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 point
- Why one point off a rate is a bigger win than it sounds
- What to check first if your repayment plan changed without you doing anything
- A simple way to show a student what a college choice will cost after graduation, using real salary data
- The question one family asked a kid before agreeing to the pricier school
- Why a year-end Roth conversion deserves a look from some savers, and the Medicare premium surprise to understand before you try it
- What an insurer does when a condition is already on your record, and why shopping around won’t change it
- How to map the “crater” a lost income would leave, and when that math says you can skip the policy
- The employer route that can quietly solve a coverage problem
- Which of three famous Black Mondays hit hardest, and when a mutual fund trade really happens
- A starting point for someone new to saving, military families included, that begins small
Why 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
Ask a question for the showEnjoy!
Education Department Extends 1% Student Loan Auto-Pay Cut: The College Investor on the extended deadline
Stacking Benjamins Guides: HR and benefits, college planning, and taxes
Occupational Outlook Handbook: Bureau of Labor Statistics salary and job data for comparing majors
The MILMO Show: Lacey Langford’s podcast on money for military families
Get a Financial Life by Beth Kobliner and The Simple Path to Wealth by JL Collins: the two books recommended for new savers
Our Headline
- Student loan overhaul starts July 1: What borrowers should know (Yahoo! Finance)
Doug’s Trivia
Which Black Monday delivered the largest single-day percentage decline in the Dow Jones Industrial Average?
- A. Black Monday during the 1929 stock market crash
- B. Black Monday, October 19, 1987
- C. One of the Black Monday sell-offs during the 2020 COVID crash
Have a question for the show?
Want more than just the show notes? How about our newsletter with STACKS of related, deeper links?
- 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
- Occupational Outlook Handbook – US Bureau of Labor Statistics
- Glassdoor | Job Search and Career Community
- Beth Kobliner on the Money Basics That Still Work 30 Years Later (and the New Traps Nobody Warned You About)SB1841 | Stacking Benjamins
- Your Financial Order of Operations: What to Fix First (SB1888) | Stacking Benjamins
- The Best Money Advice We Wish We Knew at 20 (Live from Texas A&M – Texarkana) SB1830 | Stacking Benjamins
- Get a Financial Life
- The Simple Path to Wealth: Your Road Map to Financial Independence and a Rich, Free Life
- MILMO Show – Podcast – Apple Podcasts
Join Us Wednesday
Tune in on Wednesday, when we welcome Wharton professor and economist Dr. Corinne Low to explore how to build a bigger stack of Benjamins while creating a better life, a more rewarding career, and a clearer sense of what we’re working toward.
Written by: Kevin Bailey
Miss our last show? Listen here: How to Build a Career You Won’t Regret (Before You Climb the Wrong Ladder) (SB1911) | Stacking Benjamins
Episode transcript
[00:00:00] opener: 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 Vacation’s Over
[00:00:22] Doug: Joe’s mom’s basement, it’s The Stacking Benjamins Show
[00:00:36] Doug: 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, five 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?
[00:01:04] Doug: 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. Just to
[00:01:17] Joe: put the Andrew in there, the third.
[00:01:20] Doug: Right. Who went to the Citadel.
[00:01:22] Joe: Esquire.
[00:01:23] Doug: Yeah. Here’s Joe and Anna, L-L-L-L-L-O-
[00:01:31] Joe: 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- Nice … Anna Ellem with us. How are you? So good
[00:01:45] Doug: for us.
[00:01:46] Anna: I’m good, Joe. How are you?
[00:01:48] Joe: Well, I’m great now that you’re here, because we’re gonna have not just a fun day today, but you’re here all week.
[00:01:54] Joe: You’re here on Wednesday as well.
[00:01:56] Anna: All week long. Yeah, Josh is taking some time off, so I’m coming in.
[00:02:01] Joe: It’s gonna 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.
[00:02:12] Joe: I… 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, uh, 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.
[00:02:36] Joe: And my goodness, we got even more than that. So you ready to cover some big-time ground today, Anna?
[00:02:43] Anna: Let’s hit it.
[00:02:44] Joe: All right. We are gonna hit the ground running quickly, but we’ve got a couple of sponsors who help us keep on keeping on. We’re gonna 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.
[00:02:58] Joe: 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, cancels 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 wanna spend time managing your money.
