Money Ideas That Sound Great Until You Read the Fine Print (SB1905)

Bigger returns. Guaranteed income for life. Retiring five years early. Every one of these sounds like an obvious yes, until you see the invoice that comes with it. Joe puts Doc G, OG, and Jesse Cramer through a rapid-fire "in or out" game: he pitches five genuinely appealing financial ideas, and each of them has to decide whether they'd actually take the deal, and name the worst realistic thing that could go wrong if they did. What You'll Walk Away With Why leveraged ETFs have historically wiped out the vast majority of investors who hold them for more than a few yearsThe real, academically-supported case for and against thematic and "beat the market" investment fundsA clear framework for handling a single stock that's grown into 40% of your portfolio, including a simple trick for spreading a big tax bill across two tax yearsWhy "guaranteed income for life" almost always means giving up the one thing that actually protects you from inflation over a multi-decade retirementA genuinely helpful explanation of what a Monte Carlo simulation's "80% success rate" actually means, and why it's not the cliff-edge failure people assumeWhy retiring five years earlier isn't automatically the right move, even when the math technically worksA real cost-benefit gut check on working an extra year or two specifically to fully fund a child's college education Why This Matters Now The financial products and strategies that sound the most appealing, guaranteed income, market-beating returns, an earlier retirement, all have a cost that isn't obvious from the pitch alone. That cost isn't always dishonest or hidden on purpose, but it only becomes clear once you ask the right follow-up questions. Learning to instinctively look for that fine print, what you're giving up, what could go wrong, and whether the tradeoff actually serves your specific goals, is a far more useful skill than knowing the name of any single financial product. From the Basement A three-way tie atomizes the year-long trivia standings heading into the fourth quarter, decided by a question about how little Charles Schulz was paid for the very first month of Peanuts comic strips. Resources Mentioned Earn & Invest podcast https://earnandinvest.com — Doc G's showPersonal Finance for Long-Term Investors podcast https://bestinterest.blog/personal-finance-for-long-term-investors/ — Jesse Cramer's showGranola https://granola.ai/sb — AI-powered meeting notes tool mentioned in the sponsor breakStacking Benjamins on OG's calendar https://stackingbenjamins.com/og — for financial planning help See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

• 0:00Speaker 00

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• 0:29Speaker 01

  My God, the Dukes are going to corner the entire frozen orange juice market.

• 0:40Speaker 02

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

• 0:55Speaker 02

  I'm Joe's mom's neighbor Doug, and on today's show, what are some money concepts that sound great until you hear the catch? Our team is bringing some of the whoppers lots of people fall for as Joe asks them, are you in or out on these money ideas? But that's not all. Here's the best idea ever. How about we continue our epic game show year with another dose of my weekly trivia contest? We're into Q4 and our contributors are neck and neck. And now a guy who is up to his neck in dad jokes, it's Joe Saul CI.

• 1:36Speaker 03

  Hey there, stackers. Who doesn't like a good dad joke, Doug? Happy Friday to you. We're super happy that you're here, if you're here live with us, hanging on on YouTube, making the show. Either way, it's going to be a super hour because we are talking about these financial concepts. You know, it's funny, I was talking to a creator, I was just recently at an industry conference called FinCon, and this creator was talking about one of the best things to do when you're creating stuff to go viral online, right? That everybody wants to see is to take the thing that everybody says they want, the thing that they think that they need, and then tell them they can have it, right? Just tell them, hey, guess what? This thing that you didn't think you could do, you can have it.

• 2:19Speaker 03

  Well, today we're going to talk about what could possibly go wrong when you do that. One thing that of course is never going wrong is hanging out with Doug. What's up, man?

• 2:30Speaker 02

  I'm feeling all right, Joe. I'm probably feeling the same way as one of my burritos when I make them myself, just held together by hope at this point.

• 2:38Speaker 03

  Just hope. But you know why? It's because you stuff so much into the burrito. That's why.

• 2:43Speaker 02

  The analogy still works.

• 2:44Speaker 03

  You know, you're just hanging on to the burritos, that tortilla's hanging on for dear life.

• 2:49Speaker 02

  And there's a lot stuffed into my life right now, so it's perfect.

• 2:51Speaker 03

  Yes, and you know, one thing that's stuffed into your life right now is our co-host, Mr. OG.

• 2:56Speaker 02

  That's why it's so uncomfortable.

• 2:58Speaker 03

  How are you, man?

• 3:00Speaker 04

  I'm doing okay, except my thing here says that my connection is unstable.

• 3:05Speaker 03

  Douggy, Douggy thinks it's his connection that's unstable. Do you want to tell him? You want me to tell him?

• 3:10Speaker 04

  Oh, never mind. It says Tina's.

• 3:12Speaker 03

  Yes, and a guy who we always refer to as stable when we talk about him, just so he remembers it up there in upstate New York, Mr. Jesse Cramer's here. How are you, man?

• 3:23Speaker 05

  We went from burritos to unstable. Wasn't sure what was coming next.

• 3:27Speaker 02

  Dude, you look like you should live in a stable.

• 3:29Speaker 05

  Is that a horse joke or is that some other livestock, Doug?

• 3:34Speaker 02

  You're looking rather equine today.

• 3:36Speaker 05

  Joe, I got to see everybody at FinCon last week. I got to see Joe. Well, I saw OG not at FinCon. I bumped into him at the beach, I went in Huntington Beach. I saw Paula at FinCon. Doug was conspicuously absent, though.

• 3:51Speaker 04

  He wasn't invited.

• 3:53Speaker 03

  Is Doug real or AI? That's what everybody wants to know. Doug real or AI? By the way, Jesse, so I got to ask you, you finally got to hang out with OG. Tell me what a glorious moment that must have been.

• 4:07Speaker 05

  It was fun. It was really fun, actually. So I was, I got invited, don't ask me how, I got wrangled. It was very nice, though. I got wrangled into speaking at this conference called Future Proof. I was on a panel, so you know, we're up on stage, we're chit chatting on the panel, talking with the audience, and then get done with the panel, and you know, people are, a few people are coming up, saying hi, shaking hands, thanks, can I ask you a question? And then this guy comes up to me, and I look, and like, it takes me like a hot second, it's OG. And we hung out and it was great. It was glorious. We had a wonderful time.

• 4:39Speaker 03

  As well, did OG give you 10 bucks to say that?

• 4:42Speaker 05

  I had a wonderful time. I don't want to put words in OG's mouth.

• 4:45Speaker 03

  OG, how was it hanging out with the Jesse Cramer?

• 4:48Speaker 04

  Uh, you know.

• 4:51Speaker 02

  Oof, oof. Not reciprocating the enthusiasm.

• 4:55Speaker 04

  I felt rather offended that he didn't know who I was.

• 4:57Speaker 05

  It's like, you know, when you hear stories about someone who, when they get attacked, they're like, in that first second, I wasn't sure what was going on. I was kind of like, I was, should I defend myself? What do I need to do? That's all. It's like, next thing I knew, you know, I've got my personal space, I've got a little radius. Next thing I know, there's someone in my radius, it's OG. So for that first half second, just didn't know what to do, but then once recognition came over me.

