35,000 Feet & The Things That Matter episode artwork

EPISODE · May 28, 2026 · 38 MIN

35,000 Feet & The Things That Matter

from Thoughts On Money [TOM] · host Trevor Cummings

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 Advice, Omakase Style 19:59 Estate Planning Before Investing 25:47 All Ages and Family Transparency 27:52 Avoid Overengineering the Plan 32:45 Lean Into Discomfort 33:48 Give While Living 35:57 Wrap Up and Conclusions Links mentioned in this episode: http://thoughtsonmoney.com http://thebahnsengroup.com

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35,000 Feet & The Things That Matter

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This episode was published on May 28, 2026.

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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...

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