Technology

Risky Business Features

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:

Russia's AI-powered hacks are causing chaos in Ukraine Nov 02, 2026

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In this podcast Patrick Gray and The Grugq chat to Nazar Tymoshyk about Russia’s use of AI in recent state-back cyberattacks against Ukraine.

Nazar is the founder and CEO of Ukraine-based cybersecurity firm UnderDefence. He also spent the first few years of the war working for Ukraine’s CERT.

The three discuss the speed and impact of these automated attacks and how organisations can best prepare themselves against AI-scaled attacks.

This episode is also available on YouTube.

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What I learned from cheating clankers Oct 23, 2026

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In this solo Risky Business Features episode, James Wilson looks at the string of recent AI benchmark cheating escapades and how they’ve reshaped his thinking about LLMs and vulnerability research.

He explores the current benchmarks and exactly how agents go about gaming the testing system to achieve their tasks. And why understanding that has changed the way he interacts with his agents.

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Bug count sounds impressive... but means little Oct 02, 2026

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In this solo Risky Business Features episode, James Wilson explains why “number of bugs” fixed in any given update is a misleading metric. We’ve seen up to 1,000 individual bug fixes in a single update recently, but that doesn’t give defenders the full picture they need to manage risks.

Not all bugs are equally exploitable, so the industry needs to catch up to the bugpocalypse with more transparency. And maybe an entirely different approach to patching.

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How to launder illicit Bitcoin Sep 15, 2026

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In this podcast episode, investigative journalist Geoff White joins James Wilson to talk about what happens to the money after ransomware gangs get a payday.

The payment itself might be in the millions, but it’s difficult for gangs to convert their ill-gotten crypto gains into cash they can actually spend. Geoff explains the role of professional launderers and why cash-rich drug gangs are useful connections for crypto-rich cybercriminals.

They also dive into who operates these international laundering networks, other types of crime they enable, and whether this affects the argument of whether victims should be allowed to pay.

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Hunting software supply chain malware Sep 11, 2026

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In this podcast episode, OpenSourceMalware founder Paul McCarty joins James Wilson to explain how researchers find and analyse malicious packages, GitHub repositories and developer tools.

Paul walks James through static analysis, deobfuscation and reconstructing multi-stage kill chains to identify what attackers are trying to steal. They also discuss how LLMs make malware development easier while introducing operational security mistakes.

The pair examine DPRK tradecraft, blockchain-based payload delivery and what Paul calls Pollen Rider, which can reinfect developers through their own repositories.

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Who gets to hack the hackers? Sep 03, 2026

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In this podcast episode, Brad Arkin joins James Wilson to chat about the Trump administration’s call to let private entities conduct cyber operations against criminal groups.

Brad’s firsthand experience responding to cyber incidents alongside US law enforcement gives him a unique perspective on how government and private sector relationships work, and how this program could improve the ability of both sides to tackle cybercrime.

James and Brad also explore who might participate in these campaigns and whether the government will be able to effectively oversee them.

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How Brian Krebs doxxed TeamPCP Aug 28, 2026

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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 gone berserk in the software supply chain over the last year or so, stealing credentials to compromise developers, their software packages, and their repositories.

In this interview Brian talks about his Signal conversations with the group’s ringleader, the strange Cybercats community surrounding TeamPCP, and the passive DNS breakthrough that helped him unmask what he thinks are the ringleader’s true identities.

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Two Alleged ‘TeamPCP’ Hackers Arrested in Australia – Krebs on Security

James Kettle on inventing new attack techniques with LLMs Aug 17, 2026

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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 generates and tests tens of thousands of potentially new HTTP desync techniques. The Terminator, which makes use of Kettle’s own research methodology, has already come up with new desync methods that James hadn’t thought of before.

Kettle and Wilson discuss how to develop and evaluate machine-generated ideas without drowning in false positives, and why the most powerful part of the process is the discovery cascade, where one unexpected result becomes the seed for another.

The upshot is AI can conduct genuinely novel security research, but don’t expect to one-shot your way to an army of robot hackers.

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How private LLM inference actually works Aug 07, 2026

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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 execution environments and hardware attestation, to TLS termination and GPU isolation. Customers can verify the exact code and model processing their data, while Tinfoil and its infrastructure providers remain locked out.

That’s clever engineering… but who really needs it? Is private inference only useful if you’re doing something bad, or will it become a privacy baseline like TLS? James and Tanya discuss the costs and trade-offs, and how open weights make private inference more transparent and trustworthy.

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Benchmarks, borders and the true cost of AI regulation Jul 28, 2026

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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 open weight AI models are all interchangeable. That they can just banhammer them without causing any disruption. That’s far from the truth.

In this solo podcast, James Wilson looks beyond the US vs China AI race rhetoric and instead games out what the real world consequences of the US government slapping bans on AI models could be.

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