Risky Business Features
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- 13. Nov. 2026
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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.
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Why CISOs need to read the room
In this podcast episode, Brad Arkin joins James Wilson to discuss how security leaders should respond when the mood changes. The rush to adopt AI meant finding ways to let the business move fast, but lately a …
Shownotes
In this podcast episode, Brad Arkin joins James Wilson to discuss how security leaders should respond when the mood changes. The rush to adopt AI meant finding ways to let the business move fast, but lately a little more caution seems to be creeping back in.
The pair explore how to spot those shifts, know when to start making a fuss, and change approach without simply mirroring the boss’s latest concern.
Show notesRussia's AI-powered hacks are causing chaos in Ukraine
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 …
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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.
Show notesWhat I learned from cheating clankers
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 …
Shownotes
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.
Show notes- OpenAI incident account and grading distinction
- METR and Redwood independent assessment
- FrontierCode original evaluation methodology
- BrowseComp aggregation experiments
- Sonnet 4 point 5 coding scaffold and parallel selection
- Opus 4 point 6 BrowseComp setup
- BrowseComp evaluation awareness and contamination investigation
- Sonnet 5 point 5 effort and review subagents
- FrontierCode 1 point 1 revision and rubric changes
- Astra launch comparison and effort conditions
- Original OSWorld task construction and worked examples
- Sonnet 4 point 6 system card
- Original OSWorld benchmark
- OSWorld 2 environment and evaluation design
- GPT 5 point 4 comparator table
- GPT 5 point 5 comparator table
- BrowseComp construction and grading paper
- GPT 5 point 6 single model and Ultra configurations
- METR investigation and artifact evidence
- Released task definition
- Released scorer for reference only
- OpenAI paper sections 3 point 1 to 3 point 3
- OpenAI accompanying explanation
- Sycophancy to Subterfuge paper
- Training a Misaligned Reward Seeker and evaluation appendix
- GPT 5 point 2 AIME result
Bug count sounds impressive... but means little
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 …
Shownotes
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.
Show notesHow to launder illicit Bitcoin
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 …
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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.
Show notesHunting software supply chain malware
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 …
Shownotes
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.
Show notesWho gets to hack the hackers?
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 …
Shownotes
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.
Show notesHow Brian Krebs doxxed TeamPCP
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 …
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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.
Show notesJames Kettle on inventing new attack techniques with LLMs
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 …
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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.
Show notesHow private LLM inference actually works
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 …
Shownotes
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.
Show notesBenchmarks, borders and the true cost of AI regulation
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 …
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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.
Show notesFortibleed: The bleeding edge of AI cybercrime
In this podcast episode SOCRadar CISO Ensar Seker and James Wilson chat about the company’s deep dive into the Fortibleed campaign. A small investigation into a curiously open directory on an unknown server …
Shownotes
In this podcast episode SOCRadar CISO Ensar Seker and James Wilson chat about the company’s deep dive into the Fortibleed campaign. A small investigation into a curiously open directory on an unknown server expanded into the discovery of an attack that targeted 400,000 Fortinet devices.
As Ensar says, each time the SOCRadar team pulled a single thread, it led to a tapestry of AI-enabled cybercrime. They uncovered custom initial access, persistence and packet sniffing tools, as well as direct links to the INC and Lynx ransomware operations. Most interesting though is the use of AI to design, implement and operate all aspects of the campaign across a team of 20 individual actors. Operating more like a modern software company than a traditional cybercrime gang, Fortibleed serves as our first in-depth look at the future of cybercrime.
Show notesWhat to do 'til the bugpocalypse gets here
In this podcast episode Brad Arkin joins James Wilson to discuss how defenders can get ahead of the late-running bugpocalypse. While we’re confident the offensive cybersecurity capabilities of frontier and …
Shownotes
In this podcast episode Brad Arkin joins James Wilson to discuss how defenders can get ahead of the late-running bugpocalypse. While we’re confident the offensive cybersecurity capabilities of frontier and open-weight LLMs are real, attackers don’t yet seem able to fully utilise them. This creates a window of opportunity for defenders to tackle the threat.
There are a few well-funded and seemingly overlapping industry efforts under way including Athena, Akrites, and Patch the Planet. But, as Brad says in this interview, there’s too much focus on fixing bugs and traditional vulnerability triage, and not enough on exploring how to make entire classes of vulnerabilities inert.
