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This thesis investigates how firms act entrepreneurially and strategically in heavily regulated sectors. Over four studies, the thesis develops a deeper and more empirically grounded understanding of how entrepreneurial and strategic actions are developed and combined. It is examined how firms’ internal organizational resources can prepare the ground for entrepreneurial and strategic actions as these resources can facilitate such activities (Ireland et al., 2009). The literature identifies several internal organizational resources that influence the success of both activities. This thesis particularly examines three of these resources: management support, work discretion, and rewards/reinforcements. In addition, it is explored how firms can use their external embeddedness to act entrepreneurially and strategically through decision-making and networking dynamics. Finally, it is examined how the combination of entrepreneurial and strategic actions is manifested. A mixture of qualitative and quantitative methodologies is used to provide a more comprehensive analysis of the investigated issues. The results show that firms use their internal organizational resources to develop and conduct both types of activities. These internal organizational resources appear to be important organizational antecedents that drive both types of activities. The findings also illustrate how firms use their external embeddedness to identify opportunities, mobilize beneficial resources, secure a competitive advantage, overcome the difficulties inherent to heavily regulated sectors, and create a new market. This was possible through combinations of entrepreneurial and strategic activities conducted through effectual and causal decision-making and network dynamics. Finally, the results show that the combination of entrepreneurial and strategic actions was manifested in different ways. In the examined financial services firms, the combination of both activities was manifested through the design of adapted internal organizational resources that facilitated the development and combination of both types of activities.  The combination was challenged by two opposite organizational resources: top-down managerial control (centralized decision-making) and bottom-up freedom (decentralized decision-making). In the case of the new venture creation process, the combination of both activities varied depending on changes in the external environment, and it was sometimes facilitated but at other times challenged by those changes. Overall, the thesis offers several theoretical, managerial, and methodological contributions to a range of scholarly conversations, including the literature on strategic entrepreneurship, entrepreneurial decision-making, organizational preparedness for entrepreneurship, business networks, and the new venture process.