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Show HN: Painless1099 – automated self-employment taxes

painless1099.com

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Re: Show HN: Painless1099 – automated self-employment taxes

#71

Post by acallwood »

trentbigelow wrote: post #63

I think Painless1099 IS on to something: taxes for freelancers are a pain, and no one wants to learn how to do it. However, I think asking some people to change their bank accounts is going to be resisted. Also, waiting an additional 2-3 days to access your money when you're living paycheck to paycheck (as most independent contractors are) is not an option. My cofounders and I are working on solving this same problem…

Love what you guys are doing and would love to chat sometime, Trent! hello@painless1099 will do it if you're interested!

Re: Show HN: Painless1099 – automated self-employment taxes

#72

Post by acallwood »

melvinmt wrote: post #19

I'm a 1099-consultant and whenever a payment comes in, I just update a spreadsheet and transfer the amount to a separate savings account. It's not that big of a pain really, just takes a couple of minutes, but it would be nice to automate this with your service. The only reason I'm hesitant to switch is because you're offering this for free. How do I know you're still going to be in business in a year from now? In ot…

Hi there! It's free for now as we offer perks for signup. We'll shortly roll to a subscription based service for access to tax withholding. We'll also introduce some premium features down the road to continue automating the tax portion of your consulting. Hope that helps!

Re: Show HN: Painless1099 – automated self-employment taxes

#73

Post by acallwood »

rwhitman wrote: post #69

A tool that does automatic withholding of business deposits in a savings account for taxes is something I've been dreaming of for a while, to the point where I even sat down for a bit to see if I could cook up my own tool to do it. Alas banks do not exactly go out of their way to expose a money transfer API... This sounds exactly like what I wanted.. but I don't know if I want to be the early adopter guinea pig for s…

Thanks for the feedback! FWIW, with Painless, your money is always accessible to you as it's in an FDIC Insured savings account. If (heaven forbid) we're not around in the long term, your cash is insured up to $250,000 and your new savings account is in a well-established financial institution at Lincoln Savings Bank. Really what we've done is use existing infrastructure to automate transfers that you'd be making manually, whether between two accounts in your existing institution or two accounts at separate ones.

Re: Show HN: Painless1099 – automated self-employment taxes

#74

Post by acallwood »

icodestuff wrote: post #66

Does the account earn interest? Right now I have an Ally savings account I transfer a percentage of my revenues every two weeks, so I'm earning 1% on my tax bill. It's small, but not irrelevant.

Currently these accounts do not earn interest. This may change in the future, however!

Re: Show HN: Painless1099 – automated self-employment taxes

#76

Post by whiddershins »

acallwood wrote: post #43
meesterdude wrote: post #28

Earlier quoted context omitted.

Actually it comes out to $60/yr, which isn't bad for just splitting off funds between two accounts. Obviously they could charge more - $10/mo wouldn't be bad either, still worth it there, which is $120/yr. But it's not worth $100/mo, or 2% of my gross income, for example. I didn't make so much as a freelancer that i could tolerate either of those financially. And It doesn't remove the need for a CPA, just helps with…

Our planned price point rolling out of beta will be $9.99 monthly, which puts you right in the $120 annual range as you mentioned. And you're absolutely right, we don't remove the need to have a CPA, we DO, however, reduce the time you need to interact with your CPA and make it really easy for them to do their job. Given the hourly rate of my CPA, I've paid for Painless if I can reduce his work by almost an hour. We'…

FWIW my CPA charges a flat fee ($350, in NYC, which is an expensive city) and does a lot for that fee. My taxes are complicated. I don't think this is uncommon, although I may have a discounted price.

Regardless of mechanics or feature set discussed elsewhere in this thread, selling me on an extra $120/year is an increase of 30% to my hard cost of dealing with taxes per year.

Re: Show HN: Painless1099 – automated self-employment taxes

#78

Post by acallwood »

xivzgrev wrote: post #70
toddmorey wrote: post #52

Earlier quoted context omitted.

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…

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

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

Re: Show HN: Painless1099 – automated self-employment taxes

#80

Post by acallwood »

jMyles wrote: post #79

This looks like nearly the tool I need: what I'm really looking for is a program that allows me to keep track of deductions and their reasoning. Also, some kind of facilitated back-and-forth with a CPA will be amazing?

Hey thanks for the feedback! We're building a small network of CPAs to allow you to get feedback in real time on some of our more nuanced tax question. Expenses and deductions you can expect to see down the road as well!
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