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What We Learned While Supporting Startups Founded By Returning Citizens

Harry Alford
humble words
4 min readJul 31, 2018

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In partnership with the Department Of Small And Local Business Development (DSLBD) and Changing Perceptions, humble designed curriculum and provided entrepreneurial training to support the Changing Perceptions Spring 2018 cohort. Changing Perceptions helps returning citizens, people in transition from incarceration to society, develop an ownership mentality in their futures by developing skills to help increase leadership in their communities and, in some cases, as business owners.

In Washington, DC, 75% of young Black men can expect to serve time in prison. Additionally, 50% of returning citizens are unemployed. This leads many to explore entrepreneurship, as this allows them to be their own boss. However, it is clear much more can be done to support those who want to launch businesses or gain entrepreneurship experience.

humble instructed training for 16 weeks of the cohort to support participants in the early stages of their business ideation and launch. After working with 15 returning citizens, we’ve compiled a short list of things we learned from facilitating the entrepreneurship portion of the program:

  • Although experts with regards to their perspectives, worldviews and target market, this cohort’s ability to iterate and pivot to new business models was incredible. Their eagerness to learn and adapt doesn’t reflect their years of confinement behind bars.
  • Maintaining balance between confidence, expectations and execution was probably one of the bigger challenges. For most, this is their first official introduction to entrepreneurship and being self-employed by legal economic means. Providing a risk-controlled environment where they can fail with our guidance increases their success once they graduate.
  • One hundred percent (100%) are developing services targeting markets that don’t mirror the consumer landscape of VC-backed startups. A majority of the companies we engaged with were lifestyle businesses focused on mental health, apparel, waste management, daycare, landscaping, food and other service-based businesses. This is a great arbitrage opportunity that continues to be overlooked by most firms and established corporations.
  • Alternative financing arrangements such as venture debt, equity crowdfunding, small business loans and grants from city agencies might be most advantageous for their stage.
  • Towards the end of the program, the group was tasked with designing a pitch deck. Creating a pitch deck is the merging of a story with a business. Nearly all buried the lede about their respective backgrounds detailing their incarceration. Understandably, I could see why they’d save it for the end of their deck or not at all, but what makes their narratives even more authentic and real is their lived experience and founder story. I’d encourage more to let us into their world and why they believe they have a solution for a problem worth solving.
  • The traditional Demo Day or situation where a founder is asked to publicly pitch her startup to an audience of investors is not an ideal format for returning citizens. At least not for those who are newcomers to entrepreneurship and launching a startup. With regards to entrepreneur support programs, Village Capital CEO, Ross Baird, believes there’s a distinct difference between ‘business model development’ and ‘leveling up for investment’. We designed our curriculum with the goal to help founders validate their business models. In the final two sessions, we conducted practice Demo Days to a select crew of investors who would provide honest and constructive feedback. This supported practice, before an external facing presentations, was an important step in the process and allowed a safe place for growth.
  • This cohort exhibited excellent public speaking skills. However, the layers of grit and passion encompassed within their voices doesn’t always translate well to pitch decks. Every person has a compelling story and none are the same. If you’ve ever watched Flikshop founder, Marcus Bullock, speak then you would understand. All the more reason to use an alternative to a traditional Demo Day.
  • Sixteen weeks is not enough time, especially for the most promising ventures. It’s of the utmost importance in relation to the development and success of the founders to receive subsequent programming to implement the strategies they learned in the prior programming. This includes building out repeatable sales funnels, acquiring customers and finding product/market fit. Furthermore, once they are ready to spread wings, business education should be amplified and development should be leveled up to identify funding (if necessary) to allow businesses to grow.

humble is proud to support DSLBD and Changing Perceptions. We look forward to training returning citizens in DC and beyond who want to pursue entrepreneurship and self-employment.

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Harry Alford
humble words

Transforming enterprises and platforms into portals to Web3