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Karleen shares a story about leaving Bad Boy Entertainment to start her own company

Being surrounded by Black Excellence in and outside of her home, Karleen grew up with the confidence that she could do whatever she put her mind to. Making her way to Howard and working in a myriad of jobs post-college, one thing always rang true...Karleen approached every opportunity with excitement and resourcefulness. This work ethic got her noticed and she finally received a break getting into the entertainment space working at Def Jam. From there, she went on to Bad Boy Records to personally serve as Diddy's Senior Executive Assistant. Having a front row seat into the inner workings of everything Mr. Combs was involved in was all the fuel she needed to ultimately step out on her own and claim that entrepreneur title. In 2013, Karleen took her side hustle of planning events to the next level and officially launched The Vanity Group. Fast forward to today, the agency has been a go-to shop for Hollywood's biggest names and Karleen has carved a space for herself as an on-camera personality, lifestyle and event expert. Co-Founder of Claima and Former Nike Marketer, Bimma Williams interviews leading and emerging creatives and entrepreneurs of color about how they were able to build their own tables by turning their hobbies, side hustles, and ideas into thriving small businesses. From these stories, listeners will learn how to claim their dream careers by stepping into the world of entrepreneurship. Featuring Melody Ehsani, Jeff Staple, James Whitner and more. Follow Claima Stories and Bimma Williams on Instagram: @claimastories @bimmawilliams LINKS: https://www.instagram.com/claimastories/ https://www.instagram.com/bimmawilliams/ https://www.instagram.com/vistaprint/

Claima Stories with Bimma

7 months ago

- [BJ] So y'all get on your feet and join me tonight in inviting Karleen Roy to the stage. (audience cheering and applauding loudly) Oh my God. - [Karleen] How are you? - [BJ] Doing well, you look incredible. - [Karleen] Hello! I need a bit more energy. (audience cheering and applauding loudly) - [BJ] I know, you gotta tell 'em. That's what I'm saying. (audience cheering and applauding loudly) (BJ laughs) - [BJ] Now, how are you doing tonight? How you doing? How is it being back in town for home
coming? It's been a couple years. You know you got other celebrations right now as well. - [Karleen] I'm gonna tell you guys, it's so funny. Anytime I come back to D.C., I'm literally in tears. I think you posted about this earlier. It's like, it's so many emotions to come back to Howard, to come back to D.C. where there's so many positive memories. It really is like your coming-of-age story as you go through the streets, as you pass by the restaurants. Whenever I'm here, I'm just filled with so
much joy. I had a conversation with myself today. I was like, going to Howard was literally the best thing that ever happened to me and the best decision I made of my very young, 17-, 18-year-old self. So I love being home. It also is my AKA anniversary. - [BJ] That's right! - [Karleen] Got my line sisters and my Rho Phi heroes here, so it's all the things. It's this, it's AKA anniversary, and just any time being back at Howard is a big deal to me. - [BJ] Big deal. Now, you're also from Memphis
as well, right? - [Karleen] I am. - [BJ] And you were just home. How was that? - [Karleen] Home is great. Anytime I go to Memphis, I'm guaranteed to gain seven pounds. (BJ laughs) I eat so much. It's barbecue, it's soul food, it's wings, flats only. It's all the things. - [BJ] I'm with you, I'm with you. - [Karleen] All the things whenever I go home. But yeah, I just was home. We did an annual empowerment event for Black millennials. - [BJ] Right, Owning the Block. - [Karleen] Thank you, so tha
t was super successful, but I'm happy to be here now. - [BJ] Wow, now what was it about that event and creating that event and experience, I should say, 'cause it's much more than just an event. Why was that important, for you to go home and do that? - [Karleen] So on top of of The Vanity Group, which is my business, and we do red carpet events, there are a few events that we own and produce in-house, and Owning the Block is one of them. Owning the Block is a career empowerment experience for yo
ung Black millennials in Memphis. What I realized from traveling the world, especially living in New York, I felt like people in other cities just had a head jump or a headstart over me, because they were exposed to so many things. - [BJ] So much more. - [Karleen] That I was not exposed to. If you live in Memphis, you work at FedEx, you're a nurse, maybe you're a doctor or a lawyer. Any job in the 90s that you can Google, (BJ laughs) that would be your career choice in Memphis. And I would say,
wow, I wish young Black Memphians knew that other careers and other paths existed. So instead of wishing that it existed, I created it. - [BJ] Wow. - [Karleen] So that's what Owning the Block is. It's amazing. It's my baby project that is growing up to almost be an adolescent, and it's a dream come true to see it come to fruition. - [BJ] I love it, you know, and I align with it, right, because growing up, we talked about it a little bit this morning. I live in, I grew up in Louisiana. Oftentimes
, we didn't have exposure to the opportunities and the different career aspects and the different businesses that I'm in love with today. Even the role I'm in today, I didn't even know that I can even do this back then. So, I really love that you've created that and especially done that at home. Now, thinking about home and Memphis and your childhood, what was that like, right? I think your father was an entrepreneur. What was this like? - [Karleen] Growing up in Memphis was the best thing that,
on top of Howard, ever happened to me. My mom had an amazing career, and my father was a business owner. I very much grew up like the Cosby Show. Like, my life was A Different World before I even knew what A Different World was. So I grew up in a community of Black excellence with leaders, with bosses, and with empowerment my whole life, very humble. I go home, I be wearing a fur coat in Walmart. My mom be like, "What is you doing, girl, we in Memphis! (BJ laughs) "Like, bring it all the way do
wn!" So I always say, no matter where I've been in the world, my roots are very still humble. You can hear Memphis in my voice. I don't care what fancy stage I may be on. The country, Southern girl in me lives within, always. - [BJ] Absolutely. Now, what do you remember about seeing your father as an entrepreneur, because I think he had a strong influence on your direction today in the conversations that we've had about him. What do you remember about him? - [Karleen] I remember being a young pe
