Hosts Danielle Friedman, Herb Fineburg, and Max McCauley, estates and trusts attorneys, break down the risks of using AI tools and online services to prepare wills, trusts, and powers of attorney. Danielle, Herb, and Max walk through the execution formalities that vary by state, the trouble that surfaces when a will is not self-proving, and the court battles that can follow when questions of capacity or undue influence go unaddressed. They explain why business agreements, prenuptial agreements, divorce decrees, and beneficiary designations all take priority over a will, and share real examples of AI producing incorrect tax figures, hallucinated statutes, and advice that blends the law of multiple states together. The conversation closes with practical guidance on coordinating an estate plan with CPAs and financial advisors, choosing the right agents and fiduciaries, and reviewing documents every three to five years.

00:00 Estate Planning: The Pitfalls of DIY and AI-Generated Documents

00:07 Welcome and Episode Introduction

01:00 The Problem with DIY and AI Estate Planning Documents

02:00 Execution Formalities Every State Requires

04:00 What Happens When a Will Isn't Self-Proving

06:00 Capacity, Undue Influence, and the Missing Legal Supervision

08:00 When Estate Plans Conflict with Business Agreements

09:00 AI Hallucinations and Made-Up Tax Numbers

10:00 Contracts vs. the Will: Which One Controls

11:00 Prenuptial Agreements, Divorce Decrees, and Beneficiary Designations

12:00 Joint Titling and the Limits of a Will

13:00 Coordinating with CPAs and Financial Advisors

14:00 How AI Blends the Law of Different States

15:00 The Fine Print: DIY Disclaimers and Liability

17:00 When DIY Estate Planning Actually Works, and When It Doesn't

18:00 Beyond the Will: Powers of Attorney and Choosing the Right Agent

20:00 Why Even “Simple” Families Need Real Guidance

21:00 Reviewing Your Estate Plan Every Three to Five Years

22:00 Avoiding Costly Ancillary Probate: A Florida Example

23:00 Closing Thoughts