Down the Security Rabbithole Podcast (DtSR)

TL;DR: Xavier Ashe was there when that first DDoS attack by MafiaBoy went down. He's got stories, and we're going to tell them. Recorded live at BSides Atlanta in 2026.

Guest

Description: A DDoS attack used to be something you could “just block” once you saw the source. Then defenders learned the hard way that thousands of small senders can knock over a giant, and the playbook changed for good. From the stage at B-Sides Atlanta at Georgia Tech, we sit down with security veteran Xavier Asht for...

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: 

Description

The most disruptive AI feature might not be a new chatbot trick; it might be the ability to download the model and run it yourself. Recorded live at B-Sides Atlanta 2026, we sit down with Wes Widner, senior principal e...

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 unpack what happens when large language models make vulnerability research dramatically faster and cheaper, not just for defenders, but for attackers too.<...

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

Description

A disclosed vulnerability no longer needs weeks of hacker effort. When exploitation becomes an automated, agentic workflow measured in minutes and dollars of compute, the way we rank risk, plan patching...

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: 

Description

Most cybersecurity pros know the feeling: you ship real work, you reduce real risk, a...

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

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 the other. Rafal brings in Anton Chuvakin to filter the noise and ask a simpler question: what’s actually true when you strip away the soc...

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:

Description

Cybersecurity spending has exploded for 30 years, and the scoreboard still looks brutal. We sit down with Richard to talk about his new book, “Built Wrong: Why Cybersecurity is Failing and How We Can Rebuild It...

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

Description

The “vulnerability apocalypse” makes great headlines, but our day-to-day reality is stranger: more scanners, more CVEs, more urgency, and still the same breaches. We sit down with Jeremiah Grossman and Robe...

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, recap, and “value creation plan,” and everything from headcount to product scope is suddenly under a microscope. We sit do...

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 sit down with returning guest Patrick Dennis, a multi-time [cybersecurity] CEO and operator who “swims in these waters,” to tra...

Guests

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 security still has to defend the enterprise. We sit down with experienced security leaders to talk candidly about how cybersecurity budgeting really works when you’re...

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 biggest temptation: slap “AI” on everything, crank the volume, and sort out the truth later.

We break down what we saw on the floo...

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 shows up in the GUI is pure noise. We dig into the split between “pretty but useless” interfaces and tools...

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 instead of improving threat detection where it starts, in raw telemetry and early signal extraction.

We...

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 videos, so hopefully you like the new format.

YouTube Video: https://youtu.be/aMTFaXwRl_A

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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

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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 for their generous contributions.

YouTube video: ...coming soon, blame Anton

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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?

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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

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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

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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

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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/w7nBe_uS8G4

Energy-Based Model company (that Karim referenced): https://logicalintelligence.com/

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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

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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

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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

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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

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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/RxY0Zj2UtLw

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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/0umF7Bv3ra4

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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:

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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/bUnz763Iq90

Have so...

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)

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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_Q

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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/_gpV4XilToc

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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/aOP6IT8OiDI

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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/bhtvOSv48Jc

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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/Adpyja9KIkU

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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/t48sX54QCwI

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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/qngve0dmd7M

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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-signal

YouTube video: https://youtube.com/live/6ZCPNXR_5u0

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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/tJcjtgn759g

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