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Down the Security Rabbithole Podcast (DtSR)

Rafal (Wh1t3Rabbit) Los
Cybersecurity
Artificial Intelligence
Ransomware
Cyber Security
Risk Management
Vulnerability Management
Cloud Security
CISO
Zero Trust
Machine Learning
Identity Security
Work-Life Balance
Incident Response
Cyber Insurance
Application Security
Access Control
Remote Work
Crisis Management
Burnout
Data Breaches

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... more

PublishesWeeklyEpisodes748Founded15 years ago
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Artwork for Down the Security Rabbithole Podcast

Latest Episodes

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:/... more

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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: youtube.c... more

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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: youtu.be/N5sI85IwxIQ... more

YouTube

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 yo... more

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Key Facts

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Recent Guests

Phillip Wylie
Offensive security professional, podcaster, and author
Independent security professional
Episode: DtSR Episode 709 - Zero Trusting OT
Adam Meyers
Head of CrowdStrike's Counter Adversary Operations
CrowdStrike
Episode: DtSR Episode 708 - Does AI Give Threat Actors an Advantage
Will Gragido
Co-founder and CEO of Salient Cyber
Salient Cyber
Episode: DtSR Episode 708 - Does AI Give Threat Actors an Advantage
Paolo del Mundo
Leader of the Application Security Function at The Motley Fool
The Motley Fool
Episode: DtSR Episode 706 - Practical AppSec for the AI Vulnpocalypse
Howard Holton
CEO of GigaOm, analyst firm
GigaOm
Episode: DtSR Episode 704 - Market Saturation, Innovation and Procurement
Yonesy Nunez
CISO at Surf AI; former multiple CISO roles in Financial Services/Utilities
Surf AI
Episode: DtSR Episode 702 - Trust Issues with Trusted Advisors
Joshua Jones
CEO and co-founder of Crush Security
Crush Security
Episode: DtSR Episode 702 - Trust Issues with Trusted Advisors
Chris Roche
Board of Advisors for Crush; former CISO leadership roles
Crush Security (Advisory)
Episode: DtSR Episode 702 - Trust Issues with Trusted Advisors
Adrian Sanabria
Founder and principal researcher at the Defenders Initiative
Defenders Initiative
Episode: DtSR Episode 701 - Adrian Sanabria AI Cant Replace Jobs

Hosts

Rafal Los
Host of Down the Security Rabbithole Podcast
James Jardine
Co-host of DtSR; engages guests in critical discussion
Jim Tiller
Co-host/Guest host; contributes expertise and discussion leadership

Reviews

4.4 out of 5 stars from 165 ratings
  • Real infosec knowledge

    Raf does an excellent job of providing insight and advice around the difficult task of balancing security and business sensitivity. One of my favorites- highly recommend.

    Apple Podcasts
    5
    raxis
    United States4 years ago
  • Raf is a podcasting legend in InfoSec! Always great content on his show!

    Podchaser
    5
    Tom Eston
    4 years ago
  • Excellent Podcast!

    The host, Rafal, is excellent at driving the conversation and bringing interesting and relevant topics to his listeners. I absolutely love the topics they cover!

    Apple Podcasts
    5
    treguly
    Canada4 years ago
  • DTSR - Don’t Listen to the Podcast!!

    If you want to remain an ignoramus don’t listen to the podcast.

    As a relative N00b to the world of applied information security I needed to get up to speed fast. I had started a Masters degree in InfoSec. But the topic, as I quickly discovered, is both far reaching and fast moving. Although I was reading papers and learning as much as I could I was missing the real world application.

    The DTSR podcast gave me the insight into conversations above the level of my current role and rounds out my lea... more

    Apple Podcasts
    5
    SteveHeap
    United Kingdom6 years ago
  • Enjoyed coverage on Cybersecurity Canon project and interview.

