There isn’t one area of society that the COVID-19 pandemic has not affected. With millions of Americans infected with the respiratory virus and hundreds of thousands dead, the terrain is looking very bleak as we head into 2020. Even popping rappers are feeling the brunt of this historic sickness. With show money slowing up and studios closed, we’ve seen a few notable emcees get taken down by the law for crimes ranging from racketeering to wire fraud.
It doesn’t appear to be a good time to be in the music game, but there are still millions of dreams of hitting the big time once COVID is behind us and there are countless individuals working hard toward those dreams. One example is a man known around his native New York City as Dee Boss. When he came home from prison after 20 years on a murder rap in October 2013, he took to party promotions under the banner of Boss Baby Entertainment. Last year, Dee Boss received a chance to pivot into the music industry Boss Baby Entertainment became a full-fledged record label. The Harlemite now has a stable of young, hungry artists with whom he is very hands-on. Their music is streaming online, their videos are spinning on YouTube and their faces could be seen gracing coveted billboards in Times Square. Dee Boss knows what it is to be down, but through Boss Baby, he plans to rise higher and higher until his name joins the other legendary moguls that hip-hop has given to the world.
We recently sat down with Dee Boss to discuss his Boss Baby Entertainment venture, his past and his future. Check out what he had to say below:
Don Diva: What was life like coming up for you in Harlem?
Dee Boss: Just like any typical young kid coming up. And my case, I did come up in a nice household. My father and my mother were both married before I was even born. And so they were pretty much good working people. They both were into music. My household was pretty good. I’d come up in a household with five boys, no sisters. [We were] regular kids: playing every day, going outside like all of Harlem kids, just having fun. Even under the circumstances of us being in a rough area of Harlem, it was still pretty much good times. That’s neither here or there. Times change and people change, especially when you’re a youth, when you’re a kid growing up around seeing drugs and violence. Other than that, my life was pretty much cool at a young age.
DD: How did you get into music?
Dee Boss: Actually, my father used to background sing for Luther Vandross. He also was a DJ, but he was heavily into music. R&B music specifically and hip-hop as well, but my father always played music in the house on Saturday mornings during the week. That was his life. He thought he was a fly motherfucker. All he wanted to do is get fly and play music and do his little thing. That was his zone. My brothers and I picked up the knack for music from my father.
DD: Are you a musician yourself?
Dee Boss: No. I’m not a musician, but I used to rap. I started rapping at a young age. A kid named Olori Rock Ski from Grant Projects used to rap all the time around me and he was doing well. He used to be with Doug E. Fresh, and I wanted to do the rap thing. One day I asked him, could you write a rap for me? He said, ‘No. You have to pay me to write a song for you.’ I was like, ‘You’re my man.’ He wasn’t trying to let up. So I just started writing myself. I was actually good at it. After a while, I just stuck to it and I just started getting around a lot of different people that was doing music. People like Big L, McGruff, Loon, Chauncey Hawkins, a whole bunch of others, and we were always doing it, and the rest is history. Music became my thing.
DD: Were you rapping under the name Dee Boss?
Dee Boss: At first I was rapping under the name Double D. Back in the days, we had names like that, Double D and shit like that. But then after a while, people in my neighborhood started calling me “Boss,” because I had this boss-type attitude with me. I want to run shit, and then, it also came from me hustling in the streets. And I was just organized and liked to delegate responsibility at a young age, so they used to call me Boss. So I changed it up Dee Boss.
DD: How would you describe the music scene in New York City when you were coming up compared to now? What is the difference between the music industry back then and now?
Dee Boss: The difference between then and now is content. Back then in the ‘70s, because I’m a ’70s baby, but I grew up in the ’80s, listened to a lot of ’80s music. So you had a whole lot of diversity with the music and people were saying shit. People have really good things to say about what was going on during those times in the city. Everything from Sugar Hill Gang, I mean, not really Sugar Hill Gang. They was more mainstream hip hop party type dudes, but I’m talking about Grandmaster Flash, De La Soul, Public Enemy, all those different types of groups had things that they touched on as far as social content. Now everything is kind of watered down. It’s not real content to the point where people are thinking about real social issues that affect our everyday lives. It’s more geared towards that party vibe. Just people trying to feel good as opposed to just actually trying to say something meaningful.
DD: When did you start Boss Baby Entertainment? How did that come about?
Dee Boss: Boss Baby Entertainment wasn’t an actual company at the time. I didn’t have it as an LLC, but I used to use the name Boss Baby Entertainment around 2016, 2017, because I was a party promoter. So I just used it on fliers and stuff like that so people would just know the name whenever I’m doing a party, but it didn’t actually become a company or a label until 2019, so last year sometime.
