Chasing Entropy Podcast 024: Dhillon of Hack in the Box on Conferences, Chaos, and the Future of Security

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 high-cost events like Black Hat. Against all odds, and skepticism that “nobody would come to Malaysia”, HITB attracted global speakers and quickly became a fixture in Asia, the Middle East, and Europe. Along the way came wild stories of last-minute chaos, cultural exchanges, and the conference’s deliberate focus on building community through face-to-face connections.

Curating Talks and Building Community

The conversation dives into how talks are chosen, balancing technical depth with accessibility, and ensuring new voices get a platform. Dhillon emphasizes that HITB isn’t just about the talks you can rewatch later, it’s about hallway conversations, TCP/IP networking sessions, and serendipitous encounters that spark startups, collaborations, and lifelong friendships.

Security Lessons (and Non-Lessons)

Looking back at two decades of research presented at HITB, Dhillon is candid: many of the same problems persist, only shifted into new technologies. From classic exploits to today’s “vibe coding” and AI-assisted development, human error and misunderstanding remain the root causes of vulnerabilities. Still, this constant reinvention ensures hackers, and defenders, will never run out of work.

AI, Translation, and the Future of Conferences

The discussion expands to how AI is reshaping both hacking and events. From bug-hunting orchestration with AI agents to real-time language translation devices, the tools are changing fast. Dhillon warns of risks like AI-generated deepfakes but also highlights opportunities for accessibility, inclusivity, and global collaboration.

Words to Hack By

Dhillon closes with advice for hackers and builders alike: “Try stuff out. Don’t hold back. Don’t think there’s going to be a tomorrow. Do whatever you can today. Keep hacking, bro.”