Karleen Roy was a senior executive assistant alongside P. Diddy at Bad Boy Entertainment where her instinct and fearless attitude eventually led to industry connections and trust.
After five years with Bad Boy, Karleen took a break to figure things out, paving the way to full-on entrepreneurship. Today, she runs The Vanity Group, a lifestyle management firm that puts her on the road to execute events for the hottest celebrities.
We talked to her about running her own business, who inspires her and balancing her fabulous life.
ESSENCE: I think that so many women have side hustles, and goals, and dreams, but many of us don’t take that leap. What made you say, “Okay, I really can do this on my own”?
Karleen: I am a little bit an accidental entrepreneur. During my time off, I was taking gigs here and there. I didn’t know that luxury lifestyle management was even a thing. In that time, I started to slowly plant the seed for my business. As I was taking jobs here and there, I was doing my own due diligence and research. I learned very early on if you treat your business like a side hustle, so will everybody else.
ESSENCE: Can you tell us about some of the unglamorous sides of being in business for yourself, and how does the positive outweigh the negative?
Karleen: Eighty percent of my business is unglamorous. We just got done with two events for Migos, flew to Miami in the middle of the night, straight with my clothes on that I’ve been wearing all day, got to Miami, and now I’m planning Rick Ross’s daughter’s sweet sixteen. I haven’t ate. It’s like my first time taking a shower in I think like, days. But I think people see me on Instagram and it looks very glamorous and they think that I am hanging out with celebrities.
I am providing a service to them. They are not my friends. The majority of my day and the majority of my time is grinding. It is hard work. I am convincing people to do these things.
It’s more of that and less than the glamour. The positive thing about my business is that I have the freedom to dream and create things that I think are beautiful and create experiences that people will love and I get to choose what I do and don’t want to do. So, if I don’t feel like working, I don’t have to work because I’m the boss. I can do that. That is the glamour of being a business owner to me. You have the flexibility to call the shots. When I worked for Puff, I couldn’t take off a week and go to Memphis to hang out with my family because I hadn’t seen them in a while. I can do that now because I make my own schedule.
ESSENCE: Why do you exemplify Black girl brilliance?
Karleen: Okay, I’m gonna give it to you. I think that I am the bomb … I know that I am the bomb because I am confident and I’m a little bit crazy, and I love crazy people because they are unafraid. And in so many ways, I am unafraid. I feel like how you walk into the room sets the tone. My friends are always calling, like, “Girl, you are not Kanye West.” I’m like, “Yes, I am.” You have to have the confidence. And I really think that confidence is built in your community and your village. I was always around strong women. You know, [I went] to Howard. If you’re not the brightest and the baddest, like, do you even exist?
So, that’s the community that I come from, so I seek the confidence that I have and just like, walk in a room, have my shoulders back, and hit it, and run the show to always try to put my best foot forward. You know, even if that’s just appearance or the confidence to say I can leave a very cushy, amazing job that people would die for and say, “You know what, I want to figure this shit out on my own. And you know what? I’m gonna jump out the window and hope that it works and be crazy enough to believe it.”
I feel like (for) a lot of people, the fear of the unknown scares them. But to me, the fear is, “Damn, shoulda, woulda, coulda.” What if I never tried and this shit could have popped off? I’m just a little bit more insane because I’m willing to jump out the window and try when most people won’t. I feel like is what makes me a badass and I wish more people would try. Just jump out the window and see how you fly, you know? What’s the worst that could happen? Not succeed? But you never know until you try.