If you’ve ever wondered whether you should pass on your money now or make your heirs wait for the “big reveal” (cue the dramatic reading of your will), this is your episode. Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant from Afford Anything and Jesse Cramer from Personal Finance for Long-Term Investors to play a high-stakes round of “In or Out” with estate planning and charitable giving. Is anonymous giving a waste of good publicity? Should you set up a donor-advised fund or keep it simple? Is sharing your estate plan with your heirs wise—or an invitation to awkward holiday dinners?
This isn’t your average dry legal seminar. Between football analogies, dinosaur jokes, and the occasional jab at Ford’s electric truck sales, our crew digs into the real-life choices Stackers face when deciding how—and when—to pass along their wealth. You’ll hear hot takes, smart strategies, and maybe even a nudge to start that conversation you’ve been putting off.
From the practical (avoiding probate, maximizing giving impact) to the philosophical (why give at all, and how much?), this episode blends useful tactics with the irreverent basement energy you know and love. It’s part money talk, part game show, and 100% designed to get you thinking about your financial legacy.
The pros and cons of giving now versus after you’re gone
How donor-advised funds work and whether they’re worth your time
Why anonymous giving might be overrated—or a hidden superpower
Ways to avoid family drama by (maybe) sharing your estate plan early
How to think about charitable giving as part of your overall financial plan
Questions to ponder during the show:
Would you rather give now and see the impact, or give later and leave a surprise?
How much transparency do you think heirs deserve about your estate plans?
If you give anonymously, are you missing an opportunity—or dodging a headache?
What would you want your charitable legacy to look like?
FULL SHOW NOTES: https://stackingbenjamins.com/estate-planning-giving-week-in-or-out-1725
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
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