The Ascent – When Estate Planning Goes Wrong

Hosted by Sam McGee, Crestmont Private Wealth | Guest: Scott Seidl, Attorney at Keen Miller LLP

In this episode, Sam sits down with estate litigation attorney Scott Seidl to discuss what happens when estate planning goes wrong — from contested wills to capacity disputes — and why having a solid, well-communicated plan in place is critical for families and business owners alike.

Key Takeaways:

An ounce of prevention is worth a pound of cure — contested wills are costly, nasty, and rarely end with anyone truly "winning"

Blended families and divorce are major drivers of estate disputes today

Lack of communication — not just lack of planning — is a root cause of litigation

Capacity challenges are among the most expensive and difficult cases to litigate; don't wait too long to get your plan in order

Wealth level is NOT the biggest predictor of whether a dispute will arise — family dynamics and personality are

0:00 – Introduction: Sam McGee welcomes estate litigation attorney Scott Sidle of Keen Miller LLP

0:37 – Disclaimer: Scott clarifies this is general information only, not legal advice

0:58 – Why estate planning matters: Beyond "you need a will" — discussing real consequences of being unprepared

2:22 – Scott's day-to-day: The pitfalls he sees in contested estates and trusts at Harris County Courthouse

2:45 – Scott's practice area: Litigation (the cure), not planning (the prevention) — and why comprehensive planning makes his job easier

3:41 – The cost of disputes: Court costs, thousands in fees, and no one really wins

5:00 – How common are contested estates? The role of personality, family dynamics, and wealth

5:51 – Blended families: A major driver of estate disputes — step-children, step-parents, and second marriages

6:58 – The real culprit: Lack of communication, not just lack of planning — secrecy creates surprise and litigation

7:31 – Simon Sinek story: Sam shares a study on communication gaps and why even "clear" messages aren't always received

9:10 – Step one vs. step two: Getting the plan in place first, then communicating it to heirs

10:36 – "The sins of the father" conversation: What Scott tells unhappy heirs about their parents' rights to their own assets

11:24 – Capacity challenges: How mental capacity questions drive 75–80% of contested will cases

12:27 – Why capacity fights are so costly: Rarely resolved by summary judgment, almost always go to trial

12:52 – Key takeaway: "That is not wealth creation or preservation. That is wealth destruction."

13:14 – Call to action: Reach Crestmont Private Wealth at crestmontpw.com; reach Scott Sidle at keenmiller.com or LinkedIn

14:20 – Outro: Sam wraps up and invites listeners to connect

Original Air Date: April 25, 2026 at 8:30am as heard on Boerne Radio 103.9FM

Contact:  www.crestmontpw.com 

Alec Walker in Houston:  831-280-5288 

Sam McGee in Boerne: 830-368-2898