Year-End Money Moves: Student Loan Savings, Roth Conversions, and Disability Insurance SB1912

Some of the best money moves of the year come with a deadline most people never notice. A student loan rate can drop by a full percentage point with one setup step. A window may be open to move retirement money with little or no tax. A gap in your income protection can sit unnoticed until a claim gets denied. Joe Saul-Sehy and guest co-host Anna Allem, CFP, sort the urgent from the merely interesting, using a caller’s real insurance dilemma, a family college decision, and a ringside look at the market’s worst Mondays. It takes a free hour before the calendar flips and no finance degree. What You’ll Walk Away With The deadline that got pushed back, and the one setup step that trims a student loan rate by a full pointWhy one point off a rate is a bigger win than it soundsWhat to check first if your repayment plan changed without you doing anythingA simple way to show a student what a college choice will cost after graduation, using real salary dataThe question one family asked a kid before agreeing to the pricier schoolWhy a year-end Roth conversion deserves a look from some savers, and the Medicare premium surprise to understand before you try itWhat an insurer does when a condition is already on your record, and why shopping around won’t change itHow to map the “crater” a lost income would leave, and when that math says you can skip the policyThe employer route that can quietly solve a coverage problemWhich of three famous Black Mondays hit hardest, and when a mutual fund trade really happensA starting point for someone new to saving, military families included, that begins smallWhy This Matters Now Year-end is when quiet deadlines pile up and good intentions slip. You don’t need to master everything on the list. You need to know which items are time-sensitive, which can wait, and which you can cross off. If you worry about making a move you can’t undo, or feel behind because you haven’t looked at your plan lately, this is a low-pressure way to catch up. From the Basement Doug turns the trivia into a title bout, with boxing legends and a bowl of queso that did not survive the match. He also makes a Trans Am joke that nobody else in mom’s basement gets. Resources Mentioned Education Department Extends 1% Student Loan Auto-Pay Cut https://thecollegeinvestor.com/89534/education-department-extends-1-student-loan-auto-pay-discount-deadline-to-december-31/: The College Investor on the extended deadlineStacking Benjamins Guides https://stackingbenjamins.com/guides: HR and benefits, college planning, and taxesOccupational Outlook Handbook https://www.bls.gov/ooh/: Bureau of Labor Statistics salary and job data for comparing majorsThe MILMO Show https://laceylangford.com/expert-resources/milmo-show/: Lacey Langford’s podcast on money for military familiesGet a Financial Life by Beth Kobliner and The Simple Path to Wealth by JL Collins: the two books recommended for new saversAsk a question for the show https://stackingbenjamins.com/yelldownstairs See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

• 0:00Speaker 00

  Your sausage McMuffin with egg didn't change. Your receipt did. The sausage McMuffin with egg extra value meal includes a hash brown and a small coffee for just $5, only at McDonald's for a limited time. Price and participation may vary. Promotion pricing may be lower than meal pricing.

• 0:15Speaker 01

  Network freedom and flexibility. That's what you want in a healthcare plan. With a Humana Medicare Advantage PPO plan, you can see any doctor in the country who accepts Medicare, including specialists. No referrals, no kidding. Learn more at gethumana.com. See any doctor who accepts Medicare and is willing to build Humana. Humana PPOs may not be available in all areas. Benefits and costs share may vary. Humana is a Medicare Advantage PPO organization with a Medicare contract. Enrollment in any Humana plan depends on contract renewal.

• 0:45Speaker 02

  Here's a song that we'd like to do for all the younger set of people, the teenagers and what have you. This one's called Vacations Over.

• 0:55Speaker 02

  Vacations over. It's over. It's over.

• 1:06Speaker 03

  Live from Joe's mom's basement, it's the Stacking Benjamin Show.

• 1:21Speaker 03

  I'm Joe's mom's neighbor Doug, and today we're knocking down some of the biggest headlines in personal finance, like how about 1% off your interest rate on those student loans? Or if you're in retirement, how about a cool 47.5 of tax-free rollovers to a Roth IRA? And that's not all. We'll answer your money questions, including the biggest question of all. What's the answer to Doug's hot and fresh money trivia question? That'll be halfway through today's show. And now, two people fresh off the weekend, here's Joe. Hold on, why the did you type your full name, Joe? I never say your whole name.

• 2:02Speaker 04

  Just to put the Andrew in there, the third.

• 2:05Speaker 03

  Right. Who went to the Citadel?

• 2:07Speaker 04

  Esquire.

• 2:08Speaker 03

  Yeah. Here's Joe and Anna L L L L L.

• 2:16Speaker 04

  Hey there, stackers, and happy Monday to you. We're super happy we're here and OG has declared this a long weekend, a personal day, which is good for us, Doug, because we've got special co-host Anna Ellen with us.

• 2:30Speaker 03

  How are you? So good for us.

• 2:31Speaker 05

  I'm good, Joe. How are you?

• 2:33Speaker 04

  Well, I'm great now that you're here because we're going to have not just a fun day today, but you're here all week. You're here on Wednesday as well.

• 2:41Speaker 05

  All week long. Yeah, Josh is taking some time off, so I'm coming in.

• 2:46Speaker 04

  It's going to be a great week, so buckle up, stackers. And you know what? Today we got a great discussion, Anna, because whether you are somebody just starting out, well, maybe not even just starting out, if you've got student loans. A lot of our stackers stopped paying off their student loans about the same time the social security check came. So we might be a little later in life when it comes to student loans, but some news on the student loan front, number one. But number two, if you are social security age, specifically if you're over 65, there might be a big opportunity for people before the end of the year on that front. And my goodness, we got even more than that. So you ready to cover some big time ground today, Anna?

• 3:28Speaker 05

  Let's hit it.

• 3:29Speaker 04

  All right. We are going to hit the ground running quickly, but we've got a couple of sponsors who help us keep on keeping on. We're going to hear from them first and then Anna, Doug and I, we're going to tackle some of the biggest headlines in personal finance for 2026. Remember Superman? It's a bird, it's a plane, it's Superman. Well, guess what? We've built the equivalent for your money. It's a budgeting app, cancel subscriptions, protects and helps you build credit, tracks your net worth and so much more. It's the super app called Field Kit. You don't want to spend time managing your money. You want to be out in the field, so get the Field Kit. So everything's in one place and you stop staring at screens all day. Check it out at stackyourbenjamins.com/fieldkit. Well, you may know the chaos is the name of the game here in mom's basement, what with

• 4:14Speaker 04

  guests coming in and out, Cooper the cat getting in the way, Doug being, well, being Doug. The holidays make it even worse because it's all about food and big meals. And the problem is prepping for those takes forever. But what about those between meals, right? The meals between those huge, huge, huge bookends? Well, that's where Factor comes in. Factor is made with high quality ingredients that you recognize and trust with over 175 banned ingredients. You always know you're eating something that's good for you, even when you don't have time. It's ready in two minutes. Whether it's lunch between meetings or dinner after holiday shopping, Factor requires zero

• 4:55Speaker 04

  prep cleanup or effort from you or mom, so you can focus on everything else in your day. Factor even has heart smart options like the Green Goddess Bar Mundi with tomato, rice, peas, kale and green beans, or the enchilada style chicken and sweet potatoes. Those are so good. They're crafted with lean proteins, fiber packed fruit and veggies and healthy fats. Try those out. Your heart and your taste buds will thank you. For Cheryl and I, Factor has been a great way for us to stay busy and focus on family life and beating mom at card games. I use Factor and you should too. So let's eat real, stackers.

• 5:40Speaker 04

  Head to factormeals.com/sb50off. Use code SB50OFF. And you know what? You're going to get 50% off and one free breakfast item per box for one year while supplies last until December 31st, 2026. That is code SB50OFF at factormeals.com, SB50OFF at factormeals.com. See website for more details.

