This report examines the core concepts of entrepreneurship and small business, focusing on the essential skills, characteristics, and traits that contribute to entrepreneurial success. It delves into the motivations and mindsets of entrepreneurs, exploring the impact of background and experience on their ventures. The report includes a detailed analysis of successful entrepreneurs, Elizabeth Gooch and Tom Mercer, highlighting their key attributes and how their experiences have shaped their entrepreneurial journeys. It employs the OCEAN model to assess entrepreneurial personalities, covering openness, conscientiousness, extraversion, agreeableness, and neuroticism. Furthermore, the report explores the influence of family background and personal experiences on fostering entrepreneurial spirit and driving business development. The conclusion synthesizes these findings, emphasizing the importance of these qualities for achieving business goals and overall growth. The report includes references to academic sources to support its arguments.