Continuing in our ‘Breaking Into’ Series, we decided to delve into the world of entertainment business and how you can have a successful career in it. Who better to sit down with and talk to than Karleen Roy, the founder of THE VANITY GROUP, a New York City-based boutique luxury lifestyle management company servicing A-list celebrities and powerhouse brands. Since 2013, Roy has been the trusted ‘make it happen’ woman behind many impossible-to-get restaurant reservations, lavish red carpet events, and last minute getaways on private jets, for celebrities like Common and Diddy.


As a creative, well-connected, and unapologetically black entrepreneur with impeccable style, Karleen’s been profiled time and time again for her work in the entertainment business. She started her career as “an eager publicity intern at Def Jam Records in the Artist Relations department,” noting that she was always excited to do everything an intern does–even grab coffee and order lunch for the executives. Despite it being an unpaid internship, the lessons she learned became applicable to her own business , including the sheer force of networking and how tables will turn when you are consistent.

Originally from Memphis with midwestern roots (she spent the early part of her childhood in St. Louis), Roy attended the Mecca, Howard University in Washington, D.C., where she majored in Sociology and minored in Public Relations. “I did not know I wanted to work in entertainment…that came maybe around my final year in college. But I did know I wanted an exciting career where I could use all the things I learned in my studies. I applied for many jobs and internships in every field I could after school and did not get a response nor hired for any of them! Def Jam was the only opportunity that panned out and it was the one I really wanted so…. LOOK AT GOD!!


After leaving Def Jam, Karleen went on to work as an assistant to Ne-Yo and his production company, Compound Entertainment. The experience taught Roy that studio life was not necessarily for her; effectively, she made a shift working over at Sony Music by day, and by night working events as a volunteer all over town for multiple entertainment companies who needed extra  help, among them, Violator Management. “Violator managed all the top music acts at that time,” she told us, ” Puff, Busta, Missy Elliott, 50, LL Cool J, Mariah Carey, and Q-Tip to name a few. That was a major career learning experience, I picked up so much there by just being a sponge and watching people like Chris Lightly who founded the company and the day-to- day managers who worked the artists projects.”Karleen-Roy-3

Her big ‘break’ came when she “landed a coveted role at Bad Boy as an assistant in the Chairman’s Office, Sean “Diddy” Combs. ” After always having dreamed of working for Combs, Roy literally jumped at the opportunity, saying she ” went to the nearest Kinkos to work on my resume and put a whole presentation together on why they should hire me for the job!” Starting off as the Assistant to Chief of Staff, she was then promoted to 2nd Executive Assistant to the Chairman, then first assistant and then finally promoted to Senior Executive Assistant to the Chairman. “My time at Bad Boy and working alongside Mr. Combs was priceless and I wouldn’t trade it for anything in the world. Mr. Combs is the hardest working man in show business and regarded as one of the biggest global figures of our time. To be his right hand and driving force of communication for him and the Executive Office is the best training there is for anyone interested in entertainment or anyone hoping to sharpen their skills in business.”


After working at Bad Boy for years, Roy had thought her next move would include artist management, talent relations role or support of another music executive. After resigning and taking time to figure out what exactly she wanted to do next, she began doing things to pay the bills to hold her over, including producing red carpet events, organizing various personal requests for celebrities, planning international trips for wealthy people she knew, helping a stranded artist get a jet from Point A to Point B.  She said, “It was at that time where I was like “Okay…this IS a business” – and that is pretty much how The Vanity Group was conceived. After doing my due diligence and consulting with the proper professionals, I was like “okay time to jump out the window and just make this thing real” …and the rest is history.”Karleen-Roy-The-Vanity-Group-Breaking-Into-Entertainment4

Aside from the daily administrative work of emails, follow ups, calls, and maybe a business dinner, Roy explained that events and project differentiate her average day. “Most of the time, our clients do not give us a heads up or much of a lead time for most of the projects we work on, so things can get completely crazy and non stop! Those are the moments I love, fast paced days that are no guts no glory!”

Karleen-Roy-The-Vanity-Group-Breaking-Into-Entertainment6What are some of those projects that her team have worked on? “We have done projects like Justin Beiber’s huge birthday party in 24 hours, Ne-Yo’s massive wedding where we were brought on to manage the event in less than 10 days, Puff’s New Year’s Eve party within 2 days, completing the interior design project for Rick Ross’s 109-room estate or surprising a singer with 10,000 pink roses to be delivered to their studio AFTER the flower market closes – those types projects for example we can not foresee so when we get the call we just shift gears to make it all happen!”Karleen-Roy

In order to keep up with a schedule that’s ever changing, one must possess a creative mind that’s constantly stimulated and inspired. “Living in New York has absolutely inspired my style over the years. I love the big black hats worn by the Jewish men in Brooklyn, I purchased a few of my own. I’m also obsessed with the traditional African garments worn by the African men in Harlem on 116th and 7th Ave; chances are you will find me wearing something similar at least once a week. My everyday style is very much about comfort and functionality so I love that it gives you all of that with great colors, patterns and cultural style references. I’m also inspired by my rap clients (who are pretty cool if I do say so myself), their style and influence has definitely rubbed off on me. I call it “urban chic”….I live for a nice heavy chain, fly gold jewels and love a man in a dope watch!Karleen-Roy-4

So by now, we definitely needed advice on how to break into the entertainment industry from self-made Entrepreneur, Roy. Her advice was simply, “to get into it because you genuinely have an interest in the field, and not because you want to be around famous people or hang out with them.” She added, ” In today’s age, which is much different from when I started, people are really eager to hang or associate themselves with famous people so they can stunt for the Instagram likes. Those people never last because they are in it for the wrong reasons.” Karleen-Roy-2

What are some things you should know as an industry hopeful? Looking the part is certainly key. As a “walking billboard” for her brand, Karleen vocalized being polished and looking the part are definitives for success. “Image is everything, especially in the social media space that we are in. When you look the part, people definitely take notice.Karleen-Roy-6

Words of wisdom, indeed! Some finishing tidbits including her memorable career-stopping moments (such as coffee with Madonna) and Oprah calling Sean Comb’s office to thank Roy for the the bottle of Tequila that had been sent to her. “She did not call to speak to him, she asked FOR ME! She said, “I know it’s from him, but I know the assistants are the ones to usually send it off so I wanted to say thank you, to you and him.” I think I died!” 


Ending our interview, we had to ask her thoughts on #BlackGirlMagic, considering her whole life seems to exude it. ” I’m totally in love with the Black Girl Magic movement! It is the epitome of pride and support amongst young Black women. I’m thankful for my supportive village of black girlfriends and friends in the business as we always support and champion each other along the way which is something we all need. Every girl can use a little encouragement and push in their lives.” Amen!Karleen-Roy-7

For all those entertainment industry hopefuls, entrepreneurs, and fellow #BlackGirlMagic supporters just trying to find their way, this interview was heavy with gems and advice. What do you think? If you’ve fallen in love with Karleen Roy or even want to learn more about The Vanity Group, check them out on IG: @VANITYGROUPNYC and their site, WWW.THEVANITYGROUP.COM.


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