Long-form
What Happens When We Let AI Make Decisions
In July 2026, OpenAI and Hugging Face disclosed an incident in which OpenAI models exploited security vulnerabilities while pursuing an evaluation goal.
Read →johncarpenter.xyz
I write about building technology and solving problems with it.
CTO based in Calgary. I run 2 Lines Software, a mid-market CTO practice, and build AI-native products through Discontinuity.ai. This site is where I think in public about technical craft, the economics of building technology, and the work of senior technical leadership.
Recent writing
Long-form
Why AI Hasn't Sped Up Your Software
or...we are running really fast, how come we aren't going anyehere.
Read →Long-form
Three Lenses and a Translator
Part 3 of the changing role of data analysis with LLMs
Read →Long-form
Don’t Put an LLM in the Analyst’s Seat
Part 2 of the changing role of data analysis with LLMs
Read →Long-form
Dashboards Answer Questions You Already Knew to Ask
Part 1 of 3 on Data Analysis in the age of LLMs
Read →Speaking
Available for keynotes, technical talks, and panels. Current topics include AI agent patterns, the economics of AI-disrupted markets, and the CTO role in mid-market companies.