• 6:10Speaker 04

  Big news, Anna, when it comes to student loan repayment plans, for people that are enrolling in some of these plans, you've got a chance. I thought everybody had missed their chance because the original deadline was October 1st to get a 1% discount on repayments to your student loans. But that's been put off to the end of the year. What's up with student loans this year? There's, there's a lot up with student loans this year, isn't there?

• 6:38Speaker 05

  There's a lot going on with student loans. It's, it's kind of hard to keep track. And also a lot of the changes kind of rolled out over a year ago, but aren't taking effect until now or the middle of 2027. So some of this stuff I've really just pushed to the back of my brain because it was such a long timeline as to when we actually had to do anything about them.

• 7:00Speaker 04

  And that's the, for me, that's the problem. Like on one hand, the government goes, okay, we'll give you more time. I think the problem is, is that it's not immediate. And so we just forget about it. And then all of a sudden we wake up, we're like, oh, it was due yesterday. Like I need to do this before.

• 7:15Speaker 05

  I should have done something. Yeah, I should have done something because when it rolls out, the other thing is when a lot of these changes do come about, you just think, okay, well, so much could change between now and then. New laws could come in place. It could go through Supreme Court. Like there's just been so much stuff that's been changing and then also gone back on that it's hard to just keep track of what is actually happening. So yeah, it's exciting that the 1% discount is going to be put in place for anyone who does the auto enroll before the end of the year.

• 7:47Speaker 04

  When it comes to choosing a plan for most people, Anna, that date has already come and gone. Here's, here's the way that this works, and I'll apologize for the spaghetti. We didn't create it. The government created this mess. We're just going to try to help you interpret it, stackers. You had 90 days and for most people, that 90 days is already up. If you were in the save plan, you received a notice and that was on a rolling schedule. So maybe you didn't get your notice until maybe the 21st, maybe the end of the month. If so, you might still have a couple of days left to choose what plan you went into. But if not, you went into one of two plans.

• 8:30Speaker 04

  You either went into the standard repayment plan or the tiered standard plan with fixed payments over 10 to 25 years based on your balance. I think the first thing, Anna, is just to go in. If, if you were in the save plan and you didn't do anything, the first thing to do is just go check out which plan you're in.

• 8:50Speaker 05

  Yeah, figure out what your payment is going to be and just an understanding of generally what you're going to be looking at for potentially the next 10 years.

• 9:00Speaker 04

  Your servicer's notice will give you your exact deadline. So if you were in the save plan, you want to go in and check and see what that exact deadline is. So if for some reason you have the ability to act now, fantastic. If not, just try to minimize the damage by figuring out your financial plan around it. But there is another deadline looming, which is people can get 1% off the interest they pay. Anna, how does that work?

• 9:25Speaker 05

  Actually, this was already kind of a program in place where if you were auto enrolled, you got a quarter of a percentage off. So you got a small interest deduction if you were auto enrolled and they've bumped that up to now 1% off of your interest rate if you enroll in auto payments. So every month, it's just automatically going to take those payments out. If you get that set up, you get that discount, which is really, really nice.

• 9:53Speaker 04

  That is really nice because, well, two things. Number one, I mean, if you've got a $50,000 loan and it goes from 7% to 6% over 10 years, that saves you about three grand. That's not a small amount of money.

• 10:04Speaker 05

  Yeah, definitely recommend getting that. I mean, whether or not you have a potential interest rate deduction, auto enroll for student loans just makes sense. You don't want to be messing around with that. There's no, it's not like the same as credit cards where you're like, oh, let me make sure everything's correct. Like, it's going to be the same payment every single month unless you're in some sort of variable interest rate. So you should be expecting that every single month and it should be on high priority to get that debt paid monthly.

• 10:32Speaker 04

  This was a problem I had with my money when I first started out. Once I found out that I could defer my student loan payments, oh my God, Anna, I was a deferral machine. I was like, if I can stop making payments, that's great. I didn't even realize these were unsubsidized loans, which meant that the interest kept accruing. I was just, I just wasn't making payments, but I owed more and more money. So I love this idea. Prioritize it. Get rid of your student loans.

• 10:54Speaker 05

  Yeah, absolutely. It's really important and you should just automatically be taking advantage of this interest rate deduction if you can.

• 11:02Speaker 04

  You know, what's funny is let's say that you've got a 7% rate. You know, often we look at this 1% and we think, well, 1%, big deal. It's not that big a deal, even though I just went over, you could save three grand if you had $50,000 in loans. But if your loan rate was 7% and now it's 6%, you just saved one seventh, you just saved 1%. You saved one seventh of, of the total interest you were paying, like ching. It's a much, much, much bigger number when you think about it that way.

• 11:33Speaker 05

  Yeah. And that monthly payment will be less then. So it's just all around a good decision if you can do that. And again, like, like I said, even if you couldn't get the interest rate, you should be signing up for this regardless.

• 11:44Speaker 04

  How do you look at, you know, when somebody's evaluating colleges? Cause there's a lot of kids out there, a lot of families where they're evaluating colleges, maybe right now, maybe in the next four, five, six years. When you're evaluating two colleges and one you have to take student loans out and the other one you don't, is there a way that maybe you help people think about this debt load and whether it's worth it or not?

• 12:06Speaker 05

  Yeah, that's a really good question. I mean, it's, it's going to come down to, I mean, this is kind of obvious, but like what schools are you looking at in terms of, are you looking at a school that maybe doesn't have everything that you are looking to do? What are you looking to do after school? Is it going to be easy for you to pay those student loans off? So there's a lot of different conversations around this in terms of-

• 12:33Speaker 04

  I'm sorry, but in other words, what's the ROI on the debt?

• 12:36Speaker 05

  Yeah. I mean, college is still a life experience. And if you want to go there and it, one college is really important for you because not only are you coming out and you're going to have a great job, but it's also a safer campus or it's closer to home and you can live at home. Or there's different things that are involved in that decision, not just the fact that you might come away with some debt. And how much debt are we talking to? Because that's huge. It's good to, for kids to understand like what that's going to look like when they graduate, because that's going to be a huge wake up call. They get into the workforce and especially if they're moving out and they're not going to live at home anymore. And they have these giant student loan payments that they're

• 13:16Speaker 05

  now obligated to pay for another 10 years. That's going to set them back potentially from like buying a house or paying for a wedding or something like that. There's a lot that goes on in those first 10 years out of college.

• 13:28Speaker 04

  It's funny. I had a family member I was talking with about this and the family member I vehemently disagreed with because he said, my job is to be a cheerleader for my kids. And if they want to do it, like go do it, go do it. And I thought, well, yes, like you can do anything you want, but also knowing what the trade off is going to be, right? I mean, there is a trade off. Maybe, do you like the idea of predicting what the debt's going to be and showing them what the monthly payment's going to be even before they go to college?

• 13:57Speaker 05

  Yeah. I think if it's the kid's responsibility, it's your responsibility as the parent to make sure that they're aware of that and what that means for them. Okay. So here is probably what your salary is going to be when you come out of college, if you're going to graduate with an accounting degree or whatever the degree is.

• 14:11Speaker 04

  You can get that, by the way, from a place like Glassdoor or the Bureau of Labor Statistics. We'll have links in our show notes where you can get those numbers. Cause Anna, these numbers are so important to go over with your children during their college experience.

• 14:24Speaker 05

  Yeah. I mean, if parents are paying for the, if they're taking out some debt just so that they can pay for it, then over a longer period of time, then go for it. Be the cheerleader for your kid and don't let them worry about what college is going to cost and, you know, let them go wherever they want. But if that's their responsibility to pay for that at the other end of it, it's so important that they're aware of what that means to them, how that's going to impact them. Cause maybe the kid is going to say, hey, actually it's more important for me to be able to go live in New York City or in a very high expense area. That's what they really want post-college. They might not be able to swing that on an entry level salary with student loans as well. So it's,

• 15:05Speaker 05

  you know, part of the decision-making skills and also this is just really good way to start introducing them to financial planning and, and what that means on a personal level for them. So having that conversation is very important for a parent.

