PODCAST · technology
Risky Business Features
by Risky Business Media
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.
Episodes
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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 recently, but that doesn’t give defenders the full picture they need to manage risks. Not all...
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How 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 it’s difficult for gangs to convert their ill-gotten crypto gains into cash they can...
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Hunting 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 through static analysis, deobfuscation and reconstructing multi-stage kill chains to…
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Who 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 responding to cyber incidents alongside US law enforcement gives him a unique perspective on…
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How 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 Perth. TeamPCP is the hacker group that has gone berserk in the software supply chain over…
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James 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 Terminator, an autonomous research system that generates and tests tens of thousands of…
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How 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 private inference works, from trusted execution environments and hardware attestation,...
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Benchmarks, 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 token costs might think frontier and open weight AI models are all interchangeable.…
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Fortibleed: 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 expanded into the discovery of an attack that targeted 400,000 Fortinet devices. As Ensar...
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What 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 open-weight LLMs are real, attackers don’t yet seem able to fully utilise them. This…
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Mythos 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 where both cloud and local models are used to orchestrate, triage outputs, and write...
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Pitching 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 language models have made it easier than ever to create software products, but despite...
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How 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 open weight models like DeepSeek, Kimi and Qwen. But now the US government is forcing...
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The 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. In the name of safety, both models were guardrailed up the wazoo, but that didn’t stop a...
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Why 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 install scripts and dynamic dependencies is a positive step forward… but it’ll take…
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Everything 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. Fears around outages or being hacked have been trumped by fears of being labelled an AI...
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Solo 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 had skilled up and was smashing global software supply chains in the highest profile...
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How 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. AI has made attackers faster, and “vibe coding” means the number of environments…
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How 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 episode, mistakes were made and lessons learned. It’s worth a podcast, too, because in our...
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NCSC’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 so far in the face of the AI “bugpocalypse”. As Ollie explains, organisations will need...
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What 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 tasks doesn’t deliver value, and avoiding all risk stalls progress. James and Brad...
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Mythos 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, having worked as a Distinguished Engineer at Google and then heading up security at Stripe....
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Solving 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 sorts of companies that are deploying AI. With everyone now in at least a large-scale pilot...
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A 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 problem for frontier labs! Any LLM-based product could have its competitive advantage...
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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 [un]prompted conference demonstrated how Anthropic’s Opus 4.6 could find and exploit…
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A 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 Engineering, and is former VP Eng and COO at Airtasker. He’s now an investor and advisor to…
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Mythos 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 finding and fixing exploits makes us safer. Show notes
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Mythos and 0day: A hacker’s perspective
In this episode of Risky Business Features, James Wilson chats to professional hacker Jamieson O’Reilly about Anthropic’s Mythos and the impact it could have on offensive security. Jamieson is CEO of DVULN and co-founder of Aether AI. He’s been hacking into organisations for more than a decade…
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What happens after North Korea infiltrates?
In this episode, investigative journalist Geoff White joins James Wilson for a look into the complex machine that is North Korea’s IT worker infiltration scheme. They discuss the interview process, what happens once the workers are actually hired, how value is maximised for the regime, and how…
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Why CISOs need to be more flexible in the AI era
In this episode, James Wilson chats with Brad Arkin (former CISO of Adobe, Cisco and Salesforce) to talk about the mounting pressure that CISOs are under in the AI era. Attackers are operating at unprecedented scale, and internal users are adopting AI faster than security teams can keep up. This...
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A Risky Biz Experiment: Hunting for iOS 0day with AI
In this sort-of-solo episode, James Wilson is “joined” by one of his OpenClaw AI agents for a chat about whether or not an LLM can understand, modify or even create a sophisticated nation-state grade iOS exploit kit. Technically this podcast is James having a conversation with himself, but the...
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Interview: Former NSA and CIA cyber leaders on offensive AI
In this interview you’ll hear former NSA executive Rob Joyce and former CIA cyber intelligence leader Andy Boyd talk to host Patrick Gray about how AI is changing the state of art in offensive security. Recorded in front of a live audience at the Decibel Oasis side event next door to the RSA...
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When disaster strykes
In this episode of Risky Business Features, James Wilson and Brad Arkin discuss the attack that devastated medtech company Stryker. It turns out the attackers used Microsoft’s inTune to wipe the company’s devices, but what else could they have weaponised? This podcast basically turned into an...
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MCP is Dead
James Wilson delivers his take on the state of the Model Context Protocol (MCP) in this solo episode of Risky Business Features. Despite MCP being the technology that made Large Language Models useful and AI Agents possible, the models have shown us they want to use something else instead. They...
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They don't break in, they log in. What's an enterprise to do?
In this podcast James Wilson chats with Brad Arkin about how enterprises can better deal with attackers logging in with valid credentials. Stolen identities, weak special-use credentials, and over-scoped API keys are the new zero-day and they’re abundantly available to attackers. Sadly, the...
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A ridiculously deep dive into the Coruna Exploits
Join James Wilson in this solo podcast as he takes a (ridiculously) deep dive into the Coruna exploit kit. James was a software engineer and senior manager at Apple for many years, so he has an intimate knowledge of iOS internals. He even worked alongside the people who wrote the software that…
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Being a wartime CISO
In this edition of Risky Business Features James Wilson chats with cohost Brad Arkin about what it’s like being a CISO for a global company when a war starts. How do you deal with a branch office full of important key material being abandoned? What about cloud infrastructure that’s in a data…
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What to do about North Korean remote workers
In this podcast James Wilson chats with Brad Arkin about North Korea’s sprawling fake IT worker ecosystem. From fake interviews, to stolen identities, basement laptop farms and IP-KVM tricks, the North Koreans are operating a whole employment fraud industry. Brad and James discuss how the scheme...
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Former Adobe, Cisco and Salesforce CISO talks AI pentesting
In this debut feature conversation in the Risky Business Features feed James Wilson sits down with Brad Arkin, the former CSO of Adobe, Cisco, and Salesforce, to talk all about AI pentesting. Finding and fixing bugs is great, but does it materially improve the overall security of a product?…
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History Repeats: Security in the AI Agent Era
AI agents are being deployed with the same trust-by-default architecture the early internet had. Same mistakes, MUCH faster timeline. OpenClaw has hit 180K+ GitHub stars. But in the past week: 341 malicious skills on ClawHub were distributing Atomic Stealer ZeroPath disclosed a Browser Relay vuln...
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ABOUT THIS SHOW
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.
HOSTED BY
Risky Business Media
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Frequently Asked Questions
How many episodes does Risky Business Features have?
Risky Business Features currently has 40 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Risky Business Features about?
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.
How often does Risky Business Features release new episodes?
Risky Business Features has 40 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Risky Business Features?
You can listen to Risky Business Features on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Risky Business Features?
Risky Business Features is created and hosted by Risky Business Media.
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