Thoughts on GTM strategy, AI, leadership, and the trail.
Years ago I hand-graded hundreds of CFA Level 3 problem sets in a tiny NYC apartment. What I learned about teaching people the shape of a thing — not the content — turns out to be exactly what I keep relearning about AI, judgment, and feedback loops.
A friend argues AI made solo fast enough that a collaborator is mostly overhead now. He's right that the beginning got easy. He's wrong that the beginning is the work — the part that decides whether anything matters still lives below the waterline, and that part still takes other people.
Our best ideas arrive at the worst times — on a walk, in the shower, half-asleep at 2 AM — and most of them die before we act on them. Here's the hacky system I built with Slack, a webhook, and Claude Code to shorten the distance from having an idea to doing something with it.
In order to juice your productivity in a high latency environment, you must multitask and context switch. We know how damaging that is. But we're just at the beginning of understanding the longer-term cost — AI fog, ADHD wiring, and a graveyard of 80%-shipped side hustles.
Over a year of shipping AI-assisted content, I've identified 15 patterns across 4 categories — banned phrases, structural tells, voice violations, and content sins — that make content read as obviously AI-generated. Here's the full checklist.
I gave Jesus, Buddha, Muhammad, Confucius, Laozi, and Zoroaster each a corpus of 23,000 verified utterances and asked them to collaborate on a handbook for living. What they wrote was astoundingly beautiful, somewhat disappointing, and surprising as hell.
I have a personal repository with thousands of documents, 50+ skills, and over 800 knowledge graph edges. But it doesn't know what it knows. So I built a system to fix that.
Without a robust context graph for your LLMs or agents to build on, your results will be inconsistent at best. Here's the three-tier knowledge pyramid that changed everything.