Estate planning and charitable giving might sound like snoozers, but today’s roundtable turns them into a Friday hot-takes fest. Joe calls in the Basement dream team. OG, Paula Pant from Afford Anything, and Jesse Cramer from The Best Interest. Our all-star panel goes “In or Out” on everything from writing your own will to how (and when) to give away your money.
Should you really trust an online template with your legacy? Do your kids deserve a sneak peek at the estate plan before you’re gone? And is giving during your lifetime better than waiting until the will is read? Our panel wrestles with these questions (and plenty of caveats), proving once again that nothing’s cut-and-dry when it comes to money, family, and what happens after you’re gone. Along the way, Stackers tuning in live keep the chat hopping with their own spicy opinions.
And because no Friday show is complete without a little chaos, Doug steps in with a trivia curveball about Ford’s all-electric F-150 Lightning. Will Paula shock the world with back-to-back wins? Will Jesse close the gap on OG? Or will Doug’s riddles confuse everyone into oblivion? Buckle up—this episode’s got horsepower.
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!
Our Topic: Are you in or Out on many Estate Planning Topics
During our conversation, you’ll hear us mention:
- Hiring an attorney vs DIY
- Estate planning for young adults
- Importance of beneficiaries
- Estate planning with kids
- Wills vs trusts
- Medical power of attorney
- Advanced healthcare directives
- Choosing guardians for children
- Family vs friends as guardians
- Sharing estate plans early
- Uneven vs unfair inheritances
- Preventing sibling conflicts
- Executors and trustees’ roles
- Emotional weight of inheritance
- Motivational impact of inheritances
- Warren Buffett inheritance philosophy
- Assets vs estate plan clarity
- Donor-advised funds (DAFs)
- Tax advantages of DAFs
- Charitable giving timing
- Anonymous vs public giving
- Joy of giving while alive
- Risks of waiting to give
- Encouraging others to give
- Leaving a family legacy
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Jesse Cramer

Another thanks to Jesse Cramer for joining our contributors this week! Hear more from Jesse on his show, Personal Finance for Long-Term Investors – The Best Interest, on Apple Podcasts.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
Paula Pant

Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paula on Twitter: @AffordAnything
OG

For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- How many units did the Ford F-150 Lightning sell in the first quarter of this year?
Mentioned in today’s show
Join Us on Monday!
Tune in on Monday for a fun episode when we dive into some of the most common and annoying rip-offs.
Miss our last show? Check it out here: Donor Advised Funds 101 (with Adam Nash) (SB1724).
Written by: Kevin Bailey
Episode transcript
[00:00:00] OG: 30 seconds to hear what you [00:00:02] Doug: think about flowers. Sonos. Taste. These are for the need. Some more books for these mics. Anyone [00:00:07] OG: have the promo for [00:00:08] Doug: the [00:00:08] OG: show notes? Wait, where’s the Fiji water? Is this This isn’t, is this tap water? 15 seconds. [00:00:16] Doug: Somebody get the cat. I [00:00:17] OG: can’t drink tap. [00:00:19] Doug: Can someone tell Joe Mom to stop vacuuming? [00:00:21] Doug: It’s [00:00:21] OG: not hard to find [00:00:23] Doug: my hair. [00:00:24] OG: Gelian, watered, [00:00:25] Joe: natural, quiet on the set. Live in three. Two. [00:00:37] Doug: Live from the basement of the YouTube headquarters. It’s the Stacking Benjamin Show. [00:00:51] Doug: I am Joe’s mom’s neighbor, Doug, and are you ready for some hot takes? We’re rounding out our estate planning and gifting week. With some sizzling takes and we’ll ask our panel and you, are you in or out on these challenging options. But that’s not all. I can’t wait to hit pause on that discussion because halfway through we’re gonna see if Paula Pant can do something she’s never done before. [00:01:17] Doug: String together two correct answers in a row by nailing my trivia question. And now here comes a guy who’s mastered the art of turning a hot summer mess into cool financial wins. It’s Joe Saw. See? Hi. [00:01:40] Joe: Hey everybody. Welcome back to Stacky Benjamin’s Friday edition. I am the veteran quarterback of this podcast, Joe Saul Cihi. Just trying to get myself back into football mode. We’re getting back into football mode. It’s quite a generous label. You’ve given yourself just that I’m a veteran quarterback. I think we’ve been doing this long enough. [00:02:00] Joe: If I were in the NFL, I would definitely be a veteran. [00:02:03] Doug: Yeah. To the point where you’re the guy holding the clipboard with never putting his helmet on, on the sidelines. Just, just cash it in the big paycheck. [00:02:11] Joe: He’s [00:02:11] Doug: great in the locker room. [00:02:13] Joe: And a guy who we paid double to be here today is with us. Mr. OGs here. [00:02:17] Joe: How are you man? [00:02:18] OG: Thankful that you did pay double actually, ’cause uh. College tuitions do and, uh, baby needs new shoes. So thanks. Appreciate. You know what a g screw, [00:02:26] Joe: we’re going triple today. We’ll go triple pay, gimme a little extra fold money. [00:02:30] OG: I [00:02:30] Joe: like it. A woman who’s here to negotiate for quadruple pay ’cause she’s our negotiation expert. [00:02:37] Joe: Paula, Pam from Afford Anything joins us. How are you? I am great, but what is quadruple of zero? Let’s see. [00:02:43] Paula: Four tan one. It’s infinite. Okay. [00:02:46] Joe: Five times, six times. Paula, whoa. No, it is fantastic. And the guy who works for, uh, six times, um, I don’t know, six, six times. Six times, $5, six times, $10. I’ll take anything. [00:03:05] Joe: I can kcra here, get, [00:03:06] Jesse: I’ll take anything I can get. I’ll work for peanuts. But yeah, I could see you on the sideline, Joe. I could see you on the sideline. Like directly underneath someone hoisting them into the air. Maybe a football sideline. I could see you as the base. You, you’re a bottom. You’re a power bottom cheerleader. [00:03:23] Joe: Look at me. Look at me. There it is. Yes. Sun’s out, guns out. Jesse, we are ready to go. Well, you know what guys? We have a great show today. As you can tell. Everybody’s pretty pumped. Because this is the end of our estate planning and charitable giving week, and we had a fantastic week if you missed it, Monday with attorney Tim Sel. [00:03:40] Joe: We asked him three big estate planning questions Wednesday with Adam Nash from Daffy going into, uh, donor advised funds, charitable giving and how all that works. Well, we’ve had some fun a couple times earlier this year with this concept called Are you. In or are you out? And I thought that this week we’ll have some hot takes on estate planning and charitable giving that walks through. [00:04:03] Joe: Some of the big, big answers and what I like, if you’re new to this type of thing, this inner out, uh, show. What I really like about it is all of the caveats that everybody has because as you know, it’s usually kind of a gray area, but. I like. I like, you know, let’s deal in absolutes and see what we find out as we explore estate planning and charitable giving. [00:04:26] Joe: We’re gonna do that in just a moment. We got a couple of sponsors who make sure we can keep on keeping on as we are live on YouTube. We’re gonna hear from them. And then, are you in or are you out on these hot charitable giving and estate planning concepts? [00:04:48] Joe: We record this live on a day that may or may not be Friday, and our buddy Dan in Baltimore hanging out with us says, man, I got excited and thought it was Friday for a second. Isn’t that great? You hear the Friday show and you think, but then you go, oh wait. It’s not quite Friday yet, and we’ve got Bee here with us who apparently is in Vietnam, said Good morning, Vietnam, that’s not from a movie is it? [00:05:11] Joe: May or may not be. Let’s dive in, guys. All right, let’s go ladies first. Paul Pant. We’re gonna start with you. Paula, are you in or out? You should hire an attorney instead of using a DIY online. Will, are you in. Or are you out? [00:05:30] Paula: You know, my answer is going to be, it depends on every single one of these. It can’t be, are you in or are you out? [00:05:37] Paula: All right. If I have to pick, you [00:05:39] Joe: can you