Reboot is an organization dedicated to making inherited Jewish traditions vital and resonant to the generation of Jews now in their twenties and early thirties. Reboot facilitates opportunities for young Jews to gather together, engage with one and other, and question what Jewishness means in their lives. Founded in 2003, the organization has grown rapidly and now publishes its own quarterly journal while fostering collaborations that create books, records, films, salons, events and other cultural products. In 2005, Reboot decided to take some time to reflect on how its work impacted the lives of its participant stakeholders. The challenge from an evaluation perspective was that Reboot is quite explicit in stating that it does not operate with an a prior agenda. Instead, it seeks to create a space within which participants can find one another, define for themselves what matters and work together to create meaningful communities. Given this orientation, an evaluation based on outcome assessment was irrelevant. Our approach instead was to conduct a series of extended interviews with Reboot participants to learn how they perceived the organization and how it had touched their lives. The findings from these conversations documented the strong sense of ownership participants felt towards the organization and the direction(s) they wanted it to take moving forward. It also provided a better understanding of the kinds of support participants wanted from the organization as they expand existing communities and build new ones.