Adding to approaches highlighting network dynamics as a basis for regional economic development, increased attention is paid to institutions as contextual factors contributing to explaining how and why economies change. Research has shown that firms tend to react differently to the same institutional configurations, with the main explanatory factors being their sectoral backgrounds and intra-firm characteristics. This study adds to these insights by examining a regional economy in France, that of Cognac, in which 300 firms are operating under homogeneous institutional preconditions. Despite these similarities, we identify different development trajectories from the 1990s onwards. Our observations illustrate how firms’ responses to external change diverge and bring them on different trajectories due to different positions in the industry hierarchy and different experiences and capabilities among individuals within firms. The study contributes to the better understanding of mechanisms of path dependence, which have gained wide recognition in the literature in the recent decades.