Risky Business Features – Details, episodes & analysis

Podcast details

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Risky Business Features

Risky Business Media

Technology

Frequency: 1 episode/5d. Total Eps: 33

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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Apple Podcasts

🇫🇷 France - technology
30/07/2026
#78
🇨🇦 Canada - technology
18/07/2026
#86
🇬🇧 Great Britain - technology
18/07/2026
#99
🇫🇷 France - technology
17/07/2026
#99

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https://crfm.stanford.edu/2023/03/13/alpaca.html
1 share
https://arxiv.org/abs/2403.06634
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Score global : 48%

Publication history

Monthly episode publishing history over the past years.

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Former Adobe, Cisco and Salesforce CISO talks AI pentesting

Thursday, February 19, 2026 • Duration 25:55

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!

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History Repeats: Security in the AI Agent Era

Tuesday, February 17, 2026 • Duration 29:56

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.

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Being a wartime CISO

Friday, March 6, 2026 • Duration 31:36

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.

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What to do about North Korean remote workers

Friday, February 27, 2026 • Duration 27:55

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!

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MCP is Dead

Wednesday, March 18, 2026 • Duration 36:42

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.

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They don't break in, they log in. What's an enterprise to do?

Thursday, March 12, 2026 • Duration 32:02

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.

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A ridiculously deep dive into the Coruna Exploits

Wednesday, March 11, 2026 • Duration 01:17:45

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.

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When disaster strykes

Monday, March 23, 2026 • Duration 40:00

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!

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Interview: Former NSA and CIA cyber leaders on offensive AI

Friday, March 27, 2026 • Duration 15:04

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.

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A Risky Biz Experiment: Hunting for iOS 0day with AI

Tuesday, March 31, 2026 • Duration 56:10

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.

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Risky Business Features – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Risky Business Features – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Shared links between episodes and podcasts

Other15

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Other15

Apple Podcasts

Youtube5

Spotify