This study explores the effectiveness of experiential learning in teaching generative AI to entrepreneurs and small business owners. The in-person training program, grounded in Kolb's Experiential Learning Theory, aimed to enhance participants' understanding, attitudes, and perceived benefits of AI adoption. Through a structured cycle of Concrete Experience, Reflective Observation, Abstract Conceptualization, and Active Experimentation, participants engaged in hands-on activities with AI tools. The results highlight significant improvements in AI competency, showcasing the potential for experiential learning to reduce perceived technological complexity and drive innovation. This approach provides insights into upskilling entrepreneurs, equipping them with the practical knowledge needed to harness AI for business growth and sustained competitiveness.