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Prior research highlights storytelling as a means for entrepreneurs to establish venture legitimacy and gain stakeholder support. We extend this line of research by examining the role that projective stories play in setting expectations and the dynamics that ensue. Such attention highlights a paradox—the very expectations that are set through projective stories to gain venture legitimacy can also serve as the source of future disappointments. Because of inherent uncertainties that projective stories mask, ventures will likely deviate from their early projections, thereby disappointing stakeholders. This, in turn, can result in a loss of legitimacy. Recognizing that entrepreneurship is an ongoing process, we examine the constraints and possibilities of maintaining or regaining legitimacy through revised storytelling. We conclude the paper with implications for research on entrepreneurial storytelling as an ongoing process.