New York Mayor Eric Adams, and more. During the conversation, Kimmel asked, “Is it great to be a billionaire? Do you ever think about it at night?”

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“I think about it every day,” Combs replied, laughing. Then, he got a little more serious. “Look, you have to understand me, I’m self-made,” he said. “I came from just putting two quarters together, putting two dollars together.” He went on to reveal that he has been in grind mode since he was a kid.

At 12, Diddy said he was a paperboy. To clarify, he said he wasn’t actually allowed to be a paperboy. Instead, he ran a “paperboy scam.” He would deliver papers for the kids who had legitimate positions and split the money with them. That was hardly the only work he put in as a youth, though. He added that he also cleaned bathrooms in New York during heatwaves and painted houses.

“You work hard and you get what you deserve,” Combs said. “I’m blessed to have had people who support me.”

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Then, Kimmel wanted to know who from his childhood would be the most surprised to see how successful he is today. “I would say my first girlfriend,” he said after a moment of thought. Then, he added, “She messed with my best friend and broke my heart.” Kimmel asked what his best friend was doing today. Combs said, “I don’t know what either one of them is doing today. They’re not doing this.”

Shifting the conversation to his creative process, Kimmel wanted to know if Diddy had ever written a song about his ex or worked her into his lyrics. Combs said that he works all of his “heart issues” into his songs. “I take pride in being vulnerable about my love life. That’s why I made an album called The Love Album.”

(Photo by Dimitrios Kambouris/Getty Images)