Disruptive Innovation, according to the term’s founder Clayton Christensen, is defined as a specific type of innovation that is able to capture the lower-end of the market through quality, feature, or cost differences and leverage this position to achieve higher market share. Entrepreneurs who utilize disruptive innovation strategies have been historically able to create products and services that achieve massive financial and cultural success. Theories of personality characteristics have been previously applied to entrepreneurial activities, but not used to bridge the gap between developmental experiences and market success. Cross-industry analysis of ten top entrepreneurial business leaders from retail, food services, and consumer electronics allows for the identification of certain personality characteristics and influences present in the early lives and careers of highly successful entrepreneurs. Entrepreneurs can be categorized according to inherent skills and personality characteristics, which suggest either revolutionary or architecturally brilliant product or service creation. Patterns of conceptual product ideation and business model evolution show that there are similarities between experiences in an entrepreneur’s formative years and the implementation of a business model and strategy. Implications of highly successful business models as they relate to marketplace dynamics include financial success, cultural impact, and institutionalization. To varying degrees, disruptive entrepreneurs are able to institutionalize their business concepts in order to ensure lasting success in their respective marketplaces.