So 2015 was my first full year in the real estate business.  Someone published an article a week or two ago about making sure we get our 1099s together out to our contractors and such.  I honestly didn't know I had to do that, so I called my CPA and asked about it.

I told him that I had a roofer guy do 2 roofs for me (I paid him over 10k) and my main contractor which I paid 27k+ last year.

My CPA suggested I 1099 both of those guys, and to try to get their SSN but if not, still 1099 them to protect the business.

I called my contractor and he was ok with it, although he acted a little surprised I was asking.  He even gave me his SSN.  

The roofer,  I didn't bother to even ask.  He's a roughneck type and I knew he would not be happy.  So I just got the phone call.  I saw his name pop up, and I 'gulped' lol.

I'm not sure he was even aware of what the 1099 was, but he was livid. I  couldn't even get a sentence in without getting cut off repeatedly about how I'm acting like he's done 15 roofs for me and "I've done several others for everybody else and nobody's ever 1099'd me".

When i asked if I could explain what the paper was and why I had to issue it he just cut me off and said he didn't care to hear it.  At the end he told me to lose his number and never call him again.

Did I do anything wrong?  Should I not have sent him one?  I was just trying to protect the business and do the right thing.  I lost a good, cheap roofer over it, too.