A Retrospective: Cohort #4

Adeleke Omitowoju
Project 500 DC
Published in
5 min readJun 13, 2018

8 months of planning, 50 interviews, 12 weeks of sessions, 72 hours of personalized advisory, and one amazing night, brought us to this point. The below is a retrospective of the journey of our 24 graduating entrepreneurs from our Project 500 Emerging Entrepreneurs Program.

A few weeks ago, we had the honor of graduating 24 of Washington, DC’s most promising early-stage entrepreneurs. With Cohort #4 as they were called, we set out to do something different; design and deliver a cohort-based program that provided contextual technical assistance to help founders work through common early-stage challenges. All we asked from our participants was that they come with an open mind and a commitment to scale their companies. While Part II of this post will highlight some outcomes and KPI’s, we at least want to share insight on the key learnings for practitioners in the space.

The Problem

  • “Too many companies falter in the middle, go-to-market phase, exposing themselves to lower valuations, significant financing risks, and suboptimal outcomes.” (traction gap framework)
  • “Most founders don’t know what they should be focusing on and consequently dilute their focus or run in the wrong direction.” (startup genome)

User Personas

Design thinking methodologies teach us that we must have empathy for our users / customers to understand what drives them and what makes their experiences unique. Knowing this, we distilled our personas into two types. As we went through this process, we were intentional in ensuring that the pathway to success was incorporated so that we understood WHY they would want to / need to be part of our program.

  1. High Growth Small Business: These companies typically have or seek to acquire physical space, sell physical products and / or provide services. Performance tends to be dependent on the ability to sell the product and / or service to a localized market with the option to sell online.
  2. Tech and Tech Enabled: These companies have developed a product or service that is either digital in nature or delivered with the assistance of technology. A key success factor of this type of company is identifying a large enough market that is in need of the product or service while having the technical talent to deliver.

Our Approach

We had a thesis that no matter the type of company (tech vs non tech / consumer goods vs media) there were common challenges that we could help address. After extensive research and interviews, we found that indeed, as a new founder, preparing for and achieving scale is a common thread along with a lack of access to methodologies to do so. In fact, the odds of achieving scale are greater when entrepreneurs build their companies with scaling in mind at the early stage.

Building on the original program model, we enlisted instructors and subject matter experts who were themselves entrepreneurs and understood the needs of early-stage entrepreneurs. We also developed a matrix to map the business types to the desired outputs and outcomes.

Program Outcomes

Being an entrepreneur is lonely and for many, the risks of failure is high due to a lack of a safety net. Our team understands these challenges firsthand and in our efforts to put on world class technical assistance, we wanted our founders to leave with two things 1) a sense of community and 2) greater confidence in being able to achieve their business goals.

Program Outputs

Armed with the knowledge of WHAT our founders faced in terms of challenges, we now knew HOW to design a program that met their needs. We built our programming to focus on 4 major outputs that would be contextual in the sense that it met the founders where they were an additive in that it helped to supplement what they were / may already be focused on. The outputs were as follows:

  1. Business Model Canvas: framework for understanding & defining vision / business model / resources / measurement (crystallize vision)
  2. Pitch Deck: Multi-stakeholder synopsis of company, vision, value proposition and unique advantage. Can be used for both investors and stakeholders such as employees and customers (communicate vision)
  3. Financial Model: determine viability of business model given key assumptions informed by the business model canvas (facilitate capital readiness)
  4. Strategic Plan: mapping business goals to operational / financial metrics (facilitate scale)

Key Observations

  1. Cohort cohesion: After the program orientation session, participants immediately started connecting and exploring how to work together. This was exciting to us as we immediately saw new bonds being formed and new business partnerships emerge. This is not something you can plan for, but is just as, if not more valuable than the educational content.
  2. Workshop design: Our culture at Project 500 is data driven and we constantly poll our founders to learn about how we can improve our programs. Early on in the program we found that participants wanted more space to apply what they learned to have a greater degree of context and ownership. So, mid program, we shifted from an instructional model to a workshop model that emphasized application of the learned content. This helped ensure that the learning was contextual and tied to desired business outcomes.

In Conclusion

To see 24 entrepreneurs learn and grow over a 12 week process is hard to put into words. Cohort #4 is really a beautiful mosaic of ideas, aspirations and solutions to problems that many of us face. In the next post, we will provide some data on cohort KPI’s and future programming.

Big shout out to the partners and people who helped make this program a success:

  1. Beacon DC (cc: Aerica Shimizu Banks)
  2. Color Coded (cc: Pamela Assogba)
  3. humble ventures (cc: Harry Alford)
  4. Amazon
  5. Capital One
  6. JPMorgan Chase
  7. Brandi R. Suttles
  8. janbaker
  9. Kate Mereand
  10. Phil Reeves
  11. tulani
  12. Halcyon
  13. COPE with Affiniti VC
  14. Maude Okrah with Bonnti
  15. Brandon Andrews

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Adeleke Omitowoju
Project 500 DC

Venture Advisor @1863ventures / Startup Founder / Startup Mentor / 2x Father / Certified Nerd ✊🏿