The Long Haul

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 this conversation is a must-listen if you’re trying to stay insured without breaking the bank. Whether you’re a new authority or a seasoned owner-operator, there’s something in this episode that’ll save you money—and maybe your business.

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 securing direct freight contracts. Now, through Truckpedia, he’s helping other small carriers do the same—showing them how to stand out, build credibility, and win direct freight opportunities.

We go deep into why small carriers need to stop waiting for freight to come to them, the common mistakes they make when approaching shippers, and how to confidently pitch their services to land steady, high-paying freight.

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 fail. From the hidden pitfalls of leasing on to the financial traps that put drivers out of business, we go deep into the realities that many don’t talk about.

We also cover the future of trucking—how technology is changing the way owner-operators do business, how CloudTrucks is providing more flexible options, and whether traditional lease-on models will even exist in five years. If you’re an independent trucker or thinking about becoming one, this episode is a must-listen.

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. Dan breaks down the biggest mistakes carriers make, how to position yourself as a broker’s go-to carrier, and why communication and reliability are non-negotiables in this industry.

We also tackle the red flags brokers look for, how to negotiate better rates, and ways to protect yourself from bad broker deals. Whether you’re an owner-operator looking to break free from load board dependency or a small fleet trying to establish direct broker relationships, this episode is packed with insider strategies to help you level up your business.

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 from costly mistakes. We also dive into the hidden dangers of roadside breakdowns, predatory towing practices, and why small fleets need a proactive maintenance strategy to stay profitable.

With his background in fleet maintenance, towing, and emergency roadside assistance, Tyler doesn’t hold back on real-world stories of disaster—and more importantly, how to avoid them. If you run a truck or a small fleet, this is an episode you can’t afford to miss.

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 company and quickly scaled operations. But as costs soared and the freight market shifted, he faced the brutal realities of running a fleet. In this episode, Mike opens up about what went right, what went wrong, and what he’d do differently if he had to start over.

Now, he’s on a new mission—solving the truck parking crisis. With limited options in major metro areas, restrictive zoning laws, and growing demand, he’s running into roadblocks that could impact the entire industry.

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 avoiding financial pitfalls to maximizing cash flow, she shares no-nonsense advice on how to build a profitable and sustainable trucking business. We get into tough topics like why so many carriers run loads under their breakeven point, the real impact of factoring, and why ignoring your books can put you out of business faster than a bad freight market.

If you’re an owner-operator or small fleet looking to take control of your finances and secure your future, this episode is a must-listen.

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 inspection could shut you down.

In this special edition episode, I break down:

• New driver rules (CLP trainers & medical cards)

• Brake system violations that now shut down your truck instantly

• Tire rule updates (leaks & automatic out-of-service violations)

• Suspension crackdowns that could cost you big

• How to stay compliant and avoid unnecessary downtime

Don’t risk getting parked. Watch now and get ahead of these changes before April 1.

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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, or driver productivity—helped him scale from one truck to over ten. We dive into the power of data-driven decision-making, technology adoption, and how small carriers can maximize profitability without sacrificing service. If you’re serious about running a lean, profitable trucking operation, this is one conversation you don’t want to miss.

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 efficiency over fleet size, proving that you don’t need a massive number of trucks to be highly profitable. He breaks down the strategies he used to streamline operations, increase profitability, and create a sustainable business model in an industry that often prioritizes growth over efficiency.

If you’ve ever wondered whether bigger really means better, or if there’s a smarter way to scale in trucking, this episode is for you. Tune in for real insights, lessons learned, and a blueprint for making more with less in the logistics game.