Show HN: Painless1099 – automated self-employment taxes

Re:Show HN: Painless1099 – automated self-employment taxes by toddmorey on Tuesday April 19, 2016 @04:59PM (#11530365)

From the FAQ: "For now, we make small returns of interest on the money held in accounts. If we offer a Painless1099 Debit Card, which will allow us to track expenses, then everytime you swipe the card, we will get a small cut that is generally charged to a vendor."

I think the hard sell will be getting contractors to accept that payment will be delayed three more days by use of this service. A lot of clients pay late or require a bit of time and management to get your money.

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Re:Show HN: Painless1099 – automated self-employment taxes by acallwood on Tuesday April 19, 2016 @05:32PM (#11530637)

You're totally right here, the time it takes for ACH to process is a tough wait. We're working on a few ways to speed up the process, but the way we think about it right now is that waiting an extra day or two is better than owing several thousand bucks because we couldn't be bothered to set cash aside and pay quarterly taxes. There's always a bit of a trade off with these things. As we grow, we're hoping to make the process 100% seamless, but figured we'd tackle the core of the problem to start and build out from there.

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Re:Show HN: Painless1099 – automated self-employment taxes by xivzgrev on Tuesday April 19, 2016 @06:39PM (#11531049)

It's basically like Digit, but instead of helping you save, it's helping you withhold

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Re:Show HN: Painless1099 – automated self-employment taxes by acallwood on Tuesday April 19, 2016 @11:05PM (#11531996)

Yep. Digit takes cash out of the back end, whereas we focus on helping you squirrel it away up front before you see it.

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