Pop quiz: If your health insurance premiums keep climbing, should you just go catastrophic and pocket the savings?
Joe Saul-Sehy, OG, and CFP Anna Allem tackle that exact question, along with a handful of other money decisions that keep Stackers up at night. From navigating healthcare coverage gaps to figuring out when (and how) to withdraw from a 529, this Monday mailbag episode is packed with the practical advice you need, served with the basement humor you’ve come to expect.
The health insurance conversation gets real: what catastrophic plans actually cover (spoiler: less than you think), how to plan for the gaps, and whether gambling on your health is ever a smart financial move. Then Anna breaks down the 529 withdrawal strategy that saves you headaches at tax time, and the crew tackles a listener who’s spooked by market volatility and wondering if it’s time to bail.
But it wouldn’t be Monday without some chaos—Joe’s cat decided to add drama to the morning, Doug brings trivia about counterfeit currency (because of course), and the gang updates you on the charity challenge where Stackers can support financial literacy and maybe win some prizes in the process.
Plus: OG delivers movie reviews to help you figure out what’s actually worth your streaming time this week.
What You’ll Walk Away With:
• The truth about catastrophic health plans—when they make sense and when they’ll leave you exposed
• How to handle healthcare coverage gaps without gambling your financial future
• The smart way to withdraw from a 529 so you don’t accidentally trigger taxes or penalties
• Why market volatility isn’t a reason to panic—and what to do instead of bailing on your portfolio
• How diversification and rebalancing keep you sane when the headlines get scary
• A reminder that financial planning (like cat wrangling) rarely goes exactly as planned
This Episode Is For You If:
• You’re staring at rising health insurance premiums and wondering if there’s a better way
• You’ve got a 529 but aren’t sure how to actually use it without screwing up
• Market dips make you nervous and you want to know if you should be doing something
• You’re tired of generic financial advice and want real answers to your specific questions
• You believe learning about money should involve at least a few laughs (and maybe some cat stories)
Got a Question for the Basement?
Drop it in the comments or send it our way—you might just hear Joe Saul-Sehy, OG, and Anna tackle it in an upcoming mailbag episode. And if you want to support financial literacy while competing for prizes, check out the charity challenge details in the show.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
Monday Mentor: Anna Allem

Big thanks to Anna Allem for joining us today. To learn more about Anna and how she can help you with your plan, visit Fall 2025 Call Booking Campaign.
Doug’s Trivia
- What’s the most counterfeited denomination of U.S. currency?
Have a question for the show?
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- Check out The 201, our email that comes with every Monday and Wednesday episode, PLUS a list of more than 19 of the top money lessons Joe’s learned over his own life about money. From credit to cash reserves, and insurance to investing, we’ll tackle all of these. Head to StackingBenjamins.com/the201 to sign up (it’s free and we will never give away your email to others).
Other Mentions
- Expanding Access to Health Insurance: Consumers to Gain Access to “Catastrophic” Health Insurance Plans in 2026 Plan Year (Centers for Medicare & Medicaid Services)
- Home – my529
- Gifting Sense® – Early Financial Education
- Donate to “Stacking Hope: Creating Financially Literate Children”, led by Stacking Benjamins
Join Us Wednesday
Tune in on Wednesday when we’ll talk about intentional listening, staying focused, and accomplishing more so YOU can stack more Benjamins with our Wednesday Mentor, executive coach Katie O’Malley.
Written by: Kevin Bailey
Miss our last show? Listen here: GREATEST HITS WEEK: Why You Feel Broke Even When You’re Doing Everything Right (SB1761)
Episode transcript
[00:00:00] Joe: It is Monday morning in Texarkana. And you know what? I just got back from taking the cat to the vet and you know how boy are [00:00:06] OG: my arm tired? [00:00:09] Joe: Wrong joke. Almost nailed it. Almost nailed it. But the poor guy, he’s 15 years old and uh, he’s freaked out by all the construction, so he stopped grooming himself. We had to talk to Doug about that before, by the way, about grooming himself. [00:00:23] Joe: But, uh, he’s got these rat’s nests on his belly that we can’t get out. So he’s very unhappy with me right now. So I came here to make friends. Oh gee, [00:00:34] OG: okay. Can’t have Cooper mad at you. It’s a bad day. It is a, that is, he can ruin your life in more ways than you can imagine. [00:00:42] Joe: He, he has before. [00:00:43] OG: He’s like, new floor. [00:00:46] Joe: I have a solution to this. I think I’ll [00:00:47] OG: claim this little section right here, as a matter of fact. [00:00:50] Joe: Did I tell you about we, we always get him help. Now he needs medicines and stuff because he’s, he’s an old guy. Mm-hmm. But, uh, before that, we used to be able to leave him for two days, maybe three days. Did I tell you what happened? [00:01:02] Joe: Og When we tried to leave him for four days, [00:01:05] OG: no [00:01:05] Joe: one time, we left him for four days and just gave him a bunch of food, a bunch of water. He was fine. Everything was there. Uh, he, we come in the front door after being on this long weekend trip, and he just looks at us. He star, he’s, he’s like the angry mom when you’re home, past curfew, like 20 minutes late. [00:01:23] Joe: You know how mom gets [00:01:25] OG: Yeah. I’m not mad. I’m just disappointed. [00:01:26] Joe: Exactly. And he just starts, he just starts meowing in a way that is clearly bitching at me, just completely complaining at me. And then he walks away. And then my cat, who has never done this before and never done this since. Takes a shit on my pillow. [00:01:46] trailer: Yeah, [00:01:46] Anna: no. [00:01:47] Joe: Right in the middle of my pillow. And it was message received, Cooper message received. From then on, if it was more than three, that would [00:01:56] OG: be, yeah, we, we would find a new place for the kitty. [00:02:00] Joe: Yeah. [00:02:00] Anna: Kitty would need to go to a farm. [00:02:01] Joe: Well, he was gonna find a new place for us. [00:02:04] OG: Yeah, yeah, yeah. [00:02:07] Joe: That’s so bad. [00:02:09] Joe: All cat lovers said you hate mail too. OG and Anna. Well, on that note, [00:02:15] OG: I mean, they go sometimes, right? I mean, it’s, [00:02:17] Joe: yeah. You know, [00:02:18] OG: it happens. Our cat was 19. [00:02:20] Joe: Night. That man. That’s old. [00:02:22] OG: Yeah, [00:02:22] Joe: that’s great. That’s a, that’s life. Well lived right there for a cat. You know it’s life well lived when you can play all weekend and the men and women of our armed forces are taking care of [00:02:31] OG: us. [00:02:31] OG: Your biggest concern is your cat. [00:02:32] Joe: Right? Exactly. [00:02:33] OG: Not the security of the nation. [00:02:35] Joe: I don’t have to worry about that at all. So why don’t we salute our troops, everybody, like we do on Mondays, our first Monday back. So raise your mugs everyone. On behalf of the Men and Women Making podcast at Mom’s Basement and the men and women at Navy Federal Credit Union, serving our veterans, our active service members and their families, here’s the people who kept us safe all weekend, have kept us safe in the past. [00:02:57] OG: Cheers. [00:02:58] Joe: Thanks to you. [00:02:59] Anna: Cheers. [00:02:59] Joe: Let’s go stack some Benjamins for another eight weeks, shall we? [00:03:02] OG: Stacking them. [00:03:04] opener: Here’s the song that we’d like to do for all the younger set of people, the teenagers and what have you. This one’s called Vacation Zoe, [00:03:14] opener: vacation Z. It’s over. [00:03:18] Doug: It’s over. [00:03:26] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show. [00:03:40] Doug: I’m Joe’s moms neighbor, Doug, and let’s kick off another eight weeks of shows with the best star of the show ever you. Today we’re diving deep into the mailbag with questions from stackers, Kate, Vijay and Kevin. We’ll tackle their questions on the stock market, open enrollment 5 29 drawdowns and healthcare planning. [00:04:02] Doug: Nice job stackers. You guys have way better questions than the ones they ask over on how to money. Some lame over there. I’ll also share a TikTok minute that’s short of delight. And then I’ll also share some incredibly shareable trivia. So much sharing, you know, ’cause sharing is caring. And now here come three people who woke up on the, let’s answer your question side of the bed this morning. [00:04:29] Doug: It’s Joe OG and CFP Anna. [00:04:39] Joe: Hey there stackers. And happy Monday to you. We’re so happy to be back. We are rested and ready. And you know what, it’s time for us to answer some of your questions and here to help while here, to actually do all the heavy lifting. I [00:04:50] OG: was gonna say here, to do the work, [00:04:52] Joe: I, I’m not gonna answer the questions. [00:04:55] Joe: These five people are, let’s say hi to og. Did you have a good week off my friend? [00:05:00] OG: I did. As a matter of fact, I, uh, I spent the entire week golfing. Ugh. [00:05:05] Joe: That’s tough. [00:05:06] OG: I know. [00:05:06] Joe: I feel so bad. It’s, [00:05:07] OG: it’s a rough life. Somebody’s gotta do it. I mean, you, that handicap ain’t gonna make itself go up. You have to play to make it go up. [00:05:14] Joe: Gotta work hard to get in the weeds and in the pond and in the, absolutely. The sea trap gotta focus to be, to be that bad. When we went to Dollywood a few weeks ago mm-hmm. Dolly, pardon? G has this fantastic quote that they have on mugs and merchandise that says it takes a lot of money to look this trashy. [00:05:30] OG: It ain’t cheap being rich. That’s what we say. [00:05:33] Joe: It ain’t cheap being bad at golf. Y you, you gotta spend a lot of money to be bad at golf and somebody, I don’t know if she