acallwood

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!

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

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

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.

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!

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

+1 =)

Hi gents - a little late to the party here, but yeah, tommynicholas is absolutely right here. We help you open an account with our bank (Lincoln Savings Bank) and your money goes into an account in your name at LSB. If anything were to happen (heaven forbid) this cash is secure and guaranteed.

If anything, you could make a solid case about a bank going out of business before anything. But all jokes aside, before building anything, security of funds is something we made sure our users feel really good about and we found a great partner to make sure your accounts and deposits are insured!

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!

Awesome to hear! We can't wait to have you!

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.

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.

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!

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!

1) https is life.

2)We are NOT from Nebraska, but we found an awesome tech-forward bank in Lincoln Savings Bank who saw a pain point in the 1099 world and got really excited about helping us build out a tax solution.

3) We don't automatically send quarterlies (yet) but we do send reminders and make it really easy to remit that payment every quarter. Shortly, you'll see an automated solution built into the product.

4) In answer to your W-2 question, yes, employers automatically withhold taxes for their employees and remit that money to the IRS throughout the year. Essentially the government holds on to this cash all year and if you've overpaid, you'll get a refund. This is what happens in a fair amount of W-2 job situations, but when you're self-employed, you're on the hook for taxes and are expected to separate funds and pay estimated quarterlies throughout the year - a tough thing to manage on top of client work, life, and whatnot.

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're finding that CPAs and freelancers alike are really digging what we've built thus far.

All in all, this is a product to help people like us solve the same problems we've run into over the years.

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.

Connecting two existing personal accounts is something we've considered, but we've found that this doesn't necessarily help saving from a user perspective. The majority of our users love that they now have an account that is out of sight and out of mind. We haven't ruled out other options, but the current setup has been pretty well received by our current our user base.

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. =)

We're fans of Free Tax USA. They have a pretty solid self-employment offering, but we found that we still run into the issue of having to manually save throughout the year for our tax obligation. If anything, we've always thought of our product as a compliment to some of the existing platforms out there for filing.

Totally - We handle withholding for your Federal AND State obligations. We collect a bit of information from you when you sign up and then our algorithm crunches based on your income and location.

As far as quarterlies go, we pass along reminders and quarterly filing instructions currently. In the near future, you'll be able to remit payment directly from our platform.

We'd love to have you this year. One of my partners got slammed with something like a $15,000 bill two years ago. That was the impetus for building out a platform to automate what's typically a pain in the ass.

Yep. I'm one of the founders and we all run our payments through Painless.

True story - our accountant sent me my personal bill last week and I had a heart attack until I remembered I have an account with cash in it specifically FOR my taxes this year. It was a "duhhh" kinda moment, but I've been so programmed as a consultant to freak out about 1099 taxes, so it was my default reaction even after spending the whole year building a solution.

Hey fellas,

ACe here from Painless1099 (www.painless1099.com). We automate tax withholding/filing for anyone earning 1099 income (think: freelancers and Uber drivers.)

We're thinking through growth specifically right now and are chewing on whether to go the B2B route or the B2C route. Different implications for both regarding scale and revenue obviously. We'd be stoked on a bit of help figuring out which to tackle first and how to make headway!

Thanks!

Just the standard: You created a startup application. You submitted your application.

with no additional information (just to clarify) or nothing at all? ?

Rejected folks: when you go to https://apply.ycombinator.com/ does it say anything?

When you go to apply.ycombinator.com does it say anything?

Head up!

Thanks @Deinos! Although, I'd agree with Tommy that the site itself IS silly - it's like dead stupid simple if we're being honest. Hell, as the co-founder I called Coffitivity ridiculous before we ever started building. That said, the utility becomes apparent pretty quickly and outweighs how trivial it seemed at first. We're really stoked you're enjoying it.