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Comment by wdaher | Hacker News Reader

The first time we see something totally unknown to us, just like a normal human bookkeeper, we'll have to ask you about it (assuming there isn't metadata somewhere else that helps us categorize it).

But then once you've told us, unlike a normal human bookkeeper, we won't forget about it later — we'll actually encode a rule in our software that will enforce this check going forward.

(And yes, you also do benefit from "If our system has seen this type of transaction somewhere else, we can make a more intelligent guess")

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So let's say I have a $29.99 expense from AMAZON.COM and tag it as a marketing expense. Then I buy something else from Amazon tomorrow for $44.99.

Are you telling me that it gets automatically tagged as marketing? Because that seems... naive at best, and hugely problematic at worst (as it can result in a huge amount of expenses getting incorrectly tagged).

This is exactly why the human is in the loop and why the solution isn't purely software — to help come up with processes and mechanisms for resolving this sort of ambiguity.

(Every outsourced bookkeeper today has this challenge, and there are a variety of options for resolving it, depending on what the customer requires.)

Exactly what I came to ask, because I have at least a handful of vendors (perhaps more) that I have to key in across multiple categories.

Rules cannot be applied to these transactions. For the obvious ones, I already have automatic rules build right into QuickBooks Online.

What is different here?

My guess...they use quickbooks in the background, which allows you to upload receipts. If the description of your amazon receipt looks like furniture, then they'll mark it as such...if it looks like office supplies...office supplies.

I use Wave, which lets you upload receipts and it will perform OCR to extract vendor info, date, total cost. It's not much of a leap to go 1 step further and look at the line items and categorize...again just a guess.

> And yes, you also do benefit from "If our system has seen this type of transaction somewhere else, we can make a more intelligent guess"

Suppose User A has a bank entry "Payment to Stormy Daniels" and classifies it as "Hush Money".

User B also has a bank account entry "Payment to Stormy Daniels". Will the system suggest to User B that the entry should be classified as "Hush Money"?

@wdaher does Pilot help with invoicing? e.g. preparing and sending invoices, reconciling, etc?

Yes to reconciling, generally no to preparing/sending invoices, but it depends. (The Pilot Plus tier basically is "Let's talk to you and really understand your needs and put together a custom quote that makes sense given the work you want.")

Generally speaking we like to take on the work of the "monthly close" — i.e. making sure the books reflect what happened in your business the previous month, and we're less keen on doing stuff like following up with your customers who haven't paid, both because (1) that's something you probably want to have happen more than once a month, and (2) there's actually a lot of on-the-ground knowledge that you or the sales rep have that we may not have.

I see that pilot includes Quickbooks essentials. Wouldn't pilot just reference their customers to use quickbooks to handle the invoicing? And maybe some hand holding if needed...but otherwise it's DIY?

Yep, we generally point people at QuickBooks invoices or bill.com, but we have them do the inputting/sending of the invoices via one of those services.

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