• Spotify: The Playlists Nobody Wants to Leave

    Spotify: The Playlists Nobody Wants to Leave

    A note before we begin: I have been watching Spotify for years, and I have a lot of respect for what Daniel Ek, Martin Lorentzon, and the team have built. Getting a product to the point where hundreds of millions…

  • North of Brooklyn — Positioning a pie

    North of Brooklyn — Positioning a pie

    A note before you read: Josh and Alex, I have a lot of respect for what you have built at North of Brooklyn over fourteen years. I have been watching your work for a while, and I keep coming back…

  • 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.…

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  • Why What Your Company Sells Doesn’t Match What Customers Actually Buy

    Why What Your Company Sells Doesn’t Match What Customers Actually Buy

    The Disconnect Every company has a pricing page that lists what it sells. Features, capabilities, packages, service tiers. The descriptions are accurate. The pricing is clear. The product does what the product page says it does. And yet, when you ask customers what they bought, they describe something else entirely.…

  • Glossier: The Brand That Proved Everything and Said Nothing — Until It Started Talking

    Glossier: The Brand That Proved Everything and Said Nothing — Until It Started Talking

    From Clarity to Gravity: Glossier Emily Weiss spent four years building trust before she sold a single product. She woke at 4 a.m. to write a beauty blog while working at Vogue, funded with $700 of her own money. She collected 11 rejections from VCs before Kirsten Green said yes.…

  • Positionmaxxing

    Positionmaxxing

    The positioning industry has a positioning problem, and it’s costing you more than you think. A post on X recently stopped me cold. @Kpaxs wrote: “When you understand a system too well, you start optimizing for the system rather than for reality. You know what success looks like, so you pursue success-shaped…

  • Anthropic: How the Company That Claims Safety Already Owns Trust — and Doesn’t Know It Yet

    Anthropic: How the Company That Claims Safety Already Owns Trust — and Doesn’t Know It Yet

    From Clarity to Gravity: Anthropic A Note Before We Begin: I wrote this because I’m genuinely fascinated by what Anthropic is building. I’ve been watching the company closely — the decisions, the product, the way Dario and Daniela Amodei show up publicly, the social content, the research papers, the moments…

  • The BriefCase Paradox: The Industry’s Most Expensive Learning Disability

    The BriefCase Paradox: The Industry’s Most Expensive Learning Disability

    Every agency says they want to be a strategic partner. Then they show up and ask for the brief. That gap, between what firms say about themselves and what their behaviour proves, is the most expensive undiagnosed problem in professional services. It costs the industry $12.5 billion a year in…

  • Monopoly Moves: Consulting Edition

    Monopoly Moves: Consulting Edition

    The playbook for the consultant who sells objectivity and starts every engagement from someone else’s story about themselves. You already know what’s wrong. “I spent the weekend reading their website, their investor deck, three earnings calls, and a dozen Glassdoor reviews. I walked into the pitch with a point of…

  • The Figma Trap: Why Canva’s IPO Language Is Costing Billions Before They Even File

    The Figma Trap: Why Canva’s IPO Language Is Costing Billions Before They Even File

    Two hours ago, a venture capitalist posted about Canva on LinkedIn. She previously ran a $100M early-stage fund. Spent seven years as a senior analyst at a $400M long/short equity fund, modelling public companies. Did late-stage, pre-IPO investing. She knows how to value software businesses. Her first instinct was to…

  • How Bumble Gets Back to $13 Billion

    How Bumble Gets Back to $13 Billion

    Today, we’ll dive into how a $13 billion company destroyed 97% of its value by abandoning the one thing that made it worth $13 billion. The highlight reel, first. Bumble had one job: be the dating app where women go first. That single rule — women message first, men wait…

  • Your Customers Don’t Describe You the Way You Think

    Your Customers Don’t Describe You the Way You Think

    The first post was about the gap you’re defending. The second was about the gap you’re feeding. This one is about what the gap looks like when you finally see it. Your website says “end-to-end platform.” Your customers say, “It’s the only one that doesn’t break during quarter close.” Your…

  • The Room Shifts When You Walk In With Proof

    The Room Shifts When You Walk In With Proof

    Post one: you know the brief is wrong.Post two: every fix makes it worse. So what breaks the cycle? Not motivation. Not courage. Not a better strategist or a bolder CCO. The system punishes all of those. One thing breaks it: proof that doesn’t come from you. Think about the…

  • EQ Bank: How Every Decision Proved Ownership While the Marketing Said Challenger

    EQ Bank: How Every Decision Proved Ownership While the Marketing Said Challenger

    A note before you read this I have been watching what EQ Bank has built with genuine respect. Andrew Moor turned a personal irritation into a structural argument against extraction, and that is not a small thing. What the company has done, quietly and consistently, over more than a decade,…

  • PC Financial: The Bank That Was Never a Bank

    PC Financial: The Bank That Was Never a Bank

    A note before you read this I’m a positioning strategist, not a financial analyst, and I have no inside access to PC Financial’s data, internal strategy, or Barry Columb’s thinking. What I have is what’s publicly visible: the decisions the company has made over time, the content it puts into…

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