2yr experience dilemma… need advice

Discussion in 'Trucking Schools and CDL Training Forum' started by Kwkid133, Feb 23, 2026.

  1. Kwkid133

    Kwkid133 Bobtail Member

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    I’m vice president of my family’s six truck fleet. Our best paying and most consistent contract is team freight only. The last few years have been tough, and drivers are hard to come by, especially for coast to coast team runs at the money I offer (admittedly terrible). This is 40 years of hard work and sacrifice by my parents that I’m trying to carry forward, and this business has been everything to me since I could walk and talk. My wife has recently agreed to get her cdl and come team with me to help better the financial position of the company overall so that we can offer competitive pay to good, experienced drivers. However, we have been met with a very firm and decisive “no” from our insurance company. They say unless she drives for a mega fleet 2 years first, they aren’t touching her no way, no how, even if she’s only driving team with me. (I have almost 20 years safe no tickets, no accidents, as do all 10 of the drivers I have) Obviously this isn’t going to work. Has any other small fleet owners/owner ops encountered something similar? Did you find a work around to get your spouse covered without having to shutter your business and drive for a mega fleet? Any help or advice appreciated.
     
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  3. North Pole Nightmare

    North Pole Nightmare Road Train Member

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    I drove for Lynden a few years,many of the drivers wives got their cdl so they could team up,no problem.

    I would check with different insurance companies.
     
  4. TurkeyCreekJackJohnson

    TurkeyCreekJackJohnson Medium Load Member

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    If it ain't the lawyer, it's the accountant, if it ain't the accountant, it's the insurance brokers. Everyone wants their piece of your pie. I hope you can overcome this and keep the dream alive.
     
  5. ducnut

    ducnut Road Train Member

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    Educate me. You and your wife want to team, in order to better your parents’ company financials enough to increase the pay of 10 company drivers? That math ain’t mathing, especially in today’s market.

    You and your wife would be better off to hire on with Dot Foods, send her through one of their schools, then, team with them. You’d make $100K-$120K, each; be home every 5 days-ish, unless you don’t want to be; have a full benefit package, including free healthcare at their facilities; and whole bunch of other perks.

    Riding a sinking ship to the bottom of the ocean, because of sentimental reasons, makes no sense to me, when that decision may drown you and her with it. You two have your own lives and long-term, financial wellbeing you need to be looking out for.
     
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  6. Kwkid133

    Kwkid133 Bobtail Member

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    Economies of scale vs overhead. I’ve cut overhead as much as I’m willing to. One more truck will generate enough additional revenue to cover its costs with no increase in overhead as well as a small increase in wages (which might be enough to attract an additional team for my empty truck) My rates are good, but not good enough at the current volume of loads. I either need more money per mile (not gonna happen in the current market, already tried) or more trucks running. I have 3 teams full time running right now, and 1 solo regional route that two part time drivers cover alternately. Two of the teams are owner operators, one is one of my fleet trucks. The company team I’ve already upped their wages, though I’d like to up them more. I have 1 truck empty that’s paid for, and another that I have been driving solo off the dat board that I’d like to move to my team contract due to better rates and consistency, plus more growth potential. My long term goals are growth, not merely above survival which is where I am now. The easiest solution is to run full time with my wife and reinvest earnings in the business as a temporary solution (maybe year or 2) to see what gives in our favor. If I made it sound like it was a sinking ship, I apologize. It’s been difficult, but we’re keeping above water. I should note that the ten drivers also includes mom and dad, who are both battling cancer and unable to drive, but still maintain their CDL’s and are listed as drivers on insurance. My sister and I are to inherit ownership. My sister and her husband have also discussed going team at some point, but neither have their cdl. No doubt there’s more money for myself elsewhere, if that mattered I’d’ve done it years ago. Something to be said for my last name being on the door.
    As for the benefits and perks, I already have those and I provide them to my company drivers as well (after two years I pay health insurance in full). Hard to beat taking time off on my terms. Is it truly off? No, as I usually have a phone stuck up my ##* sideways. As long as the loads are covered and bills are paid then I don’t have to be on the road, it just helps a lot when I am. That’s also allowed me to help take care of Mom and Dad, which is hard to put a price on.
    It’s on the precipice of being able to do really well and provide a comfortable living for everyone, including myself and my wife. It just needs a nudge in the right direction.

    Thank you for challenging my understanding of my own situation. It helps.
     
    Last edited: Feb 24, 2026
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  7. Kwkid133

    Kwkid133 Bobtail Member

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    I guess more specifically, I’m asking if anyone has experience with underwriters who will take a driver with less than two years experience and not charge a fortune for doing so? What insurance company? Or has anyone heard of supplemental policies that will pick up additional liability on specific drivers, rather than requiring an increase in liability premiums on each piece of equipment across the board over one inexperienced driver. I could probably throw money at this and solve the problem, but it would double my liability premium, which would negate the whole point of putting my wife in the truck with me to start with. I’m looking for an affordable solution that gets her on the road with me without driving for another company. I feel there’s a way around this without breaking the bank.
     
  8. Eddiec

    Eddiec Road Train Member

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    Try contacting your state trucking associations office - they may be able to offer you some ideas
     
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  9. ducnut

    ducnut Road Train Member

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    I believe, Great Western will insure new drivers.
     
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  10. North Pole Nightmare

    North Pole Nightmare Road Train Member

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    I had Great Western,bought through Joe Morten Insurance.Good company.
     
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