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Risky Business

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Risky Business is a weekly information security podcast featuring news and in-depth interviews with industry luminaries. Launched in February 2007, Risky Business 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.

Latest episodes

Soap Box: HD Moore talks OT security, frontier fearmongering and more

In this sponsored Soap Box edition of the Risky Business podcast Patrick Gray chats with industry legend HD Moore about how his company runZero wound up being used heavily to discover OT devices in enterprise networks. They also talk about the vulnpocalypse and how frontier lab fearmongering is reminiscent of the collective freakout when HD released the Metasploit exploit framework back in 2003. T

29 Sep 2026 · 34 min
Risky Business #854 -- We're Jevpilled

THE RISKY BUSINESS WEEKLY SHOW IS NOW ON HIATUS FOR TWO WEEKS AND WILL RETURN OCTOBER 14 On this week’s show Patrick Gray and James Wilson are joined by Adam Boileau to talk through the week’s news, including: Google’s Gemini finally did some crimes OpenAI admits more agents did silly things because “alignment” US Treasury’s Scott Bessent rules out a liability waiver for the frontier labs, saying,

23 Sep 2026 · 54 min
Risky Business #853 -- We're all gonna die, apparently

On this week’s show Patrick Gray and James Wilson are joined by former US Cyber Command executive director turned PwC’s Cyber, Data & Technology Risk leader Morgan Adamski to talk through the week’s news, including: More tech guys penned more open letters and AI will destroy us all! Another Wednesday, another congregation of OpenAI agents on wikis… yawn OpenAI agents were behind the headscratching

16 Sep 2026 · 59 min
Snake Oilers: watchTowr, XBOW and CoreView

In this edition of the Snake Oilers podcast three vendors stop by to pitch the audience on their products: watchTowr : We’re all familiar with watchTowr’s research, but what do they actually do? XBOW : The AI pentesting company pitches its approach CoreView : Your M365 tenant is probably a security disaster. Tame it with CoreView! This episode is also available on YouTube . Show notes

11 Sep 2026 · 42 min
Risky Business #852 -- Cyber Command wants to buy shells

On this week’s show Patrick Gray and James Wilson are joined by guest co-host Robby Winchester from SpecterOps to talk through the week’s news, including: ID verification company IDScan was breached and 153m driver licenses wound up for sale online. Cue the barrage of lawsuits The US government plans to pay private contractors to conduct military hacks The US accuses China of distillation attacks,

9 Sep 2026 · 1 h 3 min
Risky Business #851 -- Agents are just ones and zeros, and tigers are just atoms

On this week’s show Patrick Gray and James Wilson are joined by guest co-host The Grugq to talk through the week’s news, including: Two alleged TeamPCP hackers got arrested in Australia The White House has a plan to boost security for water facilities, but we can’t see it working OpenAI keeps the ol’ Hugging Face discourse going for another week with an incident debrief Tech companies write anothe

2 Sep 2026 · 58 min
Risky Business #850 -- Widespread AI-enabled attacks target Siemens PLCs

On this week’s show Patrick Gray and James Wilson are joined by guest co-host Ollie Whitehouse, the CTO of the UK’s NCSC, to talk through the week’s news, including: Iranian hackers take down a small-scale power generator in the UK Siemens PLCs in critical US sectors are also being targeted… We’re stumped on who could be behind that one, too. Microsoft fixed a CVSS 10 deserialisation bug in Entra

26 Aug 2026 · 1 h 2 min
Risky Business #849 -- Trump will unleash contractors on cybercriminals

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 start a turf war when given the same

19 Aug 2026 · 59 min
Soap Box: Zero Trust(ish) Networks

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(ish) networks, where Zero Trust

14 Aug 2026 · 29 min
Risky Business #848 -- OpenAI comes clean

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 and delicious More details emerge abou

12 Aug 2026 · 59 min
Risky Business #847 -- Oops! Claude's accidental hacking spree

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 millions in Bitcoin theft, but the back sto

5 Aug 2026 · 1 h 8 min
Risky Business #846 -- OpenAI built a fireplace out of wood

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 they’re massive! Why a more aggressive

29 Jul 2026 · 1 h 2 min
Risky Business #845 -- OpenAI's Skynet moment

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 because of Microsoft’s GDID And much, muc

22 Jul 2026 · 1 h 9 min
Soap Box: Using threat hunting to drive detection

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 that can answer questions, drive h

8 Jul 2026 · 35 min
Risky Business #844 -- China closes AI vulndev gap as USA lifts Fable ban

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 beautiful place goes wrong Much, much more!

1 Jul 2026 · 1 h 0 min
Risky Business #843 -- Fortibleed is kinda awesome, actually

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: The surprisingly well done For

24 Jun 2026 · 1 h 3 min
Risky Business #842 -- Anthropic needs an adult in the C suite

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) continue! NPM v12 delivers some protection aga

17 Jun 2026 · 59 min
Risky Business #841 -- Microsoft gets owned and 0day'd

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 support agent allowed a staggering 20,000

10 Jun 2026 · 1 h 3 min
Soap Box: Detection and response in the AI age

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 previously led AI/ML detection e

5 Jun 2026 · 36 min
Risky Business #840 -- Microsoft walks back researcher threats

On this week’s show special guest co-host Andy Boyd joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. Andy is the CEO of REDLattice, which makes the Paragon “intelligence collection and reconnaissance” solution. They cover: Adversaries are tracking US troop locations with commercially available location data A new Signal phishing campaign is going after message backups

3 Jun 2026 · 1 h 6 min