rson and seeing a Black man run. That was dope to me, like, to be in the 80s where we didn't have Instagram and we didn't have Google, and being a Black entrepreneur was something that was very much unheard of at that time. At a very young age, I saw what it is to run it, to have a team of people, to have an idea and see the idea go from very small to very big. So we talk about white privilege all the time, but there is Black privilege, and Black privilege is not about money; it's not about weal
th. Black privilege can be about exposure. Black privilege can be about being around educated people. Black privilege can be about the opportunity to travel, whether you travel with your cheerleading team or you travel with your church. So I've come from a community of Black privilege, and I feel like we need more of that. So coming from a community of Black privilege and going to Howard, which just throws gasoline on your biggest dreams. Literally, it's how it felt when you graduated, (BJ laugh
s) because I think Howard just has that energy for anybody who goes there, my personal opinion. - [BJ] I think we got a couple people in the audience that would agree with you. (BJ laughs) - [Karleen] Yeah, yes. - [BJ] Now speaking of that, you were able to see your dad take this and grow that, but your mother also had a very instrumental impact on you as well, right? She worked in the arts, and you would get into the arts as well. - [Karleen] Yeah, so my mom worked in the arts industry. My mom
actually is an educator. She had a performing arts high school in Memphis, and it was great having a mother who was in the performing arts, 'cause she was right along with me. (BJ laughs) So I would come home like, "Look at this new routine I'm about to do! "I'ma charge y'all five dollars to watch me perform "in the kitchen," and they'd be like, "Yes, go, girl! "You amazing!" (BJ laughs) So, my parents, they always fuel my wildest dreams. They really never tell me no. They let me do whatever. If
I wanted to charge my neighbors three dollars to do a lame routine I've been doing for the past six weeks, like, they were okay with it. So I felt a lot of freedom growing up, and I think that's because I had my mom, who was very artistic, and then my dad, even though he was a businessman, and with businessmen, it's like, if you don't make dollars, it don't make sense. But he was a dreamer, so I had the best of both worlds. - [BJ] Did any of that seem unusual to you, like when you thought about
some of your friends growing up? - [Karleen] Not at all. Everybody in my community growing up, somebody's parents or somebody's family was somebody. One of my closest girlfriends, her parents owned 27 McDonald's in our hometown. - [BJ] 27 McDonald's? - [Karleen] Or my neighbor, they were basically the T. D. Jakes of Memphis, (BJ laughs) or this person over here is the Johnnie Cochran of Memphis. Like, I really grew up in a place of Black excellence. So because of that, I think my lens on the wo
rld is, why can't you do it? - [BJ] Right, why can't you do it, mm. - [Karleen] I've seen everybody else do it. I think that has made me a bit fearless. I don't know if that's to my detriment, but I saw people do it at an early age, and I always say, if you've never seen somebody do it. - [BJ] You don't know. - [Karleen] You don't know that you can't do it. So I was grateful to come from a community where people were on their, and I was able to see it and just be groomed from it. You never know
that God is grooming you when he is grooming you. I never had a dream of being an entrepreneur or a business owner. I don't even know how to check my account balance online. (BJ laughs) I can't do all of these things, but I think that God is usually like, preparing us, and we don't even know it. - [BJ] It always seems to work its way out. I think one of the things that was interesting that you share, which is super important, which is why we're doing the work we're doing tonight, is you saw a lo
t of these things growing up so that when you're stepping into your power, it doesn't seem abnormal to you; it just seems like what you should be doing in the first place. (BJ laughs) Did you ever have this pressure, where you felt like you had to perform because your parents were performing at a certain level in their respective places in their careers? Did you ever feel like you were like, "I need to perform at this certain level?" - [Karleen] I never felt like that, and I would say in my life
, I've always been the average C student. I never got straight A's. My parents never cared about that, but I think there's an old saying go, "If you have the vision, you can hire the intellect." So my parents were okay with me just being a child that's the school of the world. So I never felt pressure to perform. I will say, though, that when I graduated from Howard, I felt pressure to do something. (BJ laughs) Everybody at Howard is graduating doing something. "I'm going to work at Goldman Sach
s," or "I'm going to work at Ford," or "This company "did this internship with the School of Business, "so this is what I'm doing," and I did not have a job or any opportunities. And that's what I mean by Howard is a school of competitive spirit. It's like, all your peers are doing things. - [BJ] Are doing something. - [Karleen] So you wanna do it too. So I didn't feel the pressure to perform in my coming of age, but graduating from Howard, I definitely felt the pressure like, oh, I need to do s
omething. - [BJ] Yeah, and I definitely wanna get into that, 'cause you definitely did something, some things. (BJ laughs) But before we get into that, what did you first wanna be? What did you first aspire to become? - [Karleen] I have a few things. My father, a very wise businessman always says, "You're gonna go through seven jobs "before you figure out what your career is." - [BJ] Hmm. - [Karleen] So it's okay to take a journey and figure it out. I first wanted to be a hairstylist, 'cause my
grandmother was a hairstylist. Then I had a terrible acne problem when I was an adolescent, and my mom took me to the dermatologist. I never knew what a dermatologist was, and so in my little 12-year-old self, I asked this woman, I said, "What are you? "What kind of doctor are you?" She was trying to relate to me as a young kid, and she said, "I make people feel beautiful." I said, "Well, that's it. "That's what I'm doing for the rest of my life. (BJ laughs) "I'm making people feel beautiful." I