• 15:20Speaker 04

  Both of my kids, we went through this with, and at different stages, Anna, they're both doing very well. They're 32, they're doing great. But my son was choosing between Carnegie Mellon, fantastic university in Pittsburgh and the University of Texas, which was in-state, state school. What we did for Nick, because as a family, we could afford both schools. Cheryl and I, in our family, we were going to pay for it. But what we wanted to make sure was that Nick understood the financial repercussions of school A versus school B. We gave him the cost of enrollment of both of these schools, what they were

• 16:00Speaker 04

  going to cost. And Carnegie Mellon being a fantastic private university was, I don't remember the number, but, but four or five X, right? Yeah. I mean, it was, it was much, much higher than the University of Texas in-state. And I said to Nick, I said, there are so many things, like as you said, Anna, you're going to have things that go on in campus. You're going to have these people that you're going to interface with. You're going to have these opportunities that maybe you don't get at another campus. And I said to Nick, if you can articulate for me what Carnegie Mellon will do that you won't get at the University of Texas, then we should choose Carnegie Mellon. We should easily choose it. And, and I was hoping, by the way, that he would do that, that he would

• 16:45Speaker 04

  do that research. Now, the good news was-

• 16:47Speaker 03

  Were you going to make him create a PowerPoint?

• 16:49Speaker 04

  Well, yeah, it's almost like when we were working with Karen Holland almost a year ago, Doug, you know, with her doesn't make sense score for middle schoolers. I think it's the same thing. You know, she has kids before they say, hey, let's get a puppy, right? Go through who's going to feed it. What's the cost of care? What's it going to be? And do I really want all the stuff that comes with the puppy? Though she used, you know, last year's World Cup games as another example, like the family going to the World Cup could be a great experience for the family. And if the middle schooler says, yeah, I want this as my gift for the holidays or for my birthday to go to a World Cup game. Well, let's walk through the doesn't make sense score. Cause A, the kid doesn't want the family to be destitute and B, you know, kids don't want gifts that they don't care about.

• 17:33Speaker 04

  They don't, they don't want to be shoved into a thing that they, in this case, a college experience that they haven't quantified. So 100% do the PowerPoint, Doug.

• 17:42Speaker 04

  So I was hoping that he would, but much like me at 18 and a lot of kids at 18, Nick was pretty immature at the time and couldn't articulate any of that. And then he decided, he goes, you know what? I think because I can't articulate that, I'm going to go to the University of Texas. And by the way, still loves the fact that he was a Longhorn, like still at 32 years old, like so invested in the fact that he went there and so happy that he went there.

• 18:09Speaker 03

  I know somebody that somewhat related to that story, but almost the, I kind of like your approach. The, the, the end of what I'm about to say is to say, I like the way you did that, Joe, because I know somebody else very well, who initially said to each of their kids, this is how much we have saved for you for college. And the, these people are very financially successful. They more than likely could have paid for all of their kids, you know, four-year degrees. They have three kids, but instead they said, here's how much we have, you can pick, but if you pick a college that is going to be more cumulatively for four years than what we have saved, it's on you.

• 18:45Speaker 04

  It's on you.

• 18:45Speaker 03

  And two of their kids chose schools that were very, very expensive, so much so that they were beyond what the allotted savings was, uh, some of the most expensive in the country. And they, one of them was getting student loans. They ran out of money by second semester sophomore year, and they were getting massive student loans, uh, because they thought this is a great school. I want to go to it, just like Nick might've thought Carnegie, Carnegie Mellon's an amazing school. I want to go there.

• 19:14Speaker 04

  Yeah.

• 19:15Speaker 03

  And have that name on my, without really doing a deeper dive to figure out what's better about that than UT in your case. And I, I wish this couple would have done what you just suggested, which is let's, let's go through it, figure out what are you getting out of that, that you're not getting out of the other school. Cause I think that changes a lot of decisions.

• 19:31Speaker 04

  And that wasn't a trick on my part.

• 19:33Speaker 03

  Oh, right.

• 19:34Speaker 04

  I mean, there are definitely things at Carnegie Mellon that, that you can't get other places. I've got friends, you know, I grew up just north of Notre Dame and their alumni network is, you guys may or may not know, is incredibly powerful, like-

• 19:45Speaker 03

  Obnoxious football fans?

• 19:46Speaker 04

  Oh, sorry. Just, just your ability to use that, if you are mature enough to do it, to leverage opportunities to maybe get introduced to jobs is huge. Notre Dame people take care of Notre Dame people. It is big and I'm sure it's the same for Carnegie Mellon. I'm sure it's the same for a lot of these wonderful, expensive colleges. Uh, he couldn't articulate any of that though, and it didn't matter to him. If it would have mattered, we would have done it. My daughter, it was, it was a different thing, similar, but different. My daughter was choosing between two different majors. She liked to write, so she was either going to do creative writing or journalism, or she wanted to be a brain surgeon, like one or-

• 20:29Speaker 05

  Whoa.

• 20:30Speaker 04

  I know, right? Cause she also really liked science. So she got dad's side, the journalism side, and then she gets mom's side, the science side. And all we did, to your point here, Anna, was we went to the Bureau of Labor Statistics. And I said, I work with a lot of people who work in journalism, related fields like public relations, whatever. You're going to make $52,000 a year. You're going to work your ass off. And don't get me wrong, all these people I interface with, they love it. It's going to be fantastic, but it will consume you and you're not going to make much money. That is just the way, I mean, unless you're some kind of unicorn, it's going to be very difficult, especially when you're starting out, like you're going to have to hustle because there's low barriers to entry and a lot of people fighting for a limited pie of money.

• 21:14Speaker 04

  Brain surgery out of college, $320,000, right? And, uh, and you're still going to work a lot. It's going to be tough. It's going to be life and death stuff you're working on. So emotional stuff going on, but economically it's going to be fine. She decided to major in biology, heading toward becoming a brain surgeon and minor in journalism so that she could get the fun stuff. And she's like, well, maybe I'll start a blog as a brain surgeon. Maybe I'll, you know, have some fun on the internet with this stuff.

• 21:48Speaker 05

  Still be able to get into those skills. Yeah.

• 21:51Speaker 04

  Yes. And that went great until organic chemistry hit. And when, and for anybody in the sciences knows, organic chemistry is the great weeder outer of potential doctors.

• 21:59Speaker 03

  That's the weed out class.

• 22:00Speaker 04

  That's the one. So then Autumn switched to being a journalism major, but guess what my daughter got? She got hustle because she knew, because we'd gone to the Bureau of Labor Statistics and seen the numbers. My daughter realized, and she's been a hustler ever since. She's like, I know, I knew I needed to hustle because we went over what it would look like. I think that's a great thing for any parent to do.

• 22:20Speaker 05

  I think that's a great thing. I, I like when parents are, and this is something that I really want to do for my kids is like, make sure if they come to me and they say that like they want to be a dance major or whatever, it's not crushing the dream, but it's just saying, here is what your reality might look like. Here are the different paths within that. If you're okay with that and you feel good about that, then let's do it. Like that's, that's great.

• 22:43Speaker 04

  But there is a reality that we need to face.

• 22:45Speaker 05

  Yeah.

• 22:46Speaker 03

  Joey, this discussion about, you know, making sure college pays off and whether it should or not, reminds me of a great stand-up bit that just, it caught my ear the other day, and I think it's really funny.

• 22:57Speaker 06

  Yeah, I was lucky enough to have dropped out. Um, cause I realized early on that these, these student loans are basically small business loans and the business is you and you're maybe not such a great business. Look, if they call them small business loans, no 18-year-old kid would ever get the loan because it's a bad idea for a business. If you had to go to the bank, to the small business desk and ask me like, yeah, I'm going to need a hundred and $50,000. They'd be like, all right, what's your business idea? All right, here's the idea. For the next four years, I'm going to get blackout drunk. But also I'm going to get a degree in sociology.

