When Diddy Has You on Speed Dial
The "Olivia Pope of the music industry" tells us how she got there.
Karleen Roy’s mom calls her the “Olivia Pope of the music industry.” We mean, she’s not wrong. Consider this: when one of the high profile clients she works with at her company, The Vanity Group, asks, on December 30th, for her to throw a New Year’s Eve party in St. Barths, she actually pulls it off. Or, as she recounted to us when we stopped by her Manhattan office, how she once got an all-black outfit to a client who was on a yacht off the coast of Ibiza because they decided they wanted to go to Riccardo Tisci’s birthday party (as you do). Yes, in case you were wondering, Roy knows how to hustle. And she’s made a very real business out of her somewhat superhuman ability to do anything, at anytime for some very, ahem, high-profile people. Herein, she tells us what it’s actually like to start a business, the best advice Diddy ever gave her and how she deals with the anxiety that comes with her job description.
ON HOW THE VANITY GROUP WAS CONCEIVED:
“The Vanity Group was first [started] while I was working at Bad Boy [Entertainment] for Mr. [Sean] Combs, because I kept saying, ‘I’m really great at my job and I do it really seamlessly. Wouldn’t it be awesome if I could take some of this and do it for other clients that were in the same space? High profile individuals—artists, musicians, actors—because they all have similar needs.’ The issue is finding good people who can facilitate those needs on their behalf. So a crazy request—from ‘I want to jump out of a helicopter in the middle of Miami, because it’s my birthday’ to ‘It’s my wife’s birthday, and I want to get her this pink crocodile bag, but there’s only one in Paris, so I need someone to figure out Point A to Point B.’ That’s something that I did very easily. It just came naturally to me. So that was the basis of how the Vanity Group started to bubble and bake before I put it in the oven and was like, okay, now we’re cooking it!”
ON WHAT SEPARATES VANITY GROUP FROM THE REST:
“It wasn’t until after I started doing research years later that I realized that this was even a thing—luxury management lifestyle companies. There’s a lot around New York City and other cities where high net worth people live, but the difference I saw, in doing my market research, was that the same types of companies did not have those one-on-one relationships with the artists. That is one hundred percent what separates what I was doing from what the other companies were doing. They were going through managers or third party people and there was no real connection, and I honestly said no [to that way of running things]. First, we have these relationships, and second, I’ve actually been in those shoes. I think you can better serve someone when you can say, ‘Oh, I have gone to Ibiza and partied all night, so I know exactly what you’re looking for.’ Or, ‘I’ve been at St. Tropez, and I know that you can’t find a hotel, because no hotels exist, and you really just need to get a boat.’ Or, ‘I know you can be at Cannes Film Festival, and you can have the biggest yacht and guess what, you won’t have dock space, because it won’t even fit your 200 foot boat.’ So I think it made it a lot easier for me to navigate it, because I’ve actually done it before.”
ON HER FIRST (NON-PAYING) JOB AND WHEN HER LIFE “WENT LEFT:”
“When I walk down the street, I think, ‘How in the world did I get here?’ [Laughs] I knew that I did not want a boring career. That’s what I knew, and that is why I moved to New York City. I moved to New York because I wanted to work in the music business, and I thought as a twenty-three year old girl that I wanted to be a publicist. I went to school for it, so I thought that was a good discipline that I could get myself into. My first job was an unpaid internship at Def Jam. I made no money. My dad thought I was completely crazy. [Laughs] He’s like, ‘I don’t understand, who works and doesn’t get paid and doesn’t have insurance? No one does that with a college degree.’ But I knew that you had to start some place, so I worked at Def Jam in publicity. Then I left there for Sony Music, and I worked for Ne-Yo, and then the opportunity came about to work for Puff. With that job, my life went left, and I just had to go with it.
Working for Mr. Combs is the best thing that could have ever happened to me. He always says, ‘If you can work for me, you can work for anybody.’ [Laughs] He, one hundred percent, is one of the most brilliant people that I’ve ever had the opportunity to work for. He doesn’t take no for an answer. So if your direct boss won’t take no for an answer, you just have to imagine the level of going above and beyond to get things done because he just won’t settle for anything less. He won’t settle for anything that’s mediocre. Now that I’m a little bit older, and have stepped away, it absolutely was the best training that I could have ever asked for in my whole life. I wouldn’t trade it for the world.”