Show notesMythos on your desk? Using local LLMs for code reviews
In this podcast episode James Wilson chats with Karsten Nohl about his research into using local LLMs to replace cloud AI in security code reviews. In essence, Karsten created a hybrid code reviewing system …
Shownotes
In this podcast episode James Wilson chats with Karsten Nohl about his research into using local LLMs to replace cloud AI in security code reviews.
In essence, Karsten created a hybrid code reviewing system where both cloud and local models are used to orchestrate, triage outputs, and write reports. In this system, only the local LLMs have source code access, with the cloud models used to manage the local models.
In this “source-local” review technique, the source code never leaves the local endpoint, which is a requirement for some reviews. But funnily enough, Karsten was able to use this system to generate findings that were as impressive as when using frontier models directly.
In a nutshell, Karsten proved it’s possible to use locally-hosted, open-weight models running on commodity hardware to produce findings comparable to those discovered by frontier cloud models.
This episode is also available on YouTube.
Show notesPitching security startups to VCs in the AI era
In this podcast Patrick Gray and James Wilson chat with Decibel Partners founder and Managing Partner Jon Sakoda to talk about pitching cybersecurity startups to VC firms in the AI age. Coding agents and large …
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In this podcast Patrick Gray and James Wilson chat with Decibel Partners founder and Managing Partner Jon Sakoda to talk about pitching cybersecurity startups to VC firms in the AI age.
Coding agents and large language models have made it easier than ever to create software products, but despite this, the bar for what interests an investor is still largely the same. Everyone can run the marathon, but it’s usually the same few folks who finish first.
So tune in to hear Jon share with us his wisdom on when to start the conversation with investors, how to leverage the experience of the founder community, and what founders should watch out for.
This episode is also available on YouTube
Show notesHow using open weight models can blow up in your face
In this podcast episode James Wilson and Brad Arkin talk about how to safely use open weight large language models in the enterprise. The cost of frontier models was already driving interest in freely available …
Shownotes
In this podcast episode James Wilson and Brad Arkin talk about how to safely use open weight large language models in the enterprise. The cost of frontier models was already driving interest in freely available open weight models like DeepSeek, Kimi and Qwen. But now the US government is forcing Anthropic to pull its Fable and Mythors models from the market, the argument for having greater control over your own AI stack is stronger than ever.
But as you’ll hear in this episode, the model itself is just one component of the complex tech stack you’ll need to spin up if you want local inference. There’s a lot of moving parts, each of which comes with its own supply chain risks.
So whether you’re hosting these models on your own hardware or via a SaaS provider, there’s a lot to ponder!
Show notesThe state of the art in AI model jailbreaks
In this solo podcast episode, James Wilson breaks down the current state of AI model jailbreaks. If you’ve somehow missed the story, last week Anthropic released its Fable 5 and Mythos 5 models to the public …
Shownotes
In this solo podcast episode, James Wilson breaks down the current state of AI model jailbreaks.
If you’ve somehow missed the story, last week Anthropic released its Fable 5 and Mythos 5 models to the public. In the name of safety, both models were guardrailed up the wazoo, but that didn’t stop a bunch of jailbreakers from figuring out how to bypass at least some of their safety restrictions.
In response to these guardrail bypasses the White House issued an export control directive on the models, citing national security concerns. But was the Trump administration right to do this? Do these jailbreaks represent a threat to the security of the USA, or was the export restriction overkill? Tune in to find out!
Show notesWhy NPM v12 won’t stop supply chain attacks
In this podcast episode, James Wilson is joined by Open Source Malware Security co-founder Paul McCarty to talk about the supply chain attack mitigations coming in NPM v12. NPM disabling (by default) auto-run …
Shownotes
In this podcast episode, James Wilson is joined by Open Source Malware Security co-founder Paul McCarty to talk about the supply chain attack mitigations coming in NPM v12.
NPM disabling (by default) auto-run install scripts and dynamic dependencies is a positive step forward… but it’ll take years for this new version to be adopted, and these changes do nothing to prevent malicious packages being imported into projects.
Further, Paul thinks disabling these features by default will introduce friction that will cause them to be re-enabled. When the choice is “this builds” and “this is less prone to malware”, the former will always win.
