Entrepreneurship has evolved significantly across generations, reflecting changes in socio-economic conditions, technological advancements, and cultural values. This study presents a comparative analysis of Gen Z and Traditionalist entrepreneurs, examining differences in mindset, business approach, risk orientation, and performance outcomes. While Traditionalist entrepreneurs are characterized by experience-driven decision-making, long-term planning, and resource accumulation, Gen Z entrepreneurs exhibit digital fluency, innovation orientation, and a preference for agility and experimentation. The research adopts a secondary data-based approach, drawing insights from global entrepreneurship reports, academic literature, and industry analyses. A comparative analytical framework is developed to evaluate key dimensions such as motivation, use of technology, funding patterns, and growth strategies. The findings reveal that Gen Z entrepreneurs leverage digital ecosystems to scale rapidly, whereas Traditionalists rely on stability, incremental growth, and relationship-based networks. However, both groups face distinct challenges that influence their entrepreneurial outcomes. The study contributes to the literature by providing a generational perspective on entrepreneurship and highlighting how evolving economic and technological contexts shape entrepreneurial behavior. The findings have implications for policymakers, educators, and business ecosystems in designing targeted support mechanisms for diverse entrepreneurial cohorts.