The Long Haul

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...

Diesel just crossed $6.29 per gallon nationally. For the first time in history. That's not a headline to scroll past. That's a number that should stop every owner-operator and small carrier in this industry dead in their tracks and force them to look at their actual cost structure right now — today — before they take another load. Because most of them haven't. This episode is a solo. No guest. Jus...

Every load you've ever picked up from a warehouse got there somehow. Somebody moved it from a ship. Or from a rail yard. Or from a port depot. On a chassis. In a container. In a city like Chicago where the rail network is one of the most complex in the country and the congestion, the chassis shortages, and the steamship line politics can turn a straightforward pickup into an all-day event. That's...

Josh Lovan has seen how trucking companies die. Not slowly, from rates. Fast, from one crash. Before he became an advisor at J. J. Keller, Josh was Director of Safety and Security for a major carrier — the man in the room when the accident call came in, when OSHA showed up, when the lawyers started prepping for trial. He's sat in the depositions. He's watched a single wreck, with shared fault and...

There's a pitch aimed at truckers on every platform right now. Brokers are eating your margin. Cut out the middleman. Get your own authority. It's not hard — you just need a mentor. And there's always a mentor selling. Trent Tulloh is one of them. He runs Forever Freight Broker, a Tampa training company that teaches drivers and dispatchers to become freight brokers. His reason is personal — his fa...

Greg Feary runs the most powerful transportation law firm in America. Scopelitis represents the nation's largest trucking companies — when a mega-fleet gets sued, there's a good chance his firm answers the phone. He's spent four decades watching carriers get dismantled in deposition rooms, and prepping them to survive it. So I asked him to do something no guest has done on this show. Depose me. Mi...

On May 14, the Supreme Court handed down one of the biggest trucking decisions in a generation — and most small carriers still haven't heard about it. Montgomery v. Caribe Transport. Nine to zero. Freight brokers can now be sued in every state in the country for negligently selecting an unsafe motor carrier. The federal shield that protected them for years is gone. Every headline called it a broke...

Most carriers think their recruitment problem is a marketing problem. Post the ad. Get the calls. Fill the seat. Move on. Christian Martinez has managed over 65 owner-operators at Voyager Nation out of Mulberry, Florida — and he'll tell you straight up that recruitment is the easy part. The hard part is everything that comes after somebody signs on. He started at the bottom. Loading trucks. Wareho...

Jerry Murphy has a felony on his record. He was a raging alcoholic — his words, not mine. Working part-time to drink full-time. He had his own motorcycle shop once and drank it into the ground, and he'll tell you straight up whose fault that was. Then he got sober. Six years now. He built a trucking company out of Circleville, Ohio from two trucks scraping by on the load board into an operation hi...

Debon Sims — DJ — got his CDL in 2018 and bought his first semi-truck in 2019 after getting out of a lease-purchase program. What the intake form doesn't say is what came before that. DJ has been incarcerated. He knows what it feels like to have the system count you out. He also knows what it feels like to decide that the count doesn't matter. He landed an Amazon contract early on. Lost it. Spent...

Factoring might be the most argued-about topic in small carrier Facebook groups. Half the comments say it saved their business. The other half say it nearly destroyed it. And everybody's got a story about a contract they didn't read closely enough, a reserve they couldn't get back, or a fee they didn't see coming until it was too late. The frustration is real. And it's earned. But here's the part...

Thousands of people enter trucking every year looking for a better future. Many are chasing freedom. Some are trying to build wealth. Others are leaving careers they have spent decades building in hopes of creating something of their own. Some make it. Many don't. In this episode, Adam sits down with Victor "Bigg Vic" Newton, founder of Bigg Vic TV and one of the most recognized voices in trucking...

Military freight is one of the most misunderstood corners of trucking. Most owner-operators hear about Department of Defense freight and immediately assume: it’s impossible to access, only big fleets can get it, or the system is too complicated to understand. But the reality is deeper than that. In this episode of The Long Haul Podcast, Adam sits down with Philip Nenadov, CEO of Military Freight C...

