Karleen Roy on Working for Diddy and Building an Empire with The Vanity Group

Karleen Roy on Working for Diddy and Building an Empire with The Vanity Group

Karleen Roy
Karleen Roy

If you asked a group of people what their career aspirations were, most of them would probably say they’d want to work with a mogul like Sean Combs. That was once a dream for Karleen Roy too, but she’s already checked that one off her list. And now with the recent launch of her new luxury management company The Vanity Group (@VanityGroupNYC), Roy has her sights set on higher ground: becoming a mogul herself.

Equipped with the “Navy Seals-like” training she received working as Combs’ executive assistant over the last five years, Roy launched her company with a lavish celebration at the Armand de Brignac showroom and is quickly building an impressive client roster with names like Fabolous, Ne-Yo, Adrienne Bailon and more. Here, Roy talks about working for Combs, obstacles she encountered as she launched her company and where she hopes to be within the next few years.

Hashtags + Stilettos: What is The Vanity Group (TVG)?
Karleen Roy (Roy): The Vanity Group is a luxury lifestyle management company. There are a lot of luxury lifestyle management companies out there, but our niche is that our brand personality is a bit more edgy, sexy and fresh. Someone has to preserve the sexy!

H+S: What inspired you to create TVG?
Roy: While I was in my position at Bad Boy as Mr. Combs’ executive assistant, I really loved my job and I loved that I could get just about anything done successfully. So from that, I started to think in the back of my mind that this, lifestyle management for well-known individuals, could develop into something bigger in a more unique way. … At The Vanity Group we offer three services: bespoke event producing, luxury concierge services and finally, talent relations.

H+S: What was one of the biggest obstacles you had to overcome to launch TVG?
Roy: Entrepreneurship is something that a lot of people don’t understand or are afraid of. So starting off, I was fighting for respect and recognition that [The Vanity Group] was indeed my new job, my career and not just something I was doing on the side.

H+S: Which TVG projects are you most proud of so far?
Roy: I am proud that we got the opportunity to produce, Fabolous’ “Great Fabsby” birthday event in New York City. It was a huge success that we planned in less than 4 days – it was a miracle!

karleen roy
Roy celebrating the launch of The Vanity Group last October.

H+S: You’ve worked with a lot of different entertainers and moguls besides Sean Combs: Ne-Yo, Adrienne Bailon and Fabolous among them. What advice would you give to someone who is interested in working with celebrities at this level?
Roy: My advice for someone that is interested in working with celebrities is to know your place and do not get caught up in their life. You are there to work, not hang out and get comfortable.

H+S: How has your former role as an assistant to Sean Combs paid off with your new business?
Roy: Working for Mr. Combs was the best training there is – like training for the Navy Seals. He’s the consummate professional so I’m thankful I was able to learn those skills because the [business] acumen I inherited is priceless. Also, a lot of my clients have come from people I met while working at Bad Boy. Relationships and referrals are key in this business.

H+S: Who is your dream client?
Roy: My dream client would be either Magic Johnson or Oprah Winfrey. I respect the empire that they have built so it would be an honor for me to have them as a client.

The Vanity Group
The Vanity Group launch party.

H+S: What’s the best piece of business advice you’ve ever received or learned along the way?
Roy: I’ve received a lot of great advice along the way, but I can say the best piece of business advice I’ve received is, “You cannot run a Blockbuster business in a Netflix world.” Make sure your business is up-to-date and current in your ideas and practices.

H+S: What are some of your personal or professional goals for this year?
Roy: I love to write, so I would like to maybe incorporate a blog for the brand as a professional goal. And [on a personal level,] my father, who once was a successful entrepreneur, has Alzheimer’s. So I’d like to run in a marathon to raise money and awareness for the Alzheimer’s Association.

H+S: What advice would you give to aspiring entrepreneurs?
Roy: My advice for any aspiring entrepreneur is to believe in yourself, because if you don’t believe in yourself, no one else will. Even in the dark hours, keep the faith. I would also tell any aspiring entrepreneur that if you treat your idea or small business like a side-hustle so will the rest of the world. Respect yourself, your brand and the services you offer because it has a high value.

H+S: What is your favorite inspirational quote?
Roy: As a child of hip-hop culture I would have to say one of my favorite inspiration quotes is, “Scared money don’t make no money.” I did not understand it when I was younger. But now that I am business owner I completely get it. If there is no risk, there’s no reward. Period.           

H+S: What’s next for The Vanity Group?
Roy: My goal for the brand in the next year is to work towards [becoming] a bi-coastal company. My dream would be to have an office in Los Angeles and NYC.

A version of this story also appeared on Madame Noire.