The researcher explored the reasons why only 50% of new small businesses survive five or more years with the goal of determining the characteristics that led to success. This qualitative study focused on small business success with the purpose of exploring the life and career experiences of a select number of small business owners in a metropolitan area in the Southeastern United States. The conceptual framework and research design were based on Duckworth’s grit theory, Dweck’s growth mindset theory, Garmezy’s resilience theory, and Bandura’s self-efficacy theory. These theories were interconnected with transformation leadership theory as defined by Bass & Riggio (2006), Kouzes and Posner (2017), and Burns (1978). This study also explored the perceptions of small business owners regarding the most and least important personal characteristics needed to run a successful small business. The Seidman model of interviewing in a series served as the approach for data gathering. This approach included the following activities the researcher collected participant data using a series of interviews, observations, memos, field notes, and document analysis. Due to the COVID-19 pandemic that began in 2020, the research was adapted to identify changes required for small business owners to survive through a pandemic and qualities embedded in their lives before it began. Future recommendations include: conducting quantitative and mixed methods studies on small business success, using a larger participant pool, and conducting a longitudinal study to continue building best practices for success. Keywords: small business success, small business owner, entrepreneurship, leadership, pandemic, resilience