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Notes From The Workshop

AI's Confidence Problem Is Your Problem Too
Oct 9, 2026

AI's Confidence Problem Is Your Problem Too

AI systems are projecting certainty they haven't earned. The gap between what AI promises and what it actually delivers is exactly the trap that kills smart businesses.

AI artificial intelligence founder decisions tech skepticism AI tools risk management AI verification decision-making
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Automation Passes the Check and Fails the Job.
Aug 25, 2026

Automation Passes the Check and Fails the Job.

Automated systems keep telling you everything is fine. Meanwhile, devices brick, alt text misleads, and AI agents burn $20K without a strategy. The problem isn't the tool. It's mistaking a passing score for actual quality.

automation AI tools product quality founder judgment AI agents software development operations
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The Addiction Economy Wants Your Team
Aug 23, 2026

The Addiction Economy Wants Your Team

AI tools, safety regulations, and gospel music have nothing obvious in common. But pull the thread and they're all saying the same thing: the most dangerous products are the ones people can't stop using even when they know it's hurting them.

ai tools developer productivity engineering team management ai coding team health technical leadership founder operations
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Your AI Stack Is Already Obsolete
Aug 10, 2026

Your AI Stack Is Already Obsolete

Every AI tool you're betting on right now was built for a world that's actively expiring. Here's what that means for the decisions you're making this quarter.

AI strategy technical debt automation risk founder decisions infrastructure AI integrations systems thinking
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The Machine Is Watching. Now What?
Aug 9, 2026

The Machine Is Watching. Now What?

AI is tracking your screen, your routes, your code context, and your browsing history. The question isn't whether to let it in. It's whether you control what it learns about you.

AI strategy data ownership context architecture founder decisions AI tools privacy product thinking automation
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AI Does the Work. Who Checks the Work?
Jul 9, 2026

AI Does the Work. Who Checks the Work?

AI is writing more of your code, making more of your decisions, and failing more quietly than ever. The problem isn't capability. It's that nobody built the checkpoint.

AI automation engineering quality control LLM agents software development risk management operations
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