The results of small business operations play a significant economic role in developed economies, yet in the United States, approximately 50% of small businesses fail within the first 5 years of operation. Some small business owners embark on small business initiatives without the cash management strategies necessary to sustain their businesses. Grounded on financial literacy theory, this multiple-case study identified the strategies that owners of small businesses used to manage cash in their daily operations. The population included 3 owners of small tavern business in southeast Alaska who have implemented cash management strategies. Data were collected from semistructured interviews, supplementary documentation, and reflective journal notes. Data were analyzed using methodological triangulation, coding, and thematic analysis. Three themes emerged from data analysis: cash management capabilities, internal controls and employee accountability, and cash management opportunities. The findings of this study may contribute to positive social change by improving the ability of leaders of small businesses to increase job availability and contribute to economic stability in communities, thereby improving local and regional economies and enhancing the standard of living for individuals and households.