Down the Security Rabbithole Podcast (DtSR)

Rafal Los, James Jardine, Jim Tiller

Booking Overview

This is a cybersecurity interview and discussion show featuring recurring external guests who are established security practitioners, executives, authors, and subject-matter experts. PR agencies could credibly pitch cybersecurity leaders, risk and vulnerability-management specialists, technology executives, and authors with practical or contrarian industry insight; booking difficulty is medium because the show regularly features guests but maintains a specialized, credibility-focused standard.

Metrics

Episodes: 762

Frequency: Weekly

Rating: 4.3/5.0

Estimated listeners: 1k-10k

Gender skew: Male

Location: USA

YouTube: 677 subscribers

Contact Information

Publicly listed emails

wh1t3rabbit@ishackingyou.com

Looking for the right person? Join Podseeker to find direct host and producer contacts and manage your podcast outreach.

Host

Rafal Los - Cybersecurity professional and co-host of Down the Security Rabbithole Podcast.

James Jardine - Cybersecurity professional and co-host of Down the Security Rabbithole Podcast.

Jim Tiller - Cybersecurity professional and co-host of Down the Security Rabbithole Podcast.

Booking Intelligence

Booking Requirements

medium

Typical Credentials:

Cybersecurity executives, company operators, researchers, authors, and established practitioners with firsthand experience and a substantive point of view on security, risk, technology, or cybersecurity business leadership.

Required Achievements:

Authored a book or influential industry analysis, Led or operated cybersecurity companies, Built expertise in vulnerability management, cyber risk, or security strategy, Held senior leadership or practitioner roles in the cybersecurity industry

Recent Guest Discussions

Anton Chuvakin - Artificial Intelligence Hype And Safety, Enterprise Technology Limitations, Cybersecurity Implications, And Overreliance On Ai.

Richard Bird - Cybersecurity Metrics, Cyber Risk Management, Cyber Insurance, Security Investment, Accountability, And CISO Leadership.

Robert Hansen - Vulnerability Management, Exploit Prioritization, Patching Strategy, Cyber Risk, And Evidence-based Security Outcomes.

Jeremiah Grossman - Vulnerability Management, Exploit Prioritization, Patching Strategy, Cyber Risk, And Evidence-based Security Outcomes.

Patrick Dennis - Private Equity, Cybersecurity Company Finance, EBITDA, Leverage, Value Creation, Exits, And Operating Discipline.

Recent Topics

Technology, Cybersecurity, Cyber Risk, Vulnerability Management, Cybersecurity Startups

Episodes

Here's the recent few episodes on

Down the Security Rabbithole Podcast (DtSR)

DtSR Episode 725 - The Importance of Communicating Value

September 29, 2026

TL;DR: This episode is all about an essential skill few of us have mastered. How do you communicate value? What is it? And how do you make sure you're evaluating value in a way that makes sense to the person you're talking to? This is something that's essential to your career, your business, and your life, and Michael is a master of this art. Don't miss this one.Guest: Michael SantarcangeloDescriptionMost cybersecurity pros know the feeling: you ship real work, you reduce ...

DtSR Episode 724 - Unpacking the AI Hysteria

September 22, 2026

TL;DR: This week's podcast features Rafal & Anton discussing the hype and hysteria that surrounds today's AI headlines. Which side is right, which side is propaganda, and what's real? Listen and find out.GuestAnton ChuvakinDescriptionAI panic has officially gone mainstream, and we’re feeling it from every direction: “AI will kill us” on one end and “AI is useless hype” on the other. Rafal brings in Anton Chuvakin to filter the noise and ask a simpler question: what’s actual...

DtSR Episode 723 - Richard Bird Security is Built Wrong

September 15, 2026

TL;DR: This week's guest is Richard Bird, who has a new book coming out. He says, "Cybersecurity measures activity while its adversaries measure opportunity," and thirty years of spending has been priced against the wrong scoreboard. Great start, and you know it's going to get a little punchy.Guest:Richard BirdDescriptionCybersecurity spending has exploded for 30 years, and the scoreboard still looks brutal. We sit down with Richard to talk about his new book, “Built Wrong...

Publicly listed emails

wh1t3rabbit@ishackingyou.com

Looking for the right person? Join Podseeker to find direct host and producer contacts and manage your podcast outreach.

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