After World War I, an architectural and urban movement for protecting heritage emerged. An important turning point for urban conservation was when the focus shifted from the process itself towards questioning why to conserve (what are the values being safeguarded) and for whom? Adaptive Reuse of Cultural Heritage became a two faceted tool which tackles contemporary needs with high quality reuse projects and provides evidence of the multilayered positive impacts. Although there is no commonly agreed upon definition of cultural entrepreneurship, the authors define it as a set of activities aimed at harnessing a cultural business opportunity. The novelty stands in being innovative in transforming cultural values into economic values. The process of creating new adaptive reuse of heritage buildings is about the business of transforming abandoned, underused or not in use cultural heritage into common goods which reflect needs and aspirations of the contemporary local community with respect to environment and social practices and interactions. It is timely for cultural entrepreneurs to embrace circular and innovative organizational forms of business and finance for managing their cultural activities. Cultural entrepreneurship is auspicious because it endows innovative concepts on quantity, quality and manipulation of resources in tandem with novel ways of empowering consumers, prosumers and the community at large in governing the common goods. This paper illustrates the process of developing a circular business model for adaptive reuse of cultural heritage in line with the guidelines of the Historic Urban Landscape approach. It also delineates how the circular business model workshops were conducted throughout H2020 project CLIC and what were the main results.