In this episode, we unpack how small business ownership represents both hope and hardship in Black Chicago’s economic landscape. Through the voices of Charisse Bennett, Akilah McCord, Marquinn McDonald, Chris Davis, and others, we explore the impossible calculations entrepreneurs face, the ripple effects on nonprofits and service providers, and the unique community spaces—like barbershops—that anchor neighborhoods. From federal pressure and debates on immigration to grassroots block clubs and the struggle against gentrification in Bronzeville, this episode reveals how survival, resistance, and innovation come together in a city at the crossroads of crisis and possibility.

Sources and Methodology: This investigation is based on original interviews conducted in September 2025 with Chicago residents, community organizers, nonprofit executives, and small business owners. Additional reporting drew from Chicago city budget documents, Illinois state employment reports, federal Community Violence Intervention funding allocations, Cook County housing data, and real estate market analysis. Some sources requested anonymity due to employment restrictions or safety concerns.

Primary Interviews: Marquinn McDonald (WatchGuard Chicago), Akilah McCord (The Answer Inc.), Chris Davis (educator/entrepreneur), Charisse Bennett (small business owner), and additional community members.

Malachi Webster is a freelance producer and writer covering community organizing, economic development, and social justice in Chicago.

*This work was made possible in part by funding from the Alliance Matters campaign, an initiative of Chicago Independent Media Alliance (CIMA) and the Field Foundation.

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