Summary: Collectively, these studies inform our understanding of core stigma, but also make salient that much remains unknown about organizational stigma, particularly for entrepreneurial firms. This dissertation contributes to this lacuna. I explore the strategic actions of entrepreneurs who are building enterprises around a plant that not only has a negative public perceptions built over decades, but that is also federally illegal. In the first essay I use a qualitative methodology to examine how entrepreneurial firms attempt to destigmatize. I show that they do so through morality infusion , where they use narratives and substantive actions to connect themselves and their industry to an alternative set of values, and to create an identity and image that resonates with important audiences. In the second essay, I combine content analysis with fuzzy set Qualitative Comparative Analysis (fsQCA) to analyze how firms configure their narratives to account for the resources that they have at their disposal, and the ultimate effectiveness of those configurations. This study is situated in the context of nascent firms that are applying for licenses to operate medical cannabis dispensaries in newly legal Massachusetts. Overall, I develop theory to explain the entrepreneurial de-stigmatization and legitimation processes, thus contributing to the literatures on entrepreneurship and core stigma. Furthermore, I also contribute to the literature on entrepreneurial storytelling.