Cool is a mindset, not something you can copy

Back in 2007, two people who actually knew something about the subject sat down to write about cool. 

Noah Kerner, a marketing maverick. Gene Pressman, the man who ran Barneys New York for more than twenty-seven years and brought Armani, Versace, Prada, and Manolo Blahnik to American shoppers. The book was Chasing Cool.

Nearly two decades later, it remains one of the useful business books I return to, as it refuses to give you the formula for cool.

Here is the line that opens the book: " Cool is not a state of mind, a celebrity fad, or an American obsession. Cool is a business.

That distinction matters more now than it did when the book was published. In boardrooms across America, the chase is the same as it ever was. Kerner and Pressman describe product managers staring at vodka bottles and candy bars, tissue boxes and hamburgers, asking the only question that seems to matter: how do we make this thing cool? How do we make this gadget the iPhone of our industry? How do we do what Ralph Lauren did? How do we get what Hermes gets?

These questions are wrong, and the book spends pages explaining why.

The frantic search for the secret formula isn't the answer. Pressman and Kerner call it looking for the killer app, and they note that the more people believe a shortcut to cool exists, the more frantically companies chase one. The result is predictable. They end up looking in someone else's kitchen, copying a recipe that seems to work for another company, and failing miserably for theirs

Here is what the authors found after interviewing more than 70 of the most respected innovators of their era, from Tom Ford to Russell Simmons to Ian Schrager: the brands that endure do not rely on a gimmick. Ralph Lauren and Hermes are not relevant because of a viral campaign or a dash of bling. They are relevant because the leaders behind them took substantial risks, committed to a mindset, accepted the real possibility of failure, and in doing so opened the door to real success.

That is the uncomfortable part. Cool cannot exist without first acknowledging and navigating risk. You cannot focus-group your way to it. You cannot benchmark it from a competitor. You cannot buy it with a media budget. It is the visible result of an organization willing to operate without a net or a playbook, moving point-to-point like Teddy Roosevelt in the woods.

Three things this means for leaders:

First, relevance beats heat. Kerner and Pressman draw a hard line between what is hot and what is relevant. Hot is a moment. Relevant is a position. Focusing on relevance encourages leaders to think beyond fleeting trends and aim for sustained influence, inspiring confidence in their strategic choices.

Second, authenticity is not a tagline; it is a constraint. Pressman, careful never to hand readers a recipe, still names the essential ingredients: authenticity, passion, spontaneity, and a willingness to take risks. Notice that none of these can be delegated to an agency. They are organizational properties. They describe how a company actually behaves, not what its marketing claims. The audience can tell the difference.

Third, the shortcut is the trap. Every time a leadership team asks how to replicate another brand's cool, they reveal that they have stopped doing the harder work of building their own. Consider In-N-Out. A company that refuses to advertise, rarely courts the press, and runs a deliberately small menu, and still posts per-store sales that rival McDonald's because it built something coherent and let that coherence do the selling.

The way leaders communicate should be a strategic approach, shaping how audiences understand decisions before, during, and after they are made, reinforcing the importance of authentic, coherent messaging

Chasing Cool is, underneath the fashion and the celebrity interviews, a book about exactly that. The brands that endure are the ones that communicated a coherent worldview through every risk they took, until the market understood them before they had to explain themselves. That is not luck. That strategy looks cool from the outside.

Stop chasing cool. Build something worth copying, and let your competitors do the chasing.

Enjoy the ride + Plan accordingly.

-Marc

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Marc A. Ross helps leaders understand the world and how to talk about it. Two decades at the intersection of commerce and government.

He is the Founder of Caracal Global and Brigadoon.

He works with leaders who cannot afford to be reactive in an environment defined by permanent disruption.

Operating in DET, WAS, EDI + LON.

marc@caracal.global | marc@brigadoon.live | +1 202 596 5270

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The song I have played for 40 years

This August, Peter Hook and the Light open a 21-date North American tour in Cleveland, playing New Order's Get Ready front to back, a record that turns 25 this year. A few weeks ago, New Order itself announced remastered and expanded editions of (The Best Of) and (The Rest Of). Two camps of the same Manchester lineage, one selling the deep cuts, one selling the hits, both betting on the same thing: that the songs people already love are the songs people will pay to hear again.

