This study explored how online teacherpreneurs, or preschool to twelfth-grade teachers who market their classroom materials online, experience perceived improvements to classroom practice. Research has found that participating teachers believed teacherpreneurship motivated them to try unique classroom approaches, exposed them to new ways of thinking about education, and prompted pedagogical innovation. However, the factors influencing these reported teaching benefits were not explained. In this study, survey data from 226 TeachersPayTeachers.com (TpT) sellers were analyzed to understand what factors, if any, affected teacherpreneurs’ perceived teaching gains. Ordinary least squares regression and dominance analyses indicated that teaching gains were significantly predicted by collaborating with teachers, acting as a teacher leader, and taking part in enterprising actions. This was more evident for females, those without postgraduate degrees, and those with the most experience selling on TpT, respectively.