The External Enablers framework was developed to provide structure and terminology for the analysis of entrepreneurial opportunities. External Enablers (EEs) refer to changes in the environment such as regulatory changes, demographic shifts, or new technologies that enable an individual to create and develop ventures (Davidsson, 2015; Davidsson et al., 2020; Kimjeon & Davidsson, 2021). The framework aims to explain the cause-effect relationships between environmental changes and benefits that ventures experience, via EE mechanisms. EE mechanisms connect to responses in entrepreneurs through relational qualities called opacity and agency intensity. However, recent studies have found that entrepreneurs may ignore significant external changes in the environment, regardless of opacity and agency intensity considerations. Consequently, something else might explain agents’ engagement in venture creation. Another shortcoming of the framework is that it has yet to integrate the possibility that EEs might trigger consecutive EEs, in addition to agents acting on them through, for example, cascading effects. This thesis explores entrepreneurial action and its interplay with external enablers. We investigate why certain individuals act entrepreneurially upon multiple EEs. Previous research has stated that entrepreneurs may ignore opacity and agency intensity considerations. Hence, opacity and agency intensity may not be enough to explain why agents act on EEs. We conducted a qualitative multicase study, to identify patterns and relationships for theory building adhering to grounded theory traditions. Four cases from the Swedish wine industry were chosen, two “pioneers” (that is, early entrants in the wine industry in Sweden) and two “followers” (that is, later entrants). The industry serves as an appropriate empirical setting due to its novelty, where the environment changed rapidly, enabling a new industry to emerge from the 90s. Archival material and semi-structured interviews were combined, where a total of 21 interviews were conducted with vineyard founders, owners, and one expert. The findings show that the pioneers faced high opacity and agency intensity. Therefore, we introduce a third relational quality called Enthusiasm Fit. A high enthusiasm fit helps the pioneers “see through” a high opacity and overcome agency intensity, resulting in acting upon multiple and consecutive EEs. We also found that pioneers contribute to creating other EEs, resulting in cascading effects, where one EE generates reactions in another. Moreover, the followers don’t require a high enthusiasm fit but need the cascading effects produced by pioneers, to lower opacity and agency intensity considerations.