Personally, I don’t think you need AI. All you need to figure out is an easy way for someone to track their write offs daily or weekly. Tell them taxes they owe on an ongoing basis. Dead simple.

Also, aside from this (which is nice!), if ppl keep having tax issues re: discipline/deposits, if you're rev is >$125K US, consider organizing as an S-Corp. Makes your personal taxes dead simple (do payroll through Gusto) still has plenty of tax/expense benefits.

Yeah..here’s what I think I would approach it. You want to make the one behavior stick. Every day send out an email asking if this is a write off and  the no of unsorted transactions. Once they finish show them how money you’ve saved on taxes.

Perhaps? I think a big issue for ppl going freelance is they think "I get to keep the company multiplier of my salary and losing of all the bullshit of being at a company"... except now you *are* the company. If you hate timesheets, being your own boss might not be optimal.

Part 3:  you got to deal with that behavior of poor financial mgmt early on, which is where every app fails. Turn sorting into a fun everyday habit.

The challenge in terms of finding value at $X cost is that unless you can hook into banking & CC software, this is potentially double work (depending on how you do your overall accounting), and errors come in. Unforch 'simple' bookkeeping & taxes is actually pretty tricky.

Oh yeah, this would absolutely use something like Plaid API to pull the transactions.

I agree strongly on the cost-to-value challenge though. How much freelancers would be willing to pay so that it's actually removes the tax burden? How much is ”yeah, this is worth it”.

Yeah Keeper is exactly that! From a few friends, I get a sense that everyone gets it, but nobody likes the manual work. So automated sorting kinda solves it.

I just know nothing about AI as a developer.

When you say about constraints, what are you thinking of?

I've a freelancer tax companion idea, but unsure if it's worth it.

A simple transactions tracker (both income & expense) that would give you profit/loss picture.

— tells you how much to pay taxes quarterly;
— prepares expenses sheet to enter into tax return.

Would you use it?

“Hey you've got 15 unsorted transactions” kind of email?

The tricky part is that if you're a 1099 freelancer (possibly even with W-2 job), likely you don't have a separate bank account for business.

Otherwise you're sorting through grocery and starbucks transactions?

There are no simple tools out there. I’ve done the homework on this one. People also need advice on the setup. Many mix things with their personal account. Come up with a process that’s easy.

This is great advice. Something @nickisnoble shared with me a while ago too.

Charging companies instead of individuals can be easier in some ways too, right?

There is absolutely a mkt for this; the sell is "we save you 2-3 billiable hours a month and only ask for 1 in fees" (I get this varies) but has to do everything, & do it well. Currently paying Fresh Books, Gusto and Quicken (don't ask). Would love to trade for single source.

This is a great idea. I just downloaded Keeper for my wife. Paid 20$ a month to create an expanse spreadsheet. I think both cost and user experience are constraints. I don’t know how many but a good chunk of them don’t put money aside for taxes

Part 2: A simple tool to just track write offs is worth $$$. End of the day, when you’re scrambling during tax time you’ll need this distilled information.

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