I watched a buyer overpay by a million dollars.
Not a projection. Not a rounding argument between reasonable people. A million dollars, gone, on a transaction that closed cleanly and left everyone at the table pleased with themselves. That buyer will go the rest of their life without knowing it happened. There is no line item for it on a closing statement. Nobody calls you a year later to explain what the number could have been.
What made it avoidable was not complicated. They chose representation based on proximity to the house rather than command of the market. The agent was capable, pleasant, and new. Did not know what to ask, and did not know the person on the other side well enough to ask it. So the questions never got asked and the answers never surfaced.
Why is it so hard to know if you hired the right real estate agent?
You hire someone you like. Someone who answers the phone quickly, shows up on time, seems sharp and organized and genuinely eager to help. Every one of those qualities is real, and not one of them is what determines your outcome. The qualities that decide it are almost entirely invisible at the moment you are deciding.
Which is the deeper problem. Real estate gives you exactly one data point. You sell the house once. There is no control group, no version where you hired someone else and got to compare. So the wrong choice almost never feels like a mistake. It just feels like the market.
Should you hire a friend to sell your house?
Somebody you know got their license. Your wife’s friend from the club. Your husband’s college roommate. A neighbor, somebody’s brother, a cousin. They are good people, they work hard, and you would like to send them the business.
I understand it completely. I also watch it cost people a great deal of money. You are not choosing a dinner companion. You are handing someone the largest asset you own and sending them to negotiate against a professional whose entire job is to move value from your side of the table to theirs. This is a business decision. It has to be made like one.
There is one honest way to evaluate it, and that is track record. What have they closed, in this market, at this price point, across a full cycle rather than one hot year? Who takes their calls? If they clear that bar, hire them and never look back. If they do not, the loyalty is expensive.
And be careful about one more thing. Someone helped your neighbor find a house, they were terrific at it, so you call them to list yours. Reasonable instinct, different job. Representing a buyer rewards inventory knowledge, speed, and reading the other side’s motivation. Representing a seller is closer to advisory work: pricing judgment made months before you have proof, the willingness to tell an owner a number they do not want to hear, and defending value all the way through inspection and appraisal. Both require negotiating skill. Almost nothing else about them overlaps.
What does overpricing a property actually cost?
Most owners think the downside of aiming high is a little lost time. It is not. It is money, and usually far more of it than the amount they were reaching for.
When a property is priced above where the market lives, a sequence begins that almost always ends the same way.
The first three weeks are wasted. That window is when your most qualified and best informed buyers see the property for the first time. They have been watching this market. They know what things are worth. They look, they do the math, they move on. You do not get that audience back.
The property goes quiet. Showings thin out. The agent community stops mentioning it. It becomes the comparable that helps sell someone else's house.
The property becomes market worn. Buyers start asking what is wrong with it. Nothing is wrong with it. The price was wrong. By then those two things look identical from the outside.
A lowball offer arrives. The seller looks left. Looks right. Nobody else is at the table. No company. No competing interest.
The seller takes it. And the number is very often below what they would have gotten in week two at the right price.
I have watched that spiral run more times than I can count.
The carry: run the math before you reach
Here is the part almost nobody prices in.
Start with a $3,000,000 home on 30A carrying $1,500,000 at a rate in the mid twos, which describes a great many houses around here right now.
Roughly $16,500 a month to keep owning a house you have already decided to sell.
Now hold the assumptions steady and move up the ladder. Same structure every time. Half the value financed at 2.6 percent, taxes and insurance and upkeep scaling with the property, and the owner's equity valued at a conservative six percent.
Read that bottom row again. At fifteen million, a year of being stubborn about price lands within a rounding error of a million dollars. That is not a metaphor or a scare tactic. It is arithmetic, and you can run it yourself on your own house in about four minutes.
Notice what is doing the damage. It is not the mortgage. A rate in the mid twos is exactly what makes waiting feel free, which is why so many owners talk themselves into holding. The largest line is the equity sitting still, doing nothing, when it could reasonably be earning five to seven percent somewhere else.
