Small business owners struggle to sustain their businesses over time. According to U.S. Census data in 2014, only half of all small businesses survived beyond the first 5 years of operation, and only a third survived longer than 10 years. Grounded with the strategic contingency theory, the purpose of this multiple case study was to explore strategies small service business owners used to succeed beyond the first 5 years of operation. The target population consisted of 4 owners of small service and retail businesses in Arlington, VA, with fewer than 50 employees who have succeeded in business longer than 5 years. Through a process of methodological triangulation, data collected from financial documents, publicly available records, and external sources supplemented semistructured interview data. Using thematic analysis by coding narrative segments, 3 themes emerged including developing a unique marketing strategy, developing strategic leadership skills, and required business skills for sustainability. Successful unique marketing strategies emerged from understanding customer needs. The results from this study could benefit business owners by improving business success rates, which would have a positive economic effect on local community, including job creation, and sustainable economic stability. The implications for positive social change might include the reversal of small business failure trends through the application of successful business strategies.