plays golf or not. Anna Aam is back with us. Anna, good to see you my friend. [00:05:44] Anna: Good to see you too. Happy to be here. [00:05:46] Joe: Do you play golf? [00:05:47] Anna: I haven’t played this past year, but. [00:05:49] Anna: Pre-kids. We were playing lots and lots of golf. I actually was on my high school golf team. [00:05:55] OG: Oh, [00:05:56] Anna: mm-hmm. [00:05:56] OG: Yeah. Anna would beat the living snot out of all. She’s like, I haven’t played in a year. I shot a 78. I mean, I was way off. [00:06:03] Anna: Haven’t shot in the seventies yet. [00:06:04] Joe: It’s like my, my friend who said, do you wanna play darts? [00:06:07] Joe: And uh, he’s just nailing it. I’m like, I’m like, have you played? He goes, he goes, oh, I haven’t played in like five years. And then it turns out he was on like a semi-professional dart league and still Ted [00:06:18] OG: lasso. [00:06:18] Joe: Yes. Even after all of those bad times. But isn’t it funny, Anna, back to kids, because I think people heard that loud and clear, how you can ruin [00:06:27] OG: everything [00:06:28] Anna: they do. [00:06:28] Joe: You could de divide your life like pre-kids. I used to have fun. [00:06:32] Anna: I used to play golf for 16 hours a week. [00:06:35] Joe: You never knew how good you had it, did you? [00:06:37] Anna: No. No. Enjoy it while you can. [00:06:39] Joe: Our friend Scott Galloway, who’s been on the show a couple times have said, kids will completely destroy your life. And by the way, there’s nothing better than that. [00:06:48] Joe: There is nothing better. And I agree with every, every part of that sentiment. [00:06:52] OG: I love my three little Ferraris. They’re amazing. [00:06:56] Joe: That’s so expensive and yet so adorable. Much more adorable than Joel and Matt over at How To Money, by the way. And the reason we talk about Joel and Matt so much is a ’cause they’re kind of annoying because they’re so damn nice, but also because the fact that we are in this month long death match to raise, do you like how I called it a death match? [00:07:16] Joe: Like you gotta raise the stakes OG. This year long year long month long death match with them to raise money for. Good. It’s called the Voices for Good Challenge. There’s seven different podcasts. Some of these are big name podcasters, but we don’t care about them. Joel and Matt are involved, and we just have to. [00:07:33] Joe: Make sure that the world knows that our stacker community is way more giving than the How to Money community. We’re helping a wonderful organization called gifting sense.org. Teach children financial literacy, make better financial decisions early on, right at the time when the dopamine hit is biggest in your brain and you’re feeling all the feels right and you’re making decisions about how the rest of your life is going to be. [00:07:57] Joe: Am I gonna be somebody who’s a spender or somebody who maybe can think about it? [00:08:01] OG: Spender. [00:08:01] Joe: Karen has this wonderful thing called the Does it make sense Score? [00:08:04] OG: That wasn’t a question. Sorry. My best [00:08:08] Joe: if only had been around og, but we were middle schoolers. It would’ve been, [00:08:11] OG: I still would’ve picked what I picked. [00:08:13] OG: I Am Who I am. [00:08:14] Joe: It would’ve been so much different, but they have the Does it make sense score. Go back and listen to me talk to the wonderful economist and, uh, leader of the Gifting Sense Group, Karen Holland. So Stacking Benjamins dot com slash Stacking Hope. Stacking Benjamins dot com slash Stacking. [00:08:32] Joe: Hope gets you there. Let’s help raise money. And by the way, we’re kicking outta money’s butt right now, which is awesome. I think we got it on Wednesday. Og. We gotta, we gotta say like if we reach $5,000, we’ll do X. Like maybe we’ll do a zoom q and a thing, something like that. I don’t know. We’ll chat about it and come up with something on Wednesday. [00:08:50] Joe: But for now, we’re gonna answer your question stacker. So grab a piece of paper, your iPad, whatever you used to take notes, because we’re gonna dive into a bunch of topics that are foremost in your mind today. We’re gonna hear from a couple sponsors that make sure we can keep on keeping on and you don’t pay anything for any of this goodness. [00:09:07] Joe: So we’re gonna hear from them. And then OG Anna, and maybe a little bit from me, we, we will answer your questions. [00:09:23] Joe: Our first question, let’s open it up with some healthcare. Healthcare in the news, by the way, we’ll get to that in a second. Just [00:09:30] OG: thinking about that, that time. Yeah. I’m just gonna play the bury my head in the sand game. [00:09:36] Joe: Well, Kevin doesn’t wanna do that og, so let’s hear what he’s wondering. [00:09:42] caller: Hey, Doug and Paula. [00:09:43] caller: This is Kevin from Maine, longtime listener, fourth time caller. I’m 41, self-employed, make around a hundred thousand a year and feel on track for my goals. Thanks to everything I’ve learned from the show, I have a big question about open enrollment. And Doug, I’m not talking about singles night down at the Sizzler, so settle down. [00:10:00] caller: I have 40,000 invested in my HSA from years of using the high deductible plans. And because I’m in good health with no recurring medical costs at present. I’d like to purchase catastrophic coverage with the highest deductible possible. So far, this is only available to those under 30 or with a hardship exemption. [00:10:18] caller: I don’t think I qualify for those, but HHS just released some new guidance seeming to expand who’s eligible for catastrophic coverage. I’m kind of lost in the terminology being used, and I wanna know what you guys think about this. Am I an idiot for looking at catastrophic coverage? If I qualify under the new rules? [00:10:37] caller: I could easily cover the out-of-pocket maximum from my HSA for the next few years if things went really off the rails. But what am I missing here? Thanks for all you do with the show to raise financial literacy for all of us. Appreciate it. [00:10:51] Joe: Kevin, thank you so much. And by the way, congratulations on doing a great job of saving early on and for the kind words. [00:10:58] Joe: Nice work there, brother. Let’s dive in and for all of our new stackers, there’s a lot going on here. So Anna and og, before you guys dive in, I want to, uh, just kind of define really what he’s looking at. ’cause we might have lost. Quarter of our audience even with this question. So he’s been saving money into something called an HSA. [00:11:17] Joe: It’s a health savings account for that. You’re allowed to put money in, you have to have a high deductible plan that matches with the HSA. You put money in and then you can choose a plan that, uh, has a high deductible so that you then pay out of pocket. And if you’re fairly healthy, you end up hopefully paying less for your healthcare. [00:11:38] Joe: Well, Kevin wants to go even further because he’s been so healthy that money has accumulated in his account and he’s wondering if he goes to just catastrophic coverage, something, the wheels completely come off the bus. That’s all it’s gonna cover. And he is got enough money sitting in that HSA. So he is betting here that he’s gonna either continue to be healthy or that he has enough money now. [00:12:01] Joe: The government has changed the rules. He mentioned that the government changed the rules on who’s eligible for these catastrophic plans, and that is absolutely true. The government looks at your family’s income compared to something called the federal poverty level, and that’s a number to figure out who’s gonna need help. [00:12:20] Joe: So if your income is too low, below a hundred percent of the poverty level, you are not going to qualify for catastrophic coverage help, but you’re gonna get help in many, many other areas. If your income is too high above 400% of the federal poverty level, you’re not gonna get help. But that’s because you’re not gonna get help from the government because they feel like you have enough income coming in that you can pay for this yourself. [00:12:49] Joe: So those are kind of the constraints that have been moving just a little bit. You can get hardship exemptions if you don’t qualify, or you can sign up for catastrophic coverage, which is what Kevin wants to do. Kevin wants to get the exemption to be able to qualify for catastrophic coverage. The Center for Medicare and Medicaid Services, they run the programs and here’s what they’re doing. [00:13:12] Joe: They’re making it easier for people who don’t qualify to get that hardship. Now people who make more than 250% instead of 400%, 250% of the poverty level still don’t qualify for this help. They would be able to possibly get some help. So they’re extending it to more people. Kevin’s hoping guys that he fits this. [00:13:36] Joe: Assuming that he does, he thinks he should do it. Og. Do you think that if he qualifies for catastrophic healthcare, which is much cheaper now that he has all this money saved in such HSA, is there something he’s missing? Should he do it? [00:13:51] OG: Well, ultimately it’s gonna come down to, this will be a great decision in the rear view mirror or a terrible decision. [00:13:58] OG: Unfortunately, there’s just not a way to predict what sort of healthcare needs one’s gonna need throughout a calendar year. You know, this is an open enrollment time generally for most people. I saw an article the other day that said. You know, we standardize so much stuff. Why in the heck can’t we standardize when open enrollment is for every company so that every company has the same 45 day period? [00:14:19] OG: Like that would be so much better for everybody involved. [00:14:22] Joe: Even the people in hr, right? Even the people Absolutely. Administering benefits like everybody. [00:14:26] OG: Yeah. [00:14:27] Joe: Could work off the same calendar. [00:14:28] OG: Yeah. But the government open enrollment time is, I think we’re in it right now. Mm-hmm. [00:14:33] Anna: November 1st. [00:14:34] OG: Yeah. And it goes until December 14th. [00:14:37] Anna: Yeah. 15th ish. Around there, [00:14:39] OG: