Small business managers often lack the leadership skills necessary to sustain their businesses beyond 5 years. The United States Small Business Administration reported that more than 65% of small business owners, including home health care agency managers, fail within the first 5 years of operation. Guided by Burns and Bass's transformational leadership theory, this multiple case study explored leadership skills that managers in home health care agencies need to sustain their new businesses beyond 5 years. The purposeful sample comprised of 3 managers from 3 different home health care agencies within a 75-mile radius of Baltimore, Maryland, that had demonstrated success in surviving past 5 years. Semistructured interviews, agencies' quality assurance plans and policies were reviewed, and procedural documents related to leadership skills were gathered as data. Yin's 5-step data analysis technique was used to identify key themes. Member checking enhanced the credibility of data interpretation. Themes that emerged from data analysis were business management, knowledge and performance, and transformational leadership. Study findings may contribute to positive social change by providing practical guidance to home health care managers, which may improve their agencies' viability and delivery of patient care. Business implications include the provision of long-term employment to workers and safety assurance to patients' families.