Keep Entrepreneurs Program Application

Destination Downtown South Boston’s Keep Entrepreneurs Program helps retain and strengthen downtown businesses by providing education, mentoring, and resources that support sustainable growth. The program focuses on identifying business gaps and offering customized guidance, tools, and access to services and financing.

Due to the program’s positive impact and continued demand, funding has been secured again to support this initiative. Award amounts will vary based on project scope, demonstrated need, and available funding.

Grant Activities

Applications are reviewed by the Grants Committee, with selected businesses interviewed and visited on-site. Awards are based on a project’s ability to strengthen the business and support growth.

Eligibility

Applicants must be existing or expanding businesses in the Main Street District. Business retention is the program’s primary goal. This is a competitive process, and applicants must clearly outline goals, strategies, and expected economic impact.

Eligible Uses

Grant funds may support e-commerce, social media, professional services, entrepreneurial support, or building up-fits. Projects must demonstrate how the funding will increase sales and contribute to a stronger, more cohesive downtown.

Complete and submit the application below by the deadline to be considered.

Keep Entrepreneurs Program Application Please answer all required questions below to apply for Destination Downtown South Boston’s Keep Entrepreneurs Program. Deadline to apply is February 15, 2026. Contact Tamyra Vest with questions (tvest@southboston.com).

BUSINESS NAME(Required)

Name(Required)

First Last

BUSINESS ADDRESS(Required)

Street Address Address Line 2 City State / Province / Region ZIP / Postal Code

MAILING ADDRESS (IF DIFFERENT FROM BUSINESS ADDRESS)

Street Address Address Line 2 City State / Province / Region ZIP / Postal Code

EMAIL(Required)

PHONE(Required)

GOALS

What are your short- (12-months) and long-term (five years) goals for your business?

SHORT TERM GOALS(Required)

LONG TERM GOALS(Required)

BUSINESS CHALLENGES

Expert Assistance: Are there any challenges to your business that you would like to address through this program? Are there any opportunities that you would like to take advantage of? What do you wish you could do better? What do you wish you could learn? EXPLAIN BELOW(Required)

PROJECTS/INITIATIVES

Do you have an initiative or project in mind already that you would like to have funded by a SoBo KEP grant? EXPLAIN BELOW.

Tell us about your targeted customer(s)? Where do they live, what are their age ranges, what is their approx. household income, what are they spending money on, what social media & other media channels do they interact with? This might be information you have in a business or marketing plan or a component of your marketing strategy.(Required)

SOCIAL MEDIA

Website

Facebook

Other Social Media

TRAINING, EXPERIENCE, OTHER

Please share any classes, trainings, workshops, webinars that you have participated in during the last three years to grow your skills as a business owner.(Required)

FINANCIAL AND PLANNING

Cost(Required)

What is the estimated cost of your project, initiative, or campaign?

Do you have any plans, drawings, and estimates that support your grant request?(Required)

Yes

If available now, please upload these documents.

Max. file size: 128 MB.

Why do you believe this proposed project will help make your business stronger and/or poised for expansion or growth? Explain how the proposed project will take your business to the next level.(Required)

How will this help you reach your target customers?(Required)

Please estimate your timeline for completion of your project.(Required)

If you were selected to receive a grant, how would you prefer to receive your funds?(Required)

Please choose ONE.

I would like to submit invoices to DDSB for direct payment.

I would like a grant check mailed to my mailing address.

I would like to pick up a check at the DDSB office.