The Dark Side of Real Estate: The Part Nobody Posts About

Let me tell you a story.

This is not the kind of story you see on Instagram.

There are no photos of keys in hand.

No champagne pops.

No smiling families standing in front of their new front door.

There is no closing table at the end of this one.

There is just me, sitting with everything I invested in a transaction that never happened.

And I want to tell you about it because I think we need to be more honest about what this business actually looks like.

The Deal That Was Supposed to Close

I worked with a buyer client for months.

And when I say worked, I mean WORKED.

We looked at more than 25 homes over two solid days of showings.

Two days.

Driving across Sarasota.

Driving to Bradenton.

Driving back.

Walking through property after property.

Talking about neighborhoods.

Taxes.

HOAs.

Flood zones.

Schools.

Commute times.

Roof age.

AC age.

Renovation costs.

All of it.

And this was just the marathon showing session.

Before that came weeks of phone calls, text messages, emails, questions, research, listings sent, listings dismissed, and more questions.

After that came the offer.

And the negotiation.

I negotiated $31,000 off the asking price.

My buyers were thrilled.

We had a contract.

We had a path to closing.

We had a light at the end of the tunnel.

And then everything fell apart.

Enter ChatGPT

The other agent on the transaction was using ChatGPT to generate their communications.

I do not know this for a fact, but I know it the way every experienced agent knows it.

You read the emails and you can tell.

The language is generic.

The tone does not match any prior conversation you have had with that person.

The phrasing is overly formal in places and oddly casual in others.

There is no personality.

There is no context.

There is just a wall of words that sound like they were written by someone who has never actually spoken to you.

Because they were not written by a person.

They were generated.

And those communications created confusion.

They created misinterpretation.

They created friction where there should have been collaboration.

What should have been a straightforward negotiation between two professionals representing their clients turned into a game of telephone where one side was speaking in a language no human actually uses.

Small misunderstandings snowballed.

Deadlines got murky.

Expectations got misaligned.

The deal started to wobble.

And eventually, it tipped over.

The Deal Died

The transaction fell apart.

Not because the numbers did not work.

Not because the inspection revealed something catastrophic.

Not because financing fell through.

The deal died because of poor communication made worse by AI-generated correspondence that created confusion and eroded trust between the parties.

And when the deal died, my buyers walked away without a home.

The sellers walked away without a sale.

And I walked away without a commission.

Not because I did not do the work.

I did the work.

I showed over 25 homes.

I negotiated $31,000 off the asking price.

I managed every step of the process.

I was present.

I was professional.

I was responsive.

I did my job.

And I made zero dollars for it.

That is the dark side of real estate.

That is the part nobody posts about.

The AI in Real Estate Conversation Nobody Is Having

I am not anti-AI.

Let me be very clear about that.

I use AI in my business every single day.

I coach agents on how to use AI effectively.

I have written extensively about the power of AI tools for real estate agents.

AI is not the enemy.

But how you use it matters.

It matters enormously.

When you use AI to draft a communication and you send it without reading it, without editing it, without making sure it sounds like you, without checking that it actually addresses the specific situation at hand, you are not being efficient.

You are being careless.

And in a business where a miscommunication can kill a transaction involving hundreds of thousands of dollars, carelessness has consequences.

I do not know what instructions that agent gave to ChatGPT.

I do not know if they reviewed what it generated before hitting send.

I do not know if they even realized how much damage those emails were doing.

But I know the outcome.

A deal that should have closed did not close.

Buyers who were ready to buy walked away disappointed.

Sellers who wanted to sell had to start over.

And somewhere in the middle, a piece of technology wrote emails that helped undo months of human work.

That is the part of the AI conversation nobody is having at the conferences.

We talk about efficiency.

We talk about speed.

We talk about automation.

We do not talk about the deals that die because somebody decided a chatbot could handle their client communications better than they could.

Why Professionalism Matters When the Deal Dies

Here is what I want other agents to hear.

It is easy to be professional when the deal is going well.

It is easy to show up when there is a closing date on the calendar and a commission check at the end.

The real measure of professionalism is what you do when the deal dies.

I did not call that other agent and scream at them.

I wanted to.

I will be honest.

I was frustrated.

I was angry.

I had invested weeks of my life into that transaction.

I had spent money on gas, on time, on emotional energy.

And I had nothing to show for it.

But I still had to show up for my clients.

I still had to help them process what happened.

I still had to guide them toward whatever came next.

Because that is what professionals do.

We show up even when there is no commission at the end.

We handle the disappointment with grace even when we are disappointed too.

We take the hit and keep going.

That is the part they do not teach you in real estate school.

Relationships Matter More Than Transactions

Here is what I have learned after 30 years in this business.

Transactions come and go.

Some close.

Some do not.

Some pay you.

Some cost you.

But relationships endure.

Those buyers I mentioned?

They are still my clients.

They did not blame me when the deal fell apart.

They saw that I had done everything I could.

They saw that I was honest with them throughout the process.

They saw that I did not disappear when things got hard.

And when they are ready to try again, they will call me.

Because I earned their trust.

Not by closing a deal.

But by showing up even though the deal did not close.

That is what this business is really about.

It is not about the transactions you close.

It is about the people you serve.

And the people who remember how you treated them when everything went wrong.

What I Want You to Take From This

If you are a real estate agent, I want you to hear me on three things.

One. AI is a tool, not a replacement for your professional judgment.

Use it. Learn it. Leverage it. But never, ever send an AI-generated communication without reading it first and making sure it sounds like you. Your clients deserve your voice, not a machine's approximation of one.

Two. Deals will fall apart. It is part of the job.

You will work for months and get paid zero. It will happen. It happens to every agent who does this long enough. The question is not whether it will happen to you. It is whether you will let it break you or whether you will use it to build resilience.

Three. Your reputation is built in the hard moments.

Anyone can be a hero when the deal is easy. The agents who earn lifetime clients are the ones who handle the disasters with grace, honesty, and professionalism. That is what separates the people who survive this business from the people who thrive in it.

I share this story not because I want sympathy.

I share it because I think we need to be more honest about what this business actually looks like.

The Instagram version of real estate is keys and closings and champagne.

The real version is showing 25 homes over two days, negotiating $31,000 off the asking price, having a deal fall apart through no fault of your own, and waking up the next morning to do it all again.

That is the dark side.

And if you are going to survive in this business, you need to know about it.

Not so you can be afraid of it.

So you can be prepared for it.

Serving Southwest Florida — Sarasota, Manatee, and Charlotte Counties.