Chasing Entropy Podcast by 1Password

This week on Chasing Entropy, host Dave Lewis sits down with Keith Hoodlet, Director of Security Research at 1Password and leader of the newly formed Off by One Labs. Keith describes his team's mission with characteristic wit: throwing stones at glass houses not to hear the crash, but to help people build better, more secure houses. From Battle.net punk to security leader Keith's path in...

In this episode of Chasing Entropy , Dave Lewis sits down with Jaya Baloo, co-founder and COO/CISO of Aisle, to unpack one of the most important shifts happening in cybersecurity right now: the collision of AI, vulnerability management, and operational reality. Jaya’s career spans telecom, cryptography, enterprise security, and AI-driven security research. The conversation moves from early BBS war...

In this episode of The Chasing Entropy Podcast , I talk with Matt O'Leary, who leads M&A and strategic partnerships at 1Password, about what changes when security is tied directly to the product, the brand, and the deal itself. The core idea is simple. When a company makes an acquisition, it inherits the whole business, not just the part that looked attractive in the pitch. That includes...

In this episode of The Chasing Entropy Podcast by 1Password , I speak with Dustin Heywood, known to many as EvilMog, executive managing hacker and senior technical staff member at IBM. The conversation stays grounded in real security work, from password cracking and Active Directory abuse to AI privilege creep and quantum planning. The through line is simple, most security failures start with acce...

Cyber conflict makes more sense when you stop treating it like a technical sideshow and start looking at history, doctrine, and political intent. In this episode of Chasing Entropy , Dave Lewis sits down with analyst and author Allie Mellen to discuss the ideas behind her book Code War , and why the cyber strategies of the United States, China, and Russia reflect much older national patterns. Mell...

SEASON TWO HAS LANDED!  Bob Lord has spent decades building and leading security programs, from early internet crypto work at Netscape to roles at Twitter, Yahoo, the Democratic National Committee, and CISA. In this episode, he and host Dave Lewis get practical about a simple problem, the security advice most people hear does not match how real compromises happen. We start with the myths Bob track...

In this episode of Chasing Entropy, I sit down with Kane Narraway, a security leader who has built and scaled Zero Trust environments at companies like Atlassian, Shopify, and Canva. Together, we explore the evolution of cybersecurity, from digital forensics to agentic AI, and the ongoing tension between innovation and control. From Forensics to Frameworks Kane’s journey into cybersecurity began w...

In this episode of the Chasing Entropy Podcast , I am joined by Joe Carson, Chief Security Evangelist and Advisory CISO at Delinea (formerly Thycotic), to explore how personal history, technology evolution, and emerging AI challenges shape the cybersecurity landscape. From Gaming to Global Security Joe shares his journey from growing up in Belfast with an early passion for gaming and coding, to bu...

In this episode of Chasing Entropy , I sit down with Heidi Potter, longtime organizer of ShmooCon and now CEO of Turngate, for a heartfelt conversation about community, chaos, and legacy in cybersecurity. From ShmooCon to What’s Next For 20 years, Heidi helped shape ShmooCon into one of the most influential community-driven conferences in the industry. She reflects on the decision to sunset the ev...

In this episode of Chasing Entropy Podcast , I spoke with Paul Klein about the emerging “agentic web”, where AI agents perform real-world digital tasks on our behalf. Paul shares how Browserbase builds secure infrastructure for these agents to interact with websites safely, and how new integrations with 1Password’s Agentic Autofill enable secure, human-approved credential use without exposing secr...

In this episode of Chasing Entropy , I sit down with Dhillon Kannabhiran, the founder of the long-running Hack in the Box (HITB) Security Conference, to explore the origins, evolution, and impact of one of the world’s most influential hacker gatherings. From Kuala Lumpur to Global Stages Dhillon shares the unlikely beginnings of HITB in Malaysia, started as a scrappy, accessible alternative to hig...

In this episode of Chasing Entropy , I sit down with Cole Grolmus , founder of Strategy of Security , to explore the often-overlooked world where cybersecurity and mergers & acquisitions (M&A) collide. The Journey to Strategy of Security Cole shares his path from early sysadmin roles in Iowa to a decade at PwC, where he worked on large-scale cybersecurity transformations. Along the way, he...

From a tank driver in the Gulf War to the founder of one of the U.S.’s largest regional cybersecurity conferences, Michael Farnum’s journey is a study in discipline, community, and curiosity. He shares how early exposure to cryptography, BASIC programming pranks, and first encounters with firewalls led him into security. We dive into how Farnum built the Houston Security Conference (HOU.SEC.CON) f...