• 23:39Speaker 03

  They'd be like, get the [bleep] out of our bank.

• 23:46Speaker 04

  They might not be that happy with it, but this is back to your point, Anna. That's why it's important to have these ROI discussions ahead of time, especially if you're going to go into debt. If you're going to go into debt, there's got to be some ROI. And you know, we just want to be the people that help you put on a brave face, whether you are applying for colleges or you're applying for jobs. There's a lot of rejection out there right now, people. Hamesh Patel has written a letter that maybe we should all get ready so that we can fight off all this adversity that we're seeing.

• 24:22Speaker 07

  Office of Admissions, dear sir, madam, having reviewed the many rejection letters I have received in the last few weeks, it is with great regret that I must inform you, I am unable to accept your rejection at this time. This year, after applying to a great many colleges and universities, I received an especially fine crop of rejection letters. Unfortunately, the number of rejections that I can accept is limited. Each of my rejections was reviewed carefully and on an individual basis.

• 25:04Speaker 04

  I'm sorry, I can't accept her. That's what we all have to just write that letter from time to time.

• 25:10Speaker 03

  So good.

• 25:11Speaker 04

  Yeah, good stuff. All right, let's pivot, Steve. That's not the only deadline at the end of the year, Anna. The fact that you might, if you're looking at your student loans, get 1% off, which you should take advantage of. Also, there's this deal that people over 65 might have. You can roll $47,500 out of your traditional IRAs, potentially, and move that over to a Roth IRA without any tax? What's this magic trick all about, Anna?

• 25:42Speaker 05

  Asterisk, asterisk, asterisk, asterisk.

• 25:44Speaker 04

  Is this like the pharmaceutical ad where like the first 10 seconds is the ad and then the next 29 seconds or 20 seconds is all the disclaimers?

• 25:54Speaker 05

  Yeah, my husband and I were just watching some baseball playoffs and you know, there, it's just all drug ads at that point. And one of them was, you know, the classic, don't take Skyrisi if you are allergic to Skyrisi. It's just like, that is my favorite. And it also just reminds me of like where we're at as a population and it's just so sad. Anyways, back to Roth conversions.

• 26:18Speaker 04

  Yeah, 47.5.

• 26:20Speaker 05

  Yeah, that's amazing. If you have no income, like if there's no other reportable income for the year, then yes, you can convert some money over tax-free. So if you have $0 in reportable income for that year, then yes, you can convert up to $47,500 because we have the standard deduction plus an enhanced senior deduction for 2026. So again, this is for people who are above 65. If you're below 65, we can still do Roth conversions. It's just, um, and up to tax-free, but it's just that it has to be below that standard deduction that everyone qualifies for every year.

• 26:58Speaker 04

  Let's go over what all the different parts are. The standard deduction is if you're somebody that can't do itemized deductions, which now I think Anna is probably the majority of us, right? I mean, by far, the majority of us.

• 27:10Speaker 05

  Well, I mean, with the new SALT deduction, that's been increased. It is a majority of us, but you would be surprised. And definitely, I know this is kind of like a tangent on another path, but like, make sure that you're looking into if you qualify for itemized deduction this year, and last year was also part of that. But because of that increased in the SALT deduction, which is built with-

• 27:32Speaker 03

  Was it deduction for the Strategic Arms Limitation Treaty?

• 27:35Speaker 04

  That's, that's what I was about to-

• 27:36Speaker 05

  Exactly, Doug.

• 27:37Speaker 04

  Yeah, what is it, Anna? What is the SALT deduction?

• 27:40Speaker 05

  So, SALT deduction is primarily made up of your state and local tax. So if you live in a state where you have to pay state taxes, that's part of it. Your real estate tax, your property taxes on your house that you pay every year. If you have high property taxes, that can help increase your SALT deduction. There might even be some other things included in that. But those are the two primary drivers of a higher SALT deduction. And usually, they're, they were previously capped at $10,000. And there are some people, if your income is above like $500,000 or $600,000 a year for a married couple, you're probably still capped at that $10,000.

• 28:20Speaker 05

  But there is this like sweet spot of high income earners who aren't above that $500,000 who have a high state tax, who can actually deduct up to $40,000 within a SALT deduction.

• 28:35Speaker 04

  There you go.

• 28:35Speaker 05

  So you just went from a 10K cap to now a 40K cap. Then you add the mortgage interest on top of that. You add maybe some charitable contributions on top of that. And you're over that $32,000, whatever it is for our standard deduction for this year. So it's important, if you're working with CPA, if you're reporting this to yourself, just do the exercise to make sure that you can't itemize this year.

• 28:58Speaker 04

  Check the box.

• 28:58Speaker 05

  It might, yeah, you might fall into that category and you might not. And then you get a good standard deduction too.

• 29:05Speaker 04

  But if you're somebody that gets the standard deduction and you are a married couple 65 plus, these age-based additions that are going to phase out at the end of this year, partially, some of them are going to phase out the end of this year, is what creates this magical sweet spot of $47,500. It's in your traditional IRA that you can move over to a Roth IRA. We might be able to do this if we're over 65. But there's also, Anna, a lot of reasons people might not want to. You might be eligible for it. It might look good on paper, but there might be a lot of reasons you don't want to do this. So why would somebody not want to do this if they're eligible?

• 29:43Speaker 05

  If you're eligible to move money over tax-free from a traditional IRA to a Roth, so you have no other reportable income, we can move that full amount over into a Roth. I don't see the reason why you wouldn't want to do that. I mean, if you can move it tax-free.

• 30:00Speaker 04

  Yeah, I just saw one thing that said that if you have $380,000 or less, you're going to be in the lowest tax bracket anyway. So, you know, conversion, eh?

• 30:12Speaker 05

  But it's tax-free.

• 30:14Speaker 04

  But it's tax-free.

• 30:15Speaker 05

  It's tax-free now, so I mean, why wait? I mean, that, that conversation comes into play when we're talking about, oh, this is a taxable event and we are, we have a IRA balance that isn't astronomical and we want to convert a large amount. We're getting into like the 22%, 24% bracket in your retiree. Yeah, I see why we wouldn't maybe necessarily have to do any sort of conversion. But when it's a tax-free conversion, I don't see how that could be a negative.

• 30:46Speaker 04

  No, and it's funny, as I think through this, this piece that says conversion is unnecessary. I also think that if you do this now and the IRA grows between now and the time that you start taking out your required minimum distributions, because the reason why it's unnecessary stackers is because your standard deduction is going to wipe out any of the tax that you would have paid anyway, so it's already tax-free. But if it grows between now and 75 and you start taking minimum distributions out at 75, well then, okay, now you will have some tax, so.

• 31:20Speaker 05

  Also, like, we don't know what tax brackets are going to look like when you're actually 75. That's 10 years away. Who knows who's going to be in office at that time? What tax brackets are going to look like? If that actual taxable number is going to increase, like that percentage? If that deduction's going to be taken away? So, so much can change. If you have the ability to do this, do it now.

• 31:41Speaker 04

  I think the big issue is with people earning money for a longer period of time, that no other income is going to be a big piece of it. But what about IRMA? People also caution you about IRMA. What is IRMA and why should we be wary of this?

• 31:56Speaker 05

  IRMA is a increased Medicare premium. This is why when you get to be close to age 65 and we start talking about Roth conversions. So this is, actually, IRMA is something we start to consider when you're 63 because Medicare is going to calculate your premium from tax returns from two years ago. So we need to make sure that we're being very aware of this well ahead of you actually starting Medicare. If your income jumps during a year that, leading up to Medicare, like I said, at 63, or while you're actually in Medicare ages, those premiums, like you might not just pay the base amount,

• 32:39Speaker 05

  they're going to add another premium on top of that so that your Medicare premiums are going to be much higher than just like maybe what you normally would have anticipated.

