1099 legality for driver that picks their own loads and paid % of load?

One of the key issues that is not mentioned frequently. Does your so called independent contractor have any financial investment at risk in this enterprise? You do, you borrowed money for the truck, paying for the truck, so you qualify as independent contractor. But he has nothing at risk. He stops working, he walks away.
But as you have seen, it is muddy waters indeed. And widely abused.

 

The very first thing you need to do is determine what you are going to do to teach the driver how to work the landstar system. While this isn't hands off, the system needs more than a general "wait and see" load finding method. If you are already with them, then start by looking at who you are hauling for now and work the list and search feature on their load board to find active agents who can get your driver loads without them searching for them.


The start looking for a good contract lawyer, you will need a good contract, not a $30 legal zoom boiler plate contract. You need to sit down with the lawyer and with your own LS contracts to put together a solid contract that protects both you and the driver. Lawyers are not cheap, so expect anywhere from $500 to $1500 for this and believe me it is worth it.

With that, work out some numbers, I start with a 40/60 split, that's the start and the larger amount going to the person paying for fuel. The accessorial fees are spelled out in the contract of who gets what and why, lift gate and pallet jack isn't at 100% to the driver, it Is something from 75 to 90% of the fee collected to the driver, the amount take is for maintainance ... yes I am a cheap prick.

So an investment of $1500 is worth.

 

So question is what did the previous driver clear a week with this deal? On average.

 

Keep it simple, 1099. A good lawyer would want 1/3 of the cut.

 

First word in your thread header answers your own question.............
My advice and the advice of many other thinking people is
Consult a COMPETENT attorney!!
And remember, ................
You Get What You Pay For!
Look for an attorney whose area of expertise is in Trucking/Contracts/IRS Rules & Regs......Best of luck to you.

 

l send all info of money to CPA, they write your guy a check.
Or direct deposit, We do check cause, he or his wife can get it.
They take out taxes, and do the end of year filings

 

Just as a reference... I bought a 2016 Cascadia two weeks ago with 518K miles on it for $29K. Bought it from a Freightliner dealer. Came with a TriPak Evolution APU. I complained about a bald spot on one of the tires and they put eight fresh recaps on it. They ran the overhead for me. They let me plug in my DDDL software and run whatever tests I wanted. I even put it through a forced regen right there on the lot.

I live near that dealership and I haven't see another used truck move off the lot since I bought this one. You are right. It's not a good time to be selling a truck. It is a good time to be shopping for an upgrade if you're in a position to buy right now.