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How can entrepreneurs achieve legitimacy from audiences? A growing literature stream on the legitimacy of entrepreneurial identities has identified a trade-off regarding “optimal distinctiveness”: entrepreneurs need to claim distinctiveness to stand out from others, but also claim similarity to not break with social conventions. In this paper, we theorize how the interplay of individuals’ distinctiveness and similarity claims creates “optimal identity distinctiveness”, allowing entrepreneurs to gain legitimacy from audiences. Using a configurational (fsQCA) approach, we analyze conversation data (around 760’000 posts) from seven popular entrepreneurial online communities. Our results highlight three configurations that foster high levels of legitimacy and balance similarity as well as distinctiveness claims (creativity complements invention focus, purpose compensates unpopular high-performing, optimal similarity needs …