Some financial strategies aren’t bad, they’re just wildly oversold to people they were never built for. Joe and OG walk through five genuinely legitimate, sometimes powerful tools, cash value life insurance, municipal bonds, qualified longevity annuity contracts, net unrealized appreciation, and complex charitable trusts, and draw a clear line between the tiny slice of people these actually help and the much larger crowd who gets pitched them anyway. If you’ve ever had someone offer you a “special” financial strategy and wondered whether it was genius or a sales tactic, this episode gives you the framework to tell the difference.
What You’ll Walk Away With
- Why cash value life insurance almost never makes sense as a savings vehicle, and the very narrow situations where it actually does
- The real math behind municipal bonds, and why the “tax-free” appeal often costs more in lost growth than it saves in taxes
- A clear-eyed look at qualified longevity annuity contracts, and why giving up control of your money rarely makes sense at any wealth level
- The single tax strategy on this list that can genuinely save six figures over a lifetime: net unrealized appreciation on employer stock
- Why “borrowing against your assets instead of selling them” can be brilliant or disastrous depending entirely on how the economy moves
- A blunt reality check on 72(t) distributions for early retirees, and why the five-year commitment trips more people up than the strategy itself
- Why “there’s no free lunch” is the single question to ask about any complex financial product before you commit to it
Why This Matters Now
The financial industry has an incentive to make simple problems feel complicated, because complicated problems require expensive solutions. Most people’s actual financial life doesn’t need any of these five strategies, and that’s not a failure, it’s just math. But knowing what these tools are, who they’re actually built for, and what they cost when misapplied means you can spot the difference between a legitimately smart move and a sales pitch dressed up as sophistication, whether or not you’ll ever personally need any of them.
From the Basement
A Good Neighbor Day detour into Ted Williams’s legendary 1941 season, when he refused to sit out the final day to protect a rounded-up .400 batting average, becomes a genuinely moving story about doing things the honest way even when nobody would’ve noticed otherwise.
Resources Mentioned
Stacking Benjamins Coaching Program — Joe and OG’s new cohort program for financial coaches
Stacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking tool
Doug’s Trivia
- Ted Williams came to the plate eight times on the final day of the 1941 season. How many hits did he get, and was it enough to finish the season at .400?
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Other Mentions
Join Us Wednesday
Tune in on Wednesday when we bring you a conversation recorded live from Texas A&M University–Texarkana with Lauryn Williams, the only American woman to medal at both the Summer and Winter Olympics, about winning in sports, succeeding with money, and the audience’s biggest questions about both.
Written by: Kevin Bailey
Miss our last show? Listen here: Is “This Time Different”? A FinCon Panel on AI, Inflation, and Interest Rates SB1902 | Stacking Benjamins
Episode transcript
[00:00:00] opener: My plan is sound, mathematically sound. It cannot fail. It’s perfect. Three months from now, I will be worth $50,000, independent for life
[00:00:24] Doug: From Joe’s mom’s basement, it’s The Stacking Benjamins Show
[00:00:38] Doug: I’m Joe’s mom’s neighbor, Doug, and as a good neighbor, I gotta share. You ever wonder if you’re that outlier who needs a strategy different from the norm? On today’s show, Joe and OG dive into their top five strategies they wouldn’t recommend most stackers use, but for the right person, it’s the perfect fit.
[00:00:57] Doug: And good news for you, you won’t have to wait a lifetime for the perfect money trivia to impress your friends because I’m bringing it to you today. You’re welcome. This is a great one I’ll share halfway through this party on this very special holiday. That’s right, this weird holiday calendar Joe’s mom got me says it’s Good Neighbor Day, so let’s party, neighbor.
[00:01:20] Doug: And now, speaking of party, here come two guys ready to help you rock a personal finance party, but also who could totally work on being better neighbors themselves. It’s Joe and O-G-G-G-G.
[00:01:38] Joe: Hey there, Stackers, and happy Good Neighbor Day to you. Neighbor Doug, happy Good Neighbor Day. I think we’re great neighbors.
[00:01:45] Doug: Well, yeah, I know you do.
[00:01:46] Joe: I’m trying… I’m trying to come up with something good that we did to be very neighborly. Yeah, see, it takes you a minute, doesn’t it? It’s, it’s a bad one. Oh, we got a great show though, Stackers.
[00:01:57] Joe: You know how we’re gonna be a good neighbor today? We are going to dig into all that financial nerdery. I remember early in my career, I’m like, “What are some of those cool concepts that work for the right person?” Well, OG’s got a list of five. I got a list of five. We’re gonna dive into those. But we gotta meet the man, the myth, the legend.
[00:02:13] Joe: OG is here in the basement. How are you, brother?
[00:02:17] OG: I am, uh, patiently awaiting the next day of rain, which has, uh, presently been, uh, almost 70 days in Dallas now. Been a long time. The record is 84. Wow. In a normal summer, Dallas has 20 100-degree days, on a normal summer. So far in the month of September, we’ve had 17.
[00:02:38] OG: So it’s hot and dry Just- And anything’s cool and wet, baby …
[00:02:42] Joe: just, just absolutely w- waiting.
[00:02:45] Doug: Yeah, maybe don’t make that little campfire in your backyard.
[00:02:49] OG: Yes, no fires allowed. Even the mere thought of fire is forbidden.
[00:02:53] Joe: Right. I was thinking, don’t even think it. Well, we are thinking about great esoteric strategies on today’s show,
[00:03:00] OG: so- And who’s gonna have a campfire when it’s 106 out anyway?
[00:03:03] OG: That’s something that Joe would do. Until it cools off at night. I was out on my s- porch the other day with my Solo Stove. It’s like, “It’s 106, Joe.” “I know, but I really wanted a campfire.” Like,
[00:03:11] Doug: dude- Boy, it goes
[00:03:12] OG: down to
[00:03:12] Doug: 88 at night.
[00:03:13] Joe: That’s chilly. I did that once a couple of years ago. We had a non, for whatever reason, a non-humid night.
[00:03:19] Joe: Maybe it was right after a rain, and I’m like, “Man, it’s not humid. It’s kinda nice out. Let’s get the Solo Stove going.” My buddy Mike was up for it, comes over. We sat 12 feet from the Solo Stove like just, but just having that campfire. Yeah, when you’re
[00:03:31] OG: sweating it’s probably a bad idea.
[00:03:33] Joe: Probably, probably not great.
[00:03:35] Joe: Well, what is a great idea is that you know when the right time and place are for these esoteric strategies. We’re gonna dive into it. If you’re a financial nerd, you’re gonna love today’s episode. Even if you’re not a financial nerd, just knowing that these might be out of bounds for a lot of people is going to be a fantastic, fantastic episode, so can’t wait to get into it.
[00:03:55] Joe: First, we have a couple sponsors that help us deliver all this goodness to you for the incredible cost of free. We’re gonna hear from them, and then OG and I with our top five esoteric strategies that work for the right person. Remember Superman? It’s a bird, it’s a plane. Superman. Now there’s the equivalent for your money.
[00:04:16] Joe: It’s a budgeting app. It cancels subscriptions, protects your privacy, and helps you build credit. Heck, it even tracks your net worth. It’s the super app Fieldkit. You don’t wanna spend time managing your money, you want to live. So get Fieldkit so everything’s in one place and you stop staring at screens all day.
[00:04:32] Joe: Check it out at stackingbenjamins.com/fieldkit.
[00:04:37] Doug: Does it wear those sexy briefs, Joe?
[00:04:40] Joe: It does, yes. Very tight.
[00:04:42] Doug: All right. I’m in.
