Entering the twenty-first century is not just a step in time, it is coming into a new era where people are craving for valuable change and are willing to become more active in being part of it through both learning as well as community development [Prahalad and Ramaswamy (The future of competition: Co-creating unique value with customers. Harvard Business School Press, 2004a)]. Communities of connected, informed, empowered, and active consumers are challenging the world. According to Nijs (Imagineering the butterfly effect, transformation by inspiration. 11 International Publishing, 2014), “growing connectivity, interdependency, diversity and interactivity has major influences on the way we can create value in society.” Instead of passive users, today’s consumers want to be involved in designing processes. As Hargadon and Bechky argue (Organization Science 17:484–500, 2006), “collective consumer creativity is qualitatively distinct from individual consumer creativity—it occurs when social interactions trigger new interpretations and new discoveries that consumers thinking alone, could not have generated. If we realize that creativity is a systemic—as opposed to individual process, then we are led to broaden our perspective”. Already in 1958 Jacobs approached cities as living beings and ecosystems, unfolding the transformation of the urban environment and the regional development potential, especially for tourism and culture. She suggested that over time, buildings, streets and neighbourhoods function as dynamic organisms, changing in response to how people interact with them. This sentiment is now, more than ever, echoing into the tourism sector evolvement as such and its meaningful interpretation with and for all. How can we encourage innovation and how can we engage customers and participants in creating the future in order to satisfy the needs of the participants? Why is Co-Creating the future for all of us? How can we design (for) the future in order to ignite interaction? According to Tonder (Journal of Industrial Psychology 30(3):53–64, 2004) the new society is characterized predominantly by consumption where people create a sense of who they are through what they consume. Simply stated, consumers from a century ago were concerned about the utility value (does it solve my problem?) whereas today’s consumers focuses on the intangibles—cultural or symbolic—values (does it promote my identity?). This becomes valid for the tourism sector and especially the cultural one, whereas the entrepreneurial learning has become the collective learning and the exchange and co-creation of value, which leads to the introduction and increase of relevance of communities of practice. The current chapter aims to study the cross-border cultural tourism development of Bulgaria and Romania as a thriving possibility for entrepreneurial learning and communities of practice. It will unfold the existing potential of these countries and look into the specifics of how the complex nature of contemporary society is affecting the transformational essence of exchange versus value co-creation. The further objectives of this chapter are to analyze the value and elaborate on a model of entrepreneurial learning and community of practice establishment in the cross-border region of two economies in transition—the Bulgarian and the Romanian. These countries will be analyzed through the lens of cultural tourism by looking at the complexity and the value creation interaction possibilities that are enhanced by the entrepreneurial and community development.