The Long Haul
The Long Haul
Podcast Description
Adam Wingfield's podcast, "The Long Haul," focuses on assisting small trucking businesses and independent contractors. The show features interviews with industry experts and successful owner-operators, offering advice and strategies for financial success. Its target audience is anyone in the trucking industry, from those just beginning to established fleet owners. The podcast aims to provide actionable insights and encouragement to help listeners improve their businesses. Ultimately, the podcast seeks to connect trucking professionals with opportunities for growth and profitability.
Podcast Insights
Content Themes
The podcast covers various themes related to the trucking industry, including regulatory updates, operational efficiency, and business growth strategies. Notable episodes include a special edition on new CVSA out-of-service rules and interviews discussing efficient scaling strategies with successful truck fleet owners, providing listeners with actionable insights into improving their operations and compliance.

Adam Wingfield’s podcast, “The Long Haul,” focuses on assisting small trucking businesses and independent contractors. The show features interviews with industry experts and successful owner-operators, offering advice and strategies for financial success. Its target audience is anyone in the trucking industry, from those just beginning to established fleet owners. The podcast aims to provide actionable insights and encouragement to help listeners improve their businesses. Ultimately, the podcast seeks to connect trucking professionals with opportunities for growth and profitability.
Every week somebody watches a YouTube video about box trucking and decides it’s their way out.
Non-CDL. Low barrier to entry. Amazon Relay. Home every night. Six figures. The content makes it look straightforward. And for a period of time it was, which is exactly why so many people got in, got humbled, and got out.
Jessica Miller and her husband became owner-operators in 2020. She was an interior designer before that, nothing to do with trucking. They started renting trucks, bought their own, lost them to maintenance, went back to renting, and figured out through trial and error what actually makes a box truck operation work. They’ve cleared over a million dollars in four years running one to two trucks locally in Richmond, Virginia, almost entirely through Amazon Relay.
But this episode isn’t really about Amazon Relay. It’s about the discipline that most carriers never develop, whether they’re running a box truck or a Class A. Knowing your cost per mile. Knowing when to add a truck and when not to. Understanding that revenue is not profit. Staying in a lane that actually makes money instead of chasing a lane that looks good on camera.
The box trucking boom brought a lot of people into this industry who had no business being here. Jessica has a front-row seat to what that did to Amazon’s requirements, to local freight rates, and to the reputation of an entire segment of the market. That’s the conversation worth having.

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