Podcast
The Long Haul
Hosted by FreightWaves, Adam Wingfield · EN
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.
13episodes
Episodes
Newest firstAll episodes
Freight Doesn’t Kill Most Carriers — Cash Flow Does
2w ago00:31:00Tap to summarizeMost 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
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The Trucking Industry Didn’t Break Overnight
3w ago01:05:25Tap to summarizeEverybody 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third-generation trucking operator, Navy veteran, brokerage leader, and trucking history enthusiast — to break down how outdated regulations, industry evolution, and a lack of accountability continue shaping modern trucking today.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
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Most Small Carriers Sound the Same — And That’s the Problem
4w ago00:38:55Tap to summarizeMany 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
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Buying the Truck Is the Easy Part — Running the Business Is Where Carriers Fail
Apr 3000:49:40Tap to summarizeEveryone 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
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The Compliance Lie — Why Small Carriers Don’t Take It Seriously Until It’s Too Late
Apr 2400:55:51Tap to summarizeMost 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
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Voices from the Floor at MATS 2026
Apr 1600:39:06Tap to summarizeIn 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 Other FreightWaves Shows
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Falling Through the Cracks: DACA Drivers vs New CDL Rules
Apr 900:29:12Tap to summarizeIn 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 real-world encounters to ongoing legal challenges, this conversation dives into the gap between policy and reality—and the human cost of being overlooked. Whether you’re a driver, carrier, or policymaker, this is a perspective you’re not hearing in the headlines. Follow The Long Haul Podcast Other FreightWaves Shows
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From Kitchen to Cab: Mastering Trucking Margins
Apr 200:35:15Tap to summarizeIn 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 in Manhattan—to becoming a successful owner-operator. He reveals how the razor-thin margins of the culinary world taught him to "squeeze" every bit of profit out of his trucking operation, from meticulous oil sampling to understanding his truck's specific torque curve. Follow The Long Haul Podcast Other FreightWaves Shows
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How Small Carriers Can Get Real Value From the MATS Truck Show
Mar 2600:41:49Tap to summarizeEvery 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 entire year — if you approach it the right way.In this solo episode of The Long Haul Podcast, Adam breaks down how to actually use the show to grow your trucking business.We’ll cover:• How to prepare before you arrive• The vendors you should actually talk to• How to use the education sessions to your advantage• The networking opportunities most people miss• And the biggest mistakes owner-operators make at truck showsBecause if you’re going to spend the time and money to attend MATS, you should leave with more than pictures of shiny trucks.You should leave with knowledge, connections, and opportunities that help your business grow. Follow The Long Haul Podcast Other FreightWaves Shows
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The New Cargo Theft – Fake Drivers, Real Freight
Mar 1900:38:15Tap to summarizeCargo 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 the tools or knowledge to detect them.We talk about:• How fake driver identities are being used to steal freight• Why even legitimate drivers can get caught in the middle• The growing financial risk to small fleets• And the uncomfortable truth about how vulnerable the industry really isThis episode isn’t about technology.It’s about understanding the threat before it costs you a load, a customer, or your business. Follow The Long Haul Podcast Other FreightWaves Shows
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