[00:03:14] Joe: You wanna 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 stackybenjamins.com/fieldkit.
[00:03:30] Joe: 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.
[00:03:53] Joe: What’s up with student loans this year? There’s, there’s a lot up with student loans this year, isn’t there?
[00:03:57] Anna: There’s a lot going on with student loans. It’s h- it’s kinda 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.
[00:04:11] Anna: So some of the 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.
[00:04:19] Joe: 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.
[00:04:28] Joe: Mm-hmm. And then all of a sudden, we wake up and we’re like, “Oh, it was due yesterday .” Like I-
[00:04:33] Anna: Yeah … I need to do
[00:04:33] Joe: this
[00:04:34] Anna: before. 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.”
[00:04:45] Anna: 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 gonna be put in place for anyone who does the auto-enroll before the end of the year.
[00:05:06] Joe: When it comes to choosing a plan, for most people, Anna, that day 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 gonna try to help you interpret it, Stackers. You had 90 days, and for most people, that 90 days is already up.
[00:05:29] Joe: 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 days left to choose what plan you went into, but if not, you went into one of two plans. 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.
[00:06:00] Joe: 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.
[00:06:09] Anna: Yeah, figure out what your payment is gonna be and just an understanding of generally what you’re gonna be looking at for potentially the next 10 years
[00:06:19] Joe: Your servicer’s notice will give you your exact deadline.
[00:06:22] Joe: So if you were in the SAVE plan, you wanna 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.
[00:06:42] Joe: Anna, how does that work?
[00:06:44] Anna: Actually, this was already kind of a program in place where if you were auto-enrolled, you got a quarter of a percentage off. Um, 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.
[00:07:04] Anna: So every month it’s just automatically gonna take those payments out. If you get that set up, you get that discount, which is really, really nice.
[00:07:12] Joe: 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.
[00:07:22] Joe: That’s not a small amount of money.
[00:07:24] Anna: 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 wanna 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.”
[00:07:39] Anna: Like, it’s gonna be the same payment every single month, unless you’re in some sort of variable interest rate. Um, so you should be expecting that every single month, and it should be on high priority to get that debt paid monthly.
[00:07:51] Joe: 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.
[00:08:00] Joe: I was like, “If I can stop making payments, that’s great.” Not even realize these were unsubsidized loans, which meant that the interest kept accruing. I was just… I, 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.
[00:08:14] Anna: Yeah. Absolutely.
[00:08:15] Anna: It’s really important, and you should just automatically be taking advantage of this interest rate reduction if you can.
[00:08:21] Joe: 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.
[00:08:35] Joe: But if your loan rate was 7% and now it’s 6%, you just saved one-seventh. Not… You didn’t save 1%, you saved one-seventh of, of the total interest you were paying, like cha-ching. Yeah. It’s a much, much, much bigger number when you think about it that way.
[00:08:52] Anna: Yeah, and that monthly payment will be less then, so it’s just all around a good decision if you can do that.
[00:08:58] Anna: And again, like e- like I said, even if you couldn’t get the interest rate, you should be signing up for this regardless.
[00:09:03] Joe: 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.
[00:09:14] Joe: 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?
[00:09:25] Anna: Yeah. That’s a really good question. I mean, it’s, it’s gonna 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?
[00:09:41] Anna: What are you looking to do after school? Is it gonna be easy for you to pay those student loans off? Um, so there’s a lot of different conversations around this in terms of- Oh, so
[00:09:52] Joe: it, it, it… I’m sorry, but in other words, what’s the ROI on the debt?
[00:09:55] Anna: Yeah. I mean, college is still a life experience, and if you wanna go there and it, one college is really important for you because not only are you coming out and you’re gonna 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.
[00:10:16] Anna: And how much debt are we talking, too? Because-
[00:10:18] opener: Yeah …
[00:10:19] Anna: that’s huge. It’s good to, for kids to understand, like, what that’s going to look like when they graduate, ’cause that’s gonna be a huge wake-up call. They get into the workforce and if, especially if they’re moving out and they’re not gonna live at home anymore, and they have these giant student loan payments that they’re now obligated to pay for another 10 years.
[00:10:38] Anna: 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.
[00:10:48] Joe: It’s funny, I had a family member I was talking with about this, and, uh, the family member I vehemently disagreed with because he said, “My job is to be a cheerleader for my kids, and if they wanna do it, like, go do it.
