U.S. Small Business Administration reports that small businesses are one of the pillars of the U.S. economy, providing employment, innovation, and productivity. However, these businesses are constantly faced with challenges resulting from limited resources and continuous technological advances. This qualitative multiple-case study was performed to explore the strategies that small business owners (SBOs) in Maryland use to acquire capital to sustain their businesses financially for more than 5 years. The study's framework, the strategic management theory, was applied to determine the most effective approaches for the small businesses. Face-to-face interviews with 6 recruited SBOs were performed. A qualitative thematic analysis was then used to analyze the interviews. The main strategies to sustain capital were to create a business plan focusing on long-term goals and invest in employee knowledge and skills. In the process of measuring success, participants mostly determined their success by their ability to acquire customers based on feedback and good service. The interviewees managed their cash by minimizing debt, maximizing the use of technology, and keeping track of cash flows. The SBOs also shared that the challenges in business were endured by staying debt-free, adjusting their strategies with the market changes, and conserving cash and expenses. Contributions to social change include helping small businesses sustain by leveraging strategic planning, management, and implementation in their businesses, thereby providing jobs and contributing to the overall economic vitality of the community.