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Failure storytelling enables entrepreneurs to learn vicariously from others’ experiences, yet most research examines such learning in face-to-face contexts where identity and trust are visible. In online communities, anonymity reconfigures these dynamics by altering how vulnerability is expressed and received. This study investigates how anonymity shapes failure storytelling and learning in a virtual entrepreneurial community. Using an inductive, mixed-methods analysis of 185 Reddit threads (2,773 comments) and 1,301 user profiles from /r/Entrepreneur, we integrate comment-level coding, user-level identity analysis, and thread-level comparisons to reveal three distinct pathways of vicarious learning - cognitive-diagnostic, socio-affective, and the hybrid emotional-epistemic - each linked to specific anonymity configurations and narrative framings. We theorize anonymity not as concealment but as a communicative affordance that structures how narrative risk, credibility, and resonance are negotiated. Trust, we argue, emerges as an interactional outcome rather than a precondition for learning. The study advances theory on vicarious learning, entrepreneurial failure, and sociotechnical affordances by explaining how identity-flexible platforms foster diverse forms of learning through peer storytelling.