• 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 Your Tribal Signals Need Something to Signal

    Why Your Tribal Signals Need Something to Signal

    You can’t build a tribe around nothing. Black Flag tattoos work because Black Flag owns rebellion. Fair trade coffee signals because Fair Trade owns ethics. Supreme drops create frenzy because Supreme owns authentic streetwear culture. The moment you try to create tribal belonging without semantic content (the real concept or meaning behind something) underneath, the signal fails. Everyone wants…

  • Perplexity: The Curiosity Machine That’s Actually a Trust Engine

    Perplexity: The Curiosity Machine That’s Actually a Trust Engine

    A Note Before We Begin: I wrote this because I genuinely admire what Aravind Srinivas and the Perplexity team are building. I’ve been following their work closely, reading interviews, watching social media content, and tracking their product evolution. The technical execution is remarkable. The team is world-class. The growth trajectory speaks for itself. But I’m…

  • 37signals: The Company That Owns Control (And Doesn’t Know It)

    37signals: The Company That Owns Control (And Doesn’t Know It)

    A Note Before We Begin: I’ve been following Jason Fried and David Heinemeier Hansson’s work for years. Their books changed how I think about business. Their writing is consistently sharp, honest, and useful. I watch Jason’s posts on X not because I’m looking for flaws, but because I’m fascinated by what makes certain businesses connect…

  • When 95% Self-Awareness Meets 53% Stock Decline: The Chip Wilson Identity Crisis (Autopsy)

    When 95% Self-Awareness Meets 53% Stock Decline: The Chip Wilson Identity Crisis (Autopsy)

    The Delusion Everyone Shares Tasha Eurich’s research team discovered something unsettling: 95% of people believe they’re self-aware. Only 10-15% actually are. This isn’t about people being stupid. It’s about the gap between what we think we know about ourselves and what’s actually true. Most of us walk around convinced we understand who we are, what…

  • How Wynter Owns Clearance (And Why They Don’t Know It)

    How Wynter Owns Clearance (And Why They Don’t Know It)

    A Note Before We Begin: I’ve been watching Peep Laja’s work for a while now. The rigour he brings to marketing, the anti-BS stance, and the way Wynter has grown are impressive. His LinkedIn content consistently challenges lazy thinking, and I respect that deeply. This piece isn’t a critique. It’s an attempt to read Wynter’s…

  • How Exit Five Accidentally Built the Institution B2B Marketing Never Had

    How Exit Five Accidentally Built the Institution B2B Marketing Never Had

    A note before we dive in: I’ve been following Dave Gerhardt’s work for a while now. His LinkedIn content is excellent, and what he’s built with Exit Five is impressive. This analysis stems from genuine curiosity about why certain businesses connect to identity in ways that transcend their stated purpose. I’ve done my best to…

  • Why is Tesla worth more than Toyota?

    Why is Tesla worth more than Toyota?

    Market sentiment is the story your numbers are forced to play in. It’s not just your revenue, profit margin, or operational efficiency. It’s the collective emotion investors attach to what you represent. That emotion becomes the lens through which every metric gets interpreted. Here’s the proof. The 30:1 Paradox As of October 2025, two companies…

  • Hampton: How Owning Kinship Built an $8M Business That Members Would Take Loans to Keep

    Hampton: How Owning Kinship Built an $8M Business That Members Would Take Loans to Keep

    A note before we begin: I’ve been following Sam Parr’s work for years and genuinely admire what he has built. His podcast conversations are among the most candid in the startup world. This piece stems from fascination, not criticism. I love exploring what drives businesses to connect with identity rather than solve problems. I’ve tried to…

  • Positioning a Pricing Tool: From Description to Ownership

    Positioning a Pricing Tool: From Description to Ownership

    Let’s say you built a pricing optimization tool for B2B SaaS companies. Here’s where everyone gets stuck: “We help SaaS companies optimize their pricing through AI-powered analysis and willingness-to-pay research.” Clear. Functional. Completely forgettable. You’re competing with a dozen other tools saying essentially the same thing. So you try to differentiate on features: “But we…

  • When Jesus Tried to Explain ‘Salvation’ to His Disciples

    When Jesus Tried to Explain ‘Salvation’ to His Disciples

    Jesus sat on the mount, exhausted. Not from the sermon. From the meeting afterward. “Master,” Peter said, pulling out a scroll. “We’ve been working on the messaging framework for your teachings. Want to see the value proposition?” Jesus closed his eyes. “Peter. We’ve talked about this.” “Right, right. I know. But look, we’ve got the…

  • LinkedIn’s Positioning Advice Is Creating the Problem It Claims to Solve

    LinkedIn’s Positioning Advice Is Creating the Problem It Claims to Solve

    Before diving in, I respect both Anthony and Viktar. They’re helping companies clarify their messaging, and that matters. However, a fundamental confusion is occurring that needs to be addressed. This isn’t about calling anyone out. It’s about clarifying what positioning actually means versus what most people think it means. Also, the Emperor’s image source. Let’s…

  • TD’s Investor Day Autopsy: Great Plumbing, Weak Architecture

    TD’s Investor Day Autopsy: Great Plumbing, Weak Architecture

    “I’m excited we’re getting back to winning.” — Raymund Chun With that declaration, TD’s leadership kicked off an Investor Day (September 29, 2025) designed to signal a reset and a return to form. It was a masterclass in financial communications. The team framed a necessary overhaul around three universally agreed-upon promises: simpler, faster, and more…

Get Your CEO Clarity Starter Kit