[00:10:59] Joe: Go do it.” And I, I thought, well, yes, like, you can do anything you want, but also knowing what the trade-off is gonna be, right? I mean- I mean, it’s- … there is a trade-off. Maybe, do you like the idea of predicting what the debt’s gonna be and showing them what the monthly payment’s gonna be even before they go to college?
[00:11:16] Anna: 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’s probably what your salary is gonna be when you come out of college if you’re gonna graduate with an accounting degree,” or whatever the degree
[00:11:30] Joe: is.
[00:11:30] Joe: And you can get that, you can get that, by the way, from a place like Glassdoor or the Bureau- Mm-hmm … 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.
[00:11:43] Anna: 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.
[00:11:51] Anna: Be the cheerleader for your kid, and don’t let them worry about what college is gonna 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 gonna impact them.
[00:12:06] Anna: ‘Cause maybe the kid is gonna say, “Hey, actually, it’s more important for me to be able to go live in New York City or in a, 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, 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.
[00:12:36] Anna: So having that conversation is very important for a parent.
[00:12:40] Joe: Both of my kids, we went through this with, and at different stages, Anna. W- and 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.
[00:12:59] Joe: What we did for Nick, because as a family we could afford both schools, uh, 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 gonna cost, and Carnegie Mellon, being a fantastic private university, was I don’t remember the number, but, but f- four or 5X, right?
[00:13:29] Joe: The double… Yeah, yeah. 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 gonna have things that go on on campus, you’re gonna have these people that you’re going to interface with. You’re gonna have these opportunities that maybe you don’t get at another campus.
[00:13:47] Joe: And I said to Nick, “If you can ar- articulate for me what Carnegie Mellon will do that you will won’t get at the University of Texas, then we should choose Carnegie Mellon.” Mm-hmm. We should easily choose it. And, and I was hoping, by the way, that he would do that, that he would do that research. Now, the good news was- Were you gonna
[00:14:06] Doug: make him create a PowerPoint?
[00:14:08] Joe: Well, yeah. It’s almost like when we were working with Karen Holland almost a year ago, Doug, you know, with her Does It Make Sense score for middle schoolers. I think it’s the same thing. You know- Sure … she has kids, before they say, “Hey, let’s get a puppy,” right? Go through who’s gonna feed it. What’s the cost of care?
[00:14:25] Joe: What’s it gonna be, and do I really want all the stuff that comes with a 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 Does It 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.
[00:14:52] Joe: They don’t, they don’t wanna be shoved into a thing that they, in this case, a college experience, that they haven’t quantified. Mm-hmm. So 100% do the PowerPoint, Doug. 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.
[00:15:11] Joe: And then he decided, he goes, “You know what? I think because I can’t articulate that, I’m gonna 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.
[00:15:28] Doug: I know somebody that, uh, somewhat related to that story, but almost the o- I kinda like your approach.
[00:15:33] Doug: 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 th- these people are very s- financially successful. They more than likely could’ve paid for all of their kids’, you know, four-year degrees.
[00:15:53] Doug: 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 gonna be more cumulatively for four years than what we have saved, it’s on you.” It’s
[00:16:04] Joe: on you.
[00:16:05] Doug: 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.
[00:16:19] Doug: 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 wanna go to it.” Just like Nick might have thought, “Carne- Carnegie Mellon’s an amazing school. I wanna go there- Yeah … 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.
[00:16:40] Doug: And I, I wish this couple would’ve done what you just suggested, which is let’s, let’s go through it and 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.
[00:16:51] Joe: And that wasn’t a trick on my part.
[00:16:52] Doug: No
[00:16:52] Joe: way. I mean, there are definitely things at Carnegie Mellon that, that you can’t get other places.
[00:16:57] Joe: Mm-hmm. I’ve got friends, you know… I grew up just north of Notre Dame, and their alumni network, as you guys may or may not know, is incredibly powerful. Like-
[00:17:05] Doug: Obnoxious football fans? Yeah. Oh, sorry.
[00:17:07] Joe: 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.
[00:17:18] Joe: 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’ve mattered, we would’ve done it. My daughter was a…
[00:17:34] Joe: it was a different thing, but 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- Whoa. One, one- Whoa. I know, right? ‘Cause she also really likes science.
