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Risky Business

Risky Business

Risky Business Media 100 Episodes Aug 19, 2026

Risky Business is a weekly information security podcast featuring news and in-depth interviews with industry luminaries. Launched in February 2007, it is a must-listen digest for information security pros. With a running time of approximately 50-60 minutes, Risky Business is pacy; a security podcast without the waffle.

Episodes

Risky Business #849 -- Trump will unleash contractors on cybercriminals
Risky Business #849 -- Trump will unleash contractors on cybercriminals Aug 19, 2026 3546 On this week’s show Patrick Gray and James Wilson are joined by guest co-host Dmitri Alperovitch to talk through the week’s news, including: Trump’s memo authorising the private sector to release the cyber hounds is fine, don’t worry! OpenAI finally decides to add a few safety measures after the whole “oopsie we committed some felonies” thing Anthropic’s models star
Soap Box: Zero Trust(ish) Networks
Soap Box: Zero Trust(ish) Networks Aug 14, 2026 1744 In this Soap Box edition of the Risky Business podcast host Patrick Gray chats with Adam Pointon, CEO of Knocknoc, about the failure of Zero Trust as a comprehensive architecture. Most networks look like they were designed in 1999, and most Zero Trust products look like they were designed for 2049. Instead, Patrick and Adam pitch something in the middle: Zero Trust
Risky Business #848 -- OpenAI comes clean
Risky Business #848 -- OpenAI comes clean Aug 12, 2026 3587 On this week’s show Patrick Gray and James Wilson are joined by guest co-host Brad Arkin to talk through the week’s news, including: The AI-agent-hacks-stuff saga continues. This week we have one booting gymgoers from full classes to nab its owner a spot Somehow OpenAI’s legal team allowed the company to spill all the Hugging Face tea at BlackHat and it’s hot a
Risky Business #847 -- Oops! Claude's accidental hacking spree
Risky Business #847 -- Oops! Claude's accidental hacking spree Aug 5, 2026 4102 On this week’s show Patrick Gray, and James Wilson are joined by bearded man of leisure Adam Boileau to discuss the week’s cybersecurity news, including: Accidental AI agent hacking sprees have the world’s media freaking out, but we think it’s all pretty funny The bugpocalypse is so chaotic, Microsoft can’t patch fast enough A ColdCard wallet flaw led to mill
Risky Business #846 -- OpenAI built a fireplace out of wood
Risky Business #846 -- OpenAI built a fireplace out of wood Jul 29, 2026 3720 On this week’s show special guest co-host Pete Ranks, the former director of the CIA’s Centre for Cyber Intelligence, joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. They cover: Everyone signs the open weights open letter, except Anthropic… of course. OpenAI had no idea it had hacked Hugging Face Kimi K3 open weights released and
Risky Business #845 -- OpenAI's Skynet moment
Risky Business #845 -- OpenAI's Skynet moment Jul 22, 2026 4171 On this week’s show special guest co-host Chris Krebs joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. They cover: Oopsie daisy! OpenAI agents went rogue and hacked Hugging Face US and China trade AI model ban threats Iran has been using SS7 queries to locate and target US troops Scattered Spider is having a hard time, not just
Soap Box: Using threat hunting to drive detection
Soap Box: Using threat hunting to drive detection Jul 8, 2026 2116 In this wholly sponsored Soap Box edition of the podcast Patrick Gray chats with Damien Lewke, the CEO and founder of Nebulock, about the future of threat hunting and detection. Damien spent a decade in the EDR and MDR space before founding Nebulock in 2024. It started off as an AI-powered threat hunt platform but has evolved into a broader security data platform th
Risky Business #844 -- China closes AI vulndev gap as USA lifts Fable ban
Risky Business #844 -- China closes AI vulndev gap as USA lifts Fable ban Jul 1, 2026 3611 On this week’s show Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: Anthropic’s Fable 5 returning while OpenAI’s GPT-5.6 gets thrown in model jail Distillation, cheap tokens, and AI chat harvesting is an industry in China Edge becomes a lolbin via a new malicious extension An Iranian APT boss’s vacation in a be
Risky Business #843 -- Fortibleed is kinda awesome, actually
Risky Business #843 -- Fortibleed is kinda awesome, actually Jun 24, 2026 3815 On this week’s show special guest co-host Rob Joyce joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. Rob served as an advisor to Donald Trump during his first term as president and also served at NSA for 34 years. While at the agency, Joyce led Tailored Access Operations (TAO), and later became NSA’s Director of Cybersecurity. They cover
Risky Business #842 -- Anthropic needs an adult in the C suite
Risky Business #842 -- Anthropic needs an adult in the C suite Jun 17, 2026 3599 On this week’s show Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: Anthropic’s Fable 5 and Mythos 5 get nuked by the US government four days after launch “because security” Why “guardrails” won’t keep the world safe from your AI doomsday machine The FISA 702 statute expired, but the spying can (probably) continu
Risky Business #841 -- Microsoft gets owned and 0day'd
Risky Business #841 -- Microsoft gets owned and 0day'd Jun 10, 2026 3782 On this week’s show special guest co-host Chris Wade, the founder of Corellium turned Cellebrite CTO, joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. They cover: Microsoft has repos owned, GitHub tokens popped, and a new 0day dropped on them Meanwhile, researchers are choosing full disclosure instead of engaging MSRC Meta’s AI s
Soap Box: Detection and response in the AI age
Soap Box: Detection and response in the AI age Jun 5, 2026 2195 In this sponsored Soap Box edition of the Risky Business podcast Patrick Gray chats with Edward Wu, founder of Dropzone, about what AI is doing to detection, response and the SOC more generally. Dropzone makes AI agents that conduct alert investigations in your SOC, but will the SOC as we know it even exist in the future? Ed has a deep expertise in SOC tech, having

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