Down the Security Rabbithole Podcast (DtSR)

762 Episodes

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DtSR Episode 725 - The Importance of Communicating Value

2026-09-2944:45

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: Michael SantarcangeloDescription Most cybersecurity pros know the feeling: you ship real work, you reduce real ri...

DtSR Episode 724 - Unpacking the AI Hysteria

2026-09-2238:10

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 ChuvakinDescription 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...

DtSR Episode 723 - Richard Bird Security is Built Wrong

2026-09-1539:15

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...

DtSR Episode 722 - Vulnerability Math Ain't Mathing

2026-09-0948:49

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...

DtSR Episode 721 - Finance Masterclass for Cyber (Part 2)

2026-09-0101:06:58

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...

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Down the Security Rabbithole Podcast (DtSR)