• 5:21Speaker 04

  It's called a bro hug, Jesse. I was going for it.

• 5:23Speaker 05

  Then we hugged it out. Then we hugged it out.

• 5:25Speaker 03

  Yes. Speaking of somebody who is in our orbit at Stacking Benjamins, because he is our brother show, Earn and Invest, we would call him a guest, but he's easier far too often to be a guest.

• 5:38Speaker 06

  I'm the stability of the podcast. You finally entered, there's finally some stability here. We can now progress.

• 5:44Speaker 03

  You're not hanging on like a burrito, Doc G?

• 5:46Speaker 06

  No, no, no. I've got a little bit more than hope today.

• 5:49Speaker 03

  For people new to Stacking Benjamins and don't know about the wonderful stuff you do at Earn and Invest, what's going on over there, man?

• 5:57Speaker 06

  We have been busy. By the time you're listening to this, we're going to have Christie Talarico on. We're going to talk about HR benefits and how they can serve people better. So we've just been busy talking to people, been doing some solo episodes, getting ready for my book launch. The Happiness Code is coming in March, and so all that's been going on.

• 6:16Speaker 03

  The Happiness Code. I can't wait for us to dive into that. Well, today, Doc, how about we talk about the misery code? We're going to talk about, because what happens is people get these ideas in their head that, hey, I've got all this cool stuff that I think should apply to me, right? That I can go get, the internet says that I can do it, and then you find out that, well, maybe, maybe either you can't or you shouldn't. We're going to find out what concepts those might be, going to ask Doc G, OG, and Jesse. I feel like we got some alliteration going there, Doug. I don't know what's going on. We're going to ask them what they think about these different concepts, what could go wrong when it comes to these concepts?

• 7:01Speaker 03

  But first, we have a couple of sponsors who help us keep on keeping on, make sure this is free for you every time we publish. So we're going to hear from them, and then we're going to come back and talk about money moves you want until you see the actual bill. If you use any type of note-taking software at all, I think you really, really want to try the one that I use. I've used many different note-taking software programs, and this is the one I can't stop talking about. There's that sinking feeling you got that a meeting ends, everybody's nodding in agreement, and then two days later, you realize, nobody wrote down the important stuff. Well, guess what's happened since I started using granola.ai? All of the important stuff was written down.

• 7:45Speaker 03

  Granola is an AI-powered notepad that makes your meeting notes useful. It captures what happens in your meetings and turns it into clean, structured notes with decisions and action items pulled out and made easy to find, the best part. It integrates seamlessly with how you already work, so you don't have any setup, configuration, no friction. It transforms messy meeting calls into something you can actually reference weeks later. It's been so amazing at Stacking Benjamins. I can go back and go, hey, what were my notes from two weeks ago? It still keeps them. It's incredible. It takes better notes, the nuance in the notes of what's important and what's not, truly makes granola a time saver.

• 8:27Speaker 03

  It's the only note-taking AI that I've ever used that I can't stop talking about. So once you tried on your first meeting, it's hard to go without, you could try totally free, head to granola.ai/SP. I hope you do. That's granola.ai/SP to get your time back. Go to granola.ai/SP. Try it on your next call. Well, you may know the chaos is the name of the game here in mom's basement, what with guests coming in and out, Cooper the cat getting in the way, Doug being, well, being Doug. The holidays make it even worse because it's all about food and big meals, and the problem is prepping for those takes forever. But what about those between meals, right? The meals between those huge, huge bookends?

• 9:12Speaker 03

  Well, that's where Factor comes in. Factor is made with high-quality ingredients that you recognize and trust with over 175 banned ingredients. You always know you're eating something that's good for you, even when you don't have time. It's ready in two minutes, whether it's lunch between meetings or dinner after holiday shopping. Factor requires zero prep cleanup or effort from you or mom, so you can focus on everything else in your day. Factor even has heart-smart options like the Green Goddess Baramundi with tomato rice, peas, kale, and green beans, or the enchilada-style chicken and sweet potatoes. Those are so good. They're crafted with lean proteins, fiber-packed fruit and veggies, and healthy fats.

• 9:57Speaker 03

  Try those out, your heart and your taste buds will thank you. For Cheryl and I, Factor has been a great way for us to stay busy and focus on family life and beating mom at card games. I use Factor, and you should too, so let's eat real, stackers. Head to factormeals.com/sb50off, use code SB50OFF, and you know what? You're going to get 50% off and one free breakfast item per box for one year while supplies last until December 31st, 2026. That is code SB50OFF at factormeals.com, SB50OFF at factormeals.com. See website for more details.

• 10:50Speaker 03

  Okay, guys, today I am giving you everything people say they want with money, bigger returns, guaranteed income, and earlier retirement, successful kids, and investments normally reserved for the velvet rope crowd. But every offer comes with an invoice, right? You go, I'll take that. And then you actually see the fine print. And, uh, well, it gets, it gets ugly. So for each offer, I'm going to ask each of you to vote in or out, and then name what you think is the worst credible invoice you believe comes with the deal. So I'm going to submit to you a situation, and you go, yeah, I'm in, even though this is the downside. Oh, gee, you and I a lot on the show, we talk about every investment as a downside. And if you think it doesn't, you

• 11:34Speaker 03

  haven't thought hard enough about it. So name whether you're in or out, and the worst credible invoice you think comes with this deal. So let's start with you with this one, OG. I can put 10% of my portfolio into a leveraged stock market fund with the potential to dramatically outperform the S and P 500 over the next decade. Are you in or out? And what's the worst credible thing that could happen?

• 12:03Speaker 04

  Uh, I'm out. And the worst thing that happens, which will actually happen, it's not hypothetical, but it will, uh, you lose 98% of your money.

• 12:13Speaker 03

  Oh, wait, what?

• 12:15Speaker 05

  98% of the 10%.

• 12:18Speaker 04

  Yes, correct.

• 12:19Speaker 05

  Yeah, yes.

• 12:20Speaker 04

  That's if you don't get stupid and go, wait, I should buy low.

• 12:24Speaker 03

  What do you mean by that? Tell everybody why you think this is a bad deal.

• 12:27Speaker 04

  Leveraged ETF positions are meant to be a daily traded thing. So you're betting on the daily movement of that index or that thing, whatever you're betting on. Honestly, I think you'd have better results if you'd like literally went on Kelsey and actually did betting, because I think that it's a little bit, uh, I think you got better odds. But because it's a daily reset, and the multiplier effect is 2X, 3X, whatever, if you have a negative day, it's negative day times 3X. And now it resets back to zero. So it's not like you can have like five straight days in a row, and have them be good and offset one of the bad days. I think there was a study on this. I don't remember where I read it. Well, let me rephrase.

• 13:11Speaker 04

  I know there's a study on this. I don't remember where I read it. But anybody that held it, I think the number was five years. They, they lost 98% of their money.

