Based on case studies of top senior leaders (vice-chancellors) of Malaysian public universities, this chapter explores the characteristics of challenging experiences they encountered that require them to embrace entrepreneurship in their leadership. The complexity of diverse stakeholders, the multiplicity of academic disciplines, the lack of familiarity leading different and broader roles, leading in new directions, and creating change in high velocity and uncertain environments are among the entrepreneurial situations that characterize institutional adversities. Learning agility, opportunity recognition, and bridging capability are among their exemplary entrepreneurial leadership competencies in the face of adversity. This chapter concludes that entrepreneurial leaders in public universities as those leaders capable of bridging the gap between diverse stakeholders to achieve a unified vision of innovative public value creation and dynamic education marketplace adaptation.