Entrepreneurial Strategy and Learning

Abstract

Learning is a cornerstone of competitive advantage, especially in entrepreneurial contexts. Despite extensive research on entrepreneurial learning methodologies, we still lack understanding of fundamental constraints that limit learning effectiveness. This dissertation investigates key structural obstacles that hinder effective entrepreneurial learning: resource constraints, uncertainty, interdependencies, and bounded rationality. It provides novel insights into how these barriers manifest and interact in entrepreneurial contexts. The first study reveals a counterintuitive relationship between experience and strategic foresight: as entrepreneurs add features to successive products, the total interdependencies grow faster than their ability to anticipate them, leading to increasingly inaccurate forecasts. The second study reveals how novel recombination, while often associated with opportunities for outsized returns, also incurs the cost of managing novel complexity—obscuring the time and resources required for execution and increasing the risk of bridge financing and shutdown. The third study identifies a “mediocrity trap," in which firms launching lower-quality products receive ambiguous feedback and, as a result, persist longer despite negative market signals. This study challenges assumptions about learning with minimum viable products and rapid pivoting. Together, these studies highlight critical tensions in entrepreneurial learning and demonstrate that many learning challenges stem from structural barriers rather than purely cognitive limitations. This integrated perspective contributes to scholarly understanding of entrepreneurial strategy while offering practical approaches for entrepreneurs seeking to navigate these barriers and learn under constraint.