[00:04:53] Joe: Well, G, I’m sure you’re like me when you hear a client that comes in and goes, “Oh, I got this great idea that I saw on TikTok.” You immediately go, “Oh, no. Oh, no, no, no, no, no.”
[00:05:06] OG: Well, thankfully, uh, nobody that I know actually takes advice from TikTok, so.
[00:05:11] Doug: OG’s weeded them out long ago.
[00:05:13] Joe: Yeah. Yes.
[00:05:13] OG: Yeah.
[00:05:14] Joe: Except Joe.
[00:05:15] OG: Yeah, the TikTok, the TikTok crowd really is not, uh, is not our general market.
[00:05:21] Joe: Not who you’re, who you’re going after. What is interesting though, even at FinCon, and as we record this, I just got back from the financial creator conference called FinCon, and this woman I was talking to, nice lady, I said, “So what do you do?”
[00:05:36] Joe: She goes, “Oh, I help people learn how to use cash value life insurance instead of a savings account to reach their goals faster.” And I immediately went, “Nope.” Click. Just it can work until it doesn’t work, and when it doesn’t work, you’re gonna wonder, “Why the heck did I use life insurance to unravel my entire financial situation?”
[00:05:56] Joe: So we’ve got five of those you’re not gonna hear using cash value life insurance on one that works, uh, in, in my list. We might hear it in OG’s. Steve, play the awesome British announcer guy.
[00:06:08] bit: Number five.
[00:06:10] Joe: OG, you wanna do these like a snake draft? Maybe you go first, and then I’ll go first the next one, and we’ll go back and forth.
[00:06:16] OG: It’s your rodeo, buddy.
[00:06:17] Joe: Let’s do it. What’s your number five?
[00:06:20] OG: I didn’t really rank these in order. However, I will say that, uh, the first one that I’m, that’s on my list is, uh, cash value life insurance. I thought that was the one we were gonna match on.
[00:06:31] Joe: Well, it’s funny. You might hear cash
[00:06:32] OG: value life- And I would say permanent insurance.
[00:06:34] OG: I, I’m gonna change it to permanent
[00:06:36] Joe: You may or may not hear, I don’t wanna foreshadow, but you may or may not hear cash value life insurance using it on my list, but using it to replace your savings account, pay off your bills faster, you know, this idea of infinite banking.
[00:06:47] OG: Yeah. No.
[00:06:47] Joe: You probably won’t hear that on my list.
[00:06:49] OG: No. Definitely not. Doug?
[00:06:51] Doug: Hold on. If you’ve used permanent life insurance or cash value, aren’t your troubles over? Like, if you’ve used that insurance, you’re not worried about your financial future. If you’ve…
[00:07:02] OG: Well, I mean- If you’ve used
[00:07:03] Doug: the death benefit What, what am I missing here?
[00:07:04] OG: Yes, there’s that. I, I see what Doug’s saying.
[00:07:06] OG: But I also think there’s a little interesting side to that also, which is if you actually have this, you probably should be in a situation where all of your financial worries are taken care of because this is so far down the list of places to put money that quite literally everything else is, needs to be covered.
[00:07:25] OG: I mean, the, the use case for permanent life insurance is-
[00:07:28] Joe: As a savings vehicle, you’re talking about.
[00:07:30] OG: No. I’m saying the use case for permanent insurance, period, which has to be- With a cash value because that’s how th- permanent insurance works. You’re basically pre-investing your premiums. Here’s the thing.
[00:07:45] OG: A 90-year-old who buys a, a one-year term policy, it costs a certain amount, right? They have, they have the mortality table, and they go, “90-year-olds have X percent chance of passing away, and therefore the, the insurance cost for a million dollar t- one-year term policy for a 90-year-old is X.” Also, the cost of insurance and permanent insurance for a 90-year-old for a million dollars is also X.
[00:08:07] OG: It’s the same number. Mm-hmm. All insurance is the same cost. What happens and why this looks somewhat attractive is because early on when you’re 30, you’re overpaying it by so much money that it goes into an account, whether that account grows with a fixed rate of return or a variable rate of return But whatever.
[00:08:26] OG: You’re overpaying so much so that your premiums are flatlined throughout your entire life
[00:08:31] Joe: It’s to subsidize those later years
[00:08:33] OG: It’s just basically saying instead of paying, I’ll make up a number, $100 a month for term insurance at 30, you pay 400 a month at 30 for your permanent. And the reason you pay 400 is because all that extra 300 gets invested for later so that you’re still paying 400 a month when you’re 90, not 82,000.
[00:08:53] OG: Because that’s how much it would cost to have a 90-year-old buy life insurance, right? So, so it’s, it’s basically taking all the whole math and just flatlining it to a single premium. But the only reason that that makes sense is if you have a, a life-altering event where you can’t get coverage anymore.
[00:09:10] OG: For example, you have term insurance and now you have, you know, a heart issue, or you have some uninsurable thing and you still need insurance. A lot of times companies will allow you to convert your term to permanent without proof of insurability, so that’s a good use case. And then the other use case is, uh, at the end of your life for estate planning purposes.
[00:09:31] OG: And now to put this in perspective, you’d have to have a net worth, or you and your spouse, somewhere north of $30 million. And if you had that, then, then you’re starting to decide what’s worse. Do I wanna pay Uncle Sam 55%, or do I wanna pay the insurance company? And a lot of times the insurance premium is less than Uncle Sam.
[00:09:50] OG: So you say, well, a 90-year-old go buy a $10 million life insurance policy to cover the, the tax bill. It’s gonna cost him $8 million. It’s a lot
[00:09:58] Joe: of money.
[00:09:59] OG: But that’s way better than paying Uncle Sam 30 million.
[00:10:02] Joe: Yeah.
[00:10:03] OG: So those are the two major use cases. Everything else, pretty much garbage.
[00:10:09] Joe: Yeah, it is, it is some complex financial planning that you’re getting into when you start to look at permanent life insurance policies.
[00:10:16] Joe: You can use a permanent life insurance policy, I think, OG, sometimes as a substitute because of the long-term care riders that are attached to those, so for some long-term care issues maybe. You’re shrugging.
[00:10:28] OG: No. I mean, all, all it is is just putting lipstick on that same pig. It’s just once you start layering in other sort of products into other products, it’s because the first one wasn’t good enough to stand on its own.
[00:10:42] OG: You know what I mean? Like, it’s not a feature for you. In- insurance companies are not benevolent. Investment firms are not like, “Oh my gosh, you know, we should do this for the common good.” No, they’re all profit motive driven, period, full stop. That’s how it works. So any time you are, uh, you know, bolting on something to something else, it’s because the other thing’s just not good enough to hold its own.
[00:11:04] OG: I can tell you almost unequivocally anybody who says to you Um, you need to get permanent insurance right now because you never know what your insurability is gonna look like in the future, which is a common sales tactic to- Very common … a 25-year-old couple who just had their first baby. “Well, you should get this baby some insurance.
[00:11:24] OG: You know, you never know.” I mean, that is so effing slimy. I, if, if, you know… You know, what was that movie where you could do anything you wanted for one day? Like, you know.
[00:11:36] bit: Limitless? No.
[00:11:37] OG: No, no, no, no. No. No. No, Limitless was the one where he takes the pill and- Like, where, like, where no, no crime was legal.
[00:11:41] bit: Oh, yo.
[00:11:42] bit: Oh, yeah. Yeah. Uh, yes. Yeah.
[00:11:45] OG: So anybody who says that, you know, they’ve got a special condo laid out for them in the, uh, H-E double hockey sticks area of, uh- Oh … the afterlife. They have
[00:11:53] Joe: their own ring.
