Down the Security Rabbithole Podcast (DtSR)

TL;DR: This week's pod is a conversation about AI and "Open-Weight Models", and if you aren't intimately familiar with what these are this is an episode for you. Wes has a lot of insight, and this is a discussion rather than an info dump. Guest:  Wes Widner Description The most disruptive AI feature might not be a new chatbot trick; it might be the ability to download the model...

TL;DR:  Phile has been penetration testing for a long time. The difference now is that he's having a much easier time with it thanks to AI. It's an interesting world, and he's here to explain the offensive side of it. Guest: Phil Brass Description Zero-days are not a once-in-a-career event anymore. From B-Sides Atlanta, we sit down with veteran penetration tester Phil Brass to unpac...

TL;DR: Mehul joins Rafal live from BSides Atlanta to talk about how AI is changing how vulnerabilities are found and exploited at scale and cost. It's an interesting conversation about how much it costs to break into an organization's software stack. Video: https://youtu.be/kGajA9ipsp4 Guest Mehul Revankar Description A disclosed vulnerability no longer needs weeks of hacker effort. When...

TL;DR:  This episode is all about an essential skill few of us have mastered. How do you communicate  value ? What is it? And how do you make sure you're evaluating value in a way that makes sense to the person you're talking to? This is something that's essential to your career, your business, and your life, and Michael is a master of this art. Don't miss this one. Guest: Mich...

TL;DR:  This week's podcast features Rafal & Anton discussing the hype and hysteria that surrounds today's AI headlines. Which side is right, which side is propaganda, and what's real? Listen and find out. Guest Anton Chuvakin Description AI panic has officially gone mainstream, and we’re feeling it from every direction: “AI will kill us” on one end and “AI is useless hype” on t...

TL;DR:  This week's guest is Richard Bird, who has a new book coming out. He says, "Cybersecurity measures activity while its adversaries measure opportunity," and thirty years of spending has been priced against the wrong scoreboard. Great start, and you know it's going to get a little punchy. Guest: Richard Bird Description Cybersecurity spending has exploded for 30 years, an...

TL;DR: Robert "RSnake" Hansen & Jeremiah Grossman join the pod to talk about the "Vuln-pocalypse", or rather, the lack thereof. We do some math, discuss whether it's worth patching vulnerabilities attackers don't exploit, and discuss a potential alternative to the madness of vuln management and patching we're all living with today. Guests Robert "RSnake&...

TL;DR:  This pod is part 2 of a 2-part series in which Patrick shares his insights on the world of finance as it relates to cyber startups and financing. As promised, the tracksuit shows up, and it's an epic episode! Guest:  Patrick Dennis Description Private equity can feel like a plot twist: one day you are celebrating growth, the next day you are hearing new words like EBITDA, leverage, re...

TL;DR: This week's pod features a Masterclass on finance for Cyber folks, led by Patrick Dennis, where we ask all kinds of questions and go from idea to the pre-growth stage of a company. What's next? Check out part 2 coming next. Guest: Patrick Dennis Description A splashy funding announcement can feel like proof you’re winning, but it can also be the moment the clock gets louder. We si...

Guests Jack Korzeniowski Ken Foster TL;DR:  Budget season is upon us, and Rafal & James sit down with Ken Foster and Jack Korzeniowski to get some insights into how CISOs deal with budgets, separate truth from fiction, and get down into the dirty secrets. Description Budget season can feel like a slow-motion incident response: everyone has competing priorities, nobody wants surprise spend, and...

Guest : Dr. Chase "ZeroTrust" Cunningham TL;DR: AI Marketing slop took over Black Hat Las Vegas 2026, and Rafal sits down for a one-on-one with Chase Cunningham. Featuring their patented level of snark, real analysis, and hype detection, it's a fun conversation. Description Black Hat is supposed to be where the security industry shows its best work. This year, it also showed its big...

Guests: Michael Farnum , Sam Van Ryder TL;DR: Most cybersecurity dashboards don’t fail because they’re ugly. They fail because they don’t change what we do next. Description In Episode 717, Rafal sits down with Michael Farnum (Cybersec Community) and Sam (Dragos, a long-time OT and industrial cybersecurity practitioner) to talk about the uncomfortable truth behind security UI/UX: much of what show...

