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The Detective's Guide to Protecting Your Trucking Company | The Long Haul artwork

The Detective's Guide to Protecting Your Trucking Company | The Long Haul

FreightCasts

September 10, 2026

Josh Lovan has seen how trucking companies die. Not slowly, from rates. Fast, from one crash.

Speakers Adam Wingfield, Josh Lovan

TopicsBusiness NewsNewsDaily News

Adam Wingfield (0:00)

Fast-paid matters, protection matters too. Sumar Financial helps owner operators and small carriers get paid the same day with non-recourse factoring and protection beyond the typical 90-day period. Plus, flexible plans with no long-term commitment and support from a team that understand trucking. Visit sumar.com to learn more. Here's how a trucking company actually dies. It's not necessarily a freight market, it's not when fuel prices spike, it's a Tuesday, a crash, and a phone call.

Today's guest was the man who took that call. Director of Safety and Security for a Major Carrier, from accident scenes to OSHA investigations, to deposition rooms, he's watched one wreck with messy facts and shared fault turn into a verdict with enough zeros to erase everything a single owner built. And here's the part that should keep you up.

In almost every one of those cases, the company lost the lawsuit years before the crash.

In the files, in the footage nobody reviewed, in the coaching that never happened. And oh, and before trucking, he was also an undercover detective.

So we're also going to talk about the people actively trying to steal your freight and your identity right now from a man who used to hunt for people just like that for a living. This one's the field manual, so let's get to work. If you run your business on guest work, you're putting yourself in a bad position before the wheels even turn. And right now, more than ever, who you align your business with matters. One thing I've always been a big fan of is transparency, whether it's knowing your numbers, knowing your lanes, and knowing exactly what you're getting into before you even book a load. And that's why Amazon Relay stands out. Up front rates, unlimited mileage, accurate mileage, and real appointment times, these are the things you can actually make a decision based on facts and not just assumptions. Whether you have box trucks, drive vans, it doesn't matter. What matters is you're operating with clarity and consistency. So if you're serious about building something sustainable and not just chasing whatever pops up, make sure you go to relay.amazon.com and check it out.

Welcome to The Long Haul, the podcast dedicated to empowering small carriers and owner-operators to drive their business forward. I'm your host, Adam Wingfield, bringing you insights from industry leaders, real-world success stories, and strategies to help you navigate the road to profitability. Whether you just getting started or looking to take your fleet to the next level, this is the show where trucking meets opportunity. So buckle up, it's time to go to distance.

Welcome back to The Long Haul. A few episodes back, we broke down how the Supreme Court changed the liability game for everybody who touches freight. Today is the other half of that conversation because knowing the law changes one thing, building an operation that survives it is another. Josh Lovan spent 15 years in this industry, including running safety and security for a major carrier, through accidents, hazmat, OSHA, trial prep alongside the legal department. Today, he's an industry business advisor at J.

Josh Lovan (3:03)

J.

Adam Wingfield (3:03)

Keller, where he works with fleets from one truck to 10,000 on hours of service, injury prevention, and safety management.

Before any of that, he carried a badge. He was a detective working undercover operations. So he got safety director, courtroom veteran, former cop, one chair, let's use him. Josh, welcome to The Long Haul today.

Josh Lovan (3:23)

Man, happy to be here. What a great setup. I'm excited.

Adam Wingfield (3:27)

Man, I'm excited as you are, man. We both got to experience a wonderful city around the same time, man. That was pretty cool.

Josh Lovan (3:33)

That was, yeah. Speaking of cool, no pun intended, right? But yeah, I was in the low 70s there. It was wonderful.

Adam Wingfield (3:39)

Seattle's is a nice city. Shout out to Seattle. So let me dig right on into it, man. You've had three careers that most people would consider a full life in each of them, from a cop, safety director, and advisor. Walk me through how a detective ends up running safety for a trucking company.

Josh Lovan (3:54)

Yeah, it's pretty interesting. I got a call from my captain at the time. I was in an undercover capacity. I drove a Ford Mustang, was investigating all kinds of crimes, including narcotics and a major trucking company domiciled in the same jurisdiction I worked in.

They were always a good sponsor for the Fraternal Order of Police and stuff like that. So my captain assigned me to it and just knew it would be thoroughly done. To make a long story real short, in the four weeks that followed, we did about a half a dozen search warrants, kicked in doors, recovered a bunch of stolen property, and they offered me a job about six weeks later. So I was actively testing for federal law enforcement, was going to go into the US Marshals Department, but this allowed me to stay local. And it's kind of weird, the older you get, your dreams sometimes are displaced by your family's dreams, your children's dreams. This allowed me to stay local and raise a family, and it was great experience. And that's kind of what led me from law enforcement into the motor carrier world. And I went in just solely as the security guy for a company that had 245 locations in all 50 states. And so primarily my focus was all about security for the first four or five years before I kind of got into the safety thing and ultimately became the director of safety and security for the entire company.

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