Small resource‐based communities across Canada are experiencing rapid change within a volatile, fluctuating global economy. As communities seek to diversify their economies, they are enduring complex provincial and federal neoliberal policy environments that offer fewer funding resources while offloading more responsibilities onto local governments. Drawing upon the case studies of Burns Lake, British Columbia and Grand Falls‐Windsor, Newfoundland and Labrador in Canada, we explore how small municipalities are using municipal enterprises to generate revenue and assets that may lead to new economic pathways. Our findings suggest that municipal entrepreneurial strategies are producing mixed success to break from past forest‐sector dependencies. These small municipalities still struggle with developmental and operational risks, as well as debates about whether to use revenues to meet new municipal responsibilities and increased demands on aging infrastructure and services versus transformative change.