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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

#51

Post by acallwood »

jessedhillon wrote: post #30
gk1 wrote: post #27

Is it really that difficult to put away 30-40% of every payment towards taxes? Not trying to be cynical, just having a difficult time understanding why a service is needed to perform a routine transfer.

There's a lot of value in being able to hone in on the exact figure -- 31.8% based on your previous year's income and deductions -- giving you an extra 9.2% if you were conservative and putting aside 40%. I don't know if that's what this service can actually offer, just putting out there that it's more complicated than just setting aside a gross estimate like that.

Totally right - We withhold exactly the amount you need to set aside, as opposed to just blindly ballparking it as we've all done at some point (if we separated taxes at all). Taking the guesswork out of the amount we should be setting aside is a big piece of why we built Painless!

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

#52

Post by toddmorey »

meesterdude wrote: post #13

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…

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.

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

#53

Post by mrchess »

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 upper-right corner so you always know around how much you will need to pay, and you can pay the quarterly taxes online through them via. eftps. While they don't auto-save for you, I'd argue you should be responsible enough to do this yourself. They were a bit buggy when they first released, but their support was pretty good to me and they have fixed all issues I've reported.

That being said, I'm not sure what this product can do for me over what I'm using now.

Actually, I just looked at their FAQ and they don't track expenses or anything... things you can do with Quickbooks.

Now I'm not trying to down this company, but just am pointing out to others that a mature version of this product already exists (minus the auto-save) and that I can't identify "why" I should switch over to Painless.

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

#54

Post by acallwood »

gk1 wrote: post #27

Is it really that difficult to put away 30-40% of every payment towards taxes? Not trying to be cynical, just having a difficult time understanding why a service is needed to perform a routine transfer.

Yep - this is pretty tough for the majority of independent contractors. Simply figuring out how much to save is the first issue, but the larger issue is ACTUALLY separating funds from your regular checking account so you don't spend these funds that should go to the IRS every quarter. We built Painless to automate what (admittedly) should be a "routine transfer" but often isn't and becomes a problem at the end of the year when we owe a huge bill that sucks to pay outright. The convenience of automating money movement is the big piece of what we do for our users. Hope that helps!

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

#55

Post by acallwood »

mrchess wrote: post #53

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 upper-right corner so you always know around how much you will need to pay, and you can pay the quarterly taxes online through them via. eftps. While they don't auto-save for you, I'd argue you should be responsible enough to do this yourself. They…

It's really the automation part that we drilled down on. To be honest, we love QBSE and don't consider them competition as much as we see them as a compliment to what we do. Tracking your tax obligation is great, but we take it a step further and just automate the cash that should be transferred out of your every day account and into one that you're less tempted to spend from. For a large portion of our 1099 peers, we see that the savings aspect is either A) hard, or B) a process that, if automated, could free up time to actually focus on work rather than having to actively (and manually) manage your taxes.

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

#57

Post by tumblen »

ents wrote: post #32

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

The real problem is banking sites that say, "Your password must be less than 12 characters and must not include symbols."

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

#58

Post by acallwood »

toddmorey wrote: post #52
meesterdude wrote: post #13

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…

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…

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.

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

#60

Post by acallwood »

baus wrote: post #46

A company doing something similar closed down last year: https://www.crunchbase.com/organization/zen99

Hey guys! We're pretty familiar with the zen99 crew. For the most part, they were thinking about the same world as we are, but were tackling the problem a little differently.

I think as founders, we have a really bad habit of pretending out competitors are stupid and operating as if they didn't know what they were talking about. That's rarely the case in general, and certainly not the case in this instance. Tristian (CEO of zen99) wrote an awesome post mortem, which I think was just shared below, and it's been really helpful for quite a few of us in the fintech space. Continuing to read and build on the lessons that companies have learned before us is a big part of why we built the product we did as opposed to trying to replicate zen99 and hope it worked out for us. We really appreciate this thread and you guys pointing out the similarities between our companies!

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