somewhere in there. Don’t, don’t wait till the last day. But it’s, it’s somewhere in there. You know, when it comes to picking the health insurance plans, and I know, I think I, I think we all do this every single year, right? You sit down, you go, all right, 47 options, which one? You know, you start winnowing down the ones that you go, alright, these ones definitely are out. [00:14:57] OG: And then it’s just a gamble. It’s like, am I gonna have a big healthcare year, healthcare expense a year? And if so, what does that look like? If I go this route, if I project to have a low healthcare expense a year? What does it look like if I go these routes? And you know, what he’s talking about here is coverage that is just basically gonna cover like you need a new kidney. [00:15:17] OG: Yeah. And I’m exaggerating a little bit. It’s, it’s a little bit better than that, but he’s saying, Hey, if I break an arm, if I have a cold, you know, if I need a flu shot, wish flu shots are covered anyway. But you know, my normal physicals can be covered. But if I have some normal slip and fall type of thing, I’m gonna cover that. [00:15:35] OG: But if I have some really crazy stuff, I need some, some backend coverage and that’ll work out as long as it works out right and you know, we can’t control or we can’t even predict what’s gonna happen when we drive down the highway. Or you know, a couple weeks ago that big tragedy in Louisville of, there’s a handful of people at work and all of a sudden an airplane smashes into your building. [00:15:57] OG: Crazy stuff happens. I think it’s a fair bet, especially if you are proactive with your healthcare. To say, Hey, I’m gonna do my physical, I’m gonna exercise, I’m eating healthy. I’ve done the test to suggest that I’m on the right track. I think it’s a fair bet. Now, if you also say in my afterschool activities are, you know, I play in a men’s soccer league, I skydive and I rock climb. [00:16:21] OG: Okay, maybe you don’t wanna have just the catastrophic one. Maybe there’s some chance that, you know, there’s some other injuries that could happen or something. So this is always a tough debate and I can see arguments on both sides. I thought maybe when I saw this, this topic, um, I thought maybe he was gonna talk about the med share programs. [00:16:42] OG: We’ve talked about this before, that are starting to pop up again a little bit more frequently because of the rising costs of healthcare. And that’s more of a gamble where you’re just saying, Hey, we’re in this group association, whatever you wanna say, and we all just kinda chip in when somebody has healthcare issues. [00:17:00] OG: And that all sounds great until. Johnny needs a new kidney and it’s like $6 million and you know, that thing just doesn’t exist. So be careful with that. [00:17:09] Joe: Yeah. What I like about this is that Kevin, I think, understands the risk that he’s asking. Yeah. The fact that he’s asking this question, he understands the risk. [00:17:17] Joe: I feel like a lot of these Medi-Share. Programs. People don’t understand the risk of those programs. I mean, I’ve heard the advertisements on the radio. You’ve heard the advertisements. Yeah. They just sound absolutely wonderful. But when you go to the front page of any of these programs, what’s the first thing that it says in big letters? [00:17:31] Joe: It’s not [00:17:31] OG: health insurance. [00:17:32] Joe: Yeah. It says not health insurance. And it’s not actuarial. Actuarial. Easy for me to say. Yes. [00:17:38] OG: Try it again. Third time’s a [00:17:39] Joe: term, actuarily sound. [00:17:41] OG: Yes. Close enough. [00:17:42] Joe: Good. We got it. Almost made it there. And those words to the average person don’t mean a lot. [00:17:47] OG: Yeah. [00:17:47] Joe: But to the three of us, that means a lot. [00:17:50] Joe: Like if actuaries, the smartest people in insurance go, yeah, this could blow up on you. Like that’s a much bigger achilles heel. So I don’t like the way those are marketed. I don’t mind people doing it if they know what the risk is. But I feel like most of the people doing these mesha programs, no idea. [00:18:06] Joe: They have no idea what risk they’re taking. [00:18:08] OG: I feel like there’s an opportunity that we have when it comes to healthcare too. Just ask the next question, which is, how much is this gonna cost? And go, is there another way to do it? And I’ve told these stories a couple of times, but many times have we had an opportunity where just by asking that the doctor or you know, whatever has said, oh, well we could investigate this. [00:18:32] OG: This time last year, I tore my calf. I was at the doctor’s and he says, well, I think you should get an MR. I can get you in at such and such a place. And by the way, he proactively said this ’cause he knew I was gonna ask. He said, if your insurance covers it, you know it’s gonna fall under your deductible, which is for us, we have a high deductible plan, which means, you know, we’re out of pocket on whatever that number is and it’s whatever, you know, 5,000 bucks or something. [00:18:55] OG: Or you can pay cash and it’s 325 bucks. And I’m like, well, why wouldn’t, why would I have you guys go through all the extra steps of running it through the insurance? And I gotta pay $3,500. I pay $300 to have this done with cash. There’s a prescription medicine that I take that is 1500 bucks a month. I said to the doctor, I’m like, this is insane. [00:19:16] OG: Is there another option? He is like, well, let me call the pharmacy. And he is like, Hey, we got you a little coupon that’s applied to your account’s. $150 a month now. [00:19:24] Anna: Yeah, [00:19:26] OG: I mean I didn’t, I just said, this is insane. Is there another thing we can do? [00:19:29] Joe: The disparity’s amazing. Cheryl recently, OG had a procedure done and I went with her to the consultation and she just asked the nurse, she said, do, do, what are my options? [00:19:40] Joe: Having this done? And the nurse looked at her and goes, I wouldn’t have it done here because this facility has a facility fee of $200 to have it here. And it’s a, this is actually kind of a low cost easy thing. She’s like, I would go down to this clinic that’s a well-known clinic in town. I would get it done there. [00:19:57] Joe: And then you avoid a $200 fee that your insurance is not gonna pay the nurse working at the thing. Just ask them, ask the medical professional the question. I’d love that. [00:20:08] OG: Yeah. And a lot of times they don’t know. My favorite story is when one of my kids broke their arm. I can’t remember which kid it was. [00:20:15] OG: The first stop in the children’s hospital is the payment. They like, how are you paying for about what’s to happen? And I’m like, well, I don’t even know what’s gonna happen. How do I know what to pay? Like, well make your choice like you, which door are you going through right now? The insurance door or the cash door? [00:20:29] OG: And I’m like, I don’t even know what’s wrong. I think he broke his arm, but I [00:20:32] Joe: didn’t know it’s [00:20:32] OG: behind door number two. Like, like, how much does it cost? And the lady literally said, we won’t know until we do it. And I said, that’s fair, but let’s assume that it’s a broken arm and you have to cast it. Like, how much does that cost? [00:20:44] OG: And she’s like, we don’t know. I’m like, is this the first time you’ve ever done this? Is this, did it just open? Do you have not an idea of how much the supplies cost? Like surely you’ve casted an arm of a 9-year-old before and you have roughly a general sense of how much time, energy, and, and, and product that costs you. [00:21:01] OG: She’s like, well, you gotta pay a deposit of 500 bucks. If your insurance covers it, you know, whatever. And I said, okay, we’ll pay cash unless you know you need surgery or something. I don’t know. And then I waited for this bill to come, never came. I called and I said, did I miss a bill? And they said, no, you’re good. [00:21:16] OG: I said, well, how much? How much was it? She’s like, well, 500 bucks was good. Like they didn’t even know. They were like, they’re good. Like, you guys are fine. Yeah. Move along. Nothing to see here. Yeah. And I said, well, what would the insurance have been? And she said, if we ran it through insurance, it would’ve been 2,500. [00:21:29] Anna: Wow. [00:21:30] OG: You know? And I understand there’s more process, so it’s gonna cost more whatever. So ask about the cash price. Ask, is there anything better you can do? Ask if there’s another place that you can do your, your procedure at. To your point, Joe, because there’s a a thousand of those in your community probably that will help offset some of the costs, even if you have to have like a little bit better, more costly plan from a protection standpoint. [00:21:53] Anna: And the thing is, is like it’s for one year. The great thing about health insurance now is that for 2027, you can change. You’re, if you have some sort of ongoing issue that pops up in 2026 and now you’re on a medication that costs a lot of money, you can change your insurance for 2027. That’s the great thing about health insurance now is like, it doesn’t take into account preexisting conditions. [00:22:16] Anna: So it’s a year of risk. And you know what the top line is gonna be. [00:22:22] Joe: I’m gonna take the other side of this guys. I think this is the type of move that you consider when you’re behind. Back when I was a financial planner, if I was with somebody that was behind, I would look at shortcuts like this and go, okay, can we roll the dice on this baby? [00:22:34] Joe: And maybe we win on this thing. Mm-hmm. And if we do, and and to both of your points, I think it’s a very, it’s a good risk. He knows what the downside is. I love all that. That’s great. But I also think that if he’s ahead, I would look you in the eye, Kevin and I go, why are we bothering with this? If you’re good on your goals, let’s just take the win and let’s not take the risk that something really bad happens. [00:22:56] Joe: And now I’ve got this Achilles heel. [00:22:59] OG: That’s what you did there. [00:23:02] Joe: If I, if I don’t need to. If I