3 things we learned while serving formerly incarcerated entrepreneurs in 2022

In 2022, we worked with 50 formerly incarcerated people every month on average to help them on their entrepreneurial journeys. In prisons and on Zoom, from the idea stage to the growth stage, we have served hundreds of formerly incarcerated entrepreneurs since we launched Determination, Incorporated in 2018. 

At the beginning of each of our biweekly Be the Boss business support group meetings for formerly incarcerated people, we read our community values and expectations, and define what community means to us: “Community is when people come together to accomplish a common goal. People in community: work in solidarity, live in harmony, and hold each other accountable.” 

As we head into a new year, we wanted to share three things we each learned in 2022 while serving formerly incarcerated entrepreneurs and building our second chance entrepreneur community. If you want to join our community, scroll to the bottom to learn how.

From Kyle J. Benson-Smith, Executive Director: 

A startup entrepreneur needs 3 things to succeed: 

  • An entrepreneurial mindset: You must be able to solve problems, create value, and build trust with your customers.  
  • A profitable business model: Whatever the product or service, once the initial break even point is hit from the startup investment, you gotta make more money than you spend and have systems that make that happen over and over again.
  • Staying power: It will take time to make even the very best business plan a reality. Entrepreneurs must have the personal, social, and financial wherewithal, and a plan, to ride out the early growth stages. 

Entrepreneurs need more discovery, less invention. “If I build it, they will come,” is a very risky way to start a business. It may work, or you may lose a bunch of money and never have any real customers. “If I learn what they need and will pay for, I can be their favorite, most trustworthy provider” is a much less risky proposition. Find your future customers and learn what they need by building relationships with them. All great things take time and start with a single relationship. 

Let us all stop using “We check backgrounds” as a shorthand for “You can trust us” and switch instead to “We verify values.” I saw a sign at a hardware store advertising their local service providers that said “We check backgrounds.” The subtext was “We won’t send a ‘criminal’ to your house.” Due to mass incarceration and over-criminalization, it is estimated that 1 in 3 Americans have a criminal record. It does not make economic or social sense to write off ⅓ of the American public. No one wants to be judged for the rest of their lives based off of the worst thing they ever did. Kansas City would be a more compassionate and fruitful place if more people (employers, landlords, decision makers, and everyone else) gave people with criminal records the benefit of the doubt instead of writing them off categorically. AND if more people with criminal records made it their mission to EARN the trust of others by showing that they can live out their highest values consistently (i.e. honesty, communication, dependability, excellence). Trust takes time and starts in relationship with others in a restorative community (a.k.a., what we try to do better every year at Determination, Incorporated!)   

From Leslie Walton, Entrepreneur Success Manager: 

It’s important to be willing to meet people where they are and adjust accordingly. Not everyone learns at the same pace or in the same manner. Being a resource for someone that is starting a business, or making changes to their current business, means that you are going to have a melting pot of entrepreneurial journeys. We will encounter those that are ready to hit the ground running and those that still need to move more cautiously; all in the same workshop. It’s more important to make sure that regardless of the starting point of the person, that we as an organization are available with the resources – whenever they’re ready to get started. 

Defining what success looks like has to be personal. We all have different starting points, experiences, perspectives, triggers and values…just to name a few. What may seem simple for some may be a huge step for someone else as they experience entrepreneurship. Defining what success looks like has to be a personal goal, because it is a personal journey. It can’t be stemmed from trying to duplicate what someone else is satisfied with because that will be their image of success and sure pathway to not feeling successful. Steps to success need to be taken in a person’s own shoes so that the sense of accomplishment remains genuine. 

Being a part of the community starts from a willingness to learn about who else is a part of that community. Helping to build a community means that you are willing to be a part of the bigger picture. However, if a person is unaware of who else also belongs to that community, how will you understand what your role is to help it? Even more, how will others know how your business will contribute if you’re missing the heart of the community? That heart is relationships. Communities form one member at a time. Communities grow when those members acknowledge their interdependency and are able to coexist… willingly. 

Our Be the Boss business support group community is for formerly incarcerated people in the Kansas City area who are interested in starting or growing their business. They receive information, resources, contacts, connections and support to help them grow their business, and a community that believes in their ability to succeed in business.

We meet on the second and fourth Thursday of each month from 6:30-8pm on Zoom and our next meeting is next Thursday 1/12/23! To join, fill out this quick form with your contact information and we will be in touch!

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Determination, Incorporated is a 501C3 nonprofit in KCMO empowering formerly incarcerated people to seize employment and entrepreneurial opportunities in home building, home improvement, and affordable housing. To learn more, contact us here.

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