Typically, small businesses have encountered issues with sustaining their enterprise for longer than 5 years after inception, which can adversely affect the prosperity of the communities in which the businesses operate. The purpose of this multiple case study was to identify and explore strategies some owners of small business trucking companies used to achieve profitability and longevity for longer than 5 years. The population of the study consisted of owners of 4 small business trucking companies located in Northern Virginia, who demonstrated profitability and longevity for longer than 5 years of operation. The conceptual framework for this study was systems theory. The data for the study came from semistructured interviews, and review of companies' documents. The data analysis process consisted of organizing the data, interpreting the data, and identifying the themes. After verifying the themes through methodological triangulation, 3 themes emerged: relationship building, passion and commitment, and access to capital. The findings, conclusions, and recommendations from this study could effect social change by providing profits to the small business trucking owners for sustaining and aiding employees, families, and their communities' economies.