Entrepreneurial leadership is a dynamic organizational process that combines grassroots innovation with strategic direction to enable adaptability, innovation, and sustained growth. This article introduces the Four Modes of Entrepreneurial Leadership framework, which helps leaders tailor their approach to the distinct contexts defined by organizational flexibility and resource availability. We define and explore four archetypes: Agile Innovators (flexible but resource-constrained startups and small enterprises), Systematic Builders (resource-rich but structurally rigid corporations), Constraint Breakers (rigid and under-resourced public institutions), and Empowered Pioneers (agile, well-resourced firms with significant growth potential). We highlight how entrepreneurial leaders can apply context-specific tools, ranging from lean startup methods and stakeholder co-creation to strategic abandonment and real options thinking, to align innovation efforts with organizational realities. By matching leadership strategies to structural and resource conditions, this framework offers a practical roadmap for fostering innovation and impact across diverse organizational landscapes.