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. 3d ago

    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

  2. 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

  3. 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

  4. Jul 16

    Rock Bottom to Rockstar — The Jerry Murphy Story

    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 his drivers call home. And this past June, he closed on something most small carriers only talk about — he bought a trucking company that's been running for 40 years, from an owner who chose Jerry over every bigger check he could've taken, because he trusted Jerry to take care of his people. But here's what nobody watching from the outside knew. While that deal was sitting in limbo, Jerry lost his brother. And the man who had rebuilt his whole life found himself in the darkest place he'd been since he put the bottle down. Sleeping past his alarm for the first time in years. Walking away from the jiu-jitsu classes he loved to teach. Carrying something he couldn't name. He didn't drink. Not once. He didn't even think about it. Months later, he signed the papers on the biggest move of his life.This is a conversation about what rock bottom actually looks like, what it takes to climb out more than once, and why the hardest fight isn't building the business — it's believing you deserve what you built. If you're carrying something right now and telling everybody you're fine, this episode is for you. Follow The Long Haul Podcast Other FreightWaves Shows

    Rock Bottom to Rockstar — The Jerry Murphy Story

  5. Jul 9

    From the Inside Out — How Trucking Became the Way Back

    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 years grinding load boards and chasing freight that barely covered his costs. And then three years ago he did something most carriers only talk about — he walked away from broker dependency and secured a direct waste-hauling contract that changed not just his revenue, but how he sees the entire business. This is a conversation about what it actually takes to build something when the world has already decided what you are. About treating trucking like a business when everybody around you is treating it like a job. About finding consistent freight in an industry that makes you earn every relationship you get. If you've ever been told you were done — by a system, by a market, by a bad decision — this episode is for you. Follow The Long Haul Podcast Other FreightWaves Shows

    From the Inside Out — How Trucking Became the Way Back

  6. Jun 18

    Factoring, Lifeline Or Trap?

    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 that doesn't get talked about honestly — a lot of carriers who hate factoring don't hate factoring. They hate the decision they made around it. The company they chose. The contract they signed without understanding. The moment they confused having cash in their account with actually being ahead. Ivan Martinez and George McWilliams have spent years on the other side of that conversation. Between them they've worked with owner-operators and small fleets across every kind of market condition — the freight boom, the recession, the recovery happening right now. George grew up around trucking. This industry isn't abstract to him. Ivan has watched carriers use factoring to grow and watched others use it as a band-aid over a cash flow problem that was bigger than any factoring arrangement could fix. Today we're not here to sell anything. We're here to have the conversation most people avoid — what factoring actually is, where the industry went wrong, what the legitimate criticisms are, and what every small carrier needs to understand before they sign anything. Follow The Long Haul Podcast Other FreightWaves Shows

    Factoring, Lifeline Or Trap?

  7. Jun 11

    Success Starts With Better Decisions

    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 entrepreneurship. Before trucking, Vic spent 28 years as a barber, building relationships, serving customers and mastering a trade. Then he made a decision many people only talk about — he bet on himself and started over. Nearly six years later, he has experienced the highs of great-paying freight, the lows of expensive repairs, the challenges of building a small fleet and the reality of operating in one of the toughest industries in America. But this conversation is not really about trucks. It is about ownership. It is about accountability. It is about the decisions that separate the people who survive from the people who quit. Over the years, Vic has built an audience of more than 100,000 subscribers by challenging some of the most common beliefs in trucking. From chasing load boards and buying trucks too early to blaming brokers, rates and market conditions, he argues that many of the problems carriers face start long before they ever book a load. This is not the social media version of trucking. This is the real version. The version where cash flow matters, mistakes are expensive, discipline beats motivation and success often comes down to how you think when things are not going your way. If you are an owner-operator, small fleet owner or entrepreneur trying to build something that lasts, this conversation will challenge the way you think about trucking, business and yourself.  Follow The Long Haul Podcast Other FreightWaves Shows

    Success Starts With Better Decisions

  8. May 28

    Why Most Small Carriers Never Touch Military Freight

    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 Consultants, to break down how military freight actually works, why the system operates under a completely different standard, and what small carriers misunderstand most about getting involved. This conversation digs into: Why military freight demands tighter compliance Why most carriers struggle to qualify The difference between transactional freight and trusted freight How the DoD views risk and carrier accountability Why discipline matters more than truck count And what the broader trucking industry can learn from military logistics This is not a sales episode. It’s a real discussion about standards, structure, and what separates professional carriers from everyone else. Follow The Long Haul Podcast Other FreightWaves Shows

    Why Most Small Carriers Never Touch Military Freight
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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
    75

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