Entrepreneurial ways of thinking and doing intersect with the knowledge and skills that a global citizen needs to thrive. There is a robust body of scholarship that identifies core entrepreneurial skills however there is a dearth of evidence addressing how to successfully teach entrepreneurship. Using the lens of experiential learning, this qualitative study examines the surface, deep, and implicit structures of professional entrepreneurial culture toward revealing a meaningful, authentic pedagogical approach for entrepreneurship education. In order to achieve this outcome, researchers utilized a semi-structured comparable multiple-case study design to engage 19 incubated entrepreneurs in focus group interviews. A replication strategy to inductive qualitative analysis was employed toward cross-case analysis. Findings revealed that incubated entrepreneurs routinely engage in a wide variety of transdisciplinary experiences characterized by cycles of success and failure. Additionally, face-to-face interactions that are grounded in a network of trust were revealed to be a vital part of the entrepreneurial process. Thus, pedagogies anchored in the design process would provide an authentic, experiential context in which to prepare future entrepreneurs. Implications for elementary and secondary educational approaches are discussed.