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Thinking Out Loud.

Writing on AI, enterprise technology, and what it means to build at the intersection of strategy and execution.

Recent posts

Gabriel PhilipsonMarch 27, 20267 min read

I pay $100 a month for Claude Max. For that I get what amounts to an extremely capable executive assistant, a coding partner, a research analyst, a copywriter, and a systems archit...

AI Writes What You're Excited About. That's Not Always What You Want to Say.

Gabriel PhilipsonMarch 24, 20265 min read

I built this site using AI heavily throughout. Strategy, positioning, copy, HTML prototypes, the full technical build. When it launched I was pleased with how it came together. The...

The Dangerous Advantage: Why AI Rewards the Generalist

Gabriel PhilipsonMarch 21, 20265 min read

Early in my career at Harry Winston, people kept pulling me into problems that weren't mine. Not because I was the deepest expert in any single area, but because I could pick up a ...