Entrepreneurs and their ventures are often portrayed as unambiguously positive forces in society. Specifically, high technology and equity-funded startups are heralded for their innovative products and services that are believed to alter the economic, social, and even political fabric of life in advantageous ways. This chapter draws on established theory on the causes of misconduct in and by organizations to elaborate the factors that can give rise to misconduct in entrepreneurial ventures, illustrating our arguments with case material on both widely known and less well-known instances of entrepreneurial misconduct. In venturing into the dark side of entrepreneurship, we hope to contribute to theory on entrepreneurship and organizational misconduct, augment entrepreneurship pedagogy, and offer ideas and examples that can enhance entrepreneurs’ awareness of their susceptibility to wrongdoing.