Down the Security Rabbithole Podcast (DtSR)

TL;DR:  This week's conversation is all about the Customer Success team featuring Nick Puetz and Steve Dakhe . These guys have significant seat time building, operating, and perfecting the CSM role - and we're here to talk about it. What is a CSM? Why do they exist? And what is their role in customer engagement? Listen in, find out! YouTube: https://youtube.com/live/lCen-1Vt_K8 Have some...

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 innovator with a pragmatic sense of what customers need, and he's here to give you the run-down of what drives him, what got him here, and things you should think about if you're thinking of setting off on yo...

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 talk about what it means for your security program. Thanks for joining us, Sam! YouTube Video: https://youtube.com/live/H-4ZktBIUDE Have something to say? Let's hear it. Show Sponsor: ThreatLocker Allow...

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 AI generated I think, and have a little fun with it. Call it...therapy. YouTube Video: https://youtube.com/live/uZVfkge8bQE Have something to say? Let&#3...

TL;DR:  On this episode, part 4 of our AI series, we are once again joined by Raja Mukerji , Jeff Collins , and John Dickson to discuss what it means to think about security for AI. Is it something completely different? Is it something same-'ol? Or - is it a bit of both. And what aren't we thinking about when it comes to securing AI? YouTube video: https://youtube.com/live/vUJIOrX0kHc Ha...

TL;DR: This week I bring John Dickson back to join Jeff Collins and Raja Mukerji as we talk through the following: What can AI do, for cyber security, that we can't do with current tools? What is the model for incorporating AI into cybersecurity - are we replacing people? augmenting people? both? neither? Where is AI the strongest in these use-cases today, and where is the promise for 12 - 36...

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 comin...

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 ....

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 visua...

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 su...

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/LSd...

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_Sb...

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...

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 pr...

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 R...

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. Yo...

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&...

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 Trus...

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...

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...

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 -...

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 >&gt...

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 conside...

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. S...

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 caree...