have to hire an attorney or you have to DIY [00:05:42] Paula: in in hire an attorney. But, but my genuine answer is it depends. But if I must choose a side I’m in, [00:05:49] Joe: why does it depend? [00:05:51] Paula: If you are 22 years old, 18 years old, right? And you’re starting to accumulate some of your own assets for the first time, uh, but you don’t have that much and you don’t have any dependences. [00:06:02] Paula: All right. I think if you’re, if you’re 18, if you’re 22, if you’re 25, you can probably DIY one. But once things get more complicated, you have a more complicated array of assets. You have dependents who are depending on you. That’s when you want an attorney to come into the picture. But I, I wouldn’t let perfect be the enemy of good. [00:06:21] Joe: All right, well, let’s see if our other panelists agree with you. Jesse, let’s go to you. Are you in or out? Hire an attorney instead of using one of these DIY online wills [00:06:31] Jesse: I am in because I’ve seen, you know, it’s pretty frequent. I think it’s a, a higher frequency than maybe most people assume, where that real interaction with a trust and estate expert might dig up Some things that you hadn’t thought about might poke at some concerns that you have that. [00:06:48] Jesse: You hadn’t really considered before, or at the very least, it’s like the no stone unturned idea where at the very least you went through the process and you got asked all the questions and you got input from a real expert so that you know that your basic will is fine. Being basic, I think there can be times when when you DIY things like, like estate planning, there still might always be that nagging voice in the back of your head that says, I think I have a simple plan and all I need is a simple plan, and all I need is a simple will. [00:07:15] Jesse: But am I actually sure. So in my experience, taking the time and spending the little bit of extra money that it’ll take to hire a, a professional, real life attorney is going to be worthwhile. [00:07:26] Joe: Well, let’s see if this is three for three. Og, are you in or out? You should hire an attorney instead of using a DIY online Will. [00:07:34] OG: Yeah, I’m gonna make it three for three. I think when it comes to your estate planning, my cutoff is kids or no kids. People say like, well, I don’t have an estate plan. The reality is, is you do your, whatever state you live in has an estate plan for you. There’s rules that they follow, and a lot of the stuff you can accomplish on your own just by making sure that you do your own job, which is make sure the beneficiaries are correct. [00:07:57] OG: When you set up an account, make sure you put a beneficiary on your account, and if you’re, like Paula said if you’re 18 or 20 or 25 or whatever, and you know when you start that job or you start your 401k or you start your brokerage account. Just put somebody as your beneficiary and you can change it later. [00:08:13] OG: But when you have kids, that’s where all the everything changes. ’cause now you need to think about who’s gonna take care of your kids and it can’t be. The one thing I do like about the commercials that are on right now is, you know, like it shows the mom and the dad like. Talking to the aunt and going, well, so you know, if anything happens to us, you’re our choice. [00:08:31] OG: And then the guy pops up like a genie and goes, doesn’t count, you know? And he is like, you gotta put this down. You know, you gotta follow the rules. It can’t just be like, you know, this guy said, and we see so many, so many stories of places who did have a good estate plan that still get challenged and you know, all that sort of stuff. [00:08:48] OG: So listen, if you have kids, you absolutely need to have a professional estate plan done. ’cause you need to. Spell out who’s taking care of ’em, what are the parameters, how much you’re gonna pay, what you want your kids to inherit in the future, how you want it to be structured. And you can’t just do that through a beneficiary, so, uh, no kids do it yourself. [00:09:08] OG: Kids make sure that you’ve got a good estate plan. [00:09:11] Joe: Well, unless that’s Even if you have no assets. Yeah, no [00:09:14] OG: kids. And rich, yeah, you still have to do an estate plan, but you don’t have to. That’s my point. Like if you just go, I don’t wanna spend the $8,000 for an attorney. I’ll just, who, what do I care? I don’t have, there’s nobody around to get for my stuff. [00:09:27] OG: Okay, that’s fine. It’s kinda silly. [00:09:29] Joe: It’s interesting, Paula, I think there’s a lot of people think when we hear the words estate plan too, they just think that that’s a will. And yet those, those ancillary documents for people that don’t have. Assets to G’s point that still need to worry about, like, what happens to me if I am disabled and I can’t talk to my doctors? [00:09:45] Joe: Mm-hmm. [00:09:46] Paula: Right. Well, A, it could be a will or it could be a trust. And the first thing you need to do is make the decision, are you gonna have a will or a trust? And so you’ll need some level of guidance on that. And then B, to your point, Joe, who’s your medical power of attorney and what are you going to do in the case that you’re incapacitated? [00:10:01] Paula: And do you wanna sign a. DNR or not, do you have an advanced healthcare directive? These are all questions that, uh, need to be addressed. [00:10:10] Joe: Jesse, with a young one at home, was it difficult for you to decide who would be the guardian that, uh, OG ISS talking about? [00:10:16] Jesse: Yes. Yes, yes, yes, yes. [00:10:18] Joe: You just made it Doug, didn’t you? [00:10:19] Joe: That’s all you did. [00:10:20] Jesse: So Doug doesn’t know it yet, but, uh, surprise if, if we go doubt in it. Yeah. Doug, you’re moving to, you’re moving back to Rochester. No, it’s super, very hard. Very hard because. Some of the puts and takes that we had to go through is, uh, you know, we’ve got friends who we’re extremely close with, we have family members who we’re extremely close with. [00:10:41] Jesse: Some of the family is local to us. Some of the family is not local to us if it involves a grandparent for us. So, uh, one of my parents, one of our daughter’s grandparents, there’s that question of, well, they might be fit as a fiddle and able to do it right now at age 67. Are they gonna be the same way in 15 years when our daughter’s 16 and they’re 82? [00:11:01] Jesse: Do they even want the job in the first place? So many conversations, and it’s, at least for us, it was not cut and dry. I know. I know. In some cases, I actually think for my parents, it was pretty cut and dry. They knew exactly who the guardian, the named guardian would be, and it was like one 30 minute conversation. [00:11:16] Jesse: Yep, yep, yep. But for us, much, much harder. [00:11:19] Joe: Jesse, let’s stick with you for question number two, and I’d love to get, if you’re hanging out with us live on YouTube, I’d love to get you in on this too. Tell us if you’re in or out on all of these things. The second one, Jesse, is this one. Are you in or out? You should share your full estate plan with your heirs Before you die, you should share your full estate plan with your heirs before you die. [00:11:46] Joe: Are you in or out? [00:11:47] Jesse: I am in. I am in, in, in. I know it’s hard to do. I know that there probably are gonna be quarter cases where people feel like it’s just intractable and they’re not gonna wanna do it, but I think that. A lot of good comes from being open with your heirs beforehand, letting them know beforehand what’s going to happen, especially if what’s going to happen could be construed in some way as unfair or even just uneven. [00:12:10] Jesse: Maybe it’s not unfair, but it’s just uneven, and being able to explain to them why you’ve set things up, the way you’ve set them up, why certain people are going to inherit certain assets in certain amounts. Having to be able to talk through that while you’re alive is going to make things go a lot easier upon your death. [00:12:27] Jesse: Whereas if you don’t talk to them while you’re alive and they all have to find out about it after your death, there’s nothing you can do about it at that point. You can’t rewrite the documents after you die, and now you’re leaving. You’re leaving the tension to be settled between them and whoever is administering the estate. [00:12:42] Jesse: Or what’s most likely to happen is just like one of your heirs