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The Stacking Benjamins Show

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

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Personal Finance, Financial Planning, Education, Retirement, Investing, Cfp, Business, Money

4.4 • 2K Ratings

🗓️ 22 August 2025

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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:

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Transcript

Click on a timestamp to play from that location

0:00.0

30 seconds to hair.

0:02.0

What do you think about flowers? I think we should have. These are for the gas. Where's that tape? Do you want to have the promo for a show now? Wait, where's the Fiji water? Is this, this isn't, is this tap water? 15 seconds. Can somebody get the cat? I can't drink the cat. Can someone tell Joe's mom to stop vacuum?

0:21.6

It's not hard to find.

0:22.6

Does anybody see my hair gel?

0:24.6

Tish in water, natural.

0:26.6

Quiet on the set.

0:28.6

Live in three, two.

0:34.6

Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show.

0:47.4

I'm Joe's mom's neighbor, Doug, and are you ready for some hot takes?

0:56.4

We're rounding out our estate planning and gifting week with some sizzling takes.

1:02.2

And we'll ask our panel, and you, are you in or out on these challenging options?

1:08.4

But that's not all.

1:09.8

I can't wait to hit pause on that discussion

1:12.1

because halfway through,

1:13.7

we're going to see if Paula Pan can do something

1:15.6

she's never done before.

1:17.8

String together two correct answers in a row

1:21.1

by nailing my trivia question.

1:24.6

And now, here comes a guy who's mastered the art of turning a hot summer mess into cool

1:30.8

financial wins it's joe oh saul si hi hey everybody welcome back to Stacky Benjamin's Friday edition. I am the veteran quarterback of this

1:47.2

podcast, Joe Saul, See High, just trying to get myself done back into football mode. We're getting back into

1:52.7

football mode. It's quite a generous label you've given yourself. Just that I'm a veteran

...

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