Most trucking companies don’t fail because freight disappears. They fail because cash flow breaks first. In this episode of The Long Haul Podcast, Adam sits down with Michael Bunton to discuss one of the most overlooked realities in trucking:cash flow management. Michael’s background is unique — from professional baseball with the Chicago Cubs organization to human performance coaching before ente...

Everybody wants somebody to blame. Brokers. ELDs. Immigration. Mega carriers. The government. The spot market. But what if the problems facing trucking today go much deeper than social media talking points? In this episode of The Long Haul Podcast, Adam sits down with Stephen Ruhe — third-generation trucking operator, Navy veteran, brokerage leader, and trucking history enthusiast — to break down...

Many small carriers think they have a driver problem. They don’t. They have a messaging problem… a positioning problem… and a clarity problem. In this episode of The Long Haul Podcast, Adam sits down with Elijah Cramer — who built his career inside driver recruiting before moving into tech and working directly with carriers to improve hiring and retention This conversation breaks down: Why driver...

Everyone wants to own a truck. Very few understand what comes after. In this episode of The Long Haul Podcast, Adam sits down with Pamela Polyak — a third-generation transportation owner who took over her family’s asset-based operation at the start of 2020 and has spent years helping small carriers navigate compliance, operations, and growth This conversation breaks down: Why most new authorities...

Most small carriers believe they’re compliant. Until they’re not. And by the time they find out… it’s already too late. In this episode of The Long Haul Podcast, Adam sits down with Brandon Wiseman of Trucksafe & Childress Law, a legal expert with nearly 20 years of experience in DOT safety, compliance, and accident exposure. This isn’t a surface-level compliance conversation. This is about what a...

In this special on-location episode of The Long Haul, host Adam Wingfield takes listeners directly onto the floor of the 54th Annual Mid-America Trucking Show (MATS) in Louisville, Kentucky. Recorded from within the exhibits and custom trailers that define the industry’s biggest event, this episode moves past the equipment to focus on the "human element" of trucking. Follow The Long Haul Podcast O...

In this episode of The Long Haul, Adam Wingfield sits down with Jorge Rivera, a longtime truck driver and DACA recipient caught in the middle of a growing regulatory battle. As new rules around non-domiciled CDLs take center stage, Jorge shares how drivers like him—fully vetted, experienced, and deeply rooted in the U.S.—are being unintentionally pushed out of the industry. From viral moments and...

In this special edition of The Long Haul, live from the Mid-America Trucking Show (MATS) 2026, host Adam Wingfield sits down with Ilya, the founder of ICV Express, to discuss a masterclass in trucking resilience and unconventional strategy. Ilya shares his unique transition from the high-pressure world of the restaurant industry—where he managed kitchens at Chipotle and opened fast-casual brands i...

Every year thousands of drivers and trucking companies head to the Mid-America Trucking Show (MATS) in Louisville, Kentucky. And every year… most of them make the same mistake. They spend three days looking at custom trucks, collecting free hats, and walking the floor without a plan. But for small carriers and owner-operators, MATS can be one of the most valuable business opportunities of the enti...

Cargo theft is evolving — and most small carriers aren’t prepared for it. In this episode of The Long Haul Podcast, Adam sits down with Jillian Kossman, Chief Operations Officer at IDScan.net, to break down one of the fastest-growing threats in logistics: identity fraud and fictitious pickups. Modern fake IDs are no longer obvious — and many small carriers, brokers, and shippers simply don’t have...

Freight markets are sending mixed signals right now. Spot rates are ticking up. Tender rejection pockets are appearing across the country. Port volumes are surging in some areas. But underneath those numbers, the broader economy is flashing warning signs. Credit card debt has reached a record $1.28 trillion. Unemployment among college graduates is rising. Consumer spending — especially in big-tick...

Truckers are sold to 24/7 — by brokers, shippers, insurance companies, fuel programs, tech apps, dispatchers, and every “solution” in the industry. But here’s the truth most won’t say out loud: small carriers aren’t failing because they don’t know how to drive… they’re failing because they’re misinformed, misled, or marketed to in ways that have nothing to do with reality. In this episode of The L...