don’t need to take it, why would I? So that’s, that was the first thing I thought when I heard this. Do we need to take that risk that, do we not need to take it? Yeah, but if we do, I’m totally with OG and Anna that it seems like you’ve really thought through. [00:23:16] Joe: I don’t think you’re missing anything. The big piece, I think a lot of stackers don’t know about, and I want to just mention this before we move off this topic. This is a good time to talk about health insurance as we come around to the end of the year. This comes to us from cms.gov. I’ll link to it in the show notes. [00:23:32] Joe: Expanding access to health insurance consumers to gain access to catastrophic health insurance plans in 2026. Plan year. Exactly what we’ve been talking about, Kevin, you asked about these expanding benefits, but in their wording, this is the overview. The Centers for Medicare and Medicaid Services is working to expand access to catastrophic health coverage in the federally facilitated exchange through additional hardship exemption guidance, specifically designed to help consumers access coverage. [00:24:04] Joe: Listen to the end of the sentence, as a result of the premium increases anticipated for the 2026 plan year. And the rest of this piece guys goes through the fact that this government agency thinks that in 2026 in our budgets, you need to plan on a hell of a lot more money. [00:24:23] OG: It’s a rocket ship. Yep. [00:24:24] Joe: A hell of a lot more money. [00:24:25] Joe: So man, if you’re with us today, even if you’re not working on what Kevin’s working on and you’re planning your budget for 2026 Stackers, health insurance, og. It’s gonna be a problem. [00:24:36] OG: It’s going up. [00:24:37] Joe: Yeah. Kevin, thank you for, for the call. And again, we’ll link to that in the show notes at stacky Benjamins dot com. [00:24:44] Joe: Let’s move from health insurance to 5 29 plans. Sound like fun guys? [00:24:49] Anna: Yeah, let’s do it. [00:24:51] Joe: And Anna, you’re putting money, I would imagine, in 5 29 plans for [00:24:54] Anna: Yep. [00:24:54] Joe: For some ankle biters. [00:24:55] Anna: Yep. For a little, little baby. [00:24:57] Joe: That is awesome. Let’s hear from Kate, who is on the other side of that. She’s wondering about taking money outta the 5 29 plan. [00:25:07] caller: Hey, Doug, Joe and og. This is Kate with the 5 29 Plan drawdown question. My daughter is currently a sophomore in college and she recently signed a lease for a campus apartment next year. The payment structure in the lease is obnoxious while the lease runs from August, 2026 to May, 2027. The first payment is due April 1st, 2020, and the final payment is due on January 1st, 2027. [00:25:31] caller: How do I handle this from a 5 29 drawdown perspective? Can I draw down the April to December, 2026 payments in 2026 despite the fact that part of them are prepaying 2027 expenses? If yes, since the final payment is due on January 1st, 2027, do I pay on January 1st and submit that drawdown in 2027? If not, do you have any suggestions or resources I can refer to as I try to renegotiate the payment schedule with the rental company? [00:26:03] caller: As a side note to an audience who might appreciate my gripe, I really wish that the drawdown requirements of 5 29 plans were more like an HSA or at least adhered to an academic calendar, which would align to the actual incurred expenses more directly. Thanks in advance for your response. [00:26:20] Joe: It’s so funny, Kate. [00:26:21] Joe: I mean, this is very, very similar to the problem we have with open enrollment, right? Like why do we have all this mumbo jumbo? But for people that dunno what we’re talking about before Anna and OG tackle this one, let me tell everyone that’s not sure exactly what Kate’s asking about. So from a 5 29 plan, you have very specific reasons why you can take it out. [00:26:40] Joe: Where an IRA or a 401k have certain timeframes and tax consequences to taking the money out. You can take it out for whatever you want at that point, nobody’s looking over your shoulder. Well, with a 5 29 plan. They do. You need to have it come out for qualified education expenses if you want it to be tax free. [00:27:00] Joe: Those qualified expenses are things like tuition and fees, so the cost required for enrollment at at a university, a college room and board for students enrolled, at least halftime. If you live off campus, which is what Kate’s talking about, the withdrawal cannot exceed. The school’s determine cost of attendance for room and board. [00:27:18] Joe: So it’s gotta be within what the school says that it should cost for room and board. Books and supplies are included there. And then also there’s now up to $10,000 per year for K 12 education. When you take money out, there’s no limit for those college expenses. If you’re gonna take it out to pay off student loans, you can do that, but there’s a $10,000. [00:27:40] Joe: Limit over the beneficiary’s lifetime. And then of course there’s penalties. And this is what Kate’s trying to avoid is penalties if you don’t do this at the right time. So Anna, let’s start with you. We started with OG last time. What’s Kate to do if she can’t get the, sounds like an apartment complex to change the way that she pays for this? [00:28:00] Anna: Yeah, that’s really silly. Kate. I feel you on that. And I’m, I’ve never heard of something like that. I feel like it should, unless it’s like on campus housing or something where they do something silly and it’s when you’re paying for tuition. I have no idea. I’ve never heard of this before. But in terms of reimbursing yourself through your 5 29, I think you just do it when you pay for it. [00:28:21] Anna: It’s not necessarily like when the service is rendered and when your daughter is in the housing, but it’s when you actually pay for it. So. Hopefully that answers your question of like when you’re actually taking the money out. [00:28:34] Joe: Well, so wait a minute. So in other words, she could pay for out of her funds and then during the qualified time, then she reimburses herself within that timeframe that the IRS says [00:28:47] Anna: you can pay for it from your own funds and then reimburse yourself within the calendar year. [00:28:53] Anna: Just make sure it’s done within 2026 that whatever you’ve paid for on your credit card, whatever you’re seeing there that are tuition, room and board, any other expenses that are qualified education, you’re reimbursing yourself through your 5 29 plan at that point. I think you can pay for it directly from your 5 29, if I’m not mistaken, but I don’t think every fee you can do that every college expense. [00:29:19] Anna: You can do that. [00:29:19] Joe: Oh gee, you’re nodding your head. [00:29:21] OG: Yeah, I mean when it comes to the tuition and fees and that sort of thing, I’m sure a lot of schools now are like this. I only have experience with one, but I know that at a and m where Alex goes, when the bill is due, you can just click the button that says, pay for my 5 29. [00:29:37] OG: Boom. Done. Like you go into the 5 29 company, we use my five 20 nine.org, and you just log into the account and go, I’m paying tuition to Texas a and m. Here’s the student name, here’s his ID number, send check. [00:29:50] Joe: But this is off campus housing. She’s talking about This is some, [00:29:53] OG: yeah. So you can do the same thing. [00:29:55] OG: You can say, send check to whatever, or you can, like Anna said, pay for it yourself there. This isn’t like accrual based accounting, you know? And that’s the way that I thought about this. Like, like Anna said, it better of like, it’s not when the services are rendered. It’s like when you pay the bill, you know, it’s just the bills, bills due and you pay it. [00:30:12] OG: So if you’re paying the tuition that’s due on January or the, the room and board that’s due on January 1st, yeah, I’d pay it December 15th and be done with it. This is not super complicated. I’ve, I’ve never heard, and you should check with your tax person on this, but I’ve never heard of anybody being audited regarding their 5 29 expenses because a lot of this is somewhat on the honor system. [00:30:36] OG: And what I mean by that is you’re paying for the stuff, right? You charge it, you have travel expenses. Your kid goes outta state and you’ve got a fly, or you’re gonna buy a, a MacBook and you know, you just swipe the credit card. And then to your point, all of that stuff is reimbursable from your five twenty nine. [00:30:53] OG: So you can call the five twenty nine place or log in your 5 29. Say I spent $3,100 on transportation costs and a MacBook, send me a check for 3,100 so I can pay my credit card off. And at the end of the year, you’re gonna get a distribution statement, a 10 99 queue from the 5 29 company that said you distributed $22,318 and 11 cents from your 5 29 of which. [00:31:18] OG: 5,000 of that was gains. That’s just all the info that the 5 29 company has. It’s then up to you on your tax return when you put that five, that 10 99 in to say this was used appropriately. Like literally check a box that goes, yes, I did it correctly. This was, this was used appropriately. Now there’s always a chance that the IRS comes back and says, I need the receipts. [00:31:40] OG: I need to prove it. So I wouldn’t. I wouldn’t fib on that. [00:31:43] Joe: Yeah. Well I think what you’re getting to OG is this right from the IRS it, it has important considerations, timing of withdrawals. It’s advisable to time your withdrawals to coincide with when you incur the qualified expense. For example, and I love this example ’cause Kate, this is exactly what you’re running into if you’re paying for a semester in advance, so you’re paying ahead of time, you can withdraw the funds before the payment is due because you’re making the qualified expense. [00:32:12] Joe: Yes. So it is less to do with when your child is living in the apartment than when the money is due. A [00:32:18] OG: hundred percent. This is just when you, when you pay the expense, that’s the year. And I think Anna brought up a good point. Keep this simple by having your 5 29 reimburse you, if you’re paying for