Painless1099
Web and SaaS
tax savings for freelancers
SHOW HN2016
92points
78comments
#414of 2,264 in 2016
Top 19%of 2016 by points
How HN took it
DebatedReal support and real criticism
17 positive, 23 neutral or asking, 2 mixed, 17 critical, out of 59 comments about the project. Thread score -0.18.
Idea: 11 for, 6 againstPrivacy: 2 for, 3 againstPricing: 0 for, 3 againstDesign: 0 for, 3 againstExecution: 0 for, 2 against
The thread, comment by comment
Each row is a top-level comment and its replies, in HN's order. Select a cell to open that comment on HN.
positive neutral or mixed critical about another commenter or something else the maker
What HN said
What people liked
Commenters say the tax-saving problem for 1099 workers is real and painful
From 4 comments
First off, let me echo what an amazing pain in the ass it is to be a 1099er, and how big a deal this can be for people. Kudos there. I'd ask for a little more transparency on how…
meesterdude on HNMan, if this would've been around a year or so ago! The whole 1099 process was by far the biggest pain point for me of being a contractor/sole proprietor. What led you to address…
pumblechook on HNfantastic idea. I consistently get screwed over at the end of the season for not preparing my taxes correctly. I'll be signing up.
elliotroth on HNOh man, i wish this had existed 5 years ago when I first started contracting. Estimating my taxes, doing withholdings, etc. was just a nightmare for me. I might look into this if…
antjanus on HN
Automatic withholding and free beta perk appeal to some users
From 3 comments
fantastic idea. I consistently get screwed over at the end of the season for not preparing my taxes correctly. I'll be signing up.
elliotroth on HNOh man, i wish this had existed 5 years ago when I first started contracting. Estimating my taxes, doing withholdings, etc. was just a nightmare for me. I might look into this if…
antjanus on HNThis 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…
jMyles on HN
Objections
Requires opening a new bank account and giving up control of income
From 3 comments
Man, if this would've been around a year or so ago! The whole 1099 process was by far the biggest pain point for me of being a contractor/sole proprietor. What led you to address…
pumblechook on HNA 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…
rwhitman on HNI 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…
trentbigelow on HN
Payouts delayed by a few days due to ACH processing
From 2 comments
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…
toddmorey on HNI 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…
trentbigelow on HN
Pricing and business model unclear; worry about the company staying in business
From 3 comments
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…
melvinmt on HNJust to be the devil's advocate, what happens if this company goes bust and your tax money is stuck in their account and inaccessible? The IRS isn't going to accept some sob…
tdicola on HNActually 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…
meesterdude on HN
Does not support checks, which many 1099 workers receive
From 2 comments
FWIW, the second account WOULD be out of sight out of mind. you would just deposit into it, and then money would flow from it into your actual bank account via the service.…
meesterdude on HNI 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…
trentbigelow on HN
Requests
Support for paying quarterly IRS estimated taxes automatically
From 2 comments
If they could take care of also making quarterly IRS payments, so I avoid the underpayment penalty, this would be quite nice.
gricardo99 on HNMan, if this would've been around a year or so ago! The whole 1099 process was by far the biggest pain point for me of being a contractor/sole proprietor. What led you to address…
pumblechook on HN
Expense tracking and deduction tracking
From 2 comments
Man, if this would've been around a year or so ago! The whole 1099 process was by far the biggest pain point for me of being a contractor/sole proprietor. What led you to address…
pumblechook on HNThis 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…
jMyles on HN
Support for check deposits
From 2 comments
FWIW, the second account WOULD be out of sight out of mind. you would just deposit into it, and then money would flow from it into your actual bank account via the service.…
meesterdude on HN> If you want to actually solve this for 1099ers, your going to have to do more than just what works for a subset of users; and supporting checks absolutely needs to be on your…
deuce42x on HN
Support for state and sales taxes
From 2 comments
This looks interesting. Can you go into a little detail about how well you currently cover state taxes vs. federal, quarterly payments, etc? The service I currently use doesn't…
bitdeveloper on HNThis is something I manage pretty easily without a lot of fuss using a spreadsheet and one bank account with my 1099 business. I do a small volume of transactions with higher…
jly on HN
Questions
What is the business model and how does the company make money
From 3 comments
First off, let me echo what an amazing pain in the ass it is to be a 1099er, and how big a deal this can be for people. Kudos there. I'd ask for a little more transparency on how…
meesterdude on HNFrom 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…
toddmorey on HNI'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…
melvinmt on HN
Who owns the account and how is FDIC insurance applied
From 3 comments
Just to be the devil's advocate, what happens if this company goes bust and your tax money is stuck in their account and inaccessible? The IRS isn't going to accept some sob…
tdicola on HNOk but who owns the account and how do you know they're trustworthy? I could open a bank account anywhere and ask you to start depositing your income there. You have to trust…
tdicola on HNEach account is a separate, FDIC insured account held with Lincoln Savings Bank. Your account is your account, there is no money pooling done. Painless 1099 is a front end to…
tommynicholas on HN
Does the savings account earn interest
From 1 comment
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…
icodestuff on HN
Alternatives named
Track.tax
From 2 comments
Check out https://www.track.tax It works exactly as you described- money goes into your account first, then taxes are calculated and moved to your tax savings account. You can…
clabasky on HNI 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…
trentbigelow on HN
QuickBooks Self-Employed
From 1 comment
Fwiw I use and am actually quite impressed with Quickbooks Self-Employed version, and I've never had a problem with 1099 management. They keep tax estimates for you in the…
mrchess on HN
Digit
From 1 comment
It's basically like Digit, but instead of helping you save, it's helping you withhold
xivzgrev on HN
Zen99 (closed)
From 1 comment
A company doing something similar closed down last year: https://www.crunchbase.com/organization/zen99
baus on HN
Spreadsheet and separate savings account
From 3 comments
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…
melvinmt on HNI never really considered this an issue. I've been self-employed since 2012 and kept a spreadsheet that calculated the quarterly payments I need to make, so I just sent that…
EddieRingle on HNThis seems like something that is easy for me to do myself. I deposit a check in my bank account and either manually or automatically move some percentage of the money to a…
Ajdeanmny on HN