Cover image of show The Long Haul

The Long Haul

Podcast by FreightWaves, Adam Wingfield

English

Business

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About The Long Haul

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.

All episodes

66 episodes

episode Freight Doesn’t Kill Most Carriers — Cash Flow Does artwork

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 [https://play.megaphone.fm/mrpthqzxqpywz_euvnb-vg] Other FreightWaves Shows [https://play.megaphone.fm/1ojr5w9ksqa6bo65mx0nig]

21 May 2026 - 31 min
episode The Trucking Industry Didn’t Break Overnight artwork

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 [https://play.megaphone.fm/mrpthqzxqpywz_euvnb-vg] Other FreightWaves Shows [https://play.megaphone.fm/1ojr5w9ksqa6bo65mx0nig]

14 May 2026 - 1 h 5 min
episode Most Small Carriers Sound the Same — And That’s the Problem artwork

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 [https://play.megaphone.fm/mrpthqzxqpywz_euvnb-vg] Other FreightWaves Shows [https://play.megaphone.fm/1ojr5w9ksqa6bo65mx0nig]

7 May 2026 - 38 min
episode Buying the Truck Is the Easy Part — Running the Business Is Where Carriers Fail artwork

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 [https://play.megaphone.fm/mrpthqzxqpywz_euvnb-vg] Other FreightWaves Shows [https://play.megaphone.fm/1ojr5w9ksqa6bo65mx0nig]

30 Apr 2026 - 49 min
episode The Compliance Lie — Why Small Carriers Don’t Take It Seriously Until It’s Too Late artwork

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 [https://play.megaphone.fm/mrpthqzxqpywz_euvnb-vg] Other FreightWaves Shows [https://play.megaphone.fm/1ojr5w9ksqa6bo65mx0nig]

24 Apr 2026 - 55 min
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