• 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…

Dive deep into business, brand and strategy.

  • Why Successful Founders Give Terrible Advice (And You Keep Following It)

    Why Successful Founders Give Terrible Advice (And You Keep Following It)

    Successful founders are the worst people to take advice from. Not because they’re lying. Because they genuinely don’t know why they succeeded. And following their advice will kill your company at predictable rates. Watch how this plays out: A founder builds a billion-dollar company. They look back and see what they did: talked to users,…

  • Brand, Reputation, and Health Are Not Strategies

    Brand, Reputation, and Health Are Not Strategies

    They’re outcomes. And confusing the two is why most attempts to “build” them fail. This isn’t a semantic distinction. It’s a fundamental misunderstanding of causality that costs companies billions, undermines personal credibility, and leads people to buy gym memberships they’ll never use. The pattern is identical across all three domains: Health is what happens after…

  • Rate.com’s $100 Million Positioning Paradox: When Owning Speed Means Nothing If You Won’t Claim It

    Rate.com’s $100 Million Positioning Paradox: When Owning Speed Means Nothing If You Won’t Claim It

    A Note Before We Begin: I’ve been following Victor Ciardelli and Rate.com’s journey for some time now. The work you’ve done, building Rate Intelligence, pioneering digital mortgage solutions, and expanding access for Spanish-speaking communities, is impressive. Your social media content showcases a founder who is genuinely committed to innovation and doing right by customers. That…

  • Canva: How Owning VOICE Made Freemium the Only Ethical Choice

    Canva: How Owning VOICE Made Freemium the Only Ethical Choice

    A Note Before We Begin: I’ve been watching Canva’s journey for years now, following Melanie Perkins’ content, tracking the company’s decisions, marvelling at what you’ve built. 240 million people are using your platform. A $26 billion valuation. The Two-Step Plan, committing billions to doing good. This is extraordinary work, and I have genuine respect for…

  • “Just add a text prompt” is the new “Just add water.”

    “Just add a text prompt” is the new “Just add water.”

    Why creative professionals are rejecting AI tools that make their jobs easier The Story Everyone Knows (And Why It’s Wrong) In the 1950s, General Mills introduced Betty Crocker instant cake mixes with a revolutionary promise: just add water. Perfect cakes, zero effort. Housewives loved the convenience. Except they didn’t. Sales tanked. So General Mills hired…

  • Kalshi: When Perfect Framing Masks Missing Ownership

    Kalshi: When Perfect Framing Masks Missing Ownership

    A Note Before We Begin: I’ve been watching Kalshi’s journey closely. Following Tarek and Luana’s social media, studying their regulatory victories, and seeing how they’ve built something genuinely innovative. The work they’re doing, fighting for three years to secure CFTC approval, creating a new category, and democratizing access to markets, is impressive. Deeply impressive. This…

  • Bryan Johnson: The $60 Million Bet on Algorithmic Immortality

    Bryan Johnson: The $60 Million Bet on Algorithmic Immortality

    A Note Before We Begin: I’ve been watching Bryan Johnson and Blueprint for a while now. The work is remarkable. The commitment is undeniable. The transparency is rare in an industry full of promises and empty claims. I wrote this because I find the intersection of business strategy and personal identity fascinating. How do companies…

  • Why Companies Buy Software They Can’t Use

    Why Companies Buy Software They Can’t Use

    The $1.2 Billion Question Nobody’s Asking Microsoft says 70% of Fortune 500 companies bought Copilot. Salesforce announced $1.2 billion in AI revenue. By any measure, these companies are crushing it. But here’s what doesn’t make sense: Salesforce’s CEO admitted in October that “the speed of innovation is far exceeding the speed of customer adoption.” Translation:…

  • Bumble: When You Make Your Position Optional

    Bumble: When You Make Your Position Optional

    A Note Before We Begin: I wrote this because I admire what Whitney Wolfe Herd and Bumble have built. Watching their journey (the social content, the advocacy work, the mission) has been genuinely inspiring. There’s something rare about a company that tries to change not just how we date, but how we connect. This analysis…

  • What Brad Jacobs Is Actually Teaching (And Why You’re Missing It)

    What Brad Jacobs Is Actually Teaching (And Why You’re Missing It)

    Before We Begin: Four Questions WHY does this matter to you? You’ve listened to successful founders describe their practices. You’ve made notes. You meditate now, or you tried for a week. You read the psychology books they mention. You ask better questions in meetings. But something’s off. You’re doing what they say they do, but…

  • How GONG Owns Certainty While Selling Intelligence

    How GONG Owns Certainty While Selling Intelligence

    A Note Before We Begin: I’ve been watching what you’ve built at Gong for a while now. The thought leadership you and your team put out. The way customers talk about what you’ve done for them. The trajectory from that “quarter from hell” at SiSense to defining an entire category and capturing 75% market share.…

  • Why the best positions are never stated

    Why the best positions are never stated

    Explicitly Implicit, Implicitly Explicit. The Burj Khalifa doesn’t say “we own eminence.” You feel it when you stand next to it. You feel it on the skyline. You feel it when someone mentions they went there. The position is implicit. Eminence is experienced, not claimed. And that’s precisely why it works. The positioning paradox Here’s…

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