iCharles — Charles Botensten | AI, faith, triathlon, building in public

Architecting the Autonomous: Engineering the Loops That Drive AI Agents

The shift from prompting AI like Claude. Boris Cherny highlights this evolution, where developers manage continuous cycles that direct AI agents, focusing on architecture and to building automated loops marks a transition in software engineering toward intent-centric development.

The Economics of Token Exhaustion: Why Flat-Rate AI Subscriptions Collapsed

Subscriptions are so 2025 right, well... Trends seem to agree.

The 30-Day Head Start: Trump’s Frontier AI Executive Order

President of the United States of America, Donald J. Trump has pulled a rather "radical" moves towards AI, and this week has been no different.

AI Samples, the inevitable doom of AI: AI Companies’ Relentless Hunt for Training Samples, the Privacy Minefield, and the Looming Shadow of Contamination

AI Samples - Ouroboros of AI model training.

Videos

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Whiteboard

31:53

How I Burned Months Building a Salesforce Replacement With Claude

After $50,000 and five developers, Charles discovers Claude can scaffold a working CRM in minutes — then spends months learning why that's only half the problem.

Pivot

9:25

Why Prompting Skill Beats Coding Skill in the AI Era

After 307 days of live vibe-coding, I'm convinced the sharpest competitive edge isn't writing code — it's knowing exactly what to ask the model.

Whiteboard

27:00

How I Learned to Think Objectively After 10 Years of Unlearning

Charles Botensten maps the decade-long process of moving from emotional, distraction-driven thinking to something closer to objective reality — and shows exactly where most people get stuck.

Pivot

9:11