The question I hear most after people's first pairing session isn't "what can AI do?", it's "which one do I pay for?"
There's no universal answer, and anyone who gives you one is selling something. But there's a way to find out cheaply. It takes one coffee, and it applies to any business.
Start with the work, not the model
Before deciding free vs paid, write down the five things an AI would actually do for you. Not the imagined things, the real ones: drafting a message to a supplier, summarising a day of emails, writing product descriptions, making sense of a CSV of orders.
Then test one of those five tasks on a free model. Honestly, the modern free models are good. Most small businesses discover that their daily tasks, short messages, summaries, spreadsheets, are handled fine by the free tier.
Three real endings
A bar owner needed menu descriptions, supplier notes, and staff shift messages. Free model. Never paid a cent, never needed to.
A freelance consultant lives on long, structured analysis, contracts, audit notes, client strategy documents. Paid model, every month, and it pays for itself in the first document.
A shop owner wanted to automate follow-ups. We decided the free model was enough for the copy, and the real investment went into the workflow, not the model.
The rule of thumb
"Pay only where it pays," is the whole rule. If you run a quick test, most of what a business types into AI is short, and short is free-tier territory. The projects that justify a paid tier are long, structured, or need serious reasoning, and you'll know you have one when the free version keeps fumbling it.
We pick all of this together in the first sitting. You won't pay me to sell you a subscription.