D.C. Pilot Trains Offender Entrepreneurs

Image: Pixabay

The District of Columbia has launched a pilot to overcome employment obstacles by training offender entrepreneurs to small business self-sufficiency.

In Washington, D.C., a one-year Aspire to Entrepreneurship Pilot is helping up to 25 justice-involved individuals with a conviction for a misdemeanor or felony as an adult to overcome employment barriers and develop small businesses.

Such an idea is not new. Business professionals have mentored offender entrepreneurs through programs such as Defy Ventures, which pairs business resources and people with criminal backgrounds. The non-profit finds offenders often posses natural leadership and people skills, according to Forbes.  A 2015 article in Fast Company also explored entrepreneurship as an answer to recidivism, profiling a gym designed to connect the Boston tech community with young men that have criminal records in order to inspire new thinking about innovative career options.

D.C.’s Aspire to Entrepreneurship Pilot was recently awarded a $10,000 U.S. Conference of Mayors (USCM) DollarWise innovation grant to help expand the offender re-entry program.

How It Works

First, approved applicants become trainees. They learn computer skills, financial basics, how to start a business and then move into crucial entrepreneurial development topics, like creating marketing plans, developing financial projects and how to manage a business.

Going through the modules is their full-time job during training, and they have mentors and are required to keep a journal that logs their learning experience.

The aspiring offender entrepreneurs receive a stipend of $9.00 per hour, and have the opportunity to open Individual Development Accounts (IDAs), which are savings accounts held in escrow to be used for asset building purposes, like developing their small business. IDAs reward with matching funds and interest, and those set up through D.C.’s Aspire to Entrepreneurship Pilot will match participant dollars 8 to 1.


Program participants must meet a certain set of requirements — they are not on government assistance, for example. But they also must demonstrate need by meeting three of six defined barriers to employment:

  • English language deficiency with an inability to speak, read or write the English language
  • Lack of a secondary school educational credential, such as a high school diploma or its recognized equivalent
  • Documented history of substance abuse
  • Homelessness
  • Verified history of job cycling
  • Conviction for a serious or violent offense

The program was created by the District of Columbia Department of Small and Local Business Development, the District of Columbia Department of Employment Services, Court Services and Offender Supervision Agency for the District of Columbia, Capital Area Asset Builders and the District of Columbia Office of Returning Citizens Affairs.

The USCM DollarWise program specifically focuses innovation grants on integrating financial education into English as a second language, prisoner re-entry and public housing initiatives.

Learn more about the entrepreneurship pilot on the D.C. Office of the Deputy Mayor for Greater Economic Opportunity website.

About the author

Andrea Fox

Andrea Fox

Andrea Fox is Editor of EfficientGov.com and Senior Editor at Lexipol. She is based in Massachusetts.