• 13:19Speaker 03

  98% of their money. Holy cow. Jesse, let's go to you. Let's change the game just a little bit. Uh, so it's not the leveraged ETF where you're going to lose their money, even though you and I see people do this all the time. Well, heck, all of us see investors, brand new investors go, oh, my goodness, all this leverage it. I think the market's going up. Let's say instead of leverage, let's say it's one of these newer, active themed ETFs, right? It has a theme, like the theme where you are tracking, uh, let's say people in Congress, right? And what congresspeople are investing in, you're investing in the same thing. 10% of your investments into that, are you in or out?

• 13:58Speaker 05

  I'm not an expert on these thematic ETFs, not an expert. From what I know, I'm, I'm going to lean toward out. Why? Well, for one reason, they are likely, they come with higher fees, right? You're not going to get a thematic investment at, you know, hundreds of a percent. It's probably going to cost you half a percent or something like that. So higher fees, always a little cautious there. Another reason why is that I would want my investing philosophy to have some academic rigor. If I had my choice, I want it to be a little bit, you know, robust. A lot of these thematic ETFs are more, they're more like jokes than anything else. Again, no relation, but he is my uncle, Jim Cramer. There's the inverse Kramer ETF, right? So it's just like, well, we think Jim Cramer is a bit of a comic character on CNBC.

• 14:42Speaker 05

  He's always pushing buttons, making sound effects. Who does that? We're just going to do the exact opposite of him. Like, there's no academic rigor there. It's just kind of this, you know, it's almost like a meme. It almost is like a meme. So for, for those reasons, I would avoid, if I was being serious, I would avoid the thematic ETFs.

• 14:59Speaker 03

  Okay, Doc, so what makes you change from out to in on this deal? We already heard that leveraged ETF is not out on that thematic. Jesse says he's out on that. What sweetens the pot to some S and P beater that makes you go, yeah, I'm listening?

• 15:17Speaker 06

  Generally, I'm out too. But I interviewed Alex Edmonds, who wrote a book and, and does actually research about how to beat the market. And believe it or not, some of these thematic ETFs work. I mean, there is some real data behind, for instance, momentum in the short term and reversal in the long term. And so you can get these themed ETFs, which do really deliver above and beyond market beta. But you've got to pick the right person at the right time, which of course then puts it at risk. So I generally am actually too lazy of an investor. I just don't want to think that hard about it for a perceived alpha that I may or may not get. I'm a big fan of market beta. But if you are interested in it,

• 16:00Speaker 06

  there are some academically proven ways to try to deliver a little bit better. We know there's an equity premium, right? Some people believe there's a small cap value premium. So there are some premiums there, and there are some themes that we could possibly follow, which may not take a huge amount of research or energy. But again, I'd rather stick with beta. I'm, I'm not too worried about the possibility of alpha.

• 16:27Speaker 03

  We've seen this, OG, with some fun families out there. I mean, dimensional funds come to mind, right? They're not trying to pick what's going to win. They just kind of, it's a little more obvious what we'll probably lose when it comes to the index. Is that what gets you in on this idea of the possibility of an S and P 500 beater?

• 16:46Speaker 04

  I, I just, I don't even understand why it would matter to try to beat anything. The, the S and P is Standard and Poor's list of 500 stocks. The Russell is Russell Investments 1800, list of 1830 odd positions. Who gives a crap what it does? Like, the only thing that matters is whether or not you reach the goals that you need to reach to, you know, or get the returns that you need to reach your goals. If you beat the S and P by 300%, but still don't have enough money to reach your goals, awesome, you're still dead broke. So the whole idea of, of trying to beat a mythical list by a group of people seems really stupid. In fact, if you wanted to do it,

• 17:28Speaker 04

  what I would do is put together a list that you could always beat. Why not create a list of the crappiest stocks? And then you could be like, I beat the index. And then you will have like, a lot of emotional, like lift with that, because you'd be like, this is awesome. I am beating this list, and I'll just call it an index. And then I can tell my friends I beat the index.

• 17:48Speaker 03

  You'd be confident.

• 17:49Speaker 04

  You'd have so much confidence. Everybody. Yeah, your life would be way better.

• 17:53Speaker 03

  Jesse, is this a problem that we're obsessed with beating something, right? Where we're like, it's some type of a race or a competition versus a competition between us and our goal?

• 18:04Speaker 05

  I, I think so. And I think not only do I agree with everything OG just said, this idea of beating a benchmark is the wrong question. And that's essentially what OG is saying is we're not really asking the right questions. But it even gets a little bit worse than that, because, because what OG said is most important. We're, we're asking the wrong question. But then even when we go one layer deeper, and we say, well, let's look at that wrong question. Should you be trying to beat the S and P 500? Then the, the analysis that people do is often wrong. Just, just meaning that, you know, why is it just the S and P 500 that we care about? Why is it just the Russell 2000 that we care about? My, my point is that oftentimes, like, people don't really understand the benchmark itself, or why they're picking that benchmark, or is it right for me to compare my 50/50

• 18:46Speaker 05

  portfolio against the S and P 500? Well, of course not. Have your portfolios in bonds. I think that we are maybe a little bit benchmark obsessed, and, and we shouldn't be. And then even when we are, we aren't looking at benchmarks the right way.

• 19:00Speaker 06

  I, I mean, I think we need to change the frame a little bit, because there is a time and a place for trying to beat, I'm not going to say benchmarks, but there's a time and a place for alpha versus beta. And I think we have to look at the framework. Most of us are not trying to build wealth in the stock market. We're trying to maintain wealth and beat inflation. But if you're trying to build wealth, you don't want to diversify, you want to concentrate. And so if you're looking to concentrate wealth, and instead of doing it by being a doctor like I did, or being a financial advisor, doing whatever you do for a living, if you're like, I'm going to build wealth through the stock market, then I think you do want alpha. But the way you're going to get alpha, and the way you're going to, then you got to hit a home run. But hitting a home run is probably an individual

• 19:43Speaker 06

  stock, more likely, right? It's going to make a big bet, hit it right, and build wealth. It's concentrating your risk. So I think the bigger question is not whether we're trying to beat a benchmark, or even whether we want alpha or beta. The question is, what is our goal here? And for most of us listening to this, our goal is to concentrate wealth in our profession, or however we make most of our money. And then we take that money that we concentrated with our profession, and put it in the stock market to diversify. But then you're not trying to hit the home run with diversification. You're trying to beat inflation and then some a little bit. And I think that's really the frame we should look at this.

• 20:17Speaker 03

  Well, I'm glad you brought that up, because like Brian Feraldi said, when he was on a couple weeks ago, Jordan, he, he was talking about how if you're wrong, if you concentrate, you're going to build wealth faster, or you're going to lose it faster, right? And have you right-sized that investment so that you can accept the risk that the downside might happen? Let's stick with you for question number two. Are you in and out on this one, Doc? One stock has made you wealthy, and now represents 40% of your portfolio. So you had the concentration, it goes up, it's now 40%. Selling enough to diversify would trigger a six-figure tax bill. I want to keep the winner. In or out? And what's the worst thing

• 21:01Speaker 03

  that would happen if you did keep the winner?

• 21:04Speaker 06

  I mean, I'm in for selling and diversifying. Let's talk about the worst on both sides.

