Down the Security Rabbithole Podcast (DtSR)

TL;DR: Howard Holton's back for part 2 of this 2-part special on the cybersecurity market, procurement's role, innovation, and now with 100% more AI discussion (drink up). Will it be Idiocracy? Or Star Trek? I know what I think.YouTube video (still sorry for the crap quality): https://youtube.com/live/q15xAwcPur8Have 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

TL;DR: Buckle up. Howard Holton, CEO of GigaOm, joins for a 2-part special on the cybersecurity market, innovation, market saturation, and more. What an absolute blast of a podcast.YouTube video (apologies for the crap quality): https://youtube.com/live/q15xAwcPur8Have 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

TL;DR: Returning guest Gadi Evron joins the crew to talk about the latest bomb dropped by Anthropic - "Mythos". Allegedly, this model could bring about the vulnerability apocalypse, or something. Let's dive into it.YouTube Video: https://youtube.com/live/RxY0Zj2UtLwHave 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

TL;DR: Do you have a trusting relationship with your cyber VAR, reseller, or integrator? Most of us don't, and that's because the erosion of trust has been ongoing for the last decade. So when Josh Jones, Chris Roche, and Yonesy Nunez get together to work on a problem, you know it's worth your time to listen. On this episode, we dive into how we got here, how bad the problem is - and most importantly, what we can do about it.YouTube Video: https://youtube.com/live/0umF7Bv3ra4Have 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

TL;DR: Starting off the 700 series is Adrian Sanabria, long-time analyst, and industry insider. Adrian's SubStack post ( https://substack.com/home/post/p-189699798 ) makes an interesting distinction between 'work' and 'tasks'; then he goes on to explain how AI will apply. Fascinating conversation recorded live from Zero Trust World, 2026 sponsored by ThreatLocker.YouTube Video: <shortly available>Have 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

TL;DR: THANK YOU. I can't believe I'm dropping episode 700. It's been a journey since September 2011 - so many amazing and unbelievable guests, conversations, and life lessons. So much incredible content that ages like fine wine, thank you to my friends James Jardine and Jim Tiller for doing this thing.Thank you to all of YOU for listening, sharing, and rating us.This is the industry's premier podcast for all things related to our profession. Here's to another 700.YouTube video: https://youtube.com/live/bUnz763Iq90Have 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

TL;DR: As I continue to post content recorded in Orlando at Zero Trust World 2026, I bring you a live recorded episode with Marcus Hutchins. It's an interesting discussion that is no doubt polarizing, but no less interesting. Enjoy!We are ONE EPISODE away from 700, thanks for being along for the ride!YouTube Video: (coming shortly)Have 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

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

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

TL;DR: This week's podcast is live'ish from Zero Trust World 2026, put on by ThreatLocker. It's a lively conversation with their CPO Rob Allen who can't help himself but mess with my recording equipment. Shenanigans ensue. You'll love it.YouTube video: https://youtu.be/aOP6IT8OiDIHave something to say? Let's hear it.Show Sponsor: ThreatLockerAllow what you need, block everything else... Including ransomware.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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

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

TL;DR: We've all experienced it - either you're the one, or you know someone, who works themselves to death. Whether it's "part of the job" or part of the job - it always leads to the same end. Rebekah Wilke and Ryan Halstead join James and I to talk through a very timely and critically important topic from a leadership perspective.Big thanks to my guy Josh Jones for the excellent connection.YouTube Video: https://youtube.com/live/Adpyja9KIkUHave 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

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

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

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

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

TL;DR: Social media is corrupting our kids, radicalizing your neighbors, and being basically evil with no checks. This episode is an "off the rails" discussion on a not-so-clearly Cyber Security topic, with us diving deep and getting a little angry. Thanks to Kevin Thompson for joining us and sharing his qualified opinion as a dad and experienced Scout Master.YouTube: https://youtube.com/live/RXzAVG98T6sHave 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

TL;DR: Grab your favorite note-taking thing, this week's pod features Julian Brownlow Davies of BugCrowd and it's chock full of things you'll want to look up. We tackle how red teaming and external 3rd party testing fits into a current security strategy, and how finding signal in the noise is just the beginning.YouTube video: https://youtube.com/live/aNz-qPmWf7g1Have 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

