This paper explores the influence of GenAI chatbot (ChatGPT) and AI-based simulation (SimVenture) on the start-up intention through the mediating roles of entrepreneurship educational outcomes; entrepreneurship cognition, entrepreneurship competencies, and innovation spirit of students in higher education institutions in the Middle East. The proposed conceptual framework was empirically tested with partial least squares structural equation modeling using 166 survey responses from fourth-year undergraduate students enrolled in business administration programs in four higher education institutions in the Middle East region. The findings reveal that ChatGPT significantly promotes start-up intention, while ChatGPT has insignificant influence on entrepreneurship educational outcomes. Conversely, the SimVenture platform negatively influences start-up intention. Additionally, the SimVenture platform significantly improves entrepreneurship educational outcomes; thereby entrepreneurship educational outcomes directly influence start-up intention. Furthermore, the mediation paths show ChatGPT has an insignificant indirect influence on start-up intention through the mediating roles of entrepreneurship educational outcomes, while the SimVenture platform exhibits a notable indirect influence on startup intentions through improved entrepreneurship educational outcomes. These findings seek to provide insights for higher education institutions in the Middle East region in leveraging GenAI chatbot (ChatGPT) and AI-based simulation (SimVenture) to enhance entrepreneurial knowledge, awareness, competencies, and the spirit of innovation, which leads to promoting students’ intentions to start their businesses. Theoretically, the study contributes to filling the gap in the existing literature between AI tools and entrepreneurship education. This study is among the first to empirically explore the influences of GenAI chatbot (ChatGPT) and AI-based simulation (SimVenture) on entrepreneurship educational outcomes and the intention of students to embark on entrepreneurial ventures. It highlights the need for understanding AI technologies as distinct pedagogical tools.