The advent of the Fourth Industrial Revolution has marked a profound shift in the global economy, driven by the integration of artificial intelligence (AI), the Internet of Things, and quantum computing. AI stands out as a transformative force, profoundly reshaping industries, labour markets, and economic interactions. Also, AI’s widespread implementation generates both opportunities and disruptions, with forecasts of the displacement of millions of jobs and the creation of new roles. However, these transformations vary significantly across regions and demographics, with countries like Italy facing unique challenges, including a substantial digital skills gap among the working population. Despite the growing interest in AI’s technological and economic implications, limited research has investigated how specifically entrepreneurs adopt and utilise AI technologies in their daily business practices. While existing literature has focused predominantly on sector-specific applications—most notably in healthcare—entrepreneurship as a dynamic and multifaceted phenomenon remains underexplored in this context. Indeed, our study investigates how entrepreneurs adopt AI into their professional routines, the digital competencies they display during this process, and the learning ecosystems that support their acquisition of AI-related knowledge. To reach our research aim, we adopt a qualitative approach, conducting semi-structured interviews with a sample of entrepreneurs operating in Southern Italy. Through thematic analysis, we aim to highlight the existing patterns of AI adoption and the support mechanisms within the entrepreneurial ecosystems. The findings contribute to a deeper understanding of the AI adoption for entrepreneurs and their main digital competencies gap, offering theoretical insights and practical implications for policymakers, educators, and innovation stakeholders.