Ask AI Before You Buy Almost Anything

Ask AI Before You Buy Almost Anything

How to Spend Less, Ask Better Questions, and Avoid Being Rushed Into a Bad Decision

When my air conditioner died in the Florida heat, the repairman had the vocabulary. Condenser. SEER rating. Refrigerant. Line set. I had the heat, the checkbook, and the urge to make the problem go away. That's a bad negotiating position.

Instead of nodding along, I opened ChatGPT and started asking questions. Then better questions. The result wasn't dramatic. No passive income, no overnight miracle. It saved me about $3,000 on that one repair. That was the first real money I ever made from AI, and it was money I didn't waste.

This guide hands you the exact prompts that did it. Not generic "AI tips," but the specific questions that turn any chatbot into a second reader sitting beside you before you sign, click, or hand over a credit card:

• The one-line prompt that makes AI question you about your situation instead of just handing you a list
• How to find the "missing" cost or vague clause hiding in any estimate, warranty, or sales page
• Why the middle-priced option usually tells the truth, and how to make it prove it
• The Band-Aid Test: a real story about AI being confidently, repeatedly wrong, and why that matters more than you'd think
• A Printable Buying Sheet you can use for any expensive, confusing, or high-pressure purchase, before you pay

Written by Peeter Jakobson, M.D., a retired diagnostic radiologist with 40 years of reading fine print for a living. This isn't a guide about AI being magic. It's a guide about using AI to slow the moment down, ask the question the salesman hopes you won't, and keep the final decision where it belongs: with you.

Use it before the money leaves your account. That's the whole trick.