[00:11:54] OG: They have their-
[00:11:55] Joe: There’s like, there’s like
[00:11:56] OG: Dante’s rings of hell. Dante’s Inferno. Yeah, they have life insurance guy.
[00:12:01] OG: Yes.
[00:12:01] Joe: Slimy salespeople ring.
[00:12:03] OG: Yes. Please don’t do that, and don’t fall for it.
[00:12:07] Joe: My number five goes a different direction, but, you know, there are tax-free benefits to life insurance, which could be attractive for the right person. There are also tax-free benefits for municipal bonds. Municipal bonds are number five on mine, OG, because I saw way too many people, and still see too many people, who go, “Oh, I got these because they’re tax-free.”
[00:12:30] Joe: Well, the problem with loaning money, what a municipal bond does is you’re loaning money to a municipality. You’re loaning money to a city for public works projects. Could be the new library, the police station, the fire station, so a lot of good stuff. So you get this feel-good, you’re helping the city.
[00:12:45] Joe: Could even be paving roads. And as an exchange, you get many tax-free benefits of the municipal bond. The problem is, is you’re exchanging this tax-free benefit for growth, and what I often saw, OG, was people that are buying municipal bonds who seriously need growth in their portfolio, and they’re not in a high tax bracket, and they’re avoiding a fairly low tax in the big scheme of things that’s not punching up the growth that they could get if they just went with a regular taxable stock-based exchange traded fund or mutual fund, where they have a nice diversified position of owning the economy.
[00:13:25] Joe: So while the tax bite sounds attractive, I think this is a much more esoteric product, using municipal bonds in a portfolio, than people realize.
[00:13:37] OG: Really works primarily for people that are in a very, very, very high tax bracket with also very high state taxes. And so you have the opportunity to, uh, you know, to remove those.
[00:13:48] OG: Thankfully, it’s not as prevalent as you would think, and obviously the municipal bond market is huge, but from a retail investor standpoint, I don’t see it a bunch.
[00:13:56] Joe: That’s good.
[00:13:57] OG: At some level, it comes down to the math equation of the tax-free yield versus the taxable yield, you know? Because it’s not the same.
[00:14:05] OG: You’re not getting 5% in Treasuries and 5% in your munis. You get 5% in Treasuries and 2.7% in your munis, and you gotta do the math to go, “Is 2.7 tax free better than 5 taxable?”
[00:14:17] Joe: Yeah, it is, uh, not a great product for a lot of people.
[00:14:21] OG: And I’ll skip to the end. It’s about the same.
[00:14:23] Joe: Number four. My number four is an incredibly esoteric product, but when people hear about it, OG, they go, “Oh, this is a thing?
[00:14:32] Joe: This could be something that I could do?” It was introduced in 2014 for the person who worries about longevity risk, really worries about longevity, wonders about, uh, taking their money out, and is something that the insurance industry, again, just let’s put some bells and whistles on life, and that’s a qualified longevity annuity contract.
[00:14:54] Joe: These annuity contracts allow somebody to use their qualified money, turn it into an annuity, and have that last for a long, long, long time. So instead of having the same RMDs they used to have in the past, now they’re able to worry much more about what happens if I live for a long, long, long time. This is for a person who Frankly, I’m not sure who it’s for, OG.
[00:15:21] Joe: Because number one, if you don’t have a ton of money, you need growth, and you really don’t wanna give up control to a life insurance company. You’re giving up control of your money, and if you have a ton of money, I don’t know that you need… you’re especially worried about it. It’s for this really, really small sliver of people that have enough, but they are conservative enough that they’re willing to give up control of their money in exchange for a pension with their qualified money inside of an IRA.
[00:15:57] Joe: It’s a messy thing. I just think that when I heard in 2014 about this, and increasingly in 2015, ’16, ’17, ’18, I kind of rolled my eyes personally. I’d love to get your take on this because I’m like, “Uh, okay, this is a solution for a gigantic subset of people.”
[00:16:15] OG: Effectively what you’re doing is you’re saying, “Okay, I’m gonna take some of my capital.
[00:16:19] OG: I’m gonna put it into an account where it’s deferred. I- I… It’s gonna grow how it grows, right? Maybe I have some selection over that. Maybe it’s fixed, you know, whatever. And then I’m gonna turn it into an income stream from 85 to end of life. You know, and if I live to be 167 years old, joke’s on them. If I live to be 83, or I’m sorry, 87, joke’s on me.”
[00:16:41] OG: You know, it’s, it’s that, right? So if you just take those ages and swap them around and say, would we ever tell a 45-year-old to do this? “Hey, you got 20 years before retirement. Let’s take 50% of your portfolio. Let’s just set it aside. Let’s just set it aside. It’s gonna just, you know, just so that it can pay you money when you’re 65.
[00:17:05] OG: We’ll just set this aside. And oh, by the way, when you do turn it into this stream of income at 65, if you die at 66, nobody gets anything else.”
[00:17:15] Joe: It’s done.
[00:17:16] OG: Yeah. N- your spouse doesn’t get it. Y- you know, your, your family doesn’t get it. But great news, if you live to be 95, you know, you’ve been getting this stream of income for a long time.
[00:17:27] OG: Well, the big risk is, is obviously the, the, you know, if you get hit by a bus. The second big risk is, well, hold on a second. How am I going to keep up with the rising cost of living over my 30-year retirement at 65, or mine and my spouse’s 30-year retirement at 65, if this thing’s gonna give me a, you know, guaranteed income that pays my living expenses at 65?
[00:17:50] OG: And that’s really the big question, right? It’s like Where people get investment allocation, I think, wildly incorrect, and I, I actually heard this the other day. I was just blown away. I thought, I thought I had told everybody this already, but apparently there’s somebody that didn’t hear it. There’s no sense in becoming conservative in your 50s and 60s with your money.
[00:18:10] OG: Like, you need money when you’re 60 if you’re gonna retire, and you need money when you’re 61, 62, but you also need money, the vast majority of your money is 68 to 98, right? So why in the heck would you take the only thing that you have that can outpace inflation, which is the purchasing power growth of owning companies, why would you take that away at the exact moment that you need to have purchasing power increases with your income?
[00:18:39] OG: It- It just, it defies logic.
[00:18:41] Joe: Well, this is the problem, Moji- You know? … is that, uh, I just saw a statistic a couple weeks ago, 40% of millionaires think they don’t have enough money for retirement, and while some may not-
[00:18:51] OG: Which is totally fine, so our solution to not having enough money is to have less of it?
[00:18:57] Joe: No, no,
[00:18:57] OG: no, no. Guaranteed?
[00:18:58] Joe: No. Well, actually, let me go the other way. In this study, they showed that the way that people solve that problem is by just throwing more money at it, when the true way to solve that problem is knowing how much you’re gonna need and when you’re gonna need the dollar. And it solves so many problems.
[00:19:15] Joe: And to your point, what we do is because we’re freaked out that, “Oh, I’m not sure, so I might as well buy this annuity contract that’s just gonna last for X amount of time because I don’t wanna answer the question, ‘What do I, what do I need the money for?'” Which is a hard question. It is a difficult question.
[00:19:31] Joe: But I think that when you know how much money you’re gonna need the next five years, then regardless of your age, you’re gonna go, “You know what? I’ve got money for six years on that shouldn’t be sitting in cash or sitting in a savings account.” Yeah. It should be in something longer term. Frustrating, but I think points to the biggest problem we have in retirement, which isn’t having enough money.
[00:19:51] Joe: It’s that we don’t address the question, what do I want my money for? What’s your number four?