it outta your own pocket and not having the 5 29 pay the pay the payment. [00:32:32] OG: Keep this in the same calendar year ’cause it’s a lot cleaner and easier to to deal with. The numbers will match and it’ll be super easy. I would check and see if the 5 29 can just send the money directly to the apartment complex, [00:32:45] Joe: no mess, no fuss, then yeah. [00:32:47] OG: And if they already have a screwy schedule, you’re paying like this weird April to January timeframe, then I would, I would just pay the last payment in December. [00:32:56] OG: I’d pay two payments in December and be done with it. And then all the books are closed basically for, uh, 2026. [00:33:03] Joe: Much like og the last 15 years been following headlines, prepping for these shows, and following what’s going on. So us stackers get all the best information. I’ve never heard of anyone that has fallen into non-compliance with the rules. [00:33:18] Joe: Yeah. But that said, I would still keep some careful records. ’cause I don’t want Kate, we don’t want you to be the first one. [00:33:23] OG: Yeah. [00:33:24] Joe: We just, just keep [00:33:26] OG: records. All these government shut down board IRS agents that are listening to financial podcasts or going, we going after late next, you know, let’s check the IP address of this. [00:33:35] OG: Well, when Kate gets [00:33:36] Anna: audited, she’s gonna play this episode for the IRS agent. [00:33:40] OG: Call us. Hey Jack wagons. [00:33:41] Joe: And that may also be why we’re saying maintain careful records. Kate. Yes. Withdrawal is to make sure that they stay compliant with IRS rules and you avoid penalties. [00:33:49] OG: I mean, the, the reality is, is that five 20 nines used to be very tight in terms of their withdrawal restrictions. [00:33:55] OG: And now it’s very, very, very loose. Arguably you can tie just about anything to a, to a qualified education expense. Is spring break probably not? If you live in Pennsylvania, your kid goes to school in California, is it reasonable to say that the transportation of an airfare back at Thanksgiving and back at Christmas is, uh, education expense? [00:34:17] OG: I think so. You know, I don’t have proof to say it’s not. Is it fair to say that every single weekend I need private jet travel back and forth and that’s a 5 29 expense? Probably not. Right? Like that seems a little excessive. [00:34:28] Joe: Yeah. I think there’s some common sense rules here. [00:34:30] OG: Yeah. [00:34:31] Joe: That you can follow. We are going to get a quick refill on our coffee and Doug, Doug has not been here the entire time. [00:34:37] Joe: What are you doing, dude? It’s, it’s time for the trivia. [00:34:40] OG: Taking a nap. [00:34:40] Joe: I know apparently he’s been sleeping on the job, everybody, but it’s time for Doug to wake up and get back at it because he has today’s trivia question. [00:34:52] Doug: Hey there, stackers. I’m jokes. Moms, neighbor, Doug, and man, man, you all have some great money. Questions. Okay, I’m gonna get in on this. I got one too. What’s the most counterfeited denomination of US currency? And how much ink, ’cause I’m curious, I’m just curious, how much ink would it take to crank those babies out? [00:35:14] Doug: Oh, cut. Okay, cut the, cut. The last part. Don’t, don’t get involved in a counterfeiting scheme. Gotcha. Okay, here we go. Take two. As I was saying, what’s the most counterfeited denomination of US currency and which brand of printer would a guy wanna, okay. Sorry. We’ll just, we’ll stick to the basics. What’s the most counterfeited denomination of US currency? [00:35:39] Doug: That’s definitely the questions. The only question I got, I’ll be back right after I go figure out the difference between a a, a misdemeanor and a felony. [00:36:01] Doug: Hey there, stackers. I’m definitely not fake money creator and guy who’s only using the cash to make the new Stacking Benjamins support game. Special Agent Murphy Promise. It’s Joe’s mom’s neighbor, Doug. Seriously, have you seen how technical money is these days? I joke about counterfeiting, but orange is not your color. [00:36:20] Doug: But for those who have counterfeited us currency, what’s their currency of choice? It’s the $20 bill. The most counterfeits are actually created outside of the USA, and definitely not in a border town in northeast Texas. Here’s a show that’s not only in the USA, but somehow makes it from Texarkana to your ears. [00:36:43] Doug: Back to Joe OG and Anna. [00:36:47] Joe: And by the way, behind the scenes stackers, Anna got that right. [00:36:50] Anna: Yay. [00:36:51] Joe: Nice job. N [00:36:52] OG: og Look for debate. [00:36:53] Joe: N og iss looking it up. That’s, [00:36:55] OG: I’m looking it up. I’m just waiting for someone to give me the source. [00:36:58] Anna: He’s just sad that he lost [00:37:00] Joe: the source Is Doug? [00:37:01] OG: Yeah. [00:37:02] Joe: What other source do we need besides Doug? [00:37:04] OG: Precisely. [00:37:07] Joe: Let’s, let’s move on. Vj. Good to hear VJ’s voice. I think VJ’s been with us for a while. Vj, what’s your question today, man? [00:37:18] caller: Hi Joe OG and neighbor, Doug. This is Vij. I just learned that it took Japan’s index over 34 years to finally surpass its 1989 peak. This got me thinking, how concerned should we be that the US stock market could face such a similar like lost decades scenario? [00:37:37] caller: What are your thoughts on the fundamental differences that might make such catastrophic outcome less likely? Here I’m thinking about things like our larger workforce, a land and resources. Is there something inherently different that acts as a structural advantage for the US economy? I understand that we should control what we can and maintain a well diverse wide portfolio, but I would appreciate your perspective on how severely we should weigh this type of long-term systemic risk when planning for the future. [00:38:04] caller: Thanks and see ya. [00:38:08] Joe: Thanks BJ, and, uh, good to hear your voice, man. Uh, hope you’re doing well. Let’s dive into this because he’s not wrong. OG Japan, this malaise for a long, long, long time. And I agree with VJ and I know, so do you and Anne, I’m sure you do too. This is why you have a diversified portfolio, right? [00:38:24] Joe: If you lived in Japan and all your money was in Japan, we covered this earlier this year, people are saying, do I get rid of my international? Hell no, you don’t get rid of your international. But how worried systemically should we be that maybe the US has a similar malaise o. [00:38:39] OG: Uh, well before we get started, I would like to point out that, uh, according to Perplexity, uh, which is a great AI search tool, um, domestically, the us uh, most counterfeited bill is the 20, but in internationally it’s the a hundred. [00:38:54] OG: So, uh, 50 50 Anna, [00:38:57] Anna: no, no. Sorry, I’m not giving this up. [00:39:01] OG: It’s, I got it sourced right here, but, okay. Alright. [00:39:05] Anna: Fair [00:39:05] Joe: enough. I think your AI’s hallucinating og. [00:39:07] OG: I, uh, [00:39:08] Joe: I believe Doug over your ai [00:39:10] Anna: And we also live here, so we are experiencing counterfeit. [00:39:15] OG: Yeah. [00:39:15] Anna: You, I’m a $20 bill here. Yes. [00:39:17] OG: It’s, it’s in your life every [00:39:18] Anna: day. [00:39:19] Anna: Yeah. That’s how I know the answer is 20. [00:39:21] OG: Oh, okay. I see. [00:39:22] Anna: Yes. [00:39:22] Joe: You say distributed Internationally it’s the hundred [00:39:26] OG: No. Internationally it’s the hundred [00:39:29] Joe: internationally created or internationally distributed. [00:39:31] OG: Created, [00:39:32] Joe: internationally Created. Well, [00:39:33] Anna: that makes sense. [00:39:34] Joe: Yeah, sure. Go big. Go big,go
[00:39:36] OG: big. You know, forget. [00:39:37] Anna: Yeah. [00:39:38] OG: That’s why I don’t understand the US idea. Like, you know what, let’s counterfeit the 20. Nobody will catch us. It’s like you’re going to jail one way or the other. You might as well go to jail for all the money. [00:39:47] Joe: Right. It’s not like you’re going from orange to bright orange. I mean, come on. Yeah, [00:39:49] OG: exactly. [00:39:50] OG: I got stripes on that. [00:39:51] Joe: Yeah. So let’s talk about the risk of that Oog. [00:39:54] OG: You know, I think that if you go back in time, there was, uh, some other issues going on in Japan. I just read this piece in the last couple weeks that the value of land in Japan was more valuable than all the companies, or maybe it was the other way around. [00:40:13] trailer: Wow. [00:40:13] OG: During the height of the, like it was, everything was just mucked up. Like it was just very unrealistic. And the reality is, is I think that different economies and different sectors of economies are going to experience. Similar things over long periods of time. There’s gonna be an area, I mean US housing market in 2000, right? [00:40:36] OG: Huge collapse. And he said, what if the US has a lost decade? We had that in 2000, 2010. I don’t remember the exact numbers. I think the s and p averaged 2% over that 10 year period. [00:40:45] caller: Yeah. [00:40:45] OG: And then on the heels of it. But if I’m comparing the Japanese stock market to the US market, just number one, I’m gonna say we’re just way, way, way, way, way bigger. [00:40:56] OG: And therefore have different areas to assuage some of that volatility concern or that that long-term decline. But that doesn’t mean that there’s not a two year, three year bear market somewhere in the future that has equally terrifying, you know, results. You can just look back and as recently as a great recession and, um. [00:41:21] OG: That was pretty crappy. There was a lot of, a lot of wealth lost during that time. But the important thing I think to remember is just like the Japanese market, although it took a long time to get back to even people that were invested and people that were diversified and if you were rebalancing when you were supposed to, were rewarded. [00:41:42] OG: Now that doesn’t mean that the person who had a million dollars in 1988 in the, and all of a sudden in 2000 were worth 300,000, that