Category: SYNG
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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…
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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…
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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…
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How Language Formed — And Why Professional Vocabulary Collapsed
I went looking for something small and fell through the floor. The small thing was a question I couldn’t shake. How did we ever agree on what words mean? Not grammar, not spelling. The deeper thing underneath those. When I say “chair” and you picture a chair, some machinery is running that neither of us…
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The end of choosing a bank
You don’t choose an electricity provider the way your grandparents did. You don’t choose a phone company the way your parents did. Within a decade, you won’t choose a bank the way you do now. That sentence will make most people uncomfortable. Banks feel permanent. They feel structural. Your chequing account isn’t a subscription you…
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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,…
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“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…
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Why Most ‘Positioning Experts’ Don’t Actually Understand Positioning
Let’s break down what’s really happening here, because Sara and Fletch have fundamentally misunderstood positioning while claiming expertise in it. What Sara Thinks She’s Describing Sara believes she’s making a sophisticated critique of strategic narrative. She thinks she’s being practical and buyer-focused by saying companies need to explain “what you are” and “what your product…
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Founder mode
In his essay “Founder Mode,” Paul Graham argues that the conventional wisdom about scaling startups — by hiring professional managers and delegating authority — often does more harm than good. He suggests that founders must stay deeply involved in their companies’ operations, even if it means upending traditional org charts and management practices. While Graham…
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Aristotle vs. Plato: Brand or performance?
Marketing often feels like a battle between two ancient philosophies. On one side, there’s brand marketing, which mirrors Plato’s belief in perfect, unchanging ideals. Plato’s theory of Forms posits that there are abstract, perfect forms of every object or quality, and that the physical world is merely an imperfect reflection of these ideals. Similarly, brand…
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Dude, Where’s My Target Audience?
Performance marketingBrand marketingProduct marketingWord-of-mouth marketingDirect marketing And… the word salad list goes on. Feels like marketer gymnastics in my mind. I might be basic. Hang in there I might have a point. Read this LinkedIn post first. Customers don’t give two fucks about marketing categories or whether a message is “performance” or “brand” marketing. They’re…
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Why do marketing titles make me mad?
What does a “Performance Marketing Manager” actually do? If you’re scratching your head, you’re not alone. We live in a world of hyper-specialized titles. Performance Marketing. Brand Marketing. Content Marketing. The list goes on. These titles seem clear at first glance. But dig deeper, and you’ll find they often create more confusion than clarity. Let’s…