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Rating
5from
This podcast has
15 episodes
Language
EnglishPublisher
Risky Business MediaExplicit
No
Date created
2026/02/19
Latest episode
2026/04/20
Average duration
36 min.
Release period
5 days
Description
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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Check latest episodes from Risky Business Features podcast
A builder's perspective on Mythos and frontier models
2026/04/20
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 notes
Mythos and 0day: Fixing exploits is not safety
2026/04/17
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
Mythos and 0day: A hacker’s perspective
2026/04/13
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, and knows a thing or two about combining AI and offensive security.
Show notes
What happens after North Korea infiltrates?
2026/04/08
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 the money moves around. It’s even more diabolical than the headlines divulge.
Show notes
Lazarus Heist Podcast
Why CISOs need to be more flexible in the AI era
2026/04/03
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 requires CISOs to bend on things that would have otherwise been a hard-no in the past, and revisit some fundamental controls that might have seemed too difficult previously.
Show notes
A Risky Biz Experiment: Hunting for iOS 0day with AI
2026/03/31
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 exchange is illuminating. It turns out LLMs can really help with finding 0day, even in mature code repos like WebKit.
Show notes
Interview: Former NSA and CIA cyber leaders on offensive AI
2026/03/27
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 Conference in San Francisco, the trio also talk about why a series of iOS exploit chain leaks don’t seem to be stirring up a scandal.
Show notes
When disaster strykes
2026/03/23
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 incident review of the Stryker incident. Enjoy!
Show notes
MCP is Dead
2026/03/18
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 want to use the shell directly, and that is going to have serious cybersecurity consequences.
Show notes
They don't break in, they log in. What's an enterprise to do?
2026/03/12
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 solution here isn’t as simple as deploying phishing resistant MFA. Fixing this takes an enterprise identity strategy.
Show notes
A ridiculously deep dive into the Coruna Exploits
2026/03/11
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 the Coruna kit exploits!
This long-form solo podcast follows the chain of exploits from watering-hole website right through to full device compromise with many incredible leaps over security boundaries along the way. You’ve heard Coruna described as a sophisticated, nation state-grade exploit kit, and James will explain to you why that description is fitting.
Show notes
Being a wartime CISO
2026/03/06
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 centre that falls into enemy hands? And if your staff are okay, are any of your key suppliers going to face problems?
As you’ll hear, being a wartime CISO is less about adjusting your SIEM sensitivity because the Iranians are coming to get you, and more about figuring out how to deal with very real threats to life and infrastructure.
Show notes
What to do about North Korean remote workers
2026/02/27
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 works in practice and the technical detection challenges defenders now face, like dealing with stolen or borrowed identities, bribed verification checks and multi-person operational chains. They also dig into why enterprises are largely on the back foot, and why there’s no single product you can buy to solve this.
As the former CISO of Adobe, Cisco and Salesforce, Brad has some firsthand experience dealing with this stuff!
Show notes
Former Adobe, Cisco and Salesforce CISO talks AI pentesting
2026/02/19
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? What’s the point of a pentest if the tester can’t walk you through their findings when it’s over? Is “bugs per dollar spend” really the measure of value in security testing?
We hope you enjoy this podcast!
Show notes
History Repeats: Security in the AI Agent Era
2026/02/17
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 enabling cross-tab cookie theft
CrowdStrike, Cisco, and Bitdefender all published enterprise advisories
VirusTotal partnered with ClawHub to scan uploads
Korean tech firms (Kakao, Naver, Karrot) banned it on corporate networks
1,000+ Open PRs, 250+ less than 24 hours old.
But how does this thing actually work? Join James Wilson as he explains why banning these types of agents doesn’t work, why browser sessions are now API surfaces, and why your organisation needs to think of these issues early or be condemned to decades of catch-up programs.
Show notes
Podcast reviews
Read Risky Business Features podcast reviews
Laughedoutloud 2026/03/25
Top notch work
Excellent addition to the Risky podcasts
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