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Show HN: Painless1099 – automated self-employment taxes

painless1099.com

31–40 of 80 posts

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

#31

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 you guys make money and all - a $5 monthly fee for example, wouldn't be insulting. If you start talking about percentages, GTFO. And also data privacy and being clear that you do not profit off my data would also be important. Really just a…

Thanks for the feedback! We're going to be charging a subscription fee down the road, but right now we're just stoked to be sharing our build with the world. Anyone singing up in Beta will get free withholding for life, which is a solid perk if you ask me. I'm a little biased though. =)

Firstly, thank you for https everywhere. I see you have fees schedule here:

https://painless1099.com/home/fees

Are you guys from Nebraska? Did you just randomly pick Lincoln Savings Bank to partner with?

https://painless1099.com/public/docs/33611.pdf

just curious, do you automatically send withholding to the IRS automatically? I guess you make money with the withholding money you take in every paycheck but only transmit at the end of a quarter?

I never thought about this. Does an employer do the same with W-2? Assuming you have 100 employees paid monthly and you withhold $1 for each employee per pay month... For example, if the pay for the month of January would send me back $100 which the employer gets to keep That $100 until the end of March? And same for the pay period of February? Is this illegal? I've read that you can't do that with payroll tax but is income tax treated differently?

Sorry if these are stupid questions. I don't have a background in accounting.

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

#33
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 story about not having access to funds... I'd be very leery about putting an intermediary between my sole source of income and myself. Is there insurance? How do you know they're trustworthy?

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

#34
post #33

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 story about not having access to funds... I'd be very leery about putting an intermediary between my sole source of income and myself. Is there insurance? How do you know they're trustworthy?

The accounts are FDIC insured and held in an accredited bank according to the website. $250k of insurance per account.

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

#35
post #33

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 story about not having access to funds... I'd be very leery about putting an intermediary between my sole source of income and myself. Is there insurance? How do you know they're trustworthy?

The accounts are FDIC insured and held in an accredited bank according to the website. $250k of insurance per account.

Ok 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 that I'll give it back to you though--FDIC won't apply.

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

#36
post #32

"Confirm Password must contain an uppercase and a lowercase letter, a number, and must be at least 8 characters long" C'mon.

strict password requirements are usually a requirement for regulated businesses (such as those creating back accounts). Having a secure password for an account that manages your money is a good thing!

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

#38
Comment about your marketing website: I browse with cookies and localStorage disabled, and when I visit your site it's completely blank. I understand that if I were to create an account, log in, and utilize the functionality of your app that cookies (and/or localStorage) would be a requirement, but I don't understand why the marketing content wouldn't show up at all.

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

#39

This 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 separate savings account. I guess I don't see what value this adds?

There are a handful of people who are in the same boat you are and handle their taxes on their own with no problem. That said, for the vast majority of us, setting money aside and not touching it is really (like, REALLY) hard. Painless gets cash from freelance gigs out of sight and out of mind before you feel like it's money you should dip into. Beyond that, the automation of a process you'd have to do manually otherwise is something we think everyone can get behind whether you have a process in place currently or not.

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

#40

If they could take care of also making quarterly IRS payments, so I avoid the underpayment penalty, this would be quite nice.

There's a system for this already, sign up for EFTPS and the Treasury Department will automatically schedule and take out estimated tax payments. I just set mine up for next tax year and it's easy. Their website is awful and stuck in the 90's but it does work. https://www.eftps.gov/eftps/
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