Providing teachers with innovative teaching approaches that combine simulation-based learning systems with entrepreneurship education helps create and recognize entrepreneurial opportunities. In this study, key antecedents are identified as critical drivers of flow experience and the impact of flow experience on learning performance and entrepreneurial self-efficacy is examined in order to propose a behavior model based on flow theory. Virtual Business Retailing (VBR) software, a business simulation system for convenience store operations, is used in this study to investigate the learning behavior of students and to collect data for analysis. The results reveal that challenge-skill balance and playability play a critical role in enhancing flow experience and, consequently, in improving learning performance and entrepreneurial self-efficacy. The findings contribute to existing flow theory, the literature on simulation and game-based learning, and the literature on entrepreneurship education. Furthermore, the findings provide VBR education-system educators and developers with a better understanding of students' expectations and needs when interacting with retail business simulation-based learning environments as well as with guidelines to effectively design VBR educational systems that are conducive to flow experience, which may help improve entrepreneurial self-efficacy in students.