Although dual career research has received growing attention, there is a lack of research specifically focusing on whole dual career development environments (DCDEs). The overall aim of this study was to provide a thorough insight into a DCDE with two main objectives, as follows: (a) provide a holistic description of a DCDE and connections within the environment and (b) examine factors influencing the environment’s success in supporting student-athletes’ development. The data analysis and collection were guided by recently developed DCDE and dual career environment’s success factors (DC-ESF) models. The data were gathered from multiple perspectives via interviews, informal discussions, and observations to analyze a real-life setting and its everyday processes. The authors found that the school’s dual career philosophy was aimed toward supporting holistic growth development via communication, feedback, and flexibility. The main success factors contributing to the environment’s success were placing importance on effort and task-related focus in everyday activities, being flexible, reinforcing openness, and developing responsibility in student-athletes. Furthermore, providing a systematic daily schedule, establishing systematic information sharing, and organizing a variety of school events contributed to the development of planning, and time management, resilience, effort, and communication skills in student-athletes represented factors of success. These findings are presented in two empirical models (DCDE and DC-ESF) of the Audentes Sports Gymnasium.