Ep. 99 – Breaches, Births and Bat...

Ep. 99 – Breaches, Births and Battling BS // Rob Black

Adventures of Alice & Bob by Merchants Media
Apr 13, 2026
51:55

Episode notes

In this episode, James Maude sits down with Rob Black, founder and CEO of Fractional CISO, who started his career at RSA Security and had a front-row seat to one of the most consequential breaches in cybersecurity history, all while his wife was going into labor with their first child. From inventing patents at RSA to starting a one-man LinkedIn crusade against "SOC 2 in two weeks" scams, Rob's stories are equal parts entertaining and infuriating. He explains why compliance theater is actively making companies less secure, why your CEO needs to hear things with a dollar value, and why you should think about cybersecurity less like an asteroid and more like a roulette wheel. Plus, why the "Lexus of Fractional CISOs" doesn't own a single IoT device.