and another heir, right? The siblings are gonna fight the, the grandchildren are gonna fight. I mean, obviously that’s, I, I would think that’s something we all want to avoid, so I’m a big fan of talking about it in the open while you’re still alive. [00:12:56] Joe: I like this idea. Og, before I come to you, I really like this idea that Jesse talks about that uneven and unfair are really two different things. It doesn’t have to be, even to still be fair, you can give people different stuff and still have it be quote and frankly fair. Who cares about fair? It’s your stuff. [00:13:14] OG: I’m not as convinced on this and I can’t put my finger on the reason why, but mostly I think that if you have a good team of people who are going to administer the estate plan after you’re gone and you’ve built in the right amount of flexibility in your estate plan, then there shouldn’t be any. Like he got that and I got that. [00:13:38] OG: Maybe it’s important to have a big, broad discussion about. Estate planning and hey, we’ve taken care of it and you know, Jack’s in charge and we’ve put thoughtful things in here on purpose based on what we see or what we believe today. But the reality is, is that a lot of times you write this stuff today, you know, you write it in 2025, and then maybe you glance at it in 2035, and then you die suddenly in 2042, you know? [00:14:04] OG: And it’s like the rules that you had were for like in my case, right? I got a kid who’s 18, a kid who’s 16, and a kid who’s nine. They’re all at different levels emotionally right now. None of them are at the spot where they should be in charge of anything. You know, you could still [00:14:20] Joe: hold, hold it over the 9-year-old now though, that you could cut her out of the will. [00:14:24] OG: Oh, no, no, no. It’s the exact opposite. They all know that their sister’s getting all of it, and so they better be nice to their sister. Tell the, taught her that she’s the princess of this whole operation. [00:14:34] Joe: Sorry. [00:14:35] OG: You know, I hate these yes or no things because look, if I was 80 and my kids were 50 and you know, and I had a good sense of where they were in their life, then I would talk about it. [00:14:46] OG: My kids right now know Uncle Jordan’s in charge and, and cousin Tim, who they both know. And respect, and I’m just gonna assume that we did a good enough job of flexibility in the plan, that they’re gonna be able to, you know, make good decisions, you know, while the kids are where they are right now. [00:15:03] Joe: Well, what I like about what I like about these is that we get these nuanced decisions that have found us all. [00:15:09] Joe: Uh, kind of flesh out why we truly are in or out. As we get all of your, your opinions de Madre hanging out with us says, ow, even if you explain it, won’t necessarily fix it in the last years of your life, could be conflicted. Make sure that all the documents are easy to find. Shane says, definitely in share with a 100%. [00:15:28] Joe: Unless you’re like OG and you wanna play some dastardly games with your heirs, like make it a scavenger hunt. You think about that og. Like a OG family scavenger hunt. [00:15:37] OG: That would be pretty classy. That might happen. Uh, Dan [00:15:42] Joe: is in BZ. It felt like a limerick [00:15:43] OG: with a bunch of riddles. I’m wet when I’m dry. I am up when I’m down. [00:15:47] OG: Where am I? Where’s the, where’s the document? There’s the money. Then a big, like, you know, buried somewhere. [00:15:57] Joe: OG has always wanted to have a video where he is in the smoking jacket where he gets to say, if you’re watching this, I’m dead. You’ve always wanted that. [00:16:05] OG: I have one already. [00:16:05] Joe: All right, Paula. Uh, we’ve got one in, one out. [00:16:09] Joe: You should share your full estate plan with your heirs before you die. Are you in or out? [00:16:14] Paula: I’m in. I’m in on that one. I do think that, uh, our guest de boudreau 77 in the comments makes a very good point. You know, even if you explain it, that won’t necessarily fix it. Agree. The last years of your life could be conflicted. [00:16:28] Paula: Agree. I think those are, those are very, very good points. But in spite of that. Hearing you say it when your heirs hear you say it. There is some level of, you know, I may not agree with this, but I at least am clear that this is what the deceased, in this case, you would have wanted. I think about the TV show succession, there was lack of clarity as to what Logan, uh, Logan Roy even wanted. [00:16:57] Paula: Right? And so they were arguing about not just what the documents said, but like, what did he want? [00:17:02] Joe: It’s funny though. What about OG and his argument that, you know, he’s looking at kids that are mm-hmm. 18, 16, and nine. [00:17:09] Paula: Yeah. I guess that goes to the question of what age is a proper age to have conversations with your kids about death or about death or disease or other scary things. [00:17:22] Paula: I mean, it probably varies like there are parents. Who get a cancer diagnosis when their children are very young. And so they have to start having conversations with their kids about health and disease and death when the kids are at a very, very young age. And then there are other families where everybody’s healthy and the grandparents have lived for a very long time. [00:17:44] Paula: And so the topic of death has not never really come up. And so I think that really needs to be a case by case basis. [00:17:51] Joe: I kind of agree with what stacker Annette is talking about online here. She says there are some key people who need to know Paula. Mm-hmm. What about this idea of the key people now? Like the attorneys and the, no, like the person who’s gonna administer the state on my behalf. [00:18:06] Joe: Mm-hmm. Whether it’s your contingent trustee or your executor of your will. Yeah, absolutely. Absolutely. I mean, those people, but not the people you’re giving the money to. [00:18:15] Paula: You know, I think that. To the extent that you can share your plans and your wants and your vision with everybody. ’cause everybody is a, a stakeholder in this and they’re not gonna be able to ask you questions when you’re gone. [00:18:30] Paula: So, to the extent that you can share as much of it as possible with all of the stakeholders, I think that is, uh, better than not. [00:18:37] Joe: Oh gee. You like the idea though? I’m sure of the, uh, people that are gonna play a part in your estate, they all be up to speed on what’s gonna happen. [00:18:45] OG: Well, again, kind of where we are right now, that just makes the most sense. [00:18:48] OG: If I look at another family dynamic that I know about, there’s, you know, grandpa, there’s his kids who are all grandparents and they have varying levels of economic success, let’s say, you know, there’s a big broad brush stroke of like. One of the kids is really good financially and has very much said, this isn’t anything that I wanna be a part of. [00:19:09] OG: I don’t wanna be in charge of anything. I don’t want anything. Like, I’m good dad. Like, just leave me out of it. So I think that level of communication. Is really important because if dad in that case was like, well split it a third, a third, a third, that causes more trouble. ’cause the one kid now has to figure out how to not get it. [00:19:28] OG: You know, ’cause it, he actually doesn’t want anything to do with it. And it has nothing to do with, you know, liking it or not liking his dad. But I think in our case, the things that we’ve shared with them is they don’t have to ever worry about if they’re gonna go to school or if they have to move. Or if the house is gonna still be here and that sort of stuff. [00:19:45] OG: Like that’s all they know that that’s taken care of. They know who are the people that are gonna help take care of them, and they know those family members really well. So. I mean, I just gotta trust that those, that the trustee people, in this case, my brother, my attorney, are going to do the right thing and they’re gonna be held to the standard that they need to be held to, which is why we have the professional in there too. [00:20:07] OG: Whatever happens after that, it sounds really trite. It’s like, but I’ll be dead. You know, I remember having a conversation with somebody maybe a year ago or something about some family stuff regarding some property that this person had, you know, for a long time in the family