Entrepreneurship is a crucial ingredient of economic growth and job creation. Small business start-ups are currently of great interest to many state and local governments including Indiana. With the growing need to stimulate small business development, it is necessary to understand the obstacles faced by entrepreneurs as they attempt to start a business. The results have implications for small business development and university related centers and how they design programs to effectively meet the needs of entrepreneurs participating in small business start-ups. More explicitly, the results show that targeting educational programs by socio-economic and demographic segments would have lead to a better chance of programming success