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Building on the idea of the embedded-agent-paradox that sheds light on the structural difficulty of presenting the field with innovation, this study seeks to expand the discussion on the link between agents’ position and their ability to promote change. Analyzing the case of an entrepreneurial school that operated for four years and then close, reveals the interrelations between the entrepreneurs’ backgrounds, positions, and understanding of the field’s expectations. Coming from different fields, their educational experience (as students, parents, etc.), led them to overestimate their acquaintance with the field. This partial knowledge, alongside investment of personal capital, described as a semi-embedded position that enabled identification of field’s lacunae but provided an only partial understanding of it for offering a sustainable solution.