• 32:49Speaker 04

  I love this idea of getting to know IRMA ahead of time, which is why I wanted to talk about it. Because even if you're in your early 50s now, stackers, like knowing this stuff is coming, the earlier that you know, the better you can make plans, like starting to use the Roth option in your 401K versus the traditional option that a lot of people, you know, a lot of people use. I was talking to a friend of mine just yesterday who is having his 60th birthday and he's thinking about Roth conversions, but he's still in a very high tax bracket. And he's like, do I convert it when I'm at this high tax bracket? Like, he's trapped with all this money that's sitting in traditional accounts.

• 33:27Speaker 05

  Yeah, that's why I find Roth conversions to be the most appealing between, like if someone retires in their mid to late 50s, their income might be down. We might not even be able to access those retirement accounts without some sort of penalty. So normally, we're accessing brokerage account for portable income, or taxable income, sorry, becomes much lower. And those are the years, actually, that Roth conversions are the most important for me. Because once we get to 63, that number, A, we might be tapping already into IRA for your actual income. So income may have jumped from, you know, 58 to then whatever you were taking at 58 versus what you were taking at 62 or something.

• 34:12Speaker 05

  That's the magical band that I look at when we're talking about Roth conversions. Always, there's the possibility after that of leading up until you actually have to take RMDs. But I really like to do larger ones during those younger years.

• 34:27Speaker 04

  It helps you build in so much flexibility if you start planning this well, well, well before 60. And what always made me sad when I was a financial planner was people would walk in, you know, two months before retirement. And, you know, we can do something, but man, if you'd started this at age 30, we could have done so, so, so much more.

• 34:46Speaker 05

  Yeah.

• 34:47Speaker 04

  In the second half of today's discussion, Anna and I are going to take a question from Drew. Drew's got a great question about disability coverage. This is such an important coverage. It's something people don't want to talk about, which is exactly why we're going to talk about it today. And some of the problems of maybe not just applying for disability, but being, having a disability company say, yeah, we'll take on your risk. That's coming up in the second half. But if either of these topics, student loans or tax planning for retirement affect you, we've got some guides that go over these. It's at stackyourbenjamins.com/guides. We have three guides, guide to your HR and benefits, a guide to college planning, which we discussed in the first half, and then guide to your taxes, which we describe later.

• 35:31Speaker 04

  You also get a discount on our guides if you buy two, even bigger discount if you buy all three. So stackyourbenjamins.com/guides. All right, Doug, man, you made a big promise and that's that today's trivia is fantastic. Tell me it's so.

• 35:45Speaker 03

  That's a promise that's easy to keep, Joe. Hey there, stackers. I'm heavyweight champion of the cul-de-sac and guy who's left hook once knocked over an entire bowl of queso, Joe's mom's neighbor Doug. Happy birthday today to boxing legend Evander Holyfield. Holyfield was known as the real deal, became heavyweight champion of the world and knew a thing or two about delivering a punch, which is appropriate today because Wall Street has also taken some legendary punches in October over the years. In fact, more than one particularly ugly day has earned the nickname Black Monday. So today, we're putting the Black Mondays in the ring. Which one delivered the biggest one-day percentage punch to the Dow?

• 36:28Speaker 03

  Was it Black Monday during the famous 1929 stock market crash? Black Monday on October 19th, 1987? Or one of the brutal Monday sell-offs during the 2020 COVID crash? Which Black Monday hit investors hardest? I'll be back with the answer right after I clean up that queso. Apparently, knocking it out and knocking it over are two very different things, according to Joe's mom.

• 36:54Speaker 04

  Well, you may know that chaos is the name of the game here in mom's basement. What with guests coming in and out, Cooper the cat getting in the way, Doug being, well, being Doug, the holidays make it even worse because it's all about food and big meals. And the problem is prepping for those takes forever. But what about those between meals, right? The meals between those huge, huge, huge bookends. Well, that's where factor comes in. Factor is made with high quality ingredients that you recognize and trust with over 175 banned ingredients. You always know you're eating something that's good for you, even when you don't have time. It's ready in two minutes, whether it's lunch between meetings or dinner after holiday shopping.

• 37:38Speaker 04

  Factor requires zero prep cleanup or effort from you or mom. So you can focus on everything else in your day. Factor even has heart smart options like the green goddess barramundi with tomato, rice, peas, kale, and green beans, or the enchilada style chicken and sweet potatoes. Those are so good. They're crafted with lean proteins, fiber packed fruit and veggies and healthy fats. Try those out. Your heart and your taste buds will thank you. For Cheryl and I, factor has been a great way for us to stay busy and focus on family life and beating mom at card games. I use factor and you should too.

• 38:23Speaker 04

  So let's eat real stackers. Head to factormeals.com/ sb50off. Use code sb50off. And you know what? You're going to get 50% off and one free breakfast item per box for one year while supplies last until December 31st, 2026. That is code sb50off at factormeals.com, sb50off at factormeals.com. See website for more details. There is a financial conversation that's coming to millions of American families and there's a pretty good chance nobody wants to be the person who starts it. Inheritance. And here's why that matters. An estimated $124 trillion to heirs and charity is expected to be transferred by Americans

• 39:08Speaker 04

  over the next 20 years. It's an extraordinary amount of money, but Kiplinger's research found that 51% of adults and their parents, get this, never talk about money. And there's a pretty big disconnect. 47% of parents expect to leave a meaningful inheritance while only 24% of adult children expect to actually receive one. Nearly 30% of parents don't even have a will in place. Maybe it's time we talked. Kiplinger calls it the trillion dollar talk, a conversation about inheritance, estate planning, wills, and the questions families should be asking before those decisions become urgent, because knowing what your family wants and having a plan for it can be one

• 39:53Speaker 04

  of the most important financial conversations you will ever have. Ready to start yours? Visit kiplinger.com to learn more about the trillion dollar talk and what this historic wealth transfer could mean for your family.

• 40:07Speaker 04

  It's incredible at a small company like stacking Benjamins, how one, one hire makes all the difference in the world. If you're a small business, the right hire can be make or break. Hoping the right people see your job posting isn't the best growth strategy. When the pressure's on, you need the right hire. This is a job for sponsored jobs. Indeed sponsored jobs is a boost whenever you need to find quality talent. When workplace chaos hits and you need the right hire, this is a job for sponsored jobs. Hiring indeed is all you need. Stop struggling to get your job post even seen at other sites. Get matched with and hire quality candidates who can drive the results you need. Reach candidates that meet your specific criteria like skills, certifications, or

• 40:52Speaker 04

  locations. Sponsored jobs boost your job post on search results. So you can reach the people that can help your business thrive. Plus with indeed sponsored jobs, you only pay for results. People are finding quality hires on indeed right now. In the minute I've been talking to you, listen to this, companies like yours have made 27 hires on indeed, according to indeed data worldwide. And sponsored jobs posted directly on indeed are 95% more likely to report a hire than non-sponsored jobs. So spend less time searching and more time actually interviewing candidates who check all your boxes, less stress, less time, more results. When you need the right person to cut through the chaos, that's a job for indeed sponsored jobs. And guess what?

• 41:35Speaker 04

  Our stackers are going to get a $75 sponsored job credit. That's you to help get your job, the premium status it deserves at indeed.com/podcast. Just go to indeed.com/podcast right now and support stacking Benjamins by saying you heard about indeed in mom's basement. Indeed.com/podcast. Terms and conditions apply. Need a hiring hero? This is a job for indeed sponsored jobs.

• 42:10Speaker 03

  Hey there stackers. I'm certified ringside financial analyst and guy who once went nine rounds with a fitted sheet, Joe's mom's neighbor Doug. Before, those things suck. Before the break, in honor of birthday boy and boxing legend Evander Holyfield, I put three of Wall Street's biggest punches into the ring to let him duke it out. Three black Mondays, but which one hit investors the hardest? Let's get ready to. What's that? Oh God, that's right. We can't do that. Apparently we're not allowed to say that. Fine. Round one. Our first contender, Black Monday, 1929. This is the one everybody remembers from history class, the great crash, depression on the way, people staring sadly at ticker tape.

