Aaron Portnoy on Pwn2Own, the End of Easy Bugs, and AI-Fueled Offense

From Three Buddy Problem by Security Conversations

May 27, 2026 · 40 min

About this episode

Aaron Portnoy discusses the evolution of Pwn2Own, the impact of AI on vulnerability discovery, and the future of cybersecurity.

( Presented by TLPBLACK : A cybersecurity intelligence platform focused on sharing curated, high-sensitivity threat insights and research with trusted security professionals. ) Three Buddy Problem x Ekoparty Miami : Aaron Portnoy (Zero Day Initiative alum, early Pwn2Own organizer, and now at Mindgard) joins us at Ekoparty Miami to reminisce on the early days of the hacking contest, where vulnerabilities actually live (the boundaries between systems, not inside them), why LLMs will take out the trash but can't dream up the next speculative-execution-class bug, and the coming patching apocalypse when discovery 10x's overnight. Plus, why your SOC is a forensic historian, the promise of hijacking an attacker's reward loop with deception tech, and the legendary story of carrying a Walmart "fat stack" of cash to bootstrap Ekoparty in Buenos Aires. Cast: Juan Andres Guerrero-Saade , Ryan Naraine and Aaron Portnoy . Timestamps: 0:00 — Introductory banter 1:17 — Dropping out, iDefense, and getting good at reversing everything 2:19 — How Pwn2Own got started 4:15 — The most impressive Pwn2Own ever: Nils, VUPEN, and exploit "art" 5:59 — "iPhone hacked in 30 seconds" — and the 18 months…

People in this episode

Hosts: Juan Andres Guerrero-Saade, Ryan Naraine

Guest: Aaron Portnoy

Topics covered

cybersecurity
hacking contests
AI in security
vulnerability discovery
deception technology
Pwn2Own history

Keywords

Pwn2Own
cybersecurity
AI
vulnerabilities
deception technology
Ekoparty
hacking

Mentioned in this episode

Organizations: Zero Day Initiative, Mindgard

Places: Ekoparty Miami, Buenos Aires