was that impressionable, so I thought I wanted to be a dermatologist. And I got to Howard and majored in biology, and I either failed my first biology class or I didn't even get through the first one. I said, "Well, biology is a rap for me." (BJ laughs) So I Was figuring it out for a long time. Now that I am in my big age, I actually think it's so crazy to ask a 17-, 18-, 19-year-old child to decide right now what you wanna major in, and this is gonna be the job for the rest of your life. - [BJ
] Of your life. - [Karleen] I think it's unfair, because you haven't lived. You haven't traveled. You haven't met other people, so how do you know what you wanna do when you haven't lived and failed and succeeded and bumped your head and got in trouble and figured it out. I think you really need to, you don't know it then, but you have to give ourselves grace to figure it out. So I wanted to be a lot of things, just because, I didn't know, and that's the beauty of being young. You can just dream
and do whatever you want to. - [BJ] Dream and do whatever you want. I think it's important what you said there, is that whatever you decided then doesn't always have to be what you go with next year. - [Karleen] But we don't know that! - [BJ] We don't. We think like, the decision is finite. (BJ laughs) - [Karleen] Our college counselors and whoever your advisor are in college, they're not telling you, "Pick a major, "but you can create whatever life you wanna create." It's like, "I major in thi
s, "so this is what my life is going to be." It's like, we evolve in thought. We evolve as people, and it's like, actually, I want to do something different, and that's okay. - [BJ] Completely different, right? If you think about what you're doing right now, is that using the degree that you actually went to? (BJ laughs) - [Karleen] Actually no, I think my degree that I'm using right now is a degree of Howard University. - [BJ] Hmm, speak on that. - [Karleen] Which is, getting it done, which is
figuring a way when you don't have a way, which is walking in the room and feeling like you're that girl or you're that dude and your life is your one runway. I think that the spirit of Howard is completely my lens of how I see the world. So my degree in sociology and my minor in PR, absolutely not, which is the trade I went to school for. But the school of Black excellence and walking the walk and talking the talk, 1,000%, and that is because of Howard. - [BJ] Did you always wanna go to Howard?
- [Karleen] Yes! - [BJ] Did you always know that was where you wanted to go? - [Karleen] My parents went to HBCUs, so that's all I knew. It's like, you go to college, you go to an HBCU. Both of my parents are Greek, so like I said, my life was the Cosby Show and Different World growing up. - [BJ] You meant that. (BJ laughs) - [Karleen] Not to age myself for the young people in here, but I was watching Teen Summit. That was the original TRL. - [BJ] Yes, it was. (BJ laughs) - [Karleen] And y'all
don't even got TRL right now! - [BJ] No, we don't have TRL. We don't have any of the things anymore. Don't have any of that. - [Karleen] Maybe it's the original Caresha Please. I don't know. (BJ laughs) But all that to say, Teen Summit did an episode, Teen Summit was like, the hip teen show on BET, and Teen Summit did a Howard homecoming takeover where they were at the Yard, reporting live from Howard University. I'm probably in eighth grade. I'm like, "Yo, this is the most lit thing "I've ever
seen in my life." (BJ laughs) I remember turning to my dad and was like, "Whatever this is," again, I'm so impressionable. "Whatever this is, it's a movie, please sign me up." (BJ laughs) I remember my dad, he researched where Howard University was and he wrote a letter to the school like, "My 13-year-old daughter loves this school." - [BJ] Oh, your dad's brilliant. - [Karleen] No, he was into it, and every year, I was getting literature from Howard, brochures and things like that. So my mind wa
s, off that one episode, I was like, my mind is completely made up. So the power of influence is actually a real thing. - [BJ] Wow, and so, what was that experience like for you, because you speak so highly of and so passionately about it. What do you take away from your education at Howard? - [Karleen] What do I take away from my education at Howard? I think if you have the opportunity to go to an HBCU, and I think that going to college and being at an HBCU is the only thing in our life where w
e're gonna be surrounded by excellent, educated people of color, from your professors to your peers to the people on your cheerleading team to your sorority sisters. That is the only time in our life where we can be surrounded by us and be filled with us and be given our flowers. So my experience at Howard just left me so empowered that I thought that I could do anything. They talk about Howard as the "Black Harvard," but it's like, actually, we don't need Harvard. - [BJ] We don't need that, nuh
-uh. - [Karleen] To make us pop off. It's like, we are what we are, and we are dope. Howard builds leaders for the global community. So, that's why we don't know who went to Howard, I mean Hampton, but we know everybody that went to Howard. Like, we just keep kicking out winners, kicking out winners. (BJ laughs) So I'm happy to be in the family of excellent alumni who've gone to Howard. - [BJ] Yeah, I mean, y'all have excellent alumni. We've been meeting a lot of 'em this week and then a lot of
'em earlier today. - [Karleen] I'm surprised why they ain't got me on the poppin' alumni list. I need to speak to. - [BJ] Oh, we need to speak to somebody. (BJ laughs) - [Karleen] Yeah, the president. (BJ laughs) - [BJ] Now, after you started and finished school, you talked about it a little bit earlier, but you felt like you had this pressure to figure out what you wanted to do. You kinda said you didn't really have something specific lined up. So what did you do? Like, where did that path take
you? - [Karleen] I was a super senior at Howard. Are anybody here Howard students? (BJ laughs) Yes? - [BJ] Yes. - [Karleen] So iLab still around? - [Audience Member] Yes. (BJ laughs) - [Karleen] Okay, so I was at Howard when the iLab first was built, and we thought it was the most poppin' thing. We said, "Oh, iMacs, computers, a printer?" It might as well have been the Apple Store. (BJ laughs) I was in the iLab one day, and I don't know if you remember this, and on the iLab, they used to just p
lay the most ridiculous things, like after hours videos, just all ridiculousness. (BJ laughs) And one day, they were playing Sex and the City in the iLab. I was fake-studying, 'cause I was a C-D student at most, and I was with my line sister, and on the TV screen, Sex and the City was playing. And it was on mute, but I just saw this woman, and she looked powerful, and she looked classy, and she looked funny, and her clothes was fly, and I turned to my line sister like, "What is this show? "What'
