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Craig McCaskill
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Everything

Books and Ideas

4 posts

Communication and Influence

6 posts

Leadership and Culture

8 posts

Product and Strategy

10 posts

Systems and Scaling

5 posts

Technology and Future

6 posts

Thinking and Learning

10 posts
19 Apr, 2026
Featured
Technology and Future
19 Apr
Technology and Future
Featured

Toothpaste Back in Tubes: On opportunity cost, art, and what stays human →

The AI debate keeps leaving out the part that matters most: what gets made with the time it gives back. On opportunity cost, art, and what stays human.
25 Jan, 2026
Technology and Future
25 Jan
Technology and Future

When Seeing Is No Longer Believing →

We spent years worrying about deepfakes. Then we watched authentic video get contradicted by official statements, with media treating both as valid perspectives.
24 Aug, 2025
Featured
Technology and Future
24 Aug
Technology and Future
Featured

The Bubble That Knows It's a Bubble →

Railway Mania, dot-com, AI. Technology bubbles follow a pattern older than any of them. What's different this time is that everyone knows the script.
29 May, 2025
Featured
Technology and Future
29 May
Technology and Future
Featured

How to Think About AI →

Jensen Huang is right about AI's real impact on jobs, but most people are missing his deeper point about competitive advantage.
25 May, 2024
Featured
Technology and Future
25 May
Technology and Future
Featured

Playing Favorites - How AI Shapes Our Knowledge Without Us Noticing →

We're building a world where AI increasingly decides what information we see. These systems have a built-in bias toward the average, and it's narrowing what we collectively know.
23 Aug, 2023
Featured
Product and Strategy
23 Aug
Product and Strategy
Featured

The Great Enshittification - How Product Evolution Becomes Product Regression →

Platforms enshittify. The predictable pattern by which products get worse for users while their metrics keep climbing, and why the marginal user is usually to blame.
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Craig McCaskill © 2026