Dive deep into business, brand and strategy.
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The iPod Didn’t Succeed Because of “1000 Songs in Your Pocket” (Autopsy)
Most people believe the iPod won because of brilliant marketing, that iconic “1000 songs in your pocket” tagline. But here’s the problem: competitors had similar marketing. And better features. Double the storage. Lower prices. Longer battery life. Replaceable batteries. FM radio. Voice recording. They all failed. Creative offered 60GB for $400 versus iPod’s 30GB for…
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Notion’s Positioning Paradox: You Already Own What You Think You’re Building Toward
A Note Before We Begin: I wrote this analysis because I genuinely admire what Ivan Zhao and the Notion team have built. Watching their journey, from near-bankruptcy to 100 million users, and following their social media content reveals a level of philosophical commitment rare in software companies. That commitment fascinates me. This piece exists because…
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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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Brand, Reputation, and Health Are Not Strategies
They’re outcomes. And confusing the two is why most attempts to “build” them fail. This isn’t a semantic distinction. It’s a fundamental misunderstanding of causality that costs companies billions, undermines personal credibility, and leads people to buy gym memberships they’ll never use. The pattern is identical across all three domains: Health is what happens after…
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Rate.com’s $100 Million Positioning Paradox: When Owning Speed Means Nothing If You Won’t Claim It
A Note Before We Begin: I’ve been following Victor Ciardelli and Rate.com’s journey for some time now. The work you’ve done, building Rate Intelligence, pioneering digital mortgage solutions, and expanding access for Spanish-speaking communities, is impressive. Your social media content showcases a founder who is genuinely committed to innovation and doing right by customers. That…
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Canva: How Owning VOICE Made Freemium the Only Ethical Choice
A Note Before We Begin: I’ve been watching Canva’s journey for years now, following Melanie Perkins’ content, tracking the company’s decisions, marvelling at what you’ve built. 240 million people are using your platform. A $26 billion valuation. The Two-Step Plan, committing billions to doing good. This is extraordinary work, and I have genuine respect for…
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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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Kalshi: When Perfect Framing Masks Missing Ownership
A Note Before We Begin: I’ve been watching Kalshi’s journey closely. Following Tarek and Luana’s social media, studying their regulatory victories, and seeing how they’ve built something genuinely innovative. The work they’re doing, fighting for three years to secure CFTC approval, creating a new category, and democratizing access to markets, is impressive. Deeply impressive. This…
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Bryan Johnson: The $60 Million Bet on Algorithmic Immortality
A Note Before We Begin: I’ve been watching Bryan Johnson and Blueprint for a while now. The work is remarkable. The commitment is undeniable. The transparency is rare in an industry full of promises and empty claims. I wrote this because I find the intersection of business strategy and personal identity fascinating. How do companies…
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Why Companies Buy Software They Can’t Use
The $1.2 Billion Question Nobody’s Asking Microsoft says 70% of Fortune 500 companies bought Copilot. Salesforce announced $1.2 billion in AI revenue. By any measure, these companies are crushing it. But here’s what doesn’t make sense: Salesforce’s CEO admitted in October that “the speed of innovation is far exceeding the speed of customer adoption.” Translation:…
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Bumble: When You Make Your Position Optional
A Note Before We Begin: I wrote this because I admire what Whitney Wolfe Herd and Bumble have built. Watching their journey (the social content, the advocacy work, the mission) has been genuinely inspiring. There’s something rare about a company that tries to change not just how we date, but how we connect. This analysis…
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What Brad Jacobs Is Actually Teaching (And Why You’re Missing It)
Before We Begin: Four Questions WHY does this matter to you? You’ve listened to successful founders describe their practices. You’ve made notes. You meditate now, or you tried for a week. You read the psychology books they mention. You ask better questions in meetings. But something’s off. You’re doing what they say they do, but…
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