This dissertation explores the entrepreneurial practices of the last Soviet generation, focusing on the examples of retired scientists and staff from a defunct institute for environmental science in post-Soviet Eastern Siberia. The subjects of this research currently find themselves in a precarious economic situation and rely on different reclamations of the material and conceptual remains of the institute that once employed them. Through such remains, these people are building their own economic projects, varying from a vernacular museum and small-scale conservation efforts to reselling discarded objects. Based on these examples, I explore the tension between public discourses about entrepreneurship on the one hand and the entrepreneurial practices of the urban poor on the other. The empirical data at the core of this study was gathered through field research in the period 2019-2022, as well as some archival materials. In analyzing the data, I rely on contemporary anthropological research on entrepreneurship and gleaning as well as on post-socialist labor studies, more broadly construed. Additionally, I engage with social scientific literature by Eastern European scholars, thus proposing much needed theoretical dialogues with often underrepresented work. Overall, I argue that in post-Soviet Russia there is a form of unlikely entrepreneurship that does not fit the immediate image we might associate with the word “entrepreneur”. These unlikely entrepreneurs, however, draw on the conceptual resource of entrepreneurship and engage in various entrepreneurial practices in building their own economic projects in a context of post-industrial economic decline. Furthermore, I demonstrate that there are implicit sociopolitical critiques that can be deduced from the labor practices of my interlocutors. Engagement with these critiques allows for an investigation of the ways in which labor practices and political imaginaries co-constitute each other. To this end, my dissertation concludes with showing how these entrepreneurial labor practices, depending on certain variables, can critique the state-sponsored version of the future, embrace it, or attempt to create small-scale alternatives.