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Down the Security Rabbithole Podcast (DtSR): Daily Summaries Delivered
by 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.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 6 days ago39 min
DtSR Episode 723 - Richard Bird Security is Built Wrong
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 BirdDescription 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 Cybers...
- 1 weeks ago48 min
DtSR Episode 722 - Vulnerability Math Ain't Mathing
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" HansenJeremiah GrossmanDescription The “vulnerability apocalypse” makes great headlines, but our day-to-day reality is stranger: more sc...
- 2 weeks ago1h 6m
DtSR Episode 721 - Finance Masterclass for Cyber (Part 2)
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 und...
- 3 weeks ago46 min
DtSR Episode 720 - Finance Masterclass for Cyber (Part 1)
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 the...
- Aug 18, 202637 min
DtSR Episode 719 - Budget Season for CISOs
Guests Jack KorzeniowskiKen FosterTL;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 ...
- Aug 11, 202635 min
DtSR Episode 718 - Black Hat Recap And The Rush To Rebrand Everything
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 ...
- Aug 4, 202640 min
DtSR Episode 717 - Your UI is Bullshit
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 t...
- Jul 28, 202632 min
DtSR Episode 716 - What if Context Replaced Alerts Entirely
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’r...
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About Down the Security Rabbithole Podcast (DtSR)
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.
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