• 42:55Speaker 03

  How hard did that Monday hit? The Dow fell nearly 13% in a single day. That is going to leave a mark. Next into the ring, 2020 pandemic, markets panicking, everybody's suddenly learning what zoom is. On March 16th, the Dow suffered one of the worst days in its history, dropping about 13%. Another huge right hand, but neither one is our champ because on this very date, October 19th, 1987, Wall Street walked into the ring and somebody apparently forgot to tell it to keep his hands up because the Dow fell 508 points that day. And remember this was 1987 when 508 points wasn't something CNBC called a choppy Tuesday.

• 43:41Speaker 03

  That represented a staggering 22.6% decline in one day. And it remains the Dow's largest one day percentage decline in history. Nearly a quarter of the Dow gone, just gone. So congratulations, if you picked Black Monday, 1987, you just survived three rounds with Wall Street. And unlike my bout with the queso, Wall Street didn't have to explain the stain on Joe's mom's carpet afterwards. Speaking of taking a punch and getting back up, Joe and Anna are about to help make sure your financial plan can stay on its feet. Take it away, you crazy kids.

• 44:22Speaker 04

  You know, it's interesting. My, my father-in-law was very open about this. And on that day in 1987, he took his money out of his funds because he thought it was going to get worse after the 22% decline. He took his money out and it was a warning to me and to everybody. Like he told this openly, there were two problems. Number one was he didn't expect what was about to happen, which was it was a jackknife. I mean, it was just a knife. It went down, it cut 22 the next day, it roared back a ton. So he locked in all these huge losses. Problem number one. Problem number two was he didn't realize how mutual funds worked. And if you have mutual funds, you can call your person anytime, you can make the trade at anytime. Mutual fund trades happen at 4:00 PM.

• 45:06Speaker 04

  So he made the trade at 9:30 in the morning Eastern time, Anna, thinking that he had survived most of the day, not realizing that right at the bottom, at the end of the day was when he actually sold. He could have called at 3:30 in the afternoon. It would have been the same thing.

• 45:22Speaker 05

  Wow, that's really sad.

• 45:24Speaker 04

  Yeah. It was great that he was open about it though, because it was a lesson that we all remember. He's like, learn from my mistakes. Hey, speaking of that, somebody has made, well, not a mistake, but they definitely wanted some help and they said, better call Saul.

• 45:40Speaker 04

  See, I and Anna, that is, this is the part of the show where we take one of your question stackers, head to stackingbenjamins.com/ yelled downstairs and we're happy to answer your question like this one that comes to us from stacker Drew. Hey Drew.

• 46:01Speaker 06

  Hey Joe and OG, this is Drew from St. Charles, Illinois, calling with a question about disability insurance. My wife has had some major medical issues her entire life since she was born. It's caused some mobility issues in the past, but she's been able to walk just fine. But lately her knees have taken a turn for the worse and we're not entirely certain if there's going to be a medical solution to what she's been experiencing. We've tried to apply for some disability insurance recently, but it will exclude anything that might be caused by her legs, which is the main issue we're trying to address. So I'm just wondering if you have any suggestions for what we can shop around for long or short-term disability? Or if that is an option, if we should look into self-insuring.

• 46:47Speaker 06

  As background, my wife is self-employed, but she's looking to potentially get back into the workforce in the future. We have $80,000 on our HSA. We are debt-free aside from our mortgage, which has $130,000 left. And we have a three-month emergency fund. I love the podcast and would appreciate your input here. Thanks.

• 47:11Speaker 04

  Drew, thank you so much for the question. What an important thing that people don't want to talk about. And I mentioned that earlier, but I felt like back in my planning days, whenever I brought up disability coverage, people are like, oh, look at the time. Let's, let's, let's talk about something a lot more fun than this.

• 47:28Speaker 05

  We're talking to all of our clients right now about disability insurance. So it is a daily conversation for me and it's not fun.

• 47:35Speaker 04

  But the statistics are why you're doing it. Cause the statistics around disability, man, they say to cover the stuff where it might happen to you, there's a much better chance of at least a short-term disability than we want to believe.

• 47:48Speaker 05

  Yeah, people are a little bit more easy to get on board with a life insurance policy. I'm thinking about like their own death, which is interesting, but they're much more likely to experience a disability. Yeah, they're much more likely to experience a disability than, and I think maybe it comes down to people thinking they'll just like push through it or like what happens to them won't stop them from working or they'll find a different job or whatever it is. I don't know exactly the psychological part of that, but you are way more likely to experience some sort of disability and you have no idea what that's going to entail, what it's going to look like, how it's going to feel on your body, what capacity you can continue to work.

• 48:30Speaker 05

  And so it's really important to have the conversation. And in Drew's case, in his family's case, it might not result in that you have a disability policy in place because you can't. But what is the plan instead then? What is that going to look like if that becomes a reality for your family?

• 48:50Speaker 04

  This is such an interesting topic because I think first Drew, we have to look at it from the insurance company's point of view. Whenever somebody came into my office and they're like, hey, I'm thinking about applying for disability insurance. I was always, and I was always like, okay, so what happened? Oh, well, I hurt my back at work. Guess what? That event happened. Yeah. It is my same father-in-law, and he was very open about this. Finally wanted to talk about long-term care the day after he was diagnosed with Parkinson's disease. That was the first time he was open to it. He was like, hey, uh, let's talk about long-term care. Guess what? Uh, yeah.

• 49:30Speaker 05

  Yeah, but it's on your medical record. There's no way that they're not going to see that and they're going to exclude anything. I mean, they might not, they might not even insure you.

• 49:40Speaker 04

  So Drew already talked a little bit about this, like what would it look like self-insure? So maybe we start there. What does he do? Does he show his spouse with a few years not bringing in any income? Does he like, what is he, how does he kind of model that?

• 49:56Speaker 05

  Yeah, I think it's running through a plan of, you know, understanding how much of your actual spending is reliant on that person's income and their ability to work and to work at that capacity. Understanding then the next part, which is how much do we rely on them for savings for retirement? What is the plan? Can we cut back certain expenses if this were to become a reality and we have to go down this route? Or are we pretty much like at the bare minimum right now? Um, and we rely on them for, you know, 50% of our spending, they bring in that much income. So understanding that is the first part of this.

• 50:39Speaker 04

  What kind of a crater is there going to be when she is fully disabled?

• 50:44Speaker 05

  Yeah. Then what is, what, how do we pivot from there? Is your wife going to, like right now, is she doing something where it's very physical? And at that point, maybe we could pivot to like a profession where it's more sedentary and we're sitting down. It's less physical. Can he take on an additional income stream, whatever that looks like? Figuring out what is the plan at that point? Especially because in this situation, like that sounds like it really could be a reality for you. We're not talking about someone who is a hundred percent healthy. We have no idea how some sort of disability could take their ability to work away from them.

• 51:27Speaker 04

  Right.

• 51:28Speaker 05

  Whether it's mental or physical, you know, however that goes. So it's, you know, really important for you guys to model out what is the decision-making when we get to that point.

• 51:38Speaker 04

  And I think that is an advantage for Drew and his spouse, which by the way, having a disability already is not an advantage, but their ability to model what it would look like. They have, I think a leg up because they can already see what it would probably and potentially look like versus, versus somebody who's not already experiencing some disability. Does he apply for disability coverage outside of this? So they want to exclude, and once again, we need to think like the insurance company. The insurance company definitely wants to exclude anything associated with Drew's spouse's legs, right? Does he apply for disability with that huge exclusion or not?

• 52:20Speaker 05

  That's a really tough decision to make because we've had to do that a lot for clients where they have something in their past that we have to decide whether we exclude or not. And maybe it's something where it's minor and they're like, oh yeah, I, you know, that was something that had happened to me. I'm totally fine. And like, if that comes up, I can continue to work. Like for myself, I sit at a desk all day. I'm not out like painting or something like that, where it's more physical. So I can continue to work if, you know, my foot hurts. You know, it's not comfortable, but if I had to, I can continue to do it. Legs is a big thing. That's like a huge piece. And I think it also depends on what is her job.