[00:19:58] OG: Uh, number four for me is borrowing against your assets instead of selling them to fund your living expenses or something special, some big project that you have going on. You’re gonna buy a lake house, or you’re gonna, uh, do a remodel of your house or something like that.
[00:20:13] OG: This is basically using the assets that you already have to turn them into, um, additional assets, lever them, so to speak, uh, without, uh, creating a tax problem with the distribution or sale of the assets that you, um, you know, that you otherwise would have to do. Or whether it’s a tax problem with taking it out of your IRA, tax problem of taking out of appreciated stock, borrowing it is a much, much lower cost of capital, so to speak, than those things, generally speaking.
[00:20:43] OG: The downside, of course, is that you’re levering your portfolio, so you gotta be pretty, pretty conservative and, and, and have some decent risk matrices, matrices risk profiles built to, to know what you’re getting yourself into. But when used appropriately, it’s very, very, very sexy.
[00:21:02] Joe: Yeah. I remember, uh, speaking with Josh Dorkin, the creator of BiggerPockets, talking about how leverage is fantastic for real estate investors until the economy changes, and then his quote was, “It becomes a giant flushing sound of all these people” as they , the people that took too much risk, OG, uh, get flushed out.
[00:21:21] Joe: So- Yeah … you definitely need to be somebody that understands how the economy could change against you and be prepared for those instances. ‘Cause as an example right now, there are some even big-time real estate people, uh, who you’re seeing in the news are watching their fortunes go away. They did balloons, balloon payments five years ago on real estate, when real estate
[00:21:49] Joe: when, when the cost of money was very low. And now, five years later, it’s hard to come up with the capital to satisfy the balloon
[00:21:56] OG: payment. Well, in reality in, um, you know, for most commercial loans, they’re redone every five years anyway, you know? So only, only generally residential loans do you get to have for a long period of time.
[00:22:07] OG: But even so, those HELOCs or lines of credit adjust with interest rates, and we know a week or so ago, a week and a half ago, interest rates went up, so the cost of borrowing goes up there too. So yeah, leverage is awesome when it works, and very, very not awesome in a hurry when it stops working
[00:22:26] Joe: Number three
[00:22:27] OG: All right, so, uh, I get to do number three.
[00:22:30] OG: I’m gonna say, here’s one we haven’t seen a bunch of lately, but it happens from time to time: net unrealized appreciation on employer stock. Just a word salad. Doug’s head just exploded. Sorry. Doug’s like, “I’m in. That just sounds awesome.” English,
[00:22:46] Doug: please.
[00:22:47] OG: We’ll take it. If you work for a, a, a big company, maybe you have, uh, company stock inside your 401.
[00:22:54] OG: Sometimes companies will, uh, match with their company stock, and that’s, you know, what your match is. Obviously post-Enron, which for most people, they don’t even know what that is anymore, but post-Enron, you know, they have to allow you to diversify it, but some people don’t. Some people just let that sit there and grow, and they have this 25-year career, and they end up with this 401balance that is some investments and some company stock.
[00:23:18] OG: Uh, there’s a one-time opportunity that you have when you retire to, or, or when you leave that job, to take your company stock out of your 401at a more favorable tax rate than the rest- Without a
[00:23:29] Joe: penalty …
[00:23:30] OG: right, also without a penalty. So just to kind of give you some real terms here, let’s say that you’ve got a 401balance that has, uh, a million dollars in it, and of that million, 500,000 is in company stock, 500,000 is in ETFs and mutual funds, whatever.
[00:23:44] OG: Option A is you leave your job, you roll that over to an IRA, you get a million dollar IRA. Okay, everybody knows how to do that. Option B is you take the 500K that is not company stock, you put that in an IRA, and then the 500,000 that is company stock, you can do what’s called net unrealized appreciation.
[00:24:00] OG: There’s a bunch of rules with it, so tread lightly. Make sure you get a professional involved in how to do all of this, uh, calculation, especially with the timing as we get closer to the fourth quarter. But effectively, we can look at the cost basis. So let’s say the cost basis on your half a million dollar stock is 50K.
[00:24:16] OG: You know, you, you’ve put in 50, it’s grown to 500. You can take the 500 out, you pay taxes on the 50, and then the 450 is capital gains.
[00:24:26] Doug: Now I’m listening.
[00:24:28] OG: So now you basically have a brokerage account that has half a million dollars of company stock in it with a cost basis of, of 50. You will pay taxes on the 50 when you roll it out, and then an IRA of 500.
[00:24:39] OG: It just gives you some diversification options, gives you some liquidity options. You’re gonna stroke a check for $20,000, you know, because you do this. This is a taxable event, but there’s no penalty. Uh, so it works really well for early retirees, works really well for people that, uh, have a, uh, insane highly appreciated stock, maybe liquidity issues where all my money’s in my 401, that’s all I’ve been saving in.
[00:25:01] OG: I’ve got a big 401balance, but I want to retire at 53, so how do I, you know, get some money from 53 to 59 and a half? So there’s a lot of use cases for it. There’s also times where we see people wanting to do it where it doesn’t make any sense. If you’ve been rebalancing your portfolio over time, and your company stock is not a huge gain Then all you’re doing is taking qual- You know, let’s say that the, let’s say in this example, your qualified plan stock is $450,000 as a cost basis, and you say, “Well, I want to do this.”
[00:25:30] OG: Well, you’re gonna pay taxes on 450 grand right now
[00:25:35] Joe: Not a great idea
[00:25:37] OG: Not awesome.
[00:25:38] Joe: Yeah.
[00:25:38] OG: And there’s a bunch of other rules around, like, the timing and what else has to happen. It’s a one-shot opportunity. You can… You get one, one opportunity to do it. So basically, the moral of the story is, if you have company stock in your 401and you’re leaving your job, just hit pause for a second.
[00:25:55] OG: Just go, “Whoa, I might have something else going on here that, that might be attractive.”
[00:26:00] Joe: This is one of the few strategies that, for the right person, could save them six figures in taxes.
[00:26:07] OG: Yeah, over your lifetime, yeah.
[00:26:08] Joe: Yeah, could legitimately save just a ton of money. Where my municipal bond one, which was my number five, is, I think, a good one, but, you know, you’re going to, uh…
[00:26:18] Joe: Well, I guess you’d make up… If you don’t do the municipal bond strategy, you’ll make up potentially over your lifetime w- w- way more than six figures. But even using municipal bonds probably won’t give you six figures of tax savings. Could, if somebody’s a bajillionaire. My number three is, uh, what we call, uh, 72t distributions, and this is again for an early retiree.
[00:26:44] Joe: If you’re somebody that has saved again all of your money into, uh, your 401or the majority of your money in your 401, you wanna go before 59 and a half or 55 if your plan allows you to get at the money in your pre-tax accounts by age 55, which applies to some people. If you wanna go before then, then you take your money and you turn it into a pension for five years or until 59 and a half, whichever is longer.
[00:27:13] Joe: I see people ask about 72t all the time, and what’s frustrating, OG, about 72t isn’t at the beginning. It’s at the end of the 72t, and this is where the problem comes in and why I have it on my list of esoteric things because, you know, you begin this at age 50, let’s say, and how many of us have had changes over a five-year period that we could not predict?
[00:27:37] Joe: And so setting up this pension-like distribution at age 50 and by 55 we’re going, “Oh, man, I wish I’d done that differently,” I think happens a fair amount. So a good way to do this is to do almo- almost like companies will do minimum viable product. They will, when they first release it, they will make it just barely viable, and then they’ll add onto it based on what people buy.
