Optimal distinctiveness postulates that entrepreneurs need to position themselves as distinct as legitimately possible. Extending this view on strategic positioning as a one-time decision, we examine how the most successful entrepreneurial content creators on YouTube repeatedly change their narrative in new video releases. Relying on organizational learning and performance feedback literature, we find content creators are likely to change if prior performance was below aspirations–expectations founded both on own and competitors’ past performance. This response, however, is non-homogeneous, suggesting that narrowly failing aspirations induces problemistic search that leads to increased change, while missing aspirations by a wide margin induces rigidity, self-enhancement, and less change. Content creators that clearly fail their aspirations therefore change very little in their next video’s narrative, while those that narrowly fail respond by releasing a video whose narrative is more distinct from their last own release as well as the market average but is simultaneously less distinct to the exemplar–the most successful content creator ``star’’ in the category. Our work has important implications on how aspirations affect entrepreneurial strategy decisions and adds organizational learning to the contextual factors that shape optimal distinctiveness. Extending the role of competitors from actors to either conform to or differentiate from to a source of learning adds to our understanding of institutional pressures and competitive dynamics in entrepreneurial markets.