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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

The ERP Foundation Is the Whole Game. AI Changes How Fast You Can Win.

Gabriel PhilipsonJune 17, 20266 min read

Karl-Anthony Towns just won a championship with the Knicks. When asked what it actually takes, Towns did not talk about the games. He talked about the hours nobody sees....

Is AI Too Big to Fail?

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 ...