“Working for Sean ‘Diddy’ Combs was the job of jobs,” said Karleen Roy, founder and CEO of The Vanity Group, a full-service boutique lifestyle management agency. “He was the best boss a person could ask for!”
The St. Louis native (by way of Memphis) and Howard University alum worked by his side as an executive assistant and offered a take on his personality that is a far cry from the egomaniac many would assume based on his classic appearances on the “Making of the Band” franchise on MTV.
“There would be times where I would screw up something minor, but the key to my success was being able to communicate on the same level as he did,” Roy said. “It was like we were in a marriage. I knew what he was thinking before he did, and that’s why I was employed for so long.”
Landing a gig with Combs, a master at branding and rebranding, was essential to achieving her goal of being her own boss in the entertainment industry. But her career began as personal assistant to a then-unknown singer who would eventually take the industry by storm as Ne-Yo.
She teamed up with Ne-Yo, who at the time was going by another name, after she stepped out on faith and moved to the Big Apple.
“Working with Ne-Yo during the early stages allowed me to get a feel of catering to an A-list clientele,” Roy said.
She also says being a personal assistant is more challenging than what people see on TV. She credits her early successes to being able to anticipate her boss’s next move and being savvy enough to make it happen under any circumstances.
Roy worked at Sony Records under their Legacy label and stayed on the grind even when she became discouraged by not landing her dream job.
“I questioned my passion for wanting to be in the entertainment industry,” Roy said. “I thought maybe I’ll work in PR or move back home and get a normal job.”
But she stayed the course and kept her industry connections intact, which Roy says is a must if one plans to make a name for themselves among the many hopefuls looking to break into the field.
By being consistent with her contact list, she landed the interview of a lifetime and would ultimately work side by side with Mr. Bad Boy himself.
But these days instead of working to facilitate the vision of someone else’s brand, she is using The Vanity Group to build one of her own.
Her day-to-day work consists of responsibilities such as making sure when Trey Songz wants to vacation in the south of France that he has a premier yacht, fully stocked with the finest of fine, or chartering a private jet to plan a holiday party for Fergie.
She credits her famous former boss with laying the foundation for her success.
“Working for Puff made me become a better businesswoman,” Roy said. “I continually strive for the best!”
As she reflected on her experience in the entertainment industry, Roy was eager to offer suggestions for those looking to make a name for themselves that are transferable to just about any field.
- Become an intern in the area you hope to go into. This will be your stepping stone if you play your cards right.
- Maintain great relationships with people you meet in the business and stay in touch with them.
- Get a mentor in the business that you respect.
- Always remain kind, respectable and gracious – your personal brand is all you have.
- Don’t give up and have some tenacity … only the strong survive!
Follow Karleen Roy on Twitter @VanityGroupNYC or visit thevanitygroup.com for more information.
