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Last week, the internet had one of its worst stretches in memory. Between October 19th and 22nd, dozens of serious security problems came to light within a few days. Online, people started calling it “Black October.”

Much of the coverage has framed this as a story about AI-powered hackers. Frank Riccardi, who joins me today, has spent years making a less dramatic argument. He says most cyberattacks succeed because organizations neglect the basics, things like weak passwords and software that never gets patched. 

Frank Riccardi is an attorney and cybersecurity and privacy expert who spent 25 years building compliance and privacy programs for large healthcare systems. As a Chief Compliance and Privacy Officer, he oversaw investigations into high-profile data breaches. His YouTube Channel is the go-to channel for all things Cybersecurity.

He is the author of Mobilizing the C-Suite: Waging War Against Cyberattacks, released this fall in a revised edition that takes on the growing push to hold executives personally accountable for breaches. His newest book, CTRL+ALT+PWN: The Hacker’s Playbook (And How to Beat It), is written for everyone who has ever reused a password. 

We recorded this conversation before Black October. Frank’s arguments hold up remarkably well, but you won’t hear him mention last week’s events in our main conversation. So stay tuned after it ends. Frank and I sat down again for a short follow-up to talk about Black October directly.

One more thing. Frank’s author bio promises readers that he is a real human being and not a bot, which makes him an ideal guest for this show.