FreightWaves, Adam Wingfield

The Long Haul

Business EN ↓ 71 episodes

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.

Author

FreightWaves, Adam Wingfield

Category

Business

Latest episode

Jul 9, 2026

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Episodes

Smarter Loads, Stronger Margins – Carlos Otero on Fixing the Routing Problem in Trucking 26.06.2025

This week on The Long Haul, Adam sits down with Carlos Otero, CEO of efRouting—a platform using real data to help small carriers stop bleeding money on poor load choices. Carlos blends academic freight research with family trucking roots to explain why chasing high-rate loads isn’t always profitable, how routing is costing carriers more than they think, and what a smarter, multi-day planning strat...

Behind the Broker Curtain – What Carriers Don’t Know About Being Behind The Broker’s Desk 19.06.2025

In this episode of The Long Haul, Adam sits down with Coleman Ruffin—industry vet, team builder, and former CH Robinson broker—to expose what small carriers need to know about how freight really gets moved. Coleman shares the truth about rate negotiations, how brokers decide who gets the good freight, and the quiet reasons carriers get skipped over. This is a raw look inside the brokerage world th...

Why Most Small Carriers Fail at Marketing – And What Kara Brown Says to Do Instead 12.06.2025

This week on The Long Haul, Adam sits down with Kara Brown—supply chain marketing powerhouse, author of The Revenue Engine, and CEO of LeadCoverage—to expose why most small carriers are wasting time and money trying to get noticed. Kara breaks down the exact mistakes holding carriers back, the marketing myths that need to die, and the three-step framework she’s used to help logistics companies sca...

Building More Than a Brand – Rahmel Wattley on Truck N’ Hustle and Industry Impact 05.06.2025

This week on The Long Haul, Adam sits down with Rahmel Wattley—founder of Truck N’ Hustle, creator of FreightFest, and one of the most influential voices in trucking media. Rahmel shares how he went from driver recruiting to building a movement, what he’s learned from interviewing hundreds of industry leaders, and how small carriers can tap into the power of storytelling, strategy, and community t...

Fixing CDL Training from the Inside – A Conversation with CDL Shorty 29.05.2025

This week on The Long Haul, Adam sits down with Avante Jackson—better known as CDL Shorty on YouTube—to talk about what’s broken in CDL training and what needs to change. As a CDL instructor and content creator, Shorty gives a raw, behind-the-scenes look at how new drivers are being rushed through the system, the lack of real-world prep, and how better training could improve safety, retention, and...

The Fight Against Load Board Fraud – A Candid Talk with Brian Woodring 22.05.2025

This week on The Long Haul, Adam sits down with Brian Woodring, owner-operator and outspoken advocate for protecting drivers from load board fraud. Brian shares what fraud really looks like behind the scenes, how to spot the warning signs before you get burned, and why carriers need to be more cautious than ever when booking freight. They dive deep into the good, the bad, and the ugly across diffe...

Tariffs, Drayage, and the Real Story on the Ground – A Conversation with Corisa Carter 15.05.2025

This week on The Long Haul, Adam sits down with Corisa Carter—co-founder of the Charleston Truck Expo and a true boots-on-the-ground expert in drayage and port operations. Corisa brings real-world insights on how new tariffs are already impacting freight at the ports, what small carriers need to watch out for, and how the drayage world is shifting right now. They dive deep into what’s happening be...

From Box Trucks to Full Truckload – How Elizabeth Moscoso is Building Moscoso Express 08.05.2025

This week on The Long Haul, Adam sits down with Elizabeth Moscoso, founder of Moscoso Express, a growing box truck and full truckload carrier based out of Elk Grove Village, Illinois. Elizabeth shares her journey from starting small with box trucks to scaling into the full truckload market, and the lessons she’s learned about surviving and thriving as a small carrier. They talk about the realities...

No Gym, No Problem: How Garrett Steenblik is Helping Truckers Take Their Health Back 01.05.2025

In this episode of The Long Haul, I’m joined by Garrett Steenblik—founder of Trucker Body Shop and a former driver who turned his own health journey into a full-blown movement. Garrett breaks down how drivers can take control of their health right from the cab of their truck—no gym, no gimmicks. We talk about the realities of being on the road, how to build habits that stick, and practical exercis...

The Insurance Game: What Every Small Carrier Needs to Know 24.04.2025

In this episode of The Long Haul, I sit down with Jessica Howington from United Commercial Insurance to break down the truth about trucking insurance—no fluff, just facts. We talk about what small carriers need to understand before signing their next policy, how to keep premiums down at renewal time, and what underwriters are really looking for. Jessica brings years of frontline experience, and th...

