Resetting Mindsets in Trucking | Larry Long | Ep 20

In this episode of Miles and Mentors, Larry Long shares his journey from business ownership in various industries to becoming a trucking entrepreneur and mentor. With decades of experience in business management and logistics, Larry breaks down the realities of trucking, the pitfalls that cause many owner-operators to fail, and the critical mindset shifts necessary for long-term success.

Larry’s entry into trucking came after years of running businesses, including a successful career in photography. Facing industry changes, he decided to earn his CDL and quickly realized that while trucking offered financial opportunities, most drivers lacked the business acumen needed to succeed. Seeing this gap, he developed a structured approach that focuses on financial discipline, operational efficiency, and strategic decision-making.

After starting as a company driver, Larry quickly transitioned into owner-operator status and then fleet ownership. He specialized in dedicated freight, particularly working with FedEx, and mastered the intricacies of load planning, cost control, and contract negotiation. He explains how these elements allowed him to build a highly profitable operation while avoiding the common financial mistakes that drive many truckers out of business.

A key takeaway from Larry’s experience is the importance of financial literacy. He emphasizes that most failures in trucking aren’t due to a lack of driving skills but rather a lack of financial planning and business strategy. He teaches that understanding cash flow, controlling expenses, and making data-driven decisions are essential for staying profitable—especially in unpredictable market conditions.

Today, Larry runs a mentorship program where he trains new and experienced drivers through an 18-month apprenticeship designed to transform them into successful business owners. His program covers everything from tax planning and expense tracking to customer service and networking. He also consults with current owner-operators struggling to turn their businesses around.

Throughout the episode, Larry challenges common misconceptions in trucking, particularly the blame placed on brokers, fuel prices, and external factors. He argues that success comes from taking full responsibility, optimizing operations, and continuously learning. He encourages truckers to reset their mindset and approach their business like a CEO rather than just a driver.

For those looking to transition from driver to owner-operator or grow a sustainable fleet, Larry’s insights provide a roadmap to financial stability and long-term success.

If you’re starting a trucking business or growing your fleet and need expert guidance, reach out to us today—our industry expert partners can help you make the right decisions for long-term success.