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PODCAST

Down the Security Rabbithole Podcast (DtSR)

Rafal (Wh1t3Rabbit) Los

This is Cybersecurity"s premier podcast. Running strong since 2011 Rafal Los, James Jardine, and Jim Tiller bring a no-nonsense, non-commercial approach to our profession. DtSR brings interviews and discussion with people you want to meet, and stories you have to hear. So whether you"re just starting out, or are decades deep into your career, you"ll always learn something on this show.On Twitter/X: https://twitter.com/@DtSR_PodcastOn YouTube:

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All Episodes

48:25

DtSR Episode 677 - Is Cyber Insurance the Answer or A...

Down the Security Rabbithole Podcast (DtSR) ·

2025/10/28

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/GiuheFiFO78 Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-...

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43:58

DtSR Episode 676 - Privacy and Healthcare Data at...

Down the Security Rabbithole Podcast (DtSR) ·

2025/10/21

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/l...

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46:16

DtSR Episode 675 - Trey Ford on the Mind of CISOs

Down the Security Rabbithole Podcast (DtSR) ·

2025/10/14

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=share Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=...

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44:56

DtSR Episode 674 - 3rd Party Risk is a Mess

Down the Security Rabbithole Podcast (DtSR) ·

2025/10/07

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/Le23nkaybfE Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-...

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43:13

DtSR Episode 673 - Crash Out to Cash Out

Down the Security Rabbithole Podcast (DtSR) ·

2025/09/30

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? Links https://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-...

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39:01

DtSR Episode 672 - DFARS CMMC Update Insights

Down the Security Rabbithole Podcast (DtSR) ·

2025/09/23

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/0cl1S4f3g8E Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=...

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40:58

DtSR Episode 671 - It's The End of the Internet As We...

Down the Security Rabbithole Podcast (DtSR) ·

2025/09/16

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/tUJgdrh3ws8 Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-...

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40:57

DtSR Episode 670 - Ethics Equity and Rock Star CISOs

Down the Security Rabbithole Podcast (DtSR) ·

2025/09/09

Send the hosts a message - try it now! 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-YSct YouTube video: https://youtube.com/live/N1mD...

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43:26

DtSR Episode 669 - ADR Enters the SOC Chat

Down the Security Rabbithole Podcast (DtSR) ·

2025/09/02

Send the hosts a message - try it now! 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/69xeGDoDYbU Links Contrast's latest threat report (referenced in the show)An in-depth ADR Explainer (helpful!)Run-Time Security Explai...

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38:53

DtSR Episode 668 - Actionable Crowd Sourced Defenses

Down the Security Rabbithole Podcast (DtSR) ·

2025/08/26

Send the hosts a message - try it now! 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/7Xc99bXCfwQ Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= ...

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49:59

DtSR Episode 667 - Market Consolidation is Screwing...

Down the Security Rabbithole Podcast (DtSR) ·

2025/08/19

Send the hosts a message - try it now! 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-sk Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-...

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29:12

DtSR Episode 665 - From Black Hat 2025 with Exhaustion

Down the Security Rabbithole Podcast (DtSR) ·

2025/08/12

Send the hosts a message - try it now! 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! Support the show >>&g...

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32:31

DtSR Episode 664 - Everything You Wanted to Know...

Down the Security Rabbithole Podcast (DtSR) ·

2025/08/04

Send the hosts a message - try it now! ** 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_EwuZc Support the show >>> Please consider clicking the link above to support the sh...

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40:14

DtSR Episode 663 - The CISO and CIO Relationship

Down the Security Rabbithole Podcast (DtSR) ·

2025/07/29

Send the hosts a message - try it now! 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 ...

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45:32

DtSR Episode 662 - Why Customer Success is Difference...

Down the Security Rabbithole Podcast (DtSR) ·

2025/07/22

Send the hosts a message - try it now! 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_K8 Digital Disruption with Geoff Nielson Discover how technology is reshaping...

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40:41

DtSR Episode 661 - Insights Into the Startup Mindset

Down the Security Rabbithole Podcast (DtSR) ·

2025/07/15

Send the hosts a message - try it now! 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/qkAi6Nj8kII Digital Di...

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40:50

DtSR Episode 660 - Sam Masiello

Down the Security Rabbithole Podcast (DtSR) ·

2025/07/08

Send the hosts a message - try it now! 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-4ZktBIUDE Digital Disruption with Geoff Nielson Discover how technology is reshaping our lives and livelihoods.Listen on: Apple Podcasts Spotify ...

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42:52

DtSR Episode 659 - LinkedIn Cyber Influencers are Funny

Down the Security Rabbithole Podcast (DtSR) ·

2025/06/24

Send the hosts a message - try it now! 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/uZVfkge8bQE Digital Disruption with Geoff Nielson Discover how technology is reshaping our lives and livelihoo...

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48:33

DtSR Episode 658 - What Does It Mean to Secure AI...

Down the Security Rabbithole Podcast (DtSR) ·

2025/06/17

Send the hosts a message - try it now! 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/vUJIOrX0kHc Digital Disruption with Geoff Nielson Discover how technology is res...

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44:08

DtSR Episode 657 - Cyber-Security Use-Cases for AI...

Down the Security Rabbithole Podcast (DtSR) ·

2025/06/10

Send the hosts a message - try it now! 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...

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