Entrepreneurship is associated with high levels of stress, challenges to resilience, and risk of burnout, which can adversely affect both personal well-being and venture performance. Traditional assessment methods, such as surveys and self-reports, are often reactive and insufficient to capture dynamic psychological changes. This chapter explores the application of artificial intelligence (AI) and predictive analytics in monitoring and mitigating stress and burnout among entrepreneurs. It highlights theoretical foundations, measurement approaches, and AI-driven interventions that integrate physiological, behavioral, and communication data. Ethical, privacy, and practical considerations are discussed, alongside real-world case studies demonstrating AI's potential for proactive, personalized support. Future research directions emphasize multi-modal models, longitudinal tracking, and explainable AI. Overall, AI offers a transformative opportunity to enhance entrepreneurial resilience, well-being, and sustainable performance.