Since he began recording himself in 2016, Chicago’s Calboy has followed a hardwon path to stardom. Two mixtapes in 2017 led to a 2018 breakout, a major label deal with RCA, and most importantly, love from his city. Best known for “Envy Me,” the melodic rapper’s heartfelt deliveries power his career. He tells stories from the muck of the trenches of his South Side while also aiming to uplift the listener through his own story of overcoming. Fueled by fans who see themselves in Calboy and are motivated by his hustle, the artist who draws inspiration from Lil Durk has steadily made a name all his own.
Calboy further cemented his role as a staple in the Chicago scene with his celebrated 2019 debut album Wildboy, which featured Durk and other heavy-hitters, and a standout feature on Chance The Rapper’s formal debut album, The Big Day. His most recent co-sign from Lil Wayne on “Miseducation” positions him as a national hot commodity. Even so, Calboy’s main concerns are mental health, his 15 animals, and taking care of his family.
As his star continues to rise, Calboy assures me the key to his continued success lies in staying out of his own way and focusing on creating for the love of creating. “As I accumulated a few dollars, I discovered I’m more interested in things I can do by myself, alone,” he says with a laugh. “Day-to-day with Calboy looks like waking up in the morning, care-taking some animals, calling all my loved ones, making sure they straight. Then, I get my day started with work. It’s been that way forever. I just stay the same and continue to do what I do. That got me to where I am now. I stay out the way and do what I love.”
For Audiomack World, Calboy shares seven lessons learned from breaking into the music industry.
Learning comes with time and experience. “At times, it feels like I still don’t completely understand [the music industry]. You never completely understand it because there’s different individuals and personalities that come with business. You gotta be a person that’s level-headed. When I got a little older—I signed a deal at 18, now I’m 22—I feel like I understand much, much better. That comes with wisdom.”
Don’t trust everybody you meet. “The first mistake I made was believing everybody was for me. Being a trusting person… Man! There’s sharks out here, real-life snakes in the grass. Some people look at you as a dollar sign. They don’t necessarily care. Even though people might put a little energy into making your situation pop, they always got their motives.
“That was the biggest mistake: trusting everybody too fast. It’s a business at the end of the day. Everybody needs to go home with full pockets and happy. If that doesn’t happen, there may be slips and cracks.”
A team is built over time. “The bad leaves fall off the branches on they own. You don’t have to kick anybody to the curb because it all presents itself in the end. Just keep working, don’t get discouraged, and [see] who with you, around you, and believe in what’s going on. In due time, you see who the greedy one is, who the day one is. It’s just staying alert.”
Use social media to your advantage. “When I was going through [‘Envy Me’ popping off], I wasn’t even trying to capitalize. I was so stuck in the moment. It was everything I worked for! I was looking at my homies like, ‘Yo! You see them screaming my name? They singing the song word-for-word.’
“But, an artist, at that [viral] moment, [you] should be capitalizing. Your social media is your best friend. Match your face with the material that’s viral. Get out of your comfort zone a little bit. Show everybody you. We live in an era where you can show the entire world what you got going on, so tap into that era we in.”
Fame should be fun but remember the business. “Fame does not stress me out. It’s more the technical situations that stress me, the people that stress me out. When you an artist on the rise, you having fun and doing what you love. You believe, deep down in your heart, this is what’s gon’ put your family in a better position. But nine times out of 10, you’re not thinking about the business. That’s the stressful situation. New partnerships, new deals, new people, and not knowing everything. That’s the stressful part.”
Mental health is everything. “In this field, you gotta take good care of your mental health. I come from a few mental illnesses, and I don’t deal with those things anymore. I might have my moments, but at the end of the day, my mental is strong because I built it that way. I forced myself to keep pushing and keep going. It’s a lot of negativity that comes with the music industry as well. If you don’t have a strong mental, that could potentially break you down.”
Don’t let the industry change you. “I’m big on strong mental health, on self, on taking care of that and being strong up top. Can’t nobody in this world make me bitter.”