Many barber salons and other small businesses in the United States fail to succeed beyond the first 5 years. The factors responsible for the low survival rate of salons may include the limited training and education levels mandated by state certification requirements. The purpose of this multiple case study was to identify business strategies successful barber salon owners use to overcome the business management and staffing challenges associated with a small pool of skilled barbers and the high turnover in a low wage profession. The theory of transformational leadership served as the conceptual framework. The data collection included interviews of 3 successful barber salon owners who met the study participation eligibility criteria of licensed, registered, operating a salon business in the Indiana region for more than 5 years, and over the minimum age of 25 years. The 4 themes emerging from the interview data analysis were (a) barber salon operating structures, (b) salon leadership and managerial strategies, (c) licensed barber skill enhancement, and (d) salon operating strategies effectiveness and sustainability. The data analysis also involved the triangulation of the primary research against secondary data from the Small Business Administration and barber industry reports. The expertise and knowledge shared by the interviewees could serve the quest of barber salon businesses in the Indiana region to overcome the profitability and financial sustainability challenges of this industry. The study findings may potentially contribute to positive social change by improving the economic standing and welfare of barber salon owners and professionals in the community.