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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
26 May, 2026
Systems and Scaling
26 May
Systems and Scaling

Introducing Posthorn: the missing layer in self-hosted email →

Five apps, five copies of the same Resend integration, five different ideas about what to do when a send fails. The missing layer between self-hosted apps and the provider you already picked.
24 Aug, 2025
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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.
24 Feb, 2025
Featured
Leadership and Culture
24 Feb
Leadership and Culture
Featured

The Science of Saying No - Frameworks and Execution →

The practical mechanics of prioritization: framework selection, implementation tactics, and the sustainability habits that let systems survive under pressure.
17 Feb, 2025
Featured
Leadership and Culture
17 Feb
Leadership and Culture
Featured

The Art of Saying No (Or At Least, Not Yet) →

The math of product is simple but brutal: too many demands, not enough resources. A case for saying no to the good so you can say yes to the great.
23 Aug, 2023
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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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