Down the Security Rabbithole Podcast (DtSR)

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.

On Twitter/X: https://twitter.com/@DtSR_Podcast
On YouTube: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq
On LinkedIn: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/

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Episodes754

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Jun 3, 2025 · 44 min
DtSR Episode 656 - Deeper Down the AI Rabbithole Part 2
TL;DR: This week John Dickson returns to go deeper down the AI rabbit hole with special guest Erik Bloch as we dive into a more technical explanation of AI, how this innovation differs from other similar concepts, previous tech innovations, and some of the commercial vs consumer use-cases where AI is best suited. It's a deeper discussion, and we will for sure have a part 3, and likely 4 coming soon. YouTube video: https://youtube.com/live/QXi6ed2NKhc Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
May 27, 2025 · 51 min
DtSR Episode 655 - John Dickson Down the AI Rabbithole Part 1
TL;DR: So - Artificial Intelligence (AI)...incomprehensible good, or catastrophic evil? Both? And what does that depend on? This episode is the start of a series wherein we explore the potential good or bad of AI, what the dependencies are. and what kinds of branches of discussion there could be. Join us as we discuss a generational topic, with some of our best guests starting with John Dickson. Required listening: Episode 654 w/Sounil Yu ( https://dtsr.buzzsprout.com/2153215/episodes/17193885-dtsr-episode-654-can-we-teach-machines-discretion ) Bonus, since none of you read this ... what's John's CISSP #? If you get it, send me a DM on LinkedIn and next time we're in the same place, I'll buy lunch. YouTube video: https://youtube.com/live/5fDjArquTMc Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
May 20, 2025 · 43 min
DtSR Episode 654 - Can We Teach Machines Discretion?
TL;DR: This week's episode asks the question - is it possible to give AI "discretion" (which feels like a uniquely human concept)? And if so - what would that look like, and how can this help a society that's hurling headlong into an AI future from destroying secrecy as we know it? Sounil Yu from Knostic joins Rafal & James to think through the problem - complete with visuals! If that sounds a little dramatic, you'll enjoy the episode, because this problem is very real and those outside security have no idea they're creating it. Cyber Defense Matrix: https://cyberdefensematrix.com/ YouTube Video: https://youtube.com/live/ob502v_NqOo Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
May 13, 2025 · 18 min
DtSR Episode 653 - Rich Latayan Live and In Person
TL;DR: On this "live on the scene" episode from Zero Trust World 2025 sponsored by Threat Locker - I have the distinct pleasure to speak with Rich Latayan about his career leading big-company security programs as CISO and his current endeavor. YouTube: <coming soon> Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
May 6, 2025 · 29 min
DtSR Episode 652 - RSA Conf 2025 Wrap with Ray Canzanese, Jr.
TL;DR: As per the usual, this year's RSA Conference 2025 wrap-up is with my friend Ray Canzanese, Jr. We sit in the beautiful sunshine atop the Moscone Center (gardens) and have an interesting, conversation about a number of interesting topics not the least of which is the puppies and baby goats at this year's event (well played, vendors, well played). YouTube Video: https://youtu.be/LSdEMlKRZmw Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Apr 29, 2025 · 45 min
DtSR Episode 651 - Meaningfully Addressing the CISO Vendor Relationship
TL;DR: Sometimes LinkedIn gives us an opportunity to record something meaningful - and in this episode we find a conversation with Ross Hosman's perspective on how to address the strained relationship between buyer and seller, CISO and vendor - in a meaningful way that you'll hopefully benefit from. Sales people, take notes. CISOs ... you too. YouTube video: https://youtube.com/live/e_SbcB2ZsD8 Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Apr 22, 2025 · 41 min
DtSR Episode 650 - Executing a Human Focused Security Approach
TL;DR: This episode is a follow-up on two episodes, building up to this conversation. On episode 629 Hed Kovetz introduced us to "Identity Security" (https://dtsr.buzzsprout.com/2153215/episodes/16174464-dtsr-episode-629-what-the-hell-is-identity-security) and then on episode 646 Ward Pyles started the conversation about how security tools really aren't set up to protect from the identity perspective (https://dtsr.buzzsprout.com/2153215/episodes/16854549-dtsr-episode-646-ward-pyles-on-human-centric-security-for-real). Well - now we invited them both onto the show to talk it through and solve the problem Ward identified with the tech Hed spoke of. The result was better than we expected. YouTube video: https://youtube.com/live/N7cyIOdChtw Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Apr 15, 2025 · 47 min
DtSR Episode 649 - Casey Ellis Other People's Software Bugs
TL;DR: This week's guest is BugCrowd's founder Casey Ellis. Casey's a pioneer in the security space and has some tremendous insights on how he started his business and what the future holds. Casey explains why it's important to think like a criminal, and why the 'locksmith' version of a hacker (versus 'burglar') is so important to today's security programs. YouTube video: https://youtube.com/live/8BLGfUqbOKQ Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Apr 8, 2025 · 43 min
DtSR Episode 648 - CyberSecurity Market Forces
TL;DR: This week we're joined by the one and only Mike Privette - to talk about the market forces pushing and pulling cyber security's momentum. Whether you're into startups a la VC funding, or looking to refurbish companies a la Private Equity - this conversation is an analysis of the market from someone who knows a thing or two about the whole game. Oh yeah, and Mike writes this Return on Security newsletter you need to subscribe to. YouTube video: https://youtube.com/live/wq0KlteA1bU Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Apr 1, 2025 · 41 min
