Beyond the Hype: Cyber Readiness, Zero Trust, and an Unscripted Conversation - Rob Allen, Gibb Witham - SWN #568
Security Weekly Podcast Network (Audio)
Release Date: 03/31/2026
Executive Paralysis and Two Pre-Recorded RSAC 2026 Interviews from DigiCert and Okta - Amit Sinha, Ann Marie van den Hurk, Matt Immler - BSW #441
Security Weekly Podcast Network (Audio)
Most organizations don’t fail because of technology. They fail because decision authority is unclear in the first critical minutes. “Being careful” is often interpreted as waiting for certainty, but that delay creates exposure. How should executives make decisions under pressure? Ann Marie van den Hurk, Founder at Mind The Gap Advisory, joins Business Security Weekly to discuss how executive paralysis leads to business damage. Ann Marie will discuss: Where Paralysis Actually Comes From What “Being Careful” Looks Like in Practice Why the First 20 Minutes Matter How Paralysis Becomes...
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Beyond the Hype: Cyber Readiness, Zero Trust, and an Unscripted Conversation - Rob Allen, Gibb Witham - SWN #568
Security Weekly Podcast Network (Audio)
In the AI era, cybersecurity is undergoing a fundamental shift as AI agents transform both the speed and scale of attacks. In this interview, Gibb Witham, President and Chief Financial Officer of Hack The Box, explains why organizations must move beyond assumed AI capability toward measurable, validated cyber readiness for both humans and AI systems. Drawing on real-world benchmarks, agentic AI testing, and hands-on training, Witham outlines how security teams can safely adopt AI by proving performance under pressure. The discussion highlights why the future of cybersecurity depends on...
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Developing the Skills Needed for Modern Software Development - Keith Hoodlet, Shashwat Sehgal, Ron Rasin - ASW #376
Security Weekly Podcast Network (Audio)
The future of secure software is going through a mix of skills expected of humans and skills files created for LLMs. We might even posit that appsec as a discipline will fade (and that might not even be a bad thing!). Keith Hoodlet describes the skills he was looking for in building teams of security researchers and why there's still an emphasis on the ability to learn about and understand how software is built. But figuring out what skills will get you hired and what skills are valuable to invest in still feels daunting to new grads and others entering the security industry. We discuss where...
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Oops, all Interviews: Switching to Cyber, CISO Reflections, and the State of TPCRM - Alexandre Sieira, Lenny Zeltser, Helen Patton - ESW #452
Security Weekly Podcast Network (Audio)
Interview with Helen Patton about her new book, Switching to Cyber Helen joins us to discuss her second book, "Switching to Cyber." Her first book discussed strategies for handling various stages of the cybersecurity career, while this one, co-written with Josiah Dykstra, provides a guide for switching to cyber mid-career. Check out her book, Switching to Cyber: The Mid-Career Guide to Launching a Cybersecurity Career: and on the publisher's Interview with Lenny Zeltzer: Reflections on Being a CISO After a cybersecurity career in various roles, doing everything from product management to...
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Scam Baiting, AI, and the New Grift Economy, Part 2 - Rinoa Poison - SWN #567
Security Weekly Podcast Network (Audio)
In this two-part interview, Rinoa Poison explores the mechanics of modern scams, the role of AI in making them more convincing, and the growing world of scam baiting. She also discusses the tactics, technical setups, and safety considerations behind wasting scammers’ time. Visit for all the latest episodes! Show Notes:
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Scanning The Internet with Linux Tools - PSW #919
Security Weekly Podcast Network (Audio)
In this segment, we will explore some pretty awesome tools for scanning the Internet, with a focus on network edge devices. We'll bring it all together with Claude Code and look at some sample results. Tools include: Shodan | Passive recon — query existing scan data for exposed devices, services, and vulns | Passive (API) | Instant (no packets sent) ZMap | Host discovery — find live hosts with open ports | L4 (TCP SYN, UDP, ICMP) | Millions of packets/sec ZGrab2 | Application-layer handshakes — grab banners, certs, headers | L7 (30+ protocol modules) | Thousands of hosts/sec Nerva |...
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Say Easy, Do Hard - Crypto-Agility - BSW #440
Security Weekly Podcast Network (Audio)
With Q-day getting closer, regulatory guidance pushing firms to migrate to quantum security in the next five years, and an extensive remediation backlog waiting to be discovered, security leaders must start their quantum security migration today. Easier said than done. In this Say Easy, Do Hard segment, we discuss the quantum-safe journey using a framework for crypto-agility. In part 1, we define cryptographic agility, or crypto-agility for short, and why it's important. Crypto-agility is not just about transitioning to quantum-safe cryptography in the nimblest way possible, and it’s not...
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Scam Baiting, AI, and the New Grift Economy, Part 1 - Rinoa Poison - SWN #566
Security Weekly Podcast Network (Audio)
Rinoa Poison joins Security Weekly News to break down the world of scam baiting, how modern scams are evolving, and why AI is making fraud harder to spot. In this two-part conversation, she shares how scam baiters operate, the risks involved, and what everyday people should know. Visit for all the latest episodes! Show Notes:
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Why Proactive Security Is Far Better Than Patching - Erik Nost - ASW #375
Security Weekly Podcast Network (Audio)
So much of appsec’s efforts can be consumed by vuln management and a race to patch security flaws. But that’s more a symptom of the ease of scanning and the volume of CVEs. Erik Nost walks through the principles behind proactive security, why the concept sounds familiar to secure by design, and why organizations still struggle with creating effective practices for visibility. Resources Visit for all the latest episodes! Show Notes:
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Can AI help critical infrastructure, the state of the cyber market, and weekly news - Mike Privette, Kara Sprague - ESW #451
Security Weekly Podcast Network (Audio)
Interview with Kara Sprague - The AI Fix for Infrastructure’s Oldest Security Risks. Critical infrastructure, often built on decades-old systems and legacy code, remains vulnerable to cyberattacks. From pipelines and energy grids to transportation networks, we break down where critical infrastructure is vulnerable and how AI could potentially help strengthen defenses. Interview with Mike Privette - The State of the Cybersecurity Market Here at ESW, we use Mike Privette's Security, Funded newsletter to prepare for every news segment. His covers the latest fundings, acquisitions, public...
info_outlineIn the AI era, cybersecurity is undergoing a fundamental shift as AI agents transform both the speed and scale of attacks. In this interview, Gibb Witham, President and Chief Financial Officer of Hack The Box, explains why organizations must move beyond assumed AI capability toward measurable, validated cyber readiness for both humans and AI systems. Drawing on real-world benchmarks, agentic AI testing, and hands-on training, Witham outlines how security teams can safely adopt AI by proving performance under pressure. The discussion highlights why the future of cybersecurity depends on training, testing, and reinforcing human and AI operators together before they are trusted in critical environments.
This segment is sponsored by Hack The Box. Visit https://securityweekly.com/hacktheboxrsac to learn more about them!
As credential-based attacks continue to dominate headlines, many organizations are realizing that identity alone is no longer a sufficient control. This conversation explores the shift toward device-based access enforcement and why tying access to both user and device is becoming critical. We’ll discuss how this evolution is reshaping Zero Trust strategies across modern environments.
This segment is sponsored by ThreatLocker. Visit https://securityweekly.com/threatlockerrsac to learn more about them!
Visit https://www.securityweekly.com/swn for all the latest episodes!
Show Notes: https://securityweekly.com/swn-568