and, and I said, is there any pressure to have to keep it. [00:20:24] OG: You just think about like generationally, right? It’s like always been the ranch or it’s always been the cottage or it’s all our stuff now it’s at this generation and, and the dad said to the kid, you know what? I actually don’t care. I’m the first one to not care like you. I’m dead, man. Like, just do whatever you think is the best thing to do with the information that you have at the time. [00:20:49] OG: And I think we get so wrapped up into. Hanging onto the emotion of what the other person who is now deceased would have be thinking about. I’ve said it in the last week, I’ve said the phrase my grandmother would be turning over in her grave if she knew dot, dot, dot, dot. I’ve said that phrase, and that’s me going, you know, I’m holding onto that emotion of the experience that I had with my grandmother around this certain topic. [00:21:15] OG: Going, oh, grandma would be so mad. It’s hard, grandma, it’s hard for five years, you know? Yeah. I mean like, like she might be looking down from above or whatever, you know, if you believe in that sort of stuff. But I also, she probably is like, I don’t care how you address your envelopes, honestly, I just tried to teach you how to do it the right way, you know? [00:21:30] OG: And it’s like, you know, anyways, long story, but we have so much attachment to. So the emotion of that stuff as opposed to looking at it from a realistic view. Practical view, yeah. Yeah. [00:21:42] Joe: John in, uh, Wisconsin says, uh, here in the chat, as somebody who received something not previously discussed at 50, I’m definitely in, as I’m still wondering what I should be doing with it now, 10 years later. [00:21:52] Joe: So leaving something to someone I’m prepared at a much more likely younger time than I was, uh, seems really wrong. Prepare, prepare, prepare. [00:22:00] OG: Well. But the other side of it too is you run the risk of lessening their. Um, what’s the word I’m looking for? Like, their drive will to work. Like, yeah. It’s like the family can kind of piece together who’s got what And like, I think that grandma’s got a million bucks and she told me I’m gonna get some of that, you know, and you had that conversation when you were 70, when she was 70 and you were 22. [00:22:25] OG: You know, and you don’t have the concept of what assisted care costs at $8,000 a month and how fast she’s burning through it. In memory care, and you’re thinking in your brain, grandma’s leaving me a million bucks. I don’t have to do anything. Well, grandma lives another 27 years. You’re 50, you’re going, well, finally, the old bat kicked off. [00:22:42] OG: I get my million bucks to find out that you get 83,000. There’s a big risk there, you know, without having. Ongoing conversations about it then? I don’t know, it just doesn’t seem like a good idea. [00:22:52] Joe: It is interesting, og I just finished, uh, as we record this, uh, the show, the Gilded Age, the current season just ended, and there’s a character Oscar who in Season Crouch one had a ton of money. [00:23:04] Joe: He was from a rich family. No spoilers. No [00:23:06] Paula: spoilers. I’m at the beginning of season two. [00:23:08] Joe: Okay, well, some bad stuff happens. Paula and I will tell you this, they, he loses a bunch of money. [00:23:14] OG: Basically. He’s broke now, [00:23:15] Joe: but when he loses that money, og, to your point, and, and Jesse, to what you were saying earlier or alluding to, I think Oscar at the end of season three is a much better human being than he was at the beginning of season one. [00:23:28] Joe: The adversity and the fact that he had to face life instead of coasting through it on money that wasn’t his. Has made him a much different character. Is that’s, that’s all I can say, Paula. Without giving, without giving, giving, giving. Besides that he dies. I mean, oh, I’m sorry. Yeah. But, uh, thrilling Season three just finished just before we recorded this episode. [00:23:51] Joe: But Jesse, I think that’s what you’re alluding to, is like, if you know I’m gonna get all this money, I mean, your thoughts around work may change substantially. [00:23:59] Jesse: Yeah. And, and in the chat, John from Wisconsin alluded to that. If there’s a good Warren Buffet quote where he talks about the money, he leaves his kids enough so that they can do anything, but not so much so they can choose to do nothing. [00:24:10] Jesse: So, I mean, granted that’s, hold on a second. He’s leaving his kids like a billion dollars. No, he’s, I think he’s leaving a mic. Is it that much? It might be. I thought it was like 10 or 15 million each. Which don’t get me wrong, it’s still a ton. Yeah. Like o obviously we’re, we’re talking about a different level of money, but there’s that idea that most of us probably wanna leave our heirs enough so that they can go out and, and do something wonderful with the money, however they choose to do it. [00:24:33] Jesse: Not so much that they lose all drive completely and and just become a couch potato, [00:24:37] Joe: but is 10 million that number? I mean, I know, I know [00:24:40] Jesse: this. This is bucket we’re talking about here, right? [00:24:42] OG: No, what I was gonna say was the reality of course, is that as you grow throughout your life. Those numbers also change. [00:24:48] OG: Sure. What you thought was a boatload of cash at 22 is pretty good. Money at 32 wouldn’t get you outta bed at 52. And at 62 is a minor annoyance because now you got a commingle, grandma’s RMDs with yours, you know? And it’s like, this sucks. I just tried to get out of this tax problem and now I got 18,000 extra dollars I need to deal with, you know? [00:25:08] OG: And it’s like 50 years ago, that was a whole bunch of money. You could buy a car and now you just wanna give, give it away so you don’t have to deal with it. There’s too much that can go wrong by telling people that they’re in it fine, what they’re getting. No. [00:25:21] Jesse: Yeah. Someone in the chat also just said that exact, I think it was Phi Lighter if I’m saying this person’s, uh, name, right? [00:25:27] Jesse: Yeah, Paul. Paul said there’s the estate plan and then there’s the estate assets, for lack of a better term, two different things, and his beneficiaries have seen the will, so they probably know to some extent maybe how the assets will be divided. They actually don’t know the scope of the assets themselves, right? [00:25:43] Jesse: Mm-hmm. 50 50 beneficiaries of a hundred thousand dollars estate is a lot different than a 50 50 beneficiary of a $10 million estate. I think that’s what Paul is alluding to there. [00:25:52] Joe: That’s the, uh, Jesse, I’m contingent trustee for a family member. And that’s the state that I’m in, is that I know how it’s all being. [00:26:00] Joe: I know what I’m supposed to do. Mm-hmm. I know where everything is, but I don’t know what everything means. I have no idea the scope of the project. I don’t know all of that. So he’s decided to be private About how much. But in terms of where the estate plan is and what to follow, like that is all crystal clear what my job is the second that something happens, uh, to this family member. [00:26:21] Joe: Alright, we’re going to talk about charitable giving in the second half of this and gift giving in the second half. Can’t wait for that piece of the discussion, but at halfway through our Friday show. We have this incredible, incredible trivia challenge of which the Paula pant actually scored a point last week, and we’re still a week later. [00:26:41] Joe: Like, I’ve got goosebumps. Paula, I don’t know about you, but I’m, I don’t know what’s going on there, but I think Doug nailed it at the beginning of today’s show. If you can go two in a row, that’d be amazing. [00:26:50] Paula: Wow. If there was a betting market on this show. Imagine the payout. If anybody were to take that bet and win, I think [00:26:57] Joe: it’d be a huge payout. [00:26:57] Joe: ’cause nobody’s betting you’re gonna do it. [00:26:59] Paula: Exactly. [00:27:00] Doug: Well, no worries there. ’cause Paula is still the dark horse with six and a half points. Jesse, two points ahead of her, two whole horse lengths ahead of her at eight and a half. An OG leading the pack with 11, but we have a little bit of a race going on. A little bit of a race we do. [00:27:17] Doug: All right, Doug, what’s on tap, man? [00:27:23] Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and here’s a