s happening?" She was like, "Oh, it's Sex and the City, "and this woman, Samantha, she's a publicist." Again, "That's it, I'm changing my major tomorrow!" - [BJ] "I'm changing my major!" - [Karleen] "To public relations!" (BJ laughs) Like, that's how impressionable I was. I went and changed my major the next day to PR. (BJ laughs) - [BJ] You don't waste any time. - [Karleen] I don't waste no time. (BJ laughs) I get to the bag. - [BJ] You get to the bag. - [Karleen] I call my dad like, "I'm spend
ing another year at school." He said, "Who gonna pay for it?" (BJ laughs) The way my account is set up. So I stayed an extra year in school because I was like, this seems exciting to me. It seems like a fun life. I'd never heard of public relations or what a publicist was. So that is what got me to, barely got me to graduation. (BJ laughs) - [BJ] Barely got you to graduation. But you did get to graduation. - [Karleen] I got there. I was trying to hustle my teacher like, "Bro, if you just give me
a C, my momma and grandmomma "can come see my graduate, please!" - [BJ] "They get to see me!" - [Karleen] Please, yes. (BJ laughs) I was always trying to finagle something. - [BJ] I'm with you on that. The one thing was, I needed to get out of school so my mom can see me, right? - [Karleen] Yes, my grandmother can see me, yes. (Karleen laughs) - [BJ] So you get out, and then what's the plan? Did you go for a job, or did you get a little creative and kinda make something up? - [Karleen] The plan
was to go into public relations, 'cause it looked so easy to the woman on TV. - [BJ] 'Cause you saw it on TV, yeah. - [Karleen] So I applied to every PR company, agency there is, hospital PR, entertainment PR, agency PR, business, like, I applied for everything. I got zero jobs, zero. Nobody called me back. - [BJ] How were you feeling about that? - [Karleen] I was ghosted. I felt defeated, because my friends and my peers had jobs. They graduated and they had things lined up, and I had nothing l
ined up. And during the time after graduation, I happened to go to New York, and I met a young woman who was a publicity assignment at Def Jam. Again, I was like, "I need your life! "This is the coolest thing ever!" She worked in PR in the music business, and I was like, "I love this. "I love everything about what you're doing. "Like, put me on." And she was like, "Well, we're not hiring, "but you can be my unpaid intern, but at Def Jam, "we don't take interns who are college graduates. "So what
you're gonna have to do is "basically sneak in the building every day. "Sneak in as a visitor, wear a visitor pass. - [BJ] Wait, wait, (BJ laughs) you was sneaking in the building? - [Karleen] Basically, it's like you come in like you're fake coming to see someone, like, "Oh, "I'm here to see them," and then you just don't ever leave. (BJ laughs) So that was my everyday life and job for probably nine to 12 months. So she's like, "I can't put you on, "but if you're in the building, people will s
ee you, "and wherever it goes, it goes." My parents thought I was crazy, my very Southern parents, like, "Don't move to New York." - [BJ] "They're not paying you." - [Karleen] "I done watched Law and Order. "They gonna kill you on the subway." (BJ laughs) All these things. I'm like, "I'm going!", just fearless and young. And I packed up my U-Haul truck, and I moved to New York, and I crashed on a friend's couch, and my mom would secretly send me money, and that's my early years of living in New
York. - [BJ] In New York. Now, did you know anything about New York, other than that first time you went? - [Karleen] I didn't. I would come, maybe do an internship over the summer, but I was very much a fish out of water. Had I moved to New York from Memphis, I would have had complete culture shock. - [BJ] Wow. - [Karleen] But the footstep of being in D.C. was a great buffer for me, because that was my first time experiencing city life and things like that. So yeah, my first nine to 12 months b
eing a college graduate from the illustrious Howard University, and y'all know how proud we are at Howard; we think we can do anything; (BJ laughs) I was an unpaid intern, just hoping to get in where I fit in. - [BJ] What was that experience like? What did you pick up on? 'Cause I gotta imagine, if you're there and you're willing to sleep on the couch, then you're willing to probably learn as much as you can while you're in that building surrounded by a lot of different probably really great pro
fessionals. So tell me, what did you start to get into? What did you start to gravitate towards? - [Karleen] One, I was excited to be an intern. As someone who hires people every day, I have a full staff, I don't see the excitement to work. And it sounds crazy. It's like, who wants to be excited to work? I was very eager to work. I was very eager for the opportunity. It's like, Ludacris needed a durag. I'm like, "I'll go get it!" I was just so excited, (BJ laughs) or we need cupcakes for LL Cool
J's birthday. Like, whatever was happening, I was so excited to do it, because I realized it was an opportunity that was gonna set off the rest of my career. So one, I was very excited. Two, what did I gravitate to? I gravitated to people. People easily liked me, and I think it's a very powerful thing to just be a cool person, like, not be weird. I think people liked me, I'm serious. I think people liked me because I was eager and I would be willing to do what everybody else. - [BJ] You were hu
ngry. Didn't wanna do. - [Karleen] Right, I was like, I'm gonna be there early before my boss's boss, and I'm gonna leave after. No one wants to take the x, y to this? I'm gonna do it. I remember walking one day in the rain, literally to get birthday cupcakes for some rapper who was signed to Def Jam. I was just, my shoe was breaking, the rain, my leave out was frizzing up, (BJ laughs) all the things, but I was just so excited to do it. So I was happy to work, and I think I realized at a very ea
rly age that, this is the start of whatever my career is gonna be. We talked about my mom being in performing arts. as a dancer, and anyone who's ever performed, they always say, you got 10 seconds to wow people, and if you don't wow people after the first 10 seconds, it's like, get off the stage please, I am bored. - [BJ] Like Showtime at the Apollo. - [Karleen] Yeah, literally. So I realized I think at an early age the power of presence and how you show up in your first impression with people.
