The Long Haul

FreightWaves, Adam Wingfield
  • 4.3 (4)
  • Entrepreneurship
  • Updated Weekly

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.

  1. 5d ago

    She Left Interior Design for a Box Truck. Here's What She Learned

    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. Follow the FreightWaves Today Podcast Other FreightWaves Shows

    She Left Interior Design for a Box Truck. Here's What She Learned

  2. Sep 24

    The Fuel Crisis Is Here. Do You Know What It's Actually Costing You?

    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. Just me, the data, and the math that too many carriers are avoiding because they don't want to know what it says.We're going to talk about where diesel is, how we got here, where it might go, and — most importantly — how to calculate what this fuel environment is actually costing you per mile, per load, and per month. Because the difference between a carrier who survives this and one who doesn't isn't which loads they take. It's whether they know their real numbers. Follow The Long Haul Podcast Other FreightWaves Shows

  3. Sep 17

    The Hidden Lane — What Most Truckers Don't Know About Drayage

    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 drayage. And most truckers have never thought about it once.Sergio Manzo has been in it his entire career. Eight years as a driver moving containers through Chicago's rail yards. Now COO of Severo Trucking — the family business his family has been running for over three decades in one of the most demanding intermodal markets in the country. Today we're getting into a part of this industry that the load board crowd has never seen. And I think when you hear what drayage actually involves — the complexity, the discipline, the relationships you have to build — you're going to understand why the carriers who do it well are some of the most insulated operators in the business. Let's get into it. Follow The Long Haul Podcast Other FreightWaves Shows

    The Hidden Lane — What Most Truckers Don't Know About Drayage

  4. Sep 10

    The Detective's Guide to Protecting Your Trucking Company

    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 complicated facts, turn into a verdict big enough to erase a company. And before trucking, he was a law enforcement detective running undercover operations — which is exactly the background you want advising fleets on security in the middle of a cargo theft epidemic. Here's what he'll tell you that most safety conversations won't. The lawsuit doesn't start when the crash happens. It starts years earlier — in the driver file you didn't complete, the camera footage you never reviewed, the coaching conversation you skipped because the truck was making money. When the plaintiff's attorney gets your records, they're not looking for the accident. They're looking for the pattern. And most small carriers are handing them one without knowing it.We get into what actually gets carriers destroyed in litigation, how to use dash cams to coach drivers instead of policing them, the safety management cycle that turns compliance from paperwork into protection, the hours-of-service exceptions most small carriers misuse, what a mock audit catches before the real one does, and — from a former undercover detective — how thieves and fraudsters are actually targeting carriers right now, and what stops them. Good drivers are made great on purpose. This episode is the blueprint. Follow The Long Haul Podcast Other FreightWaves Shows

    The Detective's Guide to Protecting Your Trucking Company

  5. Sep 3

    Cut Out the Middleman — Easy to Say, Now Prove It

    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 father was an owner-operator who lost his business to bad brokers, and Trent built his company to make sure truckers stop getting the bad end of the stick. I respect the wound. Today we test the remedy. Because this show doesn't platform pitches — it pressure-tests them. So Trent came in knowing the format: the claim goes on trial. Is brokering actually the answer for a struggling carrier, or is it a second business bolted onto a first one that isn't working? What does it really take — the bond, the credit, the shippers who don't know your name? And how does "it's not hard" survive a world where the Supreme Court just ruled that anyone selecting carriers can be sued for choosing wrong? He gets every chance to make his case. His numbers, his students, his story. And you get what this show owes you — the pitch, cross-examined, before you pay for it. Somebody's leaving this conversation with a different opinion. Might be him. Might be me. Might be you.

    Cut Out the Middleman — Easy to Say, Now Prove It

  6. Aug 27

    The Deposition — America's Top Trucking Lawyer Takes Me Apart On Air

    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. Mid-episode, we run it live. I play the owner of a nine-truck fleet after a serious crash — a fictional company, built from every real carrier I've ever coached. The 1099 drivers in company trucks. The driver files that got started and never finished. The dash cams nobody watches. The dispatch text that says push through. Greg does what the other side's lawyer would do with all of it, and I sit there and take it, so you can hear exactly what that room sounds like before you're ever in it. Then we break down where I died, what would have saved me, and the truth his four words on our intake form captured better than any regulation ever has — carrier vetting is fluid. The safety bar isn't set by the FMCSA anymore. It's set by juries, after the crash, and most small carriers are being measured against a standard they've never seen. We close with the misclassification time bomb sitting under half the small fleets in this country, and what the biggest carriers in America are doing right now that you can't see from the driver's seat. You've been told your paperwork will be used against you. Today you hear it happen. Follow the Brake Check Podcast Other FreightWaves Shows

    The Deposition — America's Top Trucking Lawyer Takes Me Apart On Air

  7. Aug 20

    Liability Rolls Downhill — Protecting Your Trucking Company After Montgomery v. Caribe

    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 broker problem. Bryan Nelson will tell you the truth — it's about to become your problem. Because when brokers carry that kind of exposure, they don't absorb it. They push it down. Tighter vetting. Deeper background checks on your authority, your scores, your insurance. Rewritten agreements with indemnification language designed to make you hold the bag. Monitoring you've never dealt with before. And carriers with conditional ratings, rough inspection histories, or brand-new authority are about to find doors closing that were open six months ago. Bryan has spent his career on both sides of this table — years as general counsel inside a broker, a motor carrier, and a TMS, and now a partner at a transportation law firm defending trucking companies. He breaks down what the Court actually decided, what brokers are changing right now, the contract language headed for your inbox, and the exact moves that protect your authority, your assets, and your access to freight in the new landscape. Your safety scores just became your sales resume. Your paperwork just became your armor. This episode shows you how to build both. Follow The Long Haul Podcast Other FreightWaves Shows

    Liability Rolls Downhill — Protecting Your Trucking Company After Montgomery v. Caribe

  8. Jul 23

    65 Trucks, One Standard — How to Build an Owner-Operator Fleet That Doesn't Fall Apart

    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. Warehouse operations. Port logistics. Last-mile delivery. Recruiting. Fleet acquisitions. He worked his way through nearly every level of this industry before landing in operations management — which means when he talks about why owner-operators leave, he's not guessing. He's watched it happen from every angle. The trucking industry spends millions trying to find drivers. It spends almost nothing figuring out why they leave. And most small carriers running two, three, five trucks are making the same mistakes the big fleets made twenty years ago — just on a smaller budget with less room to absorb the damage. This episode is about what actually keeps an independent contractor running your freight. Not the sign-on bonus. Not the percentage. The things that determine whether an owner-operator calls you a partner or a problem — and what that decision costs you either way. Follow The Long Haul Podcast Other FreightWaves Shows

    65 Trucks, One Standard — How to Build an Owner-Operator Fleet That Doesn't Fall Apart
See All (80)

Trailer

Ratings & Reviews

4.3
out of 5
4 Ratings

About

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.

Information

  • Creator
    FreightWaves, Adam Wingfield
  • Years Active
    2025 - 2026
  • Episodes
    80

You Might Also Like