big day in history. Back in 1902, Henry Ford finished a dispute with his investors by leaving his own company. He took his name. 900 bucks in his favorite mix tape and started the Ford Motor Company a year later. However, it was on today’s day in history that those investors renamed the operation old Hank Ford left behind as the Cadillac Automotive Company. [00:27:54] Doug: Crazy, huh? Of course, they named the new company after the line of the Billy Joel song. He’s trading in a Chevy for a Cadillac Q out of know by now. Is that the way it worked? No, it’s not. It’s not. It sounds true. It’s probably true. Anyhow, more recently. Ford went on to create an electric truck called the F-150 Lightning. [00:28:16] Doug: It took a while, but during the first quarter of this year, the lightning took over the number one spot in the USA’s electric truck category. So here’s today’s question. How many units did the Ford F-150 Lightning sell in the first quarter of this year to claim the number one spot? I’ll be back right after I go look up where the name Cadillac actually came from. [00:28:40] Doug: Maybe it was like an acronym or something. Uh, cars and donuts in lanes. All classy that, that, that works. Probably that. [00:28:56] Joe: Maybe, right? I think I missed an hour there. I’m sure there’s some, I’m sure there’s some truth there. All right. Og, give us the truth. How many cars? The Ford F-150 Lightning. How many they sell? First quarter of 2025. [00:29:10] OG: Something makes me think that the new car market is in the nine to $12 million a year range. [00:29:19] OG: So that’s in the three-ish million a quarter. It’s like new car deliveries. So two and a half to three. What percent of all car new cars are trucks? Maybe 40%. So that would be a million Ford’s, number one. But there’s how many other brands? Maybe five. Realistic. Well. You said it’s electric trucks? [00:29:48] Joe: Yes, electric trucks. [00:29:49] OG: How many did they sell to be the leader of electric trucks? Not trucks. Trucks. Be the leader [00:29:53] Joe: of el? No, just electric trucks. [00:29:56] OG: Okay. [00:29:57] Joe: Which is a tiny percentage of all trucks sold. [00:30:01] OG: Indeed. Indeed. [00:30:02] Joe: Hey, hey, hey, Joe. Shut it, it just [00:30:07] OG: is, I’m just wor I’m working through it. I’d have got there, um, I, somebody [00:30:11] Joe: alert the pressed that they don’t sell nearly as many electric drugs. [00:30:15] Joe: Who knew out there in the back 40 past your, your, your stringing up that electrical cord all the way to the back acreage in Wyoming. Yeah. [00:30:23] OG: Yeah, F1 fifties are the number one truck for like 50 years or something almost now. So long time. Um, alright, so there’s, uh, 10 million trucks, two and a half million or 10, 10 million cars. [00:30:33] OG: Two and a half million a quarter. Let’s say 40% of that’s a million Ford controls, you know, uh, let’s say, uh, 40% of that’s 400,000. Um, I’m gonna say that they sold in the first quarter. I’ll just make it simple here. They sold 50,000. Lightning. F1 fifties in Q1. [00:30:54] Doug: 50,000. Boy. Thanks for making that simple, og. [00:30:58] OG: You’re welcome [00:30:59] Doug: buddy. [00:31:00] OG: Jesse, what do you think about 50? Sorry. 49,000? Nope. Uh, 862. [00:31:04] Jesse: So the sun is 93 million miles away. That’s right. And, uh, 1400 watts per meter squared. Solar panels cuff, uh, I’m gonna guess, uh, I’ve got my notes here. I was kind of jotting down some notes thinking about, you know. I was writing as OG was talking and uh, but my notes are much shorter. [00:31:25] Jesse: I’m gonna go lower. I’m gonna go, uh, uh, 22,000 being born on March 22nd. I’m gonna go 22,000 units in the quarter. [00:31:34] Joe: Wow. Big old field go there. Paula, you got 50,000 electric trucks. 22,000. Electric trucks. What’s your electrifying answer? [00:31:45] Paula: Oof. Okay. Well, let’s see. So dinosaurs roam the earth 165. No, was it 65 million years ago? [00:31:52] Paula: Yeah, it was 65 million. And then they, but the dinosaurs existed for like, what wasn’t it over a hundred million years. So I’m gonna go with, [00:32:02] Joe: wait a minute, Paula, before you guess. [00:32:04] Paula: Yeah. [00:32:04] Joe: A friend of mine, Robert, uh, shared with me a bumper sticker that he saw recently that said, uh, this car runs on renewable dinosaurs. [00:32:16] Joe: Or recycled dinosaurs. They’re not very renewable. God, I can recycled, I can blow a punchline better than anybody. They’re probably not renewing them, are they? [00:32:24] Paula: It’s all, you know, it becomes carbon and the carbon becomes Yes. Yeah. They, [00:32:28] Joe: but it is, but it is recycled dinosaurs that they, yeah, they, they, [00:32:31] Paula: they disintegrate into the earth and it’s a circle of life. [00:32:33] Paula: And then Elton Johnson sings a song about it and. You know, and then it [00:32:36] Joe: comes back again. [00:32:37] Paula: Yeah. Yeah. It’s all carbon and oxygen and, you know, various other elements [00:32:41] Joe: in the end. Are you saying the circle life all ends in Elton John’s bank account? [00:32:46] Paula: No, no, no, because eventually the bank account, uh, withers and falls into the ground, and then it gets [00:32:53] Joe: That’s somebody else. [00:32:54] Paula: Exactly, exactly. Say a number. All right. What’s your guess? I’m gonna take the over 50,001, [00:33:01] Joe: 50,000. I, I think it’s gotta be 49,863, right? Oh, okay. [00:33:06] Paula: Yes. Uh, if, if OGs guest was No. Was OGs? No. We’re going [00:33:10] Doug: with 50 K for OGs. First guest was 50 K. That’s what we, I’ve already done the math. We’re not revising that. [00:33:16] Joe: I think that’s why he wanted og. [00:33:19] Joe: Gotta do a better job next time of saying a number with two decimals. I will, yeah. All right. Paula’s got 50,001. OGs got 50,000. Jesse. 22,000. Who’s gonna win this? We’ll find out. A user online is putting a hundred dollars on you, Paula. So [00:33:35] Paula: let’s see. Whoa. Oh, here we go. That’s, that’s a lot of responsibility. [00:33:39] Jesse: Woo. I’ll take that bet. [00:33:43] Joe: All right, og, you kicked this off with, uh, 50,000, uh, feeling pretty good. [00:33:49] OG: No. The first stamp thing about electric vehicles, let alone electric Ford vehicles, [00:33:55] Joe: Jesse, 22,000. You feeling better than og? [00:33:58] OG: Yes. [00:34:00] Joe: Oh, oh, he feels, feels very good. Well, I just, [00:34:03] Jesse: I, I’m not positive. I think the number’s lower than I, I, I’m, I’m glad I’m on the under. [00:34:09] Jesse: That’s all. I gut instinct is I’m glad I’m on the under. [00:34:12] Joe: You’re glad you’re the bottom. Yeah. You were making me the bottom earlier. Now you’re the bottom. [00:34:15] Jesse: I’m worried about the field goal, but I’m, I’m happy being on the bottom right now. [00:34:20] Joe: And Paula, you [00:34:20] Paula: got the top 50,001. I mean, there’s a wide range, like the range is 50,001 through Infinity, so I, I certainly have the, the bulk of the numerical system. [00:34:32] Joe: All right. Is user online getting a hundred bucks? Is Paula gonna go two in a row? Doug, what’s our answer man? [00:34:42] Doug: Well, hey there stackers. I’m human Voltage meter ’cause I’ll stick my fingers in anything. And Guy who shockingly isn’t an electrician, Joe’s mom’s neighbor, Doug, shockingly, it turns to see what I did there. It turns out the Cadillac Motor Company, weirdly enough, was named after French Explorer. Antoine de Lamo Cadillac. [00:35:02] Doug: He did a bunch of nothing according to his mom, except created the incredibly badass city of Detroit in 1701. Though today we are talking about the company form just a few years later in Motown Ford Motor, specifically their F-150 Lightning electric truck, which took over the number one spot in the division earlier this year. [00:35:24] Doug: So how many units did they sell in the first three months of 2025? But what I can say is this, it was 40 2088 units less than what Paul guessed. 