they were rewarded by waiting the next 25 years to like get back to even money. It still requires investing and that sort of thing, but that’s the same premise as any area of the economy or any area of the global economy, right, is you’re investing. [00:42:07] OG: You rebalance, see what the results are, sell from the things that have done well, rebalance back into the things that haven’t done well and washer and repeat, and that’s statistically has given you the best odds. It’s not to say that it’s never gonna happen, it’s what’s the best odds to be successful over the long term. [00:42:24] Joe: Anna, [00:42:25] Anna: I think of this from the perspective of if you were to plan for this, like if we think that this is a likely outcome, not just like a recession, but something like what happened in Japan and we were to actually plan for it. Like what is the plan? You put all of your money in cash or you put it all into fixed income so it’s more secure and that’s not really an option either. [00:42:49] Anna: Like that’s gonna get you nowhere. So I don’t know the statistics around why the US economy is more stable or wouldn’t be hit as hard or could bounce back better than the Japanese economy. But I do know there isn’t really a solution to avoiding this if it were to happen in the future. Like you have to be invested or you’re gonna get nowhere within your financial plan. [00:43:13] Anna: You’ll be working forever. [00:43:14] Joe: Let’s talk about the ways, ’cause I love how you make this actionable and put it right in into behavioral terms. We can’t control what happens to us, but we can control what we do about it. The first thing, og, what you said around diversifying and rebalancing, look at what, what happened in a rebalancing situation, which would be, you would consistently find yourself making money on the other pieces of your portfolio. [00:43:42] Joe: You would still make money because of the fact that you stayed balanced. Now the thing that’s frustrating to me is everybody always wants to get out of balance because they love what just happened and they want more of the thing that just happened. I want more tech. I want more Nvidia. Yeah, I want more crypto. [00:43:58] Joe: Let’s do the thing that is quote, doing real good versus staying even. It’s in staying even that we avoid this. The second thing is, Vijay, if you’re putting money in to a diversified portfolio, even during that time, the Japanese economy didn’t stay at zero. It bounced around. There was hope, and then there was despair, then there was hope and there was despair. [00:44:20] Joe: And even during the lost decade in the United States that investors still made money by investing all the way through that because of dollar cost averaging. During those times when it actually dipped lower, even though the market did nothing over the long term, you still assuming that during those dips you continued to buy in even amounts, you still came out ahead of zero because of the fact that A, you put money in. [00:44:46] Joe: I think a lot of people stop putting money in if they think it’s going to go to zero, which is ridiculous because you still have to save, right? Yeah. And if it bounces around, you’re gonna make money. Uh, just on the volatility makes you some money. The third thought that I had was just about, you know, the Japanese equivalent of the Federal Reserve is called the Bank of Japan. [00:45:06] Joe: Lots of finance programs and universities across the world have talked about the big mistake Japan made. Like this is not, you know, Joe giving you a secret, nobody else knows. Japan very quickly took their interest rates to zero thinking that this was going to be short term. And much like the Federal Reserve, when you start lowering rates, if you do it too quickly. [00:45:32] Joe: You got nothing you can do. Like when rates go to zero now their federal reserve has no, no recourse anymore. So when you see this, uh, this playing out right now in American politics, the President saying, lower rates, lower rates, lower rates, and the chairman of the Federal Reserve there for what the first half of this year’s going, no, no, not gonna do it. [00:45:52] Joe: Not gonna do it. And now he’s doing it because he sees, you know, some data that friction is good. The friction between the White House and the Federal Reserve. That’s a good thing. And so the Fed Chairman going, I gotta keep this slow, is specifically to avoid what happened in Japan because Japan just had no recourse and now they’re on a rollercoaster that’s outta control with nothing they can do about it. [00:46:15] Joe: I don’t know. That’s, [00:46:16] OG: yeah. No, no ammo left. [00:46:18] Joe: Yeah. [00:46:19] OG: The biggest thing there is the rebalancing and the consistency. Was it Peter Lynch that said this, more people have lost more money preparing for the next bear market than in all the bear markets. You know, it’s like, like waiting for the next thing to happen. [00:46:33] OG: People ask, sometimes they’ll say, oh, well the market’s at an all time high. It’s like, the market’s always at an all time high. How long do you guys have to see this happen? To realize it’s always at an all time high and then all of a sudden we get like a two or three or four or 5% negative month and people are like, I knew it. [00:46:49] OG: It’s the crash. It’s coming. It’s like, okay, so what? Like this stuff happens and the cost of being an equity investor. Well, first of all, if you don’t invest in equities, if you don’t own companies, your only other option is to save all the money that you could possibly need for all of your retirement in cash, which newsflash, you could save all of your money that you’ve ever made for your entire life. [00:47:13] OG: And from 22 to 65, your entire salary never consume a dollar, and you would still not have enough money to live from 9 65 to 95 because of inflation. There’s no way to do it. So that option is purely off the table unless you don’t believe in math. [00:47:29] Joe: And by the way, even then, og, it’s still off the table. [00:47:32] OG: It’s, I mean, there are some people out there who will say, well, you know, grandpa died at 72, so I’m just gonna die at 75. It’s like, okay, well you’re right. I can’t predict how long you’re gonna live, and if you only have a 10 year time horizon that you can pretty much do whatever you want. But I’m planning on having a 50 year time horizon, and I got kids and grandkids that I wanna make sure are set for generations. [00:47:51] OG: So that’s my plan. So the only other thing is investing in companies, and then you look at the history of investing in companies all the way back to the most data we have is the early 18 hundreds from Jeremy Siegel. But even if you don’t believe the 1800 stuff, you can say, all right, how about 19 hundreds? [00:48:07] OG: Look at all of the craziness that has happened in just your lifetime. Make a chart year by year of the chaos that’s happened, not of the good stuff, of the chaos that’s happened since you were born. And then go back to the day you were born and write down what the s and p was at, or write down what the DAO was at. [00:48:27] OG: And now look at it today and tell me that if you knew or if your parents knew that all of this nastiness was gonna happen in the next 47 years of your life, or the next 52 years of your life or whatever, how much money would you invest in that economy? And you would go, no way, man. Like bank collapses wars, rumors of wars, terrorist attacks, more bank collapses. [00:48:55] OG: Just look at the last quarter century of the stuff that’s happened since the year 2000. Take out. The eighties and nineties, no way would you have invested any money. And yet people still buy cars. They still buy razorblades, they still have to put food on the table. We are constantly evolving as a society in terms of advancement, and we’re always trying to do more with less stuff. [00:49:19] OG: That’s just what the economy has done from all time. And so why would you wanna bet against that, knowing that there’s. Two hundred, a hundred fifty, twenty five, pick your timeframe, years of experience here. That doesn’t mean that there’s not gonna be times that go down. There are, there’s gonna be every four or five years, we’re gonna have a minus 20 in there and you’re gonna have a million bucks and you’re gonna wake up at the end of the year and have 800 K. [00:49:45] OG: You’re gonna go, God, that sucked. And the key at that time is to do the same thing that you did that got you to a million. Because if you do the same thing, that 800 will turn to 1.6. If somewhere in that million going to 800, you go, yeah. You know, somehow I feel like this is the time that we’ll never recover the economy’s, you know, the political system, like whatever is in a place that’s never been, and therefore I can’t believe it will ever go up again. [00:50:15] OG: That’s when you die, you’ll run outta money at that point. That’s the big mistake. Don’t do the big mistake. Keep doing the same thing that got you to the million and watch how fast it grows. [00:50:26] Joe: I’m so inspired now, aren’t you, Anna? [00:50:29] Anna: Yeah, that makes me [00:50:30] Joe: Thank you, coach. [00:50:31] Anna: Ready to go? [00:50:31] OG: Yeah. What happened? I just blacked out. [00:50:33] Joe: Thank you. So, but oh, you nailed it. Even the East German judge gave you a 10. Beautiful. And East Germany hasn’t been a thing. There’s people going Germany. Wait, well what? Wait, what? [00:50:42] OG: It’s a good joke everybody. [00:50:44] Joe: Thank you so much vj, Kevin, and Kate for making this a great episode. If you’ve got questions for the show, send them to us and OG Anna and I are planning our next episode, uh, where we answer your question. [00:50:57] Joe: Stacky Benjamins dot com slash voicemail. Everybody who asks a question gets some cool Stacky Benjamin swag for being brave and for helping us make the show. So thanks to Kevin, Kate and Vijay, and you’ll be getting an email from Gertrude as we speak. But at the end of the episode, we step out in the back porch where we talk about things going on in the community. [00:51:16] Joe: I wanna shine a