have a friend named Marcus.
He grew up in a small town in Tennessee, dropped out of college after one semester, and by the time he was 24, he was behind the wheel of an 18-wheeler hauling freight across state lines. Not because it was his dream exactly, but because it paid well, it gave him freedom, and honestly, Marcus has never been the kind of person who likes sitting still.
I met him years ago when I was passing through Nashville between trips. We stayed in touch the way you do when you’re both the type of people who are always somewhere new. He would text me photos of sunrises over the Rockies or empty highways in West Texas. I would send him photos of street food in Vietnam or temples in Thailand. We understood each other in that way.
But there was always one part of Marcus’s life that stressed him out more than anything else, more than bad weather on mountain passes, more than sleeping in rest stops, more than the long stretches of nothing between cities. That part was insurance.
The Problem Nobody Talks About
When most people think about truck drivers, they picture the open road. The freedom. The big rigs. What they do not picture is the paperwork, the liability, and the very specific financial vulnerability that comes with being an owner operator.
Marcus explained it to me once over the phone while he was parked outside a truck stop in Oklahoma. He owned his own rig. That meant he was not an employee of a company with a fleet and a legal team and an HR department. He was his own business. And that meant every risk, every accident, every unexpected repair, every gap between loads landed entirely on him.
The insurance side of that reality is something most people outside the trucking world never think about. But for owner operators, it is one of the biggest costs and one of the biggest sources of anxiety in the job. Get the wrong coverage and you are exposed. Get overcharged and your margins disappear. Find a provider that does not understand trucking and you end up fighting for every claim.
For years, Marcus was stuck in that cycle. He had policies through providers who treated him like just another number. When he had a minor incident on a job, getting the claim processed felt like a second job on top of his actual job.
How He Found InterSafe, Inc
He told me about InterSafe, Inc during one of our calls last year. Another owner operator he knew on a route through Minnesota had mentioned them. Marcus looked them up, called their number, and said the conversation was different from the start.
InterSafe, Inc was founded in 1992 by former trucking company executives. That detail mattered to Marcus more than almost anything else. These were not people who learned about trucking from a textbook. They came from the industry. They understood the difference between a fleet owner and an independent contractor. They understood bobtail coverage and why it matters. They understood that owner operators do not want to spend forty five minutes on hold explaining what their job actually involves.
The company is based in St. Paul, Minnesota, and they are a coverholder at Lloyd’s, which is one of the most respected names in insurance globally. For Marcus, that meant his coverage was backed by real financial strength, not some small regional provider that might slow-walk a claim when things got difficult.
What the Coverage Actually Looks Like
I am not an insurance expert, and I want to be clear about that. But Marcus walked me through what he actually uses, and it is worth sharing because I think a lot of owner operators do not realize how specific and well-matched InterSafe’s products are to their situation.
The physical damage coverage handles his tractor. If something happens to the truck itself, that is covered. For someone whose entire livelihood depends on that vehicle staying on the road, this is not optional. It is the foundation of everything.
The non-trucking liability coverage, which people in the industry call bobtail coverage, protects him when he is driving his rig but not under dispatch. This is a gap that catches a lot of owner operators off guard. A lot of standard commercial auto policies do not cover this window. InterSafe does.
Then there is occupational accident coverage, which handles injuries on and off the job. Marcus told me about a guy he knew who hurt his back stepping out of his cab in a parking lot. Not a road incident. Not a freight accident. Just a moment of bad luck. That guy was out of work for two months and had nothing covering him. Marcus said that conversation was what pushed him to make sure his own occupational accident coverage was solid.
The Part That Actually Surprised Him
Marcus is not easy to impress. He has been around long enough to be skeptical of anything that sounds too good, and he told me going in that he expected InterSafe to be fine but not remarkable.
What caught him off guard was the service.
He got a quote fast. The underwriting process was straightforward. When he had a question about his policy a few months in, he called during business hours and got an actual person who knew what he was talking about. He said it felt less like dealing with an insurance company and more like dealing with someone who actually cared whether his business survived.
That sounds simple. But when you have spent years dealing with providers who make you feel like an inconvenience, simple starts to feel like a lot.
Why I Am Writing About This
I write about travel, about life abroad, about what it looks like to build a life outside the expected path. Marcus is someone who has done that too, just on American highways instead of overseas.
He is not a dramatic person. He does not exaggerate. So when he told me that switching to InterSafe, Inc was one of the better business decisions he made in the last few years, I paid attention.
If you are an owner operator, an independent contractor in trucking, or a fleet owner trying to sort out coverage that actually fits how you work, InterSafe, Inc is worth a conversation. You can reach them at intersafeinc.com or call 800-896-9688 during business hours.
Marcus is back out on the road somewhere right now. Probably somewhere with a good sunrise and a bad cup of coffee. But at least he is not losing sleep over his insurance anymore.