This article shares the benefits, challenges and lessons that emerged from community foundation efforts to market regionally in Michigan both on a state level and within eight smaller regions. Drawing on six years of evaluation, research methods include: 1) individual interviews with 20 CEOs (conducted in 2000 and again in 2002) and five board members (conducted in 2002), 2) instrumented group interviews with two regional collaborations, 3) an in-depth ethnographic case study of one group over six years, and 4) review of documents developed by the regions.