Chance the Rapper: From Acid Rap to Star Line — The Making of an Independent Icon #90

In the landmark 90th episode of Go With Elmo, host Elmo Lovano sits down with one of hip hop’s brightest innovators, Chance the Rapper, to decode the journey behind becoming the world’s biggest independent artist. This episode is a masterclass in entrepreneurship, artistic integrity, and the realities of building a career outside the traditional music industry system.

Below, we break down the highlights and key insights from this inspiring conversation.

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About the Guest: Chance the Rapper

Born Chancelor Bennett on Chicago’s South Side, Chance the Rapper (he/him) is much more than a Grammy-winning musician — he is an artist, entrepreneur, activist, and a pioneering force in independent music. With no major label backing, Chance has headlined festivals, hosted Saturday Night Live, won multiple Grammys (including Best Rap Album and Best New Artist), and redefined what it means to be a successful, modern artist and business leader. His latest project, Starline, continues his tradition of ambition and creative independence.

Episode Recap: A Journey in Independent Success

In this episode, Elmo and Chance cover his origin story, the mechanics of running an artist-led business, the vital role of community, and practical advice for today’s artists. Chance opens up about his entrepreneurial influences, the realities of refusing record deals, and his creative process — all while reinforcing the crucial idea that every artist is, at their core, an entrepreneur from day one.

The Nucleus of Artistic Independence

Chance’s story dispels the myth that signing a label deal is the end goal. “Every artist from birth is an independent artist. People think about it as they’re waiting to be signed, but that’s not something you want to wait for,” says Chance. Instead, he frames record deals as tools — not necessities — for artists trying to reach their goals. He goes a step further, rejecting music industry conventions that strip IP creators of ownership and highlighting how exploitative contracts are often built to benefit others more than the artists themselves.

His career embodies this philosophy. Despite early temptations to sign with a major, he chose independence, seeing label requirements — such as mandatory manufacturing budgets for CDs or vinyl — as outdated paywalls that limited access to his core audience, especially those who found his music online for free.

From Chicago Mixtapes to Global Influence

The conversation traces Chance’s rise, starting from his teenage years. By age 18, he had released 10 Day, with earlier high school mixtapes already under his belt. Acid Rap followed at 20, and Chance experienced the slow, organic burn of building a devoted fanbase. Rather than overnight fame, each project became a stepping stone: “Every single small thing I looked at as a major success towards the next thing I was trying to do.”

He credits mentors like Donald Glover (Childish Gambino) and Mac Miller with shaping not just his sound but his understanding of leadership and tour management. Both showed him that surrounding yourself with family and real friends can make a demanding creative life sustainable and joyful.

The Business Mindset: CEO and Founder

Elmo emphasizes the reality that every artist is the CEO of their own business. Chance agrees, but takes it further: “I don’t know if a good CEO does that, but a good owner does… a founder. The owner is allowed to dream and forge the path of that company.” For artists, this means investing all resources — time, relationships, money — into the vision. Chance went “all in” on Coloring Book, even sleeping on studio floors with his family to complete the project.

Financial independence, however, also means constant reinvestment. To support Coloring Book’s release, Chance struck a strategic one-time exclusivity deal with Apple Music, netting $500k without relinquishing any rights or control. He notes, though, that this deal “helped Apple a lot more than [it] helped me,” since it brought a legion of streaming-first fans to the platform.

Collaboration and Community

A recurrent theme is the power of collaboration — both creatively and organizationally. Chance’s band, The Social Experiment, was born from spontaneous connections forged during the making of Acid Rap. The album Surf remains a testament to Chicago’s collaborative spirit, featuring talents like Vic Mensa, Twista, and many others. Even today, Chance tours with friends who were part of his earliest projects.

But collaboration extends beyond other artists — it’s about growing your own team. Chance is proud of nurturing talent within his organization, encouraging people to rise into new roles as the scope of his business expands.

The Realities of DIY Success

Life as an independent artist is never a solo act. Chance’s core team (manager, publicist, lawyer, business manager, tour manager) remains compact but tight-knit. The hustle is constant: touring, orchestrating radio campaigns, and seeking out every opportunity for connection (even street-teaming at malls!) are all part of sustaining relevance and growth.

Being an independent artist also means being keenly aware of your metrics for success. For Chance, these “bullseyes” ranged from performing on SNL and at the Grammys, to supporting Chicago Public Schools through his non-profit, SocialWorks. The structures of major labels can amplify visibility, but he urges artists to set their own goals and benchmarks before entering any deal.

Purpose, Legacy, and Giving Back

Chance sees his projects not just as commercial ventures, but as lasting marks of his life’s purpose. His philanthropic work, especially through SocialWorks, has raised millions for Chicago schools and championed programs in civic education, mental health, arts, and trades. He continues to emphasize the importance of legacy: “When I’m gone, my legacy will be my children, but my purpose while I was living will be the things that I ideated on and executed on.”

Advice for Today’s Artists

Chance closes with advice to aspiring independent artists: define your own goals, be honest about what success means to you, and invest in the “potency of your work” over chasing status. Today’s media landscape is more pay-to-play than ever before; however, authentic work that connects with audiences can still light up the world.

Final Thoughts

This episode of Go With Elmo is essential listening for artists seeking to balance creative fulfillment with business acumen. Chance the Rapper’s blueprint — set your own goals, control your destiny, nurture your community, and never stop investing in your craft — is the new gold standard for true independence in music and beyond.

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Get access to the Go With Elmo Lovano newsletter to get updates on the latest episodes, and insights from music industry experts, pros, and legends on their journeys to making it in music.