This study extends theorizing on the impact of insiderness and outsiderness on entrepreneurial activity, its commercial outcomes, and the impact on individual entrepreneurs. We study the case of the self-marginalized canalboat community (a group of spatially mobile individuals living on boats in inland waterways in the United Kingdom) whose complex relationships with wider society defy simple insider-outsider dichotomies, and which we describe as 'boundary fluidity.' This group represents an intentional, alternative lifestyle challenging societal norms, particularly regarding home ownership, occupancy, and sedentariness. By investigating the power discrepancy between the self-marginalised and local governance on entrepreneurial growth or sustainability, we aim to extend the limited literature on self-marginalized entrepreneurship and to constructively contribute to recent interest in more nuanced forms of entrepreneurship. Focusing on the case of the canalboat community and utilising a multi-method qualitative research design, we find that for self-marginalised entrepreneurs, not only is entrepreneurship seen as an emancipatory tool, but the likelihood of facing challenges such as scalability constraints and resource scarcity is greatly increased in comparison to their mainstream counterparts. Moreover, unlike in other spaces of marginalized entrepreneurship, the boundaries between insiderness and outsiderness are particularly fluid, where entrepreneurs are willing to adjust their strategies to appeal to both insiders and outsiders, based on entrepreneurial goals.