40 2087. Less than what? Og Oh man. Guessed. And just 14,087. Less than what Jesse guessed, because the correct answer is 7,913, meaning Jesse is getting closer to that lead. [00:35:52] Paula: Wow. This is getting to be a, a close competition between the two of you. I’m liking this. I’m liking it. [00:35:59] Joe: Paul was like, I’m gonna assume the spectator role. Yes. Paula likes to watch [00:36:05] Jesse: Doug. What was that French guy’s middle name? Uh, di DMO Duff. I thought you said that. Dmu. Interesting, interesting name. [00:36:13] Joe: M-O-T-H-E. [00:36:14] Jesse: Yeah. Oh, MOT. Okay, got it, got it, got it. M-O-T-H-E. I was hearing MUFF. MUFF is what I was hearing. Lam. [00:36:23] Joe: Congratulations, Jesse. Now it nine and a half points. Wow. [00:36:27] Jesse: There we go. [00:36:28] Joe: Almost striking distance almost. We’re coming down the home stretch. Things are tight. We got four and a half months to go, so we shall see. [00:36:35] Joe: But. Let’s get back to our original game, which this time is called In or Out. We’re gonna shift our focus now from our Monday topic, which was when Tim sro attorney Tim SRO joined us and we asked him estate planning questions to when Adam Nash, uh, CEO of Daffy was here, and let’s talk about charitable giving. [00:36:58] Joe: Og, I don’t think we started with you last time, so we’re gonna start with you, og. Are you in or out? Anonymous. Giving should be avoided, so others are encouraged to give. You know how you always see those given anonymously? Are you in or out that that should be avoided? [00:37:18] OG: Well, how vain are you? [00:37:21] Joe: Well, I think the point here is that people see that you gave, they’re more likely to give. [00:37:26] OG: But generally speaking, the anonymous gifts aren’t the a hundred dollars ones. They’re the a hundred thousand dollars ones, right? I mean, I know that there are some, but I would venture to say proportionately, the anonymous ones are the ones with commas and lots of zeros, not necessarily the ones that don’t have commas and very few zeros. [00:37:43] OG: So if you’re trying to influence other people, I think it’s totally fine to. To not be anonymous. Is that, I don’t know if that was your question or not. I know that in the charitable donation world, foundations and the like, let’s say that it’s a specific organization, like maybe it’s the using Ford as an example. [00:38:07] OG: Maybe Ford has a charitable arm or something. Right. One of the things that makes them attractive from a charitable standpoint for other places to give money to Ford is the percentage of employees who give to the Ford Charitable Foundation. So if there was one, I’m just making that up, or the Harvard one or you know, insert whatever group here. [00:38:28] OG: One of the questions that third party donors would ask a charitable foundation or a charitable fund is what percent of your own people are doing this? You want that number to be really high. So if you give anonymously, they can’t track that. You know, all of the third graders parents contributed to the school fund. [00:38:46] OG: They just know that some people gave some money. So it is important from a charitable fund standpoint to, to make your donation, uh, public. Now, what you could choose to do is actually do both. Let’s say that you are one of those people that are fortunate to be able to donate a bunch of money to, you know, whatever, but you don’t have the vanity attached to it. [00:39:07] OG: Why don’t you give $500 so that everybody can see that you donated and $49,500 anonymously. You still do what you wanna do without having to draw the attention of like, well, Joe’s family must be doing good. Look at how much money they just gave the symphony la la. [00:39:25] Joe: So just given the question as written here, anonymous giving should be avoided, so others are encouraged to give it. [00:39:31] Joe: It sounds like you’re out [00:39:32] OG: anonymous gi, there’s so many negatives in this question that should be avoided. [00:39:36] Joe: Should be avoided, [00:39:37] OG: so you definitely shouldn’t do it. [00:39:39] Joe: You’re saying go ahead and give. Go ahead and give anonymously if you want, which would mean you’re out. No, it should be avoided. That’s not what I’m saying. [00:39:47] OG: I’m saying that you should give money publicly, but a smaller amount. So the answer is, so you could check the box that says you’re in, you know, the electrical department at Ford has a hundred percent participation, and that’s a big deal. Do [00:40:01] Joe: you agree with this statement then anonymous giving should be avoided. [00:40:05] OG: Yes, yes, he is in asterisk. Unless you have a whole bunch of money you wanna give away and don’t want to like, let everybody know that you’re rich. [00:40:13] Joe: It’s the asterisk that are the fun part of this for me, but I get it. Paula Anonymous giving should be avoided. So others are encouraged to give you enter out. [00:40:21] Joe: I am [00:40:21] Paula: out. I’m out on this one. [00:40:23] Joe: Oh, [00:40:24] Paula: I think giving is, giving. Giving is, giving is giving. And whatever can happen to encourage people to give. Should absolutely be encouraged if anonymous giving is the thing that encourages you to give, to give more, to give greater volumes of money, or to give with more frequency, greater frequency, anything that encourages giving. [00:40:43] Paula: I’m in for [00:40:45] Joe: Jesse. How about you? [00:40:47] Jesse: Yeah, I’m of the mind that just give, like, I’ve got a little bit of a who cares? Like who cares? Give how you wanna give, uh, if you wanna give anonymously to shield your identity to prevent other people knowing from your. Asset base. Great. That’s fine. If you wanna give so that you can see your name on a brick or you can see your name on a building because you like og, just started with, you know, how vain are you? [00:41:08] Jesse: I mean, to some extent it’s like, right, if you wanna see your name up there or you want your heirs to see your name up there, fine. Go. Go right ahead. Uh, I’m not really sure I have a preference. Um, and I don’t know enough to know if there’s that psychological. Proof that by you attaching your name to something, you’re gonna influence more people to do it. [00:41:26] Jesse: I mean, around here, if, if I donated a, a big sum of money and said, Jesse Kramer made this donation, I bet you it would drive other donors away. So I’m, I’m not sure. I’m not sure that benefit is there, so I don’t know if that makes me in or out. Joe, you, you might have to tell me with the whole. Does that make me in or out? [00:41:43] Joe: That makes you out because I’m out. Y no, wait a minute. You should avoid anonymous giving. The The answer is you’re out on that. So many [00:41:52] OG: negatives. [00:41:52] Joe: You’re out. Paul is out. Oh Jesus. This is a [00:41:54] Paula: confusing double negative. It’s like, so you’re out. You should avoid it for sure. [00:41:58] OG: Not gonna do it. You’re [00:41:59] Paula: out. That it should be avoided. [00:42:01] Paula: So you’re in that. It shouldn’t not be avoided. All, all you gotta do, [00:42:04] Joe: all you gotta do, Paula is just listen to the question and say, do I agree with that? You should avoid anonymous giving. Are you in or out? You should avoid anonymous giving. [00:42:12] Paula: I, I’m out. [00:42:14] Joe: Yes, you are out and OGs in and [00:42:18] Jesse: I’m gonna say yes or no from now on. [00:42:20] Jesse: Right. I’m trying to think of the opposites too. If the statement was you should give anonymously, I would be out because I don’t care how you give, you would say no. [00:42:30] Joe: I think Dan online, uh, hanging out with us on YouTube sums it up perfectly. He says he’s not, not in. Exactly. [00:42:39] Joe: All right. Question number two, coming down the home stretch here, Paula. Mm-hmm. Are you in or out? You should give during your lifetime. Still waiting until you die. [00:42:53] Paula: Hmm. I mean, my answer is you should do both. So I guess strictly speaking, I am in, because the question does not say you should only give during your lifetime. [00:43:02] Paula: Let’s [00:43:02] Joe: say you’re choosing just one asset today, and you have to choose, do I give it now or do I wait till later? Which one’s your preference? [00:43:10] Paula: I’d rather give during my lifetime. [00:43:12] Joe: Okay. Yeah. So the answer is you’re in. Yeah. Jesse, how about you? [00:43:16] Jesse: Yeah, I’m in for reasons of, uh, just anecdotes that I’ve heard and, and you know, stuff that I’ve heard from, from my audience or people I talk with, and even for some personal reasons of like inter, you know, within my family where I’ve seen that a good amount of joy comes from giving away some of your assets during life. [00:43:33] Jesse: Seeing your heirs put them to use. Uh, I think that’s a die with zero concept that, you know, it’s not like Bill Perkins invented