Ep. 30: The Security Career Reality Check with May Brooks-Kempler

Let’s be honest: Not everyone’s cut out to be the boss, and those who are often don’t want the job. That’s especially true in security, where many people consider the role of Chief Information Security Officer (CISO) more of a sentence than a promotion. Executive, author, podcaster and recovering CISO May Brooks-Kempler gives us her take on whether sitting in the big chair is all it’s cracked up to be, as well as her unorthodox take on privacy that’ll get you thinking.

We jump back into the world of generative AI with CEO and entrepreneur Michael Silva. Michael gives us his take on how a large language model (LLM) can steer you wrong and how to stay on a path to reality.

What is threat intelligence, and what makes it so...threat-y? Ryan Westman of eSentire explains it to us, and also shows us a neat Mac trick that'll make you feel better about overpaying for a laptop.

What we’re drinking: Buffalo Trace bourbon

Security consulting executive Reut Weitzman returns to the show to talk about one of our favorite topics, conducting a purple team exercise. Join us to learn what happens when attackers square off against defenders to test a security team’s capabilities.

What we’re drinking: Strawberry Gin & Tonic

Security incident response veteran John Dwyer joins us for a deep dive into how AI is poised to bend reality, and what that means for both attackers and defenders. We also cover how security incidents are now straddling the cyber and real worlds. Join us for some fresh thinking on where security is headed.

What we’re drinking: Bourbon and Ginger

Legendary spy hunter and security thought leader Eric O’Neill puts the cost of cybercrime worldwide at seven trillion dollars. Eric joins us to share his sobering thoughts about that and other topics including the Dark Web, ransomware and infrastructure vulnerability. Plus some bonus tips for driving in DC.

What we’re drinking: Bourbon

Security veteran Monte Fabiani tells us about the many SOCs (Security Operations Centers) he’s built and run, and how being in that end of the business can make it hard to sleep at night. We also get meta about how we started podcasting and brainstorm some future ideas.

What we’re drinking: What we drank when we were young(er)

The holidays are a time for joy. It’s also a time when thieves and scammers up their game in the cyber world, looking to put a damper on everyone’s good cheer. Security consultant Reut Weitzman joins us to share tips to keep the bad guys from spoiling your holidays.

What we’re drinking: Negroni

Everyone in security says they’re committed to Zero Trust, even if they can’t agree on what it means. We take on the challenge of explaining the security industry’s favorite buzzword and the bizarre mythology around it, with the help of guest Adam Kohler and a few sips of bourbon. (Well, maybe not sips. And maybe more than a few.)

What we’re drinking: Bourbon

It's our Halloween episode, and we're covering the scary topic of medical device security with guest Gabrielle Hempel, aka @gabsmashh. Gabrielle talks about her experiences with medical devices and her unconventional path into information security.  

What we’re drinking: Whiskey