• 53:01Speaker 05

  But there's so many other disabilities that could, so if she was someone like myself where she's sitting down all day, but then she gets some sort of autoimmune disease or like any sort of, it could be cancer, something like that, or something in her hands. That is, we are opening up a whole nother can of worms of potential issues that could also stop her from working. So I don't think it's a bad idea to go down the path of still applying, figuring out what the premiums are on that policy that are going to exclude her legs. And you guys need to decide, is this worth it? Or is this taking away some additional savings to pretty much get her and us to be financially independent earlier?

• 53:42Speaker 05

  Which is when we really think that she's going to start to not be able to continue to walk or whatever it is.

• 53:49Speaker 04

  You could see already Drew and hope everybody else stackers, just the number of questions you want to ask. Start with the model, then there's a bunch of questions to ask. And then I think the next thing to do, Anna, I would think is just price it out. Cause you can't get a cost benefit analysis without knowing what the price tag's going to be.

• 54:08Speaker 05

  Hmm. Yeah, definitely get an, an actual quote and offer from the insurance company. I don't necessarily, and I don't know about you, Joe, but I don't think shopping around is going to be the answer. You might get a little bit of a discount, but I don't think you're going to find any company that's not going to exclude it.

• 54:24Speaker 04

  Yeah, good point. I think once you decide to do it, shop it around. Once you're okay with the exclusion, then shop it around. But yeah, I'm with you. Nobody's going to insure her legs.

• 54:34Speaker 05

  Yeah. I mean, you're even lucky that like they're offering a insurance policy at this point too. So I wouldn't try to find someone who's going to do that. The only option too, not the only option, the other option is if she gets more serious about going from self-employment to working at like a larger corporation that's going to offer some sort of disability insurance. That's really powerful too. So finding out the benefits guide, I know he mentioned that finding out the benefits guide before you accept anything and seeing if that is something that they put in place for all of their employees.

• 55:13Speaker 04

  Oh, a group policy might, might be the answer. Yeah. Great. I hope that helped Drew. And I hope for all of you stackers, just learning a little bit about insurance and how that works. And self-insurance definitely can be part of the plan. The cool thing about this, a lot of us think about what would happen, Anna, but the part that I liked about where you started was what's the crater it causes? Here's the thing that's interesting was that we had disability policy, Cheryl and I, until about four years ago. And then when we were redoing our financial plan, we realized that even if one of us were disabled, we were good. Like we were, we were fine. So even though it would still create a crater, we could survive that crater in other ways.

• 55:57Speaker 04

  So we were able to get rid of these premiums that we were paying, which was, which is pretty awesome. And that's why I like starting there. Cause often we think about the cost of insurance, but we don't think about, what do I actually?

• 56:10Speaker 05

  What do I need it for?

• 56:11Speaker 04

  Yeah. Yeah. Yeah. Good stuff there. All right. Time for us to mosey out onto the back porch. Doug?

• 56:19Speaker 03

  I got a call from MJ and his son, but I think probably you're better to handle this. So I'm going to pass this one over to you guys.

• 56:31Speaker 04

  Hey Joe and team, appreciate the show.

• 56:33Speaker 02

  Love everything you guys give us. Question for you. My son in his mid twenties is in the army. Do you have any special recommendations, websites, authors, books, past episodes of your show, or other advice for military members getting started on their savings journey? Thank you.

• 56:54Speaker 04

  MJ, what a great call. Thank you so much for the call and thank you to your son for his service. Let me give you a couple of great episodes in the past. And a couple of these will lead to books and we'll also ask Anna here about her best advice for people just starting off, whether they're in the military or not. And frankly, none of this has to do with him being in the military. I'll give you a different resource for the military, but Beth Kobliner, who was on two different presidents councils for financial education, is just such a badass when it comes to money. She was episode 1841. It is the money basics that still work 30 years later. That's the, that's

• 57:35Speaker 04

  the title of the episode. She goes through all the things you gotta know when you start out. I thought it was a great interview. Beth is amazing. And even her book, Get a Financial Life, which just was re had its 30 year dust off and reprint is also a good resource. I like that book as well as A Simple Path to Wealth, I think is another great book. Our friend JL Collins wrote A Simple Path to Wealth. You know, he wrote that book for his daughter and all of the things that people, when they start off, they worry about like, what stock to invest in? Who cares? JL Collins is like, just invest in the entire stock market index when you start out. The important part is to focus on more savings like that. That is, is a really good one. So I like that.

• 58:20Speaker 04

  I also like, OG and I have on episode 1888, Your Financial Order of Operations, What to Fix First? Like, what do you do first, second, third, when it comes to your financial plan? And I think that's an important one for people when they start out because often people see all this stuff. You know, what should we, what should we have known when we were 20 years old that we don't know? With all of this, you know, huge amount of information that's out there. So the Financial Order of Operations 1888, and then I'll go back to 1830, which was when Paula Pant was with us for our first time at Texas A&M, Texercana. This was advice directly to people your son's

• 59:01Speaker 04

  age. And it was, the episode's called The Best Money Advice We Wish We Knew at 20. Now, when it comes to military specific stuff, my favorite resource there is my friend, Lacey Langford, has a great show, a great podcast. She's been a guest here a number of times. She's not only a great financial coach, but she actually coaches people that work with military people. Her show's called The Milmo Show. And just looking at Lacey's recent shows, how financial independence gives you more career options, you know, when he leaves the military, he's going to be looking at career options. A lot of people struggle with that when they leave. How to make smarter money decisions.

• 59:42Speaker 04

  What kids need to know about money before adulthood. And then how an army veteran became a Chick-fil-A operator. That's an interesting kind of case study of moving over to being a franchisee of a major franchise. Pretty amazing to run a Chick-fil-A. I don't know if you know, Anna, you know how much money those people make?

• 1:00:00Speaker 05

  I don't know, but that would be really fun.

• 1:00:02Speaker 04

  We recently-

• 1:00:03Speaker 05

  It wouldn't even be about the money for me.

• 1:00:07Speaker 04

  I know. I would have three of those shakes every day.

• 1:00:11Speaker 05

  Me too.

• 1:00:11Speaker 04

  Doug, what's a Jim Gaffigan joke? I think I'm lactose intolerant.

• 1:00:15Speaker 03

  Drinking gravy?

• 1:00:16Speaker 04

  I think I'm lactose intolerant because I've had three milkshakes today and I feel like

• 1:00:22Speaker 05

  Did you try their chicken and waffles yet?

• 1:00:24Speaker 04

  No, but those little chicken mini, the breakfast mini biscuits. Oh my goodness. But we recently, this summer, had an episode about how franchising works. And our guest on that show shared with me that they make between 750,000 and 1.2 million dollars. And Chick-fil-A won't let you own, in most cases, they won't let you own more than one. And they do a bunch of the work that normally you have to do yourself. Like, if you're somebody with, what's the hot franchise now? Seven Brew? If you're somebody who's making a Seven Brew franchise, you have to, you know, get the building permit, you've got to go through and like, they, they help you do it, but you've got to build the facility. Chick-fil-A actually finds the land, builds your facility for you. You're pretty much a high-priced manager of your Chick-fil-A with

• 1:01:09Speaker 04

  all the training that they give you. So-

• 1:01:11Speaker 03

  And you're working on the floor.

• 1:01:13Speaker 04

  You are working-

• 1:01:13Speaker 03

  Almost every day.

• 1:01:14Speaker 04

  Yes. Yes. You are pretty much just a super high-paid manager. Imagine you're managing one Chick-fil-A making a million dollars a year.

• 1:01:21Speaker 05

  That's crazy. Okay.

