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Craig McCaskill

People, product and systems

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Technology and Future

A collection of 3 posts

May 29, 2025

How to Think About AI

New tools don’t just change what we can do, they change who wins. The printing press didn’t eliminate scribes overnight, but it made literate societies dramatically more powerful than illiterate ones.

Technology and Future Leadership and Culture

May 25, 2024

Playing Favorites - How AI Shapes Our Knowledge Without Us Noticing

AI is making us all smarter in exactly the same way, and that might be the problem. What happens when the most accessible knowledge becomes the most uniform? As AI increasingly curates what information we see, are we trading the...

Technology and Future Thinking and Learning

August 23, 2023

The Great Enshittification - How Product Evolution Becomes Product Regression

In 2012, Netflix was a meticulously organized catalog that helped you discover films and shows across genres, decades, and continents. In 2015, Spotify was a music lover’s sanctuary that put your personal library and thoughtful exploration front and center. Fast...

Product and Strategy Technology and Future Systems and Scaling

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