Entrepreneurship is essential to Indonesia's economic development. It is evidenced by 99.9 percent of all Indonesian firms are micro, small, and medium-sized enterprises (MSMEs). Entrepreneurship is regarded as a phenomenon that has received the greatest attention in recent years. Among scholars, there is a strong desire to investigate the entrepreneurial phenomena not only because of its unavoidable importance in boosting the economy and creating job possibilities. Young generations play an essential part in entrepreneurial ventures since they are more likely to start a new business than older generations. However, research studies found Gen Y and Gen Z have different characteristics, which leads to differences in entrepreneurial orientation. The study successfully collected the primary data from 389 newbie entrepreneurs who distributed closed-ended questionnaires using a 5-point Likert scale. This study adds significantly to the existing entrepreneurial literature by examining entrepreneurial orientation between these two generations based on three dimensions: innovativeness, proactiveness, and risk-taking. In addition, the Rasch model was used in this study. The study's outcomes demonstrate a significant difference in risk taking dimension between gen Y and gen Z. Practical implications based on this research of entrepreneurial orientation among the two generations can be empowered through entrepreneurial education programs. The study provides the recommended methods to develop each gen Y and gen Z entrepreneurs.