    Podcast Addict
    5
    Gurulee
    6 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Guests are typically industry veterans offering real-world insights, not hype.
Production quality and hosting chemistry are frequently highlighted as standout features.
Listeners praise high-signal, practical security discussions that tie tech to business outcomes.
The show is lauded for balanced perspectives on AI, vendor dynamics, and risk governance.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#193
United States/News/Tech News
Apple Podcasts
#173
United Kingdom/News/Tech News
Apple Podcasts
#199
Canada/News/Tech News
Apple Podcasts
#160
Germany/News/Tech News
Apple Podcasts
#168
France/News/Tech News
Apple Podcasts
#228
Australia/News/Tech News

Talking Points

Recent interactions between the hosts and their guests.

DtSR Episode 706 - Practical AppSec for the AI Vulnpocalypse
Q: What's the role of your team in AppSec? Are you a gatekeeper, an auditor, or a governance body?
Paolo explains that his team positions itself as risk consultants to developers, assessing security controls and risks while using compliance language to frame decisions, with the ultimate goal of enabling secure delivery rather than simply blocking changes.
DtSR Episode 701 - Adrian Sanabria AI Cant Replace Jobs
Q: And we should start talking about it. You wrote something super interesting. Give us a synopsis.
Adrian explains the core idea that AI cant replace jobs because jobs are aggregates of many tasks, and AI tends to perform well on simple, well-defined tasks but struggles with nuanced human judgment and experience-based decisions. He emphasizes the distinction between tasks and jobs and provides examples from marketing and security workflows to illustrate where automation makes sense and where it does not.
DtSR Episode 702 - Trust Issues with Trusted Advisors
Q: How should buyers approach vendor evaluation in this crowded landscape?
Start with what you actually need, map it to a few differentiating features, and use objective data to compare those differentiators across vendors, rather than chasing every new feature or marketing claim. Build a process that looks at overlap, total cost of ownership, and real-world applicability to your environment.
DtSR Episode 702 - Trust Issues with Trusted Advisors
Q: What is the core problem you're trying to solve for buyers and CISOs?
The core problem is the mismatch between perceived value from vendors and the actual needs of buyers, aggravated by fragmentation, pay-to-play dynamics, and unreliable guidance. The goal is to provide independent, data-driven analysis that helps buyers understand what really matters and how to optimize their security stack.
DtSR Episode 696 - Zero Trust CyberSecurity Shenanigans
Q: What's new since you last talked?
The platform continues to grow with features like Defense Against Configurations, Web Control, and Patch Management, with a broader strategy around deny-by-default and permit-by-exception.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
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Frequently Asked Questions About Down the Security Rabbithole Podcast

What is Down the Security Rabbithole Podcast about and what kind of topics does it cover?

This show centers cybersecurity leadership, market dynamics, AI's impact on defense and threat intelligence, and practical, business-aligned security practices. Episodes routinely explore how AI accelerates human analysis, the troubles and opportunities of AI-enabled tooling, and how security teams partner with developers, executives, and vendors to deliver risk-aware, impact-focused outcomes. Guests range from CISOs and security leaders to researchers and analysts, who share real-world perspectives on governance, procurement, and implementing scalable security programs. A notable pattern is balancing tech hype with actionable, human-centered security—discussing patching, risk communication, and how to build trustworthy, resilient security ... more

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Which podcasts are similar to Down the Security Rabbithole Podcast?

These podcasts share a similar audience with Down the Security Rabbithole Podcast:

1. SANS Internet Stormcenter Daily Cyber Security Podcast (Stormcast)
2. Defense in Depth
3. CyberWire Daily
4. Risky Business
5. Cybersecurity Headlines

How many episodes of Down the Security Rabbithole Podcast are there?

Down the Security Rabbithole Podcast launched 15 years ago and published 748 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Down the Security Rabbithole Podcast?

Recent guests on Down the Security Rabbithole Podcast include:

1. Phillip Wylie
2. Adam Meyers
3. Will Gragido
4. Paolo del Mundo
5. Howard Holton
6. Yonesy Nunez
7. Joshua Jones
8. Chris Roche

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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