• 21:10Speaker 03

  Okay, so you're out on, you're out on keeping it.

• 21:13Speaker 06

  Yes, I'm, I'm selling to diversify. Let's talk about the worst part about both sides, right? The worst part about staying, right? So concentrated is you may lose the bet. Being concentrated always puts you at a risk. And once you have the wealth, you want to protect it, not necessarily get the outsized returns of the home runs. So if you stay in the concentrated risk allocation, the likelihood you could lose it all or lose a big percentage of it is high. Let's look at the other side. The other side is if you diversify and take the tax hit, the tax hit's no joke. And God forbid, you're 63 years old when you do that. You may get all sorts of Irma charges at 65. You may mess with your capital gains tax bracket.

• 21:56Speaker 06

  You may mess with your social security tax. I mean, the problem is income sucks, right? Taking more income always hurts.

• 22:04Speaker 03

  Is that, is that the quote of the day? Income sucks. I don't want more income.

• 22:08Speaker 06

  No, I mean, it really does.

• 22:08Speaker 03

  The reason I live in a tent is because.

• 22:11Speaker 06

  Gross income really hurts in other ways. And that's why you really do want to work with your accountant. It's the Dunning Kruger effect. We think we know more than we do, and often we make a decision and only understand the immediate implications. And sometimes we don't understand the other implications. So this is one of those times where really talking to your accountant or your financial advisor.

• 22:30Speaker 03

  I just took, I keep, these buttons are killing me.

• 22:35Speaker 02

  Created a cliffhanger there.

• 22:37Speaker 06

  You didn't like what I was saying, did you?

• 22:41Speaker 03

  It's just like when John Mulaney got censored at the end of that joke on the Emmys the other night. Just, yep, he's gone.

• 22:47Speaker 06

  He's out.

• 22:48Speaker 03

  Yes. All right, let's go to, uh, let's go to Mr. Kramer. You also out on keeping it when it's now 40% of your portfolio?

• 22:59Speaker 05

  Yes, I am out on keeping it. You've won, you've won. Something that you invested in did really, really well. And it did so well that it went from being a, a normal position in your portfolio to now being half of your portfolio. So you've had a really big win. And unfortunately, part of having a really big win is that you have to pay some taxes. And something that Jordan alluded to there, that is exactly the right thing to keep in mind is that just because you should pay some taxes or have to pay some taxes, it doesn't necessarily mean that you do it all at once, right? There can be some thoughtful tax planning that goes into it and to understand either second order effects, or maybe it's just something as simple as like, okay, you know,

• 23:42Speaker 05

  you know, doctors hate this one simple trick. So one really simple trick is you sell half of it in December and then you wait two weeks and you sell the other half of it in January, simply to spread it across two tax years. I mean, it's a very simple thing. The point is that there are usually smarter and dumber ways of realizing these big tax bills and, and it can help to try to, to do some of your research and figure out one of the smarter ways first.

• 24:06Speaker 03

  Well, even without the tax bill, oh gee, I mean, I'm, I'm just going to assume that Doc G is out on keeping it. Jesse's out on keeping it. You're probably out too. But assuming that you are out, how do you talk to a client about that? Because I'm thinking it's the early 2000s and this really happened in my practice. I had a client that owned a bunch of Apple stock. It went through the fricking roof. She had, to use Jesse's phrase, she had won, Jesse. It was, the game was over. She'd made a ton of money. I'm like, you know what? You should sell it. And then I said, all this good, the iPhone had just come out. So we know exactly when it was, it's 2007, right? And, and I said the phrase, what else good can happen after this?

• 24:52Speaker 03

  Think about selling Apple in 2007. She did really well, but there was still a lot of winning to go. So, oh gee, how do you talk to a client about giving up all this upside potential when it comes to the thing that got them where they are?

• 25:15Speaker 04

  I would not sell the stock.

• 25:18Speaker 03

  You would not sell the stock? You would keep it?

• 25:21Speaker 04

  Yeah, it's winning, man.

• 25:23Speaker 05

  Can we just let the audience know about that prop? That was good prop work.

• 25:26Speaker 04

  Yeah, audience.

• 25:27Speaker 05

  Like a little, little Karnak.

• 25:29Speaker 02

  They just did a sight gag and nobody knew it.

• 25:31Speaker 03

  Yes, for those of you not with us on YouTube.

• 25:33Speaker 04

  I do most of my gags for you guys, as you probably know. So.

• 25:37Speaker 03

  He just took a, uh, he took an envelope and opened it up and inside was the answer to the question, which was different than I had assumed.

• 25:46Speaker 04

  Karnak from, from.

• 25:47Speaker 03

  Johnny Carson.

• 25:49Speaker 04

  Johnny Carson, anyways.

• 25:50Speaker 03

  And, and he tells us we're old, Doug, but anyway.

• 25:53Speaker 04

  I think that if you were in this position, I would want to find a more reasonable way to offset the tax liability as well as provide some diversification. There's a lot of really, really, really great investment plans, investment strategies out there. None of them are free, so you got to evaluate the cost structure. But even something as simple as saying, hey, let's protect some of the downside of this large position. I mean, if you're going to have a hundred thousand dollar tax bill, you know, the position's probably 500,000 or a million or something, depending on your cost basis, right? Maybe we should buy insurance on the stock. Let it keep going up in your Apple example, Joe.

• 26:38Speaker 04

  Because the biggest risk that you're trying to solve for is this is a large percentage of my portfolio. If it goes down, it totally changes the trajectory of my net worth. Like if it goes down more than the market, right? If it's different than what the market does. Alternatively, in your example, if your client would have actually held on to their Apple stock, they would have a hundred million dollars right now, which is also a different plan. You know what I mean? I love the comparisons. I think maybe Apple's a little bit too far removed for a lot of people because it's always pretty much gone up. But if you've ever done the example of Bitcoin, you know, you got, dang it, if I'd have bought, I knew Bitcoin, I knew this was, I should have put $10,000. No, you wouldn't have. You would have never done that because it was stupid.

• 27:22Speaker 04

  And then secondly, even if you did, as soon as your 10 grand turned into 20, like eight days later, you'd have been like, I'm the smartest investor in the history of mankind. I'm taking my 20 grand and running. You would have had to go through, how many has it been? Six times it's got cut in half as it's gone up to where it is today. I don't think it's fair to evaluate the sale decision post, or the, the sale decision postmortem because.

• 27:44Speaker 03

  Money burning quarterback it.

• 27:46Speaker 04

  Yeah, I mean, at the end of the day, you, you had no idea what Apple was going to do. But I think that there's a better way to diversify your portfolio and you should pay attention to some of those strategies. You got to evaluate the cost structure, see if the juice is worth the squeeze there. But, um, but there's some opportunities.

