35,000 Feet & The Things That Matter

35,000 Feet & The Things That Matter

From Thoughts On Money [TOM] by Trevor Cummings

May 28, 2026 · 38 min

About this episode

Trevor Cummings and Matthew Gregory discuss reframing estate planning as an act of love that alleviates burdens during grief.

This week's blogpost - https://bahnsen.co/4eayQTh Today, Matthew Gregory writes the Thoughts on Money article, and discusses with Trevor about how to reframe estate planning from something morbid into an act of love that protects the people you care about by reducing logistical and legal burdens during grief. Using The Princess Bride’s “prepare to die” line and analogies like board games and omakase, they emphasize starting with basics (wills, trusts, medical directives, powers of attorney, guardianship) before complex strategies, and ensuring plans are stored and understood (even via one-page flowcharts). They note estate planning applies at all ages, including young adults facing HIPAA limits, and can be revisited as life and laws change. Trevor argues estate planning often ranks ahead of investment strategy, and they close by suggesting viewers consider whether planned end-of-life gifts (to family or charity) might be better made during life for qualitative and potential tax benefits. 00:00 Intro 00:49 Estate Planning as Love 03:50 "Prepare to Die" Moment 05:41 Executor Lessons and Family First 08:34 Start Simple, Not Complex 11:38 Settler's of Catan Strategy 16:39 Guided…

People in this episode

Host: Trevor Cummings

Guest: Matthew Gregory

Topics covered

  • estate planning
  • love
  • wills
  • trusts
  • financial strategy
  • family transparency

Keywords

  • estate planning
  • wills
  • trusts
  • medical directives
  • powers of attorney
  • family
  • financial strategy

Mentioned in this episode

Books & works: The Princess Bride

More episodes of Thoughts On Money [TOM]

Explore listener stats, chart rankings, contacts and more on the Thoughts On Money [TOM] podcast page.