WDB L.E.G.A.C.Y. Weekend Celebrates 20 Years of Empowering Black-Owned Businesses

Keeana and James
Keeana and James

WDB L.E.G.A.C.Y. Weekend Celebrates 20 Years of Empowering Black-Owned Businesses 

 

WDB Cares Non-Profit Continues to Provide a Platform for Young Entrepreneurs


CHICAGO, January 21, 2026 — WDB Marketing and its nonprofit division, WDB Cares, will celebrate a historic milestone in 2026: 20 years of WDB Marketing and 10 years of the L.E.G.A.C.Y. Awards platform—two decades of building brands and a decade of building legacy through entrepreneurship and community impact. Since its inception, the L.E.G.A.C.Y. platform has awarded over $250,000 in cash and prizes to young and emerging entrepreneurs, fueling business growth, job creation, and generational wealth across the region.

The three-day celebration, rooted in Leadership, Education, Growth, Advocacy, Community, and Youth, will bring together more than 1,000 entrepreneurs, corporate partners, and community leaders for a weekend of recognition, education, and collaboration. The weekend will culminate in a prestigious awards gala honoring outstanding business leaders whose work continues to strengthen and uplift their communities.

Key Events:


Friday, March 13th: L.E.G.A.C.Y. Talk Business Mixer 

It will be an evening of meaningful connection and inspiring conversation among visionaries, innovators, and change-makers — a refined kickoff to an empowering weekend. This exclusive event promises to be an unforgettable experience, bringing together distinguished guests, esteemed panelists, and the honorees of the WDB L.E.G.A.C.Y. Awards. Attendees will also enjoy a vibrant showcase of diverse businesses, fostering an enriching environment for networking, collaboration, and inspiration.


Saturday, March 14th: 10th WDB L.E.G.A.C.Y. Awards Gala

433 W. Van Buren St, Chicago, IL

6:00 PM until 10:00 PM

The annual L.E.G.A.C.Y. Awards Gala will proudly showcase a vibrant selection of fifteen Black-owned restaurants while honoring the outstanding recipients of the 2026 WDB L.E.G.A.C.Y. Awards, recognizing their remarkable contributions to the business community. This year’s distinguished honorees include legendary entrepreneur Robert Townsend, celebrated for his groundbreaking impact in entertainment; trailblazing leader Stephanie Hart, whose leadership continues to inspire; and Lavelle Sykes, recognized for his commitment to empowering entrepreneurs and building pathways to success.

Among the highlights of the evening will be the presentation of the WDB Cares Young Entrepreneur of the Year Awards, where emerging business leaders will receive $25,000 in cash and prizes, including $5,000 in direct funding and $10,000+ in professional services such as accounting, legal, and marketing support. This signature pitch competition reflects WDB Cares’ commitment to investing in the next generation of leaders and turning bold ideas into sustainable, successful businesses.

2026 L.E.G.A.C.Y. Awards Black Restaurant Showcase

This experience celebrates Black excellence in the culinary space while connecting your brand directly with new clientele and consumers throughout the Chicagoland area. (Over 20 of restaurants will be featured, including The Soul Food Lounge, Nicole Jordan Catering, Flossmoor Social and Brown Sugar Bakery)


Sunday, March 15th: L.E.G.A.C.Y. Brunch Takeover Brunch

12:00 PM to 4:00 PM


The weekend will conclude with a powerful Sunday Brunch experience bringing together great food, great music, and meaningful connections. This signature gathering creates space for entrepreneurs to reflect, recharge, and build relationships while enjoying a special Legacy Talk from a respected business leader offering powerful insights and inspiration as the weekend comes to a memorable close.


About WDB Cares NFP

WDB Cares is a mission-driven nonprofit organization dedicated to supporting businesses in building generational impact through economic empowerment, access to capital, and strategic support. Its signature 20 for 20 Young Entrepreneur Program provides 20 emerging entrepreneurs under 30 with $5,000 in direct capital, $15,000+ in professional services, an eight-week accelerator, and ongoing mentorship. In addition, WDB Cares offers accessible grant funding and targeted business education focused on marketing, financial management, access to capital, and scaling strategies—connecting entrepreneurs to partners and platforms that fuel sustainable community growth.

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