it, but I think it’s a seminal part of his message. Even something as simple as like a little personal anecdote is that my brothers and I went on a, a hike a couple weekends ago and our dad was kind of asking us some of the details, you know, where, where are you staying and how are you doing this? [00:43:53] Jesse: And it was a really frugal hike because we got free, you know, a, a friend gave us free accommodations and blah, blah, blah, blah, blah. And I was like, yeah, it’s gonna be like a few hundred bucks. It’s gonna be gas and groceries, and that’s it. My dad was like, I’ll, I’ll pay for it. I’ll pay for it. Like it’s a family trip. [00:44:06] Jesse: You boys are going to spend family time. And I could tell in his kind of stoic way, I think it brought him satisfaction to give some money away to us, even in those simple, simple ways. I think, uh, giving it away while you’re alive is on net better than giving it away after you die. [00:44:21] Joe: Di di Dividend is, uh, commenting, uh, this segment’s stressing me out. [00:44:28] Joe: It’s not stressing him in, not that that’s right. Yes, he is out. I’m being stressed in og Give during your lifetime. [00:44:35] OG: Um, yeah. I mean, if you’re, in both circumstances, if you’re thinking about it from the context of some charitable organization or something like that, and or if you’re thinking about it from the perspective of. [00:44:46] OG: I’m forecast to have an estate of $4 million when I’m a hundred years old, and that’s gonna go to my kids. Well, maybe they’d be, you know, have greater utility out of it at 40 with 250 K right now, and you die with an estate of two and a half million instead of four because you, you know, were able to help ’em buy a house or something like that. [00:45:04] OG: So yeah, I would, I would say in both circumstances. [00:45:08] Joe: Uh, diva makes a, a nice comment here. I inherit to 65 not worth much. Maybe better when people are younger, I think is kinda the point there. And Jesse, I agree with something that you said earlier, which is also there’s this joy in you seeing them. Use it. [00:45:23] Joe: I mean, mm-hmm. You can get joy during your lifetime watching people make good use of money that you’re not going to spend or maybe, you know, do something together with it. I don’t know. Alright. Last person. Who has it gone first this round? I think we had Paula go first. OG went first. I think, Jesse, that does leave you Last question for today’s show and that is this, I know we had Adam on on Wednesday, but I wanna get your take on this. [00:45:48] Joe: You in or out? You should use a donor advise fund to manage your giving. Are you in or out? [00:45:56] Jesse: Oh, Joe. Uh, black and white. Huh? Very black and white. I’m gonna say out. And the reason why is because I think that answer applies to the most people out there who give charitably. I’m on the board of a nonprofit and I know at least for us. [00:46:18] Jesse: The overwhelming majority of our individual donations are the 50, $7,500 amounts, and if that’s the amount that you’re giving, even if you give a thousand dollars a year spread, you know, a hundred dollars at a time to 10 different organizations, I’m pretty sure that’s too small to get any sort of benefit from the use of a donor-advised fund. [00:46:37] Jesse: It’s only when you get into much, much bigger numbers in terms of donations and, and you know, you’ve got appreciated stock going in and out like that. Those are the situations where I think donor-advised funds start to make more sense. Happy to be wrong on that by the way, but, uh, based on that understanding, I am out on your statement. [00:46:55] Joe: Og, how about you? You should use a donor-advised fund to manage your giving. [00:46:59] OG: Well, I’m just glad that Jesse’s happy to be wrong because he’s wrong. Please tell me, educate me. No, I mean, the reality is, is that it’s so much simpler, you know, back up 10 years or even five years ago, and yeah, it’s like unnecessary. [00:47:15] OG: But now honestly, if you have any non-qualified money in your net worth, any sort of position, you’ve got a mutual fund, an ETF, A stock. You have any of that, you should always give that to your donor-advised fund and put cash into your brokerage account that would be equal to your donation. So in Jesse, in your case, you say, well, it’s a thousand bucks and I was gonna split it up a hundred different ways or 10 different ways. [00:47:39] OG: It’s just not worth it. I would say it is worth it. You have to earn 1200 bucks to donate a thousand, or you can take a thousand dollars outta your brokerage account and not pay any taxes on that. Put it into your donor advised fund and donate it as you see fit. Secondarily, as you get to that spot, first of all, you’re building that muscle, but as you get to the spot where sometimes those donations add up and you know, maybe you’re able to pull forward a bunch of stuff in one year and that sort of thing. [00:48:06] OG: Mm-hmm. You have one line item on your taxes. Yeah. The donation occurs from a tax standpoint when you put it in the donor-advised fund, not when you send it to the Girl Scouts, into the Boy Scouts, into whatever. Like, that’s just a secondary thing. So if you say, oh. You know, every month I’m gonna take a hundred dollars outta my brokerage account of my most highly appreciated thing that month and put it in my donor-advised fund. [00:48:27] OG: At the end of the year, you get one statement that says You put a thousand bucks here. Done. Now I know a thousand dollars doesn’t get you anything on your tax return right now, but a it might someday in the future. And nevertheless, it’s just super easy to, super easy to keep track of. So yeah, you should never donate cash if you have a brokerage account. [00:48:45] OG: You should never donate cash to anything. I [00:48:48] Jesse: think I agree with everything you just said. It’s just a matter of, I don’t think most people have a taxable brokerage account, and I don’t think most people ever donate, would ever put enough money into a donor-advised fund to itemize that year’s tax bill. If we’re talking about stackers, people who are self-selecting to listen to finance podcasts, you’re probably right. [00:49:08] Jesse: That is different. And if we’re talking about the people out there who have highly appreciated assets. To put into a donor-advised fund. Of course that changes the conversation. [00:49:16] OG: I just think, you know, it goes back to donate during your life or later you can make a bigger impact, especially if you’re young and not really deciding what’s super important to you yet. [00:49:27] OG: You know, what’s what’s become important to me in my late forties is a lot different than even just 10 years ago, and is certainly a lot different than my perspective on things in my twenties. And if I would’ve continued the same contribution level, if it’s a percentage number or if it’s a dollar amount, just said, okay, I’m not entirely sure what I wanna do with this yet, but I know I want to build the muscle of. [00:49:48] OG: Giving. And so I’m going to, you know, I’m always gonna put 3% of my income in my donor-advised fund. That money sits there and it grows, it does its thing and then I can, I can make a large donation to a thing that really matters to me later on. So I think it’s just a good place, especially ’cause it’s easier to manage now. [00:50:05] OG: It’s super low cost. I know that there’s a cost at Schwab and Fidelity, but it’s still low-ish cost. It’s just a good bucket to have one line item that goes, this is my charitable money. And then when you find something that excites you, you just go online, you type it in, they mail a check, and off you go. [00:50:20] Joe: Paul, let’s bring you into this. You should use the donor advice fund to manage your giving or you in or out? [00:50:26] Paula: I am in. So I am in for all of the reasons that OG just said. And in addition to that, the two other points that I wanna make, one is that you, you can give away very small amounts. Uh, one of the people in chat, uh, was it Phi? [00:50:39] Paula: Yeah, Phi Lidar in chat said the donor-advised fund at Fidelity allows for $50 grants. My donor-advised fund is at Schwab, and I don’t know if they have a specific minimum, but I know that in the past I have given away like a hundred bucks, 200 bucks out of there, and that’s not been a problem. So even giving very, very small amounts, you can easily do it