Too Cool for School

Lee Iacocca did not invent the Mustang. He noticed that astronauts were cool, that men on suburban streets would never be astronauts, and that a cheap car with a long bonnet and a short deck could help them feel like they were part of the space race. Existing engine. Existing chassis. Existing longing. He put them together and shifted a million units in under two years. Nothing in that car was new. The combination was. And his timing and his targeting were excellent.

In its time the Mustang was cool. Ford was not. Some Australians will argue otherwise, but what they have is tribal loyalty, which is a different animal entirely and mostly defined by not being Holden. Barracking for a badge is not cool. The recombination was cool and the company that made it was a company that made cars. That gap is the whole subject of this third thought.

This is why what Iacocca did is worth analysing rather than admiring. He demonstrates that you can pick cool deliberately — read it, aim at it, time it — and make serious money doing so. How to define cool is a bit more tricky, because almost everything written about what it takes to be cool gets it backwards.

Personally Cool

We talk as though cool lives in a person. Bowie was cool. Elvis was cool. The Fonz was cool. But run the test cases and the person account falls apart immediately.

Neil Diamond made Hot August Night. The same man, the same voice, made Tennessee Moon. One is unarguably cool and the other is a punchline. But it is not just getting older that causes someone to lose their coolness.

Elvis died in 1977, uncool, eight years into a nostalgia act in a jumpsuit. In 2002 his ex-wife, who controlled the estate, licensed a remix of a 1968 B-side and for about four months A Little Less Conversation was the coolest track in the world. Elvis had been dead for twenty-five years. He did not participate at all.

So cool is not in the person. It is not in the audience either — no crowd can decide to find something cool. It happens between them, or it doesn't. It is a harmony. Cool is created by recombining existing elements to meet a latent aesthetic appetite the herd already had and could not name. Cool emerges within the interaction between artist and audience. Andy Warhol did not make tomato soup tins cool. What was cool was the recombination — taking the most banal object in America and putting it on a gallery wall — plus his timing and his targeting. Cool has three parts, and all three must land.

Someone recombines. Existing elements, put together in a way that has not been done. Not invention — recombination. Iacocca's car, Priscilla's remix, a Strat played at an academic innovation conference. I did that last one in front of four hundred people and for a fleeting moment I felt cool, and someone captured the picture to prove it.

The unnamed appetite is already present. Not created by the offer. The herd wants something it cannot express, and the recombination expresses it. Creating cool is a reading problem rather than a forecasting problem. More on this later.

The herd validates after. You can't know what is cool before the fact. You can only have a guess about what's cool confirmed after it's expressed. The person trying to be cool cannot know at the time whether they are pioneering or merely wrong. The two states are indistinguishable from the inside. Ziggy's lightning bolt and Tin Machine were the same act by the same man, made with the same aesthetic instinct and the same commitment. One is a reference point and the other is remembered as the embarrassment he survived. He could not have told you which was which on the day he started either of them.

This makes cool genuinely non-rational (and risky), and I want to be careful about what that means. It does not mean irrational or false. The value is intangible and real. It can't be found by inspecting the object, because it is not a property of the object.

A jacket that costs eight hundred dollars and is worth eighty as cloth is both a con and not a con. Someone who knows will rate it, and the buyer gets the cool cred. They bought status by association, a real thing that money can buy.

But the buyer is not cool because of the jacket. Nobody is ever cool because of the jacket. They might be cool depending on what they style it with — because that is a recombination, and it is theirs, and it is being exhibited in a setting where it is still novel. That is available to a purchaser, and it works, briefly.

The buyer who buys it to feel cool is a mug. Aping someone who already has status is the one move that cannot work, because the whole mechanism runs on newness and repetition is the opposite of newness. Fashion victims are tragic for exactly this reason: maximum effort, maximum expenditure, aimed with precision at the thing that guarantees failure. As a teenager I got this wrong like most of my peers. I had the clothes, the haircut, the music and the language that copied cool. But I was not like the cool cats who were somehow doing their own thing while remaining totally relevant. You can't express your individuality by copying the herd.

Cool consumes itself

Here is the part that makes cool structurally different from every other good. Social proof and the death of cool are the same event.

The signal that confirms what is cool is the signal that kills it. The moment enough people recognise the recombination to validate it, it stops being a recombination and becomes a category. Simmel had this in 1904 and Schumpeter gave it an engine: the entrepreneurial return exists only until the imitators arrive, and then it is competed to zero. Cool is not eroded by success. It is consumed by it.

Which is why the only durable form is serial reinvention. Bowie killed Ziggy on stage at Hammersmith in 1973, at the height, and came back as Halloween Jack, then the Thin White Duke, then went to Berlin and abandoned personas altogether. Please Please Me is not Rubber Soul is not Sgt. Pepper is not The White Album, and they are less than six years apart end to end. Madonna abandoned a persona while it was still selling and then built three more. Only two of them sold real numbers. Even Queen did a disco album. And while Freddie Mercury proved gay could be cool, Hot Space did not blow up. Under Pressure is the best song on Hot Space, but in my opinion the coolest version is David Bowie and Gail Ann Dorsey. They covered it live in Dublin as part of A Reality Tour in 2003. Dorsey's performance somehow stands up against Freddie Mercury's original vocals and at the same time she makes the track her own. Cooler still: Bowie handed her the song. The headliner became the support act for three minutes, in front of an audience who had paid to see him. So cool.

Reinvention looks like restlessness and it is actually the only available strategy: you have to abandon a working aesthetic while it still works, because by the time it stops working you are Elvis in Vegas. Cool has no terminal state. It just evaporates.

