AI: The Ultimate Hacker or Cybersecurity’s Best Ally?

In this week’s episode of Cyber After Hours (S1E13 – The Role of AI in Offensive Cybersecurity), we crack open a few drinks and an even bigger debate: Is AI leveling the playing field in cyber, or tilting it in favor of the bad guys?

AI-powered attacks are no longer some sci-fi concept. Generative AI is handing cybercriminals—yes, even the amateurs—a playbook for crafting hyper-realistic phishing campaigns, automating reconnaissance, and scaling attacks like never before.

Financial services and other regulated industries are left wondering:

- Can they afford to stick with the status quo?

- And what happens when AI starts battling itself?

- How far off is a world where autonomous AI defends against AI-driven attacks?

Spoiler: There’s an Irish whiskey bet riding on this one.

Of course, it wouldn’t be Cyber After Hours without a few detours—like our take on Microsoft’s latest strong-arming tactics with Outlook (seriously, who asked for this?).

Plus, we get personal about the entrepreneurial grind and the unexpected lessons that come with it.

So, grab a drink, tune in, and let’s talk about the future of offensive AI in cybersecurity—because ready or not, it’s already here.