Dive deep into business, brand and strategy.
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The Figma Trap: Why Canva’s IPO Language Is Costing Billions Before They Even File
Two hours ago, a venture capitalist posted about Canva on LinkedIn. She previously ran a $100M early-stage fund. Spent seven years as a senior analyst at a $400M long/short equity fund, modelling public companies. Did late-stage, pre-IPO investing. She knows how to value software businesses. Her first instinct was to…
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How Bumble Gets Back to $13 Billion
Today, we’ll dive into how a $13 billion company destroyed 97% of its value by abandoning the one thing that made it worth $13 billion. The highlight reel, first. Bumble had one job: be the dating app where women go first. That single rule — women message first, men wait…
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Your Customers Don’t Describe You the Way You Think
The first post was about the gap you’re defending. The second was about the gap you’re feeding. This one is about what the gap looks like when you finally see it. Your website says “end-to-end platform.” Your customers say, “It’s the only one that doesn’t break during quarter close.” Your…
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The Room Shifts When You Walk In With Proof
Post one: you know the brief is wrong.Post two: every fix makes it worse. So what breaks the cycle? Not motivation. Not courage. Not a better strategist or a bolder CCO. The system punishes all of those. One thing breaks it: proof that doesn’t come from you. Think about the…
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The Machine Beneath the CMO
Last week, I wrote about the gap CMOs are defending without knowing it. This week: what the gap is doing while you can’t see it. Let’s say your company believes it owns “innovation.” Board decks say innovation. The brand tracker confirms it. Leadership alignment is strong. Everyone agrees. There’s just…
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The Cycle Nobody Built, but Everyone Runs
Last week, I wrote about the brief you already know is wrong. The response told me something. Not the likes. The DMs. Agency people didn’t push back on a single claim. They added to it. They told me worse stories. They named names — not publicly, but privately, the way…
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The Brief You Already Know Is Wrong
You know. You know the brief is curated. You know the client’s positioning describes who they want to be, not how the market sees them. You know the competitive set they handed you is the one that makes them comfortable, not the one that keeps their customers up at night.…
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The Gap CMOs Are Defending
You have 4.3 years. That’s the average CMO tenure at a Fortune 500. At the top 100 advertisers, it’s 3.3. In SaaS, it’s 18 months. And most of you are first-timers. 71%, to be exact. Walking into the highest-stakes marketing seat with no precedent for navigating it. Here’s what happens…
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Monopoly Moves: Agency Edition
For the agency professional who already knows the brief isn’t the whole story — and is ready to stop pretending it is. You already know. You know the brief is curated. You know the client’s positioning describes who they want to be, not how the market sees them. You know…
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Monopoly Moves: In-House Brand Edition
You’re not going to like this. You think your company owns “innovation” in the market’s mind. Your customers think you’re “reliable but boring.” A competitor you barely track owns the word you’re spending millions to claim. You don’t know this. You won’t find out for six months. And by then,…
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The Gap You’re Signing Into
Every high-stakes decision follows the same ritual. Before an acquisition, the deal team opens a data room. Revenue. EBITDA. Churn. Customer concentration. Contracts. Financials get audited. Legal gets reviewed. The numbers get stress-tested. Before a vendor contract is signed, procurement runs the process. RFPs go out. Demos get scheduled. References…
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AN INCOMPLETE MANIFESTO FOR POSITIONING
WHY THIS EXISTS I built systems. Monopoly surfaces external reality — what the market actually believes about a company. It can be run on clients, competitors, acquisition targets, or yourself. It shows the gap between what companies claim and what customers perceive. The Clarity Kit does the inside work —…
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