The Best Conversation Starter of the Year Is Happening Right Now

What To Say Now About March Madness

Every March, the same opening shows up. Most agents miss it.

It has nothing to do with real estate. It has everything to do with timing.

Right now, almost everyone in your database is living a version of the same experience. Someone in their life has gone fully into March Madness mode. Strong opinions about schools they've never visited. Scores checked during dinner. The word “bracketology” suddenly entering everyday conversation.

Even people who don’t follow college basketball are exposed to it this time of year. That shared cultural moment is an entry point.

The Topic Isn't the Value. The Relationship Is.

In real estate, most opportunities develop long before anyone decides they need an agent. They develop through familiarity. The agent who stays visible over time becomes the person people naturally think of when real estate eventually enters the conversation.

Small touchpoints like this help maintain that visibility.

A message connected to something happening right now feels natural to read and easy to respond to. It gives people a comfortable entry point back into the relationship without requiring them to be thinking about buying or selling today.

What to Say Now

Here’s something you can send this week:

Is this you?

Hi {{c.first_name}},

Most of us have someone in our lives going nuts right now, and it’s going to be ramping up through March.

Do you know what I’m talking about?

Yep. March Madness, and whether you're a rabid fan or can't tell a basketball from a baseball, someone in your life is about to change.

On other fronts, things are well here and I hope you're well too. Is there anything going on I can help you with?

Talk soon!

Why This Works

Messages like this aren’t really about basketball.

They’re about staying present in people’s lives in a natural way.

Most real estate opportunities don’t begin with someone actively searching for an agent. They begin with everyday conversations that keep relationships active over time. When people hear from you occasionally in ways that feel human and relevant to the moment, it becomes easier for them to reply, reconnect, and remember you.

That familiarity compounds.

When someone in their world eventually starts talking about a move, the agent who stayed visible is often the one who comes to mind first. Consistent communication is what keeps you in that position.

This philosophy sits at the center of what we build at Happy Grasshopper. Real estate is a relationship business, and relationships grow through simple conversations that happen over time.

Want More Help Like This?

Happy Grasshopper founder and CEO Dan Stewart hosts live sessions twice each week where he breaks down why messages like this are built the way they are and how to turn a simple reply into a real conversation.

If you want more content like this, timely, specific, and written to actually get a response, join him live.

Send these messages now