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Make My Mess My Message · Issue 9 · Friday 7 August 2026

Sticking with the self-image that made you successful is the mummification of your own business.

The best positioning of my life, I built by accident. And for years afterward, I could not have told you how.

Before Genesis, before any of it, two friends wanted to go skiing. Glenn Wastyn was one of them. They were students, they had no money, and they had one idea: if enough of us go together, we can afford it. They asked around, and fifty more students wanted in. One busload.

That was the whole company. A bus, some rented apartments, a stack of ski passes, gear hired in bulk.

I was not there that first year. The second year they came looking for me, because they needed someone who knew how to work, knew how to have fun, and could teach people to ski. That was the whole job description. I said yes.

We never sat down and wrote a positioning statement. We had one rule, and it was almost too simple to say out loud. The customer was us. We built the trip we would want to be on.

One small thing tells the whole story. While everyone was up on the slopes on arrival day, we carried their luggage into the apartments for them. After a ten-hour bus ride and an afternoon on the mountain, people came to the bar, picked up their key over a beer or two, and walked into an apartment where their bags were already waiting. They were ecstatic. We had produced nothing. We had simply served people the way we would have wanted to be served.

And we never let it sit still. Every year we added something. New events, new activities, a better evening programme, a service nobody had thought to ask for yet. The price held. The experience got better every single season. People came back because they knew next year would be cooler than the last. That is how a student bus trip became an iconic name with a cult following, and a formula nobody could copy, though plenty tried.

One busload became more than ten thousand paying customers. And I want to be honest about the part that matters. We did not engineer it as a strategy. We stumbled into the best position a company can hold, then kept it alive by instinct, and the understanding of why it worked arrived years later, long after the doing.

That is the strange thing about positioning. You can get it perfectly right and have no idea how. Which means you can also lose it perfectly slowly, and never feel the moment it goes.

Call it Positioning Debt. It is the fourth of the four debts, and the quietest. The others announce themselves eventually. This one feels like loyalty the entire time you are running it up.

Here is how it works. Something you do makes you successful. A way of describing yourself, a kind of customer, a place in the market. Then the market moves. The company grows. What your partners need from you changes. But the story you tell about yourself stays exactly where it was, because it worked, and because changing it feels like betraying the thing that made you.

There is a word I keep coming back to for this. Mummification. Sticking with the self-image that made you successful is the mummification of your own business. Beautifully preserved. Perfectly intact. And no longer alive.

A ship in a bottle is a lovely thing. It is also a ship that will never sail again.

The best answer I know to this did not come from a book. It came from a man who did it himself.

In the 1980s, Intel was a memory-chip company. That was not just what Intel sold. It was what Intel was. Its identity. And memory was being crushed by Japanese competitors.

Andy Grove tells the story of sitting with Gordon Moore, the two of them running the company, watching it bleed. He asked Moore a question. If the board threw us out and brought in a new chief executive tomorrow, what would that person do? Moore did not hesitate. He would get us out of the memory business. And Grove said: then why don’t we walk out the door, come back in, and do it ourselves?

They did. Intel walked away from the thing that built it and became a microprocessor company. One of the great acts of a company refusing to be mummified.

I trust Grove on this more than I trust most people who write about it, for one reason. He did it. He did not theorise the pivot from a safe distance. He lived it, with the company on the line.

That is a distinction worth holding onto. Virtues, not values. A value is a word on a wall. A virtue is a thing you actually do when it costs you something. And the first virtue, the one all the others lean on, is courage. Without it, the rest are easy, or they are worth nothing at all. Re-positioning is not a clever idea. It is an act of nerve.

But there is a wrong way to do it, and it is the most common way of all.

Most companies that chase a new position pay for it by spending the trust that built them. They drop the channel that carried them. They go direct to the customer they used to serve through partners. They tell the people who staked their own name on theirs that the rules have changed now.

In a trust business, that is the most expensive mistake you can make. Because your real position was never the story you told about yourself. It was the story other people told about you when you were not in the room. You did not write that. You earned it, over years, with hundreds of small consistent acts.

Burn it, and it is gone. That is a one-way door. You do not win that trust back with a campaign. You win it back with years, if at all.

There is another one-way door in positioning, and it is quieter. Some choices redefine what you are the moment you make them. Put a shopping cart on your website, and the day the first person fills it and checks out, you are a webshop. One icon, one door, no way back. In B2C that is exactly right. In B2B, where your whole worth is being the partner who curates, advises, and makes the installer win, it can be deadly. The cart looks like a feature. It is a repositioning.