light on something, guys. Two things. Number one, stacker. David. David, by the way, I can, I usually don’t say stacker’s last name, but David has been on the show with us talking about picking wines Mm. Around holiday times. So anybody who knows wine like David does is a friend of mine. But, uh, David said he just listened to episode 1756, which is. [00:51:40] Joe: When money gets tight, talking about the government shutdown and about people being laid off from Amazon and other places, uh, he said, you know, the holidays are close. Listening to this episode at least once or twice. Oh gee, seemed like he had a heart. I didn’t record the timestamps, but I’m planning to re-listen as he softening up, as he gets older, I blame Wicked. [00:52:02] Joe: David says, is David making you soft? Og what’s going on? [00:52:07] OG: I, I don’t, I I’m gonna have to re-listen to the episode. I, i, was it, was it the one we used AI [00:52:13] trailer: for me? [00:52:15] OG: Is that the one? [00:52:16] Joe: Yeah. Did David, David, that wasn’t really og He took the day off. So we had AI and we, we forgot to prompt it correctly. It wasn’t snarky enough. [00:52:26] Joe: David. Thanks for that. By the way, stacker, Kevin also had maybe my favorite one. He said, Anna, that he can’t remember how to write one 1051 six or 500 Roman NUMs. [00:52:40] Anna: I don’t either, so that’s okay. [00:52:41] Joe: He said I am livid. I-M-L-I-V-I-D. [00:52:49] Anna: Oh, he got me [00:52:52] Joe: Kevin. Nice job. And that’s in our basement. Facebook groups stack you Benjamins dot com slash basement gets you there quickly. [00:53:00] Joe: And then we’ll ask you a few security questions so we don’t get bombed by spammers, which, oh my God, there’s so many spammer that wanna get into your group so we make sure they don’t get through. So give us a few minutes and then we’ll get you in and then you can crack jokes that, uh, and I’m sure we’ll share with nobody later, like that one. [00:53:17] Doug: Mm-hmm. [00:53:17] Joe: Also, one more thing. We’re raising money for charity. I said this at the front end. We didn’t rip on Joel and Matt as much as we should have. I mean, Joel and Matt, just, there’s so much to rip. I mean, Anna, nice job. Much better advice you gave today than people would get at how to money. [00:53:34] Anna: Absolutely. [00:53:35] Anna: Go there if you only want. Trash. [00:53:38] Joe: Yeah, that’s right. [00:53:42] Joe: Is that [00:53:43] Anna: too [00:53:43] Joe: harsh? We can’t, we can’t even trash talk without cracking up. That’s how these guys are so damn nice and we’re trying so hard, so hard. But stackers, you gotta give more than the how to money crowd. I mean, I know you, you know, you, you know that you can give, you know, you believe in financial literacy. [00:54:01] Joe: That’s why you listen to this show, right? Instead of How to Money, because you really want true financial literacy instead of whatever, you know, time to time, they maybe have a good one, right? Every once in a while. But here we make sure that we’re bringing it for you. So Stacking Benjamins dot com slash Stacking hope, that’s the name that our community said they wanted to give to this giving month. [00:54:22] Joe: So please help us beat Joel and Matt. The cool thing is, by the way, there is something in it for you besides the warmth of helping. Young people learn more about money because we’ve partnered with a bunch of iHeart shows, the iHeart Music Festival, which has tons of big bands. Every time that you give your name goes in a drawing for the iHeart Music Festival. [00:54:42] Joe: Two free tickets, transportation, your hotel, everything on top of that. There’s a bunch of other prizes. But if you go to Stacking Benjamins dot com slash Stacking, hope, you’ll see all about gifting sense.org. Karen Hollen’s, fantastic organization. We’re helping and about all the other loser voices like how to money that we’re competing against that we’re totally gonna decimate. [00:55:03] Joe: So, alright, that’s gonna do it for today, except this. Anna, where can people find out more about you? Where can people, if they want to chat with you, how do they learn more? [00:55:13] Anna: If you wanna connect with me, you can find me at. Stacking Benjamins dot com slash OG and just request me. [00:55:20] Joe: Yes, it’s super easy. That’s Anna and OGs calendar. [00:55:24] Joe: And you know what? It’s time stackers. We’re looking at, uh, we’re looking at the end of the year already. I feel like we were just talking about this last year, like we’re looking at 2025. So if you’re 2025, when as fast as mine did, and uh, it’s over before it even feels like it began and you’ve done nothing, well, time to make 2026 a better year. [00:55:43] Joe: Stacking Benjamins dot com slash og. All right, that’s gonna do it for today. Big thanks. Thanks for joining us again, Anna. [00:55:50] Anna: Thank you, [00:55:51] Joe: Anna. It’s going to be my co-host next week, but coming up on Wednesday. Gee, get this. Jason Zweig. Is it Zweig or swe? [00:56:00] OG: Yes. [00:56:01] Joe: Yes. Uh, Jason. Every time I pronounce his name, by the way, I get a, I get a note from a stacker going, you pronounce Jason’s name wrong and I love Jason. [00:56:09] Joe: How, how often do we talk about Jason For the people who don’t even know who Jason is? Jason is the long time, uh, columnist at the Wall Street Journal. Brilliant writer. Jason points to this, uh, study OG that just came out, which was pretty interesting. It says, shock of Shocks. You should probably be all stocks all the time. [00:56:28] Joe: Jason says, pump the brakes on that. Oh, here’s what could go wrong. [00:56:34] OG: No, nothing goes [00:56:35] Joe: wrong. OG versus Jason Zweig. Jason’s week, Jason og and Jason. And also, by the way, executive coach, uh, Katie O’Malley’s gonna be here talking about if you get distracted a lot lately, we’re in the distraction economy. She’s a fantastic executive coach. [00:56:49] Joe: Her TEDx talk has been watched by hundreds of thousands of people on this topic. How do we make sure that we’re focused and that we’re on point and that we’re intently listening to the people around us? So whether you use that at work or in your personal life, that’ll help you stack what’s happening. I [00:57:06] OG: wasn’t paying attention. [00:57:06] Joe: Start over. Yeah. What? Wait, huh? Yeah. Alright. And on that note and the eye roll from Anna, we’ll see you guys next time. Doug, what should be on our to-do list at the end of today’s show? [00:57:16] Doug: So what should we have learned today? First, take some advice from VJ’s question While markets rise and fall. The best way to wealth staying diversified and working on your income streams, investing your hard-earned savings in just one ecosystem is a dangerous endeavor. [00:57:34] Doug: Second, planning your 2026 budget plan on significant increases to your health insurance expenses next year. Figure out how that might fit in your budget ahead of time to avoid debt or worse. But the big lesson, Joe, talk about counterfeiting your mom’s no angel either, man, I saw her laundering laundry. [00:57:57] Doug: You think it’s just Tide pods going in that machine. But I know money laundering when I see it. I check every sock for cash. Nothing. Zip. Nada. Damn. She’s good. [00:58:11] Doug: Join us Wednesday. It’s Mentor Day in the basement, and that means we are joined by Elite Executive Coach Katie O’Malley. Find yourself distracted or want better communication. Katie’s gonna share techniques to keep you focused on task and intently listening while in important convers. That’s Wednesday back here in Mom’s Basement. [00:58:34] Doug: This show is the property of SP podcast LLC, copyright 2025, and is created by Joe Saul-Sehy. Joe gets help from a few of our neighborhood friends. You’ll find out about our awesome team at Stacking Benjamins dot com, along with the show notes and how you can find us on YouTube and all the usual social media spots. [00:58:55] Doug: Come say hello. Oh yeah, and before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s Mom’s Neighbor, Duggan. We’ll see you next time back here at the Stacking Benjamin Show. [01:00:07] OG: Had the opportunity to, uh, be on a plane the last couple weeks, several plane rides. So I got caught up on a whole bunch of stuff on Netflix and uh, I watched two, I watched a movie and I watched a show. And I know we talked about diplomat, but I don’t wanna talk about that. Uh, I think Doug, you and I both thumbs up real quick on diplomat. [01:00:24] Doug: Thumbs up. Yep. [01:00:25] OG: Across thumbs for sure. So if you haven’t got to Diplomat three seasons, you can do it. All right. The first movie that I saw, uh, number one in movies on Netflix right now. Called the House of Dynamite. [01:00:39] trailer: Approximately three minutes ago, we detected an ICBM over the Pacific. Current flight trajectory is consistent with impact somewhere in the continental United States have we seen Death Con, [01:00:54] OG: is this real? [01:00:59] Doug: Stratcom is asking for launch instructions right now. [01:01:03] trailer: I’m gonna need you. To breathe. [01:01:06] OG: We are talking about hitting a bullet with a bullet. [01:01:09] trailer: So is it going to ask? That’s what 50 billion. Advise us, get in the car and just start driving. If we do not take steps to neutralize our enemies, now we will lose our window to do so. [01:01:27] trailer: If we get this wrong, none of us are gonna be alive tomorrow. [01:01:33] Doug: There is no plan being, [01:01:34] trailer: we did everything right. Right. [01:01:38] Joe: Whenever they say nobody’s gonna start a nuclear war, so this is about somebody starting a nuclear [01:01:43] Doug: world. You know exactly that. Somebody’s about to do that. [01:01:45] OG: So it starts out with everybody just going to work like normal situation room in DC and they’re just doing the handoff like, Hey, what’s going on today? [01:01:53] OG: Da, da da da da. All of a sudden somebody goes this, they got the screen up and it goes, Nope. They go, wait, what’s that? And somehow we. The US missed the launch of this, uh, missile. And so this missile’s up and going