The well-being of the United States economy is substantially interwoven and impacted by the performance of small business enterprises (SBE). New SBEs fail at a rate of 75% during their first year. Numerous predictive failure models identified factors such as lack of experience or underfunding are as root causes of failure however these are only symptoms and not root-causes. Most SBEs performance outcome - failure or success - can be traced to specific decisions, or lack thereof, of the entrepreneur. The specific problem explored in this study was how the attitude, thought processes, perception, intention and behavior of five Successful Entrepreneurs (SE) and five Failing Entrepreneurs (FE) affected their business outcomes. Through a qualitative multi-case study and cognitive interviews, the entrepreneurs’ attitude, thought processes, perceptions, intentions and behavior were explored. All participants operated businesses within south Florida’s Tri-County boundaries, for less than ten years.