What are you usually drinking on a morning like today?

This is a ginger tea. I’m trying to stay well right now!

You have said your purpose is higher than just saying you’re from Chicago, that you’re here to make a change. The Common Ground Foundation empowers the city’s underprivileged youth to become leaders. What do you remember most about yourself at a young age?

I remember loving basketball. I remember wanting to be cool. [Laughs] I remember loving hip-hop music and being really inspired at that age by Run-D.M.C., LL Cool J and Michael Jackson. I remember really wanting to be noticed. I think in certain ways performers or entertainers are always wanting to be noticed in some way or another.

What is a mantra you wish you would have always lived by?

[Donda’s House Creative Director] Rhymefest told the story of how [Kanye West’s mother] Donda West asked him, “Is that your truth? You need to speak your truth.” I wish I would have known to always speak my truth. And that the world was big, it wasn’t just about proving something to my friends. I wish I would have known to truly appreciate who I am and to not be afraid, those would have been my biggest lessons.

When have you felt like you didn’t speak your truth? 

Oh man, there was a moment in ’95 or ’96 when I did a song that the label had wanted me to do. At the time there were big hip-hop artists out there like Biggie and Nas so the label was like, “You need a big record,” so I tried to cook something up in vain to be on the radio.

And the outcome didn’t feel true to you?

It was still me but it just didn’t come from that pure truthful place. I think there were a lot of times in my life when I didn’t speak up and say, “Hey! No, you can not do that to me.” It’s about setting boundaries and saying, “This is how I feel about this situation,” because being able to express yourself is like a jewel. It’s a jewel that you carry with you and it feeds your mental wellness and your health. It’s never good if you hold stuff in.

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You’re teaming up with Kanye West’s Donda’s House to produce Chicago’s first Aahh! Fest. How old were you when you first met Kanye?

He was only 19 at the time and I was probably 23. I first met Kanye through No I.D., his mom and Kanye’s mom were teachers at the same school. At that same time Kanye was making beats and rapping so he would come around. He was the young hungry dude and wanted to challenge me in rap ’cause I was from the city. So I remember I came out and did my thing from the city!

Is creativity something you can plan

It comes at spontaneous times. I’ll say, “I’m about to go write right now,” and sometimes it will just flow. Other times I can sit there and write for four hours and only come up with one line. It really is a divine expression. It’s a flow, a current that you have to be open to and you will know when it’s coming out in a pure way. You just have to be in that space and if you’re feelin’ it and you know that it’s coming through in that truthful way then that’s when it’s good. If you’re sittin’ there bangin’ your head against the wall, that’s when you need to step away sometimes. I usually step away a lot but this time [with my new record] I was just ridin’ the ride.

Do you ever feel fearful?

Oh yeah, I have gotten scared before but then I remember that there is no need to be fearful. If you really are passionate and love what you’re doing and you believe that you have worked towards greatness for it and within it, then there is nothing to be afraid of. You’re going to win a lot of ’em and you’re gonna lose some but in the losses you gain something and you can learn something.

You exude confidence. When was the last time you felt insecure?

The first time I got an acting role. In the audition they had told my agent that I was green and they didn’t know if I could do it. I was like, “I’m gonna show these f-ckers what it is,” and it just so happened to be a project that I was passionate about too so I went in and gave ’em my all. I got the role and that was my first role and the first call back I had ever gotten. I’m the type of person that if I know I have worked at it then I feel confident.

Is there an aspect of your career that didn’t come easily?

I was doing speaking engagements years ago and I was trying to just go up and speak off the cuff and I wasn’t great at first. Then I started working on it and I got better. I’m still striving for greatness but the point is I have come across nervousness and fears in my past but this year is all about no fear! Now I don’t even allow myself to think with fear.

Common Ground Foundation
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What was your very first job?

My first job was at the city, I was doing janitorial work at a school and helping with whatever they needed. I was a do-it-all guy at the school for their summer program. That first paycheck made me feel like I had earned something and I had some worth, not just because it was money but because I had put some effort into it and I earned it. It gave me a certain value that I appreciated. I knew that wasn’t going to be my job in the future but it still felt good being able to work and have my own money to enjoy myself and do things.

What would you spend your money on as a teenager?

Man, jeans and gym shoes and CDs!

If you could have a drink with anyone, who would it be?

It would probably be Lupita Nyong’o.

She’s gorgeous.

Yeah, I really like her. She’s just got somethin’ about her that I like! I like that style and I feel like even though she’s very distinguished, I think that once you get her drinking… I like seeing people that you wouldn’t think let loose. Like me, I get loose when I drink!


Yeah! A little sangria?

White or red?

Red! I’ve got a friend named Santay who makes great sangria. I love it.

It’s good but it can do some damage.

I know! I love it because it sneaks up on you! You’ll be drinkin’ it like it’s Kool-Aid and then you’ll be drunk!

Common Ground FoundationCommon Ground FoundationCommonKIRSTEN MICCOLI / A DRINK WITH

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