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Friday Deep-Dive · Friday, August 14, 2026

I ran one of our ads through ChatGPT. Here's how to get it right.
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Trevor Slette

Trevor Slette

Co-founder, Quadd.ai · Reply to me at trevors@quadd.ai

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Friday Deep-Dive

I ran one of our ads through ChatGPT. Here's how to get it right.

At a webinar for Midwest Community Publications, two people asked me the same question in different words. A sales manager wanted to know why his proposals, sales one-sheets, and presentations come back with a different design every time. A publisher wanted a weekly real estate ad where the footer stays put and only the listing and the photo change. So this week I stopped theorizing and tried it on one of our own real estate ads. The first result was close but not exact, and fixing it taught me the real trick, which is not the one everybody assumes. Here is what happened, the one switch that changes everything, how to build it into a repeatable setup in ChatGPT, and what it costs if the free plan runs out on you.

I ran our own ad through ChatGPT. Here's the honest result.

A sales manager asked why his proposals and one-sheets come back with a different design every time. A publisher asked how to get a weekly real estate ad where only the listing and photos change. Same question. So I tried it on one of our own real estate ads. It came back close, but three things were off: the address spacing, the description font, and the Realtor and MLS logos, which it tried to draw from memory. That last miss is the clue to the whole fix, which is to stop asking ChatGPT to draw a new ad and start having it edit your real one. Below is what happened, the switch that fixes most of it, the step-by-step ChatGPT setup, how the same fix works on your one-sheets and proposals, and what the free plan will and will not get you.

This is the honest version of the AI-ad promise. It will not hand you a flawless ad on the first click, and anyone who says it will has not tried it on deadline. But with the right approach, editing instead of generating, plus a template you sharpen over a few weeks, you get a repeatable ten-minute ad that looks like yours. That beats a magic button that gives you something different every time.

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What is?

Project

What it is: In ChatGPT and Claude, a Project is a saved workspace that remembers your instructions and your files, so you don't have to re-explain yourself every time. You set it up once with your rules (your template, your tone, your logo, and what should never change), and every chat you start inside it already knows them.

Why publishers care: It's the difference between an AI that starts from a blank page every time and one that has your template memorized. For anything you make on a schedule, a weekly ad, a monthly one-sheet, a standard proposal, the Project is what turns “a different result every time” into “the same result every time.” Build the recipe once, then reuse it forever.

— Trevor

Trevor Slette

Co-founder, Quadd.ai · 28-year community publisher

trevors@quadd.ai · Book a 15-min call · LinkedIn

P.S. P.S. Reply “template” and I’ll send you the exact editing prompt and a fill-in-the-blanks template to drop into a ChatGPT Project, so your next listing ad starts closer to right.

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