In this episode of Chess Not Checkers, hosts Keith Riddle and Jordan Tampien sit down with entrepreneur Jason Boudreau to discuss his incredible journey from personal hardship to building a successful business empire. Jason shares how he went from struggling on a friend’s couch to running Drive 509, a trucking school, and developing a software solution that has transformed the CDL (Commercial Driver’s License) training industry.

Jason offers insight into his entrepreneurial journey, emphasizing the importance of resilience, adaptability, and a willingness to learn from failure. He discusses the challenges he faced in starting his trucking school with limited resources, and how his innovative spirit led him to create CDL Power Suite and ELDT.com—tools that are now helping thousands of students and schools nationwide.

The conversation also delves into Jason’s vision for personal and professional growth, focusing on the importance of building people—not just businesses. He talks about fostering a culture of learning, mentorship, and self-improvement, and how these values have driven both his personal success and the growth of his business.