• Ramp: The Best Experience Is the One You Don’t See

    Ramp: The Best Experience Is the One You Don’t See

    Ramp, Eric Glyman, and the position they built by accident and never named A note before we begin: I have been watching Ramp for a while now, and I think highly of what Eric Glyman and his co-founders have built.…

  • Fin: The Man Who Hated Bots Now Sells the Most Personal One

    Fin: The Man Who Hated Bots Now Sells the Most Personal One

    I have been following what Intercom, now Fin, has been building for years. Eoghan McCabe’s willingness to destroy a functioning business to rebuild it around a conviction is rare, and it deserves to be taken seriously. This analysis exists because…

  • Up Didn’t Build a Bank. It Built a Generation of Savers

    Up Didn’t Build a Bank. It Built a Generation of Savers

    A note before you read this: Dom, Grant, Xavier: I have been watching what you have built with genuine admiration for the past few weeks. Up is one of the few products in Australian finance where you can trace a…

Dive deep into business, brand and strategy.

  • Easy to Find vs. Worth Choosing

    Easy to Find vs. Worth Choosing

    On the difference between getting considered and getting paid. Most of the people arguing about how brands grow are having two different conversations at once, and almost none of them know it. One camp says brands grow by being easy to find: easy to remember, easy to buy, present in…

  • Up Didn’t Build a Bank. It Built a Generation of Savers

    Up Didn’t Build a Bank. It Built a Generation of Savers

    A note before you read this: Dom, Grant, Xavier: I have been watching what you have built with genuine admiration for the past few weeks. Up is one of the few products in Australian finance where you can trace a coherent identity all the way from the code to the…

  • The Prancing Horse

    The Prancing Horse

    The Positioning Delusion — On the Difference Between One Position and Two Disciplines The question making the rounds this week is whether the Ferrari Luce is really a Ferrari. It is the wrong question, and the speed with which everyone reached for it is the symptom worth studying. The popular…

  • What the Subway Took From Joshua Bell

    What the Subway Took From Joshua Bell

    On positioning, costly signals, and why the cheapest part of the craft is the part the market believes least. I keep coming back to the Joshua Bell story, and the longer I sit with it, the more I think it teaches the opposite of what it gets used to teach.…

  • “It’s Just Semantics” Is the Most Expensive Sentence in Business

    “It’s Just Semantics” Is the Most Expensive Sentence in Business

    Your words are making your decisions for you. In 1889, an Ethiopian emperor and the Kingdom of Italy signed the same treaty in two languages. The two versions agreed on everything except one word. That one word decided whether his country would stay free. His name was Menelik II. The…

  • The Autopilot Corp 3: When the Whole Economy Forgets the Customer

    The Autopilot Corp 3: When the Whole Economy Forgets the Customer

    Part 3 in The Autopilot Corporation series. Part 1 here. Part 2 here. It’s brutally hard to start a company. Anyone who’s done it knows. You spend years looking for the thing — the product, the wedge, the customer who actually pays — and most of those years are quiet.…

  • The Noun Elon Musk Left Out of the SpaceX S1: A Positioning Read of the June 12 IPO

    The Noun Elon Musk Left Out of the SpaceX S1: A Positioning Read of the June 12 IPO

    A note before you read this: SpaceX has been operating for 24 years, and the part of the company most worth respecting is the part the financial press does not write about: the engineering culture, the cadence, the tolerance for failure as a method, and the willingness to ship at…

  • The Costume Industry, Part III: Musk Did Not Kill Tesla. The Original Position Did Its Job.

    The Costume Industry, Part III: Musk Did Not Kill Tesla. The Original Position Did Its Job.

    On the difference between the fame that follows proof and the fame that replaces it. The Harvard Business Review just published a piece arguing that Tesla’s brand is now hostage to its CEO, and that the fix is for the company to manage Musk’s perception more carefully. The piece is…

  • The Costume Industry, Part II: Why Positioning Work Almost Never Produces a Position

    The Costume Industry, Part II: Why Positioning Work Almost Never Produces a Position

    On the difference between vocabulary debt and decision debt. A week ago, I published an essay arguing that “personal brand,” “brand positioning,” “homepage positioning,” “product positioning,” and “brand marketing” are intellectually lazy terms that smuggle the wrong mental model into strategic work. The response was the most generous I have…

  • The Costume Industry: Why “Personal Brand” (and Every Term Like It) Is Vocabulary Debt

    The Costume Industry: Why “Personal Brand” (and Every Term Like It) Is Vocabulary Debt

    There’s a particular kind of word that quietly does damage. It sounds professional. It travels well in meetings. It shows up in bios, decks, agency proposals, and LinkedIn posts. Nobody questions it because everyone uses it. And that’s exactly the problem. “Personal brand” is one of those words. So is…

  • The Intelligence Layer They’re All Missing

    The Intelligence Layer They’re All Missing

    TL;DR. The $153 billion global research industry (surveys, management consulting, analyst firms, social listening, and now AI search) sources its evidence from people and companies who know they are being observed. I call that performed signal. Every source biased in the same direction, toward the audience the data was produced…

  • Cloudflare built the internet’s Immune Layer

    Cloudflare built the internet’s Immune Layer

    A note before you read this: I’ve been watching Cloudflare for a long time. What Matthew Prince, Michelle Zatlyn, and Lee Holloway built, and what the team continues to build, sits in a category of its own. Fifteen years of decisions that quietly hold up a meaningful portion of the…

Get Your CEO Clarity Starter Kit