How do you find companies that hire owner operators with trucks older than 2000?

Some don't / won't say; usually a case'by'case basis. Find the ones you are interested in, or that are interested in him, and start calling like now (okay well in the daylight hours; I'm a night driver...) and you'll probably be surprised at how many nibbles you get.

@Chinatown ??

What does he haul, or prefer to?!? Vans, reefs, open decks, tanks, H/H, et al?

Off to work; wish you both the best. All isn't lost, for sure. (For instance, QC employs one of my pals, with a '98 Petercar hood. Tanker operation; Quality Carriers!)

 

Bennett Motor Express advertises "no age limit" trucks.
Bennett Motor Express | Flatbed, Heavy Haul & Dry Van Trucking
https://www.bennettig.com/bennett-motor-express
From the website - "No age restrictions on tractors"
Affiliated Companies

• Bennett Motor Express, LLC
• Ace Doran Hauling & Rigging Co., LLC
• Bennett Heavy & Specialized, LLC
• Bennett International Logistics, LLC
• Bennett International Transport, LLC
• Bennett Truck Transport, LLC
• Bennett DriveAway
• Bennett Distribution Services, LLC
• Bennett On-Site Services, LLC (BOSS)
• RoadMasters div. of Bennett Truck Transport

 

This division requires a 1 ton pickup truck and hauls travel trailers. Might have to pull 2 or 3 travel trailers at one time.
Pickup truck no older than year 2000.
Bennett Motor Express
https://bennettdrivers.com/driveaway-pickup
Earn big without the rig with high-paying truck driving opportunities in Bennett’s DriveAway Pickup division! If you have a pickup truck that’s one ton or greater that can handle one unit at a time OR up to three-unit combinations with our haul-and-tow vehicles, you can be your own boss while getting paid to see this great country.

 

These websites are for heavy duty pickup trucks after market sleeper berth kits.
Sleeper Berth - Woodhouse
https://www.woodhouse.com/sleeper_berth
Woodhouse Sleeper Berth is part of the Woodhouse Auto Family, a family of dealerships located in the Omaha, Nebraska metro area which includes 16 franchise locations that sell over 25,000 vehicles a year across the United States. Woodhouse is known as a “truck” store and has been a leader in heavy duty truck sales in all of the domestic brands.
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Cowtown Sleepers
https://www.cowtownsleepers.com
Added Pickup truck Seating for your children and pets, truck Storage, and Pickup truck Camping inside the safety of your truck and Sleeper Berth that bolts to your truck for Hotshot Truck Drivers. Get your BEST night's sleep in your pickup truck with our Cowtown Sleepers.

 

It will probably take a little extra work to find one. Because the trucking company is on the hook if anything like an accident happens. Probably the first thing they will want to check is paper log books. They know why some people enjoy running paper vs ELD

 

I don’t think Landstar cares how old it is, but have to run eld...no paper logs.

 

What state do you live in?

 

Yea what state. In NE PA or upstate NY I can give you a lead