TL;DR: This week's episode is a special one. I (Rafal) revisit episode 100 with the one and only Dan Geer. Some shows are "in the moment", some are timeless. This show is timeless. Dan's wisdom and insights are as applicable today as they were 12 years ago. Crazy, right? Fun story - I ran into Dan at Black Hat conference a few years ago and asked him what he would say is 'different' since we recorded that episode... his response? "My beard is longer". Solid GOLD.Listen in. Take notes.Have 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

TL;DR: On today's pod, Rob Allen of ThreatLocker makes his triumphant return to derail us straight into a conversation about legacy systems and why he's still supporting WindowsXP. Right, you read that right. A great conversation ensued, and I'm glad we were able to record this one. Enjoy.From us to you, thank you for following along this year, and we wish you a happy new year, and all the best in 2026!YouTube video: https://youtube.com/live/dFO1NTo1MGcHave 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

TL;DR: In part 1 of 2, Gadi Evron joins the show and chats with Jim and Rafal on the topic of the "AI Cataclysm". What does that even mean? Listen in - but it's part to do with how AI is changing the attacker model (level of effort, expertise required, timeline) and what defenders should start to think about. Part 2 is coming soon, standby.YouTube Video: https://youtube.com/live/izX0jOUpKJMHave 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

TL;DR: This week's show features Aaron Costello, and is all about an analog from real-world attacks on humans, applied to AI "agents". I know what you're thinking - computers are supposed to be more difficult to trick, right? Right... no. Attacks such as this where computers try to be "helpful" (just like humans) are probably more common than we'd like to think. Give this a listen, it's a hoot.YouTube video: https://youtube.com/live/fM88jSkamDQHave 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

TL;DR: On this episode, it's just Jim and Rafal talking about how sometimes you just need to take a big step back from your day job and touch some grass. Our chosen profession is, demanding, to say the least. So let's take a minute to acknowledge what we're really thinking. Unfiltered, raw, and straight from our heads to your ears, enjoy.YouTube video: https://youtube.com/live/ULTq1pzckFgHave 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

TL;DR: This week's pod features a conversation with the Jay Jacobs, whom had previously been on the show talking about this very topic (vulnerability ranking/scoring) many, many years ago. If you missed Episode 297 check it out, it's crazy how far (or not) we've come since that conversation.YouTube Video: https://youtube.com/live/cpL9ZYbwkesHave 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

TL;DR: John Rafal & Jim as we welcome Dustin Lehr to talk about the state of AppSec and how we got here. We discuss vulnerabilities, accountability, culture, and a host of other things. It's a caffein-fueled episode, so buckle in!Youtube video: https://youtube.com/live/yoBIQ_sIawIHave 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

TL;DR: We heard RSnake's take on CVSS and CVEs and such, now let's hear Brian "Jericho" Martin's take. The gloves are off, and the opinions go native when we take this episode live. Brian doesn't pull any punches, and apparently I'm the only one without a pocket full of $2 bills?Sorry for the explicit rating, that's Brian's fault.YouTube Video: https://youtube.com/live/2-3Jzks5myc?feature=shareHave 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

TL;DR: Patching. Your least favorite thing. Well, it turns out that most of the work we have been doing in the last 20+ years has been for nothing. Robert "RSnake" Hansen's theory, backed by a lot of data, seems to point to a much bigger problem in cyber, and it's time we talk about it.Rob's Closing Keynote that started this conversation: https://youtu.be/80ZtAsuC4v4?si=-liUcLX4adz092yPYouTube Video: https://youtube.com/live/k4kvKWZVh78Have 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

TL;DR: This week's pod features your favorite hosts reflecting on how security has lost its way. When everything is a catastrophe, nothing is. When every breach is world-ending, none of them matter. Have we completely lost the plot? Prepare to have a good think.YouTube Video: <coming soon>Have 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

TL;DR: On this week's pod - Sean Scranton and Shawn Tuma make a return appearance to talk about Cyber (Security) Insurance. Some see it as the answer to cyber's problems, while others see it as just another question. Which is it? Is it just a matter of perspective? Listen in and find out!YouTube Video: https://youtube.com/live/GiuheFiFO78Have 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

TL;DR: This week's pod is all about healthcare-related data that is bought and sold the world over - and how you this data can be utilized while still preserving privacy. In this mind-blowing segment, John Kuhn of Integral joins Jim and I to talk about the vast quantities of data that's bought, sold, and aggregated for healthcare research - and how it can be used for good, while still preserving people's privacy (or what's left of it - debate ensues).YouTube Video: https://youtube.com/live/aa1xKEvhS5E?feature=shareHave 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

