To attract audience attention and approval, entrepreneurial ventures have to construct identities that are ‘optimally distinct’, balancing conformity to gain approval with distinctiveness to gain attention. However, despite the inherent challenges in creating such a paradoxical identity, little is known about how ventures attempt this in practice. Nor is much known about why they may fail, and what the cost of that is. To address these gaps, we conducted an in-depth case study of Bremont, a British luxury watchmaker that sought to carve out an optimally distinct position in the traditionally Swiss-dominated luxury watch industry. Drawing on a rich, 17-year dataset, we examine how Bremont used various identity claims to achieve this position. Our findings reveal that pursuing optimal distinctiveness can fail due to two key dynamics: early distinctiveness claims can spill over and constrain later efforts to achieve legitimacy, and distinctiveness claims can shape how legitimating claims are perceived by audiences. These dynamics can lead to stigmatization, binding ventures to low-status positions within their fields. By uncovering how identity claims may conflict and how pursuing optimal distinctiveness can backfire, we contribute to the literature on venture identity and optimal distinctiveness, highlighting the risks and constraints of this strategic approach.