Skateboarding, widely popular and often misunderstood, occupies a unique space in US society. Despite skateboarding's popularity little is known about the effects of skateboarding on youth and their educational and career trajectories. This report outlines the current landscape of skateboarding at this socio-historical moment in time--prior to skateboarding's debut in the 2020 Olympics. The authors describe this study's approach to learning more about skateboarders in U.S. society. This report is the first step in a multi-phase study funded by the Tony Hawk Foundation and conducted by researchers from the University of Southern California's (USC) Pullias Center for Higher Education and Annenberg School for Communication and Journalism. The study explores how skateboarders between the ages of 13 and 25 viewed their skill sets and examined the implications skateboarding has on their education and careers. The study design centers on youth who are passionate about skateboarding--including skateboarders who integrated into thriving skateboard communities and those who might feel disenfranchised from the skateboard community or the community at large. By gaining a deeper understanding of the complexity of skateboard ecosystems, research findings aim to inform skateboarding scholarship and practice. [Funding for this project was provided by the Tony Hawk Foundation. This report was co-produced by the USC Annenberg School for Communication and Journalism.]