• 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.

  • Building a Marketing Foundation from Scratch

    Building a Marketing Foundation from Scratch

    Kait’s First 90 Days Kait just started as the first marketing leader at a mid-sized SaaS company. The team has never focused on marketing metrics before, and there’s no structure to measure impact. Kait’s excited but knows the road ahead involves setting up processes, getting buy-in, and translating marketing’s value into business outcomes. Here’s Kait’s…

  • Want to Learn Positioning the Right Way, Start Here

    Want to Learn Positioning the Right Way, Start Here

    Ever feel like ‘marketing’ (yes, quotes for suspicion) advice these days is just one big game of telephone? Someone tweets an idea, others retweet it, and suddenly it’s “the next big thing.” But when you dig deeper, it’s often the same recycled frameworks—louder but not clearer. Positioning is no exception. It’s one of the most…

  • think like a ceo. act like a designer.

    think like a ceo. act like a designer.

    Imagine this: You’re standing in a boardroom, surrounded by executives in tailored suits, their calendars packed, their minds preoccupied with numbers, strategy, and growth. You’re here to advocate for design—not as decoration, but as a driver of meaningful change. You’ve prepared your slides, rehearsed your pitch, and chosen your words carefully. But as you speak,…

  • the irony of the tiktok ban

    the irony of the tiktok ban

    The push to ban TikTok in the United States may have been intended to protect national security interests, but it has also sparked an unexpected cultural twist: Americans are flocking to alternative Chinese apps. Rather than bowing to the “China is evil and will steal your data” narrative, TikTok users—many of them representing a considerable…

  • I was thinking about how we choose a partner

    I was thinking about how we choose a partner

    Imagine you’re on a dating app. Two profiles pop up (pick a camp): Tom: “I’m 6’2″, love hiking, and have a great sense of humour.” Emily: “I’m a yoga enthusiast, foodie, and passionate about sustainability.” If finding a match worked the way some people (won’t name them, but you’ll know) think it does, you’d compare…

  • Where Can EQ Bank Go From Here?

    Where Can EQ Bank Go From Here?

    Let’s talk about EQ Bank, not from a purely analytical angle, but from the bigger question of what this bank truly means to people and where it might go next. The Canadian banking landscape has long been dominated by a few massive players, leaving most customers with limited choices and outdated systems. Institutions like EQ…

  • Marketing Isn’t Broken—Your Silos Are

    Marketing Isn’t Broken—Your Silos Are

    I recently spoke with a marketing leader who said something that stuck with me: “Our marketing team feels like 10 separate departments speaking 10 different languages.” Their performance marketing team focused on CTRs and ROAS. Their product marketers are fixated on features. Meanwhile, their brand team pushed storytelling—but it wasn’t clear how these efforts connected.…

  • Crushing Your Startup’s Future in One Sentence: How Comparisons Become Ceilings

    Crushing Your Startup’s Future in One Sentence: How Comparisons Become Ceilings

    You know what’s fascinating? Watching brilliant founders make the same positioning mistake that’s been happening since… well, since the first entrepreneur tried to sell a wheel as “like legs, but rounder.” (Sorry, ancient wheel inventor. You could’ve owned “effortless movement” instead.) Here’s what usually happens in my conversations with founders: Them: “We’re crushing it! We…

  • CALENDLY: FROM SCHEDULING TO OWNING TIME (PT 2)

    CALENDLY: FROM SCHEDULING TO OWNING TIME (PT 2)

    In Part 1, we explored how Calendly’s decision to compete head-to-head with other scheduling platforms risked trapping the company in a commoditized feature war. We introduced Peloton’s $40 billion meltdown as a cautionary tale of what happens when an innovative brand reduces itself to “just a product” instead of owning a bigger (deeper and resonant)…

  • Why Customers Know You But Still Don’t Buy

    Why Customers Know You But Still Don’t Buy

    (Dale’s post got me thinking. I highly recommend reading it and also following him on LinkedIn.) Many companies fall into the “brand awareness” trap, assuming that getting their name in front of customers is the silver bullet for driving sales. It’s a compelling idea: if people know who you are, they’ll buy from you. However,…

  • MY BEEF WITH EXPERTS: WHY “LEARN-IT-ALL” BEATS “KNOW-IT-ALL”

    MY BEEF WITH EXPERTS: WHY “LEARN-IT-ALL” BEATS “KNOW-IT-ALL”

    “Are you really an expert in positioning?” The question came during a client meeting. Before I could answer, I remembered something fascinating about Microsoft’s transformation. When Satya Nadella took over as CEO, he did something counterintuitive. Instead of flaunting Microsoft’s expertise, he pushed for a complete mindset shift from “know-it-alls” to “learn-it-alls.” The result? Microsoft’s…

  • Positioning: The Art of Owning Human Emotion

    Positioning: The Art of Owning Human Emotion

    Positioning isn’t about your product, features, or even your brand. It’s about something far deeper—a singular, human emotion that connects your audience to what you represent. Think of the world’s most iconic brands: At its core, positioning is the space you own in someone’s mind—the idea that defines you, differentiates you, and makes you unforgettable.…

Get Your CEO Clarity Starter Kit