When I sit across from a CEO like you, the hardest part of our conversation is never the bad news. It is the good news that is lying to you. Most bosses think a positioning problem looks like a fire in the building — customers running for the exit, sales dropping to zero, and an empty bank account.

It almost never looks like that. By the time your total sales fall off a cliff, the fire has already been burning in your basement for two years.

Usually, when we first talk, your business looks fine from the street. You made twenty million dollars last year, and you are going to make twenty million dollars again this year. You tell your board, “The market is tough right now, so holding steady is a win.”

I have to look you in the eye and tell you something uncomfortable: in a living business, flat is not steady. If your company stops growing year over year, you are already shrinking. You just can’t feel it yet.

The Heavy Train Without an Engine

Picture a heavy freight train rolling down the tracks at sixty miles an hour. If the engine dies right now, what happens? The train doesn’t slam to a stop. Because it is so heavy, it keeps coasting down the tracks for miles.

If you sit in the front cab and only look out the window at the trees passing by, you will think the engine is still running fine. Looking out the window is a lagging sign — it only shows you the speed you built up two years ago from old customers who haven’t bothered to leave yet.

To know if your engine is dying today, you have to stop looking out the window and look down at the tiny warning lights on your dashboard. Those are your leading signs.

When we look closely at your dashboard together, we almost always find the same quiet lights blinking red:

• Your big pile of money looks fine, but your new money is drying up. Old customers are still paying their bills, which hides the problem. But the brand-new money you bring in each month is creeping closer and closer to zero.
• You only win deals at the cash register. Your sales team still hits their number, so nobody panics. But when we look closer, they had to chop 25% off the price on the last day of the month just to get the buyer to sign. People aren’t buying because you are special anymore. They are buying because you made yourself cheap.
• Your builders are filling a junk drawer. Every month, a loud customer waves a check and asks for a random new button. Because you are scared to miss the quarter, you build it. Slowly, your product stops being great at one main thing and becomes average at fifty things.
• Your sales calls feel heavy. Two years ago, buyers asked you about your big ideas. Today, they get on the phone and ask how they can cut five user seats to save a few dollars.

When those lights start blinking, why can’t you see what is really wrong? Because you are sitting inside the bottle. And nobody can read the label from the inside. That isn’t a flaw in you; it is just how bottles work.

Because you can’t read your own label, you tell yourself a comforting story. You think, Our business is fine. People just don’t understand everything we do anymore. We just need to tell our story better.

So you hire a copywriter or a branding agency to change the words on your website.

I get why you do it. Changing words feels safe. Nobody gets fired, no customers get mad, and you don’t have to change how you make money. Three months later, you put fresh red paint on the sour apples hanging from your tree. Everybody claps in Slack.

And six months later, the train slows down even more.

Why Words Come Last, Not First

Over the years, I noticed that almost every leader builds positioning backwards.

There are four levels to positioning, and you cannot skip the order:

• Level 4 is the Word you own in the buyer’s head. Think of Volvo owning Safety. You can’t just brag and claim this word; you have to earn it over years until buyers say it for you.
• Level 1 is how you say it. These are the words on your website and in your sales pitch. It is the easiest part to change and the weakest shield you have.
• Level 2 is how you prove it. This is the hard proof—numbers and real results that a buyer can check for themselves without taking your word for it.
• Level 3 is how you live it. This is where you put 70% of your money, your best people, and your daily focus—and what you flatly refuse to build, even when someone offers you cash for it.

The real order runs Level 4 → Level 1 → Level 2 → Level 3. You figure out the one concept you want to own, say it clearly, prove it with real results, and then wire your whole company around it so deeply that even a new boss couldn’t undo it.

Most CEOs live entirely at Level 1 while pretending they are at Level 4. They want a writer to hand them a magic sentence so they can skip the pain of Levels 2 and 3.

The Man Who Burned $110 Million on Purpose

Look at what happened at Intercom. Now called Fin.

When their founder, Eoghan McCabe, came back as boss in late 2022, Intercom looked huge from the outside. They had thousands of customers and hundreds of millions of dollars coming in.

But when Eoghan looked at the dashboard inside the cab, he saw the engine was dying. Brand-new money coming in had dropped to almost zero. The company was coasting on old weight.

