• 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…

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  • Autopsy: Kyle Poyar’s Fyxer Growth Analysis

    Autopsy: Kyle Poyar’s Fyxer Growth Analysis

    Why This Analysis Exists Kyle Poyar is doing great work. His newsletter, Growth Unhinged, consistently delivers sharp insights on go-to-market strategy, pricing, and growth mechanics. His decision to go all-in on the newsletter is admirable. It takes conviction to bet on your own platform and point of view. This analysis isn’t a critique of Kyle.…

  • What Kal-El and Simba Know About Identity That Most Businesses Don’t

    What Kal-El and Simba Know About Identity That Most Businesses Don’t

    Both have power. Kal-El can fly, bend steel, and see through walls. Simba is a lion. Born to rule Pride Rock. But power means nothing when you don’t know who you are. Their stories tap into something universal: the human battle for identity. Psychologist Erik Erikson referred to this as “Identity vs. Role Confusion,” a…

  • The $500 Billion Position That Compaq Threw Away

    The $500 Billion Position That Compaq Threw Away

    On January 1997, Compaq Computer was about to claim the most valuable mental territory in technology history. Their marketing team, led by George Favaloro and technologist Sean O’Sullivan, had identified a position that would eventually define a $500+ billion market. They’d written a press release about investing in NetCentric, and they were ready to claim…

  • Does “owning a noun” flatten positioning’s complexity?

    Does “owning a noun” flatten positioning’s complexity?

    Read this post first and then look at the comment section for Michiel. A Note on Michiel’s Challenge To Michiel, thank you for the thoughtful critique. Your questions about whether “owning a noun” flattens positioning’s complexity deserved more than a LinkedIn comment response. You’re absolutely right that positioning involves relationships, experiences, and narratives. Where we…

  • The Positioning Test That Destroys 99% of “Experts”

    The Positioning Test That Destroys 99% of “Experts”

    To every copywriter masquerading as a positioning expert, try this experiment. And if you’re hiring one, do this first. Here’s the test: Take these exact words: “We make AI work for you.” Now imagine three companies saying it: Feel the difference? When ChatGPT says it, you believe it. They own AI conversation in your mind.…

  • How Cluely Owns “Command” and Why Your Tactics Don’t Matter

    How Cluely Owns “Command” and Why Your Tactics Don’t Matter

    Why This Series Exists Most business advice is backwards. It starts with tactics (growth hacks, funnel optimization, messaging frameworks) and works backward to strategy. But tactics without position are just expensive experiments. You’re throwing spaghetti at the wall and calling the ones that stick “insights.” Here’s what actually works: Position → Identity → Distribution →…

  • Howie.ai’s Position: The AI Secretary That Owns Delegation

    Howie.ai’s Position: The AI Secretary That Owns Delegation

    TL;DR Howie doesn’t compete for “best scheduler.” It owns “secretary,” an entirely different mental territory. By reframing scheduling as delegation rather than self-service, Howie created a position where 1,000+ customers pay $25-95/month to CC an AI assistant that handles meetings with human-grade etiquette. The hybrid model (AI + human review) isn’t just about accuracy; it’s…

  • The most dangerous advice comes from those who succeeded without knowing why

    The most dangerous advice comes from those who succeeded without knowing why

    Everyone loves that Dakota Meyer quote about not taking criticism from people you wouldn’t take advice from. LinkedIn eats it up. Founders tattoo it on their minds. It’s also completely backwards. Here’s what I’ve learned analyzing hundreds of companies through the positioning lens: Successful founders are terrible at explaining their own success. Ask Stewart Butterfield…

  • Why 99% of Experts Would Get Chexy’s position Wrong

    Why 99% of Experts Would Get Chexy’s position Wrong

    Ask a LinkedIn “positioning expert” for Chexy’s position and they’ll give you articulation — who it’s for, how it’s different, what it replaces. That isn’t positioning. That’s framing. Let me show you the status quo (framing) versus the reality (positioning), and why Chexy is the counterexample that proves the rule. Quick primer if you don’t…

  • The Industry’s Biggest Confusion: Why Framing Isn’t Positioning

    The Industry’s Biggest Confusion: Why Framing Isn’t Positioning

    Most positioning work isn’t positioning at all. It’s framing. And this confusion is costing companies their shot at mental monopolies. Here’s a simple test. Pull up any company’s “positioning document.” If it starts with “We are…” or “Our product…” or answers “Who’s it for?” and “How’s it different?” That’s NOT positioning. That’s framing. This isn’t…

  • The 2.35% Reality of B2B Websites

    The 2.35% Reality of B2B Websites

    Over the last month, I wrote and covered that B2B websites influence just 2.35% of your total addressable market. And the response has been… intense. Comments and DMs range from marketers defending their budgets to CEOs questioning their spending. And surprisingly, a lot of agreement from people who’ve suspected this for years but couldn’t prove…

  • Why Everything You Know About Go-to-Market Strategy is Backwards

    Why Everything You Know About Go-to-Market Strategy is Backwards

    Note: Grant’s post about choosing between “rabbits” (many small customers) and “whales” (a few large enterprises) perfectly illustrates how even smart people can confuse tactical distribution choices with strategic positioning. He thinks he’s describing how to choose your go-to-market strategy, but he’s actually documenting symptoms while missing the disease (the causality flows opposite to what…

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