[00:28:01] Joe: I think doing this pension-like distribution from your, your retirement plans at age 50, just enough to get by, and then as life changes, deciding if you wanna go bigger is the way to do it. But still, I think an esoteric strategy that works for a giant subset of people, but for the right person, you wanna go early, could be life-changing
[00:28:24] OG: Yeah, another one of those complicated tax distribution schemes, and we hear the word scheme and it sounds bad, but it is, you know, it can be bad.
[00:28:33] OG: Uh, where you need to know all the facts before you go into it because, you know, once you start this, you’ve gotta largely keep it. There’s some outs, but not very many, and there’s some modifications, but not very many. So you have to know what you, know, know what you’re getting yourself into for how long.
[00:28:49] Joe: Y- you and I have talked a lot about go ahead and mess things up. You’re gonna learn from it, and it’s not irrevocable, right? This is irrevocable. This is, this is that thing that you, you 100%- I
[00:29:02] OG: definitely do think it’s irrevocable, yep.
[00:29:05] Joe: Irrevocable- … I think is the word. Number two My number two is cash value life insurance as a savings vehicle, which we may have heard from you before, OG.
[00:29:17] Joe: And I think if you’re gonna do this, and, and I’m not gonna belabor the points, ’cause you made all of them earlier in this piece, except for I’m gonna lay it on a little on this piece. If you have saved everywhere else, you- you’ve maxed out any Roth IRA that you’re eligible for, you’ve done the pre-tax stuff, you’ve put money in other places, I like loading up a cash value life insurance policy better than putting money into an annuity.
[00:29:47] Joe: I think it’s less of a tax trap. I think it’s actually easier once you get your arms around it to understand. I like the idea of it being tax-free money potentially versus tax deferred, but this has to be… I remember one of the few times I used this in my career, this is 15 years ago, OG, and they were making $400,000.
[00:30:09] Joe: So now we’re talking about somebody making a million dollars a year, right? A million dollars of income a year. They are stuffing everything as far as they can. All their goals are met. They were fairly frugal people. How do we avoid taxes on this money? Cash value life insurance was right, but think about what a subset of our stackers are hearing this going, “Oh yeah, that’s me.”
[00:30:30] Doug: So of two sucky choices, it’s the less sucky one.
[00:30:33] Joe: It’s the less sucky- … of the two sucky choices.
[00:30:35] OG: And I would say that absent an actual insurance need on top of that, I would just use a regular brokerage account.
[00:30:41] Joe: Yeah.
[00:30:42] OG: Like, I, I would need to have a really, really, really profound insurance need on top of it to be in the ballpark of, of using it.
[00:30:50] OG: And then there’s another piece to this too. The other piece is if you do use it, you have to go through a low-cost provider, because there is such a, um, I think Doug would call it a butt load, of commissions and fees and charges and stuff that’s just stuffed in there that’s really getting after you, that, um, again…
[00:31:14] Joe: Yeah. ‘Cause the goal, because the goal that you’re talking about is to beat the tax rate. The goal is to beat the tax rate, and if the insurance char- Like, I don’t care who I give the money to. Do I give it to the IRS? Do I give it to the insurance company? I wanna do the one that’s less. I wanna do the one that’s less.
[00:31:28] OG: Yeah, a- assuming that the, that the liquidity is the same, sure. Assuming that the investment choices and costs are the same, sure. There’s more to it than just the insurance cost in my opinion, but, um, yeah.
[00:31:40] Joe: Yeah.
[00:31:41] OG: I, I, this is such a small number of people. The number of people who should be doing it versus the number of people who actually do it is off by a order- Painful
[00:31:48] OG: of magnitude of 10,000.
[00:31:50] Joe: Painful. Yeah. Far more people doing this than should be doing it, which is why it’s my number two. Yeah. Incredibly esoteric. Less esoteric than it should be. What’s your number two?
[00:31:59] OG: Uh, number two for me is exchange funds for diversified stock purposes. Oh. So an exchange fund Is let, let’s say, for example, that you have a million dollars of AMD and the rest of your portfolio is $100,000 of Vanguard Total Market.
[00:32:19] OG: Like, you just have one stock, right? And the problem with diversifying it is, uh, you just don’t feel like writing a check for $250,000 to Uncle Sugar to pay your tax bill, right? ‘Cause AMD’s gone up, and off we go. So an exchange fund is basically a product, there’s a handful of companies out there that do them, where you can combine your AMD with Doug’s General Motors and Joe’s Apple and OG’s Caterpillar, and we all get together and put in all our million dollars of stuff, and we basically create ourselves a diversified mutual fund or a diversified ETF, if you wanna think of it that way.
[00:33:00] OG: So my contribution to the ETF is AMD, yours is Nvidia, the other guy’s is General Motors, and you can see if we all had different walks of life, we could basically pull this thing together and create a diversified ETF. There are some rules around it. The first rule is, uh, 20% has to be something that’s non-traded, so basically private real estate.
[00:33:21] OG: Second rule is it’s gotta be there for seven years. And the third rule is, is that there’s really not any tax savings to this strategy. You’re basically getting diversification strategy or diversification benefits, I should say. At the end of this seven-year term, you can keep the fund, and you just keep benefiting from the fund as it is.
[00:33:40] OG: Or you can say, “I’m out. Give me back my accumulated value,” and instead of getting AMD back, you would get your 35 or 40 positions of a diversified portfolio with your original cost basis. So you don’t save any money on taxes here. This is just a diversification play. It’s fairly locked up for seven years, so there’s some issues with that.
[00:34:02] OG: It’s, uh, there is a little bit of a cost structure to it. It’s not obscene, but there’s some. Um, and of course, it’s market-based, so if you say, “Well, wait a second. In seven years from now, my AMD stock would’ve made me worth $30 million, but this thing only made me worth 10. You know, what the heck?” That’s the trade because somebody else’s GM would’ve made them worth zero, but instead they’re worth 10.
[00:34:26] OG: This is the gamble that you’re playing is: Have I built enough net worth that I’m okay with just slowly all ships rise in the tide, or do I need to still stay concentrated to, uh, you know, to benefit from that? So exchange funds, again, very subset of people But cool as hell when you use them.
[00:34:47] Joe: But yeah, I was, I was thinking, wow, it’s fantastic
[00:34:49] OG: Double sexy time.
[00:34:50] Joe: They can be fantastic. But to your point, every investment has an Achilles heel. Yep. And you gotta go in knowing what the Achilles heel is. This is y- y- you know, it’s almost like selling covered calls. I’m giving up the upside. I’m giving up the upside. If I’m selling covered calls, I get the- Oh,
[00:35:07] OG: and you lower your tax basis.
[00:35:09] Joe: Right. Right. Yeah.
[00:35:10] OG: Like, there’s no free lunch, man. Like, anybody who, like, thinks that there’s a free lunch in any of this stuff, there’s not. The question always has to be, how do I die? So how does this end badly for me, or how do I get pissed off?
[00:35:23] Joe: Always.
[00:35:23] OG: There’s, there’s gonna be something in there, like any product.
[00:35:26] OG: You know, you say, “Well, that’s not true for Vanguard.” Sure is.
[00:35:29] Joe: 100%.
[00:35:31] OG: It’s there.
[00:35:32] Joe: Number one. Oh, gee, what did you go, you know what, this has gotta be at the top of my list?
[00:35:37] OG: Again, I’ll say I did not, uh, rank any of these. I just, I’m just reading them in the order that I had, uh, written them down, with some slight modifications to adjust to your cash value, uh, life insurance fund.
