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.
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/
Episodes
704 episodes
DtSR Episode 667 - Market Consolidation is Screwing the CISO
TL;DR: This week's guest is Dr Sam Liles - who's been CISO'ing since most of us have been in the industry. Sam gets it, and he has some perspective on what's going on with all this marke...
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Season 15
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Episode 667
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49:59
DtSR Episode 665 - From Black Hat 2025 with Exhaustion
TL;DR: This week's show is a testament to surviving a week of Hacker Summer Camp out in Las Vegas. I have an interview with Ray Canzanese, Jr. (again, because y...
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Season 15
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Episode 665
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29:12
DtSR Episode 664 - Everything You Wanted to Know About RaffCon
** Early release, due to Black Hat Conference and RaffCon XVIII.TL;DR: This episode is all about #RaffCon. Ever wanted to know what the heck it is? Well, Raffael Marty...
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Season 15
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Episode 664
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32:31
DtSR Episode 663 - The CISO and CIO Relationship
TL;DR: This is one of the most important episodes we've done on this podcast. The CISO and CIO have a complicated, dynamic, and often ugly relationship - but what should it be like? How can the two work together an...
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Season 15
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Episode 663
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40:14
DtSR Episode 662 - Why Customer Success is Difference Maker
TL;DR: This week's conversation is all about the Customer Success team featuring Nick Puetz and Steve Dakhe. Th...
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Season 15
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Episode 662
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44:55
DtSR Episode 661 - Insights Into the Startup Mindset
TL;DR: This week we took a sit-down with serial entrepreneur, Will Gragido. Will has been a part of several innovative start-ups, and is now onto his next one. He's a product innova...
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Season 15
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Episode 661
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40:04
DtSR Episode 660 - Sam Masiello
TL;DR: Did you miss us? Yes, we're back with Sam Masiello and we're talking about whatever is on his mind. Well ...there's geopolitics and Iranian hackers and frankly we need to t...
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Season 15
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Episode 660
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39:38
DtSR Episode 659 - LinkedIn Cyber Influencers are Funny
TL;DR: This week's episode came from my (Rafal) brain. I've been reading far too much LinkedIn, and the "influencer" postings have been making me crazy. So, here we are. We talk through some of these posts, many of which are A...
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Season 15
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Episode 659
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42:15
DtSR Episode 658 - What Does It Mean to Secure AI (Part 4)
TL;DR: On this episode, part 4 of our AI series, we are once again joined by Raja Mukerji, Jeff Collins, and
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Season 15
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Episode 658
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47:56
DtSR Episode 657 - Cyber-Security Use-Cases for AI (Part 3)
TL;DR: This week I bring John Dickson back to join Jeff Collins and
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Season 15
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Episode 657
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43:31
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 di...
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Season 15
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Episode 656
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44:20
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 dependenc...
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Season 15
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Episode 655
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51:15
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 ...
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Season 15
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Episode 654
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43:12
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 end...
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Season 15
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Episode 653
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18:29
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 ...
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Season 15
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Episode 652
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29:33
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 stra...
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Season 15
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Episode 651
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45:34
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" (
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Season 15
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Episode 650
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41:38
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...
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Season 15
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Episode 649
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47:02
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...
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Season 15
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Episode 648
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43:52
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 s...
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Season 15
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Episode 647
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41:10
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...
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Season 15
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Episode 646
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35:33
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 ca...
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Season 15
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Episode 645
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23:43
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 o...
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Season 15
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Episode 644
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43:52