Random but Memorable

How to spot AI-generated phishing emails with Bron Gondwana from Fastmail

Random but Memorable

Show Notes

Are cybersecurity professionals more burned out than ever? 😩🧠 From alert fatigue to constant vigilance, we unpack what’s driving increased stress — and what organizations can do to build sustainable security teams.

Plus, we take a deep dive into spear phishing. In Crash Course, you’ll learn why it’s so effective and how AI is making targeted attacks more convincing than ever. Bron Gondwana, CEO of Fastmail joins the show later on to explore what AI-powered phishing looks like from inside your inbox. From tracking pixels to hyper-personalised scams, Bron shares what’s changing, which red flags still matter, and the simple habits that can keep you one step ahead. 📩🚩

We even make time to debunk password manager myths in #Ask1Password! 🔤

More from Random but Memorable

Oct 15, 2026

Is your business truly audit-ready, or are you just hoping for the best? 📋🔐

Oct 1, 2026

Is shadow AI quietly creating risk inside your business? 🤖🔐 In this episode of Random but Memorable, you’ll learn what happens when employees adopt AI tools faster than teams can track them.

Sep 10, 2026

We all know AI models are getting better at finding software vulnerabilities. But can they fix them without creating new problems? In this episode, Wade sits down with Keith Hoodlet, 1Password’s Director of Security Research, to discuss new findings from Off-by-1 Labs.

Aug 20, 2026

We’re back for a brand-new season! 🎉 And we're kicking things off with an evolving security risk in the AI space: prompt injection attacks. 🤖⚠️

Aug 6, 2026

Always-on access might sound convenient, but it can quietly become a serious security risk. 🔐⚠️ In this bonus episode of Random but Memorable, we’re joined by Rom Carmel, VP of Product Management at 1Password, to introduce 1Password Privileged Access.

See all episodes →