Driving for an o/op

Is the owner/op withholding anything when he pays you cause if he doesnt he's gonna 1099 you at the end of the year and YOUR gonna pay taxes on your gross earning's.

 

Play it safe and put back 10% of the cashiers check. If you don't get a 1099 you got a little splurge $.

 

Ask the owner/op if he's gonna 1099 you at the end of the year so you will know in advance. If J B withholds from you which I think they will and if you have some money coming in, kiss it all goodbye and some if you get a 1099 from the owner/op.

 

Being the "one thing leads to another" kind of guy I am, I'd be suspicious of that whole deal.

1. A cashier's check? Really? That's a hassle to do once in a while for a major cash purchase. Are you sure it's a bank check? or is it just computer printed or punched using a check embosser? If the company name is pre-printed on it then it's the latter. If you're not sure, ask your bank next time you deposit one.

2. If you're going to get a 1099, you should have filled out a W-9 form with your SSN or EID number on it. If he doesn't have your numbers, he can't file 1099 or W-2 on you.

3. If he's not doing any tax filings on you, what else is he not doing? Did you provide all the stuff that goes in a driver qualification and drug/alcohol file? Log book pages >14 days? If not, you may not be listed as an insured driver on a bad day. Or you could be camping a while or thumbing a ride at a roadside inspection or scale house on a not so bad day.

I hate to rain all over the tax-free pay deal you got going on. As hard as it is to keep a CDL and your day job when things are done right, my advice would be to insist on doing that weekend gig legit or don't do it. You could be at greater risk than a big tax due notice.

 

This is a wild guess, but maybe he does the cashier's check so there's no record of it in his company checkbook going to an individual. That way he can write whatever he wants to write for the $350 money going to the cashiers check, such as maintenance, cash, whatever.
My biggest concern is to make sure you're covered on his insurance when driving his equipment.

 

My concern is if you have a release from JBH to drive on the weekends. My guess is not. He would have had to contact them when doing the background check and drug screening. If he did none of this, and WHEN things blow up you will likely find yourself out of a job at JBH and un-employable as a driver.

I know that sounds harsh but you need to be doing one log book PERIOD. All it will take is an inspection for JBH to find out.