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

April 25, 2011

Sean John billboard, Times Square

Diddy's giant Times Square billboard can be seen from the entrance of his offices on Broadway. (Credit: Flickr user Been Around@Home)

By Alex Braun

Last week, we talked to Chicago-based live music promoter Terrell Taylor (@ttaylor1220), CEO of Positive Entertainment, about how he landed his internship with Bad Boy Records in New York City. In today’s Part II segment, we get into the heart of Terrell’s amazing internship opportunity and see what he learned along the way.

A 200-foot billboard of Sean “Diddy” Combs in black shades stares down Broadway from Times Square, watching every artist, employee or intern who enters the extravagant offices of Bad Boy Records. The label itself is a heavy icon of modern popular music, but that alone wasn’t what struck Terrell Taylor as he arrived at his first day of work. It was the sheer scope of Diddy’s business empire.

A mogul’s lair

Even before he was Puff Daddy, Sean Combs was a businessman — and that aspect of his persona continues to loom as large as his music. His other businesses are run out of the same building, one on top of the other. While the Bad Boy office where Terrell started his internship are on the fifth floor, other floors house enterprises like Sean John — Diddy’s clothing label, which is carried by major department stores around the world — and Ciroc — Diddy’s premium French vodka. Terrell said Diddy was based on the sixth floor, but he rarely stays in one place.

“When Diddy gets on the elevator, you can’t get on the elevator with him.”

When Diddy’s in town, Terrell said, he wanders everywhere in the building to survey operations, and puts in more long hours and late nights than any mega-millionaire he’s ever heard of. “[Diddy] works as if he don’t have a dollar in his pocket,” Terrell said. “He always kept that drive he had as an intern, and I think why he’s still on top.”

Apparently, he also likes his personal space. “When Diddy gets on the elevator, you can’t get on the elevator with him,” Terrell said. Security guards are notified when he’s about to board, and by keeping one eye on the CCTV cameras, their job is to prevent anyone from bothering him. But that’s easier said than done.

The second time Terrell Taylor met Sean Combs, security couldn’t intervene. He was already riding the elevator when the doors opened and Combs happened to board.

“I said ‘My name is Terrell Taylor,’ and I gave him my business card and shook his hand; told him I was working in A&R on the fifth floor,” Terrell said. This time went a little better — Terrell said Diddy seemed to halfway recognize him, and offered a few words of encouragement before he stepped out. “I was nervous,” Terrell admitted, “but I did what I had to do.”

Getting noticed

Networking was a huge deal at Bad Boy, Terrell said — and not just getting into the boss’s library of faces. “I got to know everyone … from the security guards to the people in the elevator,” Terrell told me.  “Because these people are always going to be around here, and if you get to know them, they’ll probably let you in if you need to get back in the building.”

The Sean John front desk

Sean John, Diddy's hugely successful clothing line, is housed in the same building as Bad Boy Records.

But Terrell also thinks he stood out as an intern by working hard and paying attention to details.

“Everything they were telling me, I was sucking it up like a sponge,” Terrell said. He quickly learned from Kevin, the assistant who had hired him, by reading contracts in the publishing department — everything from guest appearances to music samples to licensing Bad Boy artists’ songs for TV shows.

“If a TV show wanted to use It’s All About the Benjamins, I had to go through the catalog to see if it was even enough money for them to do it for those two weeks.”

Terrell had some background on the business from his classes at Columbia College, but he said he was shocked to see how much of the profits on hit songs were eaten up by royalties.

“Everything they were telling me, I was soaking it up like a sponge.”

“One of [Bad Boy’s] writers was a heavy writer for Rihanna and she did the verse to [rapper T.I.’s] Live Your Life. She wrote the hook for Rihanna and the song went platinum, and she got 10 percent on the song due to that fact — that’s a million copies, so about a million dollars.”

T.I. didn’t even get the most money out of the song,” Terrell said — nor did Rihanna or the song’s writer. “The sample [from The Ozone’s Dragostea Din Tei] goes right back to the ‘60s.” Since The Ozone doesn’t have a publishing deal anymore that would distribute their profits amongst representatives, band members could make more money off being sampled in a hit song than they did when they were releasing albums.

Terrell Taylor, CEO of Positive Entertainment

Terrell Taylor, CEO of Positive Entertainment

Moving on up

Weeks into his internship, Terrell was regularly seeing unfathomable exchanges of money — but still not making any. (Terrell said at the time he interned, he didn’t know any other Bad Boy interns who were paid.) The experience may have been invaluable, but personal finances are finite — and living in the heart of New York City was beginning to disintegrate Terrell’s wallet.

But strong work, persistent networking and a lucky stroke of fate were about to pay off.

To be continued …

In the third and final part of Terrell Taylor’s story, we’ll find out how he worked his way into a paid internship, hear about his third run-in with Diddy during recording sessions for Last Train to Paris, and learn what he took away from his once-in-a-lifetime experience.

{ 3 comments… read them below or add one }

Aijalon Wallace May 1, 2012 at 5:55 am

Hey Terrel, how can I get in touch with you and get your help to receive a internship.


Lauren Roach December 20, 2012 at 9:10 am

Hi Terrell I'm a recent graduate, ready to work hard, and I'm interested in an Internship. If possible may you please contact me with any information.

Thank You


juliet cato stewart February 26, 2013 at 11:37 pm

Hi Terrell-

I'm a Custom Designer Major at the Academy of the Arts in San Francisco. How can I get an Internship with P. Diddy's Fashion Line.




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