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This exploratory case study investigates a naturally occurring experiment; namely, a high-tech software development startup opening a branch in a rural area in Central Appalachia, employing four young adults as skilled data analysts. Three-step interviews investigate the experiences of the employees, all of whom were living in poverty prior to their new positions, with the goal of understanding how educational experiences impact participation in a new industry. Additional interviews from local residents, youth empowerment programs in the region, and the startup founders located away from the region provide insights into how rural regions might train and prepare youth for technology-based opportunities.