[00:17:52] Joe: 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 gonna make $52,000 a year.
[00:18:12] Joe: 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 gonna be fantastic, but it will consume you, and you’re not gonna make much money.”
[00:18:21] bit: Mm-hmm. “
[00:18:21] Joe: That is just the way… I, I mean, unless you’re some kind of unicorn, it’s gonna be very difficult, and especially when you’re starting out.
[00:18:27] Joe: Like, you’re gonna have to hustle, ’cause there’s low barriers to entry and a lot of people fighting for a limited pie of money. Brain surgery out of college, $320,000, right? And, uh, and you’re still gonna work a lot. It’s gonna be tough. It’s gonna be life-and-death stuff you’re working on, so emotional stuff going on.”
[00:18:45] Joe: Mm-hmm. “But economically, it’s gonna 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- Yeah … with this stuff.”
[00:19:07] Joe: Still be able
[00:19:08] Anna: to get into those skills, yeah.
[00:19:10] Joe: Yes, and that went great until organic chemistry hit. Mm-hmm. And when, and for anybody in the sciences knows, organic chemistry is the great weeder-outer of potential doctors. That’s the weed
[00:19:19] Doug: out class.
[00:19:20] Joe: That’s the one. So then Autumn switched to being a journalism major, but guess what my daughter got?
[00:19:25] Joe: She got hustle. ‘Cause she knew, ’cause 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.”
[00:19:36] Anna: Mm-hmm.
[00:19:36] Joe: Because we went over what it would look like. I think that’s a great thing for any parent to do.
[00:19:39] Anna: I think that’s a great thing. I, I like when parents are, and this is something that I really wanna do for my kids, is like make sure if they come to me and they say that like they wanna be a dance major, whatever, it’s not crushing the dream, but it’s just saying, “Here is what your reality might look like.
[00:19:56] Anna: 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.
[00:20:03] Joe: But there is a reality that we need to face.
[00:20:04] Anna: Yeah.
[00:20:05] Doug: 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, I think it’s really funny.
[00:20:18] bit: Yeah, I, I was lucky enough to have dropped out, um, ‘
[00:20:22] Doug: cause I realized early on that these, these student loans are
[00:20:25] bit: 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, ’cause it’s a bad idea for a business.
[00:20:39] bit: If you had to go to the bank, to the small business desk, and ask, be like, “Yeah, I’m gonna need $150,000,” they’d be like, “All right, what’s your business idea?” “All right, here’s the idea. For the next four years I’m gonna get blackout drunk.” But also, I’m gonna get a degree in sociology
[00:21:03] bit: They’d be like, “Get the out of our bank.”
[00:21:08] Joe: 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 gonna go into debt. If you’re gonna go into debt, there’s gotta be some ROI. And, you know, we just wanna be the people that help you put on a brave face, whether you are applying for colleges or you’re applying for jobs.
[00:21:29] Joe: There’s a lot of rejection out there right now, people. Himesh Patel has written a letter that, uh, maybe we should all get ready so that we can fight off all this adversity that we’re seeing.
[00:21:44] bit: 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
[00:22:04] bit: 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.
[00:22:25] Joe: I’m sorry, I can’t accept the… That’s what we all have to just write that letter from time to time.
[00:22:29] Joe: So
[00:22:29] Doug: good.
[00:22:30] Joe: Yeah, good stuff. All right, let’s, uh, 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.
[00:22:59] Joe: What’s this magic trick all about, Anna?
[00:23:01] Anna: Asterisk, asterisk, asterisk, asterisk.
[00:23:05] Joe: 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?
[00:23:14] Anna: Yeah. My husband and I were just watching some baseball playoffs, and, you know, they’re…
[00:23:18] Anna: it’s just all drug ads- Yes … at that point. And one of them was, you know, the classic, “Don’t take Skyrizi if you are allergic to Skyrizi.” Yeah. It’s just like that. I love that line. 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.
[00:23:37] Joe: Yeah, 47 five.
[00:23:39] Anna: 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 zero dollars 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.
[00:24:04] Anna: 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.
[00:24:17] Joe: 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?
[00:24:28] Joe: I mean, by far the majority of us.
[00:24:30] Anna: 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 a- another path, but, like, make sure that you’re looking into if you qualify for itemized deduction this year be- and, and last year was also part of that.
