CTO/4
Writing

Field notes.

A few of the pieces most relevant to the work are below. The full archive is on Medium.

Anthropic ripped vector search out of Claude Code.

AIArchitecture

It replaced years of my reflexes with grep. The case that agentic search is really reranking in disguise — and where embeddings, RAG, and vector databases still earn their place.

Read Your Coding Agent's grep Loop Is Just Reranking in Disguise on Medium

Refactor, or rewrite?

StrategyArchitecture

The most expensive call a tech leader makes with the least to go on. I've run it twice — once it built a thriving company, once it delivered and missed the business return. A spreadsheet model for the decision, where the value isn't the model's accuracy, it's the discipline of building it.

Read A White-Knuckle Decision: Refactor or Rewrite on LinkedIn · Spreadsheet model on GitHub

Not every company needs a full-time CTO.

Fractional CTOLeadership

Some need one for a season, some for a single hard problem, some just often enough to avoid expensive mistakes. When the fractional model fits — and when it doesn't.

Read How You Know You Need a Fractional CTO on Medium

Older pieces and drafts live in the Medium archive.