Calum Kershaw
Operations and data professional based in Nova Scotia, focused on improving systems, teams, and decision-making through practical analysis and thoughtful leadership fused with a growing skill in AI
| Platform |  | Pricing | Only free issues | Publishes | Weekly |
|---|---|---|---|---|---|
| Issues | 5 | Founded | 9 months ago | Last Issue | 6 months ago |
| Active | |||||
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calumkershaw.substack.comLatest Issues
The Skill That Makes AI Work
A lot has been written about prompt engineering as the key skill for working with AI. That framing is too narrow.
Last month I shipped a mortgage affordability tool for Nova Scotia. It covers 37 municipalities, runs CMHC insurance calculat...
I Built My Own AI Benchmark Because the Public Ones Don’t Matter
Today I watched Nate’s breakdown of the six reasons your work is hard — and which ones AI is actually automating.
The sharpest takeaway wasn’t about which model is smartest.
It was this:
The frontier is moving too fast for static benchma...
I Let My AI Work Grow Wild. Now I’m Learning to Wire It
I’ve been thinking about bonsai trees.
When they’re young, you mostly let them grow.
You water them. Rotate them toward light. Trim what’s obviously in the way.
But mostly, you let them explore their shape.
Then one day, they’re stro...
What Shipping AI Taught Me That Demos Never Did
Not because the models got worse — but because I shipped something real enough to break. Local demos gave way to serverless functions, environment variables, session state issues, and users who didn’t behave the way I expected. The magic di...
Building an Operational System (Not Just Using Better Tools)
This week I worked on multiple AI-related projects, learned new tools, and checked off plenty of tasks that were undeniably useful. But only a small subset of that work actually changed how I think about what I’m building long-term.
That c...
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Authors
The writers behind this newsletter.
Developing growable systems with AI — blending real-world management, experimentation, and learning. Fueled by coffee, D&D, and a curiosity about how things actually scale.
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