

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_PodcastOn YouTube: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHqOn LinkedIn: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/
Episodes
Mentioned books

Jul 29, 2025 • 41min
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/g2F6BNSm2vkDigital Disruption with Geoff Nielson Discover how technology is reshaping our lives and livelihoods.Listen on: Apple Podcasts SpotifySupport 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

Jul 22, 2025 • 46min
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_K8Digital Disruption with Geoff Nielson Discover how technology is reshaping our lives and livelihoods.Listen on: Apple Podcasts SpotifySupport 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

Jul 15, 2025 • 41min
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/qkAi6Nj8kIIDigital Disruption with Geoff Nielson Discover how technology is reshaping our lives and livelihoods.Listen on: Apple Podcasts SpotifyShow 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

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-4ZktBIUDEDigital Disruption with Geoff Nielson Discover how technology is reshaping our lives and livelihoods.Listen on: Apple Podcasts SpotifyShow 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

Jun 24, 2025 • 43min
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/uZVfkge8bQEDigital Disruption with Geoff Nielson Discover how technology is reshaping our lives and livelihoods.Listen on: Apple Podcasts SpotifySupport 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

5 snips
Jun 17, 2025 • 49min
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.

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.

8 snips
Jun 3, 2025 • 45min
DtSR Episode 656 - Deeper Down the AI Rabbithole Part 2
Join Erik Bloch, a technical expert on AI, and John Dickson, who offers insights into its unique characteristics, as they delve deeper into artificial intelligence. They discuss the intricate mechanics and challenges of AI, touching on its energy demands and ethical implications. The conversation shifts to AI's transformative impact on fields like healthcare and law, emphasizing human oversight. They explore the risks of blind trust in AI and hint at the exciting technological evolution ahead, leaving listeners eager for the next installment.

8 snips
May 27, 2025 • 52min
DtSR Episode 655 - John Dickson Down the AI Rabbithole Part 1
In this engaging discussion, John Dickson, CEO of Byte Whisper Security and a security veteran with over 30 years in the field, dives into the fascinating world of AI and security. He humorously shares insights from his career while exploring the complex duality of AI—potentially beneficial yet fraught with risks. The conversation highlights the challenges organizations face in integrating AI into their workflows and emphasizes the need for critical thinking amidst growing technology reliance. Dickson also touches on the importance of preserving traditional skills in a tech-driven world.

10 snips
May 20, 2025 • 44min
DtSR Episode 654 - Can We Teach Machines Discretion?
Sounil Yu, CTO and co-founder of Knostic and former chief scientist at Bank of America, joins to explore the intriguing question of whether machines can be taught discretion. The discussion highlights the implications of AI in a society on the brink of an AI era. Topics include the challenges of data access and the 'need to know' principle in organizations, as well as the necessity for customized AI guardrails to prevent biased outcomes. Yu emphasizes the importance of balancing clean data and strategic access to enhance security in a digital landscape.