Found in 2 comments on Hacker News
You recommended "Primitive Technology" which I thought of as well while reading the article. It would be really neat if he did an episode on making a more complicated wheel and axle structure.

Also, I would highly recommend "The Cross Time Engineer" series as it's this same scenario but works through how he's able to apply his modern knowledge as leverage to work up from a boatman earning pennies to running the country.

1 - https://www.amazon.com/Cross-Time-Engineer-Adventures-Conrad...

There's a really interesting book series called "The Cross Time Engineer". It puts a modern day engineer back into the middle ages and follows his path to rebooting an industrial society from just the knowledge in his skull.

While it's surely not wholly accurate, everything related to the material science and technology level is at least plausible.

http://www.amazon.com/Cross-Time-Engineer-Adventures-Conrad-...

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