Show notesEverything is getting much worse, much faster
In this podcast Brad Arkin joins James Wilson to talk about how the fear of being left behind in the AI era means enterprises are taking risks that would have been considered insane just a couple of years ago …
Shownotes
In this podcast Brad Arkin joins James Wilson to talk about how the fear of being left behind in the AI era means enterprises are taking risks that would have been considered insane just a couple of years ago.
Fears around outages or being hacked have been trumped by fears of being labelled an AI laggard.
So where are we all going? Say hello to tech debt-riddled, vibe-coded apps, crazy dependencies on AI providers, and an emerging threat landscape that can’t be mitigated by a contemporary SOC. Sounds like fun, eh?
Show notesSolo podcast: A deep dive on TeamPCP
In this solo episode, James Wilson takes a detailed look at TeamPCP. It started off by launching clumsy attacks against misconfigured Kubernetes clusters in September 2025. But by February this year, TeamPCP …
Shownotes
In this solo episode, James Wilson takes a detailed look at TeamPCP.
It started off by launching clumsy attacks against misconfigured Kubernetes clusters in September 2025. But by February this year, TeamPCP had skilled up and was smashing global software supply chains in the highest profile attacks of 2026.
TeamPCP upskilled and turned the software development ecosystem into its personal credential harvesting machine.
Here’s how TeamPCP did it, and what we can learn from it.
Show notesHow to survive supply chain attacks
In this podcast James Wilson chats with Brad Arkin about why software supply chain attacks have gone from rare, once-in-a-while disasters to an operational problem affecting mainstream enterprises almost daily …
Shownotes
In this podcast James Wilson chats with Brad Arkin about why software supply chain attacks have gone from rare, once-in-a-while disasters to an operational problem affecting mainstream enterprises almost daily.
AI has made attackers faster, and “vibe coding” means the number of environments pulling packages from the internet has gone to the moon. It also means legacy tooling that seeks out the bad packages and cleans them up isn’t enough. Package cooldown windows won’t fix this either.
But all hope is not lost! Tune in to this podcast to find out how you can get a grip on the disaster de jour!
Show notesHow the CopyFail disclosure went sideways
In this episode, Theori’s Brian Pak and Andrew Wesie join James Wilson to discuss why the CopyFail exploit was publicly disclosed before Linux distributions had their patches ready. As you’ll hear in this …
Shownotes
In this episode, Theori’s Brian Pak and Andrew Wesie join James Wilson to discuss why the CopyFail exploit was publicly disclosed before Linux distributions had their patches ready. As you’ll hear in this episode, mistakes were made and lessons learned. It’s worth a podcast, too, because in our opinion this incident foreshadows the inevitable problems that open source software will face in the unfolding vulnpocalypse.
Show notesNCSC’s Ollie Whitehouse on surviving the "bugpocalypse"
In this edition of Risky Business Features Ollie Whitehouse, the CTO of the UK’s National Cyber Security Centre, joins Patrick Gray and James Wilson to talk about why “patch faster” will only get organisations …
Shownotes
In this edition of Risky Business Features Ollie Whitehouse, the CTO of the UK’s National Cyber Security Centre, joins Patrick Gray and James Wilson to talk about why “patch faster” will only get organisations so far in the face of the AI “bugpocalypse”.
As Ollie explains, organisations will need to reduce internet-facing attack surface and make better architecture decisions as 0day discovery speeds up.
This episode is also available on YouTube.
Show notesWhat a great agentic AI deployment plan looks like
In this podcast James Wilson and Brad Arkin workshop the advice they think the industry needs to hear when it comes to deploying agentic AI in the enterprise. Relegating agentic AI to non-sensitive and low-risk …
Shownotes
In this podcast James Wilson and Brad Arkin workshop the advice they think the industry needs to hear when it comes to deploying agentic AI in the enterprise.
Relegating agentic AI to non-sensitive and low-risk tasks doesn’t deliver value, and avoiding all risk stalls progress. James and Brad discuss the phases of AI adoption and contrast what a great plan looks like, versus an overly cautious one.
Show notesMythos smythos! How to find 0day with lesser models
In this podcast James Wilson chats with Niels Provos about his research into using older AI models to successfully hunt for 0day vulnerabilities. Niels has had a long and prolific career in cybersecurity …
Shownotes
In this podcast James Wilson chats with Niels Provos about his research into using older AI models to successfully hunt for 0day vulnerabilities. Niels has had a long and prolific career in cybersecurity, having worked as a Distinguished Engineer at Google and then heading up security at Stripe.
