Dive deep into business, brand and strategy.

  • 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banking landscape has long been dominated by a few massive players, leaving most customers with limited choices and outdated systems.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 Bank…

  • 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.…

  • Why the Best CMOs Think Like CFOs

    Why the Best CMOs Think Like CFOs

    Here’s the truth: the best CMOs don’t just market—they think like CFOs. That might sound counterintuitive, but if you want a seat at the table, you need to stop leading with campaign metrics and start speaking the language of business outcomes. CEOs and boards care about revenue, profitability, and market share—not clicks or impressions. The…

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