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Aspire to Entrepreneurship

DSLBD operates annual programming grants and provides direct support to returning citizen-led small businesses and entrepreneurs. Aspire to Entrepreneurship started in 2016 at the request of Mayor Bowser as a pilot incubator program, and has grown to be an annual grant process to build the entrepreneurship ecosystem supporting justice-involved residents who are pursuing wealth-building through small business creation and growth. Residents re-entering from incarceration face unique challenges to employment; launching your own business can be empowering and liberating. 

Support for your business idea

Once a year, DSLBD runs a particular program to meet the needs of returning citizens.

If you are a justice-involved resident with a business idea or currently operating business, we also provide direct services, whether or not you participate in WeAspire cohort. We offer one-on-one resource navigation for Aspire on Mondays by appointment. Those who do not enter into a grant-funded program Aspire program are still eligible for free and ongoing, one-on-one direct technical assistance. Please contact Caroline Howe at [email protected].

Supporting WeAspire

Aspire is based in the idea that entrepreneurship is for everyone, and everyone benefits from community and support. 

All of these programs have benefited from partnerships with community organizations and individual mentors. If you are interested in volunteering or working with Aspire to provide services, please reach out to If you are a community volunteer or interested party or partner, please contact us to find out how to be involved in related trainings and meetings, connect with our partners, invest in or buy from Aspire graduates' businesses, learn more about the initiative, or become a business mentor. Please contact Kate Mereand at [email protected] with subject line, “Supporting WeAspire” 

Core Program Description

The core Aspire to Entrepreneurship program has adapted as over 60 Aspirants have graduated from intensive business training with specific, trauma-aware wrap around services in the past four years. The grant funded We*Aspire programming continues to build training for new businesses and support for alumni with competitive grants to further build the businesses. As alumni explore the entrepreneurial ecosystem, they have the option of staying connected with wrap around services. Our key metric is around Aspirant well-being to maintain a low recidivism rate which helps to keep families and communities in tact.

Programming in past years has included 4 cohorts of six-month intensive incubators, a new nights & weekends training through Aspire Side Hustle, the intensive Opportunity Zone Justice Accelerator, urban agriculture training for returning citizens by returning citizens, and branding and marketing support through the Coming Home Coop.

The Aspire to Entrepreneurship program has, from its inception in 2016, have been stakeholder driven. Partner and community stakeholders developed three central principles that drive the program implementation and design.

Those principles are:

1. Meeting People Where They Are
2. Building a Community
3. Building Community Wealth


Congratulations to the winners of the Aspire 2021 Pitch Competition, who each received the maximum grant amount!

Kwabena Nkrumah (TJ Motors)
Rylinda Rhodes (Mane Rhodes)
Anthony Foster (Clean My Place)
Natango Robinson (Expert Installations)
Wendell Smith (Handbags by Wendell)


What’s Going On 

See upcoming events and sign up for our Aspire email list here: DSLBD Eventbrite