This week I got to sit down with Brian Levine who is a cybersecurity consultant and former U.S. DOJ cybercrime prosecutor, to unpack how security risks shape mergers, acquisitions, divestitures, and investments. We cover what really moves deal price and structure, why early cyber due diligence matters, and how to protect “Day 1” operations without blowing up the integration plan.  Brian Levine, Cy...

In the 20th episode of the Chasing Entropy Podcast , Dave Lewis sits down with Trey Ford, Chief Strategy & Trust Officer at Bugcrowd and former General Manager of Black Hat, to explore the realities of modern cybersecurity leadership. From the pitfalls of annual penetration tests to the messy realities of vulnerability disclosure, Trey shares lessons from decades in the field. He explains why...

In this episode of Chasing Entropy , host Dave Lewis, Global Advisory CISO at 1Password, sits down with Jacob DePriest, the newly appointed CISO and CIO at 1Password. Together, they explore the intersection of security, IT, and the human factors that shape how we defend and sometimes undermine our digital world. From NSA to GitHub to 1Password Jacob traces his path from early engineering work at t...

In this episode of the Chasing Entropy Podcast , host Dave Lewis, Global Advisory CISO at 1Password, sits down with Rob Fuller (a.k.a. Mubix), cybersecurity leader, Marine Corps veteran, red teamer, and technical advisor—to explore the twists, turns, and lessons from a career built at the intersection of curiosity, community, and defense. Early Sparks of Curiosity Rob shares how tinkering with Gam...

In this episode of Chasing Entropy , Dave Lewis sits down with longtime friend and industry veteran Bill Brenner , Senior VP and Head of Content at Cyber Risk Alliance. Bill has been shaping the cybersecurity narrative for over two decades, from his early reporting days at TechTarget to his leadership roles at Akamai, Sophos, IANS, and now Cyber Risk Alliance. From Newsrooms to Cybersecurity Bill...

In this episode of the Chasing Entropy Podcast , host Dave Lewis welcomes industry analyst and long-time cybersecurity veteran Fernando Montenegro for a far-ranging and refreshingly honest discussion about the evolution of security, the realities of AI, and the human stories that shape our digital defenses. Fernando shares his origin story from math and fractals in Brazil to cryptography and bulle...

In this special "Summer Camp" edition of Chasing Entropy , Dave Lewis sits down with longtime friend and cyber risk veteran Jeffrey Wheatman. From their early DEF CON gooning days to leading board-level security conversations, Dave and Jeffrey explore how cybersecurity professionals navigate entropy—when systems unravel, and chaos creeps in. Jeffrey, a former VP at Gartner and now a cybe...

In this episode of the Chasing Entropy Podcast, I am joined by Singapore-based cybersecurity leader Emil Tan, a man who wears many hats and wears them well. From government defense to grassroots community building, Emil’s journey is a masterclass in adaptability, curiosity, and community spirit in cybersecurity. Who Is Emil Tan? Emil is a cybersecurity polymath: a national defense contributor at B...

In this heartfelt and wide-ranging conversation on the Chasing Entropy Podcast, I get to sit down with my friend, legendary storyteller, and community-builder Jack Daniel to trace a truly unique career journey, one that spans grease-stained garages, green-screen terminals, the early internet, and the global expansion of the BSides movement. From Mechanic to Cybersecurity Strategist Jack shares sto...

In this episode of the Chasing Entropy Podcast , host Dave Lewis sits down with Dr. Grigorios Fragkos, widely known as Dr. Greg, a cybersecurity veteran with deep roots in academia, government, and enterprise defense. From the early days of building near real-time threat detection systems to orchestrating national-level cyber defense initiatives, Dr. Greg shares a dynamic perspective on the ever-e...

In this episode of the Chasing Entropy Podcast, host Dave Lewis sits down with the incomparable Javvad Malik, security advocate, Guinness World Record holder, and co-host of the Host Unknown podcast. What follows is a dynamic, humorous, and insightful conversation that spans decades of cybersecurity experience, unconventional career moves, and the art of connecting with people on stage, on camera,...

In this episode of the  Chasing Entropy Podcast , I speak with Mark Hillick, CISO at Brex, about the changing role of security leaders in a world shaped by AI, rapid innovation, and shifting business expectations. From building security culture at Riot Games to navigating Silicon Valley’s AI gold rush, Hillick offers grounded insight into what it takes to lead a modern, business-aligned security t...