How a Chicago Realtor Uses AI to Run His Business

I've been a Chicago REALTOR® for 25 years, and I lead The Rosenberg Group @ Infiniti Properties. Some people also know my voice from radio. I hosted shows on WLS, WCPT 820 and Evanston's WCGO 1590 AM, and those shows were all about real estate.

I've also always loved tech. So when AI tools got genuinely useful, I started using them in my own business, and then I started building simple automations around them. Today I teach other people to do the same thing, in plain English.

Here's a look at how I use AI and automation day to day, and why I think almost any small business can borrow the same ideas.

Real estate is a small business with a lot of moving parts

From the outside, real estate looks like showings and closings. On the inside, it's a small business like any other: new inquiries come in at all hours, every client has dates and deadlines to keep track of, there are emails all day long and the marketing never stops.

If you own a small business in Chicagoland, that probably sounds familiar. Swap "showing" for "estimate" or "appointment," and the problems are the same. That's why the tools I use work just as well outside of real estate.

Lead follow-up

When someone reaches out, they want to hear back quickly. But I'm often with a client, in a car or at a closing when a new inquiry arrives.

This is where an automation like the Lead Responder comes in. A new inquiry arrives, the AI reads it, and a personal reply is drafted in my voice so I can review it and send it quickly. The details go where they belong, so nothing lives only in my inbox.

The goal isn't to replace the personal touch. People still want to talk to a person, and they should. The goal is to make sure nobody waits too long and nobody falls through the cracks.

Reminders

Real estate runs on dates: appointments, inspections, deadlines, closings and checking in with past clients. Keeping all of that in my head was never a good plan.

Now my calendar and a few simple automations do the remembering. Reminders show up when I need them, and the AI can draft the matching message, whether that's a friendly check-in or a note to confirm a time, so I'm not starting from a blank screen.

Emails

Email is where AI saves me the most effort on a normal day. I use it to:

• Draft replies and follow-ups that I then edit to sound like me.
• Rewrite a message so it's clearer, shorter or a little warmer.
• Summarize a long email thread into the few points that matter.
• Turn my notes after a meeting into a follow-up email and a to-do list.

That last one is the Meeting Assistant idea: the call ends, notes get summarized, action items get listed and a follow-up is ready to go while the conversation is still fresh.

Marketing

Marketing is never finished, and AI is a great creative partner. I use it to get a first draft of property write-ups, brainstorm social media posts, outline newsletters and create images with AI image tools. Posts can be drafted ahead of time and scheduled to go out on their own.

One rule I never skip: a human reviews everything before it goes out. AI can sound confident and still be wrong, and in a regulated business like real estate the details matter. The AI gives me a head start. The final word is mine.

What I've learned along the way

• Start with the task that annoys you most. That's where you'll feel the difference first.
• Keep a person in the loop for anything a client will see, at least until you trust the setup.
• Teach the AI your voice. A few examples of your real writing go a long way.
• Protect client information. Be thoughtful about what you paste into any tool.
• Tools change fast, habits last. Learn the basic patterns and you can move between ChatGPT, Copilot, Claude, Grok and whatever comes next.

What your business can borrow

You don't have to sell homes to use any of this. A contractor can use a Lead Responder for new estimate requests. An insurance or accounting office can use reminders and drafted emails around deadlines. Almost anyone can use a Monday Morning Brief, a short summary of the week ahead that lands in your inbox every Monday at 7 AM.

That's what I teach, in person around Chicagoland or online over Zoom or Google Meet. It can be a 1:1 session ($125/hr), the 3-Session Mastery Pack ($335) or a 2-hour team training for up to 10 people ($750). If you'd rather have it built for you, Done-For-You Automation Setup starts at $999, and the AI Retainer ($149/mo) keeps things running when apps update or an automation needs a tweak.