Recent Articles
Why Ownership is Shared
The Right to Care, the Right to Contribute, and the Right to Decide.
When ownership starts to matter When you work at a startup with fewer than 20 employees, you're forced to wear many hats. The question, "Who owns...
Product Leadership & Predicting the Future
Frameworks for Betting on a Future You Can't See
Every product leader is secretly a futurist. Look at the actual job: Vision is defining a future that customers want to be a part of Strategy is...
Strategic Planning is Context Engineering, Part II
A Free Open-Source Template
My first essay made the case that strategic planning is evolving into context engineering. That the right output of annual, quarterly, and real-time...
Strategic Planning is Essentially Context Engineering
Annual, Quarterly, and Real-Time Planning in a World of Humans and Agents
For years, building a business was constrained by how fast teams could execute. So we built planning systems around that constraint. Annual plans in...
Recent Projects
Content Recommendations
Using Semantic Search to Identify Similar Content
This follow-up project to vector search asks a slightly different question: What happens if the input is not a query, but a piece of content itself? Instead of searching “for” something, we let a URL...
From Keywords to Meaning
A Practical Experiment with Vector Search
Search has trained us to think in keywords. You type a few words into a box. The system looks for pages that contain those words. The ones with the most overlap float to the top. This works...
LLMs vs Traditional NLP
A Practical Experiment in Contextual Understanding for Advertising
Contextual advertising sounds simple on paper. Show relevant ads next to relevant content. In practice, it has always been harder than it looks. Understanding what a piece of content is actually...