Debrena Jackson Gandy Talks Scaling Black-Owned Businesses Beyond the Hustle Mentality
On the season premiere of “The Day With Trae,” host Trae Holiday welcomed Debrena Jackson Gandy, co-founder and co-producer of an upcoming eight-week Black business cohort designed to address critical gaps in small business management.
Bridging Gaps in Small Business Ownership
The cohort program was born from Jackson Gandy's extensive experience as a third-generation entrepreneur and her observations while facilitating various business accelerators and incubators. Through reviewing approximately 600 applications for small Black business initiatives, Jackson Gandy identified recurring underdeveloped areas in planning, structure, and mindset.
The eight-week program specifically targets businesses that have been operating for two or more years, moving beyond a "startup" focus to help established entrepreneurs scale their operations. Key areas of instruction include:
Structural Foundations: Moving beyond a "hustle mentality" to implement formal business structures and strategic planning.
Strategic Planning: Practical training on developing four-part strategic business plans and comprehensive marketing strategies.
Financial Literacy: Instruction on revenue plans, understanding profit and loss statements, and managing business finances.
Mindset Shifts: Transitioning from an employee or solopreneur mindset to a business growth mindset focused on working on the business rather than just in it.9
A National and Virtual Expansion
While the program's inaugural year was supported by state grant funding restricted to Washington-based businesses, Jackson Gandy explained a new private sponsorship has allowed the cohort to expand nationally. She noted that the challenges faced by Black-owned businesses are consistent across the U.S., making the virtual format ideal for building a geographic network of entrepreneurs.
"The things that are going on with small businesses here... are the same things going on with the small Black business in Oakland or DC or Atlanta. The dynamics are not that different region to region” she said.
Expert Mentorship and Resources
The program will feature a curated lineup of successful Black business owners and industry experts who provide direct mentorship to the cohort. Guest presenters will range from financial experts, social media influencers, and business owners, including Lewis Rudd, co-founder of Ezell’s Famous Chicken. Participants also receive supplemental resources, such as a physical guidebook from a small business growth expert, to assist in their long-term development.
Holiday emphasized the importance of such programs, noting that approximately 90% of Black business owners are solopreneurs. The cohort aims to provide the necessary network and tools to ensure these businesses are sustainable and no longer rely solely on the efforts of a single person.
The Eight-Week National Black Business Cohort launches Wednesday, March 18, 2026 with partial scholarships available for eligible businesses. To apply or register, click here.
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