• 28:02Speaker 06

  Hey Joe, there is an actually academic answer to this. If you're just looking at returns, believe it or not, and it depends on how quickly a period the stock went up. So there's this thing called momentum and there's been great academic research that shows that momentum actually brings slightly higher returns. And there's also academic studies of something called reversal, which shows that stocks that have been running high for a long time are likely to reverse. And so the academic point is actually how long the stock has been going up. So in that scenario you just gave us, if you said, boy, it went up 30% in the last two or three months, you could argue based on momentum to let it ride for another eight to nine months. But after you hit about a year to two period, you go from the momentum premium to pretty

• 28:47Speaker 06

  much the reversal premium. One could argue in the short term, you should hold on to a stock that's rising like a star. But in the long term, after it's been about a year, year and a half, that you should get rid of it because the likelihood is it's actually going to reverse.

• 28:59Speaker 03

  Boy, but I just think.

• 29:00Speaker 06

  Really, there's really good academic research on both of those.

• 29:04Speaker 02

  But what's your definition of, of long-term? Because.

• 29:07Speaker 06

  One to a year to a year and a half.

• 29:09Speaker 02

  Right, well, that is incredibly short-term. I mean, if you look at, I bet, I'm wondering if any of you guys know what the single greatest return is in the American stock market history?

• 29:21Speaker 05

  Philip Morris.

• 29:22Speaker 02

  Nope.

• 29:23Speaker 04

  Monster Energy Drink.

• 29:27Speaker 02

  Nope.

• 29:28Speaker 03

  Well, it was for OG after he drank it. He was like, this is the best return ever.

• 29:32Speaker 02

  It's Home Depot, believe it or not. A thousand dollars invested in Home Depot at its IPO would be $34 million today. It beats Apple and it beats Nvidia. But that value wouldn't have been realized and you would have cratered so many times. But the value is in the holding of the stock. So I'm saying I would have been, I don't know if I'm in or out. I probably would have gotten rid of the 40% of my portfolio as well and diversified. But if you really want to roll the dice and see if you get the big return and be on OG's team, I mean, there may be a reason to hold on to that because you could have a Home Depot on your hands and not, you won't know it until you've held it for 40 years.

• 30:13Speaker 03

  It is interesting using, uh, what I assume OG was an option strategy to protect your downside, you know? Maybe I'm going to, maybe I'm going to hold it. But I mean, I, I look at what it would cost me to cover that risk that it might go the wrong way.

• 30:29Speaker 04

  Yeah, I mean, there's options. There's a lot of different things. Yeah. Beyond the scope of our discussion today, but just selling it because you're scared of the tax guy? That's crazy for all the reasons Doc G talked about in terms of, you know, the downstream effects of that. But also burying your head in the sand and saying, you know, I can't sell it because I don't want to pay the taxes ignores the other side of the equation, which is all of the, you know, single stock exposure that you have.

• 30:56Speaker 03

  All right, guys, we all love LOVE guaranteed income. What could go wrong with guaranteed income? I'm going to ask you about guaranteed income streams and whether you're in or out on that. And then we're also going to talk about retiring five years earlier. That's something everybody wants, right? What if I give you a scenario about retiring five years earlier and will you be in and out in that scenario? That and more coming up. But at the halfway point of every Friday Stack Your Benjamins episode, we have this year-long competition between OG, Jesse and Paula Pant. Doc G, you're playing for Paula Pant today. I can't believe what I'm about to say. I cannot believe what I'm about to say. You ready for this, Doc?

• 31:35Speaker 06

  Mm-hmm.

• 31:36Speaker 03

  Doug, tell everybody the score.

• 31:39Speaker 02

  Doc, you are sitting in the worst time in history to be sitting in Paula's seat. The worst time in recorded history because Paula is tied for the lead. The great news for our, for our stackers is this is the best the trivia has ever been. This is the greatest season in stacking Benjamin's trivia history. We have Jesse with nine points, OG with 10 points and Paula with 10 points. We've got a chance to have a three-way tie today as we're coming down the home stretch of the year. Man, this is what we play for, isn't it, folks?

• 32:16Speaker 06

  I will never pass up the opportunity to lose for anyone, including Paula.

• 32:22Speaker 02

  But there's actual pressure now.

• 32:24Speaker 03

  For those of you that think that Paula's been bad at trivia, they forget that Doc G, but you've pulled a couple out of the hat, man. There's been a couple of times where I'm like, man, where did that come from? Is today the day that Doc G does that again and propels even weirder than today, Paula into first place? What would that be like? That'd be so strange. Or is OG going to reclaim the lead this year? Or is Jesse gonna make it a three-way tie while he is trying to defend his crown from last year? Well, only Doug knows the answer. But first, Doug, you gotta give everybody the question, man.

• 33:04Speaker 02

  Hey there, stackers. I'm Joe's mom's neighbor Doug. Here's something you'll be in on. Comics. October 2 marks the anniversary of one of the most successful comic strips in history. On this day, way back in 1950, Charles Schulz's Peanuts made its debut, introducing America to Charlie Brown and his friends. Although apparently Schulz was holding out on the good stuff because Snoopy didn't show up until the third strip two days later, which I respect. I mean, you can't just give people the dog on day one. You make them earn the dog. The strip started small, just seven newspapers, but eventually Charlie Brown, Snoopy, Lucy, Linus, and the rest of the gang became

• 33:46Speaker 02

  some of the most recognizable characters in the entire world. And you know, Charlie Brown and I actually have a lot in common. Every year Lucy charges Charlie five cents for psychiatric advice, and every year she convinces him she's gonna hold that football so he can kick it. And every year Charlie Brown believes her, which is basically the same relationship Joe and I have down here in the basement. Every week he hands me another trivia question and says, Doug, please just read what's on the page. I'm begging you. And every week I come running towards that football. You'd think I'd learned, but no, I am far too dim-witted to catch any of that. Hey, wait a minute. See what you did there. Anyway, Schulz eventually did very well for himself, but back then, he was

• 34:30Speaker 02

  a 27-year-old cartoonist whose brand-new comic strip had just been picked up by a handful of newspapers. So here's today's question. How much money was Charles Schulz paid for his entire first month of Peanuts comic strips? I'll be back right after I see if Joe can actually write me trivia without something evil in it. See the look in his eyes saying, trust me, buddy, definitely going straightforward with it this time.

• 34:57Speaker 03

  Our trivia is always so straightforward. It's so, so straightforward. Nothing going on there. We got OG going first, as is often the case. So Charles Schulz and Peanuts, how much did he get paid for his first month?

• 35:15Speaker 05

  So how much did he get paid for the month? Seven newspapers in the first month in 1950, and he was drawing a little, little comic strip. Twenty-five bucks.

• 35:28Speaker 03

  Twenty-five dollars for the entire month. Doc, what are you gonna do with that?

• 35:32Speaker 06

  I think it's higher than 25 bucks, but not a lot. Um, I'm gonna say 75. Let's give some space. So Jesse has to choose.

• 35:44Speaker 03

  Seventy-five dollars. Played like a veteran. Jesse, you're in this weird position of going third. What is going on?

• 35:53Speaker 05

  I feel like Paula. What can I say? It's a good feeling, Paula. It's a good feeling. Don't you worry. So I was writing down in my little red book here, and the number I came up with before anyone said anything was $250. And so I think I'm going to say 76 to one-up Doc G and take the high side.

