Fostering innovation, managing the innovation process, and promoting entrepreneurial activities have long been identified as critical elements of successful economic and social systems. By their very nature, both innovation and entrepreneurship relate to the creation of novelty and the introduction of change, i.e., dynamics. This means that despite the considerable progress that has been made in our understanding of both the theoretical characteristics as well as practical applications of innovation and entrepreneurship, many aspects of these analyses require constant updating. Further, the evidence increasingly suggests that many relevant aspects are not only context specific but also undergoing significant structural change. These include the micro and macro stimuli of innovation and entrepreneurship processes, the factors that contribute to start-up and innovative firm performance, as well as the broader effects of innovation and entrepreneurship on economies and societies. This dissertation explores how innovation and entrepreneurial processes and outcomes vary across linguistic, geographic, regulatory and technological contexts. The empirical evidence regarding all of these aspects remains mixed and ambiguous, indicating a need for more nuanced conceptualizing. The relevance of contextual idiosyncrasies to innovation and entrepreneurial processes of these aspects remains understudied, presenting an opportunity to extend theory and make a valuable contribution. In the first chapter of this dissertation, I introduce the groundwork for the dissertation, and review the conceptual foundations of each of the three dissertation studies. I also summarize the findings and insights, braiding them together to show how my findings reinforce each other, forming an organic whole. Each subsequent chapter addresses different aspects of innovation and entrepreneurial processes mentioned above. In the second chapter, I evaluate how linguistic variability relates to cross-national innovation processes and outcomes. In the third chapter, I assess how different forms of connectivity across geographic space among innovators contribute to the development of regional innovation systems across Italy’s core and peripheral areas. In the fourth and final chapter, I evaluate the relevance of regulation and technological change to the entrepreneurial process in a specific context within the financial services industry. / Business Administration/Strategic Management