AI

JANUARY 28, 2026

A Coxswain on Your Shoulder

How AI can provide the continuous feedback loop athletes take for granted but professionals rarely experience

JANUARY 26, 2026

The Model T Comes to Silicon Valley

Ford's assembly line consolidated power : 253 automakers became 44. AI does the opposite, enabling millions of developers to build like behemoths. Expect thousands of new businesses & an explosion in second-order jobs.

JANUARY 22, 2026

AI Managing AI

The most capable AI models now spend their cycles orchestrating other tools. Specialization creates startup opportunity : build the specialists the executives call first.

JANUARY 20, 2026

The Postmodern Data Stack is AI

Three strategic acquisitions in nine months signal the fusion of the modern data stack with AI. Snowflake, ClickHouse, & Datadog are racing to own AI observability.

JANUARY 16, 2026

Software That Debugs Itself While I Sleep

Rather than manually debugging AI failures, I built a Ralph Wiggum loop that pushes the model against its failures each night until it dreams a correct solution.

JANUARY 14, 2026

Dead Companies Walking

Scott Fearon shorted 200+ companies from Silicon Valley. His six failure modes, from learning only from the recent past to falling victim to mania, are amplified by the AI shift.

JANUARY 13, 2026

Eleven Steps to the Epiphany[^1]

When I asked Claude Cowork to read my tools folder, it learned how I work in eleven steps. That moment revealed something about where computing is headed.

JANUARY 10, 2026

Open APIs Are Over

Salesforce, Datadog & Epic are locking down APIs. AI accelerates development, enabling incumbents to compete with partners. Platform businesses minted billions, but that ground is shifting. Here's the offensive response.

JANUARY 9, 2026

Trajectory

The competitive edge has shifted from adopting software to mastering how it's used. Trajectory data, the path users take through tools, is becoming the new moat for AI products.

JANUARY 7, 2026

The Text Box Isn't Enough

Why the future of AI interfaces looks like the past of computing. A comparison of the command line era to today's prompt engineering challenges & the return of the GUI.