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Daniel Miessler

Unsupervised Learning is about ideas and trends in Cybersecurity, National Security, AI, Technology, and Culture—and how best to upgrade ourselves to be ready for what's coming.

Unsupervised Learning

I think the future is cheaper and Open Source SOTA models combined with context, not custom, narrow models.

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Why I Believe in SOTA Models Over Custom Ones

A troubling thought about what we will think about high-quality content in the future. 

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AI Quality Inversion

There are a bunch of different transitions happening right now—all at the same time, all (I think) heading in the same direction. Here is a long-form exploration of the various pieces.

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The Great Transition

A welcome back and early entry into 2026. 
 
Sponsored by: Knocknoc!

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Starting 2026

How we can use an output-based system to judge whether or not different kinds of technology achieve understanding or intelligence. 

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Judge AI based on Output, Not Mechanism

How humans and AI models both share the weakness of deterioration without novel inputs. 

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Humans Need Entropy

Karpathy is confusing LLM limitations with AI system limitations, and that makes all the difference. 

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Why I Think Karpathy is Wrong on the AGI Timeline

How going from exploration to exploitation can help you as both a consumer and creator of everything.

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Novelty Exploration vs. Pattern Exploitation

Some thoughts on how novelty and attention magnify the time that we have. 

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Magnifying Time

➡ Stay Ahead of Cyber Threats with AI-Driven Vulnerability Management with Maze:
https://mazehq.com/
 
In this conversation, I speak with Harry about how AI is transforming vulnerability management and application security. We explore how modern approaches can move beyond endless reports and generic fixes, toward real context-aware workflows that actually empower developers and security teams.
 
We talk about:
 
The Real Problem in Vulnerability Management
Why remediation—not just prioritization—remains the toughest challenge, and how AI can help bridge the gap between vulnerabilities and the developers who need to fix them.
 
Context, Ownership, and Velocity
How linking vulnerabilities to the right applications and teams inside their daily tools (like GitHub) reduces friction, speeds up patching, and improves security without slowing developers down.
 
AI Agents and the Future of Security
Why we should think of AI agents as “extra eyes and hands,” and how they’re reshaping everything from threat detection to system design, phishing campaigns, and organizational defense models.
 
Attackers Move First
How attackers are already building unified world models of their targets using AI, and why defenders need to match (or exceed) this intelligence to stay ahead.
 
From Days to Minutes
Why the tolerance for vulnerability windows is shrinking fast, and how automation and AI are pushing us toward a future where hours—or even minutes—make the difference.
 
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https://danielmiessler.com/upgrade
 
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https://x.com/danielmiessler
 
Follow on LinkedIn:
https://www.linkedin.com/in/danielmiessler
 
Chapters:
 
00:00 – Welcome and Harry’s Background
01:07 – The Real Problem: Remediation vs. Prioritization
04:31 – Breaking Down Vulnerability Context and Threat Intel
05:46 – Connecting Vulnerabilities to Developers and Workflows
08:01 – Why Traditional Vulnerability Management Fails
10:29 – Startup Lessons and The State of AI Agents
13:26 – DARPA’s AI Cybersecurity Competition
14:29 – System Design: Deterministic Code vs. AI
16:05 – How the Product Works and Data Sources
18:01 – AI as “Extra Eyes and Hands” in Security
20:20 – Breaking Barriers: Rethinking Scale with AI
23:22 – Building World Models for Defense (and Attack)
25:22 – Attackers Move Faster: Why Context Matters
27:04 – Phishing at Scale with AI Agents
31:24 – Shrinking Windows of Vulnerability: From Days to Minutes
32:47 – What’s Next for Harry’s Work
34:13 – Closing Thoughts

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A Conversation With Harry Wetherald CO-Founder & CEO At Maze

[ Subscribe to the Podcast: iTunes | Android | RSS ] InfoSec news Feds paid over 1M to get into San Bernardino iPhone Continued fallout from Panama papers 3.2 million servers vulnerable to JBoss attack which is being used in SamSam ransomware attacks MIT launches internal bug bounty platform | https://threatpost.com/mit-launches-experimental-bug-bounty-program/117618/ NSA recommends out-of-band taps […]
 
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:: Unsupervised Learning: Episode 37 appeared originally on danielmiessler.com.
 
 :: Subscribe to Unsupervised Learning---my weekly show where I handpick the best stories from infosec and technology, and talk about why they matter.

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Unsupervised Learning: Episode 37

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