Potential entrepreneurs seek to learn about the startup and success process from respected and successful entrepreneurs as role models. This paper presents 16 types of role models based on entrepreneurial career models. In the research process, 30 successful role model entrepreneurs from Korea and abroad were selected, and case studies based on in-depth interviews and various secondary data were conducted. Through this approach, the study aimed to reveal that different types of entrepreneurial career models exist and to identify their respective characteristics. The entrepreneurial career process was viewed as progressing through four career stages: The first is the study stage, a period for cultivating the skills and competencies necessary for starting a business. The second stage is the startup stage, where one actually launches a business based on what was prepared. The third stage is the success stage, where desired achievements in business are attained through innovative products in the market. The fourth stage is the significance stage, where one explores social roles based on one's success. This entrepreneurial career model was developed based on existing traditional career stage models and firm growth stage theories, because unlike traditional careers, the nature of an entrepreneur's career changes according to the progress of the business they build. By dividing each of the four entrepreneurial career stages (4S) into two entrepreneur types, a total of 16 role model types were presented. This approach borrows from the MBTI methodology used in psychology for classifying personality types. Ultimately, the study aimed to provide the decision-making issues and implications that successful role model entrepreneurs contemplate at each career stage. The entrepreneurial career stage model and role model typology are believed to contribute to helping potential entrepreneurs select role models that match their own profiles and consider the issues to bear in mind at each stage of the process. Furthermore, by considering the characteristics, advantages, and disadvantages of each type, the likelihood of success can be further enhanced. Since the 16 types of entrepreneurial career models illustrate the careers of different successful entrepreneurs, they can serve as a reference for policymakers and educators seeking to inspire entrepreneurship when designing support policies and educational programs. This implies that because the ways entrepreneurs prepare and achieve success are diverse, more sophisticated support infrastructure must be established. From an academic perspective, this study can be viewed as a starting point in that it introduced the research topic of entrepreneurial career—a subject not previously addressed in the field of entrepreneurship and overlooked in traditional career theory research—and proposed a foundational research framework through exploratory case studies.