• Lovable: What the Fastest-Growing Software Company Actually Owns

    Lovable: What the Fastest-Growing Software Company Actually Owns

    A Note Before We Begin: I wrote this because I genuinely admire what Anton Osika and the Lovable team have built. I’ve been watching their journey, the social content, the product decisions, and the speed of execution. What they’ve accomplished in eighteen months is extraordinary by any measure. This analysis comes from a place of…

  • Wealthsimple: What Happens When You Own the Door But Want to Own the House

    Wealthsimple: What Happens When You Own the Door But Want to Own the House

    A Note Before We Begin: I need to be clear about something from the start: I’m a huge admirer of what Wealthsimple has built and the work Michael Katchen and his team have been doing. I’ve been following your journey for years, the product evolution, the marketing campaigns, the social content, the way you’ve challenged…

  • Justin Welsh: The Solopreneur Who Proves More Than He Claims

    Justin Welsh: The Solopreneur Who Proves More Than He Claims

    Note Before We Begin: This analysis exists because I’ve been watching Justin Welsh’s work for years and genuinely admire what he’s built. The consistency. The refusals. The quiet proof. It’s rare to see someone walk away from easy money because it doesn’t fit how they want to live. I wrote this because I love looking…

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  • Lovable: What the Fastest-Growing Software Company Actually Owns

    Lovable: What the Fastest-Growing Software Company Actually Owns

    A Note Before We Begin: I wrote this because I genuinely admire what Anton Osika and the Lovable team have built. I’ve been watching their journey, the social content, the product decisions, and the speed of execution. What they’ve accomplished in eighteen months is extraordinary by any measure. This analysis comes from a place of…

  • Zoom’s S-1: The Gap Between What You Prove and What You Claim

    Zoom’s S-1: The Gap Between What You Prove and What You Claim

    How Positioning Language Shapes Market Valuation — And What Zoom Left on the Table An S-1 isn’t just a legal document. It’s a positioning claim to capital markets. It’s where you tell investors what mental territory you own, and they decide what that ownership is worth. Your product tells one story. Your metrics tell another.…

  • How do I create a position?

    How do I create a position?

    The position you think you have isn’t the position you actually own Most companies have it backwards. They sit in conference rooms crafting positioning statements, testing taglines, building messaging frameworks. They hire agencies to help them “craft their positioning.” They run workshops to align on “brand positioning.” Then they wonder why nothing sticks. The problem isn’t…

  • Wake Up, Neo

    Wake Up, Neo

    The Tax You Didn’t Know You Were Paying Every Canadian bank, from the giants to the slickest fintech, has built its business on a single bet: you won’t leave. Not because you love them. Not because they’re giving you a great deal. But because leaving is annoying. Think about what switching banks actually involves. You’d…

  • Position Is Not an Opinion: The Neuroscience of What Actually Happens in Your Customer’s Brain

    Position Is Not an Opinion: The Neuroscience of What Actually Happens in Your Customer’s Brain

    Most positioning conversations happen in conference rooms. Executives debate. Consultants facilitate. Post-its accumulate. Everyone leaves with an opinion about what the company’s position should be. Here’s the problem: position isn’t an opinion. Position isn’t what you decide in a workshop. It isn’t what you write on a slide. It isn’t what your leadership team agrees…

  • Why “Just Do It” Actually Works: The Neuroscience of Positioning Done Right

    Why “Just Do It” Actually Works: The Neuroscience of Positioning Done Right

    Three words. Coined the night before a presentation. Inspired by a convicted murderer’s last words before a firing squad. “Just Do It” shouldn’t have worked. And yet, it’s become one of the most recognized phrases in commercial history. Nike’s market share jumped from 18% to 43% in the decade following its 1988 launch. The tagline…

  • Wealthsimple: What Happens When You Own the Door But Want to Own the House

    Wealthsimple: What Happens When You Own the Door But Want to Own the House

    A Note Before We Begin: I need to be clear about something from the start: I’m a huge admirer of what Wealthsimple has built and the work Michael Katchen and his team have been doing. I’ve been following your journey for years, the product evolution, the marketing campaigns, the social content, the way you’ve challenged…

  • Justin Welsh: The Solopreneur Who Proves More Than He Claims

    Justin Welsh: The Solopreneur Who Proves More Than He Claims

    Note Before We Begin: This analysis exists because I’ve been watching Justin Welsh’s work for years and genuinely admire what he’s built. The consistency. The refusals. The quiet proof. It’s rare to see someone walk away from easy money because it doesn’t fit how they want to live. I wrote this because I love looking…

  • The Recovery Paradox: What WHOOP Proves Without Saying

    The Recovery Paradox: What WHOOP Proves Without Saying

    Note Before We Begin: This analysis comes from a place of genuine admiration. I’ve been watching WHOOP for years. Will Ahmed’s podcast appearances, the company’s content, and the way they’ve built something that clearly matters to the athletes and performers who wear it. There’s a rare discipline in what they’ve created. Most companies would have…

  • Clay: The $3.1B Category Creator Building Creativity Through Costly Signals

    Clay: The $3.1B Category Creator Building Creativity Through Costly Signals

    A Note Before We Begin: I’m writing this because I genuinely admire what Clay is building. I’ve been watching Kareem, Varun, and the team for a while now. The content they put out. The way they think about GTM. The courage it takes to burn the boats on a horizontal product and go narrow. The…

  • Shopify: The Existential Platform That Doesn’t Know What It Owns

    Shopify: The Existential Platform That Doesn’t Know What It Owns

    A Note Before We Begin: I wrote this because I genuinely respect what Tobias Lütke, Harley Finkelstein, and the Shopify team have built. I’ve been following their work, watching their content, studying their decisions. What they’ve accomplished is remarkable. 4.8 million merchants, millions of jobs created, billions in economic impact. That kind of scale doesn’t…

  • The Will Guidara Playbook: How Identity-Driven Positioning Transformed a Last-Place Restaurant into #1

    The Will Guidara Playbook: How Identity-Driven Positioning Transformed a Last-Place Restaurant into #1

    Introduction: Reading the Label They Couldn’t Read Everyone knows the hot dog story. A family at Eleven Madison Park mentioned they’d leave New York without trying a classic street hot dog. Will Guidara overheard this, ran outside, bought $2 hot dogs, had chef Daniel Humm plate them on fine china, and served them as a…

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