Growing up, your hometown can feel simultaneously like the center of the universe and a far-flung, middle-of-nowhere satellite. No one knows this dichotomy like Cole Bennett. Growing up in the Illinois suburb of Plano, Cole admired the explosion of drill and rap musical acts in neighboring Chicago, but he often felt like an outsider looking in. Soon enough, he and his family moved to Chicago, which got him closer to the culture being created in the city, musically and beyond.

When Cole founded Lyrical Lemonade in high school, he focused his coverage on local show recaps and freestyle battles; similarly, his first documentaries were about the Chicago music scene. Eventually, local artists caught wind of this taste-making high schooler and started to hit him up for music video work. Over the years, Cole’s co-sign became synonymous with future stardom for many up-and-coming artists.

Cole’s music video work is high-energy and animated. There are nostalgic references to old-school video games and action movies, all shot through a frenetic, playful lens. The energy is palpable, and the results often touch a nerve for younger listeners and viewers. Most of Cole’s work zooms past the million-view mark within 24 hours of uploading; some have become popular memes.

As Lyrical Lemonade grew, Cole was tempted to leave Chicago for L.A. or NYC. Instead, he doubled down on Chicago and expanded the team to include people like Jake “Jaydot” Brode, the content director who works across Lyrical Lemonade’s website, events, merchandise and more. At the same time, artists from outside the city began flying to Cole for videos and features.

As an Illinois native who grew up loving sneakers, Cole was excited to put Lyrical Lemonade’s mark on a Jordan Aerospace 720, hoodie and long-sleeve T-shirt for the Jordan Chicago Collaborators’ Collection. He and Jake were inspired by the city’s Pink line, as well as the train’s unique ability to connect Chicagoans. Below, Cole and Jake talk about their origins and working on the collection.

How did you guys meet and start Lyrical Lemonade?

Jake: We met at South by Southwest (SXSW) a few years ago. We threw a show together and had some mutual friends. After that, we had a good working relationship.

Cole: I knew that I wanted to bring a Lyrical Lemonade show to SXSW, so I was like, “We should do something together.” We locked it in, and I noticed that he was really good with graphics. I started to have him do flyers for Lyrical Lemonade shows. I also noticed that he excelled in areas beyond art. He’d come back and forth from where he lived, in Kalamazoo, which is three hours away. One day, I was like, “Do you want to come work with Lyrical Lemonade and move out to Chicago?” It’s been history since then.

What was the inspiration behind your contribution to the Jordan Chicago Collaborators’ Collection?

Cole: We wanted to pull something together that was colorful but also fit our brand and what we do. We both grew up wearing Jordans. As soon as we knew that we had this opportunity, we ran with it.

Jake: The palette goes with a lot of our merchandise and branding, so it was a really easy mix. We pride ourselves on attention to detail. We wanted the shoe to show that, as well, through the reflective material, suede and more.

“There are a lot of emotions that go along with the train lines. You can build relationships and friendships.”

What was it like when you saw the final products come back?

Jake: It was crazy. For me, designing a shoe with Jordan Brand was a lifelong dream. I was just thankful to be in this position.

Cole: It was definitely crazy. Growing up, wearing Jordans and being such a huge fan of the brand, it was surreal to look at, hold and feel. It really all came to life.

In your opinion, how do the train lines in Chicago bring the city together?

Cole: They bring the city together in a very literal way, because there are a lot of meeting points where you hop from train to train — where people meet to go from one stop to the next. It also brings people together in ways you wouldn’t believe. I actually met people on the train, on my way to class and otherwise. You sit next to someone, and you start a conversation. You get to see all different walks of life.

There are a lot of emotions that go along with the train lines. You can build relationships and friendships. It opens your eyes to things you may not have seen before.

Jake: I’m actually from Michigan, and now I reside in Chicago. For me, when I first moved here, the train was an easy way to get to know the city better. It’s a thing that you hear about as an outsider coming into the city. There’s a community aspect, but it also helps to familiarize yourself with all that’s going on.

Cole, you’ve spoken about how it was important for you to avoid the temptation of moving to other cities, because you care about Chicago and its talent. Why is that still important to you?

Cole: Chicago has done so much for me in so many different ways. It’s given me so many opportunities. The people I’ve met, the relationships I’ve built — I owe it all to Chicago. Staying here is my way of showing appreciation for the city. People can hold onto Lyrical Lemonade and wear it on their back like a team jersey. I want that to be one of Chicago’s teams.

People love to say L.A. and New York City are the places you need to be in order to take your business to the next level. In a lot of ways, they’re right; there are so many resources there. But Chicago has resources, too. You just have to dig a little deeper to find them, and if you can’t find them, you have to create them. I like the thrill of that.

Cole, your mom famously helped you come up with the Lyrical Lemonade name. What’s been her reaction to seeing it blow up?

Cole: My mom gets this look on her face, where it looks like she’s crying, but she’s also smiling a little bit. It’s her way of showing me that she’s proud. Whenever I get to see that expression, I know I’m doing something right. I’m so proud, and I like to involve my mom whenever I can. I bring her to all the shows and make sure she’s up to date with everything. She gets to feel it growing as much as I do.

This collaboration is great, because I used to come home and tell my mom about the new Jordans I wanted. Or we would go to the mall, and I’d try to convince her to buy me a new pair of shoes. To see that carton [logo] on an Air Jordan shoe is an unreal feeling.

Jake, how did you start designing?

Jake: I’ve been a designer for a long time, ever since high school, when I took an Intro to Photoshop class. I just really liked it. After high school, I was trying to get into the music industry, and a lot of people who I met needed cover art. So I was just doing that. Then, I started to manage some artists, and they couldn’t get booked for any shows. We were throwing our own shows, and I was doing the flyer art for them, as well.

All of these different experiences were examples of me throwing stuff at a wall and seeing what stuck. The constants were design, illustration and doing art. Through all of that I knew that design is what I really want to do. When Cole and I met, it was perfect timing for me to take things to the next level.

How do you guys see these various aspects of basketball and music culture uniting people?

Jake: It’s crazy how much synergy there is, especially with music, basketball and fashion. In the beginning, I was hooked on reading sneaker and hip-hop blogs every day. I was introduced to so many things that I couldn’t access otherwise. I’ve met some of my best friends through events full of like-minded people.

Cole: I feel like all of these things are subcultures underneath one umbrella. They’re all intertwined in one way or another, from a basketball standpoint. They just bleed together. It’s all the same. It’s the same fuse and wiring. I never played basketball, but I always loved basketball. I couldn’t always get all the sneakers I wanted, but I could appreciate them, and it was my way of connecting from a distance.

With music, I’ve been a huge fan of hip-hop for my whole life. Listening to it, reading magazines and going on the Internet has all been a part of it. You could feel it without being in the industry. I was 10 years old, but I could still feel the power of what it was. It all meshed together for me.

What is your message to Chicago?

Cole: I would say, “Thank you for showing me the way but not handing me anything.” I really had to learn everything that I’ve been taught. Nothing was handed to me. I had to eat dirt for a while and go through the system of things, in terms of how the city works, without having any opportunities presented to me.

Jake: I’d say, “Thank you for putting me in a position to make my own reality.” I feel like our generation in Chicago really did that, because we had to go through trials and tribulations. Nothing was handed to us. I am always willing to open my hand to the next person. I’ve seen so many people do that, too. It’s a beautiful thing.

The full Jordan Chicago Collaborators’ Collection releases globally starting February 15.

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