So both things are true at once, and holding them together is the whole skill. You must move your position as the world moves. And you must never burn the people who made you in order to become who you are next. Re-position, yes. Betray, no. Carry the trust with you.

I learned this the slow way, which seems to be the only way I learn anything.

Skikot, I got right by accident, and spent years not understanding it. Much later, with the businesses we build now, the market shifted, and what our partners needed from us shifted with it. This time I could see it while it was happening.

So we moved. Quietly. Not with a loud announcement that we had reinvented ourselves, because that would have been a lie, and it would have told every partner who trusted the old us that the ground had moved under them. We evolved, alongside the market and alongside the people we build with, until the new position simply felt like who we had always been.

That is the difference between an evolution and a rupture. An evolution keeps faith with the people who got you here. A rupture spends them. From the outside, the market cannot always tell the two apart. The people who carry you always can.

I am a builder. Not a flipper. I build things meant to last, not things meant to be flipped. That is not a promise never to change. It is the opposite. The things built to last are exactly the ones that have to keep evolving, quietly and honestly, without ever burning the trust that holds them up.

That is Positioning Debt. The slow, comfortable drift of becoming the wrong version of yourself, dressed up as loyalty. The cure is not to stay the same. It is to move with courage, and to bring everyone who trusts you along.

So try this on Monday. Two questions.

One: the story you tell about your company, is it still the story your partners tell about you? If they have drifted apart, that gap is your positioning debt.

Two: name one thing you still do because it worked years ago, not because it works now. Change that one thing. That is where you start paying it down.

That is the last of the four. Management, Technology, Decision, Positioning. You run them up quietly, on the inside, for years, and it is tempting to believe they stay there.

They never do. Every one of them reaches the customer in the end, added up into a single thing they feel and cannot name. Next Friday, the fifth debt. The only one your customer actually sees.

w. 🌊

Make My Mess My Message is a book written in public, one Friday at a time. This issue first appeared on LinkedIn. Every issue lives here.

Make My Mess My Message · Issue 8 · Friday 31 July 2026

The whole skill is knowing which door you are standing in front of before you commit.

In 2007, less than three years into building Genesis hta, I was certain I had it all figured out. So I bet everything, every euro I had and some I did not, on the growth I was sure was coming. Three months later, the crisis hit.

It took three years to survive what three months had broken.

I have written about that survival before. What I have not written about is the decision that caused it, because it took me years to understand what I actually got wrong.

Call it Decision Debt. It is the third of the four debts, and the most expensive of them. And almost everyone misdiagnoses it, because they think it is a question of being fast or slow.

It is not. It is a question of the door.

Two kinds of door.

Jeff Bezos put words to something every founder feels. Some decisions are two-way doors. You walk through, and if it is wrong, you walk back. Reversible. Cheap to undo. Most decisions are these, far more of them than we admit.

And some decisions are one-way doors. You walk through, and it closes behind you. Irreversible. There are very few of these, but they are the ones that can end you.

The whole skill is knowing which door you are standing in front of before you commit. Fast through the two-way doors, nearly all of them. Slow and careful at the one-way doors, the rare few.

In 2007 I did the exact opposite. I stood at a one-way door, betting the company on a single move I could not take back, and I walked through it at the speed you should only ever use on a reversible one. I was sure. And certainty is exactly what makes a one-way door feel like a two-way one.

There is a kind of money that punishes this hardest. Clay Christensen called it good money and bad money. Good money is patient for growth and impatient for profit; it lets you learn while the stakes are small. Bad money is impatient for growth; it forces you to scale before the plan is proven. I had used the bad kind, and I had used all of it, on the one door I could not walk back through. I read Christensen years later and recognised my own story in the pages.

Then there is the other half, and it is quieter.

If deciding too fast on a one-way door nearly ended me once, deciding too slowly on the two-way doors is what bleeds a company every single day. This is the debt most founders and leaders are carrying right now without seeing it.

It looks like caution. It is actually cost. A reversible call sits on a desk for three weeks because waiting feels safer. A meeting produces consensus instead of a decision, and consensus, dressed as harmony, is often just a slow no that nobody has to own.

The trap wears a reasonable face: we want to be sure. So we wait, for more data, more agreement, more certainty, until the vote is unanimous. But on a reversible decision, certainty is a luxury you buy with time you do not have. And unanimity is not alignment. It is either luck, or it is the quiet ones staying quiet.