DD: What made you want to start the music record label?
Dee Boss: It’s funny because I actually got into by a mistake. A friend of mine, who I was in prison with his name is Jesse Spruils, has a company called Guapstar Entertainment, and he has a niece named Tykeiya that he was working with for a few years after he got out of prison. One day he called me because he needed help getting a Maino feature for her song, “Pretty Kitty.” And I was pretty much the only person that he could reach out to that can help him with it. So I helped him get the feature. I actually liked the song and said, well, we could get the feature and we could do something with this. And he gave me the offer to work with him on her project and kind of do a joint venture with my company Boss Baby Entertainment and Guapstar Entertainment and push her as an artist. So that’s how I got into the music business.
DD: You said you did some prison time. Do you mind speaking on that a little bit? What happened there?
Dee Boss: Absolutely. I did prison time for a few different crimes. One of them was murder. Actually, I did 20 years altogether. I came home in October 2013. And I went to prison for guns, drugs, all the shit that young people go to jail for when they out in the streets heavily. Murder, guns, etc..
DD: Would you say that your time in prison has helped shape you into who you are today and how you handle your business?
Dee Boss: Absolutely. When I went to prison, one of the things that I took seriously was my education. I started early as opposed to a lot of people that came in prison at my age. Some people were just in the yard working out, playing basketball, running around doing shit that most people do in prison that got a lot of time and don’t see no hope. I took education very seriously. I went on and got my GED, and from GED, I got into a computer literacy program. I started working at this program which was a braille program, where I learned to read and write braille and transcribe braille for the blind students that’s in schools all over the country. From there, I got into other different types of programs. I became HIV/AIDS certified counselor. And then I went to Bard College in the prison and got my associate’s degree. Came home, went back to school for real estate and urban development at Baruch College for another two years. And here I am with my own business now. So yes, in prison, I did take my time to educate myself and prepare myself for what it is that I’m doing right now with my company, as well as other things that I’m doing in my life.
DD: You have a few artists on your label. What do you look for in artists to sign to your label?
Dee Boss: Content. Again, the thing is, with this generation now, you’ve got drill music, you’ve got trap music, you’ve got all that type of stuff. And a lot of these young artists out here today, that’s what they focus on because that’s really all they know. But then you have some artists out here that got that old soul. The 22-year-old, the 24-year-old artists out here that’ve got some history with they family, like their mothers and their father used to listen to old school music and they kind of picked that up and trying to carry that tradition on.
So that’s what I look for in an artist to see if they’ve got an old soul, if they’ve got any history with music and if they have any history with music and knowing how to construct songs, that mean something, those are the types of artists that I look for.
DD: How do you go about finding them?
Dee Boss: It’s funny because a lot of times I don’t actually look for the artists. People send them to me. And based off of what I see, I go on Instagram where they send me something or something that they did on YouTube, I’ll give it a shot. I’ll look at it and see if they fit into what Boss Baby Entertainment is about. And if they’ve got a nice flow, they’ve got a nice look, depending on how they use their words, those little things are important to me.
And especially if they can visualize things and put it on paper and paint pictures with they words, those are the things that I actually look for in my artists.
DD: You said you look for artists who are about what Boss Baby is about. What would you say Boss Baby is about?
Dee Boss: Boss Baby Entertainment is pretty much about team work, hard work, and dedication. Those are the three things that our company is about, because we are very dedicated in what we do and we don’t slack. We don’t slack at all. We get up every day with the attention to trying to better ourselves and better others around us. So that’s what we want our music to reflect. If you’re not trying to better yourself or better the people around you, then it doesn’t work for us because it means you’re selfish artists. And nobody in our company is selfish. We the type of people that we see, the youth we see, young talent, and then we try to work with them and try to put them in a better position so they can make their lives better, make their families better, make their friends and everybody’s situation around them better, through their art, through their work, through their dedication. And that’s what we’re about. That’s what Boss Baby is about.
Boss Baby Entertainment is not only just Boss Baby Entertainment. It is a network of different companies and groups that’s working together. For example, we have VENG, which stands for Value Everything, Nothing’s Guaranteed. That’s my brother, Frank Cook’s company. He does music production. He raps, too, as well. He has a video out right now with Kool G. Rap, Cory Gunz and another artist that he’s working with named Norman Bates. Fire video. It’s crazy.
I also have another brother, Mont. He has a company called Firehouse Entertainment that we work with, and they do management. Not only management in the music industry, but they also do stage management with Rick Ross and a whole bunch of different artists.
Then we have another company named CRC Entertainment. They have artists in Brooklyn named Mally G. Good kid. He’s about to come out fire. So we work with them too.