ON THE THREE THINGS EVERYONE WHO WORKS FOR DIDDY-LEVEL PEOPLE SHOULD UNDERSTAND:
“I would say to anybody [working for a high profile person] that [number] one, you have to be a very humble person. [Working for Mr. Combs] was one of the most humbling experiences of my life. Two, you need to take the meat and leave the bones. I don’t know if you’ve ever heard this expression, but I’m from the country, and we always say it. It basically means don’t listen to the extra shit that’s going on in the realm—like the women, the models at the party, the drinking, the hanging out late at night, the screaming, the music, all of the excitement that goes on in the entertainment industry—keep your eye on the prize, the meat. Keep your eye on the bigger picture.
There are so many young people that have the opportunity to work next to these icons that get too caught up in the ‘extra-ness’—I’m making that word up—that’s going on and they’re not able to do their job effectively. Or they’re one of the people that get caught up, and they’re not able to succeed because they weren’t there for work in the first place, they were there to party. I see so many people like that come and go in my career because they were in it for the wrong reasons.
Third, always realize that the wilderness is not punishment, it’s preparation. So while you’re on grind mode, and you’re a young person coming up in the inner streets, all that’s going on is just preparing you for the next step in your career. While you’re in the thick of it, sometimes you might not get that at the moment, but that’s what I always tell young people when they ask me.”
ON THE NITTY-GRITTY OF STARTING A BUSINESS:
“The Vanity Group was actually birthed secretly in 2009, while I was still working for Puff. I was trying to put the puzzle pieces together as far as what I needed to start my own business. Do I need an accountant? Do I need an attorney? Do I need a business plan? I was just going off of pure passion, figuring things out and making it work as I thought it needed to work. And then it was maybe in 2012 when I was talking to a business mentor, and she was asking me like, ‘What’s going on with your business?’ And I was like, ‘Hey, it’s going. It’s moving and grooving.’ And she was asking, ‘Do you have a website?’ I was like, ‘No.’ She was like, ‘Do you have this going on?’ I was like, ‘Oh no, not yet.’ And she said, ‘You can’t run a Blockbuster business in a Netflix world.’ At that moment, it completely clicked for me. I just went into overdrive—like this is something real, I’m doing it, and I’m getting clients, and the work is coming to me very easily. It was almost like, ‘if you build it, they will come.’ So I definitely carved out months to get my ducks in a row—copywriters for the website, art directors for some of the creative aspects we were working on, accountants; just the things you need to have in line when you are starting your business—your LLC, your taxes, all of those things. I was like, ‘I’m giving myself a deadline and we’re just going to put it out there.’ And I said, ‘I’m going to have a launch event to let the world know that this is real, it’s happening.’ The next week, the phone was ringing off the hook.
I was doing the work all along, while I was working for Puff. I was getting calls from Kobe Bryant’s office with a request, or getting a call from Ne-Yo to do a red carpet event for him. So it was like, I’m doing the work, I just haven’t put it out there for the world to see. So it was like, playtime is over. Let’s build it and make this shit hot! And it just worked.”
ON HOW HER CAREER HAS CHANGED SINCE LAUNCHING THE VANITY GROUP:
“My day to day is better because I’m the boss, which means I make my own schedule. When you’ve lived your life for so long where your time is not your own and your days don’t belong to you, it’s a very rewarding feeling to work when it’s convenient for you, for lack of better words. I don’t have it all figured out—I make mistakes all day, everyday—but I feel like I finally have found my rhythm. As they say, good help is hard to find. So that has been a challenge for me just in the last two years—finding a staff that shared my vision, because if you have people working for you that don’t share your energy, it’s just not a good marriage. Maybe they are not as aggressive as you are, or maybe they don’t work all day and all night like you do, and when you have someone in the equation that doesn’t get that rhythm and get that speed, that person is not happy. So it’s very important to me to find people that share my energy. I think you make beautiful music together when you’re in sync.”
ON HER “AVERAGE” WORKDAY:
“I’m usually up by seven in the morning, and I work out in the mornings. I am always on. I have so much anxiety and so much energy all the time, so I try to go to the gym and listen to gospel music and calm down before I read an email that makes me want to scream. [Laughs]If I get up and I listen to rap music, that will make me more intense, so I try to get up in a calm and centered space. Then I come home, I change clothes, and I get ready for my day. I set up my week. I read my emails first thing in the morning; I probably have a kazillion emails and texts first thing in the morning. During the day, I usually set my hours for meetings and site visits. We always have an event that’s in the works, so a lot of times I’m running around to different venues in the city. Nine times out of ten, if you run into me in the day, I’m always going to have on flats. I admire the fashion girls who look so fly all the time and wear heels, but my life is just not set up like that because I’m always running and gunning. In the evenings, I come back home and I’m working and reading emails, maybe until 3AM in the morning. I work really late. It’s really hard sometimes for me to focus during the day, just because I’m such a night owl. Anyone that works for me, they’re getting emails from me like up until maybe 3 or 4 in the morning.”
