Estate Planning Wisdom: DIY and AI-Generated Documents

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 Documents00:07 Welcome and Episode Introduction01:00 The Problem with DIY and AI Estate Planning Documents02:00 Execution Formalities Every State Requires04:00 What Happens When a Will Isn't Self-Proving06:00 Capacity, Undue Influence, and the Missing Legal Supervision08:00 When Estate Plans Conflict with Business Agreements09:00 AI Hallucinations and Made-Up Tax Numbers10:00 Contracts vs. the Will: Which One Controls11:00 Prenuptial Agreements, Divorce Decrees, and Beneficiary Designations12:00 Joint Titling and the Limits of a Will13:00 Coordinating with CPAs and Financial Advisors14:00 How AI Blends the Law of Different States15:00 The Fine Print: DIY Disclaimers and Liability17:00 When DIY Estate Planning Actually Works, and When It Doesn't18:00 Beyond the Will: Powers of Attorney and Choosing the Right Agent20:00 Why Even “Simple” Families Need Real Guidance21:00 Reviewing Your Estate Plan Every Three to Five Years22:00 Avoiding Costly Ancillary Probate: A Florida Example23:00 Closing Thoughts Trust Us: Estate Planning Wisdom Episode 15 August 25, 2026 ★ Episode details: https://share.transistor.fm/s/d16eb34a ★ Additional episodes: https://www.offitkurman.com/trust-us-...