If Eoghan had hired a copywriter to write sharper headlines for their old chat tool, Intercom would be a museum piece today. Instead, he started making decisions with his wallet that made normal business people sweat:

1. He gave away $50 million first. Customers hated Intercom’s confusing old bills. So he simplified the pricing and wiped out roughly $50 million in yearly revenue overnight just to earn back trust.
2. He starved the old business to feed the new one. He moved nearly 80% of his builders onto a brand-new AI worker named Fin—back when Fin was bringing in tiny crumbs of money. Most money managers would have stopped him at the door.
3. He killed another $60 million of his own safe money. For fifteen years, Intercom got paid for every human worker who sat in a chair using their software. Eoghan threw that away and said, “Now you only pay us 99 cents when Fin actually solves your customer’s problem.” He even put a $1 million bet on the table that Fin would fix at least 65% of problems. Moving customers to that new deal killed roughly $60 million of safe, old seat money. He killed it on purpose so his team couldn’t hide in the past.
4. He said no to easy cash. When his team built their own smart AI brain called Apex that beat the big tech giants, he refused to rent it out to other companies. And when competitors started sending armies of consultants to set up software for big buyers, he refused to copy them.
5. He threw away his own name. After fifteen years of building the Intercom name, he retired it calls-and-all, renaming the whole company Fin—right before Salesforce agreed to buy them for $3.6 billion.

Try asking a freelance copywriter to do that in a Google Doc.

The Blind Spot Inside the Bottle

Now, here is the twist that should make you sit up in your chair. Even after making all those brave moves, Eoghan still couldn’t read the outside of his own bottle.

If you listen to Eoghan tell the story, it is a war story about what he built. He says, “I built the Customer Agent. I invented the pricing. I built the fastest machine.”

In his whole story, he mentions almost nothing about what happened to the human being who actually bought the thing.

When I read the notes from his real customers—in the quiet corners of the internet where nobody is being sold to—they don’t care about the words “Customer Agent.” They care about who they became after using Fin for a year.

Before Fin, a customer support boss spent all day acting like a tired firefighter—running around a room of stressed-out people, apologizing for slow replies, and putting out fires.

After a year with Fin clearing most of the line, that boss’s day goes quiet. They stop being a firefighter. First, they become a conductor who tunes the machine. And underneath that, they become something even more important: the judge.

When the machine handles the easy stuff, the only thing left for the human boss is pure judgment—deciding which hard cases need a human heart, when to overrule the machine, and how to guide the team.

Fin didn’t just sell them a fast bot. Fin turned a tired firefighter into a trusted judge. And because Eoghan’s team didn’t see that clearly, they accidentally stepped right on it.

On customer forums, people who love Fin’s brain are furious about one thing they call the “resolution tax.” When a support boss sees Fin getting an answer wrong and jumps in to help the customer before the customer clicks “Talk to a human,” Fin still counts it as a win for the bot and charges the boss 99 cents.

Why does a 99 cent charge make a happy customer so angry? It isn’t the penny less than a dollar. It is because Fin is charging the judge a fine for using their good judgment! When your pricing punishes the exact proud new person you helped your buyer become, it leaves a bruise.

The $5,000 Copycat Game

Let’s bring this back to your desk. Look at the big words on your website today. If your most annoying competitor paid a writer $5,000 to copy every word off your homepage and paste it onto theirs by Tuesday, could they do it?

Would they have to walk away from $60 million in safe money to say your words? Would they have to move 80% of their builders into a new room? Would they have to turn down a single check from a bad-fit customer?

If they can steal your words without changing where they spend a dollar, you are living at Level 1. You have glitter, not gravity.

Words are free. Buyers only trust what costs you something to do, like Volvo giving away the three-point seatbelt patent for free in 1959, or Costco losing easy money to keep the hot dog at $1.50 for forty years, or Intercom burning its own seat money to prove its machine actually works.

Two Questions Before You Hire a Writer

Before you spend another dollar rewriting your website to fix your slowing growth, close your laptop and ask yourself two questions:

First: Who does my customer become after a year with us? Don’t tell me about your tool, your features, or your AI. Tell me who your buyer is when they walk into work today, and who they turn into a year after they sign your paper. Are you turning a firefighter into a judge? If you only talk about your machine, you are still trapped inside the bottle.

Second: Where is my wallet calling me a liar? Look at the last six months of your bank statements and your product calendar. What profitable money did you say no to because it didn’t fit the word you want to own?

If you haven’t given up anything that hurts, a copywriter cannot help you. Stop painting the apples. Fix what you are feeding the roots.