ON THE TYPES OF PROJECTS SHE’S WORKING ON:
“Every year we usually do Fabolous’ and Trey Songz’s birthdays. And their birthdays are a few days apart, so that’s always a wild week for us. And then, moving into Christmas, a lot of our clients ask us to do their Christmas shopping and gifting for them. There’s the St. Barthes, New Year’s Eve holiday time. New Year’s Eve is a busy time. Things are rolling back to back to back. If it’s not a red carpet event, it’s doing so-and-so’s Christmas shopping, or we have to do a client holiday gift, so there’s always something going. And then there’s always the last minute client who calls on a Monday and is like, ‘I want to have a red carpet event on Wednesday.’ So then we have to stop, shift gears, put our heads together, and move on that in good time.”
ON SAYING NO TO REQUESTS:
“The only time where I’ve had to say no is based on availability—I can’t do it because I’m in outer space and you want me on earth. I can’t be two places at one time. But I haven’t got any crazy requests asking me to do something unethical, where I’m like, ‘Okay, this is where I draw the line.’ I’m thankful that I haven’t had to experience that yet.”
ON THE CRAZIEST REQUESTS SHE’S HAD:
“We’ve had requests on December 30th to do a New Year’s Eve party for 600 people in Miami. I’ve had a client ask us to organize for him to swim with sharks. This time last year, I had a client that wanted to land in a helicopter on a yacht, but he didn’t want the yacht to be docked, he wanted it to be anchored out. So we were running into issues with the coast guard. I had a client that cancelled the elephants for his birthday, but the morning of the birthday, he changed his mind, so we had to get all the elephants back. And getting elephants back is not an easy thing to do. I had a client that was stuck on a boat and needed something all black to wear to Riccardo Tisci’s birthday, so we had to figure out how to get black clothes to the yacht so they could helicopter to the party in Ibiza. It’s never like, ‘Can you get me a reservation? Can you get me a table at 1OAK?’ It’s really, ‘Can you tear down 1OAK and build it back up in purple with polka dots and have a dancing fairy outside in the next five minutes?’ [Laughs] Those are the calls we get! It’s like, ‘Today is the day I’m going to have a heart attack.’ It’s always a challenge, but I actually love it. The most recent one is we had a client who, two days before the 4th of July, on Friday when the banks are closing, they said they wanted to do a party in the Hamptons. We made it happen. I almost died, but we made it happen. My mom calls me the Olivia Pope of the music industry.”
ON HOW TO NETWORK:
“I learned early on as an intern from someone who worked at Def Jam that anybody you meet or call one time, you’re going to need that person again in your career. So save their number and foster that relationship. And I also learned early on to chase the relationship, not the money that’s going to come from it. In this business, that means you really need to take the time to reach out to people and get to know them. Being very pleasant to people has always been my saving grace, and what people have always said when they speak highly of me. Just be very kind to people. Stay in touch for birthdays and holidays. I do a lot of gifting at times when people aren’t thinking about celebration. Everyone does Christmas holidays, but does anyone think to do something in the new year, when people are back at their desks and want to feel good about the year that’s to come? So I always try to think of cool ways to stay in touch with people. A lot of the people that I work with today, I actually met when I was a young intern going to get coffee at Def Jam or going to get the cupcakes for the company office party—those are some of my clients today. Those are some of the people who have been my biggest supporters and who have hired me for projects. It’s so great to take the time to foster those relationships. I think a lot of young people think, ‘What can this person do for me?’ But at the root, you should just try to get to know people."
ON THE BEST ADVICE SHE’S RECEIVED:
“From Mr. Combs I learned that closed mouths don’t get fed. You have to ask for what you want. And also that being emotional in business will have you broke. Susan Posen told me to be slow to hire and quick to fire. And Dia Simms, the EVP of Sean Combs Enterprises said, outwork everybody and don't be afraid to be a woman in a man’s world. And don’t treat your business like a side hustle. If you treat your business as a side hustle, everybody else will. Because perception is reality.”
ON WHAT SHE’S MOST PROUD OF:
“I am most proud of my tenacity. There are so many times I could have given up, or stopped, or gone back to get a quote-unquote regular job when times were hard and the phone wasn’t ringing. Or when clients didn’t pay on time—and that’s a big thing for new business owners and small business owners. When I was young and working at Bad Boy and [there were] days when I had no sleep, I could have just said, ‘I’m going to give up and have a nine-to-five.’ I’m most proud of myself for my level of perseverance. On the days when I still go, ‘I want to give up!’ I remind myself, ‘You’ve made it this far. It’s only up from here.’ So that really is what keeps me going on.”