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When he was in his early 20s, Sean “Diddy” Combs began working at Uptown Records. He looked to label founder Andre Harrell as a mentor and he quickly rose through the ranks at Uptown. Despite his success, he lost his position at the label in 2003, at least in part because he began to annoy other employees. While he later characterized the end of his tenure at Uptown as a power struggle between himself and Harrell, he once admitted that his behavior had landed him in hot water.

Diddy admitted he didn’t have many friends at Uptown Records

Diddy started at Uptown as an intern, but he rapidly moved up the ranks at the company. He played a key role in the success of Mary J. Blige’s debut album What’s the 411?

Despite his wunderkind status and closeness to Harrell, however, Diddy was reportedly not well-liked amongst Uptown employees. They allegedly flipped him off as he walked past their offices and began referring to him as “Satan.” Diddy acknowledged that his bad behavior at Uptown hadn’t won him many friends.

Sean 'Diddy' Combs photographed in a recording studio
Sean ‘Diddy’ Combs | Andrew Savulich/NY Daily News Archive via Getty Images

“At first I was shy. Then one day I realized that shy s*** ain’t going to get me nowhere in this life right here, in this world,” he told Rolling Stone in 1997. “Sometimes people say I’m cocky and arrogant, but that comes with it.”

In 2003, Harrell fired him for “irritating people,” leaving Diddy feeling lost and unsure of himself. 

“I cried for a couple days and felt like I wanted to jump off a building,” he said in 1995, per Rolling Stone. “I think at times I was hard to work with.… Possibly I was doin’ s*** that an a**hole would do, just abusing the power. But that was only a little bit of the time.”  

He later characterized his exit as a power struggle

Later, Diddy said his ambition got in the way of his working relationship with Harrell. He said he wanted an equal share of power at Uptown Records.

“At first, Andre was just there for me with everything,” Diddy said. “He put his faith in me, and we had a great time. What started to happen is, I started to have other dreams. At the same time, Uptown was growing and getting bigger, and Andre was having to deal with corporate concerns. I couldn’t understand that from the creative side, so I started getting on his nerves and bugging out and being real rebellious. It became a situation where it was two kings in one castle, and it was his castle, so I found myself in the moat.”

He admitted he felt scared at first, but eventually went on to found Bad Boy Records.

Employees say Diddy acted like he did at Uptown at Bad Boy Records

Though Bad Boy was his own company, Diddy continued to create problems. He was a volatile presence in the office, and he demanded as much attention as his artists.

“I distinctly remember the day that Clive Davis called and asked me to start garnering press for Puffy just as if he were the artist,” Bad Boy employee LaJoyce Brookshire said. “Behind his back, I used to call him my problem child, the Notorious V.I.P.”

Sean Diddy Combs wearing sunglasses and a black leather jacket
Sean ‘Diddy’ Combs | Shareif Ziyadat/Getty Images for Sean “Diddy” Combs
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Other employees were reportedly afraid to stand up to Diddy, lest they become the target of his temper.

“He was so volatile,” a source who worked with Bad Boy said. “He’s always on the edge of snapping and being scary. People did whatever he said to stay in his good graces … and Puffy exploited people’s desires to be in those environments.”