Building Anyway: A Reflection on Black Entrepreneurship in Chicago

Black entrepreneurship has never just been about owning a business.

It’s been about building despite the barriers that were built to hold us back.

Building when capital was scarce.

Building when systems weren’t designed with us in mind.

Building institutions when access wasn’t offered.

Black History Month always invites a time of reflection. As a founder in this city, I think about how Chicago holds a long tradition of Black founders who didn’t just create companies — they created infrastructure.

When I think about leaders like Madam C.J. Walker, Anthony Overton, and John H. Johnson, what stands out isn’t just their success — it’s their strategy.

Madam C.J. Walker built from lived experience. She understood her customer because she was her customer. She didn’t wait for validation. She built distribution. She built ownership. And she created opportunities for other Black women in the process.

Anthony Overton understood something equally powerful — businesses generate revenue, but institutions generate stability. A cosmetics company, a bank, an insurance company, a newspaper. That wasn’t accidental — that was ecosystem thinking before we had language for it.

John H. Johnson understood narrative as economic power. Through Ebony and Jet, he shifted how Black life was represented nationally. He didn’t just publish magazines — he expanded imagination.

And that thread still runs through Chicago today.

Leaders like Mellody Hobson continue that legacy by pushing conversations about capital access, ownership, and representation in rooms where those decisions shape markets. The work evolves, but the throughline remains: access matters. Ownership matters. Who controls capital and narrative matters.

At The Gray Matter Experience, we see that same instinct in our young people.

They are building brands, testing products, and learning how to price, pitch, and protect their ideas.

They are thinking about ownership earlier.

They are asking better questions about capital — and they are not waiting for permission to start.

-Britney Robbins, CEO & Founder