In the United States, small businesses have a high failure rate, with approximately 50% going out of business during the first 5 years. The purpose of this multiple case study was to explore strategies small business owners in the mid-Atlantic region of the United States used to stay in business for more than 5 years. Entrepreneurship theory provided the conceptual framework for the study. A sample of 5 small business owners participated in semistructured face-to-face interviews, and additional data were collected from field notes, observations, and review of artifacts related to small business success and longevity. Data were analyzed using Yin's 5 stages of coding to reveal 4 themes: solve a problem, ensure start-up money, address marketing, and provide great customer service. Proper planning that addressed all 4 themes was the most important leadership strategy to sustain small businesses beyond 5 years. The results of this study might bring about positive social change by helping small business owners to ensure business growth, increase revenues, stimulate job creation, foster social unity, and promote local economic stability.