Questions of how entrepreneurs exploit opportunities to create value are a big part of the discourse on creative work in contemporary societies (Alvarez et al., 2013). Entrepreneurs often build their creative journey by forming social bonds of opportunities (Daskalaki, 2010) that are meant to help creative work, but also constitute challenges to creative freedom (Montanari et al., 2016). This second aspect is not explored enough in studies on entrepreneurial venturing (Lingo, 2020), and a deeper analysis of the ambivalence of relational bonds may foster a better understanding of today’s entrepreneurial creativity in practice. Does the construction of ties with different actors and motivations necessarily go in the same direction in terms of creativity or can they contrast? How is the contrast solved? These questions are significant as entrepreneurs often experience that financial bonds highly limit their creative work, and vice versa that creative work is played not totally taking into account economic concerns. This is particularly true for entrepreneurs in the CCIs for the dual nature of their work (Lampel et al., 2000), based on the balance between the production of cultural and symbolic meanings for society (Jones & Townley, 2016) and economic wealth (Lounsbury & Glynn, 2001). Among those, small and micro cultural entrepreneurs are exposed to higher uncertainty than others, but they are also recognized as the most diffused and important drivers of European cultural variety, if in the last year they were conferred specific attention through resilience policies (as done in Italy for the independent publishing sector). We thus propose an inductive inquiry (Glaser & Strauss, 1967) carried out through an in-depth analysis of a single revelatory case (Siggelkow, 2007; Yin, 2009), that well represents the ambivalence of the creative process of small entrepreneurs in the CCIs. Our multifaceted venture was born in the mainland of Venice in 2006 with the mission to become a cultural reality dedicated to narrative and theatrical languages for young audiences. Funded as a social cooperative by a group of artists, the company moved through a sequence of changes where both its inner configuration and its external context were shaped by the dynamics of bonds and ties with a number of local actors, such as schools and universities, public and private institutions, and the 1 Corresponding author: Monica Calcagno, Ca’ Foscari University, Fondamenta S. Giobbe, Cannaregio 873, Venice, calc@unive.it. municipality of Venice. From time to time, these unstable bonds constituted opportunities for entrepreneurial creativity and financial sustainability, while at the same were perceived by the entrepreneur as new obstacles to overcome. As a result, the entrepreneurial journey was configured as a continuous process of transformation where the opportunity of today had become the obstacle of tomorrow, regenerating the urgency of the entrepreneurial venture as a process of dynamic search for new (un)stable positions.