Why Not Prosper, Inc.

The Why Not Prosper Entrepreneurship Academy was created for formerly incarcerated women to teach them about the fundamentals of starting and growing their own businesses.  Our 6-week class starts out with discussing the importance of entrepreneurship education including:

• Building strong relationships
• Developing analytical problem-solving skills
• Grit
• Confidence
• How to address job market discrimination against the formerly incarcerated
• Self-motivation and ownership
• Goal planning
• Business plans and Structure including feasibility analysis
• Idea Development, Supply Chain, Stakeholders
• Marketing
• Financing and Technology
• Making Youth Pitch, Telling Your Story, and Measuring Impact

Our skills-based units include:

• Goal planning
• Business plans and Structure including feasibility analysis
• Idea Development, Supply Chain, Stakeholders
• Marketing
• Financing and Technology
• Making Youth Pitch, Telling Your Story, and Measuring Impact

At the end of our program, participants have created their own personalized manual and plan to start their own business.  They also learn about the strengths of their fellow participants and create lifelong connections that serve to strengthen their will and resilience in building their business long-term. 

The Entrepreneurship Academy engages participants using processes focused on skill attainment and practice-based learning.  Technology is utilized in the delivery of the course and as lesson content related to creating and optimizing their businesses.  Our approach fully incorporates human-center design by meeting our participants where they are in their process, interests, and skills.  All of our participants are formerly incarcerated women who have varying levels of education, exposure to the business community, and experience interacting with the larger community in a healthy or positive way.

Over 1.9 women are released from state prisons and local jails annually.  Two-thirds of incarcerated women are mothers to children under the age of 18.  Upon release from incarceration, women face a plethora of challenges when integrating back into their community most significantly capped by their inability to get and maintain employment for a variety of reasons. Most notably, many women face interminable parole after release. 

For many formerly incarcerated women, owning their own business is the best way to secure their economic freedom and stability for their family.  Barriers to entrepreneurship include lack of:

• work experience and basic understanding of concepts required to run a business
• family and community support to help with financing and startup costs
• education and, in some cases, low literacy level
• low self-esteem related to years of abuse, discrimination, and unsupportive family/community. 

The discrimination that accompanies being on parole is a major barrier for formerly incarcerated women.    

Formerly incarcerated women need specially tailored entrepreneurship education programs that include supportive services such as housing, family reunification, stress management, recovery support, and case management.  All of these complimentary services meet their primary needs related to healing in order to prepare them to start their own businesses as entrepreneurs.  

The Why Not Prosper Entrepreneurship Academy serving formerly incarcerated women align with the Challenge in 2 areas:

• Offering focused guidance/professional development for building specific functional skills around strategic planning, human resources, process improvement, and research and testing products/services.
• Supporting and fostering growth to scale through comprehensive and relevant technical support assistance including legal aid, fiscal management for sustainability, marketing, procurement, etc.

Why Not Prosper (WNP) in itself was an entrepreneurial endeavor started by a formerly incarcerated woman who, once released, found there were no services that met her needs and the needs of her sisters being released from incarceration.  She started her own nonprofit organization when every door was slammed in her face.  Rev. Dr. Michelle Anne Simmons did not have any formal entrepreneurship training but created our current agency through tenacity and grit.  The Entrepreneurship Academy is her vision to help other formerly incarcerated women start their own businesses with a hand up including skills-based training and resources instead of a handout.  By supporting and fostering formerly incarcerated women in starting their own businesses,  WNP helps moms create stability for their children by earning family-sustaining wages.  This helps to strengthen not only each family but the overall community and works to break down the prison pipeline in our poor, low-resourced, communities of color.

Our program aligns with the Challenge through the skills-based education program provided combined with mentoring by local business people interested in growing and strengthening the community.

Our target population is formerly incarcerated women.  Most of our women are mothers and experienced high levels of interpersonal violence before and after incarceration.  Many of our women have experienced substance use disorders - many concurrent with mental health issues.  All of our women experienced varying levels of discrimination post-incarceration which led to issues around safe housing, employment, healthcare, family reunification, educational attainment, etc.  Last year we served 732 women over the age of 18 in our range of Why Not Prosper programs including 45% African American, 15% Hispanic, and 40% White.  All of our clients experience high levels of poverty and come from high crime, low resourced communities.

We understand fully and intimately the needs of our target population and develop programs and services tailored to these needs because we are governed by the philosophy of "nothing for us without us".  At Why Not Prosper, formerly incarcerated women hold positions at every level of the organization from program staff to c-suite and board of directors.  Our founding executive director is a formerly incarcerated African American woman who wanted to create a safe space where formerly incarcerated women could heal and create the lives they want to be happy and create strong, healthy families that will, in turn, create strong, healthy communities. 

