Show Notes
In this episode of This Week in NET, host João Tomé is joined by Chema Alonso, Vice President and Head of International Development at Cloudflare.
Chema shares how a 1998 paper on SQL injection launched his career in hacking, his path from running a startup in Madrid to becoming a Microsoft MVP for 14 years, and how he ended up leading cybersecurity at Telefónica for more than a decade — after telling them “you don’t have enough money to make me work for you.” He also explains why he left Telefónica in 2025 to join Cloudflare, and what surprised him about the company’s technical depth.
The conversation explores how AI is changing cybersecurity, from AI agents competing in Capture-the-Flag contests to automated attack chains running around the clock. Chema also discusses the black market for zero-day vulnerabilities, Cloudflare’s role in Europe, and how AI may reshape the economics of the Internet.
We also hear the story behind his famous beanie hat, a Bluetooth exploit that Apple initially called “a feature” until Steve Wozniak got involved and a quick-fire round covering his first computer, favorite hacks, admired researchers, and why Gemini once hallucinated that he went to jail.
⏱️ Timestamps 01:00 — How SQL injection in 1998 started his career 02:36 — From startup to Microsoft MVP to training Spain's cyber forces 04:36 — Black Hat, Def Con, and the global hacking scene 05:53 — How Telefonica recruited Chema 08:49 — 20 years of daily blogging as "brain gym" 10:27 — The beanie hat origin story 14:34 — Why he left Telefonica to join Cloudflare 17:41 — What customers are most worried about: AI security 22:55 — Cloudflare's role in Europe: sovereignty, resilience, and growth 26:58 — How AI is disrupting the Internet's business model 28:44 — The evolution of hacking: from phreaking to AI agents 37:42 — The Dirty Tooth iPhone Bluetooth exploit and Steve Wozniak 41:39 — Quick-fire round: first computer, favorite hack, Kevin Mitnick 43:58 — Google Gemini hallucinated that Chema went to jail 46:49 — The future of the Internet and Cloudflare
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