[00:35:47] OG: Uh, my last one is also around diversification of, of highly appreciated stock, and this is using … I wrote charitable remainder trusts. What I think we should just kind of pivot to is using complex estate planning strategies to avoid estate taxes today, avoid estate taxes in the future, avoid income tax or capital gains tax on highly appreciated assets.
[00:36:11] OG: Th- this is, this is the .1 of the .1% type of stuff. It can make a huge difference. Your, you said earlier about, like, some of these things can save, like hundreds of thousands of dollars. This is another example of that. Using complex charitable strategies around highly appreciated company stock, even if you’re, it’s your own company, you know, you can do it, is very, very, very attractive.
[00:36:35] OG: It has an insane amount of costs around it for compliance, record-keeping, tax filings, attorney fees, all that stuff. And believe you me, those people are getting their bite of flesh out of this deal. This isn’t something you’re doing for a $300,000 stock account. This is something that you do for a $22,000,000 stock account when you also have another $22,000,000 stock account next to it.
[00:36:59] Joe: Yeah.
[00:37:00] OG: I wrote charitable remainder trust, you know, for highly appreciated stock, but charitable strategies or complex estate planning
[00:37:05] Joe: strategies- A charitable remainder trust, by the way, we should define what that is. You’re moving your highly appreciated stock over to a charity because of five- A trust
[00:37:14] OG: account.
[00:37:15] OG: Yep …
[00:37:15] Joe: partially because a 501[c][3], which means the IRS qualifies them as a charitable institution, isn’t gonna pay any tax on that account. So rather than giving them cash, you are giving them the highly appreciated stock
[00:37:27] OG: Yeah, I mean, effectively a charitable remainder trust is a trust account. You put your stock inside of a trust account.
[00:37:33] OG: The trust is then obligated to pay out the remainder, the rest of it, to a charity at some date in the future. In the meantime, you get a stream of income off of the portfolio. You set up what that stream is. It’s some- there’s a factor that the IRS maintains based on the duration and the time, and there’s a calculation that they say, “Okay, you can take out X dollars.”
[00:37:53] OG: For example, let’s say that you had $10 million of Nvidia in addition to a bunch of other money. You could say, “Well, I’ll put 10 million in this charitable remainder trust. It’s gonna kick out to me $500,000 a year of income. That’ll be taxable to me in small doses. And then at the end of this 20-year period, let’s say, whatever’s left in the account is gonna go to the charitable organization
[00:38:16] Joe: of my choice.”
[00:38:16] Joe: And that’s where the remainder piece comes in. Yeah.
[00:38:18] OG: Yes.
[00:38:18] Joe: Makes it different than putting money in a donor-advised one. My number one appeared earlier on your list, and that was the one I thought could, for the right person, which is a sub, sub, subset. I tried to do these by in order of what’s more esoteric and what also saves people money, and that was that unrealized appreciation.
[00:38:38] Joe: When I saw this work with an executive for the first time ever back in the early 2000s, an executive who worked at Pepsi, they had $800,000 of Pepsi stock in their $2 million 401plan, and we were able to take that $800,000 out of the 401, where a previous advisor had recommended they roll it over. And this guy had been doing it his entire- Mm-hmm
[00:39:03] Joe: 35-year career, been putting money into Pepsi stock. It was so appreciated. There was so much tax that he avoided by taking that money out, and yet how often did I see it during my entire career? Maybe four times. That unrealized appreciation, only if you’ve highly appreciated stock, can make a lot of difference.
[00:39:25] Joe: Well, even if that didn’t help you today, Stackers, I hope you get into the position, because a lot of these are high net worth strategies. I hope at some point you’ve a high enough net worth where one of these apply to you. But until then-
[00:39:37] OG: I know …
[00:39:37] Joe: yeah. Me
[00:39:38] OG: too.
[00:39:39] Joe: Especially when it applies to, especially to the insurance products we talked about, a lot of these strategies are sold to people that they really don’t apply to.
[00:39:50] Joe: So hopefully you also learned enough today for buyer beware. All right. Normally at the halfway point of every show, we do the financial basics, but you know what? Today, it’s a little later in the show, and I can see Doug pacing in the background. You can sit down, Doug, because it’s time for Doug’s trivia.
[00:40:07] Doug: Finally. Hey there, Stackers. I’m Joe’s mom’s neighbor, Doug, and don’t you love Good Neighbor Day? Doing little things other people appreciate. Like one time, I returned a rental car with a full tank of premium gasoline. I know, I’m a giver. And speaking of going above and beyond, let’s talk about Ted Williams, because on this date in 1941, Teddy Ballgame entered the final day of the baseball season with a double header ahead of him and a batting average sitting right around 400.
[00:40:38] Doug: And I mean right around it. Williams was actually batting .39955, which Major League Baseball would have happily rounded up to 400. He could have called in sick to work that day to protect that number. No, no, no. Instead, Williams played both games of the double header. He didn’t know it at the time, but he was chasing something nobody in Major League Baseball has accomplished since: hitting 400 for an entire season.
[00:41:07] Doug: So here’s your trivia question. Ted Williams came to the plate eight times that day. How many hits did he get, and was it enough to finish the season at 400? I’ll be back with the answer right after I donate these three AOL CDs I found to the local library. Somebody’s about to score a month, a whole month, of free dial-up on old Dougie.
[00:41:31] Doug: You’re welcome, America.
[00:41:36] trivia bit: We’re looking for the answer and correct spelling. Old MacDonald had a what? Farm. E-I-E-I-O.
[00:41:48] Doug: Hey there, Stackers. I’m chronically amazing neighbor and guy who once let someone merge in construction traffic. Still waiting on a thank you note, buddy. I mean, even a little wave woulda… Anyway, it’s Joe’s mom’s neighbor, Doug. Baseball season still has a few games left in the regular season this year, but back in 1941, this was the final curtain, the final day of the season.
[00:42:12] Doug: Ted Williams could have protected his .400 average by untying his cleats and then opening a beer, but Teddy knew the truth. His average was actually .39955. Baseball would’ve rounded it up to .400, but apparently Ted Williams wasn’t interested in backing into history books on a technicality, so he played both games.
[00:42:32] Doug: He came to the plate eight times. I asked you how many hits did he get, and was it enough to really finish above .400? Well, Teddy Ballgame didn’t just protect that average. He went six for eight. That pushed his final batting average all the way up to .406, and more than 80 years later, no baseball player in Major League history has finished a season at .400 since.
[00:42:57] Doug: Wow, what an honest guy. I shouldn’t brag, but I’m wired, you know, pretty much the same way as Teddy Ballgame. There was this one time I checked out of a Holiday Inn, left a couple of ice cubes in the bucket for the next guest. Didn’t leave a note. Didn’t ask for recognition. I just walked away. I’m sure you’ll agree, of all my incredible qualities, you’ll find humility and service to others at the top of the list.
[00:43:20] Doug: So feel free to share that trivia with your friends, but now let’s get back to Joe and OG.
[00:43:26] Joe: Dude, you are such a giver
[00:43:28] Doug: And you know, it’s, I don’t even know I’m doing it half the time. It’s just w- it’s the way I’m
[00:43:32] Joe: wired. It’s just built in, like Mother Teresa.
[00:43:33] Doug: Yeah. Yeah. And let that be a lesson to everybody else.
[00:43:37] Doug: Be like Doug.
[00:43:38] Joe: Yeah, 100%. It is amazing, and I love hearing stories like that, Doug, and I know that all our Stackers aren’t baseball fans, but this guy knows that, “You know what? This truly is not gonna be the number.” And so he goes out there and goes, “Nope, we’re gonna make it the number.”
