Running as a independent contractor taxes

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To simplify it, you would pay both the employer and employee share of the income taxes. This is approx. 30% of gross, adjusted for any legitimate expenses. This is a very basic description but it gives you an idea.

That said, other things to think about is no workers compensation or unemployment insurance, so if you get hurt or laid off you are on your own. In many cases these are not legitimate, to be paid as an independent contractor certain conditions must be met, which many don't. I won't get into the right or wrong of 1099 vs. W-2, there are many angles to it and each work better for some people.

Bottom line, make sure the pay is exceptionally good to allow you to cover your taxes and insurance, plus make sure you know the risks you take. Keep in mind, on 1099 you need to put away your money for taxes and will end up writing a check to the IRS, no one is going to withhold and submit on your behalf. This burns many folks, they don't have any money put aside when taxes come due and are shocked that they have to pay, they usually are expecting a tax refund like the average employee does.

 

So you are willing to run as a 1099, but unless you meet a very narrow defined criteria you will be running illegal.
If the "owner" is willing to pay illegally where else is he willing to break the law?
Truck maintenance? "You can run bald tires in the snow, nothing wrong there."
HoS? "Just run the load, we'll make it look right tomorrow."
Pay? What, you expect us to pay you? So sorry, sue us!
Get hurt? ... Well, the list goes on.

If the slight chance of him being legal is true, go to a CPA as you are now a business dealing with another business.