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. Factoring, Lifeline Or Trap?

    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

    54 min
  2. Success Starts With Better Decisions

    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

    1 hr
  3. Why Most Small Carriers Never Touch Military Freight

    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

    51 min
  4. Freight Doesn’t Kill Most Carriers — Cash Flow Does

    May 21

    Freight Doesn’t Kill Most Carriers — Cash Flow Does

    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 entering transportation finance and working directly with small carriers across the Southeast. This conversation breaks down: Why profitable carriers still go out of business The dangerous cash flow cycle many small fleets ignore Why emotional decision-making destroys margins The hidden operational costs small carriers overlook What owner-operators misunderstand about factoring And why discipline matters more than revenue This episode is not about promoting factoring. It’s about understanding how trucking businesses survive. Follow The Long Haul Podcast Other FreightWaves Shows

    31 min
  5. The Trucking Industry Didn’t Break Overnight

    May 14

    The Trucking Industry Didn’t Break Overnight

    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 how outdated regulations, industry evolution, and a lack of accountability continue shaping modern trucking today. This conversation dives into: Why modern trucking problems didn’t start in 1980 How old regulations still impact carriers today Why social media oversimplifies complex industry issues The relationship between brokers and carriers Why relationships still matter more than technology And why small carriers fail when they spend more time blaming than adapting This episode isn’t about nostalgia. It’s about understanding how we got here. Follow The Long Haul Podcast Other FreightWaves Shows

    1h 5m
  6. Most Small Carriers Sound the Same — And That’s the Problem

    May 7

    Most Small Carriers Sound the Same — And That’s the Problem

    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 recruiting is still broken for small fleets What drivers actually care about vs what carriers think they care about Why “we treat drivers like family” isn’t working anymore How small fleets can compete without big budgets And how to fix your hiring problem without wasting money If you’re struggling to hire or keep drivers… this one is going to challenge how you think. Follow The Long Haul Podcast Other FreightWaves Shows

    39 min
  7. Buying the Truck Is the Easy Part — Running the Business Is Where Carriers Fail

    Apr 30

    Buying the Truck Is the Easy Part — Running the Business Is Where Carriers Fail

    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 are unprepared for what ownership actually requires The massive gap in back-office knowledge The compliance mistakes that quietly shut carriers down The difference between driving a truck and running a company And what it really takes to build something that lasts If you think owning a truck means you’re running a business… this episode will challenge that. Follow The Long Haul Podcast Other FreightWaves Shows

    50 min
  8. The Compliance Lie — Why Small Carriers Don’t Take It Seriously Until It’s Too Late

    Apr 24

    The Compliance Lie — Why Small Carriers Don’t Take It Seriously Until It’s Too Late

    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 actually happens when things go wrong.We break down: The biggest compliance mistakes small carriers make Why many fleets think violations don’t matter The real consequences of non-compliance during an accident How enforcement is changing across the industry And the hard truth about what DOT compliance really means If you’re running trucks and treating compliance like a checklist, this episode may change how you look at your entire operation. Follow The Long Haul Podcast Other FreightWaves Shows

    56 min
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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
    70

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