[00:24:47] Anna: But because of that increase in the SALT deduction, which is built within-
[00:24:52] Doug: There’s a deduction for the strategic arms limitation treaty? Mm-hmm, mm-hmm. That’s,
[00:24:54] Anna: that’s… Well, I was about to- Exactly, Doug
[00:24:57] Joe: Yeah. What is it, Anna? What is a SALT deduction?
[00:24:59] Anna: So SALT deduction is primarily made up of your state and local tax.
[00:25:05] Anna: So if you live in a state where you have to pay state taxes, that’s part of it. Your real estate tax, so 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.
[00:25:27] Anna: And usually they’re, uh, they were previously capped at $10,000. And there are some people, if your income is above, like, 5 or $600,000 a year for a married couple, you’re probably still capped at that 10,000. But there is this, like, sweet spot of high income earners who aren’t above that 5 or 600K, who have a high state tax, who can actually deduct up to $40,000- Oh, there you go
[00:25:53] Anna: within a SALT deduction. There you go. 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 a CPA, if you’re reporting this yourself, just do the exercise to make sure that you can’t itemize this year.
[00:26:17] Anna: Check the box. ‘Cause it might… Yeah, you might fall into that category, and you might not, and then you get a, a good standard deduction too.
[00:26:24] Joe: But if you’re somebody that gets the standard deduction, and you are a married couple 65 plus, these age-based additions that are gonna phase out at the end of this year, part- some of them are gonna phase out at the end of this year, is what creates this magical sweet spot of $47,500 that’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 wanna…
[00:26:54] Joe: Y- you might be eligible for it, it might look good on paper, but there might be a lot of reasons you don’t wanna do this. Mm-hmm. So why would somebody not wanna do this if they’re eligible?
[00:27:02] Anna: 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.
[00:27:14] Anna: I don’t see the reason why you wouldn’t wanna do that. I saw one thing- I mean, if you can move it tax-free.
[00:27:19] Joe: Yeah, I just saw one thing that said that if you have $380,000 or less, you’re gonna be in the lowest tax bracket anyway, so, you know, conversion, eh.
[00:27:31] Anna: But it’s tax-free.
[00:27:33] Joe: But it’s tax-free.
[00:27:34] Anna: It’s tax-free now, so I mean, why wait?
[00:27:37] Anna: I mean, w- that, that conversation comes into play when we’re talking about, oh, this is a taxable event, and we are, we have a, a IRA balance that isn’t astronomical, and we want to convert a large amount. We’re getting into, like, the 22, 24% bracket, and you’re a 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.
[00:28:06] Joe: No, and it’s funny as I think through this, uh, 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 requirement of distributions, ’cause the, the reason why it’s unnecessary, Stackers, is because your standard deduction is gonna wipe out any of the tax that you would’ve paid anyway, so it’s already tax-free.
[00:28:28] Joe: But if it grows between now and 75, and you start taking minimum distributions out at 75, well, then okay, uh, uh, now you will have some tax, so.
[00:28:40] Anna: Also, like, we don’t know what tax brackets are gonna look like when you’re actually 75. That’s 10 years away. Who knows who’s gonna be in office at that time, what tax brackets are gonna look like, if the actual taxable number is gonna increase, like that percentage, if that deduction’s gonna be taken away.
[00:28:55] Anna: So, so much can change. If you have the ability to do this, do it now.
[00:29:00] Joe: I think the big issue is with people earning money for a longer period of time that no other income is gonna be a big piece of it. But what about IRMAA? People also caution you about IRMAA. What is IRMAA, and why should we be wary of this?
[00:29:15] Anna: IRMAA 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 IRMAA 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.
[00:29:44] Anna: If your income jumps during a, 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. They’re gonna add another premium on top of that so that your Medicare premiums are gonna be much higher than just like maybe what you normally would have anticipated
[00:30:08] Joe: I love this idea of getting to know IRMAA ahead of time, which is why I wanted to talk about it, ’cause even if in your- 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 401versus the traditional- Mm-hmm
[00:30:25] Joe: 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, Anna. And he, he’s like- Mm-hmm … “D- do I convert it when I’m at this high tax bracket?”
[00:30:41] Joe: Like, he’s trapped with all this money that’s sitting in traditional accounts.
[00:30:46] Anna: 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.