• 36:16Speaker 03

  All right, to 76 dollars or above. Is that enough to make this a three-way tie? Doc G, with that number between 25 and 75, is he gonna help Paula take the lead? Or is OG right? And maybe, maybe he did it for free. Who knows? Doug knows. We're gonna find out when we get back. We are back. Well, you may know that chaos is the name of the game here in Mom's basement, what with guests coming in and out, Cooper the cat getting in the way, Doug being, well, being Doug. The holidays make it even worse because it's all about food and big meals. And the problem is, prepping for those takes forever. But what about those between meals, right? The meals between those huge, huge,

• 36:59Speaker 03

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• 37:43Speaker 03

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• 38:28Speaker 03

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• 39:08Speaker 03

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• 39:49Speaker 03

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• 41:48Speaker 03

  All right, OG, you started at $25. The other two went significantly north of you. How are you feeling?

• 41:54Speaker 05

  As my good friend Sabrina said, my give-ifs are on vacation for this right now. So I don't know.

• 42:04Speaker 03

  You feeling good, Doc G, about the numbers between 50 and 75?

• 42:09Speaker 06

  I probably should have gone a little- A little bit higher because I think then Jesse inched me out, but yeah, who knows? You never know.

• 42:15Speaker 03

  Sounds like with this number being 250, Jesse, if it was 239, you would have taken the, the upside.

• 42:21Speaker 05

  Yeah, I'm just, you know, going for the three way. Who doesn't like a three way? 10, perfect 10.

• 42:28Speaker 03

  Here we go. Doug, give us the answer, man. Who's taking home the win?

• 42:37Speaker 02

  Hey there, stackers. I'm certified football holder and guy whose drawing of Snoopy looks like a baked potato. Joe's mom's neighbor Doug. When peanuts debuted in 1950, Schultz's strip was appearing in just seven newspapers. He wasn't exactly getting rich, but things changed pretty quickly, which proves something I've been telling Joe's mom for years. You gotta spend money to make money. Admittedly, mostly I've been saying that while I was ordering appetizers, but you know, the principle is sound. Peanuts went on to become one of the most successful comic strips ever, eventually appearing in thousands of newspapers around the world. So before the break, I asked you how much Charles Schulz was paid for his entire first month of peanuts?

• 43:17Speaker 02

  Well, the correct answer was $65 higher than OG's guess, $15 higher than Paula's guess, and just $14 higher than Jesse's guess, which means Jesse is today's winner because Charles Schulz earned just $90 for his month, first month of comic strips. And we have a three-way tie. Bet down your patio furniture, folks. It's about to get stormy up here.

• 43:43Speaker 03

  Unbelievable. Going into the fourth quarter, we have a three-way tie. How about that? Congratulations, Mr. Kramer.

• 43:50Speaker 05

  It's purely the benefit of going last.

• 43:53Speaker 03

  While Paula doesn't make it work the entire, entire.

• 43:57Speaker 02

  Not everybody can make hay in that position.

• 43:59Speaker 03

  So close, Doc G. You were close.

• 44:01Speaker 06

  I know. I always give myself the credit that I was actually the closest with my guess.

• 44:05Speaker 03

  Until somebody got closer.

• 44:07Speaker 04

  So if I've been in the lead the entire year, so I've always gone first, is the next week, the first week that I get to go last?

• 44:14Speaker 03

  You go.

• 44:15Speaker 04

  Or do I have to go in first again because I still?

• 44:18Speaker 03

  No, you go second because it's based now on last year's final, the way we finished last year. So Jesse will go first now, and then you will go second. Paula goes third.

• 44:30Speaker 04

  I see.

• 44:31Speaker 03

  Well, we're going to get yelled at if we don't go back into our discussion for today, which we're gonna start doing right now. Let's start with the gentleman who won this week's trivia contest. Jesse, here we go. You ready?

• 44:43Speaker 05

  Ready.

• 44:44Speaker 03

  Let's do this one. Everybody loves guaranteed income. I mean, what could possibly go wrong there? So here is the question. I can create enough guaranteed monthly income to cover every essential expense for the rest of my retirement, in or out, and what's the worst credible invoice you could get? What's the worst fine print?

• 45:08Speaker 05

  In, as far as it's, it's doable and in, uh, I think, I think some people can, can reasonably convince themselves that's the right approach. But yes, a really big invoice comes with it, which is simply that, you know, the, I really enjoy this concept, which is the, you know, the prospect of guaranteed income means that it's riskless, right? Guaranteed and riskless are synonymous. And whenever you have a riskless investment, naturally risk and reward are tied at the hip. So if there's no risk, you should not be expecting any sort of commensurate reward. And it essentially means that you are going to have to build up a larger than necessary nest egg because you are going to be taking no risk to create this guaranteed income stream.

• 45:50Speaker 03

  Are you saying the insurance company, the cost to provide that is going to be, they're going to want 15 bags of money to give you that, that option?

• 45:58Speaker 05

  Yeah. I mean, and that's even going potentially a bridge further than, than I was thinking. I mean, if you're going the insurance route, it's, it's not even really an investment, right? It's an insurance product and like me, meaning like an annuity, something like that. And, and yeah, in that case, it's a very typical retiree could probably give a bag of money to an insurance company and you won't even get your own bag of money back for 12 to 15, maybe even 18 years. They're just paying you your own money back before they actually start paying you any sort of quote unquote, return on your investment. If we're talking annuities, I'm not sure I'm in anymore.

• 46:34Speaker 03

  Oh, that's interesting.

• 46:35Speaker 05

  Bond ladders, tips ladders, something like that.

• 46:38Speaker 03

  Just a locked ladder with guaranteed products. And I see what you mean. It's going to take a ton of money to make that happen. Yeah. Doc, you in or out?

• 46:48Speaker 06

  I'm out. I'm not a big fan of buckets. And this is, I mean, all of these are bucketing strategies. And I would say, why bother with buckets if you can either go safe withdrawal or you can do guardrails? In other words, I don't feel the need or the fear. I think retirement is a leap of faith and you never know what's going to happen. So trying to get a hundred percent security is impossible, but we have a pretty good idea that good investing means a premium on your return higher than inflation. And ultimately I'm willing to let it fly. I'm willing to go with the safe withdrawal rate or some version of guardrails. I'm not a buckets guy.

• 47:22Speaker 03

  This is why I love collaborating with Doc G. Cause I love buckets.

• 47:25Speaker 06

  Yeah. Boring.

• 47:28Speaker 03

  Cause you are wrong. Uh, OG, you in or out on this idea? Guaranteed income for life?

• 47:35Speaker 04

  I'm with Doc G. Guaranteed income is, it's like my good friend Tommy Boy said, if you want me to take a dump in a box and market guaranteed, I can do it. I got time, but all you're getting is a guaranteed piece of crap. The reality is, is that the,

• 47:55Speaker 04

  it's funnier if I don't laugh, but you guys are laughing, so it makes me giggle.