[00:43:55] Doug: Well, yeah. And y- you know, for so many great sports stories, the reason we love them is there’s a romanticism to whether it’s football or baseball or anything.
[00:44:05] Doug: I personally think baseball’s the most romantic sport out there. But it’s the, it’s the human side of it, and it’s knowing that’s just how this person was wired. “No, we’re gonna do this, and we’re gonna be real, and whatever it ends up being is what it’s gonna end up, and I don’t, you know, I don’t, I’m not doing this just for the number or for the record.
[00:44:23] Doug: I’m here to play baseball, and let’s get after it.” There’s a lot of lessons there, and there’s a lot of heart- heartwarming stuff you can glean from stories like this, and I would recommend reading the full version of the story and kind of the discussion between he and his manager. It’s pretty amazing.
[00:44:38] Joe: It is funny because the original story was the manager talked, was trying to talk him out of- Yeah
[00:44:44] Joe: playing that day. However- Exactly … but y- yeah, but since then, the manager actually denied that. He goes, “I did not. I did not try to talk him out of it.” Maybe he didn’t wanna be on the wrong side of history or the wrong side of that story.
[00:44:55] Doug: Exactly, once he saw how it turned out.
[00:44:58] Joe: That’s right. Yeah. Yeah. Yeah, I wanted to be on the right side of that.
[00:45:01] Joe: Let’s wander out on the back porch because we’ve got quite a few things. Number one is, you know, OG, I know that, uh, believe it or not, you’re not on TikTok, the way that you talk so fondly about TikTok. But I often find, I often find fantastic stuff on TikTok. We talk a lot about problems people have in retirement and about how often we’re solving for the wrong things in retirement.
[00:45:25] Joe: On the Huberman Lab podcast, they were recently talking about advice from an 84-year-old who is incredibly successful, and this is just a little clip of that
[00:45:37] tiktok: James Hollis came on my podcast, 84 years old, surprised the out of me when he said, “Here’s how you have a great life. It involves four things. The first three are shut up.”
[00:45:47] tiktok: That’s the first one. I go, “Shut up?” And he goes, “Yeah. Someone’s always got it worse than you. Nobody wants to hear you whine. Have gratitude for what you do have. If you’re alive, you got something to be grateful for.”
[00:45:56] Doug: Mm.
[00:45:56] tiktok: Second is suit up. What is suit up? Suit up is you have a role to fulfill each day, for other people and for yourself and for the world.
[00:46:04] tiktok: Suit up is get prepared. Shower, organize your room. We’ve heard this stuff from Jordan and from other people, but get your act together so that you can then do the third thing effectively, which is show up. Go find a role in life and fulfill it. Might not be the role you fulfill your entire life, but if it’s a summer camp counselor, if it’s a babysitter, if it’s a, a nanny, if it’s a firefighter, if it’s…
[00:46:25] tiktok: Whatever you, you are doing at some point in life, you, in order to have confidence and be a healthy, happy person.
[00:46:31] Joe: I found that incredible, no matter what you think about Huberman, that, uh, this advice from an 84-year-old OG. You know, we talked earlier about so many people don’t wanna talk about what’s the meaning of life, and yet when you serve other people, you find your role, you quit complaining.
[00:46:47] Joe: You talk a lot about your grandfather about this, about your, your grandfather very fondly. It s- seemed to me being this type of a person.
[00:46:55] OG: It seems that there’s some common themes on, you know, these people that live happy lives, right? And maybe, uh, if you see the theme repeating itself over and over and over again, maybe you ought to kinda, I don’t know, take notes.
[00:47:11] OG: You know?
[00:47:12] Joe: I think it is easier as you get older to go, you know, “Woe is me,” and look at me and to focus internally. And I find that every time I focus internally on what suits Joe, the worse things seem to get. Like, like we live in the… We live at one of… Joseph Moore, the historian, talked about this. We live at a time, OG, when people are richer than ever.
[00:47:34] Joe: We have more access to fun stuff. We have more access to money. We have more access to the ability to make ourself happy, and yet you look at the epidemic of people who are chronically depressed today I think we’re, we’re in our own head far, far too much. I think that that brings up something that is a challenge that I have, Stackers, for all of you.
[00:47:59] Joe: I think that this idea also of community, finding a role and, and, and, and filling it and serving other people. So many people that listen to the Stacking Benjamins show are good with money or at least intentional about money that my challenge would be, get a group of people together in October and chat about your goals for 2027.
[00:48:21] Joe: I think if you, in October, can get a group of people together at a coffee shop, at somebody’s house, wherever it is, and begin talking about 2027 right now, you’re gonna have a much better 2027. And I think that’s part of shut up, get out of your head, go find a role and fill it But also find a good group of people together
[00:48:43] Doug: I’ll make it even easier.
[00:48:44] Doug: It doesn’t even have to be a huge group. Find one person.
[00:48:47] Joe: One person.
[00:48:48] Doug: Yeah. Find one person that you can say out loud, “Here’s something I want to accomplish in the year.” And hopefully it’s not somebody who will roll over when you bail on it in February.
[00:48:58] Joe: It is so important to say it out loud, at the very least, number one, but number two, to have that person, Doug, that pokes you and goes, “What are you doing?”
[00:49:06] Joe: Yeah.
[00:49:07] Doug: Super- Yeah, you can stop poking me, by the way
[00:49:11] Joe: He’s like, “It’s October, I’m not gonna do it.” Doug said he was swearing off donuts. Didn’t happen.
[00:49:17] Doug: No. You picked the wrong example. Everybody knows by now I’m not a sweets guy, I’m not a donut guy. But if you said, “No more lasagna for you,” I’m out.
[00:49:25] Joe: It’s… Yeah, bad deal.
[00:49:28] Joe: Last, if you’re somebody that cares enough about coaching people that you officially are a coach or you have thought about becoming a financial coach, OG and I have a new program where we are coaching coaches. And if you wanna chat more about how we coach coaches and what that program looks like, we’re not looking for a ton of people, but we are opening up the doors.
[00:49:53] Joe: Just go to this link, stackingbenjamins.com/coaching, stackingbenjamins.com/coaching, and, uh, we will set up a meeting, you and I, to chat more about your coaching program, what you’re looking for, and if being a part of our cohort to challenge you for a bright 2027 coaching year, I think is gonna be, gonna be great.
[00:50:15] Joe: Really looking forward to working with a bunch of coaches. I love the idea, OG, that we’re getting the word out, that we’re helping these people that wanna be people that increase financial literacy in the country. If we can, if we can inspire them to go bigger, do more, share with them some of the mistakes you and I made in the past along the way so that you don’t make those same mistakes, I think it’s gonna be great.
[00:50:36] OG: Well, you can share your mistakes. I don’t make any of them.
[00:50:39] Joe: Yeah, that is an important point. If I share my mistakes and OG’s perfection, I think- There you go … and that’s why we’re- That’s a
[00:50:45] OG: pretty good combo.
[00:50:46] Joe: Yeah, it’s why we’re a good team. I make the mistakes, he never does. Speaking of mistake, I often think it’s a mistake at the end of the episode- A bunch of
[00:50:56] OG: tequila last night was a mistake
[00:50:58] Joe: I of- I often think it’s a mistake at the end of the episode, but I still ask it anyway. Doug, what are the things we should have
[00:51:04] Doug: learned? Fine. Fine.
[00:51:07] Joe: Maybe I could be a better neighbor. I saw this- I need to learn to be a better
[00:51:10] Doug: neighbor … I saw this train rolling at me for, like, the last 60 seconds. He’s gonna, he’s gonna come right down at me like I’m the mistake.
[00:51:18] Doug: Okay, fine.