TL;DR: If you've ever wondered what goes through the mind of a top-tier CISO, wonder no longer. This week's episode features Trey Ford talking a little nostalgia, and a little of what's on his mind as a CISO. Fantastic episode, shout out to BugCrowd for the episode.Youtube video: https://youtube.com/live/uFl45Tb93gY?feature=shareHave 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

TL;DR:  Let's talk, err, lament, Third Party Risk programs. Who has time for these, and is there any real value in identifying 3rd party risks? Or is it just all theater for the lawyers? Paul Farley joins Jim, James and Rafal to chop it up.Dive in with us, and see what you think.YouTube Video: https://youtube.com/live/Le23nkaybfEHave 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

TL;DR:  This week's episode is what happens when I go on vacation and have a little time to think. So here we go - let's talk about this Jaguar Land Rover was compromised and ransomware spread. The damage has been 'extensive' to the point where they stopped everything... are there any lessons here?Linkshttps://www.theguardian.com/business/2025/sep/20/jaguar-land-rover-hack-factories-cybersecurity-jlrhttps://www.theguardian.com/business/2025/sep/20/jaguar-land-rover-hack-factories-cybersecurity-jlrhttps://www.reuters.com/en/tata-motors-jlr-return-manufacturing-after-cyber-attack-2025-09-29/YouTube link: https://youtube.com/live/1wjwskUrztkHave 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

TL;DR: This podcast features our friend Bo Birdwell who sits down with us to explain the ins and outs of the new DFARS CMMS update. Jim and Bo cover a lot of ground, and James and I are along for the ride asking questions.Great episode if you're in the space, worrying about what this latest update means to you.YouTube Video: https://youtube.com/live/0cl1S4f3g8EHave 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

TL;DR: This week's returning guest is Doug Cavit, but this time he's here to talk about the Internet apocalypse. Partly driven by AI, but mostly we discuss automated content generation, bots, and consumption as we reach the conclusion that it's all coming crashing down... sooner than we'd like.YouTube Video: https://youtube.com/live/tUJgdrh3ws8Have 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

TL;DR: Michael Reichstein joins the pod this week to talk about "rock star CISOs" and those who trade equity for their souls. It's an interesting discussion but this one comes with a warning label: If you're easily offended, do not listen to this.Michael's post that started this conversation: https://www.linkedin.com/posts/mreichstein_cybersecurity-leadership-businessethics-activity-7361753110983135233-YSctYouTube video: https://youtube.com/live/N1mD_HLYDxUHave 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

TL;DR: This week's pod features our favorite former analyst Anton Chuvakin, and an AppSec OG Jeff Williams as we tackle the subject of AppSec's favorite new acronym - ADR. What is it? Why is it? Should it be? We answer all these questions and more, and laugh along the way a bit too.YouTube Video: https://youtube.com/live/69xeGDoDYbULinksContrast's latest threat report (referenced in the show)An in-depth ADR Explainer (helpful!)Run-Time Security Explained (for those wanting to learn more)Have 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

TL;DR: This week's returning guest is the man, the myth, the Alpaca farmer, Philippe Humeau of CrowdSec. Life comes at you fast, threats come at you faster. The good news is - defenses can keep up. Listen in, then go check out CrowdSec!YouTube video: https://youtube.com/live/7Xc99bXCfwQHave 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

TL;DR: This week's guest is Dr Sam Liles - who's been CISO'ing since most of us have been in the industry. Sam gets it, and he has some perspective on what's going on with all this market consolidation. What is it good for? He's got some things to say, and he's not shy about it.YouTube: https://youtube.com/live/ROEA6z5Q-skHave 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

TL;DR: This week's show is a testament to surviving a week of Hacker Summer Camp out in Las Vegas. I have an interview with Ray Canzanese, Jr. (again, because y'all love him) and a bit of my take-away / rant from the week I spent out in the desert.  Enjoy, I hope you made it home safe and learned something. Good God it was hot.YouTube Video: ( standby, waiting on me to edit )Thanks again to my friends at Netskope!Have 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