And the interest on this one is paid in people. Good people rarely leave over money. They leave over the sense that nothing moves, that every clear call takes forever, that being right gets you nowhere. The wrong people, meanwhile, are comfortable in the slowness. It hides them.

Here is a distinction worth keeping. A decision, its execution, and its outcome are three different moments, sometimes years apart. You can decide fast and still execute with patience. You do not have to do a thing the instant you choose it. Speed belongs to the deciding. Patience belongs to the doing.

The fix is a question, asked out loud.

Before any decision of weight, name the door. Say it out loud. Is this reversible, or not? Nine times in ten you will find a two-way door wearing a one-way disguise, and the honest answer is: decide today, and move.

Here is the part that frees you, if you let it. The fear of moving fast almost always comes from treating a two-way door as if it were a one-way one. Once you see that most decisions are reversible, speed stops looking reckless and becomes what it actually is: good management. Recklessness is not speed. Recklessness is speed at the wrong door, and that was my mistake in 2007. Not the pace. The door.

So for the reversible many, build the habit of moving. Give the decision a single owner, a person, not a committee. Give it a deadline, because a decision expands to fill whatever time you leave it. Decide with enough to be roughly right, somewhere between half and most of the information, never all of it. Then say why, out loud, and ask everyone to commit, including the ones who argued against it. You are not hunting for unanimity. You are looking for one clear call the whole crew will row behind, even those who would have chosen differently. The person who says “well, I never agreed” the moment it goes wrong is not disagreeing. They are keeping a foot on the dock while the rest of you sail.

And when you open it to the room, remember that everyone has an opinion, and not all opinions weigh the same. Listen hardest to two kinds of person. The one who argues from first principles, not from the last example they happened to see. And the one who keeps the long arc in view, the mission, while everyone else fights about today. They are rarely the loudest. They are usually the quiet ones, who ask a question before they speak in absolutes, who think first and talk second. Give their words more weight than the volume in the room would ever suggest.

For the rare one-way door, do the opposite of what I did in 2007. Slow down. Get more eyes on it. And keep someone close who will tell you you are wrong, in the moment, to your face. Certainty is the disease. A person who pushes back is the cure. Without one, you sail in the mist at full confidence, straight into the rock, and afterward you blame the shore, never the captain.

The aim is not to make fewer decisions. It is to become the champion of them. To make many, at the right speed for the right door, and to have the humility to admit and overturn the wrong ones fast, before the interest runs

I did not have that discipline in 2007. I had certainty, and certainty is the most expensive thing a founder can carry through a door that does not open twice.

That is the third debt. Not indecision, and not haste. The failure to match your speed to the door in front of you.

Next Friday: Positioning Debt. The slow, comfortable drift of becoming the wrong version of yourself.

w. 🌊

Make My Mess My Message is a book written in public, one Friday at a time. This issue first appeared on LinkedIn. Every issue lives here.

Make My Mess My Message · Issue 7 · Friday 24 July 2026

Five simple tools, bundled, do not make a simple company.

The Four Debts, part 2 of 4.

What I never told the team, when I handed them a plane already in the air, was that the wiring was a mess of my own making.

I wrote last Friday about the letter where I gave them the stick. This is the part I left out.

Every company runs on software the way a plane runs on wiring and electronics. You never see it from the cabin. You only meet it when something stops responding.

This is the debt founders feel least, and it is dangerous for exactly that reason. Mine started with an assumption that felt obviously right. Buy the best tool for every job, a suite of best-in-class software, a quiver of perfect sails, and you will have the best way to run the business.

On the day you go live, you do. It works, and everyone is happy.

Then you sail some miles. Time passes, and the connections between all those perfect parts begin to fray. The cracks show. That is the first half of the mistake, a wrong assumption made at the very start.

The second half was more expensive. I kept the setup far too long, because I counted everything we had already sunk into it and underweighted what it was quietly costing us to stay. Sunk cost is loud. Opportunity cost is silent. For years I listened to the wrong one.

And I made it worse. I left the wiring in the hands of people for whom the complexity made perfect sense. Not for us. For them. A system that needs permanent maintenance is a permanent invoice. The Frankenstein kept growing, and I kept signing for it. My mistake.

Call it Technology Debt. It is the second of the four debts, and most people get it wrong before they start, because they assume it means old technology.

It rarely does. Ours was not old. Ours was excellent.

That is the trap.

