
Unsupervised Learning
Exploring the fascinating intersection of security, technology, and humans.
Daniel Miessler
Show overview
Unsupervised Learning has been publishing since 2015, and across the 11 years since has built a catalogue of 548 episodes. That works out to roughly 220 hours of audio in total. Releases follow a weekly cadence.
Episodes typically run twenty to thirty-five minutes — most land between 13 min and 30 min — though episode length varies meaningfully from one episode to the next. It is catalogued as a EN-US-language Technology show.
The show is actively publishing — the most recent episode landed 2 weeks ago, with 14 episodes already out so far this year. The busiest year was 2024, with 72 episodes published. Published by Daniel Miessler.
From the publisher
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.
Latest Episodes
View all 548 episodesEvolution, Lit RPG and AI Harnesses
The Missing Piece Is Ideal State
The Different Games OpenAI and Anthropic Are Playing
Debating the Morality of Dario Amodei
Rethinking AI Harnesses
Why We Need Some AI Model Controls
AI Predicts the Text of Answers
Most Companies Aren't Anywhere Near Ready for AI
We're All Building a Single Digital Assistant

Why AI Will Replace Knowledge Workers
A longer form discussion on exactly how and why AI will replace knowledge workers.Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

Why I Believe in SOTA Models Over Custom Ones
I think the future is cheaper and Open Source SOTA models combined with context, not custom, narrow models.Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

AI Quality Inversion
A troubling thought about what we will think about high-quality content in the future. Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

The Great Transition
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.Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

Starting 2026
A welcome back and early entry into 2026. Sponsored by: Knocknoc!Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

Judge AI based on Output, Not Mechanism
How we can use an output-based system to judge whether or not different kinds of technology achieve understanding or intelligence. Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

Humans Need Entropy
How humans and AI models both share the weakness of deterioration without novel inputs. Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

Why I Think Karpathy is Wrong on the AGI Timeline
Karpathy is confusing LLM limitations with AI system limitations, and that makes all the difference. Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

Novelty Exploration vs. Pattern Exploitation
How going from exploration to exploitation can help you as both a consumer and creator of everything.Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

Magnifying Time
Some thoughts on how novelty and attention magnify the time that we have. Become a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.

A Conversation With Harry Wetherald CO-Founder & CEO At Maze
➡ 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 ManagementWhy 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 VelocityHow 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 SecurityWhy 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 FirstHow 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 MinutesWhy 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. Subscribe to the newsletter at:https://danielmiessler.com/subscribe Join the UL community at:https://danielmiessler.com/upgrade Follow on X:https://x.com/danielmiessler Follow on LinkedIn:https://www.linkedin.com/in/danielmiessler Chapters: 00:00 – Welcome and Harry’s Background01:07 – The Real Problem: Remediation vs. Prioritization04:31 – Breaking Down Vulnerability Context and Threat Intel05:46 – Connecting Vulnerabilities to Developers and Workflows08:01 – Why Traditional Vulnerability Management Fails10:29 – Startup Lessons and The State of AI Agents13:26 – DARPA’s AI Cybersecurity Competition14:29 – System Design: Deterministic Code vs. AI16:05 – How the Product Works and Data Sources18:01 – AI as “Extra Eyes and Hands” in Security20:20 – Breaking Barriers: Rethinking Scale with AI23:22 – Building World Models for Defense (and Attack)25:22 – Attackers Move Faster: Why Context Matters27:04 – Phishing at Scale with AI Agents31:24 – Shrinking Windows of Vulnerability: From Days to Minutes32:47 – What’s Next for Harry’s Work34:13 – Closing ThoughtsBecome a Member: https://danielmiessler.com/upgradeSee omnystudio.com/listener for privacy information.