Category Archives: Positioning & Messaging

The Telephone Game: Your Position Is Only as Good as Your Least-Informed Advocate

Ten phone calls will tell you what your position actually is. A dead radio fad from 1976 will tell you why. Your positioning is not a document. It is the sentence one distracted person says to another over dinner, somewhere between the entree and the check, when a name is needed and yours comes up.…

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Closing the Book on our Mad Men Marketing Pieces over the last 12 Days

What all of Mad Men teaches marketers in 2026 – not just the guy with the cheekbones – stress-tested against zero-click search, generative engine optimization, and an audience that clicks 1.6 percent of the time. EVERYBODY STUDIES DRAPER. THAT IS THE FIRST MISTAKE. Twelve character studies sit behind this piece: Draper, Olson, Sterling, Pryce, Cooper,…

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The Man Who Bought the Future by the Minute: Harry Crane

Seven marketing lessons from Harry Crane, the least likable visionary in advertising history – and what he tells us about the AI lead who just started running your company. He Opened the Wrong Paycheck Every great career pivot has an origin story, and Harry Crane’s is petty. In the third episode of Mad Men’s second…

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Last Firm Standing: Positioning in a Category That Is Shrinking

Why the most defensible position in American business may be a market everybody else is quietly leaving. 1. Every Positioning Book Assumes the Room Is Filling Up Open any marketing text and the same assumption sits underneath the advice: your category is getting bigger, and your job is to grab more of it. Land grab.…

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Ask Your Own People First

The one-question audit that takes an afternoon, costs nothing, and predicts your market position better than the deck you paid an agency to build. Send one email to every person on payroll. No warning. No preamble. No agenda item, no calendar invite, no courtesy heads-up to the department heads. One question: In one sentence, what…

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The Freddy Rumsen Rules: Six Marketing Lessons from the Most Underrated Man at Sterling Cooper

Six Marketing Lessons from the Most Underrated Man at Sterling Cooper – and What They Reveal About Freelancing Then vs. Now Everybody quotes Don Draper. Nobody quotes Freddy Rumsen. That is a mistake, and if you sell creative work for a living, it is an expensive one. Freddy is the guy who gets carried out…

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The Cutler Doctrine

What Mad Men’s least likable partner understood about marketing money – and what unapologetic financial leadership looked like then versus what it looks like now The Man Nobody Rooted For Everybody who watches Mad Men picks a favorite. Nobody picks Jim Cutler. He arrives in season six from the rival shop, and Peggy files him…

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