Cup of Wit

Enterprise AI, without the theatre

Judgment for the age of AI adoption.

Cup of Wit is an editorial briefing for leaders, architects, and operators who need AI to survive budgets, governance, politics, and real work.

Core themes

A map of the work

Editorial rails for the archive. These can become filtered landing pages as tagging and community features mature.

AI Strategy

How leaders decide where AI belongs, where it does not, and what has to change around it.

Operating Models

The messy middle between ambition and adoption: governance, incentives, funding, roles, and delivery.

Agents & Automation

Practical notes on when agentic workflows are useful, risky, overbuilt, or worth scaling.

Prompting & Context

Better outputs by designing the assignment, not by chasing magic phrases.

Subscribe

A weekly note for people responsible for making AI useful.

One essay a week for leaders who want sharper operating judgment, not a louder feed.

Subscribe on Substack