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From SQL Injection to Cloudflare VP: Chema Alonso on 25 Years of Hacking
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
View all episodes
By CloudflareIn 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