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Hey, it’s Jeffrey — back again!
Two contractor quotes sitting in my inbox. Both for a driveway extension and retaining wall. We're talking about a few thousand dollars here.
Here's the problem: they know way more than I do. They know what's standard, what's optional, what's necessary. I don't. I'm just trying not to overpay or pick the wrong person and regret it later.
One quote is $500 cheaper. Is that because they're more efficient... or because they're cutting corners I won't notice until it's too late?
And I've never worked with either of these contractors before. So I'm about to hand over thousands of dollars based on... trust? A hunch? The better website?
It's nerve-wracking. Sound familiar?
🤖 The AI Experiment
Instead of spending hours Googling construction terms or bugging friends in the industry, I fed both quotes into ChatGPT. Took me 5 minutes. Here's what happened — and why this might be the smartest money move I've made this month.
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💡 What AI Revealed (That I Never Would've Caught)
ChatGPT didn't just compare prices — it analyzed scope, flagged gaps, and spotted things I didn't even know to look for. Here's what it found:
💸 The cheaper quote was missing something critical
Quote #2 was $500 less... but had zero mention of drainage or backfill. ChatGPT flagged this immediately: "Proper drainage is crucial for retaining wall longevity." Without it, I could've been looking at water damage and costly repairs down the line.
🚩 The pricier quote justified its cost
Quote #1 cost more, but included a full drainage system with stone backfill — something I didn't even know to look for. AI explained why: water buildup behind a retaining wall can cause it to fail. Suddenly that extra $500 made total sense.
🧱 Material choice = aesthetic vs. structural trade-off
Quote #2 used nicer-looking interlocking blocks. Quote #1 used basic cement blocks. AI helped me see the trade: better curb appeal vs. better water management. Now I know which matters more for my project.
❓ Both quotes were vague in different ways
Quote #1 didn't specify wall dimensions. Quote #2 didn't explain ground prep or backfill materials. ChatGPT generated specific follow-up questions for each contractor — so I'm not going in blind.
⚙️ The Framework: How You Can Do This Too
Here's the exact prompt I used. Copy, paste, and replace with your own quotes:
💬 The Prompt:
I have two contractor quotes for the same project. I need you to:
1. Compare line items and flag any major differences in scope, materials, or labor
2. Identify anything that seems missing, unnecessary, or overpriced
3. Highlight any red flags or areas where I should ask follow-up questions
4. Tell me which quote seems more complete and realistic — and why
Here are the quotes:
[Paste Quote A - screenshot or text]
[Paste Quote B - screenshot or text]📎 Works for: Contractor bids, insurance policies, subscription plans, competing proposals, service agreements — anything with complex pricing.
Here’s a portion of the output:
You can see the full ChatGPT conversation here.
💡 Pro Tip
Don't just accept the AI analysis as gospel. Use it as a conversation starter. I'm now going back to both contractors with specific questions AI helped me surface — and I'll make a way smarter decision because of it.
🎯 What’s Next
Before I sign anything, I'm asking Quote #2's contractor to revise their bid to include proper drainage and backfill — so I can compare apples to apples.
And I'm asking Quote #1 about wall dimensions, block quality, and how deep their drainage system actually goes.
The 5 minutes I spent with ChatGPT gave me the knowledge to negotiate like I actually understand what I'm paying for — instead of just picking the cheaper number and hoping for the best.
💡 One Smart Read:
Speaking of leveling the playing field with professionals... Origin just released an AI financial advisor that scored 96.5% on CFP exams (human advisors average 79%). It connects to your actual accounts and gives you personalized advice on everything from portfolio allocation to life decisions.
Is this the first step towards replacing human advisors? Only time will tell.
🎯What to Do Now
✅ Save the prompt above for your next big purchase decision
💬 Have two quotes sitting in your inbox? Run them through ChatGPT today
📧 Facing an expensive decision this month? Reply and tell me what it is — I'll show you how to AI-analyze it in the next issue
📤 Know someone comparing quotes right now? Forward them this email
How did you like today's newsletter?
One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I’m not a financial advisor — just someone sharing ideas and tools I’ve found useful. Use what works for you, skip what doesn’t, and always do your own research before making financial decisions and using the tools shared in this newsletter.