What happens when the queen of legal AI meets the queen of data privacy? You get an hour of zero filter, zero fluff, and zero apology.

Debbie is a globally recognized authority on data privacy and emerging technology with more than 20 years advising organizations across AI, AdTech, FinTech, and biometrics. Her podcast ranks in the top 2% of 4.6 million podcasts worldwide with more than a million downloads. She is also taking the stage at Masters AI Chicago on April 16 at Willis Tower.

Together they get into what agentic AI actually means for lawyers handling sensitive data, where privacy law is sprinting to keep up with generative AI, how to build a brand that outlasts the hype, and what the evolution from eDiscovery to privacy tells us about where legal careers are heading next.

This is not slowing down.

In this conversation Cat Casey sits down with the man behind the magic to find out what it takes to build the legal industry's biggest stage, why he left to build something even bigger, and what legal education has been getting wrong long before AI showed up to expose it.

They get into what lawyers actually need to learn about AI versus what they are being sold, why most legal AI training programs miss the point entirely, what a real certification program for legal professionals looks like, and what Kevin is most excited and most clear-eyed about as Masters AI builds out its global platform.

This is not a conversation about a conference. It is a conversation about whether the legal industry is serious about actually learning to use AI, or just performing like it is.

Kevin Vermeulen is CEO of Masters AI and Masters Legal AI, the legal industry's first global AI learning ecosystem offering certifications, events, and hands-on training for lawyers, legal ops leaders, in-house counsel, and eDiscovery professionals.

Chat data, collaboration tools, and modern data sources are breaking eDiscovery workflows that were never built to handle them. The question is not whether to adapt. It is whether your deployment model gives you enough flexibility to do it without blowing up your case team in the process.

Brian Kelley, VP of Product at CloudNine, joins Cat Casey to dig into why on-prem and flexible deployment are back in serious conversations, what modern data complexity is actually costing litigation teams right now, and why the teams struggling most are the ones locked into one-size-fits-all workflows that stopped fitting years ago.

If you are navigating messy data sources, evaluating your deployment options, or trying to build an eDiscovery workflow your non-technical case team can actually use, this one is for you.

Topics: eDiscovery, cloud eDiscovery, on-premises eDiscovery, flexible deployment, collaboration tools legal, chat data eDiscovery, modern data, legal technology, litigation technology, legal ops, data management, CloudNine, TechnoCat, Cat Casey, Brian Kelley

Cat Casey sits down live from Legalweek 2025 with Candi Smith, eDiscovery Analyst at Disney, to talk about what that shift actually looks like from inside one of the world's most recognizable enterprise legal operations. They get into where eDiscovery is heading, what AI is actually changing versus what is still hype, and why the vibe at Legalweek this year felt like the beginning of something new rather than more of the same.

Real talk from someone doing the work at enterprise scale. No stage answers. Just the conversation happening in the room where it matters.

Topics: eDiscovery, legal technology, legal AI, AI in legal, Legalweek 2025, enterprise eDiscovery, eDiscovery trends, legal tech transformation, data management legal, litigation technology, legal ops, Disney, Candi Smith, TechnoCat, Cat Casey