Cranky on the Web – 1099s Aren’t Fun


In the Trenches: Making Sense of 1099sSmall Business Center
It’s tax time and that means it’s 1099 time. I hate dealing with 1099s.

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9 comments on “Cranky on the Web – 1099s Aren’t Fun

  1. Have you thought about a virtual mailbox service that scans your mail for you? I’ve been using VirtualPostMail – for a while because I needed somewhere to send my mail while I was being nomadic, but I’ve kept it open for receiving checks and tax forms.

  2. As a tax preparer, I probably hate 1099s even more than you do, because I end up getting stacks of documents that are basically useless to the bottom line number on a tax return but which I’m obligated to reconcile. Unfortunately, there really is nothing you can do about them. You can e-file 1099s, but the IRS still requires that you distribute copies to everyone you prepare one for. The best I can suggest – see if the vendors you send 1099s to will accept them in PDF format, and likewise, if you can convince people you receive them from to PDF them to you.

  3. I think the reason corporations are exempt is because it would be harder for them to cover up income to avoid tax. If they take your check to a check-cashing place, get cash, and don’t pay tax on it, someone will likely notice.

  4. Dealing with 1099s is an area where I like to apply part of the Getting Things Done approach: if it can be done simply and in less than 30 seconds, do it right away and get it off your mind.

    There are many good scanning apps for smartphones now, so it takes literally less time to create a good quality PDF than it does to walk over to a filing cabinet and find the right drawer. I scan all my forms as soon as I open the envelope, and then upload them to cloud storage. It takes about a minute per form, and then I don’t even have to worry about my dog drooling all over the folder and ruining everything!

  5. Not all LLC’s need to get a 1099. I always make sure to get a W-9 from everyone, even Staples. I won’t pay a vendor without one.

    Only the pass through entities get 1099s as an LLC, not the ones that file as a corporation.

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