- [BJ] Wow, so you go through this experience. You're at Def Jam. You said it was about 12 months that you were unpaid. And at some point in your career, you also ended up going to work with Diddy, right? What was the transition from Def Jam to working with Diddy? - [Karleen] I was an intern at Def Jam, and a gentleman I met at Def Jam who was an executive in the marketing department, he's like, "Yo, you're like the world's best intern. "You just be doing all the things "that no one wants to do
." (both laughing) He said, "I just discovered this new artist, "and when we pop off, "I would love to hire you to come work with us." I'm like, "Please sign me up. "I would love the opportunity." And the artist at that time was Neo. I think Neo, Rihanna, and Young Jeezy all got signed the same day. So this guy actually quit his job to manage Neo full-time, and they hired me as their first assistant. I got fired about three, four times, but that's another story for another day. - [BJ] Wait, okay
, okay. (BJ laughs) - [Karleen] I was just young and just like, was making sloppy mistakes. So left Def Jam, I had the opportunity to work with Neo's team; then my dad always in the back of my head like, "Do you got insurance? "Do you got a business card? (BJ laughs) "They paying you cash at the end of the week? "This is fugazi." (BJ laughs) So my dad was in the back of my head, and I was thinking like, oh, I need something a bit more buttoned-up. I went to work at Sony Music in the copyright de
partment, but that was a little slow for me, and me just being a hustler, finagler that I am, I met someone at Violator Management, and for any young people in the room, Violator Management is probably the original Roc Nation. They managed everybody who was everybody. It was a management company, it was a record label, and I would work at Sony Music during the day, and I would leave there at like five, six o'clock, and then work at Violator Management. - [BJ] You was really hustling. - [Karleen]
I was just so eager for an experience. I think my first assignment at Violator Management was typing up the itinerary for Missy Elliott's dancers. It was like fifty-eleven dancers. It was so many dancers. (BJ laughs) But I was just so excited that I played a small part in the tour itineraries for her dancers. So it was me being there, and I never got a job there, and Chris Lighty, God rest his soul, Chris was like, "Listen, I can't hire you. "The budget is a rap over here, "but there is an oppo
rtunity at Bad Boy," and that is how I got in the door at Bad Boy, because Chris Lighty was managing Puff at that time. - [BJ] Now, one of the things that's interesting about your journey is you're making a network as you go along. You're meeting people; you're staying connected with them. How important is that along the journey? - [Karleen] It's important. The majority of the people that I met as an intern at Def Jam are people who are now my mentors, people who are my biggest champions, people
who have become my clients and have hired me from work, so relationships are everything. As someone great told me a long time ago, "anybody you meet once, save their number, save their email, "'cause chances are, you're gonna meet them again in life, "and you always wanna be able "to reference where you met this person." So relationships are anything, and I guess that's a little bit of my PR background. I guess my major went to good use someplace. (BJ laughs) But the power of relationships is e
verything. For The Vanity Group, we suck at marketing. Our Instagram has been down for two years, so if there's any social media managers in here, please let me know. - [BJ] They got a couple in the room. (BJ laughs) - [Karleen] But we haven't posted on our Instagram in two years, and we still have been booked and busy and blessed. It's because the power of relationships and staying in touch with people. People know that you get busy whether you talk about it or not. - [BJ] Or not, right. And th
en also, it's the quality of your work, right? Like I said, the perception precedes itself. Now, you know, when I think of Diddy, I get inspired, because I love a lot of what I've seen of his journey. I don't know Diddy personally, but what I've seen. Specifically, I always loved the video in the Von Dutch shirt. You know, you know. (BJ laughs) You know, that video. What did you learn in that environment working so close with someone operating at such a high vibration? - [Karleen] Hmm, working f
or Puff, I have so many "this is the best thing that ever happened to me." Going to Howard was the best thing that ever happened to me, (BJ laughs) being in Alpha chapter AKA is the best thing that ever happened to me, and I would say working for Puff just poured gasoline on my biggest dreams, because I saw a young Black man running it. He was running it. Puff was brilliant. He was a marketer. In the back of his mind, he was an entertainer. I was blessed to be in every room Puff had ever been in
. I don't care if we were meeting with Steve Jobs, or we were meeting with Anna Wintour, or we were meeting with the chairman of Estee Lauder. Because I was his executive assistant, I was in every room that he was in, just sponging up everything, sponging up everything. - [BJ] Wow. - [Karleen] And Puff is just not an artist; he's a businessman, he's a mogul. So the meetings and the type of conversations he is into is just like, mind-blowing, what he always has bubbling. So, that experience, agai
n, it's like, I heard this quote once that said, "The wilderness is not punishment; it's preparation." - [BJ] Oof. - [Karleen] So the whole time I worked at Bad Boy, I was like, "Mr. Combs is so tough on me! "He don't let up, I can't make a mistake. "I'm doing this, I'm doing that," and a lot of times, I just felt like I was on Survivor the whole time. (BJ laughs) But I realize, it was preparing me to be my own boss. And I never had dreams of being an entrepreneur, but seeing someone so brillian
t that always was himself no matter what room that he walked into. He always understood to read the room, but I saw someone come in and not have to code-switch. I saw someone who could come in and be fly and iced out and swag and not feel like, "Oh, I need to put on a suit to have this meeting." It's like, no, I'm coming in as Sean Combs, and y'all gonna deal with it. And so, that experience, again, shaped my lens on life on how I show up now as a boss myself. - [BJ] Now, how do you go from work
