• 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.

  • Stuck is not loyal

    Stuck is not loyal

    Why banks mistake learned helplessness for loyalty, and what changes when leaving gets easier. Ask a bank why its customers stay and you will hear words like trust, relationship and loyalty. Ask the customers, and you may hear something else. “My paycheque goes there.”“Our mortgage is with them.”“We opened the…

  • The purchase does not prove you are the “only” option

    The purchase does not prove you are the “only” option

    “Be different. Own your category. Become the only choice.” This advice carries a familiar promise: find what makes your business unique, make that difference clear, and customers will choose you. The appeal is easy to see. Building a business is hard. Competition creates doubt. Being the “only” seems to offer…

  • Protecting the change you make possible for people

    Protecting the change you make possible for people

    Imagine a project manager who starts every morning chasing updates. They open five tools, message six people and still cannot tell whether Friday’s deadline is in trouble. Then they find a product that helps them see what needs attention and decide what to do. They spend less time checking and…

  • Just look like you have your shit together

    Just look like you have your shit together

    The problem with positioning and personal brand advice is that it keeps confusing the appearance of credibility with the conditions that produce it. My beef with almost all of positioning and personal brand advice online is simple: underneath the frameworks, scripts, hooks, and templates, the instruction is often the same.…

  • When the company becomes more important than the customer

    When the company becomes more important than the customer

    I don’t find “we’re customer-centric” very convincing. I want to know what happens when serving a customer gets in the way of hitting a target. That’s where I would look for the truth about a business. Imagine you run a support team. You want customers to spend less time on…

  • What Nike’s CEO Failed to Understand

    What Nike’s CEO Failed to Understand

    Positioning, capital allocation and the cost of getting the business wrong In March 2024, Nike’s chief financial officer described the mistake with unusual clarity. Matt Friend said the company had been “more focused on trying to achieve a mix of marketplace targets than we have on serving consumer demand where…

  • 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. Getting a finance product to the point where customers describe…

  • The One Room Where You Still Believe Words

    The One Room Where You Still Believe Words

    Most of us learn a simple rule before we can read: when words and actions clash, children often take their cue from what adults do. You can say “be gentle” in your calmest voice while you slam the cupboard, but the slam is the stronger lesson. You can tell them…

  • The Next Moat Is the Learning Loop

    The Next Moat Is the Learning Loop

    Why the winners in AI will own the path from trusted context to better decisions—not merely the data or the answer Enterprise technology is approaching an uncomfortable moment. Companies have spent years centralizing data, connecting systems, building dashboards, and creating increasingly sophisticated models of their businesses. Now they are adding…

  • Simile’s $2 billion raise: The CERN of Saying Things

    Simile’s $2 billion raise: The CERN of Saying Things

    TLDR: I read the study behind Simile, the AI startup that just raised $200 million to simulate human beings. The founders interviewed 1,000 people for 2 hours each and built AI agents that fill out surveys the way those people would. Their own paper grades the copies against survey answers…

  • “We left about a billion dollars off the table.”

    “We left about a billion dollars off the table.”

    Patrice Louvet runs Ralph Lauren. That sentence is his, from a 44-minute interview about the brand, and he delivers it the way other CEOs report a record quarter. A billion dollars of real revenue, real customers holding real money, and the company walked away on purpose. Every positioning conversation happens…

  • Everything I can prove about therapy

    Everything I can prove about therapy

    Therapy is a product. In the US alone, it sits inside a behavioural health market worth roughly $89 billion a year (Becker’s). It is sold by the hour, week after week, with no label on the box, no score at the end, and no receipt for whether it worked. I…

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