This hits home for me.

I have been listening to New Order's Age of Consent for more than 40 years. The song is from Power, Corruption & Lies, released in May 1983. Four decades on, I still cue it up. Sure, I am open to new music, and I secure recommendations from KCRW. But Age of Consent still gets heavy rotation.

Is something wrong with me?

No.

There is a name for what is happening, and it is one of the most useful ideas I know for thinking about how you run a business.

In Algorithms to Live By, Brian Christian and Tom Griffiths devote a chapter to a problem computer scientists call explore versus exploit.

Explore means gathering new information. Exploit means using what you already know to get the best result available. Every choice you make, which restaurant, which song, which market, which message, is a bet on one or the other. Choose the familiar, and you exploit. Choose the unknown, and you explore. The whole art is knowing which bet the moment calls for.

Right now, most leaders are all-in on exploration. Everyone wants the new platform, the new market, the new tool, the shiny object that is getting buzz this week. AI has poured gasoline on it. The volume of options has gone vertical, and the reflex is to chase whatever is novel before the window closes.

Here is the uncomfortable part. The novelty reflex is often the wrong bet.

It comes down to where you are in your company's life and your career. A startup is in its childhood. It should explore. It does not yet know what it sounds like, who its customer is, or which message lands, so it experiments until something clicks. That is the right bet for that stage.

A mature company is in its adulthood. It knows. It has a product that works, an audience that shows up, and a strategy that performs. For that company, endless exploration is not curiosity; it is avoidance. The discipline is to stop searching and exploit what works. Form the habit. Build the cadence. Show up the same way until your customers expect you, demand you, need you. That is how an advantage compounds, and you cannot compound something you abandon every quarter to chase the next thing.

Three things this means for leaders:

First, audit your presence honestly. If you are a known quantity with a working formula and you are still operating like a startup, hunting the next shiny object every month, you are exploring when you should be exploiting. You are leaving expertise on the table.

Second, separate the tactic from the message. The tactic will change, and it should. But the idea you are known for, the thing customers actually come to you for, does not need to chase the algorithm. Peter Hook is not rewriting Get Ready. He is playing it in full because it is good and because his audience wants it.

Third, do not confuse tired with underplayed. Most of the time, the message you think is stale is not stale at all. You are just bored with it. Your audience has heard it a fraction as often as you have. What feels old in the boardroom is often brand-new to the market.

The best leaders hold both at once. They keep a small budget for exploration, a few bets on the unknown, because never exploring is its own kind of failure. But they spend the bulk of their energy exploiting what they already know works, because that is where results actually come from. They know when to keep searching and when to keep playing.

The world has changed, and the temptation to start over has never been stronger. Most leaders treat every new platform, every new tool, every new market as proof they need to abandon what got them here. The leaders who win in this environment know the difference between a strategy that is exhausted and one that has more runway.

Enjoy the ride + plan accordingly.

-Marc

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I help leaders sound like the smartest person in the room on what’s coming next — and know how to talk about it. | Founder @ Caracal Global + Brigadoon. | DET + WAS + EDI + LON

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Thinking through Anthropic and export controls

On Friday, June 12, 2026, at 5:21 pm Eastern, a letter from US Commerce Secretary Howard Lutnick landed at Anthropic. It ordered the company not to give its two most advanced AI models, Fable 5 and Mythos 5, to any foreign national anywhere in the world without a license from the Commerce Department. It cited export-control statutes written for civilian technology with military intelligence uses. It threatened criminal and civil penalties. Because Anthropic had no way to verify every user's citizenship in real time, the only path to compliance was to shut both models down completely. Three days after launch, the most capable models the company had ever shipped went dark for everyone.

Think about this. A commercial software product, available to hundreds of millions of users, many of whom pay serious cash for advanced features, was reclassified as something closer to a bazooka over the weekend. No public rulemaking. No comment period. A letter on a Friday evening from a government whose former AI and crypto advisor, and current member of the President's Council of Advisors on Science and Technology, was spotted at the SpaceX IPO celebration in Times Square alongside a group of other close associates and longtime friends of Elon Musk.