[00:31:01] Anna: So normally we’re accessing brokerage account reportable income, or taxable income, sorry, becomes much lower. Yeah. 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.
[00:31:31] Anna: 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.
[00:31:46] Joe: It helps you build in so much flexibility if you start planning this well, well, well before 60.
[00:31:53] Joe: And what always made me sad when I was a financial planner was people would walk in, you know, two months before retirement, and y- you know- Mm-hmm … we can do something, but man, if you’d started this at age 30, we could have done so, so, so much more.
[00:32:06] Anna: Yeah.
[00:32:06] Joe: In the second half of today’s discussion, Anna and I are gonna take a question from Drew.
[00:32:10] Joe: Drew’s got a great question about disability coverage. This is such an important coverage. It’s something people don’t wanna talk about, which is exactly why we’re gonna 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.”
[00:32:28] Joe: 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 stackingbenjamins.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.
[00:32:50] Joe: You also get a discount on our guides if you buy two, even bigger discount if you buy all three, so stackingbenjamins.com/guides. All right. Doug, man, you made a big promise, and that’s that today’s trivia’s fantastic. Tell me it’s so.
[00:33:04] Doug: That’s a promise that’s easy to keep, Joe. Hey there, Stackers, I’m heavyweight champion of the cul-de-sac and guy whose left hook once knocked over an entire bowl of queso, Joe’s mom’s neighbor, Doug.
[00:33:15] 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.
[00:33:39] Doug: So today, we’re putting the Black Mondays in the ring. Which one delivered the biggest one-day percentage punch to the Dow? 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?
[00:34:03] Doug: 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.
[00:34:19] Doug: 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 them duke it out.
[00:34:39] Doug: 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.
[00:35:04] Doug: How hard did that Monday hit? The Dow fell nearly 13% in a single day. Oof, that is gonna 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.
[00:35:28] Doug: 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 its 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.
[00:35:50] Doug: 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.
[00:36:18] Doug: 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
[00:36:31] Joe: You know what’s interesting? My, my father-in-law was very open about this. And, uh, on that day in 1987, he took his money out of his funds- Wow … ’cause he thought it was gonna get worse. After the 22% decline, he took his money out. A- and it was a warning to me and to everybody. Like, he told us openly there were two problems.
[00:36:50] Joe: 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’d 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 at any time.
[00:37:09] Joe: You can make the trade at any time. Mutual fund trades happen at 4:00 PM. 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’ve been the same thing.
[00:37:31] Anna: Wow. That’s really sad.
[00:37:33] Joe: Yeah. It was great that he was open about it, though- Mm-hmm … ’cause 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.” C. Hi, and Anna, that is.
[00:37:51] Joe: This is the part of the show where we take, uh, one of your questions, stackers. Head to stackingbenjamins.com/yelldownstairs and we’re happy to answer your question, like this one that comes to us from Stacker Drew. Hey, Drew.
[00:38:10] caller: 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 that there’s gonna be a medical solution to what she’s been experiencing.
[00:38:35] caller: We 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 sh- uh, short-term disability, or if that isn’t an option, if we should look into self-insuring.
[00:38:56] caller: As background, my wife is self-employed, but she’s looking to potentially, uh, get back into the workforce in the future. We have $80,000 in our HSA. We are debt-free aside from our mortgage, uh, which has $130,000 left, and we have a three-month emergency fund. I love the podcast and would appreciate your input here.
[00:39:18] caller: Thanks.
[00:39:20] Joe: Drew, thank you so much for the question, and what an important thing that people don’t wanna talk about, Anna. I, 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.” Mm-hmm. Let’s, let’s, let’s talk about something a lot more fun than this.
[00:39:36] Anna: 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.
[00:39:44] Joe: But the statistics are why you’re doing it, ’cause stat-stat- 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 wanna believe.
[00:39:57] Anna: Yeah. Uh, uh, b- people are a little bit more easy to get on board with a life insurance policy and thinking about, like, their own death, which is interesting, but they’re much more likely- Yeah, ’cause there’s a one in one chance … to experience a disability. Yeah. They’re much more likely to experience a disability than…
[00:40:14] Anna: Or, 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 gonna look like, how it’s gonna feel in your body, what capacity you can continue to work.
[00:40:39] Anna: 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, ’cause 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?
[00:40:59] Joe: 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.
