Payment UpdateWeek of Sep 28
Free software, paid operations. What one brewery learned in its first year on Square
TL;DR
A NerdWallet writer chose Square for her husband's brewery because it was $0 up front with published pricing and no contract. Within a year the brewery moved to the $49 Plus plan and paid an accountant to make a free integration work. She still calls it the right choice. The lesson is about total cost, not about Square.
What happened
NerdWallet's Hillary Crawford wrote about choosing a POS for her husband Justin's brewery in northern Michigan, which opened in 2025. Her article was updated on September 18, 2026. She picked Square because she did not want to invest a lot up front, because the software and hardware pricing is published, and because Square does not require a contract.
Then the first year happened. The brewery moved from Square's free plan to the $49 a month Plus plan, because the free plan could not split tips evenly across everyone working a shift. Square's QuickBooks Online integration is free, where Toast charges a monthly fee for it, but she still paid an accountant to make sure the integration was set up correctly and to separate sales tax and tips from the brewery's real income.
Her verdict: "Although there have been some hiccups with Square, I still feel good about the decision."
What it means for you
The bill was never the software. It was the year of small paid fixes around it: an upgrade for one missing feature, an accountant to untangle the sync, training time, a second device. None of that is on a pricing page, and it shows up no matter which logo is on the counter.
For a taproom or a cafe, the sticker price answers "what does it cost to open." The real question is "what does it cost to run," and that is a first-year number.
What to do
Write four lines before you sign. The software tier you will actually need by month six. Processing at your real volume, using the published rates for that tier. Hardware, owned or leased. And the people who make the integrations work: accountant, bookkeeper, whoever trains the staff. Compare vendors on that total.
Keep the published rates in front of you. On Square's current US pricing page the plans are Free at $0, Plus at $49 and Premium at $149 per location per month, with in-person processing at 2.6%, 2.5% and 2.4% plus 15 cents respectively.
Questions owners ask
Is this an argument against Square?
No. The author still recommends her choice. It is an argument for counting the first year, not the first month.
Why did the free plan not work for tips?
The free plan could not split tips evenly among everyone on a shift. That one feature moved the brewery to Plus.
Is a free integration really free?
The software fee can be zero and the setup still cost money. Budget for a professional to check the accounting sync in month one, before the first tax filing.
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