Down the Security Rabbithole Podcast (DtSR)

Rafal (Wh1t3Rabbit) Los
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Aug 19, 2025 • 50min

DtSR Episode 667 - Market Consolidation is Screwing the CISO

Send the hosts a message - try it now!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 market consolidation. What is it good for? He's got some things to say, and he's not shy about it.YouTube: https://youtube.com/live/ROEA6z5Q-skSupport the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Aug 12, 2025 • 29min

DtSR Episode 665 - From Black Hat 2025 with Exhaustion

Send the hosts a message - try it now!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'all love him) and a bit of my take-away / rant from the week I spent out in the desert.  Enjoy, I hope you made it home safe and learned something. Good God it was hot.YouTube Video: ( standby, waiting on me to edit )Thanks again to my friends at Netskope!Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Aug 4, 2025 • 33min

DtSR Episode 664 - Everything You Wanted to Know About RaffCon

Send the hosts a message - try it now!** 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 and I break it down, give you a little history, and reminisce. As we got into Black Hat week, this is the perfect precursor to #RaffCon XVIII.YouTube video: https://youtube.com/live/jwArV_EwuZcSupport the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Jul 29, 2025 • 40min

DtSR Episode 663 - The CISO and CIO Relationship

Send the hosts a message - try it now!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 and evolve their roles together, for the benefit of everyone in the business? Larry Whiteside, Jr. ( Co-Founder and President at Confide) and Dennis McDonald ( Chief Information & Security Officer at Jack Henry ) lay down a conversation that's worth a repeated listen.YouTube video: https://youtube.com/live/g2F6BNSm2vkSupport the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Jul 22, 2025 • 45min

DtSR Episode 662 - Why Customer Success is Difference Maker

Send the hosts a message - try it now!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_K8Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Jul 15, 2025 • 40min

DtSR Episode 661 - Insights Into the Startup Mindset

Send the hosts a message - try it now!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 your own.YouTube video: https://youtube.com/live/qkAi6Nj8kIIShow Sponsor: ThreatLockerAllow what you need, block everything else... Including ransomware.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Jul 8, 2025 • 40min

DtSR Episode 660 - Sam Masiello

Send the hosts a message - try it now!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-4ZktBIUDEShow Sponsor: ThreatLockerAllow what you need, block everything else... Including ransomware.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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Jun 24, 2025 • 42min

DtSR Episode 659 - LinkedIn Cyber Influencers are Funny

Send the hosts a message - try it now!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/uZVfkge8bQESupport the show>>> Please consider clicking the link above to support the show!-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqLinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/X/Twitter: https://twitter.com/dtsr_podcast
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9 snips
Jun 17, 2025 • 48min

DtSR Episode 658 - What Does It Mean to Secure AI (Part 4)

Join Jeff Collins, Raja Mukerji, and John Dickson, experts in AI security, as they dive into the complexities of safeguarding artificial intelligence. Discover how traditional security practices adapt alongside new AI technologies and the ethical concerns surrounding data leakage. They explore the challenges of governance and the need for effective legislation, while also discussing innovative methods for analyzing AI behavior. The trio emphasizes proactive strategies and employee training to enhance security, advocating for a culture that prioritizes cybersecurity in AI development.
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9 snips
Jun 10, 2025 • 44min

DtSR Episode 657 - Cyber-Security Use-Cases for AI (Part 3)

Raja Mukerji, a cybersecurity expert, joins John Dickson and Jeff Collins to dive into the exciting world of AI in cybersecurity. They explore AI's unique capabilities that current tools can't match and debate whether AI will replace or augment human roles in security operations. With a focus on practical use-cases and limitations, they shed light on the balance needed between automation and human expertise. Intriguingly, they also discuss challenges for newcomers in the field and the innovative utilization of data beyond security.

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