Three months open and my books are a mess I don't know how to unpick

Greg Foster· Vintage and resale clothing store, pop-ups first, storefront open three months· Open, Retail & Resale·3w

The store has been open since the summer and it's doing better than I expected. What isn't doing well is everything behind it.

I ran pop-ups for two years out of a personal account and a card reader, and when the store opened I told myself I'd sort the money side out properly. I didn't. There's one bank account. My rent, my inventory buys, my daughter's braces and about four hundred dollars a month in cash sales all live in it. The cash is the part that scares me most, because a chunk of it went straight back out to buy stock at estate sales and I have receipts for maybe half.

Sales tax I did register for, at least, and I've been collecting it. I haven't filed yet and the first due date is coming.

I know the answer is get a bookkeeper, and I will. What I'm trying to work out is whether I hand someone this mess or clean it up first, and whether there's any point reconstructing the cash purchases or whether I just start clean from today and accept that year one is what it is.

Anyone untangled a year like this? How far back did you bother going?

4 replies

Cheryl Dunn· Open·3w

Hand it over messy. I promise you can't clean it in a way that helps me, and the half-cleaned versions take me longer than the raw ones because I have to work out what you already touched. Bring the bank statements, the card reader exports and whatever receipts exist in a shoebox, and be straight with me about the cash.

On how far back: in my experience it's worth reconstructing the current year and drawing a line before it. Estate sale purchases with no receipt aren't hopeless either. A dated note of what you bought, where, and for how much, written at the time in a notebook, is a great deal better than nothing.

Open the second bank account today though. Before the bookkeeper, before anything else.

Greg Foster· Open·3w

Second account opened this morning. It took eleven minutes and it's been on my list for three months. I've also started a notebook in the van for estate sale buys, which feels almost too simple to be the answer. Calling two bookkeepers this week and bringing the shoebox exactly as it is.

Aisha Wright· Open·3w

I'd move the sales tax piece to the top of your list, above the bookkeeping. Filing on time with a slightly ugly number is a very different situation from filing late, and late is where it gets expensive. Mine is a quarterly filing and the portal is genuinely unpleasant, but it takes me an hour now that I know where everything lives.

Also check what your state says about months where you owe nothing. Where I am you still have to file a zero return, which I found out the annoying way.

Rob Mackenzie· Open·3w

Third business, and my books have been a disaster exactly once, which was enough. What fixed it permanently wasn't discipline, it was making the mess impossible. Separate account, one card that is only the business, and everything through the reader whether they're paying cash or not.

That last one matters for you specifically. Cash sales you ring through the reader as cash still show up in a report. Cash sales you put in your pocket exist nowhere. It isn't about honesty, it's about you being able to see your own month.

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