Management and entrepreneurship scholars have shown growing interest in developing theory and examining the interconnected issues that characterize Knightian uncertainty (KU)—an immeasurable uncertainty related to non-quantifiable phenomena common in businesses. However, they address little regarding the non-probabilistic and non-statistical aspects of KU that influence entrepreneurial qualitative judgment. My critical argument is significant because enhancing our understanding of KU’s unique characteristics opens up new research avenues in entrepreneurial cognition, particularly its implications for Artificial Intelligence (AI) in organizations. My perspective is grounded in a broader possibility theory based on fuzzy set theory. This article goes beyond critical extensions and offers innovative insights into how entrepreneurs navigate KU, highlighting the connections between AI, entrepreneurship, and organizations.