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To sense and adapt to uncertainty by leveraging prior entrepreneurial knowledge is a critical ability. However, for many individuals, prior entrepreneurial knowledge is absent or underdeveloped. We investigate the ability of individuals without prior entrepreneurial knowledge to effectively adapt decision policies in response to feedback, while performing an entrepreneurial task. We model 10,000 “entrepreneurial decisions” nested within 217 individuals, to demonstrate how differences in metacognitive ability and feedback type promote (or alternatively impede) cognitive adaptability. Our findings suggest insights into the interplay between knowledge, learning, and cognition that are generalizable to activities and actions central to the entrepreneurial process.