DtSR Episode 647 - Shiran Bareli AI as More Than Next Gen DLP
TL;DR: If you're deciding whether to listen to this episode - let me help you - YES. This episode is about the application of AI to one of the most difficult problems facing security teams - what and where is my most sensitive information? Face it, you have no idea - and maybe, just maybe, AI is part of the answer. Shiran Bareli joins Jim and Rafal to talk it over, and it's a doozy. YouTube Video: https://youtube.com/live/nhn6Q75syjk Don't forget to check out the after-show segment, only on our YouTube page! Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Mar 25, 2025 · 35 min
DtSR Episode 646 - Ward Pyles on Human Centric Security for Real
TL;DR: This week Ward Pyles joins Jim Tiller and myself to talk about a relatively unremarkable topic - people-centric security. We've talked about it a bunch but it's not until this episode that something finally clicked in my brain. When Ward talks about the data that security needs - see if you can pick it up too. Also - I'm trying some new bonus content - the "After Show" which is a 2-5 minute post-show bit where we post what's said after the recording (usually) stops. I hope you enjoy it - check that out exclusively on our YouTube channel. YouTube video: https://youtube.com/live/LWzA2czvocQ Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Mar 18, 2025 · 23 min
DtSR Episode 645 - Zero Trust Applied in the Real World
TL;DR: This week's episode is a sit-down in person at Zero Trust World 2025 (sponsored by ThreatLocker) with Ryan Benner. Ryan's the caretaker of "anything that powers up", as he puts it, which means this small organization's security is also his responsibility. So how do you do it with next to no staff, and on a small budget? And how do you even begin to "Zero Trust" your network? Listen in. YouTube Video: https://youtu.be/JUMcWFNsVaA Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Mar 11, 2025 · 43 min
DtSR Episode 644 - Inside the Minds of Great Product Managers
TL;DR: This week's episode shifts the focus from leadership in the enterprise, to leadership in the vendor space. Building security products that innovate, inspire, and meet market and customer demand is far from trivial. Meet two of the best in the business - Arash Marzban and Bryan Lares - and hear what makes the job exciting, and how they make it great. YouTube video: https://youtube.com/live/wA9-vgusyI0 Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Mar 4, 2025 · 39 min
DtSR Episode 643 - A CISO's Guide to the First 90 Days
TL;DR: This week's podcast features the wisdom and wit of Merlin Namuth - currently serving as the CISO for the city & county of Denver. Merlin provides insights into how he views the first 90 days of a CISO's role with a new organization, frameworks and processes he goes through to get his bearings and start a successful residency. YouTube Video: https://youtube.com/live/8y7bsKlBBXE?feature=share Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Feb 25, 2025 · 23 min
DtSR Episode 642 - Chase Cunningham An Epic Zero Trust Keynote
TL;DR: This episode was recorded live from Zero Trust World 2025 in Orlando, FL sponsored by ThreatLocker. Chase Cunningham joins after finishing an epic keynote where he eviscerates security dogma and the repeated stupidity of the Cyber sector. Chase & Rafal discuss Zero Trust, implications, implementation, and value. YouTube: Big thanks to ThreatLocker for hosting Zero Trust World 2025 - can't wait to get back next year! Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Feb 18, 2025 · 38 min
DtSR Episode 641 - Kevin Fielder Security Principles and Guard Rails
TL;DR: On this episodes we welcome Kevin Fielder, CISO @ NatWest Boxed & Mettle, Advisor, investor, Coach, and speaker to talk about building guard rails and principles to minimize security's negative impact on business and technology while raising the bar for attackers. YouTube Video: https://youtube.com/live/xYPdHkUW0TQ Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Feb 11, 2025 · 39 min
DtSR Episode 640 - A Practitioner View of Security Automation
TL;DR: This week is a real treat! Eva Georgieva - a seasoned cybersecurity automation engineer - joins me, James, and Jim to talk about automation in cyber. We talk about challenges, what to automate first, good versus bad automation, and even get a little practical. YouTube: https://youtube.com/live/lA20Mgl3AxE Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Feb 4, 2025 · 49 min
DtSR Episode 639 - Richard Bird Famous With 12 People
TL;DR: This week's episode features a long-time-coming discussion with Richard Bird discussing his book "Famous with 12 people", and the "influencer culture" in cybersecurity. It's an interesting discussion on how our industry works, and who makes it really turn. YouTube: https://youtube.com/live/hk42GbjzDZQ?feature=share Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Jan 28, 2025 · 35 min
DtSR Episode 638 - Matt Shufeldt Cyber Security's Specialist Problem
TL;DR: This week's episode is all about a growing issue in CyberSecurity (and I'm sure it's there in other disciplines as well) - "specialization" or more to the point "over-specialization". Why is it a problem? Matt Shufeldt, a returning guest and friend of the pod, joins us to talk about it and suggests some ways we can avoid the giant iceberg we're careening into. YouTube: https://youtube.com/live/q_3uYcdYaw4 Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast
Jan 21, 2025 · 45 min
DtSR Episode 637 - Amanda Berlin Build SMB Tools That Don’t Suck
TL;DR: On this episode Amanda Berlin, Senior Product manager at Blumira, joins Jim and Rafal to talk about her career, the second edition of her book, and building products for SMBs that "don't suck". The unfortunate fact is that there aren't a lot of products designed for the unique challenges of companies that can't afford an army of security analysts, or consultants. YouTube Video: https://youtube.com/live/rvXqjBU5M4k Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast