People with Passion: business woman Dorothy Claybourne


Interview May 17, 2010

Connecting the dots between art and business...

Business woman, artist, and all-around hip-hop connector Dorothy Claybourne. We are meeting at her studio in Wicker Park’s Flat Iron building. A large white wall leads to her studio; I was first drawn to her by that wall, and the giant black lettering that reached across it, reading: WHY DO PEOPLE HATE HIP-HOP? When I arrive today, “HATE” has been crossed out and replaced with “LOVE.”

Also present is friend Cristalle Bowen, better known as Psalm One. Claybourne and Bowen met at Whiteny Young High School – their friendship has since grown into a business partnership, with Claybourne working as Bowen’s business half.

“It’s very hard for me to look at my art with a business sense. It’s very easy for me to look at other people’s art with a business sense. I used to do marketing for Bacardi. I worked with Levy Restaurants. Larry Levy’s one of my favorite people in the world. Chicago guy. And Marshall Fields, another Chicago staple. So I worked for some really strong brands and I got a sense of what it takes to sell in the market. I also got a sense of what it takes, as far as branding, for you to have something that people can grasp. It’s one thing for you to produce something – let’s say you’re a fine artist and you sell paintings, and you can sell them to your small clientele, and eventually, maybe you’ll become an icon. Maybe. But chances are you won’t, because chances are you’re catering to a very specific niche of people. And having worked for brands that, it’s been their goal to be worldwide, you know – Marshall Fields folded in on itself because of ambition, if you will. These are brands that want to dominate the world, and my friends are at a space in their careers where they’re making really amazing music, really cool stuff that should get out there. I had to ask myself, “How come I haven’t heard this music? I went to high school with him – why didn’t I hear his music?” Ya know? Why didn’t it reach me? Why hasn’t it gotten to the radio?

“So I started looking at that, that angle of it, and then I also started looking at helping translate music in a way that would allow people to receive it.”

I saw a quote on your Facebook page – boy, isn’t that how it always starts…

I would say it does start with Facebook. (Laughs) I know, it’s crazy. But everything starts with Facebook these days.

I went to school for business. I have a business background. I had to make a choice, because I used to be a dancer: am I going to pursue my career as a dancer and have very limited amount of time to dance? Or am I going to do something more practical and go for business. And I chose business. All my friends chose the latter. They chose arts. Every single one of ‘em. And about five years ago, that’s when Facebook was really just popping into the scene. One of my very good friends, Michael Eagle, was in Los Angeles and he was working on a project. He and I started talking about life. “What are you doing?” “I’m managing some businesses. I actually just got an art studio at the Flat Iron. I’m kind of selling some things but I’m also kind of connecting people.”

The Flat Iron building in Wicker Park (photo from (love this picture)

So he and I started catching up, and then he sent me his project, and then I sent him notes on his project, and then he and I started working together and I started turning the business angle towards the art for my friends. Because I realized that while they followed the path of art, they hadn’t necessarily thought about producing products. A lot of them for great reasons. There’s a very strong sense of the artist who says, “It’s art. It’s not business.” So I became the business side for a lot of people, and I’ve had the chance over the last few years to work with some very specific artists. I’ve started some businesses with them, I’ve worked on projects. I really just take what I used to do in Corporate America – and I bring it into the hip-hop world. Because all my friends went into hip-hop.

We all went to Whitney Young, which is a performing arts school. My core group of friends were this underground hip-hop crew called “Paradox.” PDX. And they were the kids that would, like, freestyle in the hallways. (addresses Psalm) You guys would be late for class – (to me) she was part of the crew – they’d be late for class and you’d be like “Where are those guys?” “Oh, they’re in the Blue House freestyling,” or something. That was my core group of friends. But I was also in dance, so I had a whole other group of friends there. And I was in ROTC. I had a group of friends there. (laughter from both) I know, right? And then I was in Future Business Leaders of America, so I had friends there. So people were kind of like, “What is she gonna do?”

I had to pick. I just had to pick, and I chose. I don’t think anyone was like “Oh, she sold out.” I think they were just like “Oh, okay. She’s going into business. That’s cool.”

The reason the choice to go into business was so easy was because it was very difficult for me to choose one specific style of art. One specific discipline. There are days when I wake up and I want to dance, days I wake up and I want to paint, and there are days I want to be a writer, (smiling bigger) and days I want to be a photographer. I’m working on editing video for her, so now I’m like “Yes! I’m a budding filmmaker!”

It’s easy to choose business because with business, you have to go to work and you have to do something. Your boss has to tell you what to do, so you don’t choose, you know? You’re doing it for money. It was a structured path and I went that way. And then I let my art kind of be free. It allowed me to be passionate about it and then also to pursue those passions kind of on a whim, if I wanted to.

When you were choosing business, did you feel at all like something was closing in?

I wasn’t consciously worried about that, but I definitely made a choice. I definitely said, “This is what I’m doing,” and I let everything else go for a while. I was just like, “I’m in business. This is my life.” As I progressed through my career and got, you know, things that you think you’d like to have… I was a general manager of a restaurant and I was like (excited kid voice) “This is great!” But then I started feeling like, “This isn’t so great.”

I started looking at my life and saying “What’s missing?” And I would really like to dance and paint and do all these things. And so I flip-flopped and said, “Okay, goodbye business. Goodbye Corporate America.”

When I started working with Mike Eagle, I started combining my worlds. And I think that’s huge for me. It allows me to transition more and more into the art world. That being said, I still don’t spend that much time on my own art.

This is the beginning of me combining art and business in a healthy way. This is Open Mike Eagle – I started helping him, and then I started working with another guy, Riff Napalm, who’s here in Chicago, and he had a very successful loft party situation. (Laughs) He was running that. It was probably the beginning of the underground loft parties. Mike told me to call this guy, so I called this guy and he says “Yeah, I’m doing these events, and I need help because it’s kind of crazy.” And I basically went in and said “Okay, well we need to structure this like an event series, and we need to make everything legitimate so that we don’t get shut down. I think right now you’re looking at possibly being an LLC…” and just kind of doing that. And long story short, those loft parties, they never last long, but it was a very good run and it spawned the entire loft party culture again in Chicago.

There’s loft parties everywhere these days. Blackgate was the crew of last summer. We don’t know who will be the crew of this summer. Basically what happens is, there are these underground parties, and, well, I guess this is where we start talking about hip-hop probably.

Hip-hop has kind of been edged out of a lot of venues in Chicago, for a lot of different reasons. And so there’s an audience out there that is still very much into the music and into the culture, and as a result they have to find ways to meet. So this guy came up with a way to do that, and he was kind of the pioneer in that, ya know, let’s have parties. Let’s have appearances. Let’s do something that’s different. Let’s be underground again.

The media perception of what hip-hop is is not what hip-hop is. I don’t even know if I can say what hip-hop is, because these are debates. I went to college in the South with a group of Chicagoans who were really big into hip-hop, and they would say “This music isn’t hip-hop. This is rap.” What they were doing in the South. Hip-hop vs. rap. But it’s like, hip-hop didn’t start in Chicago, so is Chicago hip-hop, is that rap? Or is that hip-hop?

Psalm One.

Anyone can be a part of hip-hop. There’s the classic turntables and a microphone. And that’s it. It’s accessible to anyone. How much art is just that accessible? I think it should be celebrated if not for anything else than for its accessibility, because people can make music whether or not they possess the ability to play an instrument or to sing. And I think that’s a blessing. Music soothes the soul. It’s a cure. And the ability to be able to write a song whether you’re good or bad, but just to be able to write a song – you can go to your computer and download an instrumental from iTunes, listen to it, and you can write a rap. And it might be horrible, but that’s something you can do on a whim, today. And I’m not stressing that people do that necessarily (laughs), but you can. And you can’t do that anywhere else.

I used to keep my worlds very separate. They’re starting to melt together because I’m purposefully combining them. I think you have to at this point, or at least in order to be healthy. Part of integrating my worlds means I don’t have to make the move again. The moves have been practical, and sometimes harsh. Impetuous at times. As I’m becoming more mature, and kind of understanding what it is that I want out of life, I realize I want options. What I have to do is create a core that allows me to move around any way I want. And I think that’s through helping people, helping my friends make really great products so they can sell them, so that we can all make money and we can do whatever it is we want to do. They all have a very strong sense of what they want from their music, and I think there’s different ways to translate that to the public. And that’s in licensing, and that’s in creating great packaging, and doing things that are exciting so they can get exposure, creating events, and I think I’m one of the few people who can do all of those things. It gives me a pretty cool ability to move forward in any direction so that I’m always changing without changing everything completely. I don’t have to wake up and say “You know what? I hate this.” Or “You know what? This isn’t going to work anymore.” I can adjust accordingly. If I need to make more money, I have to concentrate a little more “over here.”

When you think about your place in the world, and you think about all of your experiences and all of your skills, and what you quote “bring to the table,” are you thinking about The World? Are you thinking about “My place in hip-hop”? Are you thinking about “My place in art”? Is it all the same?

Oh it’s the world. Definitely the world. By moving through so many worlds, I have an understanding that it’s bigger than this one thing that I’m doing at this exact time. I’m always looking at “Well, how is this going to translate? Can we use this over here?” I work with a group of people who want the freedom to move at will, and that means that you have to think universally, and always be concentrated on the micro and the macro. You have to do your specialty to the best of your ability so that it’s great, so you can take it anywhere you want. Hip-hop will not always take up the majority of my time. In ten years we could be at a film festival. I don’t know. I look forward to where I go, and I’m definitely not limiting it, because why would I?

For the Psalm One PWP interview, click here

For the edit of this interview on Our Urban Times, click here


Check out the first of three concerts in the “Woman at Work: The Parties” summer series at Claybourne’s Flat Iron studio, suite 212. If you don’t know, now ya know.


7 Replies to “People with Passion: business woman Dorothy Claybourne”

  1. Dorothy sounds like a very interesting person with an admirable sense of who she is and how she can enable artists to practice their arts. By doing so, Dorothy is reaching her goal of combining business and the arts. As a facilitator, guiding soul and business woman, she, too, is an artist, creating environments for others to enjoy and learn from. Dorothy is carrying on an old tradition. Check out 15th-16th Century Italy/the Medicis/merchant families that commissioned great works of art by Michaelangelo — or Prince Esterhazy in the 18th Century, patron of Haydn. Jack–Thanks for introducing Dorothy to the public beyond Bucktown./Wicker Park.

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