The relationship between business strategies and legal institutions is important for understanding the historical dynamics of modern capitalism. While legal history and economic history have remained distinct disciplines, a growing number of studies now populates a vibrant «borderland» between the two. Building on frameworks of legal history, organization studies, and «new entrepreneurial history», our contribution systematizes the relation of entrepreneurship and the law from a historical perspective of change. This paper explains how an analysis of this specific relation contributes to our understanding of economic change and addresses the question of synthesis and interdisciplinary connectivity by offering a conceptual triad that focuses on the problems of agency and change at the intersection of businesses and the law. This paper argues that economic actors have used, sought, and avoided laws to transform their legal and economic environments. Each of these interactions combined a distinct set of variables conceptualized as legal business creativity, legal-institutional entrepreneurship, and Schumpeterian rule-breaking.