Guests: Jason Vest & Josh Neil TL;DR: Alert fatigue is still a problem; detection isn't generationally better - but we have all this AI. So what gives? Description Alert fatigue is not just a workload problem; it is a product design problem. We dig into a provocative claim sparked by a LinkedIn post: today’s “AI SOC triage” can be a band-aid if it only cleans up alerts after the fact inst...

TL;DR:  David Kennedy & Larry Whiteside, Jr. join the podcast to talk about how 'alerts' are a terrible measure of work in the SOC, and what we're doing about it. We discuss the analyst experience, why it's so difficult and leads to burning our best staff out, and also David introduces his latest: NightBeacon CMD. You need to hear this. I'm starting to edit my own vide...

TL;DR: This week's pod is the conclusion to the 2-part series on AI SOC with Anton Chuvakin, Daniel Miessler, Rock Lambros, Erik Bloch, and Raja Mukerji. We talk about the rational application of AI to cybersecurity and what the future holds for the various options. You won't want to miss this one. Youtube Video: https://youtu.be/5YIpZuQLTMg Have something to say? Let's hear it. Supp...

TL;DR: Join Raja Mukerji , Anton Chuvakin , Daniel Miessler , Rock Lambros , and Erik Bloch for a banger of an episode (part 1 of 2) where we debate the potential of AI and the current state of delivery for SOC and security applications. This episode was made possible by a group of people with much better things to do than record a podcast who donated their time. Please join me in thanking them fo...

TL;DR: Seth Summersett of Embed Security joins the podcast to talk about the snake oil that's coming from the AI SOC sellers. There's such a significant gap between what you're being sold and what's real. Seth and the gang talk about what's real, what you should expect, and where the line of bullsh** is. YouTube video: https://youtube.com/live/Z8R19cjTjwA? Have something t...

TL;DR:  This week's pod features Tim Chase , a field CISO and, by background, a practitioner. We talk about "prioritization", a topic that's boring but incredibly necessary, as I am confident nobody out here has this solved yet! YouTube Video: https://youtube.com/live/099rUu0pV0g Have something to say? Let's hear it. Support the show >>> Please consider clicking th...

TL;DR: This week's podcast features Adam Ely - innovator, leader, and founder. Adam's led some of the world's largest security orgs, and started a tiny start-up. He's got knowledge and wisdom to share, so take it in. YouTube video: https://youtube.com/live/PVTDaiiwlMs Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above...

TL;DR: Phillip Wylie joins Rafal live from Zero Trust World 2026 in Orlando, FL, to talk about Operational Technologies (OT) in the context of Zero Trust. As the Joker once said, "Hubba Hubba, who do you trust?" YouTube: https://youtu.be/N5sI85IwxIQ Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-...

TL;DR:  This week's pod features Karim Hijazi, Adam Meyers, and Will Gragido on AI and the potential  advantages for adversaries . It's a fascinating discussion with in-depth analysis, commentary, and relatable stories that will give you the insights you can't get anywhere else. Buckle in, this one's an hour but completely worth it. YouTube Video: https://www.youtube.com/live/w...

TL;DR:  Today's pod features Will Gragido , a multi-time returning guest with deep expertise in cyber intelligence, threat actors, and related activity. Will shares his expertise with us on how AI will impact the gathering, analysis, dissemination, and utilization of adversary and threat intelligence. YouTube Video: https://youtube.com/live/l7mrBPRTokQ Have something to say? Let's hear it...

TL;DR:  How are organizations like the Motley Fool handling AppSec right now ? How are companies building sustainable, measurable, and resilient software security programs, even as AI looms overhead? Catch Paolo del Mundo , Director of Application Security at the Motley Fool , and hear his insights on how he and his team make it work. YouTube video: https://youtube.com/live/s6z-OytApF0 Have someth...

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/q15xAwcPur8 Have something to say? Let's hear it. Support the show >>> P...

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/q15xAwcPur8 Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show...