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Risky Business Features

Risky Business Media
Artificial Intelligence
Supply Chain Attacks
Cybersecurity
Mythos
Openclaw
Anthropic
North Korea
AI Agents
NPM
Open Weight Models
Bug Bounties
Openai
Identity and Access Management
Coruna Exploit Kit
Enterprise Security
Teampcp
HTTP Desync Attacks
Trusted Execution Environment
Private Inference
AI Penetration Testing

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.

PublishesTwice weeklyEpisodes36Founded6 months ago
Number of ListenersCategory
Technology

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Artwork for Risky Business Features

Latest Episodes

In this podcast episode, James Wilson chats with Brian Krebs about the investigation that led him from recycled cybercrime handles and old forum records to the true identity of TeamPCP’s alleged leader in Perth.

TeamPCP is the hacker group that has... more

In this podcast episode, James Wilson chats with PortSwigger’s Director of Research James Kettle about using an LLM to develop genuinely new attack techniques.

Kettle has built what he calls the HTTP Terminator, an autonomous research system that g... more

In this podcast episode James Wilson chats with Tinfoil co-founder Tanya Verma about how you can run a powerful LLM in the cloud without the inference provider seeing your prompts.

Tanya talks James through how private inference works, from trusted... more

The US government is flirting with the idea of regulating most open weight models out of existence. What would that mean for everyone who’s currently using them?

Policymakers who just look at the benchmarks and token costs might think frontier and ... more

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Recent Guests

James Kettle
Director of Research
PortSwigger
Episode: James Kettle on inventing new attack techniques with LLMs
Tanya Verma
Cryptography engineer, co-founder of Tinfoil
Tinfoil
Episode: How private LLM inference actually works
Ensar Seker
CISO of SOCRadar
SOCRadar
Episode: Fortibleed: The bleeding edge of AI cybercrime
Karsten Nohl
Security researcher, founder of Security Research Labs (now part of Alurity)
Security Research Labs / Alurity
Episode: Mythos on your desk? Using local LLMs for code reviews
Jon Sokoda
Managing partner at Decibel Partners
Decibel Partners
Episode: Pitching security startups to VCs in the AI era
Paul McCarty
Co-founder and maintainer of Open Source Malware
Open Source Malware
Episode: Why NPM v12 won’t stop supply chain attacks
Brian Pak
CEO of Theori
Theori
Episode: How the CopyFail disclosure went sideways
Andrew Wesie
CTO of Theori
Theori
Episode: How the CopyFail disclosure went sideways
Ollie Whitehouse
Chief Technology Officer
National Cyber Security Centre (NCSC)
Episode: NCSC’s Ollie Whitehouse on surviving the "bugpocalypse"

Host

James Wilson
Host of Risky Business Features

Reviews

5.0 out of 5 stars from 46 ratings
  • Top notch work

    Excellent addition to the Risky podcasts

    Apple Podcasts
    5
    Laughedoutloud
    United States5 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Strong technical rigor with varied guest perspectives.
Great for sponsors seeking a security-forward, executive audience.
Shows depth and practical cybersecurity insights for enterprise audiences.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#229
United States/Technology
Apple Podcasts
#115
United Kingdom/Technology
Apple Podcasts
#86
Australia/Technology
Apple Podcasts
#26
Philippines/Technology
Apple Podcasts
#34
Saudi Arabia/Technology
Apple Podcasts
#34
New Zealand/Technology

Talking Points

Recent interactions between the hosts and their guests.

James Kettle on inventing new attack techniques with LLMs
Q: What is the role of the cascade in ensuring the research stays productive and avoids dead ends?
Cascade ensures that discoveries aren't treated in isolation but are analyzed for root causes, potential accidental origins, and how they map back to the developer's mental models. This process helps identify new attack spaces and keeps the research aligned with real-world exploit potential rather than chasing noise.
James Kettle on inventing new attack techniques with LLMs
Q: What makes AI capable of producing genuinely novel security research, and where do humans fit in?
AI can aid by surfacing patterns and proposing hypotheses, but humans are needed to judge novelty, assess feasibility, and guide the cascade with domain knowledge. The model helps explore vast hypothesis space, but verification, interpretation, and strategic direction still require expert researchers to avoid false positives and ensure meaningful, exploitable results.
James Kettle on inventing new attack techniques with LLMs
Q: So how did you begin encoding your research methodology for the AI to follow?
The process started by breaking down the methodology into a stateful sequence—ideation, evaluation, weaponization—and then adding a cascade that analyzes how discoveries arise and what deeper causes exist. I fed the system HTTP RFCs, chunked into small units, and used paired sentences to generate structured hypotheses, then evaluated thousands of vectors against live targets.
How private LLM inference actually works
Q: Can you explain how TLS termination in the TE works and why it matters for security?
TLS termination inside the TE ensures that the encryption ends at the secure boundary, leaving zero plaintext data outside the TE, which is crucial for maintaining end-to-end confidentiality of the transcript.
How private LLM inference actually works
Q: How is data kept private during interaction with the model given the need for caching and performance?
KV caching is salted per end user to prevent cross-user leakage; transcripts remain stateless in the TE, and any caching is designed to avoid revealing sensitive information about other users' prompts.

Audience Metrics

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Frequently Asked Questions About Risky Business Features

What is Risky Business Features about and what kind of topics does it cover?

This show leans into enterprise-focused cybersecurity stories, practical defense insights, and in-depth technical dives. Episodes frequently explore AI in security—from private inference and local LLM deployments to the implications of open-weight models and AI-enabled threats—alongside governance, risk management, and software supply chain topics. Notable strengths include high-technical depth delivered with real-world context, guest lineups spanning researchers, CISOs, and industry leaders, and a willingness to tackle both tactical guidance and strategic industry shifts. Listeners who want actionable security architectures, threat intelligence perspectives, and VC/startup guidance in the AI era are likely to find it especially valuable.

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1. Risky Bulletin
2. Risky Business
3. Darknet Diaries
4. SANS Internet Stormcenter Daily Cyber Security Podcast (Stormcast)
5. Click Here

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Risky Business Features launched 6 months ago and published 36 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Risky Business Features?

Recent guests on Risky Business Features include:

1. James Kettle
2. Tanya Verma
3. Ensar Seker
4. Karsten Nohl
5. Jon Sokoda
6. Paul McCarty
7. Brian Pak
8. Andrew Wesie

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