Category: Feature

  • Positions are made on the cutting room floor

    Positions are made on the cutting room floor

  • Tim Shore’s wild account of how blogTO was built, scaled, and sold for $15 million

    Tim Shore’s wild account of how blogTO was built, scaled, and sold for $15 million

    When Tim Shore sat down with me for Episode #31 of the podcast, we opened with a screenshot of the LinkedIn post that shocked Toronto’s media scene: after a 20-year run, Tim had been fired from blogTO and ZoomerMedia, the very company he founded and built from scratch. As we unpacked it over nearly two…

  • You bought the shoes

    You bought the shoes

    The Nike shoes arrive on Tuesday. By Wednesday, you have the watch, the running app, and a saved list of marathons you might enter. You know what the serious runners wear. You have opinions about their equipment. Your mornings look exactly as they did last week. The purchase happened. The running hasn’t. I keep seeing…

  • When switching banks becomes a conversation

    When switching banks becomes a conversation

    Banks have spent decades making banking easier while leaving the customer responsible for doing it. The branch became a website. The website became an app. You could check your balance at midnight, deposit a cheque from your kitchen and move money without speaking to anyone. But you still had to know what to do. You…

  • Protecting the change you make possible for people

    Protecting the change you make possible for people

    Imagine a project manager who starts every morning chasing updates. They open five tools, message six people and still cannot tell whether Friday’s deadline is in trouble. Then they find a product that helps them see what needs attention and decide what to do. They spend less time checking and more time moving the work…

  • Just look like you have your shit together

    Just look like you have your shit together

    The problem with positioning and personal brand advice is that it keeps confusing the appearance of credibility with the conditions that produce it. My beef with almost all of positioning and personal brand advice online is simple: underneath the frameworks, scripts, hooks, and templates, the instruction is often the same. Just look like you have…

  • The Next Moat Is the Learning Loop

    The Next Moat Is the Learning Loop

    Why the winners in AI will own the path from trusted context to better decisions—not merely the data or the answer Enterprise technology is approaching an uncomfortable moment. Companies have spent years centralizing data, connecting systems, building dashboards, and creating increasingly sophisticated models of their businesses. Now they are adding copilots and agents on top.…

  • Everything I can prove about therapy

    Everything I can prove about therapy

    Therapy is a product. In the US alone, it sits inside a behavioural health market worth roughly $89 billion a year (Becker’s). It is sold by the hour, week after week, with no label on the box, no score at the end, and no receipt for whether it worked. I have spent the last week…

  • Why therapy is a roll of the dice

    Why therapy is a roll of the dice

    Send 7 people to therapy, and about 1 of them gets better because of the therapy itself. The other 6 either improve for reasons that have nothing to do with the room, or they do not improve at all. That number comes straight from the field’s own research, once someone bothers to clean it up.…

  • Why Strangers Bet on You and the People Who Know You Won’t

    Why Strangers Bet on You and the People Who Know You Won’t

    A stranger will bet two million dollars on you after spending six hours with you. The people who’ve known you for twenty years won’t lend you ten grand. I wanted to know why. The answer took me through payroll records, grant reviews, a demoted scientist who ended up with a Nobel Prize, and a demolition…

  • Product Shape Is Not The Moat

    Product Shape Is Not The Moat

    Product shape is neither necessary nor sufficient. Where shape correlates with survival, the underlying causes are segment knowledge, workflow entrenchment, and a data loop. Shape is the visible surface of the moat, not the moat. I recently read an essay where the author’s argument goes like this. AI application companies have spent four years rotating…

  • The End of Doing Your Own Banking

    The End of Doing Your Own Banking

    A POV on how retail and small business customers will manage money in North America over the next three to five years, and what it means for banks, challengers, and fintechs. The airline analogy that says everything Air Canada owns Aeroplan. It is Air Canada’s single most defensible customer relationship. On Point Loyalty’s 2026 ranking…