[00:51:19] Joe: You’re not the mistake. It’s just a mistake to ask. Maybe a mistake. I don’t know. What’d you come up with today, Doug? What’d you come up with?
[00:51:25] Doug: Well, they’re all probably wrong, but let’s give it a shot. Well, Joe, first take some advice from you and OG. While it’s usually best to stick to the tried and true, there are times when that esoteric strategy is a perfect fit.
[00:51:39] Doug: Hopefully today, you found a few that you can now see can fit in the right situation.
[00:51:44] Joe: All right. That’s a good one. You’re rolling.
[00:51:46] Doug: Oh. That’s good. Well, thank you. Well, let’s see if I can make it two for two. Second, an insurance salesperson telling you that a complex strategy will solve all of your problems, eh, calculate the ROI carefully before handing over your hard-earned money.
[00:52:00] Doug: Whether it’s an annuity or life insurance contract, they can work, but far less often than they’re sold to unsuspecting investors. How’d I do?
[00:52:09] Joe: That’s even better.
[00:52:10] Doug: All right. Let’s see if we can do a little, uh, Ted Williams here. But the big lesson, don’t wait by the mailbox hoping someone’ll notice what a great neighbor you’ve been.
[00:52:21] Doug: These people are all too busy navel-gazing to notice the brilliance around them. Check this out. I just gave Joe’s mom’s other neighbor some grass seed I had left over. Seriously, there must’ve been, like, a dozen seeds left, and they said absolutely nothing. Nada. No thank you. Silence. No witty card, no Starbucks gift certificate.
[00:52:42] Doug: Miss Manners would be horrified, pal.
[00:52:45] Joe: Well, two for three’s not bad.
[00:52:48] Doug: This show is the property of SB Podcast, LLC, copyright 2026, and is created by Joe Saul-Sehy. 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.
[00:53:06] Doug: 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 Benjamins show.
[00:54:24] Joe: Guys, I went and saw a movie over the weekend. Got home from FinCon, Cheryl’s like, “You wanna go see a movie?” I’m like, “Absolutely,” because my brain is fried and I just need to be entertained. And the movie we saw was called Runner.
[00:54:40] bit: You’re Hank, aren’t you? You’re the delivery man. But this is not a FedEx package. There is a little girl that’s very sick, and you’re delivering her new liver. If she doesn’t get this today, she’s not gonna make it. Let me
[00:55:00] bit: ask you a question. How much does one of those go for on the black market?
[00:55:04] bit: Oh, a million maybe.
[00:55:05] bit: A
[00:55:05] bit: million?
[00:55:08] bit: Go, go,
[00:55:12] bit: go!
[00:55:16] Joe: And at this point it’s a bunch of sound effects, Doug, so I’ll stop it right there, of people getting, uh, beaten up, shot, shots fired, uh, car wrecks, explosions.
[00:55:26] Doug: So it’s a comedy?
[00:55:28] Joe: Kind of. It is by Angel Studios. If you’re not familiar with Angel Studios, I generally don’t care what studio makes a movie, except now if it says Angel Studios, I’m much more likely to go see it.
[00:55:41] Joe: Because Angel Studios, initially I thought that this was either a political or religious agenda where they’re like, “No, no, no. We’re gonna make movies that we can all agree on.” So a couple Angel Studios movies I saw recently, I saw Young Washington, which is about the early part of George Washington’s career.
[00:55:58] Doug: I heard that was really good.
[00:55:59] Joe: Sensationalized, but really good. My favorite Angel Studios movie was, uh, uh, Mother Cabrini about the Cabrini Order of Nuns and in New York- That was a while ago. Yeah. Wasn’t
[00:56:10] Doug: it?
[00:56:11] Joe: In New York City. Uh, Kevin… Who’s the guy from King of Queens?
[00:56:17] Doug: Kevin Hart
[00:56:18] Joe: Nope. Kevin Hart , Kevin Hart is the short, really funny guy.
[00:56:21] Joe: Uh,
[00:56:21] Doug: Kevin Bacon.
[00:56:22] Joe: Not Kevin Bacon.
[00:56:23] Doug: Kevin O’Leary.
[00:56:24] Joe: Kevin. Kevin James was in a romantic comedy recently by them. These movies are all over the place. Of course, the one that I saw that I really loved about the women in Iraq who were going to, uh, learn computers. She was teaching them computers, and that was a real story.
[00:56:41] Joe: So sometimes real, sometimes not. This was not. This starred, you heard Owen Wilson as this chatty guy who’s delivering a liver, and, uh, th- and this is the awesome part. The guy who’s the star of Reacher, Alan Ritchson, who plays Reacher, is the runner, and he’s the guy that has to deliver the liver and Owen Wilson successfully.
[00:57:06] Joe: And it turns out that the cartel really wants this liver as he’s trying to deliver it. This is, man, if you like action movies, this is a fantastic action movie, and I like the fact that the stakes are stakes that I really care about. It’s funny with Owen Wilson and Alan Ritchson having these- That’s
[00:57:23] Doug: actually why I asked the question.
[00:57:24] Doug: When I heard Owen Wilson’s voice, I immediately thought comedy.
[00:57:27] Joe: Oh, yeah, having these great back and forths. Owen Wilson has some great lines. The story has some super high stakes in it. The stakes are different, of course, than you think they are going in. If you want a movie that’s never gonna win an award but has a ton of stuff blowing up, is still very funny and heartwarming at the same time, Angel Studios did it.
[00:57:47] Joe: I, I loved The Runner. You guys are both gonna love The Runner. What a great movie. So go see The Runner.
[00:57:53] Doug: I haven’t seen… I don’t know if this is an Angel Stu- ’cause I know Angel Studios is pushing their own streaming service. Yeah. So maybe this is part of their strategy. If you
[00:58:01] Joe: don’t see them in the theater, it’s hard to
[00:58:03] Doug: see
[00:58:03] Joe: them.
[00:58:03] Joe: Yeah.
[00:58:04] Doug: Right, ’cause I’ve been looking for Cabrini ever since you told me about it, and it’s just not available on the 11 different streaming services I subscribe to, and I’m not gonna pay for another one for the one movie.
[00:58:16] Joe: My friend Mike has a thing called Plex-
[00:58:20] Doug: Mm. Yeah …
[00:58:20] Joe: which allows you to do all these different things.
[00:58:23] Joe: So he s- he sees Angel Studios movies through Plex. Outside of Plex, I can’t find them anywhere, unless you’re gonna pay for the Angel Studios’ own deal.
[00:58:33] Doug: Through Plex, does he then still have to, for things that are outside of Plex, does he have to pay the 4.95 to watch Cabrini or, or is it all included, do you know?
[00:58:44] Joe: Cabrini was included, so he ended up watching it for just- Okay … the Plex fee. The answer to that is I don’t know ’cause like you, I, I don’t wanna look into Plex. I don’t want another- Yeah … I don’t want another streaming service
[00:58:57] Doug: Well, and well, and it’s sort of like Amazon. Well, oftentimes I’ll search for a movie you recommend, and it’ll initially make it look like it’s on Amazon, which I pay for, and then I go there and it’s, you gotta buy the movie or- Yeah
[00:59:11] Doug: rent the movie. And I don’t know why that’s a small barrier entry. OG’s just shaking his head right now like, “Dude, it’s $4. You can afford it.” It’s the principle, honestly. As…
[00:59:20] Joe: Well, as this comes out, uh, I like the theater experience better, just the big screen, and especially for an action movie. It was, uh, so fun to watch on the big screen.
[00:59:29] Joe: I think that while it’s still there, go catch Runner.
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