Are You Asking ChatGPT the Right Questions?
Are you using ChatGPT to become a smarter real estate investor? And if you are using it, are you asking it the right questions?
I left a full-time software development job in 2004 to build wealth through real estate. I know how hard it is to get clear guidance when you’re starting out, and I also know how powerful it can be when you frame your questions the right way. I didn’t have tools like ChatGPT, but now – even with well over a decade of experience – I’ve started using it as an advisor to help walk me through my options.
In today’s article, I’ll show you the entry levels of what it looks like to use ChatGPT as an advisor, I’ll show you what happens what happens when you ask it how to make $10,000 a month in real estate, and then I’ll walk you through how to sharpen your prompts so the answers aren’t just broad lists, but focused strategies that fit your goals and situation.
Start With the Big Question, Then Break It Down
The first question I asked ChatGPT was, “How do I make $10,000 a month with real estate?” If you drop that into ChatGPT, it will give you a long list of strategies:
- Rental properties
- Single-family and multifamily
- Real estate syndications
- Flipping houses
- Short-term rentals
- Commercial properties
- Triple net leases
- Self-storage and mobile home parks
On the surface, that’s useful. There are 8 strategies that you could potentially make $10K/month with. But as an investor, you don’t need “all the strategies.” You need the one or two paths that match your resources, timeline, and risk tolerance.
The problem is that ChatGPT won’t automatically pick the best option for you. Its default mode is broad. That’s why you need to take the next step: refine your prompt so it evaluates each strategy based on your situation
Add Context to Get Better Guidance
Now let’s add just a little bit more context by following up with, “What’s the timeline for reaching $10,000 per month if I work 40 hours a week as a software developer?”—the answers became much clearer. Here’s what it will respond with:
- Rental properties: 5–10 years, because each property may only net $300–$500 per month.
- Multifamily apartments: 2–5 years, if you actively learn syndications. This requires raising capital, underwriting deals, and asset management.
- Passive syndication investor: Immediate income, but only if you have $1 million or more to invest upfront.
- Flipping houses: 3–5 years, assuming one flip per quarter at $25–100K profit. Produces large chunks of cash but not steady monthly income.
- Short-term rentals: 1–3 years, if you acquire 4–6 units in strong markets. Each could net about $2,000 per month.
- Self-storage or mobile home parks: 3–7 years, but require significant upfront equity and more management if you’re the operator.
Even with that tiny amount of additional context: your profession, hours, and salary, you can get an estimate on the timeline depending on which strategy you choose. Some strategies immediately fall off the list because they don’t fit your capital or time. Others rise to the top as realistic paths worth exploring.
Why Better Questions Create Better Strategies
But I don’t think you should stop there because you’re still stuck with multiple answers. That’s because it doesn’t know your personal preferences, risk tolerance, or end goals unless you tell it.
For example:
- Do you want active income or passive?
- Do you have capital saved, or are you starting from scratch?
- How much time can you realistically invest outside your job?
When you add those details, ChatGPT starts acting less like a list-maker and more like an advisor. It helps you eliminate dead ends and focus on strategies that align with your unique situation.
That’s why I always use a system when prompting ChatGPT. A structured approach gets you stronger, more specific answers—whether you’re talking about real estate, business growth, or any decision where clarity matters.
Looking Ahead to Your Next Step
ChatGPT is only as powerful as the questions you ask. Broad questions give you broad answers. Focused questions give you focused strategies.
When you frame your prompts with context—your goals, your timeline, your resources—you transform ChatGPT from a search engine into a true advisor. And that’s when it becomes a tool to help you not just learn about real estate, but actually move forward as an investor.
This article is actually part 1 of 3 about the topic of using ChatGPT to invest in real estate. In my next piece, I’ll share the exact framework I use every time I prompt ChatGPT. It’s a repeatable prompt template you can copy and paste and then fill out yourself.
You can access Part 2 here. I also have a video series you can watch here.
To your success,
Michael Blank
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