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#60: Cash in the Cyber Sheets - AI, T&C, and the Never-Ending Vendor Rodeo

Season #1

In Episode 60 of Cash in the Cyber Sheets, we dive into the rapidly morphing world of AI and its increasingly tangled role in third-party software, supplier relationships, and data access controls.

Remember when vetting vendors was a once-a-year checkbox and not a full-contact sport? Good times. But now, thanks to AI creeping into every crevice of modern software—from CRMs to coffee machine firmware—the game has changed.

Now every supplier, integration, and platform you rely on might quietly include AI. And that means your data, your customers’ data, and your business logic could be influenced (or exposed) in ways you never explicitly agreed to—or even realized. Worse, by the time you finish evaluating one vendor’s AI usage, the terms of service have changed again. It’s like chasing a greased compliance pig through a foggy maze.

This episode explores:

  • Why the growing use of AI in nearly all SaaS tools creates cascading compliance complexity.

  • How T&Cs around AI use are changing at whiplash speed—and what that means for your contracts.

  • The evolving (and frankly exhausting) need to re-vet vendors on an ongoing basis.

  • How “silent AI integrations” can erode your data governance without triggering alarms.

We’re not just sounding the alarm; we’re opening the floor. What are you seeing? How are you managing the ever-evolving AI-supplier matrix? We want to hear your stories, rants, and success hacks.

Whether you're a CISO juggling vendor reviews like flaming swords or a founder wondering if your new billing tool has a secret AI feature rewriting your invoice terms, this episode is your reality check.

💬 Comment. Vent. Share. Then come back for Episode 61—we’ll still be trying to make sense of it all.