AI Learnings

Notes, quick takes, and deeper dives on AI tools, workflows, and things I think are worth paying attention to.

Deep Dive Sep 1, 2026

Peak AI Frenzy

You AI everything. You automate all the things. Then you find the checkpoints, realize you overbuilt, and come back down to using less. The comedown is the healthy part.

AI Product Management Workflow Verifiable
Deep Dive Sep 1, 2026

The only AI advice I actually give people

Use Claude for every task for two weeks, and refuse to route around a single blocker. That's the whole method. The gains compound faster than you'd believe.

AI Claude Product Management Workflow Verifiable
Deep Dive Sep 1, 2026

Five things in my AI preferences that actually changed my output

Preferences are not a setup step you complete. They're a living system you tune. Start with the heckle rule, which took one line and changed everything.

AI Claude Workflow Productivity Verifiable
Deep Dive Aug 31, 2026

A task that reports success and writes nothing

Eight weeks of watching my own scheduled AI tasks fail. The one that hid the longest never crashed once.

AI Automation Claude Verifiable
Deep Dive Jul 23, 2026

The handoff doc is the real product

I rebuilt my Research / Plan / Implement skills around one idea: each phase's deliverable is a 200-line baton, not the pile of work behind it.

AI Claude Workflow Verifiable
Deep Dive Jun 15, 2026

Build Magic decks by vibes, not by meta

Commander got taken over by win-rate spreadsheets. I use AI to flip it: start with the feeling I want at the table, then let it find the cards.

AI MTG Creative
Deep Dive Jun 12, 2026

What chasing 49 AI certifications actually taught me

The badges aren't the point. Working through dozens of certs is just the fastest way I've found to pressure-test a tool instead of trusting the launch video.

AI Certifications Learning
Quick Take Jun 10, 2026

I finally won a stock trade. Then I handed the money to the index.

My conviction trades have a perfect record of losing money. One finally worked. The real win was what I did with the profit, and what I chose not to buy next.

Investing Personal Finance
Quick Take Mar 24, 2026

The folder system that made AI actually useful

Most people re-explain their entire job to AI every single conversation. The fix isn't better prompts. It's better folders.

AI Claude Workflow Productivity Verifiable
Deep Dive Mar 24, 2026

Coding is solved. Now what?

Boris Cherny (Head of Claude Code) hasn't written a line of code by hand since November. Jenny Wen says the design process is dead. The Lenny's Podcast episodes this month are hitting different.

AI Engineering Lenny's Podcast Future of Work
Deep Dive Mar 24, 2026

AI + education is the use case I'm most excited about

I was homeschooled for high school. Personalized AI classroom assistants would have been a game changer for me, and they're about to be a game changer for a lot of kids.

AI Education Personal
Quick Take Mar 23, 2026

Claude Cowork Mode is the real deal

Been using it to build this site and manage my project roadmap. It's like pair programming with someone who actually reads the docs.

Claude Anthropic Workflow Verifiable
Deep Dive Mar 22, 2026

Five tools. That's the whole stack.

I've tried dozens of AI tools. Five survived. Each one does something the others can't.

AI Tools Productivity Workflow Verifiable