“I don’t have to sell it” is the most expensive sentence in this business. Nearly everyone says it, and it is almost always true. Very few of our clients have to sell anything. The point is that once you have decided to be a seller, waiting stops being free
Seller is a verb.
Seller is not a status you hold. It is a set of activities you perform. You get the property into good condition. You find out what matters in this market right now, not what mattered in 2021. You consider a pre marketing inspection so you control the story instead of reacting to someone else’s inspector. You commit.
The other version sounds like this. Let’s just put it out there and see what happens. I’m not spending a dollar on it. Let’s start high, we can always come down.
I work with people in both columns, and I always have. Nobody arrives already sorted out. Most people start in the second one, because that is where you naturally are until someone walks you through what the first one actually buys you. That conversation is my job, not your homework. I can get a result either way, and I have, many times. What I cannot do is pretend both paths end in the same place.
What does a good agent do that an average one does not?
They pick up the phone.
I know how that sounds. Thirty years in and my great insight is a telephone. But I regularly work deals where the agent on the other side will only negotiate by text. Every offer, every counter, every issue that surfaces during inspection gets compressed into a message thread, and their client has no idea that is how the largest asset they own is being handled.
A conversation tells you what terms actually matter to the other side, which is frequently not price. Where the seller’s head is today rather than on listing day. What the real activity has been, not what the marketing says. Whether a timeline or a life event is quietly driving the whole thing. None of that ever appears in writing.
This is chess, not checkers. You cannot play chess through a text message.
And it matters in both directions. When competing offers show up, and on 30A they often show up late rather than early, the outcome turns on whether your agent understands what that seller values, knows how to shape terms instead of only raising price, and is trusted enough by the listing agent to hear something honest. That never fails loudly. The seller simply takes the other offer and you are told it was close. So the cost is not always money. Sometimes it is the house.
If you want to talk it through
I would rather have a conversation than send you a form.
If you are weighing whether to sell, wondering whether your price is right, or trying to understand what a property is truly worth before you go anywhere near a contract, call me. If you would rather that conversation stay confidential, it stays confidential. Nothing attached to it, and nothing that starts a process you did not ask to start.
That is the whole point of this piece. The call is where the value is.
It matters who you work with. You just usually cannot see why until long after it has stopped mattering.
This month marks thirty years doing this on 30A and the Emerald Coast. I have seen clients leave a hundred thousand dollars on the table. I have seen five hundred thousand. And I have seen the one I opened this piece with. They never find out, and there is no benefit in telling them after the fact. But I see it, and I carry it around.
Frequently asked questions
How much does overpricing a home actually cost the seller?
More than most owners expect, because carrying cost scales with value. On a $3,000,000 home with half the value financed at a low rate, total annual carry runs about $198,000 once you include taxes, insurance, utilities, maintenance, interest, and the time cost of trapped equity. At $5,000,000 it is roughly $330,000 a year. At $10,000,000, about $660,000. At $15,000,000, close to $990,000 a year, or nearly half a million dollars for six extra months on the market. None of that accounts for the reduced final sale price that usually follows a long stretch on market.
Should I hire a friend or family member as my real estate agent?
Only if they would win the job on merit alone. Buying or selling a home is a business decision, and the person representing you will be negotiating against a professional. Evaluate track record in your specific market and price point across a full cycle rather than personality or effort. If your friend clears that bar, hire them with confidence. If not, the loyalty is expensive.
Is a good buyer’s agent also a good listing agent?
Not automatically. The two roles share negotiating skill and very little else. Buyer representation rewards inventory knowledge, rapid valuation, and reading the other side’s motivation. Listing representation is closer to advisory work, requiring pricing judgment made months ahead of proof, the willingness to deliver unwelcome news, and the ability to defend value through inspection and appraisal. Hire for the specific job in front of you.
Can the wrong agent cost me the house, not just money?
Yes. When competing offers appear, and on 30A they often appear late rather than early, the outcome turns on understanding what the seller values, structuring terms accordingly, and having the listing agent’s trust. This never fails visibly. The seller simply accepts another offer, and the buyer is told it was close.
