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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