Every tool we bought was genuinely good. The accounting package was good. The system we ran the business on was good. The file store, the chat tool, the video tool, each was best in its category and each solved the exact problem it was bought to solve.

Then you add them together, and something happens that no business case predicts.

Five simple tools, bundled, do not make a simple company. They make a permanently complex one. Each arrives with its own release cycle, its own opinion about how a process should run, its own way of naming the same customer. The complexity does not sit inside any of them. It sits in the seams between them, where nobody owns it and nobody is measured on it.

For a stretch of our growth, two of our systems told two different stories about the same month.

The accounting package counted invoices. It did not carry stock movement. The system we actually ran the business on carried stock, but only what had physically arrived, and it saw customer prepayments the accounting package did not.

Both were telling the truth. Neither was telling the whole truth. And the gap between them was not a rounding error. It was a different picture of the same weeks.

If you sail, you know the moment when a boat is working hard and you cannot yet tell whether it is about to lift and plane, or whether it is just pushing water and throwing a big wake. Same noise. Same effort. Completely different outcome.

That was us for longer than I would like. Plenty of speed, plenty of spray, and no quick way to answer the only question that matters: are we actually on course, or twenty degrees off?

We fixed it. I will come back to how. But be clear about what the cost actually was, because nothing ever crashed. The cost was decision latency. Every question worth asking had to be reconciled before it could be answered, and by the time you have finished reconciling, the moment you were deciding about has moved on without you.

Then there is the half you do not control.

We learned to treat upgrades properly. Test before you touch anything, because you are rewiring an aircraft that is already flying with people on board. So we planned, we tested, we scheduled the work for the quiet weeks.

At least half the time, it made no difference.

One of the tools in our carefully chosen suite would announce a fundamental change of its own. A new data model. A rebuilt way of connecting to everything else. Live on a date we did not choose. And because that one tool touched all the others, everything else had to move with it.

The clearest case was our accounting package rewriting how it handled data and how other systems talked to it. It was wired into everything we did. That single upgrade landed like a shot of entropy straight into the veins of the company.

Here is the line I would put on the wall. When you run your company on a stack of separate tools, you do not own your own upgrade calendar. You have rented it out to every vendor in that stack, and none of them coordinate with each other, or with you. The bill never arrives as an invoice. It arrives as a weekend.

You can feel this one before you can prove it.

Look for the human patch. Somewhere there is a person quietly re-keying the same data from one system into another, or rebuilding the same report by hand every week. That person is not inefficient. That person is the integration layer you never bought.

Ask who owns the source of truth. If three people give you three answers, you already have this debt.

Count how many of your last upgrades you actually chose. If it is fewer than half, your timing belongs to somebody else.

And time how long it takes to answer a simple question about your own business. Not how long to find the number. How long to trust it.

The way out is not a better tool.

This is where most advice fails. The answer to technology debt is not a better tool. Adding a better tool to a stack of good tools is precisely how you got here.

The answer is to start from the experience you want to deliver and work backwards to the technology, instead of buying technology and then bending the experience to fit whatever it happens to do. Most software is a solution looking for a problem, and it is very good at finding one inside your company.

So we stopped buying pieces and stitching them together. We moved onto a single system, one flexible and modular enough to bend around the way we actually wanted to serve partners, and we made everything live inside it. Not something we built ourselves, and not the newest or the cleverest tool on the market. One backbone we could shape to our own process, instead of five excellent tools that were never designed to live together.

That is the move. Decide what the experience is. Name one source of truth. Stop admitting anything that cannot feed it.

A warning from the far side, though. Once entropy is in, you do not fully undo it. You can rebuild, and we did, but you cannot put the universe back into a box. Every tool is easier to let in than to remove, which is why the discipline belongs at the front door, not in the cleanup.

Simplicity does not stand a chance against complexity when software is allowed in the fight. Unless somebody in the building is deliberately fighting for simplicity.

At first that somebody has to be you. Then, if you are wise, you stop leaving it to whoever happens to have time, and you build a team who owns your data and your systems, and you make simplicity the thing they are measured on. We did that years ago. They are still winning that fight, quietly, every week. That, in the end, was the real fix. Not a newer tool. A team who guards the front door and never stops.

That is the second debt. Not old technology. Too many good things, never designed to live together, quietly deciding your timing for you.

Next Friday: Decision and Speed Debt. The most expensive of the four, and the one I paid for in 2007.

w. 🌊

Make My Mess My Message is a book written in public, one Friday at a time. This issue first appeared on LinkedIn. Every issue lives here.