The Long Haul

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 behind the scenes that isn’t making the headlines, plus Corisa shares hard-earned advice for small fleet owners looking to survive and thrive in today’s market. SiriusXM keeps truck drivers informed and entertained with coast-to-coast coverage across the US and Canada. Listen to what you love from anywhere on the road with 24/7 ad-free music, plus sports, news, talk, and comedy. Hear your favorites on every haul for just $6.06/month. Sign up at siriusxmfleet.com.

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 of building a trucking business today, the mindset it takes to push through the tough times, and the strategies Elizabeth uses to stay competitive. SiriusXM keeps truck drivers informed and entertained with coast-to-coast coverage across the US and Canada. Listen to what you love from anywhere on the road with 24/7 ad-free music, plus sports, news, talk, and comedy. Hear your favorites on every haul for just $6.06/month. Sign up at siriusxmfleet.com.

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 exercises that work in tight spaces with tight schedules. If you’ve been putting your health on the back burner, this conversation will hit home. SiriusXM keeps truck drivers informed and entertained with coast-to-coast coverage across the US and Canada. Listen to what you love from anywhere on the road with 24/7 ad-free music, plus sports, news, talk, and comedy. Hear your favorites on every haul for just $6.06/month. Sign up at siriusxmfleet.com.

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.