This is the part most leaders get wrong about the moment we are in. They treat a development like this as someone else's problem, a tech-sector story, a Washington story, an Anthropic story. It is none of those things. It is a demonstration of how fast the line between "commercial product" and "controlled national-security asset" can now move, and in which direction. If you run anything that touches advanced computing, biotechnology, energy, advanced manufacturing, or critical infrastructure, the Anthropic letter is a live drill for your own company. It's a good time to be selling potato chips and not silicon chips.

Reading a moment like this like a pro is the discipline I call SIGNAL™, the framework I use with clients to make sense of a volatile operating environment: Sources, Inputs, Geography, Noise, Analysis, Loop. The hardest letter in that sequence right now is N, for Noise. Because two stories are being told about why this happened, and they do not match.

The official story is a security story. An administration official told Axios that Commerce acted after a third party claimed it had found a way to jailbreak Mythos, alarming the administration about a national security risk, and that the lockdown would remain in effect until, in the administration's telling, the government's security apparatus is hardened. Cybersecurity experts quoted by Reuters worry that Mythos, built to find flaws in code, could turbocharge attacks on bank systems.

The other story is a feud story. Reporting from several outlets notes the Trump administration's Defense Department had earlier labeled Anthropic a supply-chain risk after the company drew red lines around military use of its technology. Defense Secretary Pete Hegseth made the posture plain, posting on Saturday from @PeteHegseth: "Three months ago, @DeptofWar kicked @AnthropicAI out of our building—forever. Every passing day proves why that was the right move. 🇺🇸"

Read against that backdrop, an export-control letter arriving on a Friday night, three days after a flagship launch, citing a jailbreak the company says exposes nothing new, looks less like a clean security intervention and more like the next move in a fight that started months ago.

Here is the analytical point. You do not need to know which story is true to act. You need to recognize that when the official rationale and the likely rationale diverge this sharply, you are looking at engineered Noise, and the job is to plan for both readings at once. Treat the security rationale as real, because the statutory authority is real, and the next letter could be addressed to you. Treat the feud rationale as real, because it tells you the rules are now personal, relational, and reversible in ways no compliance manual will capture.

Three things this means for leaders right now:

First, your regulatory exposure is no longer just what is on the books. It is your standing with the people holding the pen. Anthropic, by several accounts, got here partly because it said no to the Pentagon on principle. That may prove to be the right call or a costly one, but the lesson is that the relationship was the risk surface. Know where you stand with your regulators before the letter arrives, not after.

Second, geography just reasserted itself. Within seventy-two hours, G7 leaders meeting at Évian-les-Bains were discussing a "trusted partners" scheme to carve out allied access to American models, with the EU separately seeking Mythos to study it. The buzz from France was that Anthropic was a bigger issue than the Strait of Hormuz. Makes sense. The reach of a US export order, the scramble of allies to route around it, and the question of which side of the line your operations sit on are all questions of place. If your business assumed a borderless market for advanced technology, that assumption expired on Friday.

Third, silence is a position, and usually the wrong one. The leaders who weather a reclassification like this are the ones who have already built the relationships, framed their own narrative, and earned the benefit of the doubt before the crisis. The ones who go quiet and lawyer up discover that by the time they have something to say, the story has already been written about them.

The world has changed. The way you need to explain it has not. Most leaders treat communications as a tactic for explaining decisions after they are made. The leaders who win in this environment treat communications as a strategy that shapes an audience's understanding before, during, and after a decision is made, not just as an explanation after the fact. When the people who can switch off your most valuable product over a weekend are also the people forming an impression of who you are, that impression is not a soft asset. It is the asset.

Most leaders find Caracal Global through a communications audit because they know something is off, but have not yet sorted out their focus, positioning, or voice. The leaders who want to become the definitive voice in their sector run an Issue Authority System, executed like a campaign. And underneath all of it runs intelligence, the daily discipline of reading the world accurately that makes any of it credible. That is the SIGNAL work. It is the proof, not the pitch.

Enjoy the ride + plan accordingly.

-Marc