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



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

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 The DuSable Black History Museum and Education Center 6:00 PM until 10:30 PM Guests will also experience a vibrant showcase of diverse businesses, creating an energizing atmosphere for networking, collaboration, and strategic partnership-building. The evening’s theme centers on creating and sustaining legacy in business — exploring what it truly takes to build institutions that outlive trends, leadership transitions, and even generations. Through an engaging and thought-provoking panel discussion,

second- and multi-generational business leaders will share insights on longevity, succession, stewardship, and preserving vision while evolving with the times. Featured panelists include Uncle Remus – Charmaine Rickette, Luster Hair Care – Theresa Luster, Bud Billiken Parade/Chicago Defender Charities – Myiti Sengstacke-Rice and Living Fresh Market – Melody Winston

Saturday, March 14th: 10th WDB L.E.G.A.C.Y. Awards Gala 433 W. Van Buren St, Chicago, IL 6:00 PM until 12 AM The annual L.E.G.A.C.Y. Awards Gala will proudly feature a vibrant culinary experience highlighting fifteen Black-owned restaurants, while honoring the distinguished recipients of the 2026 WDB L.E.G.A.C.Y. Awards for their exceptional contributions to business, leadership, and community impact. This year’s esteemed honorees include legendary entrepreneur Robert Townsend, recognized for his groundbreaking influence in entertainment; Stephanie Hart, honored for her powerful advocacy and inspiring leadership; and Jimmy Akintonde, celebrated for his dedication to empowering entrepreneurs and creating pathways to economic success. Additional honorees include Lisa McKay for Education, Pam Blackman for Advocacy, Pamela Robinson for Community Impact, and Gus Rickett Sr. for Family Legacy — each recognized for their lasting contributions and commitment to strengthening communities and future generations. 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) Chef Nicole Jordan, Flossmoor Social, The Soul Food Lounge, Shawn Michelle's Ice Cream, Lexington Betty Smokehouse and many more.

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

Kitchen + Kocktails by Kevin Kelley, 339 N Dearborn St, Chicago, IL 60654 12:00 PM until 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.

Event Website: www.legacyawardsweekend.com

Event Video: https://www.youtube.com/watch?v=aoqyiJa_AmQ

WDB Cares Video: https://www.youtube.com/watch?v=VQu6yhZnCoU&t=113s

Key Photos: https://drive.google.com/drive/folders/1GOzlLekayIOYwLqGQJgYW3SrF8mo2hI-?usp=sharing

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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