and they’re like, huh, a test fight. Like, what’s, is this a satellite launch? We’re just waiting on Elon Musk to say, oh, sorry, forgot to, forgot to mention that we’re putting this, you know, whatever. [01:02:22] OG: And then they realize that it is not, and it’s 20 minutes of them trying to figure out what is going on as this thing is like entering the orbit of the earth and then coming back down. I caught wind of this when I was in Chicago because they said that the impact is Chicago. So that’s where the, the missile is headed. [01:02:42] OG: And so there’s a new story about like, if you’re sensitive to this sort of stuff and you live in Chicago, you probably don’t wanna watch this movie as, don’t watch it. Chicago potentially, uh. I am going to give this a gigantic thumbs down, like double, triple thumbs down. [01:02:59] Doug: And yet it’s number one, [01:03:00] OG: it’s number one. [01:03:01] OG: I, I don’t want to give away any reasons why, but the structure of the movie is garbage. So I’m happy to tell you guys if it, should I say what it is? Maybe just do like a three second thing, like come back in seconds. Let’s do [01:03:18] Joe: that. If you wanna watch it to see why it’s a thumbs down, we’ll give you three seconds to stop listening. [01:03:24] Joe: ’cause I’m not gonna watch it. [01:03:25] OG: Okay. If, if you’re still listening, you’ve been warned, I’m not gonna give away what happens in the movie, but as this movie progresses, there’s this countdown, right? The missile’s going and you’re watching the countdown. And there there’s, you know, everybody’s calling this frantic, it’s a hugely suspenseful thing. [01:03:42] OG: And then it gets down to like five seconds, four seconds, three, two, and then fade to black. Now the movie starts over from a different person’s perspective. So now, instead of being in the situation room, you know, you’re in the Air Force base and these guys are just chucking it up, having a good time, and then they get the alert. [01:04:05] OG: And so now it’s them going, oh, sh Nike’s, we’ve got 20 minutes to get the, you know, and you see the bombs being loaded on the plane and they launch and they’re freaking out. And then it fades to black and now it goes to the president and he’s in a motorcade, going to do this thing. It’s like all these different perspectives and there’s no ending to the movie. [01:04:26] Doug: Oh, [01:04:26] OG: the movie just stops telling you stories. [01:04:29] Doug: You have no idea what if it was real or not. [01:04:31] OG: No idea. No idea who did it. No idea what we did about it. No, you don’t [01:04:37] Joe: think some people are gonna think that’s clever and they’re gonna like that. [01:04:40] Doug: That’s horse pucky. [01:04:41] OG: It is absolute garbage. So I was like, I was like on a plane. [01:04:45] OG: I wanted to throw my, I wanted to open the emergency exit and throw my phone out the window from 30,000 feet. So that would be a rational [01:04:51] Doug: response. Yeah. [01:04:53] OG: I was like, like, this is so dumb. What a waste of an hour and 45 minutes. [01:04:57] Doug: When you started this and you were saying, we don’t know if it’s real or not, it reminded me of the real life situation like this that happened in Russia. [01:05:06] Doug: Have you guys heard this story? [01:05:08] OG: No. [01:05:08] Doug: I’m not setting up a joke. So 1983 there was a, there was a lieutenant, the [01:05:13] OG: movie, the war game. [01:05:16] Doug: Nope. [01:05:16] Joe: No, he’s talking about something that really happened. [01:05:18] Doug: Yeah, this is a real thing. So, and, and this is one of those cases where we don’t realize how close we were to the, the world ending until long after it happened, but there was a Russian lieutenant, so way down the chain, you know, like not top dog at all. [01:05:32] Doug: He was working in their air defense center and this was a, a few weeks after the Russian shot down a Korean commercial airliner that made, you know, huge news. Everybody knew about that. You didn’t OG because this was like years before you were born. Probably in 1983. [01:05:48] OG: Nope, I was in kindergarten. [01:05:50] Doug: So they had, in this defense Missile Defense center, they were getting alarms that a missile had been launched from the United States. [01:05:59] Doug: Shortly after that, three more showed up and he didn’t believe it and he disobeyed protocol and his superiors and did not. Fire counter attack and save the world by going against Russian military command and protocol. Guy’s name was Stanislau. Petrov. [01:06:19] OG: Yeah. That’s what’s going on in this movie is everybody’s on the phone with everybody going, Russia’s like, that wasn’t us, man. [01:06:25] OG: And it’s like, well, that’s what people who would do, it’s would say. And it’s like, no, it’s not. It’s like, well, we know your subs in the Atlantic, surface your submarine right now, and to prove to us that, you know, you’re not on an offensive. And it’s like, but if I do that, you blow us out of the water. I promise not to blow you outta the water. [01:06:40] OG: How do I know? You know, it’s like you talked to the Chinese, the Chinese said they didn’t do it, but I think this might be, this is, you know, how did we, you know, it’s just all this chaos and for the first 20 minutes of the movie, you’re like, holy crap, what are we gonna do? And then when it starts over, you’re like, wait, what is happening? [01:06:56] OG: And then you go, oh, we’re starting over from. A [01:06:59] Joe: different perspective, [01:07:01] OG: stupid [01:07:01] Doug: and all of which I’ve seen some movies like that and you think, okay, this could be cool, but if they don’t give you any resolution, there’s [01:07:06] OG: no [01:07:07] Doug: end. Now I’m pissed. [01:07:08] OG: Yeah. Now I will say that I did watch another show, if we got time for one more called Zero Day, and I watched the first episode of this. [01:07:15] OG: Took it off the table. ’cause I was like, I’m not sure. And then went back to it and it got better. This is like fine wine. It gets better every episode. Here’s the series. It’s a six episode series called Zero Day [01:07:29] trailer: 2,402 People died on zero day plane crashes, train derailments. Total chaos. [01:07:42] trailer: Whoever’s responsible for this attack, they’re dangerous and they say they’re gonna do it again. Congress is authorizing a special investigatory commission and endowing it with powers of surveillance search and seizure. I’m just gonna grab people off the streets without warrant. Actually you are. [01:08:11] trailer: People believe what they need to believe. The truth is the truth, but it’s not always the most important thing. [01:08:23] Joe: Wow. Sounds like you’re like an uplifting stuff, man. [01:08:25] OG: Yeah. [01:08:26] Joe: Apocalypse much. [01:08:27] Doug: And is that De Niro? [01:08:29] OG: Yeah. Zero Day is the name of this show. Um, Robert De Niro. Jesse Clemens. Lizzie Kaplan.Wow.
[01:08:36] OG: Connie Britton, Joan Allen, Angela Bassett. Matthew Modine. Pretty big cat jam packed with people. So this is a, uh, I mean, it’s a terrorist attack that happens. [01:08:48] OG: It basically takes out the grid. It’s the grid, it’s all the, like, everything shuts down for a minute and then comes back and, uh, the former president is, um, tasked with being the. Special prosecutor on this commission to figure out who did it. And he starts pulling the thread of who did it. Now the thing that’s interesting is at the beginning of the movie when he’s sitting there, uh, he is pretty much going crazy. [01:09:15] Joe: Oh, [01:09:15] OG: he’s seeing things, he’s hearing things. Um, you get to, uh, kinda unravel his past of why he’s not president anymore. He stepped down in the middle of a term or didn’t seek reelection and some family events that happened and that comes up. So there’s all that. While he’s trying to unravel this and also battle these demons of like, am I, you know, is this like early onset dementia? [01:09:39] OG: Like that’s going on? Is there something else afoot? Is this just, you know, psychosis of some kind? So he starts kind of pulling the thread. Now the difference between this show and the other movie is that this does have a finality to it. As he unravels what happens. Has a very tough decision to make at the end of like the who done it part and uh, is very good. [01:10:03] OG: So [01:10:03] Joe: this sounds like a big thumb up. [01:10:04] OG: This I would give a big thumb up too. Very dark, lot of, you know, not great themes going on. Espionage and surveillance and you know, very much the dark side of all of this stuff. Like if you think about, um, what was it? The Patriot Act, right? The Patriot Act after nine 11. [01:10:22] OG: Like, everybody’s like, yeah, that’s great. And now we see the other side of that, which is, you know, it’s 20 years later. Do we still need 700 layers of security at airports? Probably. Does it need, you know, should we up our tech. At this point, we probably don’t need to have our shoes off. Like they have a pretty good sense of what’s going on. [01:10:37] OG: I had had the full body search the other day at the airport. [01:10:40] Joe: Sounds fun. Oh, you loved every minute of that, didn’t you? [01:10:42] OG: I was trying to make jokes. The guy was not having it. [01:10:45] Joe: None. [01:10:45] OG: But what I did do was, as his hands were down my pants and people were looking at me like, what is this guy doing? I would make like extended eye contact with them and I would just smile. [01:10:55] OG: Don’t break it as they walked through the airport, don’t [01:10:56] Doug: break it. [01:10:57] OG: As they’re like looking at me going, what is going on with him? I, I just look at him and smile until they broke eye contact. So yeah, it was, uh, it was good for everybody. I had a good time. And [01:11:08] Doug: what was the name of the hot piece of garbage? [01:11:10] Doug: We should avoid the first one again. [01:11:12] OG: The house of dynamite, triple thumbs down. I’m using your thumbs to also thumb it down even though you haven’t seen it. And then zero day thumbs up.




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