Small businesses play a critical role in economic development. Over the past 20 years, policies and programs have sought to increase the potential success of these businesses. Yet little is known about the extent to which these policies and programs respond to the specific needs of business owners. Using a mixed-methods approach, the authors investigate the barriers to success that small business owners face, the effectiveness of current policies and programs aimed at serving small businesses, and ways to improve the current system. Focusing on disadvantaged entrepreneurs in New York City, the authors find five primary gaps within the current policy system: a transitional gap, an information gap, and an institutional capacity and service delivery gap. The authors argue that the capital and training needs of small business owners are deeper and more complex than what the current policy system addresses and offer recommendations for improvement.