289: Forty Years on the Road: Why Getting Your CDL Is Still One of the Best Careers in America
This week on the Oakley Podcast, Jeremy Kellett sits down with long-time Oakley owner-operator Tim Drake to talk about his life in trucking, from growing up in a trucking family and starting with a chauffeur’s license before CDLs, to running his own 379 Peterbilt with over 1.6 million miles. Tim shares how he transitioned from flatbed to Oakley, why he stuck with pneumatic tanks, and how careful maintenance and money management helped him pay off his truck and weather tough times. He opens up about the sacrifices of being away from family, the importance of saving for breakdowns and retirement, and the changes he’s seen in the industry, including regulations, technology, and distracted driving. Along the way, Tim talks about his passion for motocross at 57, the value of a CDL as a lifelong career option, and offers practical advice to younger drivers on working hard, living within their means, and taking care of their health and safety on the road.
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