This report delves into the core aspects of entrepreneurship, examining the characteristic traits and skills of successful entrepreneurs, such as passion, strong work ethics, communication skills, determination, and competitiveness. It explores how aspects of entrepreneurial personality, including extraversion, agreeableness, conscientiousness, emotional stability, and openness to experience, reflect entrepreneurial motivation and mindset. The report investigates different perspectives on entrepreneurial characteristics, including optimism, action orientation, and risk-taking, while providing detailed analyses of traits, skills, and motivational drivers through examples of local, global, and social entrepreneurs like Daw Khin Khin Gyi, Alon Braun, and Bill Drayton. Furthermore, it evaluates the influence of background and experience on entrepreneurial ventures, highlighting both positive and negative impacts, and links entrepreneurial characteristics to the backgrounds of successful entrepreneurs. The report concludes with a critical evaluation of how background and experience shape entrepreneurial outcomes, supported by specific examples.