Digital entrepreneurship, often praised as a driver for sustainability, is characterized by substantial “dark sides” that can impede its assumed benefits. This chapter critically explores these adverse unintended effects, focusing on four key areas: (1) rising energy consumption, (2) social inequality, (3) resource depletion, and (4) the concentration of power in the hands of tech giants. Through empirical illustrations, we demonstrate how digital innovations (such as AI, blockchain, and platform-based business models) may exacerbate environmental and social issues. This work calls for a systemic, polycentric approach to digital entrepreneurship, emphasizing the need for balanced governance, social justice, and sustainable energy management. By addressing these challenges, we aim to guide digital entrepreneurs toward a more inclusive and environmentally responsible future, thereby more closely aligning it with the United Nations’ Sustainable Development Goals (SDGs). This chapter serves as both a critical warning and a call to action for scholars, entrepreneurs, and policymakers to rethink the role of digitalization in entrepreneurship for sustainable development.