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Daniel Miessler: evaluation

1 Jun 2026 The Cognitive Revolution Inside Nathan's Second Brain: Daniel Miessler, Security Expert & Creator of PAI, Audits My AI Setup

“As the AI gets smarter and smarter, the specific ways you told it to do things will get Dumber and Dumber because it's us being egotistical and thinking our ideas are so cool with look, look how smart I made this skill when in fact AI could do it better.”

— Daniel Miessler

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Speaker
Daniel Miessler
Attribution
Verified speaker
Claim type
evaluation
Recorded
1 Jun 2026
Publisher
The Cognitive Revolution

Transcript context

…Well, I certainly know the better lesson, but tell me a better lesson next year. Yeah, so I've got a skill bitter lesson, engineering. Another thing that is scheduled, which is Kai's job, is to say, OK, so the concept of Richard had was your scaffolding. This is paraphrasing, but the scaffolding gets stupider and stupider as time goes on. As the AI gets smarter and smarter, the specific ways you told it to do things will get Dumber and Dumber because it's us being egotistical and thinking our ideas are so cool with look, look how smart I made this skill when in fact AI could do it better. So I'm constantly basically trying to figure out have I over engineered the skill? Have I over engineered the separation and all these different things. That's why I only have one work GitHub, because the smarter the AI gets, I think the more I can figure that out. So I'm a big scaffolding person. I've always been this way with like security testing methodologies. But yeah, the better the AI gets, the less it's going to need. So I'm always guarding against that. Yeah, that's cool. And then you just have it proposed changes to you and you approve them or do you allow you don't you don't allow them to auto implement those changes.…

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