Hiring an employee? His truck under my authority or just him as a driver?

I see both sides of the coin... I actually had a pretty long talk with him to try to see his level of interest and even let him get a taste of what it is like and so far he has not been scared away and he realizes that he is making more here than he is at his other job. I was kinda going back and forth on putting him in one of my trucks or his before and it mainly came down to money and trust. I trust him but again nobody takes care of your equipment as good as yourself.

Question.... If I just keep him as a company driver and on an "as needed" basis besides having to keep a driver qualifications file, adding him to the drug testing pool, adding him on my insurance as a driver, etc. would I be able to treat him as a contractor and have him be responsible to maintain his own workers comp policy? Or will I actually have to treat him as an actual employee and cover workers comp?


At this point if I don't at least have another driver I am going to be losing jobs and I try to keep my dealers and brokers on lockdown with me.

 

The majority of the runs that I will need him to do would be short hauls with a max of 400 miles, the majority of the runs I would have him do would probably fall into the non-CDL 150 air mile provision so either way I think I will be able to keep him in HOS compliance this way. The only exception would be if I take him on a long trip with me to use him as a team driver.

I will have to see how they are running their drivers to see if he will fall into this category.

So 60% gross to him, I provide the truck and he pays the fuel... How about tolls? I am thinking he should probably pay those too since he can save time and use toll roads at my expense and some of the tolls around here can get crazy expensive per axle. If he avoids certain toll roads it may take longer but he will save money (the way I am thinking if he has to pay the tolls himself he will get wise on which roads to take).