Although previous research has extolled the importance of business failure as a precursor to transformational learning, few studies have explored the conditions under which such learning occurs or the content of the resulting knowledge. We explore several cognitive moderators of the relationship between failure experiences and a specific type of opportunity identification knowledge—the use of structural alignment processes. Results indicate that learning from failure is facilitated for entrepreneurs who possess a cognitive toolset that consists of opportunity prototypes and an intuitive cognitive style. Moreover, we found that prior professional knowledge negatively moderates this relationship.