17 Bookkeeping Tips I Wish Someone Had Told Me When I Started My First Business

I still remember the day I opened the shoebox.

It was 2012, and my little screen-printing shop in Milwaukee had been running for six months. The shoebox sat on the corner of my desk like a guilty secret—receipts, crumpled invoices, a couple of coffee-stained bank statements, and one mysterious Post-it that just said “Pete—$47.” I dumped the whole mess onto the table, convinced I’d sort it in an hour. Three hours later I was on the phone with my cousin, an accountant, begging for mercy.

That shoebox taught me more about bookkeeping than any textbook ever could. Over the next decade, I grew the shop, sold it, started Midwest Bookkeeping LLC, and now help dozens of Wisconsin businesses keep their numbers straight. Along the way I collected a handful of tips—some obvious in hindsight, others hard-won—that save time, headaches, and (occasionally) actual jail time.

Here are 17 of them.

1. Separate the spaghetti before it cooks. Open a business checking account the day you file your LLC paperwork. I didn’t. For three months every Dunkin’ run and every T-shirt sale went through the same debit card. Come tax season, my accountant charged me an extra $800 just to untangle personal groceries from wholesale ink. One account for business, one for personal. Non-negotiable.

2. Snap first, sort later. Every receipt gets photographed the moment it lands in your hand. I use the Expensify app because it reads the numbers automatically, but even your phone’s camera roll works. The IRS doesn’t care if the paper fades in your glove box; they do care that you can produce proof.

3. Code expenses the same week they happen. Friday afternoons are sacred. I pour a coffee, pull up QuickBooks, and categorize every transaction from the prior seven days. Waiting until the end of the month turns a 20-minute job into a three-hour archaeological dig.

4. Reconcile like you’re balancing a checkbook in 1985. Every month, without fail, match the bank statement to the books line by line. I once found a $1,200 duplicate charge from a supplier because the decimal point got entered wrong. That single reconciliation paid for a year of my QuickBooks subscription.

5. Treat sales tax like radioactive material. Collect it, segregate it, and never, ever spend it. Set up a separate savings account labeled “Sales Tax—Do Not Touch.” Wisconsin’s Department of Revenue will audit you eventually; when they do, you’ll sleep better knowing the money is already waiting.

6. Invoice the same day the job is done. I print tees. The second a customer picks up their order, the invoice goes out. Net-30 turns into Net-Whenever if you wait. Fresh invoices get paid 11 days faster on average—my own data, tracked in a Google Sheet for four years.

7. Automate the boring stuff. Link your bank feeds to your accounting software. Link PayPal. Link Square. Every night at 2 a.m. the transactions drop in like magic. I still review them, but the heavy lifting is done while I’m asleep.

8. Name your chart of accounts like you’re naming children. “Supplies” is too vague. “Screen-Printing Ink—Black” and “Screen-Printing Ink—Red” tell me exactly where money leaks. The first time I ran a profit-and-loss by ink color, I switched suppliers and saved $400 a month.

9. Keep a “Suspense” account for mysteries. That $47 Post-it from Pete? Into Suspense it goes. Every quarter I clear the account. Nine times out of ten the mystery solves itself; the tenth time I write it off as “owner education.”

10. Track mileage the old-school way if apps fail you. I tried three mileage apps. All three drained my battery and double-counted trips. Now I keep a cheap spiral notebook in the truck console: date, purpose, starting odometer, ending odometer. The IRS accepts it, and I don’t fight technology.

11. Pay yourself a salary, not random draws. Random owner draws make tax time feel like Russian roulette. Set a modest monthly salary, run it through payroll (even if it’s just you), and let the rest stay in the business as retained earnings. Your future CPA will send you a fruit basket.

12. Plan for quarterly estimated taxes from day one. Wisconsin wants its cut four times a year. I stash 25% of every invoice into a high-yield savings account labeled “Tax Man.” When the voucher comes due, the money is already bored and waiting.

13. Use job costing even if you think you don’t need it. A local brewery hired me to print 500 pint glasses. Materials $1,200, labor $800, my fee $2,500. QuickBooks job costing showed the real profit was $420 after electricity, spoiled screens, and my time. Next quote went up 30%. The client still said yes.

14. Back up your books like your life depends on it. QuickBooks Online backs up automatically, but I also export a PDF of the general ledger every December 31. I email it to myself and save it on an external drive. Hard drives fail; paranoia doesn’t.

15. Talk to your accountant before you buy anything big. I almost leased a $40,000 automated press in 2018. A 15-minute call revealed I could depreciate only 20% in year one. Bought a used machine for $18,000 instead and wrote off the whole thing under Section 179. That conversation saved me five figures.

16. Review your profit-and-loss monthly, even if it hurts. Some months the report is ugly. Ink costs spiked, a big client paid late, whatever. Facing the numbers forces decisions—raise prices, cut overtime, chase receivables. Ignoring them just kicks the pain down the road.

17. Teach one employee the basics. When I sold the print shop, my lead designer knew how to enter invoices and run a receivable report. The buyer paid an extra $10,000 for the business because it wasn’t 100% dependent on me. Redundancy is leverage.

I still have that original shoebox. It sits on a shelf in my home office, empty now, a reminder of how far a little structure can take you. Bookkeeping isn’t glamorous, but it’s the difference between guessing and knowing, between surviving and thriving.

Pick one tip from this list and implement it this week. Then pick another next week. Seventeen weeks from now you’ll look back and wonder why you ever let the spaghetti cook in the first place.

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(Note: This post is written from the first-person perspective of the owner of Midwest Bookkeeping LLC, drawing on real-world experiences in Wisconsin small-business finance. All client examples are anonymized or aggregated.)