from a donor advised fund. [00:51:03] Paula: So, A, there’s all of the reasons that OG just said, but b, I think one of the other biggest reasons for me is. Just from a budgeting perspective and like from a mental bucketing perspective, having a singular bucket of money that mentally and literally you can say, this is my charitable giving money. It just makes the budgeting element and the bucketing element so much easier. [00:51:27] Joe: I agree with everything both you, Paula and OG said, and obviously we had Adam on the show on Wednesday, uh, from Daffy doing a deep dive on, on how these things work. And so I love the idea of them. But I’m gonna, we’re gonna go two and two, two ins and two outs because Jesse, I’m with you, but for a different reason. [00:51:47] Joe: And the reason is knowing a lot of people who run these wonderful organizations that need support. And this, Jesse, you, you brought up a little bit of this. There is so much money sitting in donor-advised funds that is yet given. And I think the fact OG, about what you said about the fact that we get the tax break when we put the money in and then actually giving the money is a separate thing later when something excites me. [00:52:13] Joe: Well the bad news is I feel like we go after the tax break and then we just sit on it. ’cause there’s, in 2023, which is the, the most recent data that I have, 54.77 billion, billion dollars. Sitting in donor-advised funds that haven’t been given yet to any charitable organization. And when you talk to these heads of these great organizations, they’re like, we need help now. [00:52:35] Joe: And people are just sitting on huge sums of money. Some people not making a decision ’cause all they’re in it for is, is the tax breaks. So while I agree with everything and we’ll see both, uh, both OGs and Paula’s points, if you could have a donor-advised fund and make sure the money gets given, great. Do that, but the amount that’s sitting in these things is, is really not helping, I think what it was intended to help. [00:53:00] Joe: Interesting thing to me. Donor-advised funds, let’s end this show. With finding out what amazing stuff you guys are all doing. By the way, I want to thank everyone on YouTube hanging out with us for the exciting chat today. You guys really showed up. Nice, nice work. And thanks to our contributors for a fantastic end to our charitable giving and estate planning week. [00:53:21] Joe: You know what’s funny, Doug, is that. You plan a week like this and, and it just sounds like such a snoozer, estate planning and charitable giving, and yet the community always shows up and everybody’s so happy to chat about this stuff. It really was a great week and hopefully we give to a lot of great organizations and get our estate plan done, dammit, but. [00:53:40] Joe: After you’re done or maybe before you’re done with your estate plan, you can hit pause and find out what’s going on in the Afford Anything show what’s going on, afford anything. [00:53:47] Paula: Paula on the Afford Anything podcast, we have an interview with Lori Rosen Cough. She’s a professor of management at Wharton and she talks about all of the various forms of entrepreneurship. [00:53:57] Paula: So there are people who are bootstrappers, there are people who are. Trying to develop a, you know, the unicorn. There are people who are funders. There are all of these different varieties of entrepreneurs, different flavors, black marketers. So she walks through that framework. [00:54:11] Joe: Black marketers, I mean, it’s real. [00:54:15] Joe: I don’t, did black marketers make her list? Paula? The, the what? Marketers? Black market. You know, the black market? [00:54:21] Paula: Ah, oh yeah. Like the underground. Yes. Yeah, yeah, yeah. [00:54:26] Joe: Yes. No, [00:54:27] Paula: no. I I believe that she was only discussing legal types of, uh, missing [00:54:32] Doug: out. You’re missing out on a very lucrative avenue. [00:54:35] Joe: Strongly considered, especially Doug, if your favorite color’s orange, it’s fantastic. [00:54:40] Joe: But entrepreneurship showing up front and center at the Afford Anything podcast. Yes. Yes. That’s with Lori Rosen. Lori Rosenau, og, what are you doing? This fine Midgut weekend? [00:54:52] OG: Is it this weekend or next weekend? [00:54:53] Joe: This is, uh, the 22nd. [00:54:56] OG: Oh. Well in that case I have already dropped my kid off at college, so we are down to two to go. [00:55:02] OG: Who’s counting [00:55:06] Joe: spoken with so much empathy and, and heart? Uh, Jesse Kramer, what’s going on at the Personal Finance for Long-Term Investors Podcast? [00:55:15] Jesse: Well, I, I feel like I might have to publish a Ask Me Anything episode with donor advised funds. I’m still seeing some great comments coming here through the livestream chat. [00:55:23] Jesse: And, uh, it’s a little gray. It’s a little gray. I’ve got an episode coming up, speaking of random ramblings, like the one I just went on. I’ve got an episode coming up and the working title is Jesse’s Random Ramblings. But, uh, long story short, I talk about some controversial and or contrarian takes that I have, uh, from the personal finance and financial planning and investing world. [00:55:42] Jesse: So that’ll be a fun episode, stuff that you’re out on. Exactly. That’s exactly right. What a segue, Joe, you’ve been doing this for a while, huh? [00:55:50] Joe: It’s, I’m, I’m a veteran. I’m the veteran quarterback of this podcast. You’re, you’re the [00:55:53] Jesse: power bottom of this podcast. That’s right. [00:55:56] Joe: I did say power bottom. I’m going with veteran quarterback. [00:55:58] Joe: But your, your terminology may differ. Alright everybody, thanks a lot for hanging out. If you know somebody who is thinking about how do I gift better or how do I set up my estate plan, maybe they need to set up their estate plan. Go back to Monday, show with Tim Sil, or Wednesday show with uh, Adam Nash, or today’s in or Out. [00:56:17] Joe: Refer this week to ’em. ’cause I think we just wrapped up a great week on those topics. But the way we wrap it up officially is with Doug telling us what are the things that are on our to-do list today. [00:56:27] Doug: Well, Joe first take some advice from Jesse. Uneven is not the same as unfair. Look, if you wanna give less to one of your sons ’cause he had bad aim in the bathroom, look, that’s up to you. [00:56:38] Doug: Second, don’t forget what OG said about giving while you’re alive. You should not not do it if you don’t wanna see people not be happy. I think that’s what he said, but the big lesson. Forget a will. I’m leaving my estate to the guy who can beat me at Mario Kart. Good luck kids. Sorry. [00:57:02] Doug: Thanks to the Jesse Grammer for joining us today. You’ll find the personal finance for Long-Term Investors podcast wherever you are listening to us now. Literally, oh, you’re at the grocery store. It’s next to the giant tub of bean dip. You’re at Home Depot. It’s in aisle five, just below the big knockers. [00:57:20] Doug: What? The door knockers. You confused. Don’t worry. It’s always on the device that you are listening to right now. No matter what aisle you’re in, you know what? We’ll also include links in our show notes at Stacking Benjamins dot com. I really wanted to say, speaking of big knockers, but I probably shouldn’t say that. [00:57:41] Doug: Can I say that? Go. I wanna say it. I still want to say it. Go for it. Speaking of big. Door knockers, thanks to Paula Pant for hanging out with us today. You’ll find her fabulous podcast. Afford anything wherever you listen to finer podcasts. I did it. I said it. Oh God. Thanks also to OG for joining us today. [00:58:03] Doug: Looking for good financial planning. Help head to Stacking Benjamins dot com slash OG for his calendar. This show is the property of SP podcast LLC, copyright 2025 and is created by Joe Saul Sea Hive. Joe gets help from a few of our neighborhood friends. You’ll find out about our awesome team at Stacking Benjamins dot com along with the show notes and how you can find us on YouTube and all the usual social media spots. [00:58:29] Doug: Come say hello. Oh yeah, and before I go, not only should you not take advice from these nerds. Don’t take advice from people you don’t know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s Mom’s neighbor, Duggan. We’ll see you next time back here at the Stacking Benjamin Show.I.
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