Entrepreneurs have a critical role in the growth of an economy, particularly in an emerging market such as the Association of Southeast Asian Nations (ASEAN). As a member of ASEAN, Singapore has faced increasing competition from its emerging Asian rivals. However, it has still managed to retain its position among the top countries for competitiveness and innovation. The encouragement of entrepreneurship is a major policy initiative of the Singapore Government at all levels. While there is a clear emphasis and a desire for entrepreneurial activity, small businesses and/or entrepreneurial ventures have demonstrated sizeable failure rates because the idea of entrepreneurship was not accepted in most organisations. Entrepreneurship has confronted several challenges for Generation Y entrepreneurs in Singapore, which has influenced their businesses in general. This book will also use generational theory to explain why Generation Y entrepreneurs are different from all the other generations. Generational theory is founded on the individual%u2019s experiences that are influenced by the historical events and living conditions when he was born and while he was growing up. As individuals grow up, their experiences result to a unique set of shared beliefs and values (Giancolo 2006). Based on their individual experiences, most people from a generation view the world and filter information through their own generational lenses (Seaton & Boyd, 2007). This development of personality traits was formed based on the experiences they had during their formative years. This book wanted to explore the Generation Y cohort in terms of their lived experience towards the entrepreneurial journey in Singapore. The different sections in the book showed that Generation Y entrepreneurs are different. This qualitative phenomenological approach examined the Generation X and Y cohorts in terms of their lived experience towards the entrepreneurial journey in Singapore, which can consequently fill empir