#248: The AI Cybersecurity Crisis, Dario Fights Back on Safety, OpenAI’s Monitoring Blind Spots & Claude Duet

From The Artificial Intelligence Show Paul Roetzer and Mike Kaput

AI found a 14-year-old flaw in the code behind an estimated 70% of websites, and within 12 hours of it leaking, Cloudflare saw millions of attempts to exploit it. In Episode 248, Paul Roetzer and Mike Kaput break down this AI cybersecurity crisis: what happened, why it cascaded across banks, infrastructure, and medical records, and the steps you can take now.

They also cover Dario Amodei's defense of Anthropic's safety record, outside evaluators finding gaps in OpenAI's safeguards, Meta's Muse data exposure, and Anthropic's IPO filing at a valuation approaching $2 trillion, plus product and funding news in the rapid-fire round.

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Show Notes: Access the show notes and show links here

Timestamps:

00:00:00 — Intro

00:05:17 — The AI Cybersecurity Crisis Is Here

00:29:55 — Dario Defends Anthropic’s Safety Record

00:45:50 — Outside Evaluators Find Gaps in OpenAI’s AI Safeguards

00:56:57 — Marketing AI Institute’s 10-Year Anniversary

01:05:28 — Meta’s Muse Agent Found to Expose User Data

01:11:35 — Anthropic Releases Its Own Personal Agent

01:14:59 — Inside Anthropic’s IPO

01:19:29 — AI Use Case Spotlight

01:32:02 — AI Product and Funding Updates

This episode is brought to you by AI Academy Day 2026.

AI keeps changing, how do you keep your people learning at the same pace? Join Paul Roetzer, Mike Kaput, and SmarterX head of learning Jessica Miller on Thursday, November 19 at 12pm ET for a first look at the next phase of AI Academy by SmarterX. Register at SmarterX.ai/AcademyDay

This episode is also brought to you by the MAICON 2026 On-Demand Bundle. Couldn’t make it to Cleveland, or want to rewatch?

The MAICON 2026 On-Demand bundle gives you more than two dozen recorded main-stage and featured sessions (12+ hours) from this year’s Marketing AI Conference, ready to watch on your own schedule. Grab it at MAICON.AI

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