Rolling Up Your Sleeves: How Small Carriers Can Land Direct Shippers with Justin Lu 17.04.2025

In this episode of The Long Haul, Adam Wingfield sits down with Justin Lu, CEO of Truckpedia, to break down one of the most critical moves for small carriers—getting out of the broker dependency cycle and going directly to shippers for freight. Justin knows this game firsthand. He took his family’s 3-truck operation and scaled it to 50 trucks by putting in the work, cold calling shippers, and secu...

Lease On or Stay Independent? Hard Truths for Owner-Operators with Tobenna Arodiogbu 10.04.2025

In this episode of The Long Haul, Adam Wingfield sits down with Tobenna Arodiogbu, CEO and co-founder of CloudTrucks, to break down one of the biggest decisions every owner-operator faces: Should you lease on or stay independent? With years of experience building technology to empower trucking entrepreneurs, Tobenna shares hard-hitting insights into why some owner-operators succeed while others fa...

Cracking the Code: Building Strong Broker Relationships for Better Freight with Dan Lindsey” 03.04.2025

In this episode of The Long Haul, Adam Wingfield sits down with Dan Lindsey, Founder of Broker Carrier Summit, to uncover the secrets to building better broker relationships—and why it’s the key to securing consistent, profitable freight for your trucking business. For many carriers, brokers feel like a necessary evil. But the truth is, strong broker relationships can make or break your success. D...

Fleet Maintenance, DPF Nightmares & Towing Scams: What Every Small Carrier Needs to Know with Tyler Harden 27.03.2025

In this episode of The Long Haul, Adam Wingfield sits down with Tyler Harden, Chief Product Officer at TTN Fleet Solutions, to tackle some of the biggest fleet maintenance headaches facing owner-operators and small carriers. From DPF system failures that can take trucks off the road to towing scams that drain bank accounts overnight, Tyler shares insider knowledge on how to protect your business f...

From the NFL to Trucking: Mike Tolbert on Scaling, Pivoting, and Fixing the Parking Crisis 20.03.2025

From NFL Pro Bowler to trucking entrepreneur, Mike Tolbert knows what it means to take on challenges—both on the field and in business. After a nine-year NFL career with the Chargers, Panthers, and Bills—where he earned three Pro Bowl selections, two All-Pro honors, and helped lead Carolina to a Super Bowl run—Mike tackled a new industry: trucking. During the pandemic, he launched his own trucking...

Money Moves: Financial Strategies for Owner-Operators with Vanessa Gant 13.03.2025

In this episode of The Long Haul, Adam Wingfield sits down with Vanessa Gant, the Founder and CEO of Provision Accounting Solutions, to break down the financial strategies that every owner-operator and small carrier needs to know. Vanessa, known as “The Money Architect,” has spent over 15 years helping trucking businesses increase profitability, reduce tax liabilities, and stay compliant. From avo...

Special Edition: CVSA’s 2025 Out-of-Service Updates – What Truckers Need to Know Before April 1 06.03.2025

CVSA’s New 2025 Out-of-Service Rules Go Into Effect April 1—Are You Ready? If you’re an owner-operator or run a small fleet, these new CVSA regulations could sideline your truck and cost you thousands in downtime. The Commercial Vehicle Safety Alliance (CVSA) has made major changes to out-of-service violations for drivers, brakes, tires, and suspensions. If you’re not prepared, your next DOT inspe...

Hellbent on Efficiency: Scaling from 1 to 10+ Trucks with Jamie Hagen of Hellbent Express 27.02.2025

Growing a trucking business from a single truck to a thriving fleet requires more than just hard work—it demands relentless efficiency. In this episode of The Long Haul, I sit down with Jamie Hagen, the owner of Hellbent Express, to break down the mindset and strategies that fueled his rapid growth. Jamie shares how his unwavering commitment to efficiency—whether in fuel management, operations, o...

From 180+ Trucks to Higher Profits: The Smart Pivot of Marcus Jones w/ 314 Logistics 19.02.2025

In this episode of The Long Haul, I sit down with Marcus Jones, the owner of 314 Logistics, to unpack the highs and lows of running a high-volume trucking operation. At his peak, Marcus had 180+ trucks running frac sand, generating over $18 million in annual revenue. But as the market shifted, he had to make a tough decision—pivot or perish. Marcus shares how he redefined success by focusing on ef...

Legacy, Lessons, and the Playbook: A Conversation with Craig Fuller 12.02.2025

In this episode of The Long Haul, I sit down with Craig Fuller, a name synonymous with innovation in the trucking and freight industry. We dive into his deep-rooted family history in trucking, the hard lessons he’s learned from entrepreneurial failures, and how those setbacks ultimately shaped his success. Craig opens up about finding his niche, what it took to carve out his own lane, and the insp...

The Long Haul Trailer 12.02.2025

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