Sean “Diddy” Combs’ early career was characterized by an extreme desire to make it in the music industry. He identified Uptown Records, Andre Harrell’s company, as the place to be and reportedly did whatever he could to get his foot in the door. Those who knew him said this included sleeping outside Harrell’s car.

Sean ‘Diddy’ Combs did everything he could to surround himself with the right people

When Combs was young, he began working to get a job at Uptown Records.

“It was a boutique version of Motown, but we just had the hip-hop flavor to it,” Al B. Sure! said in the Peacock documentary Diddy: The Making of a Bad Boy (per The Hollywood Reporter).

His friends recalled his desperate drive to get an in at the company. He reportedly placed himself in front of the higher-ups at the company in order to get their attention. 

“Sean wanted to work at Uptown. He actually did some more suffering just to get that internship,” Combs’ childhood friend Tim Patterson said. “So, Sean would show up in the weirdest places: at Heavy D’s doorstep. He’d show up at Uptown, he’d show up at parties — anything to get the attention of the bigwigs.”

Another friend recalled Combs going to particular extremes to capture Harrell’s attention.

“From what I heard, he even slept outside of [Harrell’s] car because he really wanted to be in this,” Combs’ friend Rich Parker said. 

Sean ‘Diddy’ Combs didn’t always attract positive attention

Combs moved through the ranks quickly at Uptown when he gained a position there. This didn’t go over well with his co-workers. They reportedly began referring to him as “Satan” and flipped him off as he walked past their offices. 

“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.”

He admitted he wasn’t necessarily easy to work with.

“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.”  

His employees say he abused power when he got it

According to employees at Bad Boy Records, Combs’ company, he didn’t learn much from his experience at Uptown.

“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.”

People were constantly on edge around him, and this time he held more power.

“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.”