Of note, a large percentage of our staff, leadership, and board are African American.  We are committed to serving all formerly incarcerated women regardless of race, ethnicity, or background.  However, the discrimination faced by formerly incarcerated members of communities of color is amplified and it is important to our organization that we are sensitive to those situations.

We have piloted this solution at our location in Philadelphia.  This was implemented as both an online and in-person solution.  Why Not Prosper currently operates in Pennsylvania with our main site in Philadelphia and a new site coming onboard in Harrisburg.

The mission of Why Not Prosper is to help women from prison systems discover their own strength by providing them with the support and resources that will empower them to become responsible, economically self-sufficient, and contributing members of the community.

We view this Entrepreneurship Academy as an outgrowth of our mission by helping formerly incarcerated women become economically self-sufficient by launching small businesses.

Our mission is to help women from prison systems discover their own strength by providing them with the support and resources that will empower them to become responsible, economically self-sufficient, and contributing members of the community.

Why Not Prosper accomplishes this through the following Theory of Change:

Activities:  Provide a skills-based entrepreneurship program to formerly incarcerated women to help them identify an idea, create a plan, operationalize the plan, identify supporters and backers, and launch.  Classes can be held in person or virtually.

Outputs: Women gain knowledge about how to start a business and what is involved.  Tangible outputs include a product or service, a business plan, an operational plan, a marketing plan, and a launched small business

Short-Term Outcomes:  Women are able to identify their strengths and needs relating to starting a business.  Women get to know each other better and form a supportive peer group.  Women interact with instructors and guest speakers to identify new champions and advisors for their business.

Medium-Term Outcomes:  Women feel supported and increase their self-esteem.  Women are able to meet their own needs in a healthy, supportive way.  Women are more willing to continue their education, increase their skills, and hire other formerly incarcerated women. 

Long-Term Outcomes:  Women become self-sufficient and earn family-supporting income.  This allows them to attain stable housing and facilitates family reunification, as well as overall stability.  All of this converges to decrease recidivism amongst formerly incarcerated women and break the cycle of generational trauma within families related to substance use, abuse, incarceration, and discrimination.

During our pilot program, we had 40 women complete the Entrepreneurship Academy and 16 started small businesses.

With a full iteration of our program, we are aiming for 100 women to complete the Entrepreneurship Academy with 50 women starting small businesses.

In five years, we aim to serve 500 women through the completion of the Entrepreneurship Academy with 300 starting small businesses.  Additionally, within 5 years, we would like to expand our Entrepreneurship nationally to formerly incarcerated women throughout the country.

Rev. Dr. Michelle Anne Simmons is the Founder and currently serves as Chief Executive Officer of Why Not Prosper.  She was formerly incarcerated and is a recovering addict.  In 2008, Michelle graduated from Chestnut Hill College with a bachelor’s degree in Human Services, and in December 2010 she graduated with a master’s degree in Counseling Psychology. She is also a Certified  Allied Addictions Practitioner and a Certified Domestic Violence Counselor. In addition, she received her Doctorate in Ministry from Friends International Christian Academy. 

The rest of our team has been hand-picked for the Entrepreneurship Academy team because of their skills and commitment to giving our women a hand up instead of a handout including Marcus Greene who is our Director of Operations, Joe Morrison who is our communications and business consultant, and Namrita Narula who is our intern from the Wharton School of Business.  This team is committed to serving formerly incarcerated women and helping them to create the lives they want.

The financial award associated with this award program would be an unbelievable gift for our program so we can pay for the staff salaries related to the Entrepreneurship Academy.   In reading about the 5-month tailored support program run by MIT Solve, we believe the range of topics that will be covered will educate our team about how to improve our program in-depth as well as scope.  Learning about this array of topics will help us to build a richer curriculum for our participants particularly around needs assessment, creating a network of resource partners, refining a business model and theory of change, building our impact measurement, participating in the "solveathon", and particularly attending the Truist Leadership Institute Retreat in 2023.

Given that we are only anticipating barriers relating to funding, the Challenge can help us with a financial award but also some of the peer-to-peer work may help us by opening new networks for us to explore for funding.

We would love assistance in creating specialized video content to go with our education program.

We are always looking for ways to increase the efficacy and impact of our board and would love some help with human capital.  Additionally, learning more about different business models is always helpful in the nonprofit world where we often get stuck in a box.  Increasing our financial acuity and scope will be helpful in identifying other funding sources.  Monitoring and evaluation is an area where we are always looking for new ways to do things.  As a nonprofit, we would love some help related to evaluation in the business world.

We are open to partnering with any and all organizations.  The most important thing we bring to the table is spreading the word about how and why we need to support formerly incarcerated women to create stronger, healthier communities. 

Regarding types of businesses, we are interested in partnering with all businesses, small to large, in a variety of industries.  We also look at their partnerships as referrals for our participants' small businesses that they develop out of our Entrepreneurship Academy.