I love the Dandy Warhols line Heroin Is So Passé, and I love the song. They were cool back in the day. Before that I was into Adam and the Ants and Devo. My wife was into The Cure, so on the evidence she was considerably cooler than I was. And all the cool those bands had is now mostly memories. I think every one of them is still doing live gigs, which might be a little sad.

Death does not preserve cool either — it just freezes whatever state you were in when you stopped. Bowie died making Blackstar. Elvis died doing the same show for the fourth time that week. Same exit, opposite verdicts.

And before anyone else calls me out on it: I front two covers bands. Which means I am trading on expired cool, in a room full of people who want to hear the thing they already know. No premium attached, and everybody in the room knows the deal. The only moments it becomes anything else are the ones where we make a song ours — a different arrangement, a different key, something the original did not do. That is a recombination, in a room where it is new, and it is the only part of the night that we own. Maybe in those parts we have the chance to be cool.

Like most people, I want to be cool more than I feel like I am. I have spent enough time on both sides of the transaction to know what the machinery looks like from underneath.

Two lies

None of the above requires anyone to lie. Early adopters are early, late buyers are late, the good has an expiry and both parties can read the date. The mechanism runs perfectly well with everybody telling the truth. But there is money in it. And people who would lie will lie, or at minimum exaggerate, because there is money to be made and the currency here is unusually easy to forge. Marketing tells two lies, and they are different animals.

The first is extending expired cool. Trading on a verdict already delivered, long after the recombination has become the category. This is Apple now. The products are decent. The advertising is not selling a phone, it is selling a feeling from 2007 that has not fully decayed. It is Elvis in the jumpsuit, and it is the cheaper of the two lies because most buyers half-know. They are paying a premium for lock-in and telling themselves a small story about it. A bad deal, not quite a con. Unless you still think that owning an iPhone makes you cool. Let's be honest, it never did.

I wrote about Fenderwits, and that is the same disease in an older body — a company clinging so hard to expired cool that its remaining strategy is litigation over a silhouette. When the recombination is seventy years behind you, the lawyers are what you have left.

The second is worse. It is the music video with the hip young ones prancing about, already accepted, already surrounded by people who get it. That is not an aesthetic claim. It is a factual claim — that validation has already happened — made to the only audience whose validation could make it true.

It counterfeits the mechanism. Social proof is the thing that validates cool, so manufacturing social proof is not advertising a product, it is forging the currency. And it works often enough to be worth the budget, which is why every category does it.

The funniest advertisement you will ever see, if you stop and think about it, is a bank or an insurance firm claiming to be cool. An institution whose entire function is the management of other people's risk, hiring a director to shoot young people laughing in a warehouse conversion. It is a category error performed at enormous expense, and it runs constantly.

Except — hang on. Crypto is cool, isn't it? Or is it a scam. Or is it a genuine emerging alternative store of value outside fiat and outside the tax net. I honestly do not know, and neither does anyone telling you confidently in either direction. That is exactly the position you are in before the review comes back. Time will tell, which is another way of saying the herd has not finished validating.

This is predatory and preaching behaviour at the same time. Hacking social proof does not create the value it charges for. It extracts by simulating the one signal the buyer cannot independently check, wraps the simulation in the language of belonging and meaning, and degrades the signal for everybody by using it. Not cool.

So what?

I care about this for an unromantic reason. Money is agency. Not comfort, not status — the capacity to say no, to move, to choose your own constraints. Anything that reliably converts insight into money expands the space you get to act in, and cool is one of the very few things that converts a taste for the unnamed into cash.

But the conversion is narrow and it is one-shot. Cool pays at a lag and stops paying at scale, because scaling is mainstreaming, which is the thing that kills it. Whoever monetises a recombination at volume is by definition arriving after the cool has gone. That is not a reason to avoid the trade. It is a reason to be honest that you are selling the residue. Which leaves the only question that matters if you are trying to work out what might blow up.

Not what will people want next — that is forecasting, and the record on forecasting is dismal. The real question is what does the herd already want that nobody has named. That is a reading problem, in the present tense, about a state that already exists. It is much more tractable, and a few people are demonstrably good at it.

The trap is that a connection always feels insightful to the person making up what they think is cool. Every crank has that feeling in full measure and it is the same feeling. The felt insight is necessary and nowhere near sufficient. It tells you a bridge was built. It tells you nothing about whether the bridge carries load. For that you need someone else to pay. Which is the same test as the herd validating in review, wearing a suit.

So: notice the appetite nobody has articulated. Recombine into it. Accept that some of it will land and some of it will look ridiculous — I have no idea what the ratio is, and I do not believe anyone does, because being wrong is what removes you from the record. All I will claim is that there is a spread. If there were no failures you would not be reading anything, you would be following.

Or take the other road. Get enough cash to seed the inauthentic social proof and make your version of cool self-reinforcing before anyone has actually agreed to it. That works. It is most of what the industry does. It is also the thing I have just spent two thousand words calling a forgery, and I am not going to pretend the ledger balances because the return is good. If you have to buy the verdict, you did not earn it, and everyone downstream of you is paying for a signal that no longer means anything.

The first road is riskier and it is the only one where the thing you get is real. And when it lands and the imitators arrive and you feel the warm bath of being agreed with — understand that you are reading your own expiry notice, and start work on the next one.

I should be honest about why this one got written. I am still trying to track cool for myself. I would love to get rich by having something cool blow up. I just have not worked out what that is so far, and this third thought was the attempt to understand the machinery well enough to recognise it when it turns up. Work in progress.