• 1:01:23Speaker 04

  It's pretty good work.

• 1:01:23Speaker 05

  I quit my job.

• 1:01:24Speaker 04

  Yeah. But Lacey Langford, The Milmo Show is a great one. So those are the three episodes of ours I'd start with. And then I'd listen to Lacey and I think that's a great place to start because the cool thing is Lacey has a lot of government-related and military-related guests on her show. So curating who those people are, I think starts with Lacey and you can go down from there. 20-year-olds, Anna, what's the first thing that you wish you knew at 20 that would have saved you some time and energy?

• 1:01:54Speaker 03

  How about, don't trust the guy with the Trans Am.

• 1:01:58Speaker 05

  Doug, I don't even know what that means. Is that a car?

• 1:02:03Speaker 04

  That is too old a reference, Doug.

• 1:02:05Speaker 05

  You know, Joe, I think what I wish I knew when I was just starting out and, and deciding like, how to get into investing and all that, using your retirement accounts and using a Roth, whatever it is that you have access to is really important. And just even if you can only do a hundred dollars a month, or if it's $50 a month, whatever it is, throw that into that account. Invest it. Just get used to like, what that's going to feel like on your budget. And then also what it's going to look like to actually invest it. It's a really good exercise with a small amount of money. It's not going to make or break you, but it could, it could make an impact long-term, mostly on like, how you're, you're the exercise of it, not necessarily just the

• 1:02:49Speaker 05

  actual money at the end of it.

• 1:02:52Speaker 04

  Yeah. If I had learned that one trick, Anna, it just frankly, thinking long-term, like, I thought, I'll deal with long-term later. I got all these short-term problems. Guess what? I'm 58 years old. I still have short-term problems. Like, the short-term problems never go away. You have to at some point, switch your thinking to do long-term first.

• 1:03:09Speaker 05

  You gotta balance it out. Yep.

• 1:03:11Speaker 04

  Thank you for the call, MJ and Drew. If you've got a call for us, stackingbenjamins.com/voicemail. Thanks to all of you for spending your time with Anna and Doug and I today. If you know somebody that has student loans, maybe you pass along this episode to them. If you know somebody over 65, and they don't realize that the clock's ticking at the end of the year, they might be able to move over $47,500 to a Roth. That's a potentially a big number. Few reasons not to do it, but a lot of reasons to do it if you're eligible. Also, if you know people struggling with disability benefits, great one to pass on to them. But thank you for spending this hour with us. We got another great show on Wednesday. Dr. Corinne Low is with

• 1:03:55Speaker 04

  us. I got to tell you, just knowing a little bit about her background as a Wharton professor, and about the way she looks at negotiation, we're going to talk about, a lot of us are solving for more Benjamins. She asks the deeper question, what do we want that money for? Which is, Anna, what you ask all the time. Like, what are we actually saving all this money for? Corinne Low is going to get at that with us on Wednesday.

• 1:04:18Speaker 05

  I love that.

• 1:04:19Speaker 04

  All right, Doug, you've got it from here, man. What are the three most important things that should be on our to-do list today?

• 1:04:25Speaker 03

  Well, Joe, first, take some advice from Anna and you. Want a 1% interest rate reduction on your student loans, or want to save $47,500 on your Roth conversion? Get moving now. This year will be over before you blink. Second, disability coverage? Think holistically and like the insurance company. If you can cover it yourself, do it. Just don't include this money elsewhere in your financial plan until the risk is gone. But today's big lesson? Well, mine was that I just learned that Vander Holyfield's birthday is the same birthday as our very own Paula Pant.

• 1:05:03Speaker 04

  Wow.

• 1:05:03Speaker 03

  By the way, yeah, she also has a wicked right cross. Pro tip, don't try to steal a beer out of her fridge. Happy birthday, Paula. How about that? Two champions with birthdays today. Thanks to Anna Alum for joining us today. Looking for good financial planning help? Well, assuming she doesn't quit to go manage a Chick-fil-A, you can find Anna's calendar at stackingbenjamins.com/OG. And request Anna, but do it fast. She'd love to help you make better money decisions, or chicken and waffles. Either way, she's who you should call.

• 1:05:39Speaker 05

  It's my pleasure regardless.

• 1:05:44Speaker 03

  This show is the property of SB Podcast LLC, copyright 2026, and is created by Joe Saul Sehi. You'll find out about our awesome team at stackingbenjamins.com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. And oh yeah, before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug, and we'll see you next time, back here at the Stacking Benjamin Show.

• 1:06:33Speaker 04

  It's incredible at a small company like Stacking Benjamins, how one, one hire makes all the difference in the world. If you're a small business, the right hire can be make or break. Hoping the right people see your job posting isn't the best growth strategy. When the pressure's on, you need the right hire. This is a job for sponsored jobs. Indeed sponsored jobs is a boost whenever you need to find quality talent. When workplace chaos hits and you need the right hire, this is a job for sponsored jobs. Hiring Indeed is all you need. Stop struggling to get your job post even seen at other sites. Get matched with and hire quality candidates who can drive the results you need. Reach candidates that meet your specific criteria like skills,

• 1:07:17Speaker 04

  certifications, or locations. Sponsored jobs boost your job post on search results. So you can reach the people that can help your business thrive. Plus with Indeed sponsored jobs, you only pay for results. People are finding quality hires on Indeed right now. In the minute I've been talking to you, listen to this. Companies like yours have made 27 hires on Indeed, according to Indeed data worldwide. And sponsored jobs posted directly on Indeed are 95% more likely to report a hire than non-sponsored jobs. So spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results. When you need the right person to cut through the chaos, that's a job for Indeed sponsored jobs. And guess what?

• 1:08:01Speaker 04

  Our stackers are going to get a $75 sponsored job credit. That's you to help get your job the premium status it deserves at indeed.com/podcast. Just go to indeed.com/podcast right now and support Stacking Benjamins by saying you heard about Indeed in mom's basement. Indeed.com/podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs.

• 1:09:17Speaker 04

  So here's a question, Anna and Doug. How rich are you? You remember we had Nick Maggiulli back on and he did that research about different amounts of money? And Anna, the research was if you go to 0.1%, you make those decisions like flippantly. Like if you've got $100,000, you don't think about $100 decisions anymore. You're just like, if it's $100 or less, you just do it. You don't price shop. You go, whatever. And when you get to a million dollars, if it's a thousand bucks, you're like, yeah, you know, it's a thousand bucks. I'm not price shopping. I'm just doing it. Can you describe how rich you are by how you order food at a restaurant?

• 1:09:55Speaker 05

  Yes. I think you can.

• 1:09:59Speaker 04

  No. Comedian, one of my favorite comedians, Greg Warren, Ken. Listen to how rich Greg is.

• 1:10:06Speaker 06

  I had a problem at the Red Lobster the other day. It was serious. I mean, here's what happened. My waitress thought that I was poor. I'm not, okay? I'm not. I'm not rich. I'm not going to stand up here and brag to you guys about how much money I make. But let's just say I can walk into a Red Lobster and get whatever. Okay. I'm making that kind of cash. Like I'm pulling that down. I'm not saying every day, but I'm saying two, three times a month, I can walk in there and I'm not looking at the prices. Okay. And, and not just during Lobster Fest. I'm saying on a regular Tuesday, I'm doing fine. And I was wearing like my third best shirt. This is six. I didn't look poor. Here's what happened.

• 1:10:48Speaker 06

  I go, I'll take the trout and I want some asparagus. She goes, oh, sir, asparagus is a premium side. I was like, what does that mean? It's real good? She goes, no, it's extra. I was like, how much? She goes, $1.29. I was like, I can swing it. I mean, I mean, I'm going to have to call my guy, you know, we're going to have to move some stuff around. Probably put off retirement for a couple of years, but I want the asparagus. Matter of fact, I want three asparaguses or three, three asparagus guys. What I'm trying to say is I can spare a guy. Okay. I got plenty of guy.