Episode Summary In this follow-up episode of Trust Issues, Ruma Mazumdar welcomes back executive coach and AI expert Jesse Frye to discuss how AI is reshaping estate planning and what legal professionals need to know. From DIY will platforms to agentic AI tools that mimic human workflows, Ruma and Jesse dig into the promises, pitfalls, and personal hesitations around using AI in people-centered legal practices. They explore how to identify friction points, personalize client experiences, and scale law firms—without sacrificing trust. This is an essential conversation for anyone navigating the evolving balance between automation and empathy in law.

Key Timestamps 00:01 – Welcome Back: AI + Estate Planning Round 2 01:14 – The Rise of DIY Estate Planning Platforms 03:35 – Ruma’s Concerns: Where AI Helps vs. Where It Feels Cold 05:02 – Why Clients Still Need Human Advisors 07:10 – Could an AI Avatar Guide Clients Through Your Process? 09:45 – Mindset Shift: Delegating Without Abdicating 12:20 – Can Video Replace Face Time? How to Know What Clients Want 14:18 – The DMV Example: When AI Actually Improves the Experience 17:10 – Agentic AI for Legal Marketing & Admin Tasks 20:00 – Personalization vs. Automation: Where AI Shines 23:05 – The Admin Time Trap: Using AI for Time Tracking & Cost Control 25:30 – Better Research, Faster Results: Ruma’s AI Research Tips 28:00 – How to Start with AI Without Getting Overwhelmed 30:45 – Why You Shouldn’t Sign Long-Term Contracts with AI Vendors 33:00 – The VC Landscape: What’s Growing, What’s Getting Acquired 35:14 – Final Thoughts: How to Vet AI Tools in Your Legal Practice 36:50 – Where to Find Jesse Frye Online 38:10 – A Bit of Nostalgia: Coaching Memories & First-Year Doubts

About the Show

Trust Issues is hosted by estate planning attorney Ruma Mazumdar, who tackles the evolving challenges and innovations in law, leadership, and entrepreneurship. Through candid conversations with experts and disruptors, the show helps legal professionals build smarter, more resilient, and more human-centered practices in a digital-first world.

Episode Summary

In this eye-opening episode of Trust Issues, host Ruma Mazumdar sits down with Jesse Frye, an executive coach and AI expert, to explore the rapidly evolving intersection of AI and legal services. Together, they unpack the rise of agentic AI, what it means for lawyers, and how legal professionals can leverage automation to increase efficiency—without losing the human touch. From replacing mundane admin tasks to enhancing estate planning workflows, this conversation demystifies what AI can and can’t do for your firm and why fear shouldn’t hold you back from embracing it.

Key Timestamps 00:01 – Welcome to Trust Issues 01:18 – Meet Jesse Frye: From Legal Coaching to AI Integration 03:30 – What Is Agentic AI? How It’s Different From Traditional Automation 06:22 – Using AI to Automate Legal Intake, Scheduling & Matter Creation 09:40 – Will AI Eliminate Legal Jobs? The Truth About Workforce Disruption 13:15 – Why Lawyers Should View AI as an Opportunity, Not a Threat 15:35 – What AI Still Can’t Do: The Role of Attorneys in an AI World 18:30 – Overcoming Fear: How to Encourage Teams to Use AI Tools 21:18 – First Steps: Building Comfort with Everyday Use Cases 24:10 – Where to Start: Identifying Friction Points in Your Law Firm 28:20 – How to Apply AI to Estate Planning and Legal Drafting 31:45 – Why RAG (Retrieval-Augmented Generation) Is a Game-Changer 34:00 – Ethical Use of AI: You’re Still Responsible for What AI Produces 36:18 – Outro: More to Come in Part Two on Estate Planning with AI

About the Show

Trust Issues is a podcast hosted by Ruma Mazumdar, focused on challenging norms in law, leadership, and entrepreneurship. Each episode features bold conversations with experts who are rewriting the rules in their industries—offering practical advice and strategic insights for forward-thinking professionals.

Episode Summary:

Ruma Mazumdar shares her raw, unfiltered journey of building Key Esquire law firm from the ground up. From leaving a six-figure corporate job to navigating the challenges of hiring, firing, and establishing a sustainable business culture, this episode offers valuable insights for entrepreneurs in their early stages.

Key Timestamps:

00:01 - Introduction

00:07 - Beginning of Key Esquire's journey

03:45 - First year challenges and hiring experiences

06:30 - Leadership lessons and mindset shifts

08:15 - Working with a business coach

10:20 - Evolution as a CEO and current leadership approach

About The Show:

“Trust Issues” is a podcast that explores the intricacies of building wealth through trust and integrity. Each episode delivers actionable insights and authentic stories from industry leaders and entrepreneurs.