This is a study of factors that influence the effectiveness of collaboration among small business support organizations (SBSOs) in four upstate New York Counties, two of which are higher functioning collaborative groups and two which are lower functioning collaborative groups. The study was motivated by the experiences and observations of the leaders of the Entrepreneurship Education and Outreach (EEO) program at Cornell University over the past few years as they have worked to provide business training courses in upstate New York counties. Many communities attempting to support the wide and diverse range of needs of smaller businesses are experiencing mixed outcomes. Unfortunately, this can be true even where there is a prevalence of support services and good intentions. Often resources are poorly organized, poorly understood, and/or inadequate to accomplish overall community economic expectations for serving small businesses. As a result, communities may experience scattered successes mixed with disappointing efforts or programs that never reach their full potential. One possible solution to the problem is for a community’s SBSOs to have effective cooperation and coordination of the differing missions, accountability, resources and personalities among the numerous support providers. However, collaboration of SBSOs has posed continuing challenges for many communities. To summarize, this research found that leadership, communication, public policy climate and community culture have a critical impact on collaboration among SBSOs. When these factors are negative, it can trap SBSOs in a type of inertia that keeps the barriers foremost in the minds of potential participants. On the other hand, once positive experiences and good leadership creative the right climate, the same barriers that once kept SBSOs from working together seem to fade and a kind of self-sustaining momentum takes over. SBSOs, funding agencies and others interested in increasing collaboration should examine what can be done in their own communities to break the inertia that keeps collaborations from flourishing. Implications are identified for communities, SBSOs, and community educational institutions like the Cooperative Extension system.