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Re:Show HN: Painless1099 – automated self-employment taxes by dd36 on Tuesday April 19, 2016 @11:10AM (#11527519)
Could also be useful to partners in an LLC that can't be paid by W-2.

Smart idea.

Re:Show HN: Painless1099 – automated self-employment taxes by acallwood on Tuesday April 19, 2016 @01:46PM (#11528729)
Yep. I'm one of the founders and we all run our payments through Painless.

True story - our accountant sent me my personal bill last week and I had a heart attack until I remembered I have an account with cash in it specifically FOR my taxes this year. It was a "duhhh" kinda moment, but I've been so programmed as a consultant to freak out about 1099 taxes, so it was my default reaction even after spending the whole year building a solution.

Re:Show HN: Painless1099 – automated self-employment taxes by lojack on Tuesday April 19, 2016 @01:38PM (#11528656)
Last year I was hit with a massive IRS bill I was completely unprepared for. Saved some money, but not nearly enough. Something like this would have absolutely saved me.
Re:Show HN: Painless1099 – automated self-employment taxes by acallwood on Tuesday April 19, 2016 @01:47PM (#11528743)
We'd love to have you this year. One of my partners got slammed with something like a $15,000 bill two years ago. That was the impetus for building out a platform to automate what's typically a pain in the ass.