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Making the Label: My internship with Sean ‘Diddy’ Combs, Part I

April 21, 2011

Terrell Taylor, CEO of Positive Entertainment

Terrell Taylor, CEO of Positive Entertainment

By Alex Braun

Yesterday, I had a conversation with Terrell Taylor (@ttaylor1220), CEO of Chicago music event organizer Positive Entertainment, who also interned in the A&R department for the legendary Sean “Diddy” Combs’s Bad Boy Records in New York City.

I was pretty excited to hear how Diddy runs his businesses, but when I put down the phone, I realized there was may more to Terrell’s experiences than could be told in one blog post. So over the next couple weeks, I’ll be releasing his story in three parts.

First impressions

You could say music has shaped the lives of the Taylor family. Terrell’s name is getting pretty well-spoken in Chicago’s live music scene, but the family’s first brush with stardom — and Diddy — came years ago. After a decade singing in the South Side band Kwiet Storm, Terrell’s older brother Will found his big break when he went solo in the summer of 2007. That August, he passed auditions for MTV’s Making the Band 4, where Diddy handpicked him to be a vocalist in the R&B supergroup Day26.

“Diddy must have seen somebody more important, because he didn’t really look at me.”

Terrell was in a hallway at MTV Studios New York to support his brother on the show’s first-season finale when he spotted the hip-hip mogul for the first time. “I was walking toward him,” Terrell said, “so I went to shake his hand. Diddy must have seen somebody more important, because he didn’t really look at me … he gave me a quick handshake, but he kinda shoved me against the wall and kept walking.”

“I kinda hated him after that,” Terrell said — at least for a little while. But he wasn’t through with him.

As untouchable as Combs might seem now (Forbes recently estimated his net worth at over $475 million), the man who made legends of Mary J. Blige, Notorious B.I.G. and Lil’ Kim started out as an ambitious kid from the projects with an unparalleled work ethic — traveling constantly between marketing classes at Howard University in Washington, D.C. and an NYC internship at Uptown Records. Terrell knew Diddy was someone to model his career ambitions off of, and if he was going to start somewhere, he could do worse than learning from hip-hop’s most successful producer.

Months later in Chicago, Taylor found another “in” at a Keyshia Cole/The-Dream concert when he struck up conversation with a young woman in the crowd. “We just started talking … she said she was in New York doing a music internship for Bad Boy, even though the music industry stuff wasn’t really her thing.”

Sean "Diddy Dirty Money" Combs

Sean "Diddy" Combs

But music was — and is — Terrell Taylor’s thing. The woman gave him a contact number in Bad Boy’s A&R department, and for two weeks, he called and sent emails relentlessly. Nothing.

And then, a week after all but giving up, Terrell got a call.

The Empire State

On the other end of the line was a Bad Boy publishing and A&R assistant named Kevin, calling to say he was impressed by Terrell’s resume. (As a music management major at Columbia College, Terrell had already started organizing increasingly successful Positive Entertainment events with artists from Chicago’s hip-hop and R&B underground.)

Kevin offered to hire him as an unpaid intern if he could get to Manhattan … in two weeks. That was a pretty crazy order, but there was no way Terrell was turning it down. In a matter of days — after borrowing enough money from supportive friends and family — he was on the ground in the Big Apple, looking at apartments with his reality-star brother.

To Be Continued …

In Part II, we get into the thick of Terrell’s experiences at Bad Boy, including a ground-up view of at Diddy’s brand empire, Terrell’s chance to move up to a paid position and more encounters with the man they called Puff. Stay tuned.

{ 2 comments… read them below or add one }

anita mike( i need a mike) December 7, 2012 at 10:15 am

Iam a song writer I have songs with artist in mind iwill pay my own way to you. Ian confident in my songs.diddy I need a chance its my life.I take care of the elderly. But my true passion is music


anita mike( i need a mike) December 7, 2012 at 10:21 am

Ima email everyday if I have to


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