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?

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

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?

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.

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.

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.

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.