Estate Planning, Charitable Giving, and Financial Hot Takes (SB1725)

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Aug 22, 2025

Paula Pant, a negotiation expert from Afford Anything, teams up with Jesse Cramer, a financial strategist for long-term investors. They dive into the intriguing debate of giving now versus later and the benefits of donor-advised funds. Discover whether anonymous donations are underrated superpowers or publicity lost. The conversation takes a lighthearted turn with humor and relatable anecdotes, making complex topics like estate planning more accessible, while encouraging you to start those important financial legacy conversations.

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ADVICE

Hire An Attorney For Complex Estates

Hire an attorney for estate planning once your situation is complex or you have dependents.
Use DIY wills only when you are very young, single, and have few assets.

ADVICE

Prioritize Kids In Estate Plans

If you have children, get professional estate planning to name guardians and set terms.
Use beneficiaries for simple accounts but don't rely on them alone for child care decisions.

ANECDOTE

Choosing A Guardian Was Tough

Jesse found naming a guardian for his young child emotionally difficult and complex.
He weighed factors like age, proximity, willingness, and future fitness of potential guardians.

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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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