The Judgment Problem
AI Strategy

The Judgment Problem

AI keeps getting cheaper at execution but still can't decide which problems are worth solving. Why judgment is the scarce skill for leaders, whatever the AI timeline.

Jun 9, 2026 · 5 min read
Foto Friday: Fog in the Canyon
Photography

Foto Friday: Fog in the Canyon

A 2019 sunset from the North Rim of the Grand Canyon, and the atmospheric haze that gives the canyon its depth.

Jun 5, 2026 · 2 min read
The Confidence Problem
AI Strategy

The Confidence Problem

AI outputs confidence whether it's right or wrong. Research shows models use more certain language when hallucinating than when correct — which means the signal we naturally use to evaluate sources actively misleads us.

Jun 2, 2026 · 6 min read
Foto Friday: Grand Canyon Sunrise
Photography

Foto Friday: Grand Canyon Sunrise

My first photography workshop, my first trip to Grand Canyon, and a sunrise that taught me what seven years of craft looks like in reverse.

May 29, 2026 · 2 min read
The Craft Problem
AI Strategy

The Craft Problem

Vibe coding and genuine excellence pull in opposite directions. One eliminates the conditions required for craft. The other requires them.

May 26, 2026 · 5 min read
The Local AI Option
Newsletter

The Local AI Option

Local LLMs like Mistral Medium 3.5 have crossed the line from research project to real architectural option. Here's who should be looking at on-prem AI.

May 5, 2026 · 4 min read
Foto Friday – Grand Canyon Sunset
Newsletter

Foto Friday – Grand Canyon Sunset

Sunset over the Grand Canyon from my first photography workshop, 2019. Went out solo the night before the conference and the sky put on a show.

May 1, 2026 · 1 min read
Why AI Sales Agents Convert 3x Worse Than Websites
Newsletter

Why AI Sales Agents Convert 3x Worse Than Websites

Walmart's ChatGPT checkout converted at one-third the rate of its regular website. The failure was a mismatch between what the agent was optimized for and what customers need at the moment of purchase.

Apr 28, 2026 · 4 min read
Foto Friday – Arches National Park
Newsletter

Foto Friday – Arches National Park

Long exposure at Arches National Park as the park empties out at sunset — car light trails, stars coming in, and the canyon going quiet.

Apr 24, 2026 · 1 min read

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