Entrepreneur Assistance Program in South Boston Has Big Impact on Downtown Businesses

Last fall, Destination Downtown South Boston (DDSB) was awarded a $100,000 Virginia Business District Resurgence Grant (VBDRG) from the Virginia Department of Housing & Community Development (DHCD) to fund an entrepreneur assistance initiative – Keep Entrepreneurs Program – within the community’s historic commercial district. Over the past year, DDSB delivered high-quality, individualized advising and technical assistance to existing businesses, helping them address financial challenges, adapt to post-pandemic conditions, and explore strategies for growth and expansion. The organization also provided mini-grants to support long-term business success and address building up-fit needs for property owners.

With support from the Town of South Boston and other partners, DDSB initially set a goal to train at least 11 business owners within the historic district, provide targeted grant support to six downtown businesses and/or property owners, and create or retain 10 jobs in the district. Due to the program’s remarkable success, DDSB significantly surpassed these targets—training 21 business owners, supporting 15 businesses through mini-grants, and creating or retaining 23 jobs. Additionally, four building facades were improved, further enhancing the district’s visual appeal and vitality. This marks the organization’s second successful implementation of its Keep Entrepreneurs Program, with results that clearly demonstrate its impact.

Here are a few examples of businesses that were supported by the DDSB Keep Entrepreneurs Program:

Southern Plenty – Leah Long (new owner) utilized funding to install a hood vent system, allowing her to expand menu options and serve dinner in the near future. Leah has been thoughtfully implementing strategic upgrades over time, resulting in significant success for her business.
Distinct Impressions – Owners Rhonda and Harold “Nookie” Green utilized funding to purchase a Digital Heat FX white toner printer. Previously, they were unable to fulfill small, custom orders—such as a single birthday gift or a t-shirt for a 5K event—due to equipment limitations. With this new printer, they can now accommodate these smaller orders. This new printer also enables them to produce items in-house that they previously outsourced, such as wedding koozies or custom mugs, which will help increase the business’s revenue potential.
Shear Happiness – Owner Cissy Martin utilized funding to rebrand her business and launch a new website aimed at increasing visibility and customer engagement. This strategic investment not only refreshed her brand image but also created a strong online presence, positioning her business for growth and attracting a wider customer base.

A standout example of impactful support from DDSB is the assistance provided to Drumlogic Percussion Studio, a space where students of all ages and skill levels can explore and nurture their passion for drumming. Over the years, owner Travis Moore has steadily grown his studio, welcoming an increasing number of students. However, to equip his classes, he has often had to piece together instruments from broken drums, resulting in outdated and heavy equipment that limited the learning experience. Through the Keep Entrepreneurs Program, Drumlogic was able to invest in new, high-quality drums, providing students with the tools they need to fully engage in the art of drumming. This support not only enhances their learning but also ensures that Drumlogic continues to be a vibrant, inspiring business and resource for the community.

“Destination Downtown South Boston felt that it was important to continue to put a large focus on our business retention program in post-pandemic times. We wanted to be sure to invest time and resources to current business’ changing needs or emerging obstacles. We realized that an effective retention program is based on constant communication, and that’s why the organization based this grant program on mentoring the applicants one-on-one (as opposed to group trainings this time) and discussed with them what’s needed to take their business to the next level. What would grow your business? What project would help you thrive? That’s what this grant program is all about.”

– Tamyra Vest, DDSB Executive Director

By providing targeted funding, technical assistance, and personalized advising, DDSB has helped entrepreneurs not only navigate challenges but also thrive in the evolving post-pandemic landscape. This program’s success speaks to the organization’s commitment to sustaining and growing a dynamic, prosperous downtown, making it a place where businesses and the community can flourish together.