CHICAGO-Chicago’s Indigenous business community convened this week for a two-day series of events that did more than celebrate achievement and excellence. The Legacy Talks Business Mixer and the Legacy Awards & Gala created space for reflection, strategy, and intergenerational alignment across industries.
At Legacy Talks Business Mixer, Chicago Entrepreneurs Share Lessons in Leadership
The weekend opened with the Legacy Talks Business Mixer, featuring the Business Legacy Panel. Hosted by journalist Tia Ewing and entrepreneur Early Walker, the discussion brought together established leaders who have built institutions that extend beyond profit margins into cultural impact.
Panelists included Resa Luster-Mac of Luster Products; Myiti Sengstacke of Chicago Defender Charities; Melody Winston of Living Fresh Market; and Charmaine Rickette of Uncle Remus Chicken.
Their conversation centered on sustainability and not just simply maintaining a business, but preserving influence across decades. Speakers reflected on access to capital, financial literacy, brand evolution, and the discipline required to build enterprises that withstand economic shifts and generational transitions.
Key takeaways from the panel included:
- Never give up. Even after a setback, show up the next day and keep going.
- Respect both the visionary and the person who laid the groundwork.
- Know your numbers and understand the fundamentals of your business’s finances.
- Avoid taking things personally. Stay calm and never react emotionally.
- Prioritize what is best for the business, even when others may not understand your decisions.
- Invest in your team and encourage them to invest in the business as well.
- Avoid trying to build alone. Form a strong team or collaborate, even across industries.
A Night of Legacy: Chicago Honors Trailblazers at Annual Awards and Gala
The evening transitioned into structured networking, where emerging founders and seasoned executives connected over shared strategy rather than surface-level introductions. The mixer also recognized Keena and James for 20 years of success with WDB Marketing and a decade of producing legacy-focused programming, a testament to what consistency and vision can yield over time. I’m very much always in support of anything WDB does.
The following evening, the Legacy Awards & Gala expanded the celebration into a formal showcase of impact. The event featured a curated restaurant experience, live performances and award presentations honoring leaders whose work has shaped Chicago’s entrepreneurial and cultural landscape.
This year’s honorees included filmmaker Robert Townsend; Stephanie Hart of Brown Sugar Bakery; Dr. Pamela Blackman of the BBF Center for the Arts; Jimmy Akintonde of Ujamaa Construction; Lisa McKay of the Culinary Education Academy; Pamela Robinson of the 40+ Double Dutch Club; and Gus Rickette Sr. of Uncle Remus Chicken.
Michelle Releford of NBC 5 and Marseil Jackson of The Drea Center served as hosts. Special guests included Mayor Brandon Johnson, Event Chair Charles Smith and Pastor Jerome Glenn of New Life Covenant Southeast.
Entertainment throughout the evening blended music, dance and spoken word, featuring performances by Venard Live, Slique Jay Adams, Simone Green, Windy Indie, Prince Adrean and Company, Martin Woods and the HBCU Gospel Alumni Choir, Azania Drum, Team Jukeboxx Mas Band and poet K Love The Poet. DJs Sean Mac, Bsyde and Bamm closed the evening with an after-party that carried the celebration forward.
Across both nights, a common theme emerged: legacy is not accidental. It is engineered.
In a city where “Black” entrepreneurship has historically operated on the margins of institutional support, gatherings like this underscore a critical shift: ownership is being preserved, narratives are being controlled, and ecosystems are being built with intention.
The events did not simply honor individual achievement. It reinforced a blueprint: disciplined leadership, collaborative economics, and cultural stewardship remain central to sustaining Chicago’s future as an Indigenous business hub.
Legacy, as demonstrated over these two evenings, is not just a nostalgic concept, but it is an active strategy. Today I didn’t attend the brunch, but next year I will. The weekend gave what it needed to give, which was a lot of inspiration and motivation to continue the entrepreneurial journey.
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