** Early release, due to Black Hat Conference and RaffCon XVIII.TL;DR: This episode is all about #RaffCon. Ever wanted to know what the heck it is? Well, Raffael Marty and I break it down, give you a little history, and reminisce. As we got into Black Hat week, this is the perfect precursor to #RaffCon XVIII.YouTube video: https://youtube.com/live/jwArV_EwuZcHave 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

TL;DR: This is one of the most important episodes we've done on this podcast. The CISO and CIO have a complicated, dynamic, and often ugly relationship - but what should it be like? How can the two work together and evolve their roles together, for the benefit of everyone in the business? Larry Whiteside, Jr. ( Co-Founder and President at Confide) and Dennis McDonald ( Chief Information & Security Officer at Jack Henry ) lay down a conversation that's worth a repeated listen.YouTube video: https://youtube.com/live/g2F6BNSm2vkHave 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

TL;DR: This week's conversation is all about the Customer Success team featuring Nick Puetz and Steve Dakhe. These guys have significant seat time building, operating, and perfecting the CSM role - and we're here to talk about it. What is a CSM? Why do they exist? And what is their role in customer engagement? Listen in, find out!YouTube: https://youtube.com/live/lCen-1Vt_K8Have 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

TL;DR: This week we took a sit-down with serial entrepreneur, Will Gragido. Will has been a part of several innovative start-ups, and is now onto his next one. He's a product innovator with a pragmatic sense of what customers need, and he's here to give you the run-down of what drives him, what got him here, and things you should think about if you're thinking of setting off on your own.YouTube video: https://youtube.com/live/qkAi6Nj8kIIHave something to say? Let's hear it.Show Sponsor: ThreatLockerAllow what you need, block everything else... Including ransomware.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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

TL;DR: Did you miss us? Yes, we're back with Sam Masiello and we're talking about whatever is on his mind. Well ...there's geopolitics and Iranian hackers and frankly we need to talk about what it means for your security program.Thanks for joining us, Sam!YouTube Video: https://youtube.com/live/H-4ZktBIUDEHave something to say? Let's hear it.Show Sponsor: ThreatLockerAllow what you need, block everything else... Including ransomware.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.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

TL;DR:  This week's episode came from my (Rafal) brain. I've been reading far too much LinkedIn, and the "influencer" postings have been making me crazy. So, here we are. We talk through some of these posts, many of which are AI generated I think, and have a little fun with it. Call it...therapy.YouTube Video: https://youtube.com/live/uZVfkge8bQEHave 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

TL;DR: On this episode, part 4 of our AI series, we are once again joined by Raja Mukerji, Jeff Collins, and John Dickson to discuss what it means to think about security for AI. Is it something completely different? Is it something same-'ol? Or - is it a bit of both. And what aren't we thinking about when it comes to securing AI?YouTube video: https://youtube.com/live/vUJIOrX0kHcHave 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

TL;DR: This week I bring John Dickson back to join Jeff Collins and Raja Mukerji as we talk through the following:What can AI do, for cyber security, that we can't do with current tools?What is the model for incorporating AI into cybersecurity - are we replacing people? augmenting people? both? neither?Where is AI the strongest in these use-cases today, and where is the promise for 12 - 36 months out?What are the LIMITATIONS for AI in cybersecurity? Are these short-term limitations, or long-term?Youtube: https://youtube.com/live/Tv_Lx76rl58Have 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

TL;DR: This week John Dickson returns to go deeper down the AI rabbit hole with special guest Erik Bloch as we dive into a more technical explanation of AI, how this innovation differs from other similar concepts, previous tech innovations, and some of the commercial vs consumer use-cases where AI is best suited. It's a deeper discussion, and we will for sure have a part 3, and likely 4 coming soon.YouTube video: https://youtube.com/live/QXi6ed2NKhcHave 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

TL;DR: So - Artificial Intelligence (AI)...incomprehensible good, or catastrophic evil? Both? And what does that depend on? This episode is the start of a series wherein we explore the potential good or bad of AI, what the dependencies are. and what kinds of branches of discussion there could be. Join us as we discuss a generational topic, with some of our best guests starting with John Dickson.Required listening: Episode 654 w/Sounil Yu ( https://dtsr.buzzsprout.com/2153215/episodes/17193885-dtsr-episode-654-can-we-teach-machines-discretion )Bonus, since none of you read this ... what's John's CISSP #? If you get it, send me a DM on LinkedIn and next time we're in the same place, I'll buy lunch.YouTube video: https://youtube.com/live/5fDjArquTMcHave 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