Serendipity—the process of making valuable and unexpected discoveries by happenstance, often during an exploration process aiming at a different outcome—is a salient construct in the entrepreneurship and business strategy literature. Despite scholars started to gather some insights on serendipity, the elusive nature of this concept still hinders its incorporation in strategy frameworks. Against this backdrop, this study explores the root causes of serendipity in entrepreneurial settings and examines how entrepreneurs and business leaders could convert serendipity emergence into serendipity realization. Adopting a grounded theory approach, we conduct semi-structured in-depth interviews with 53 entrepreneurs and business leaders, anchoring to the pillars of the Gioia methodology. Our investigation reveals that serendipity in entrepreneurial ventures is not merely a product of chance but could be fostered by leveraging five distinct organizational layers encompassing (1) operations’ complexity, (2) organizational, leadership, and individual capabilities, (3) organizational climate and culture, (4) organizational structure, and (5) organizational openness. The study also points out that the process of realizing serendipitous value exhibits absorptive capacity patterns: (a) recognizing, (b) assimilating, and (c) incorporating serendipitous opportunities. Key implications, together with limitations and avenues for future research, are then discussed.
