“Hustle, period.” 

This is the mindset of entrepreneur and Chicago music legend John Monopoly. Nowadays, John Monopoly has his hand in a wide array of business ventures. He is the chief strategy officer for cannabis brand Village. He’s on the advisory board for gaming platform Gamelancer. He is executive producing a drama series about the Chicago drill music scene. And of course, he still has his ear to the streets in search of untapped musicians and creatives.

John Monopoly has a ton of new business opportunities to handle. But earlier this week, he also decided to get a bit nostalgic and tap back into one of his earliest ventures, Hustle. Hustle was his and Don C’s management company founded in 1998. Along with promoting big events in the Chicago nightlife scene, Hustle would also act as the management group for the Go Getters, a rap group that included Kanye West, GLC, Timmy G, and Arrowstar. Monopoly would go on to co-manage West during the early years of his career before the two mutually parted ways in 2008. While he says the two are currently not working together officially, Monopoly has assisted Kanye on and off with consulting and other duties over the past couple of years.

To help promote the Hustle brand in the late ‘90s, Monopoly created a series of graphic T-shirts that featured the Hustle logo across the chest and “It’s Almost Over” written on the back, a phrase Monopoly says was used as a nod to Jay-Z’s introduction on the track “Jigga My N****.” Now, over two decades later, Monopoly is re-releasing the T-shirts for the first time. While the legacy item that is currently available for $80 will act as a soft introduction to the brand, he hints at new items like White Sox fitted caps and a hoodie collaboration with Jerry Lorenzo’s Fear of God.

“Through my years of working with Kanye and Virgil, Don, Jerry, and our whole crew, I just felt like the time was right,” Monopoly tells Complex. “These last couple of years I had reconnected with Ye. We did a bunch of stuff together and I guess I was feeling a little nostalgic.”

Ahead of the Hustle relaunch, we got a chance to chat with Monopoly about why now felt like the right time to bring back Hustle, future plans for the brand, the Chicago fashion scene, and more. 

(This interview has been edited and condensed for clarity.)