• 48:01Speaker 04

  Listen, the number one risk to people in retirement is not guarantees. It's the fact that their money doesn't outpace inflation. It's because some idiot in the 1950s wrote something really stupid that sounded like, when you're 50, you should have 50% of your money in bonds. And when you're 60, you should have 60% of your money in bonds. That stupidity has transcended, you know, a few generations. And now we're trying to beat it out of people, you know, when grandma, grandpa died in their frigging late 60s. Okay, fine. But now people live to their 90s and a hundred, you have to outpace inflation. So if all you have is a guaranteed tips ladder, I mean, there's some inflation protection there allegedly. But, but if you've got, you know, a bond ladder or God forbid a stupid annuity,

• 48:46Speaker 04

  it's like this, this stream of income is going to be flat as your costs blow past it and double over a quarter century. And now what are you going to do? There's just, you're going to start eating into the corpus of your safety. And that's going to drive down the safety numbers, which causes you to eat into the corpus of it faster, which draws down the safety number faster and you die destitute. You've spent your entire life accumulating money and saving and investing and have seen the results. You get to 65, you're like, hallelujah, I have $3 million in my account. I did everything all the people told me to do. I saved, I invested, I managed my taxes. I didn't touch it. I didn't, I didn't stress out when the market took a crap. Here's what I'm going to do.

• 49:26Speaker 05

  In a box.

• 49:28Speaker 04

  Yeah. Here's what I'm going to do. I'm just gonna take all that stuff that may be successful or last 60 years of my life and throw it in the trash and go do something different. What, what kind of sorcery is this? You already had success. Just do the thing again. So yeah, guaranteed income is dumb. I'd replace social security with market-based income if they would let me. Like give me an account with my social security. I'll start right now. They can keep all of my social security contributions up to 49 and a half years old. And I will go from here until I stop working, put my money in an account and I will kick your, you know what?

• 50:07Speaker 04

  Come at me, bro.

• 50:08Speaker 02

  That's where you applied the filter was on ass. You didn't want to say that word, but all of the rest of that came out out loud.

• 50:15Speaker 03

  Welcome to the Stack Your Benjamin Show where I can start with, with you've done a great job and you've now guaranteed income for life. Isn't it great? And OG has you destitute in a ditch by the end of his answer to the question.

• 50:28Speaker 04

  You will. Yeah. You will be. I've seen it happen.

• 50:32Speaker 05

  OG is like, you know, that four-letter word that starts with F? FICA?

• 50:36Speaker 04

  Yeah.

• 50:39Speaker 03

  That's it. All right, Doc, let's, uh, let's go to you for the next one. Let's talk about early retirement. How about this? I can retire five years earlier than I originally planned, but my financial plan succeeds in only eight out of 10 of these simulations. They call it Monte Carlo simulation, right? I can reduce spending or return to work if necessary. Are you in or out? And either way, what's the worst thing that could happen?

• 51:07Speaker 06

  I am out, meaning I would not retire on a 20% failure rate, only because I don't feel like living a good life and being happy is synonymous with retirement. Like by the time you hit my age, you should be able to find a way to do some type of work you like enough to make your averages better than 80/20. What is the risk? Well, the risk of not retiring is that you die early or don't get to do the things you want to do because you have less time than you think. But the risk of taking the leap is that you run out of money. And so 20% risk is a pretty significant risk. And I don't, me personally, as I go farther and farther in life, I realize that retirement really isn't the goal. It's having

• 51:50Speaker 06

  more control of how you spend your time and doing things you really like to do. And I've just realized that you don't really have to retire to do that most of the time. So why not build the life you want to live and then you can figure in retirement, once you're living that life you want to live?

• 52:05Speaker 03

  So the risk is, is that your chance of being unhappy goes up?

• 52:10Speaker 06

  Risk of what? Of continuing to work?

• 52:12Speaker 03

  No, no, no. Risk of, it isn't just the fact that it fails 20% of the time. It's that you're retiring five years earlier and you're saying for what?

• 52:20Speaker 06

  I think we make the mistake of thinking that retirement and happiness are synonymous. I'd like to help people build a happy life and then we just figure retirement into it when it makes sense. But I don't think they're the same thing. And so it's hard to correlate both of those, right? They're just totally different things.

• 52:39Speaker 03

  Well, let's see, OG, 80%, eight out of 10, you in or out? Retire five years earlier or not?

• 52:46Speaker 04

  Absolutely. A thousand percent out of a thousand percent. The big thing that people don't understand, and Doc, I'm not throwing shade, bro, because you're a smart guy. Correct, sounds really strong. I want to say something differently on the Monte Carlo thing. A lot of people assume that when you look at a Monte Carlo simulation, whether you do it on a website, or you know, however you get it, and it says 80/20, the 20 is a risk of failure. And, and we think of failure as being we're at 0%. The reality is, what the Monte Carlo is saying by saying there's an 80/20 is it's saying in 20% of the time, we have to make a change to the assumptions.

• 53:28Speaker 06

  Which, which is fair enough. I assume that you had distinctive assumptions.

• 53:31Speaker 04

  Yeah, I know you know that, Jordan. Which could be, hey, we're just going to spend a little less this year. Or it could be something very dramatic, like you are totally F'd and you know, you're going back to work at 85. So it doesn't dictate the type of change, or the veracity of the change, just that there requires a change to be successful in this scenario. And the way that I explain Monte Carlo, I think it kind of helps people understand what's going on, is there's two ways to do financial plans, right? You can think about it this way, you can like put it in Excel, I got this amount of money, I'm going to grow it at this rate of return, I'm going to add this much every year, and da, da, da, da, da, da, da, goes up, and then I start taking money out, and da, da, da, da, da, it goes down, right? But the reality is that it doesn't work very linear like that. It's random. What Monte Carlo does is it takes your existing asset base, your

• 54:15Speaker 04

  existing savings, your existing spending projection, you know, as you say, I think I'm going to spend 80 grand a year. And then instead of taking a straight line of return, think about the last 100 years of returns on a deck of cards, where one side of the card has the year, and the backside has the rate of return for your portfolio, if you're up 70/30, if you're 50/50, whatever. This has happened already in the last 100 years, right? Your allocation has returned a result in the last 100 years. Monte Carlo says, let's shuffle the deck, play the game in a different way. Shuffle the deck, play the game a different way, shuffle the deck, play a game a different way. So you're getting real life returns, things that have actually happened, just in a different order. And so, just like in cards, sometimes you get some really crappy cards in a row. And Monte Carlo is trying

• 55:00Speaker 04

  to simulate the probability of having all of these crappy cards in a row when, when it matters, right? Talk about sequence of returns risk, or whatever. Or what happens if you have really good cards? Because it's unlikely that the next 100 are exactly like the last 100. So if you're 80%, ship it.

• 55:19Speaker 03

  Jesse, instead of a me too, I've got one more topic, but you know what? These guys have kids that are much older. You have a young family. So I just want to ask you this one last one I had. You can fully fund your children's college education, but doing it probably means working two additional years before you retire. Are you in or out? And what's the downside?

