Small Business Administration statistics indicate that 20% of small businesses fail within the first 2 years and 50% fail within 5 years. The purpose of this case study was to explore the success factors and strategies of 12 small business owners of independent financial planning firms who achieved profitability beyond 5 years. The conceptual framework was entrepreneurship theory and Porter’s five forces model of competitive strategy. The data gathering method included semistructured interviews and analysis of business artifacts such as websites and newsletters. Initial coding of the responses preceded an analysis of recurring patterns and themes. The major themes identified were: technical training is necessary but not sufficient for success; planners need training in business creation, operations, and marketing; differentiation is important and is achieved by specialization. Developing internet websites proved to be the most effective approach to attract new clients. These results provide information to people considering starting or maintaining a small business, providers of professional education and training, and business leaders seeking to improve recruitment and retention of financial planning employee retention. Implications for positive social change include providing information to policymakers who seek to support small businesses to mitigate small business failure rates, expand job creation, and provide sources for financial guidance for American employees.