Entrepreneurial success is influenced by a complex interplay of personality traits and contextual factors. This chapter examines the role of personality in shaping entrepreneurial outcomes through the lens of machine learning (ML). Drawing on established frameworks such as the Big Five, HEXACO, and the Dark Triad, it highlights how traits like openness, conscientiousness, and extraversion contribute to opportunity recognition, risk-taking, innovation, and team effectiveness. The chapter explores ML approaches—including supervised learning, unsupervised learning, natural language processing, and deep learning—to model trait-outcome relationships and generate predictive insights. Practical applications for entrepreneurs, investors, and educational programs are discussed, alongside ethical considerations such as bias, privacy, and interpretability. Future directions emphasize multimodal, longitudinal, and culturally sensitive models.