ing with Diddy, wanting to be a publicist, wanting to be a dermatologist, to owning your own business? - [Karleen] Are you judging me right now? (both laughing) - [BJ] I'm never judging you. I am the other, opposite of you, not the opposite, maybe a complement of you, of jumping around. (BJ laughs) And then also, I think it's wonderful to have those different experiences, because you don't know what you don't wanna do if you never go through multiple experiences, right? So when did you get taugh
t the place where The Vanity Group was starting to be born? When did you decide, and maybe you didn't decide. Maybe you just like, you kinda rolled into that. - [Karleen] I get this question a lot. So, at Bad Boy, I was Sean Combs's executive assistant. So if anyone has seen The Devil Wears Prada, so when you are a high-level assignment, you do everything. You do the scheduling, you do the meetings, you do the travel, you arrange the social things. You are basically the right hand to the chairma
n, and everybody has to go through you. And on top of everything that I did, a big part of my job was organizing the events that Puff would do, or being the, we would call it the "chairman synergy" person, so the person who gets everybody in line. So whether Puff was getting his star on the Hollywood Walk of Fame, or Jay and Beyonce are coming to the Hamptons in five minutes, and I need someone to get the house in order and organize the most amazing barbecue, or Justin is having his sweet 16 for
MTV, and Karleen, you need to help get things off the ground, I really loved that part of my job. I'm like, this is actually cool. I love organizing things, and I actually got a thrill out of doing things last minute. I was probably at Bad Boy maybe six, seven years, and I got to a point where I started to feel uncomfortable, not uncomfortable because I wasn't happy; I just felt like my skin was starting to stretch. If you guys have ever lived in an apartment, you get to a certain place like, "
This apartment kinda small," or "I need a two-bedroom, or "This car is weird." It's not that you don't love your house. It's not that you don't love your car. You're just starting to outgrow it a little bit. And when you work at Bad Boy, it's kinda like, kiss your family goodbye, you're going to the Navy. (BJ laughs) I realized that I wanted to do something different. I didn't know what exactly it was, but I realized that I had to go to grow. There's no way that I could work for Puff, and me and
BJ had a moment earlier it's like, you can't work for him and interview with somebody at your lunch break. - [BJ] Right, that's not gonna happen. - [Karleen] Ain't no lunch break. - [BJ] No, ain't no lunch break. - [Karleen] There's never a lunch break. - [BJ] You're always on. - [Karleen] You're always on. It's like, I would never be able to entertain other jobs, and I really wasn't in that mindset. But I was in the mindset of, okay, I'm reaching my expiration date. I don't know what I wanna d
o, but I'm gonna take a chance on Karleen figuring it out. So during that figuring it out stage, I would have one foot in and one foot out, one foot in as far as like, I'll interview with other record labels, or I'll interview to work with other celebrities and be their assistant or chief of staff, and on the side, people are asking me to organize events for them. "Can you fly to Saint-Tropez tomorrow and do an event?" Or "We need to be at the Cannes Film Festival, "and we need to organize a par
ty on a yacht," and these are high-profile celebrities that were doing it. After a few years, I wanna say shout-out to my line sisters, 'cause they are a big part of my story, Tameka, who works with me, she said, "You hustling, but this actually is a business, "and you should take it seriously." And I was like, "You think so?" - [BJ] Somebody gotta let you know. - [Karleen] She did. I was like, "You think so?" And she was like, "I know so." So we concocted this fake idea to throw a launch event
for The Vanity Group. (BJ laughs) We planned a whole launch event, and basically, it was like, telling the world that I'm now officially a business owner. And since that moment, it has completely just popped all the way off. It's been nine years, and it's a testament to, if you build it, it will come, and if you treat your business like a side hustle, so will everybody else. So we need to tighten up on how we position ourselves so that you get the respect you want and you show up like the human
that you wanna be. - [BJ] Now, I gotta say one thing. You kinda sped past it, nine years like it was a small thing. That's not small thing. - [Karleen] It's not a small thing - [BJ] It's not a small thing at all. So y'all need to make some noise for that. - [Karleen] Thank you, yes. - [BJ] She's going on 10 years. That's a decade. (audience applauds) Now, tell me about when you switched the mindset from the hustle, side hustle, to fully being in it, that's a whole mindset shift, right? You're re
ally changing your life there. What was it like getting that first client? What did it feel like to finally land that client? - [Karleen] The first client felt like, it's real. People see me. It's almost like, imagine if you have a local bakery, and ain't nobody coming in your bakery, and then finally someone stops in to buy a cupcake. You're like, "Oh, I'm so excited!" (BJ laughs) That's how I felt, 'cause it's like, it's different when you're just like, one foot in, one foot out. But getting m
y first client and doing our first event and it going off without a hitch, it actually affirmed that I was doing the right thing. - [BJ] The right thing. - [Karleen] And it wasn't a big event, it wasn't a big project, it wasn't a huge budget. It actually was with Fabolous, and I feel like he paid me in cash. Like, I went to the studio like, "I need 20,000? (BJ laughs) "I don't know." I was just eyeballing and figuring it out, but it affirmed that I was on the right path. Sometimes all we need is