His interest in AI bug hunting was piqued recently when one of the Mythos 0day vulnerabilities that received lots of attention happened to be in code he wrote for the OpenBSD project 27 years ago.
It got him thinking: Are these frontier models really that magical? Or could we replicate their findings with some clever orchestration instead of relying on the model’s smarts to find bugs with a single prompt?
As it turns out, this was worth looking into. Niels’ orchestration framework, Iron Curtain, works extremely well.
This episode is also available on YouTube
Show notesSolving the AI agent identity problem
In this podcast James Wilson and Brad Arkin chat about emerging trends in AI agent identity and credential management. Brad was formerly the CISO of Adobe, Cisco and Salesforce, and is now working with all …
Shownotes
In this podcast James Wilson and Brad Arkin chat about emerging trends in AI agent identity and credential management. Brad was formerly the CISO of Adobe, Cisco and Salesforce, and is now working with all sorts of companies that are deploying AI.
With everyone now in at least a large-scale pilot of agentic AI, the issue of how to manage agent identities and credentials is still an unsolved problem. But, some interesting patterns are emerging.
Show notesA deep dive on AI model distillation attacks
In this solo episode of Risky Business Features James Wilson explores how distillation techniques are both a legitimate way to train smaller models, as well as a way to steal model capabilities. It’s not just a …
Shownotes
In this solo episode of Risky Business Features James Wilson explores how distillation techniques are both a legitimate way to train smaller models, as well as a way to steal model capabilities. It’s not just a problem for frontier labs! Any LLM-based product could have its competitive advantage stolen through these attacks.
James covers:
- High-level concept of distillation
- Why it matters including close/open-weight/open-source explanation
- Types of distillation and the prompts used
- The distillation pipeline end to end
- Distillation at scale and mitigation techniques
- Hardware resource constraints for distillation
- Self-Instruct: Aligning Language Models with Self-Generated Instructions
- Alpaca: A Strong, Replicable Instruction-Following Model
- Vicuna: An Open-Source Chatbot Impressing GPT-4 with 90%* ChatGPT Quality
- Orca: Progressive Learning from Complex Explanation Traces of GPT-4
- Zephyr: Direct Distillation of LM Alignment
- Stealing Part of a Production Language Model
- Microsoft probes if DeepSeek-linked group improperly obtained OpenAI data, Bloomberg News reports
- Detecting and preventing distillation attacks
Feature Interview: Nicholas Carlini, Anthropic
In this episode, Anthropic’s Nicholas Carlini joins Patrick Gray and James Wilson to talk about advancements in AI-driven vulnerability research and exploit development. Nicholas’ talk at the recent …
Shownotes
In this episode, Anthropic’s Nicholas Carlini joins Patrick Gray and James Wilson to talk about advancements in AI-driven vulnerability research and exploit development.
Nicholas’ talk at the recent [un]prompted conference demonstrated how Anthropic’s Opus 4.6 could find and exploit vulnerabilities in popular open source projects. In the short few weeks since then, Anthropic announced a new model that’s already identifying hundreds of bug fixes across critical software. Nicholas talks us through the work he does at Anthropic, what’s possible and the limitations with current frontier models, and where this goes from here.
This episode is also available on YouTube
Show notesA builder's perspective on Mythos and frontier models
In this episode, James Wilson is joined by entrepreneur and investor Yaniv Bernstein to discuss Anthropic’s Mythos through the lens of startups and growing businesses. Yaniv is Google’s former VP of …
Shownotes
In this episode, James Wilson is joined by entrepreneur and investor Yaniv Bernstein to discuss Anthropic’s Mythos through the lens of startups and growing businesses. Yaniv is Google’s former VP of Engineering, and is former VP Eng and COO at Airtasker. He’s now an investor and advisor to startups and he co-hosts The Startup Podcast.
Show notesMythos and 0day: Fixing exploits is not safety
In this episode, James Wilson is joined by Brad Arkin who provides a CISO’s perspective on Anthropic’s Mythos. As former CISO at Adobe, Cisco and Salesforce, Brad’s perspective challenges the notion that …
Shownotes
In this episode, James Wilson is joined by Brad Arkin who provides a CISO’s perspective on Anthropic’s Mythos. As former CISO at Adobe, Cisco and Salesforce, Brad’s perspective challenges the notion that finding and fixing exploits makes us safer.
Show notes
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