Feature: StreetWise's Gregg Cole (#7900) on Why He Chose Lincoln Square, What He Has Learned from the Neighborhood, and One Misconception People Have About Him

StreetWise provides Chicagoans in need with “a hand up, not a handout”, so when Gregg Cole (#7900) asked Fleet Feet about our shoes, we felt it was obvious to give Gregg a pair of shoes that can help him continue to spread his vital gregarious personality through the Lincoln Square neighborhood and support him in his journey of living healthily and comfortably.

If you’ve walked down the square on Lincoln Avenue, you’ve heard his voice. Gregg Cole has become a mainstay on the block, positioning himself in between Potbelly and Chase Bank to sell Streetwise, a street magazine sold by people without homes or those at-risk for homelessness in Chicago while helping them achieve personal stability and strength through social services and aiding with employment.

We gave Gregg a pair of Mizuno Wave Sky 4 WAVEKNIT running shoes and talked to him a bit about his time with Streetwise, why he chose Lincoln Square, what he’s learned from the neighborhood and its’ people, how COVID-19 has affected his job, and one misconception people have about him. 

Read the full interview and consider supporting Gregg and Streetwise by donating via Venmo (@streetwise) with Gregg Cole's number (#7900) to donate to him directly.

How are you?

Good. Yea, good.

Talk to me a little about Streetwise. How did you get introduced? How long have you been doing it?

Streetwise. I used to do this in my addiction. When I was addicted to drinking and drugging. What happened was, since I have a background, it’s difficult to get a job. Streetwise doesn’t ask any questions. It doesn’t matter who you are. Anyone can walk up in there. Years ago in my addiction, I sold Streetwise. So I thought about it. I went on a few job interviews and because of my background, it’s hard to get a job. I don’t blame anybody else. It’s the choices I made when I was younger. I drank. I drugged. I made the wrong decisions because it made me feel good at the time. It made me feel a part of something. I lived over in Uptown and there were less fortunate people in Uptown and I saw people doing drugs and I participated in it, and it covered up a lot of emotions. I learned a little a lit bit about a lot of things. I went to school for HVAC but I didn’t know anyone in that field. I couldn’t get a job. At that time I was sober for 4 years and I couldn’t get a job so I went back to drinking and drugging and you know if you don’t use something, you lose it. I still owe a student loan became of it.

So one day I just thought about it. If I could sell Streetwise in my addiction, I could sell Streetwise when I’m sober. So that’s why I started selling Streetwise.

How and why did you choose Lincoln Square and your spot in front of Potbelly and Chase Bank?

When I first started doing this, I worked all over the city. Plus, I knew from when I was in my addiction, at the time, there weren’t a lot of vendors on the north side. I knew a lot of the spots, except this one. So, one day I happened to come over and I stood in front of the bank and about 5 o’clock when people started getting off the L people started saying “I’ll take one”, so I knew someone had been here before. So I said, “hmm, this might be my spot.” We’re supposed to work a spot for 30 days and if no other Streetwise vendor shows up, then it becomes your spot. So I did it for about two weeks and I went to Streetwise and said “hey look, no one else is coming to my spot, I want it to be my spot.” and they said “no problem.” So, this time around when I came back to Streetwise from doing Uber and Lyft, because I put 147,000 miles on a 2017 car, the transmission is slipping, I still owe on it, and it’s about ready to go, so I’m babying it, I actually went to a different spot. Streetwise told me to go back to Lincoln Square so I came back over here and fortunately enough I have a lot of customers I had from before.

I continued to sell here and get to know people and fortunately enough, I am a people person. In the beginning, it was very tough. As you know I’m in the rain, the snow, the sleet. To me, it’s my job. If someone is getting off that L at 5 o’clock in the afternoon they went to work in the morning and they’re coming home. They worked for 8 hours. I feel that I need to show them that I’m going to do the same thing. That’s why I dedicate myself to it and put 40-something hours in it per week.

What do you enjoy about this neighborhood?

The neighborhood is full of very friendly people. I’ve learned a lot here. I’ve learned a lot about family relationships just from watching and having the awareness and seeing how people take their kids out and do things. So much I’ve learned from this neighborhood. Me growing up, my mom and dad did the best they could do. There was a lot of dysfunction in the family and to watch these people who let their kids do what they want to do when it comes to sports and stuff like that and see what their kids’ potentials might be with marital arts over there. The kids, some keep going, some move onto something else. In this area you got the music school, you got the families that are going there and learning instruments. A lot of things that I didn’t do when I was younger. I wanted to be a drummer. I always thought a drummer was fascinating. Everyone liked the guitar but the drummer is doing the work. Why doesn’t he get the credit? But, my mom said, “you’re not going to have a set of those in my house.”

Today, I don’t take life for granted. Right here, [Gregg holds up a photograph on his phone] the one’s that I hurt the most in my addiction was my family. I have a small family, but a beautiful one that I love. We went to Lincoln Park Zoo last weekend. 

Lincoln Square’s a good place. It’s family-oriented. I watch people come and go here. I’ve watched kids grow up to be teenagers. The small stores. The family stores. The way the community looks out for them and shops local and small like that. That’s cool. There’s a lot of unity here. 

Has COVID-19 affected you at all? How?

Actually, in the beginning, it helped out a lot. People in this community showed me a lot of love. I was able to put a few bucks away. In the summer it’s a lot slower for me. A lot of people think that it would be better because there are more people. Summer is a lot slower. Summer is slower because there are more people so people think you’re doing more. People are eating out on the patio. They’re doing a lot more with their families. So, a lot your regulars come by and just say “hi” because they don’t realize. They think you’re doing better. Or, because they have lives of their own so they’re spending a lot more money. You’ve got musicians out on the street. You know, I haven’t made a dollar yet today.

You recently reached out to us and asked us about some shoes. Why?

A few years ago you guys actually helped me out with a pair of shoes and I still remember that and they were very very comfortable and because I stand on my feet so many hours per day my feet have literally cracked the bottom. The shoes that I had were giving me callouses and I still remember to this day how comfortable those shoes were.

What is one misconception people have about you?

First of all, you’re going to have to explain what a misconception is.

Something someone thinks about you that isn’t true.

That’s a hard question. You know, it’s kind of strange. Most people aren’t going to tell you what they think about you. 

The misconception I think people have is that I want to force my issue on someone. I don’t want to force an issue on anybody. I do not want somebody to support me because they feel guilty. A few customers give me $20 on a regular basis and I appreciate it. So much. But I tell them if it starts hurting you, don’t deny yourself for me. You can always stop. You can always go down to where you can afford to support me but don’t hurt yourself for me. 

Is there anything you’d like to tell us since we have a platform?

I’d like to say I’m very fortunate for lincoln square and all of the people. Even in my addiction people were trying to help me. It took till my consequences got so bad that I’ve accepted help and I appreciate their generosity and it’s not taken for granted.

If someone doesn’t carry cash, how can we support Streetwise?

They can support through Venmo. There’s a sign by the tree over there. You can Venmo Streetwise/donations and put my name and number on it. Gregg Cole, #7900. You can buy it online. You can come to me and buy it. 

I like that question.