Down the Security Rabbithole Podcast (DtSR)

Rafal (Wh1t3Rabbit) Los
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Mar 24, 2026 • 46min

DtSR Episode 698 - Leadership in a High Stakes CISO Role

TL;DR: This week's guest is Alex Hutton - who has been leading security teams in high-stakes organizations for years and is bringing his experience to you. We discuss leadership, risk, and several leadership topics you'll want to take notes on.YouTube video: https://youtube.com/live/FRBbnWVyO_QHave something to say? Let's hear it.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Mar 17, 2026 • 44min

DtSR Episode 697 - The Precarious Evolution of the CISO Role

TL;DR: On this episode of the pod, G. Mark Hardy joins Jim, James, and Rafal to talk about the precarious evolution of the role of the CISO. We even delve into the definition and purpose of risk, and find some there, there.YouTube video: https://youtube.com/live/_gpV4XilTocHave something to say? Let's hear it.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Mar 10, 2026 • 25min

DtSR Episode 696 - Zero Trust CyberSecurity Shenanigans

Rob Allen, CPO of ThreatLocker and zero trust endpoint advocate, talks platform evolution from deny-by-default allow-listing to ringfencing, network control, Detect (EDR), patching and MDR. He covers AI risks, scaling policies for many agents, reducing alert noise, and why prevention-first security reshapes consolidation and TCO.
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Mar 3, 2026 • 50min

DtSR Episode 695 - Cyber Is Headed for a Market Meltdown

TL;DR: Is cybersecurity headed for a market meltdown? Are we watching the bubble pop? Patrick Dennis joins Rafal to give some observations, analyze and provide guidance on what's happening, and what's to come. Buckle that chin strap, it's going to get crazy.YouTube video: https://youtube.com/live/bhtvOSv48JcHave something to say? Let's hear it.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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8 snips
Feb 24, 2026 • 46min

DtSR Episode 694 - Seasonal Martyrdom and Cyber Burnout

Ryan Halstead, director of cyber operations who builds playbooks to reduce burnout, and Rebekah Wilke, a fintech security leader who scales teams and programs. They unpack cyclical “martyr” firefighting around audits and headlines. They discuss personality types that chase incidents. They highlight playbooks, intake, AI and leadership boundaries to curb recurring stress and protect career longevity.
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Feb 17, 2026 • 60min

DtSR Episode 693 - The Most Important AI Conversation

TL;DR: This is one of the most relevant AI conversations, in the moment. Gadi Evron joins me to talk about how AI is not just changing everything, but how it's actually going to impact what you're doing - from security to everything else. Tune in, this is a critical conversation.YouTube: https://youtube.com/live/t48sX54QCwIHave something to say? Let's hear it.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Feb 10, 2026 • 39min

DtSR Episode 692 - Ran Nahmias the Perpetual Entrepreneur

TL;DR: What's it like to be an entrepreneur your entire career? Always trying something new, always doing something different? Ask Ran Nahmias, someone who's been around long enough to have done it all, and he's not done yet.YouTube Video: https://youtube.com/live/qngve0dmd7MHave something to say? Let's hear it.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Feb 3, 2026 • 39min

DtSR Episode 691 - How to Make External Security Testing Useless

TL;DR: Today, Julian Brownlow Davies rejoins the pod (Ep 688) to continue the conversation about 3rd party external security testing. It's strong opinions and tales of woe all around.Episode 688: https://dtsr.buzzsprout.com/2153215/episodes/18498795-dtsr-episode-688-looking-for-meaning-in-the-signalYouTube video: https://youtube.com/live/6ZCPNXR_5u0Have something to say? Let's hear it.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Jan 27, 2026 • 44min

DtSR Episode 690 - Defenders of the Internet Pipes

TL;DR: This week's guest is Matt Carothers who works at a major Internet provider. We talk about defending, strategy, and some of the interesting topics that come with the job. If you have Internet at home, or at the office, or on the go - this episode is for you. There will probably be a part 2.YouTube: https://youtube.com/live/tJcjtgn759gHave something to say? Let's hear it.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Jan 20, 2026 • 52min

DtSR Episode 689 - Off the Rails - Social Media is Evil

Kevin Thompson, a product management leader at a major AI platform and a seasoned Scoutmaster, joins the discussion on the dark side of social media. He warns how these platforms can harm kids, radicalize communities, and limit meaningful discourse. The conversation dives into age restrictions, algorithm-induced extremism, and the challenge of fostering resilience in youth. Thompson reflects on the need for parental guidance in navigating online harms and offers a hopeful perspective on generational adaptability amid technological shifts.

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