• 55:44Speaker 05

  I think I'm in for that one. Two years, right? I mean, whether it's, is it one year? Is it two years? Is it three years? The idea is, I'm at a point now where I enjoy what I do for work a lot. I think that helps. When I was an engineer, and I first learned about the FIRE movement, and I first learned about investing and all these cool things that we talk about, I was very much in a place where if I could pull my retirement in a year, or two, or five, or 10, I was on board. Like, the idea of ending work to pursue other passions was really high on my priority list. I like what I do now. So I'm not that, you know, motivated to stop working early. What am I motivated by? Well, I like the idea of earning a nice paycheck, so I can go do fun things with my family, and I can support

• 56:29Speaker 05

  my family. So for me, my priorities have shifted. And I think for anyone listening, your priorities are your priorities. One of the fun things about what OG and I get to do is we get to help you figure out what your priorities are, and help you achieve those priorities as you've stated them to us. So I would trade a couple of years of working, because I find them fun, in order to help out my kids that way. Also, I just wanted to state, I think it just shows how passionate OG is about Monte Carlo, because Monte Carlo, this very numerical thing, it's, you know, zero to 100. And, and he's so passionate about it, that 1,000% out of 1,000% is how strongly he felt in his Monte Carlo answer. I like that.

• 57:08Speaker 03

  Going to 1,000 for 1,000. That's a pretty big number. It's like a bajillion to a bajillion.

• 57:13Speaker 06

  10 times confident.

• 57:23Speaker 03

  I wonder which finger's coming for Jesse?

• 57:25Speaker 04

  I hate it when it does that.

• 57:28Speaker 06

  Another sight gag from OG.

• 57:29Speaker 03

  Who knew? Yeah, but I think the audio only audience understood what was going on there. Yeah, they might have.

• 57:35Speaker 04

  I think we got that squared away.

• 57:36Speaker 03

  And I'll tell you what's going on. I think we did a great job of these. And I think the real lesson, obviously, for our stackers is all this stuff sounds good, but each of you poked holes in each of these concepts. And until you know what the hole is in the concept that you're contemplating, like if it sounds great, and you can't find something wrong with it, you haven't searched hard enough. You just have not searched hard enough, because you guys were all great at poking holes and these things that we hear about every day. Hey, guaranteed income for life. Retire five years early, all the different things. All right. Let's find out, speaking of all the different things, what's happening where you live. OG, it is October, first weekend in October. What are you doing this fine weekend?

• 58:18Speaker 04

  PSLs, baby. What am I doing this weekend? Same as every weekend. I want to do a little fun, outdoor work tomorrow, and then undoubtedly softball Sunday morning. So.

• 58:29Speaker 03

  Softball Sunday, Sunday, Sunday.

• 58:31Speaker 04

  Like raking 10-year-olds. It's pretty awesome to watch.

• 58:36Speaker 03

  What?

• 58:37Speaker 04

  You might want to expand on that.

• 58:38Speaker 03

  Does that mean striking them out?

• 58:40Speaker 04

  Yeah, she's doing that. She's hitting on them. She's stealing bases. She's tagging people out. She is like a one-man wrecking crew.

• 58:47Speaker 03

  She's incredible. We got a future NIL situation going on at the Vanderman household?

• 58:52Speaker 04

  I didn't want to jinx it, but since you already did, I will, I will say, we are, we stopped saving for her college. Let me just put it that way. We're just, we're kind of all in on this at this point.

• 59:04Speaker 03

  That is so painful. Doc G, what's going on at the Earn and Invest Podcast, man?

• 59:09Speaker 06

  So if I'm correct, today is October 2nd. October 3rd, the Earn and Invest Podcast is having a meetup in Chicago. We are doing our annual Wealth with Purpose, that's my mastermind. We're doing our in-person get together, and we always open it up for a night at the bar. So it's going to be at 7:00 PM Central Time. If you are in Chicago, it is at the Duke of Perth Restaurant. That's 2827 North Broadway Street. They have wonderful fish and chips. Come hang out with us, earn and invest.

• 59:39Speaker 02

  I have had some ugly nights at the Duke of Perth.

• 59:42Speaker 06

  Yeah, yeah. They've got great fish and chips and lots, and quite a selection of alcohol, yes.

• 59:47Speaker 02

  It's the Scotch that really got me, not the fish and chips.

• 59:51Speaker 03

  And Doug, by ugly, let's be clear, you meant great night.

• 59:55Speaker 02

  They were mostly memorable. Yeah.

• 1:00:01Speaker 03

  Jesse, we save the best for last, man. What's happening at the Personal Finance for Long-Term Investors show here rounding out the year into the fourth quarter?

• 1:00:11Speaker 05

  Last week, an episode came out inspired by former Stacking Benjamins guest, Dr. Daniel Crosby.

• 1:00:18Speaker 03

  Oh, what a great guy.

• 1:00:19Speaker 05

  Awesome guy. And, and it was something he said on this very podcast about the three demons of overconfidence that inspired an episode. So that was last week. And then next week, I think I'm going to publish a, my favorite Charlie Munger quotes episode.

• 1:00:34Speaker 03

  Oh, that's going to be great. I can't wait to hear that. Because you, the, the way you dive into those things, really, really fun. I can't wait. And that's at Personal Finance for Long-Term Investors, and Jordan at Earn and Invest, and stackers and earners? Is that what we call them? Earners? E and I's?

• 1:00:52Speaker 06

  Earners, E and I's. Earn and Investors.

• 1:00:55Speaker 03

  Earn and Investors, yeah. Come hang out with Doc G in Chicago. It's always a good time. Or go over to get OG's daughter's autograph, because you can get it, that's like buying high, buying low, and then sell high, right?

• 1:01:10Speaker 04

  It'll be worth it.

• 1:01:11Speaker 03

  Good stuff. You know what else is sometimes worth it? Find out what Doug thought of today's episode. Every once in a while, it's worth it. Doug, what should we have learned on today's show?

• 1:01:22Speaker 02

  Well, Joe, first, take some advice from Jesse and Doc. If you have a great investment that's become an oversized portion of your portfolio, you won. Time to strongly consider rebalancing. Second, take some advice from the always effervescent OG. Guaranteed income is a fool's errand and a giant waste of time. But the, I think I actually undersold that. But the big lesson? Joe thinks I'll read anything. Yeah, right. Take this, Joe. You didn't even write this, and I'm making it up as I go along. See? You don't control me. Wait, that says control me, not control me. My bad. God, got me again.

• 1:02:08Speaker 02

  Thanks to the Jesse Kramer for joining us today. You'll find Jesse's Personal Finance for Long-Term Investors podcast wherever you find podcasts like this one. Trust me, it's out there. You'll love it. We'll also include links in our show notes at stackingbenjamins.com. Thanks to Doc G for hanging out with us today. You'll find his fabulous podcast, Earn and Invest, wherever you listen to finer podcasts. And finally, thanks to OG for joining us. Looking for good financial planning help? Head to stackingbenjamins.com/OG for his calendar.

• 1:02:43Speaker 02

  This show is the property of SB Podcast LLC, copyright 2026, and is created by Joe Saul Sehi. You'll find out about our awesome team at stackingbenjamins.com, along with the show notes, and how you can find us on YouTube, and all the usual social media spots. Come say hello. And oh yeah, 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 Doug, and we'll see you next time, back here at the Stacking Benjamin Show.