Nine community members, including the CEO of Defy Ventures, joined UW-Madison Extension Entrepreneur in Training (EIT) Bootcamp for a special coaching event at the end of May. In breakout rooms, EITs had 2 minutes to share an overview of their idea. Coaches then had about 10 minutes to ask questions and give feedback. This was the first time EITs had shared their ideas with others outside of their peers, and they were nervous. They reported afterward feeling grateful for the suggestions and ideas they received. One was even able to incorporate an idea given in the first breakout to his pitch in the second, which led to a stronger discussion and improved concept. Coaches commented on how grateful they felt to be a part of the process as EITs move toward economic independence. One said it was inspiring to see how the EITs are taking charge to make something positive happen. Two more milestone events will occur before this cohort graduates on July 21. These events serve to improve business viability and also build empathy among the community participants, which leads to structural changes in the workforce and incarceration systems, long term. To join in as a participant or coach for Cohort 2 starting July 26, email firstname.lastname@example.org.