affirmation. - [BJ] Sometimes all we need is, you get the first one, and it just puts you on the path to keep going. It gives you the confidence that you need. Did you have any help on that first one? Like, how were you going about it? - [Karleen] Oh, it was a straight friends-and-family line sister operation. (BJ laughs) Like, anybody who can help and pull up, it was like, you're hired. (BJ laughs) So I didn't have a full staff by then. It was friends helping me, and I would be paying them cas
h. You know, this was before Venmo and Cash App. I really had community of people who would help me when I needed to be helped. I didn't get my full-time staff where we are running payroll and W2s and worker's comp insurance 'til maybe like, six years in. So it's okay to get there whenever you get there. - [BJ] Right, and everybody's journey is different, right? You can't be spending your whole career looking to see what somebody else doing, saying, "I might not be doing it right." We gotta go o
n our own journey, and we get there when we get there, you know? Six years, impressive, though, you know? - [Karleen] Thank you. - [BJ] That's a great hustle. Yeah, you get comfortable. We gonna chill for a bit. - [Karleen] Where's the wine for my Howard alumni? - [BJ] Oh. (audience laughs) - [Karleen] I'm joking, I'm joking. - [BJ] Hmm, hmm. - [Karleen] They said they gonna send me a case. (BJ laughs loudly) - [BJ] See, now you're gon' get some wine. We really gon' bring that wine up here. Now,
one of the things I wanted to ask you, starting a business, especially coming into this business from where you were, you didn't necessarily have the receipts under your business name that showed like, what you could accomplish. Now, you obviously had the expertise and you had the hustle, but for some of our entrepreneurs here that are gonna start these businesses and they may not have the portfolio to show, how do you go ahead convincing somebody without receipts that you're the one to get thi
s done? - [Karleen] You don't. You're not getting a big client or a big job or your first big nothing without receipts. Your receipts is your brand reputation. The receipts are the work that you've done. You're not gonna be hired, you're not gonna get signed to be a rapper if ain't nobody heard you rap. (BJ laughs) You're not gonna open up the best hamburger spot in town if ain't nobody ate your hamburgers. You actually have to do the work, get under the tutelage of somebody to learn and underst
and. Like, I meet people all the time that say like, "I'm a brand expert," and I'm like, "What brands have you worked with? "What campaigns have you been part of? "What meetings have you been privy to be in?" You just make it up as you go. A lot of people are making up careers, and you see the phony people very soon, because when the rubber meets the road, you see the people who were built Ford tough who actually have the receipts and the people who don't. So I don't think you're getting nothing
without receipts. Your brand is not the fly pictures you take on Instagram. (BJ laughs) Your brand is the reputation of what people say about you when you ain't in the room. "Yo, Karleen is nuts, but she gonna get the job done." (BJ laughs) That's my brand reputation, not, "She takes cute photos." That means nothing. That's not a transaction. That's no value. Like, yeah, that's cute, and branding identity is important, but your brand is your reputation. - [BJ] Reputation, right? And it's so fun
ny you say that, 'cause a lot of people, they think it's the photos, they think it's the logos, and it's like, no, it's, what are you known for? If I gotta say one thing about Karleen, what am I going to say, and that's important to really think about. Like, yes, everything else helps, but you gotta start with the intent and the purpose and the quality first. Now, when you think about your experiences and the experiences that you've put on to date, it's probably a hard question to answer, but I'
m curious to know, what sticks out to you that comes top of mind that's like maybe one of your favorite experiences, and it doesn't have to be your favorite because it was great. It could be your favorite 'cause it was challenging and a bunch went wrong. (BJ laughs) - [Karleen] I'm gonna take a page out of your book and a conversation we had. I think of, and I get this question all the time, like what's your best event or your most ridiculous event. I'm like, one day, I'm gonna write a book, and
y'all gonna see all about it. But I think of events and experiences and seasons, and because I'm in D.C. for Howard homecoming, I'm gonna say one of my favorite events was, we did an event at the African-American Museum of History and Culture maybe like, less than a year after it opened, and it was for a beauty brand that was owned by L'Oreal. And to be at Howard, I mean, to be back in D.C. at this historic museum. - [BJ] Uh-huh, I told you. Shout-out to Lola. (BJ laughs) (audience applauds) -
[Karleen] It's the efficiency, for me. (all laughing) So to be in D.C. doing a beautiful event at the African-American Museum of History and Culture where we were getting so many praises, they were like, "Is this part of the museum?" We were like, "No, we're tearing this down "at the end of the night." But the quality and beauty was so dope that the actual curators thought it was a new exhibit opening. So that was a proud moment for me. Anything that's rooted in culture, anything that's rooted i
n us is just always a favorite for me. - [BJ] I love that, and I gotta come to one of your events. - [Karleen] You have to, you're VIP now. - [BJ] I hope so. - [Karleen] You're VIP now. - [BJ] I don't wanna be waiting at the door. - [Karleen] No, no, we got you. (BJ laughs) I'm about to hire Lola. Lola's gonna get you at the door. (BJ laughs) - [BJ] Lemme tell you now, Lola is excellent. (BJ laughs) Now, a couple months ago, there was a statement that went out by a certain socialite that, last n
ame, Kardashian. And she said, "People don't wanna work anymore," and you strike me as a person that, that's a value for you. Hard work is a value for you. Showing up is a value for you, going above and beyond. Do you feel there's truth to that statement? Do you feel like things have changed generationally, social media maybe has had an impact on that? How do you feel about that? - [Karleen] I think what she said was, "Get off your (bleep) and work." (BJ laughs) And I think because she comes fro
