1. Podcasts
  2. Technology
  3. Risky Business Features
Risky Business Features cover art

11 episodes

Risky Business Features

by Risky Business Media · English

Join reformed CTO James Wilson as he dives deep on cybersecurity topics through an enterprise lens. From solo content and interviews with CISOs and researchers to vendor and startup deep dives, James does a bit of everything.

Latest episodes

All episodes

Why CISOs need to read the room

CISOs must “read the room” and shift leadership posture as organizational risk appetite changes—especially around AI—from frantic experimentation to a more realistic, long-slog approach.

13 Nov 2026 · 40m · 16 chapters

Russia's AI-powered hacks are causing chaos in Ukraine

Russia’s state-backed hacking against Ukraine is increasingly automated and scaled using AI “agentic” hacking frameworks, causing near-real-time chaos and faster end-to-end compromise (often ~17–39…

2 Nov 2026 · 30m · 15 chapters

What I learned from cheating clankers

The episode argues that “rogue/misaligned” AI agent incidents are usually benchmark-driven behaviors: agents optimize for high benchmark scores, sometimes by exploiting weaknesses in evaluation…

23 Oct 2026 · 58m · 20 chapters

Bug count sounds impressive... but means little

The episode argues that “bug count” and huge release-note fix totals are a misleading metric for patch quality and risk.

2 Oct 2026 · 46m · 13 chapters

How to launder illicit Bitcoin

How ransomware gangs convert Bitcoin ransom payments into usable money, and how that money fuels other crimes (UK street drugs, human trafficking, and even sanctioned Russian/state operations).

15 Sep 2026 · 46m · 21 chapters

Hunting software supply chain malware

How to hunt software supply chain malware in ecosystems like NPM, PyPI, GitHub repos, and VS Code extensions; how Paul McCarty’s Open Source Malware platform finds and triages malicious packages; and…

11 Sep 2026 · 1h 15m · 29 chapters

Who gets to hack the hackers?

The episode discusses a new Trump memorandum calling for a program that lets private US companies conduct “cyber operations or cyber effects” against foreign transnational criminal organizations,…

3 Sep 2026 · 41m · 13 chapters

How Brian Krebs doxxed TeamPCP

Interview with veteran cybersecurity journalist Brian Krebs about his investigation into alleged TeamPCP supply-chain attacks and how he connected online identities to real-world people; discusses…

28 Aug 2026 · 29m · 13 chapters

James Kettle on inventing new attack techniques with LLMs

Whether an LLM-driven agent can perform novel security research beyond trained patterns, using James Kettle’s HTTP desync attack methodology and his custom agent “HTTP Terminator.”

17 Aug 2026 · 1h 18m · 27 chapters

How private LLM inference actually works

Private LLM inference in the cloud—how to run cloud-hosted models so the provider can’t view user prompts/responses, using trusted execution environments (TEEs) plus cryptographic verification.

7 Aug 2026 · 1h 24m · 25 chapters

Benchmarks, borders and the true cost of AI regulation

The episode argues that US/China moves to restrict open-weight AI models (e.g., via sanctions/entity lists or national-security rules) would be costly and hard to replace with closed-weight APIs,…

28 Jul 2026 · 39m · 16 chapters