And then we have the president of my company, her name is Keona. She has a company called Music and Mortgage. And she works with us as well, helping us get finance and helping us get resources as well. And she was the one who actually got Bria, the Max B feature. So she’s heavily into music herself.
So it’s a conjunction of a whole bunch of different companies working together to make things happen, to push each other through the door. So that’s what Boss Baby Entertainment really is. It’s just all of us getting together, trying to make shit happen for the youth.
DD: When you’re going into developing these new artists, what goes into it? What is your job as the founder of Boss Baby? What is it that you do with artists that takes them to the next level?
Dee Boss: That’s a good question because actually I’m very hands-on with my artists. I’m in the studio anytime that my artists are inside the studio because I have a musical background. So my way of developing them is picking beats for them. I know their voice and their sound. I pick a beat for them, or I pick certain producers that works with their sound. I might come up with an idea or send them a track, for example, and they’ll listen to it and then they’ll come up with an idea and we’ll shoot the ideas back and forth, and then we’ll get in the studio and work on a song. If it comes to their look, I’ll give them stylists. For example, I’ve got an artist named Bria Ford and she’s a woman. I give her everything that she needs around her. I’ll go from giving her beats, and she picks her own beats as well. Anything that she needs to be a professional artist to make sure that her crap and everything gets developing the way that she’s supposed to be developed. Those are the things that I play. Financing, all those different things that executive is supposed to do.
DD: With the COVID and everything happening, everybody in the music industry are saying it’s harder to make it happen. How have you been adjusting to everything that’s happening now and making it work for your artists?
Dee Boss: Actually, I’m surprised. I’ve been adjusting to it very well because of the resources that I have. For example, a lot of the studios are closed during COVID. A lot of engineers don’t want to work because they don’t want to contract COVID and pass it on to their families because there are a lot of people in a studio. The good thing about myself is that I have a good engineer. His name is Craig The Engineer. He has a nice resume and he’s actually a part of Boss Baby Entertainment. He’s a partner in Boss Baby Entertainment. So, getting studio time, getting the right studios, like the cutting room and Fight Club IMI and Quad Studios, he has access to all those studios. So getting work done is not a problem. And then again, we have other resources to help us push our records. There’re a lot of people still working during COVID because people still have to pay their bills. So it’s just a matter of you getting in touch with the right people that are still doing things and keeping it moving forward. People still got to live. So it’s not really going to anything, but it’s more about the resources that you have available that’s willing to work with you and make sacrifices for you to get your work done.
DD: What do you have planned for the near future with Boss Baby? What can people be on the lookout for? What can they expect?
Dee Boss: I have a few things going on. My artist, Buttah B. NOVA, he’s got a project called Ain’t EZ Being Beezlyy coming out. It’s a mixtape, and that should be out on December 12th. It’s a fire ass mixtape. Young boy from the Bronx, he putting it down. He’s coming straight like that. I have his project coming. Bria Ford, her EP coming up. It’s untitled right now, but she has a single coming out with Dave East and another artist named Deon Young, song is called “Ryder.” That should be dropping on New Year’s Day. So that’s what I have there. We’re working on her EP. Also, I have another artist named Berg O from Utica, New York. He has a song that’s coming out right now called “The Village” featuring Buttah B Nova, Leezy the Don, Black Grim and Dame Dash. So that’s another single that I’m about to push out. Bria Ford also got a single, her remix. She has a song out right now called “Legendary.” She has a remix single coming out with Max B. That’s also coming out at the beginning of the year. So these are the things that we’re working on.
DD: Five years from now, what do you see as the future of Boss Baby Entertainment?
Dee Boss: I see us doing a whole bunch of different things. Not only music. Especially during COVID, because it’s hard for people to do shows out here and get revenue streams from other different sources of music. So I’m trying to tap into movies; Anything dealing with entertainment. Movies, comedy, podcasts, you name it. The list goes on. A lot of people got talent out here and if I can find people that are willing to work and do things that they like to do in the entertainment industry. I’m more than willing to invest in them. Not only my finances, but my time to try to add on to the Boss Baby repertoire.
DD: Is there anything else you think you want to add that we haven’t gone over?
Dee Boss: I just want to give a few shout outs to my man, my partner Baby J, which also the name Boss Baby comes from Dee Boss, Baby J. Shout out to my other partner, Warren, whom we call Dub, putting in a lot of work with me. And also Craig the engineer, once again, because he made a lot of things happen. That’s just pretty much it. We try to give people the flowers while you’re alive now. My man Bootsie from Harlem and my man Shine Boy Double. Two dudes that’s making things happen for us down in North Carolina, and Waleed Coyote from Empire Records, who also just signed us. That’s another thing. We just got signed by Empire Records, the distribution deal. We’re about to make it happen. We about to make this thing pop.