m a place of privilege, that that bruised people, 'cause we're like, how can you tell us get off our ass and work when you have been handed a very beautiful life? I personally am a fan of Kim Kardashian because I think anybody that turns nothing to something, no matter what the nothing is, but I think there's a story of just figuring it out. Everybody has their own story. But I think the get off your (bleep) and work stung people, myself included, but the statement of, people don't want to work
anymore, I have to agree with that. I think Instagram has made our culture and community seem like obtaining success or obtaining receipts is so easy to get, because when we look online, we see everybody's highlights. I'm gonna post about Owning the Block and me getting the key to the city of Memphis. I'm gonna post about me being here. I'm gonna post about me being with whoever celebrity I'm being with. I'm necessarily not gonna post about when we're waiting for a wire and we can't make payroll
this week, because a client has said they was gonna pay us a net 30 and it's net 60. - [BJ] It's net 60. - [Karleen] And we're waiting for the cashflow. I'm necessarily not gonna post about my last three employees who just up and quit, or an employee who stole from me. It's like, we don't wanna hear those stories on Instagram. We wanna hear the happy stories. And think about anybody you've seen on Instagram posting some sad shit. You be on your group chat like, "Oh, you see Karleen? "She on som
e sad (bleep), broke up with her man," or "Things is crazy." (BJ laughs) We don't wanna hear about bad things. Think about anybody you've seen that's posting something like drab. You're like, "Honey, take a seat, I don't wanna hear this." So we are trained to now hear the good and the highlight, which I think makes people think that success. - [BJ] Comes easy. - [Karleen] And reaching or getting to your dreams is so easy to do, and it's kind of like, gone over work ethic. That's why I think the
power of storytelling is so important and caption writing. If you guys follow me on Instagram, I write very long captions, 'cause I feel like the storytelling is just as powerful as your fly picture that you post. So yes, I do think a lot of people don't wanna work, but I think it's not just them. I feel like it's what we are seeing day in and day out, sensory overload of everybody winning, winning, winning, that you think that it's so easy to win yourself. - [BJ] Hmm, well, I know you can't mak
e magic happen. But if you could have an influence as I think you do through your platform, like when I see your stories and also to your captions, I love long captions, 'cause I love the intent and love knowing more about past the picture, 'cause the picture doesn't tell everything. But if you were wanting to see a shift, what would that shift look like? How do you imagine we start to shift things in a different direction, where there is a balance? 'Cause I'm also a little bit critical on my mi
llennial generation as well, where I feel like we're on the hard extreme of like, working all these crazy hours. (BJ laughs) So how do we get to a place where maybe it's a little bit more balanced, but it also is like, hard work is sometimes just hard work, and that's okay? - [Karleen] Being in the room in your community. Like, I get my nails done at this place, and they hate people that's over 40. They're like, "Over 40, oh my God, that's so old." (BJ laughs) This is the thing anytime I go to t
he nail salon. But it's like, you get so much free game by being by people who have already walked the walk and talked the talk. So when we talk about, how do we get over just thinking success is an overnight thing, I think it's about community and surrounding yourself with your OGs that are gonna keep it completely real and honest with you and tell you when you're messing up, and tell you when you need to do something differently or help you negotiate that next job. So I think it is community a
nd storytelling that will probably help us shift people to really tapping back into work ethic versus pretty pictures on Instagram. - [BJ] Yeah, we have to. We have to see that. We have to talk to other people and have a different perspective, right, 'cause it isn't always the glossy stuff that you see. And people start to get that when they start to get in the weeds of things, right? Now, I have one last question before we take some questions from the audience tonight. We have a lot of folks he
re that wanna start businesses or are currently in businesses, and you've been in business for 10 years, going on 10 years now, a whole decade. What's one piece of advice that you would offer to folks starting businesses, starting small businesses? - [Karleen] Remember that the journey of entrepreneurship is a slow bake, it's not a microwave. (BJ laughs) I almost said, almost is the Crockpot, the Crockpot you put the food in in the morning, and maybe it's done by the time you get home from work.
- [BJ] Maybe. - [Karleen] it's not an instant zap thing. So if you're gonna be a business owner and you really are passionate about that life, realize that it is a marathon; it's a journey. There's gonna be some days when you up, "I'm money bags, y'all, I'm spending money, it's up." It's gonna be some days you're like, "Woo, the way my account it set up." (BJ laughs) It's gonna be some days where you have the best clients in the world, and you're gonna have some days where you wanna break up wi
th your client. It's gonna be some days where you win this amazing pitch from a brand, and it's gonna be some days where 18 brands tell you no. And you still have to be able to be mindful that you are on the right path and not give up because someone else doesn't see your worth. Because if you see it, and I always say this. If you (bleed) with you, you don't need no one else to (bleep) with you. And I think when you have that mindset, you're in it for the long haul and willing to play the long g
ame. - [BJ] Karleen, that was beautiful. - [Karleen] Thank you. - [BJ] I literally was just talking about that this week, was about, you just gotta see you first. You can't be so worried about everybody else trying to see you. Once you see you, then the rest of that will come. It follows. But you gotta start with you. Thank you so much for speaking with us. - [Karleen] Thank you, yeah, thank y'all for having me! (audience applauds)

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