How AI Is Quietly Reshaping My Real Estate Investing Workflow

You might already know what AI is. Maybe you've used ChatGPT to draft an email or asked Claude to summarize a 50-page OM. But here's the real challenge: making AI not just a novelty, but a reliable part of your investing process. Not as a gimmick, but as something that consistently improves how you operate—from due diligence to investor communication.

That’s where things get interesting.

Because once you stop treating AI like a novelty and start using it like an actual team member—a research assistant, a stress-tester, a writing partner—it doesn’t just save time. It improves your thinking. It helps you spot red flags. And yes, it helps you raise capital and communicate like a pro.

Here are three ways AI has become part of how I operate in real estate—plus the exact prompts I use to get value from it.

1. Due Diligence: Your New Second Brain

Underwriting isn’t just math. It’s information overload. You’re trying to make sense of PDFs, Excel files, broker emails, and market reports—all with different levels of clarity and spin.

That’s where AI tools like NotebookLM and Claude come in. I upload the OM, T12, rent roll, even past investor updates—and then I interrogate them.

Prompts I use:

• "What assumptions are made about rent growth in this OM? Are they supported by the comps?"
• "Summarize the CapEx plan in 5 bullet points. Highlight anything that looks deferred."
• "Compare 2023 expenses to 2022. Any categories that look inconsistent?"

This isn’t about saving 5 minutes. It’s about surfacing blind spots before they become mistakes.

2. Investor Communication: Draft First, Then Think

Writing investor updates and deal summaries used to take me hours. I always overthought it—how much detail? What tone? Will this spook someone?

Now I draft in 10 minutes using AI. But here’s the trick: I don’t just tell it to "write an update." I tell it how to think.

Prompts I use:

• "Turn these notes into an LP update. Keep it clear, confident, and avoid hype."
• "Rewrite this deal summary for a risk-averse investor. Focus on downside protection and track record."
• "Create 7 FAQs an investor might ask based on this deal memo. Include answers."

The first version is never final. But it’s 80% there. And that lets me spend time polishing, not starting from scratch.

3. Better Thinking, Not Just Faster Output

AI isn’t just a tool. It’s a thinking partner. When I’m evaluating a deal, I sometimes ask it to play devil’s advocate.

Prompts I use:

• "Assume this deal underperforms. What are the 3 likeliest causes and how would they impact LP returns?"
• "What’s missing from this OM that an experienced investor would want to know?"
• "Write a memo to myself explaining why I’m hesitant about this deal—based on the materials provided."

It challenges my assumptions. It surfaces risk. It forces me to slow down and ask better questions.

Choosing the Right AI Tool for the Job

Not every AI tool is built the same. Choosing the right one depends on what you're trying to do:

• For document analysis and cross-referencing: Use NotebookLM if you want to work with multiple files and ask detailed questions across them. It's best when you're juggling OMs, rent rolls, and historical data.
• For long-form writing and strategy support: Use Claude or ChatGPT-4. Claude handles longer context windows better (great for full deal packets), while ChatGPT is stronger for iterative brainstorming and refining your messaging.
• For CRM workflows and automation: Use tools like Clay or ActiveCampaign combined with GPT to auto-draft investor follow-ups or email sequences.
• For audio/video transcription: Use Whisper AI or Descript to quickly turn site visit recordings into searchable notes or highlight reels.

Start by mapping tools to pain points, not features. Ask: What task do I avoid or delay? Where do I wish I had a junior analyst or communications assistant?

Where to Begin Without Burning Out

Don’t aim for perfection on day one. Instead, focus on one high-friction task that already drains your time or energy.

For example:

• If investor communication slows you down, use ChatGPT to build your next LP update draft.
• If deal review feels heavy, drop the OM and rent roll into Claude or NotebookLM and ask it to surface key assumptions.
• If you're behind on follow-ups, use GPT inside your CRM to generate investor-specific email drafts.

The goal isn’t to master AI. It’s to let it clear the mental clutter so you can focus on real decisions. Start with the task you dread most and see what happens when you delegate the first 80% to AI.

Final Thought: The Edge Isn’t Access. It’s How You Use It.

Everyone has access to these tools. The differentiator isn’t whether you have AI—it’s how you think with it.

In the next post, I’ll walk through a full example of how I used AI to vet a deal, build a deal room, and prep LP communication—step by step. We’ll also dive deeper into specific use cases with tools like Claude, NotebookLM, and ChatGPT.

If you found this post helpful, consider subscribing to the blog. More detailed examples, prompts, and AI workflows for real estate investors are coming soon.