This study aims to explain the legalistic entrepreneurship by introducing the type of legalistic entrepreneurship that transforms compliance with laws into entrepreneurship action, and answer the question of how information and communication facilities brought by the digital world can be turned into opportunities in the face of legal obstacles. In this chapter, the concept and components of legalism, the conceptual framework of legalistic entrepreneurship, processes, personal characteristics of legalistic entrepreneurs are explained. In the conclusion section, recommendations are made to policymakers, entrepreneurs, and academicians on virtual commerce and initiatives to be developed in the digital environment and legalistic entrepreneurship.