When Humans Beat AI With Matt Morris and Mike Bennett from EncorEstate Plans

What happens when AI gives legal advice — and gets it wrong? In this episode, Mark Heynen and James Cantwell sit down with Matt Morris and Mike Bennett from Encore Estate Plans to unpack their viral study comparing ChatGPT, Claude, Perplexity, and Google AI to human estate-planning experts. The results? Some bots aced the basics, others literally gave up halfway through.

From hilarious “ChatGPT Law School” jokes to serious insights about legal accuracy, the conversation explores where AI helps, where it fails, and why human oversight still matters when your life’s assets are on the line. The Encore team also reveals how they’re building their own guarded LLM — trained on four years of real advisor chats — to deliver trustworthy automation without crossing the line into unauthorized legal advice.

Along the way, the group debates VC vs. bootstrapped growth, Harvard’s new “Work Slop” study, and even the future of digital legacies (“Can your trustee delete your browser history?”). It’s a smart, funny, and candid look at the intersection of AI, trust, and mortality — and one you won’t forget.

Listen in to learn why estate planning is becoming the next frontier of human-in-the-loop AI.