[00:41:08] Joe: Whenever somebody came into my office and they’re like, “Hey, I’m thinking about applying for disability insurance,” I, I was always … And I was always like, “Okay, so what happened?” Mm-hmm. “Oh, well, I hurt my back at work.” Guess what? That event- Too late … 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.
[00:41:31] Anna: Mm-hmm.
[00:41:32] Joe: 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.
[00:41:39] Anna: Yeah. Yeah. Now that it’s on your medical record, there’s no way that they’re not gonna see that, and they’re going to exclude anything. I mean, they might not, they might not even insure you.
[00:41:48] Anna: Right.
[00:41:49] Joe: 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, uh, his spouse with a few years not bringing in any income? Does he… Like, what does he… How does he kind of model that?
[00:42:05] Anna: Yeah, I think it’s running through a plan of w- 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.
[00:42:19] Anna: Understanding then the next part, which is how much do we ri- 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.
[00:42:43] Anna: So understanding that is the first part of this
[00:42:48] Joe: What kind of a crater is there gonna be-
[00:42:50] Anna: Mm-hmm …
[00:42:51] Joe: when she is fully disabled?
[00:42:53] Anna: Yeah. Then what is, what, how do we pivot from there? Is, um, 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 more sitting down, it’s less physical?
[00:43:12] Anna: 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 100% healthy. We have no idea how some sort of disability could take their ability to work away from them.
[00:43:36] bit: Right.
[00:43:36] Anna: Whether it’s mental or physical, w- 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.
[00:43:47] Joe: And I think that is a advantage for Drew and his spouse, which by the way, having a disability already is not an advantage.
[00:43:54] Joe: Mm-hmm. 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 wanna exclude, and once again, we need to think like the insurance company.
[00:44:17] Joe: The insurance company definitely wants to exclude anything associated with Drew spouse’s legs, right? Mm-hmm. Does he apply for disability with that huge exclusion or not?
[00:44:29] Anna: That’s a really tough decision to make, ’cause 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.
[00:44:37] Anna: 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.
[00:44:54] Anna: So I can continue to work if, you know, my foot hurts. You know- Yeah … 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. But there are 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…
[00:45:20] Anna: It could be cancer or something like that, or something in her hands, that i- 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.
[00:45:41] Anna: 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, which is when we really think that she’s gonna start to not be able to continue to walk or whatever it is
[00:45:58] Joe: You could see already, Drew, and hope everybody else, Stackers, just the number of questions you wanna ask.
[00:46:03] Joe: 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- Mm-hmm … you can’t get a cost-benefit analysis without knowing what the price tag’s gonna be.
[00:46:17] Anna: Mm-hmm. Yeah, definitely get a, an, a- an actual quote and offer from the insurance company.
[00:46:22] Anna: I don’t necessarily, and I, I don’t know about you, Joe, but I don’t think shopping around is gonna be the answer. Um, you might t- get a little bit of a discount, but I don’t think you’re gonna find any company that’s not going to exclude it.
[00:46:33] Joe: Yeah, good point. I think once you decide to do it, shop it around.
[00:46:37] Anna: Mm-hmm.
[00:46:37] Joe: Once you’re okay with the exclusion, then shop it around. But yeah, I’m with you. Nobody’s going to insure her legs.
[00:46:43] Anna: 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 gonna do that. The only option, too, or 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.
[00:47:08] Anna: Hmm. That’s really powerful, too.
[00:47:10] Joe: Oh.
[00:47:11] Anna: 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.
[00:47:22] Joe: Oh, a group policy- Mm-hmm … 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.
[00:47:36] Joe: The cool thing about this, a lot of us think about what would happen, Anna, but the part that, that I liked about where you started was what’s the crater it causes? Here’s the thing that’s interesting, was that, uh, we had disability policies, Cheryl and I, until, uh, 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.
[00:47:58] Joe: Like, we were- Mm-hmm … we were fine. So even though it would still create a crater, w- we could survive that crater in other ways, so we were able to get rid of these premiums that we were paying, which was- Mm-hmm … which was 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 w- what do I actually, what do I actually gonna do?
[00:48:19] Joe: What do I need it for? Right. Yeah. Yeah, yeah. Good stuff there. All right. Time for us to mosey out onto the back porch. Doug?
[00:48:28] Doug: I got a call from MJ and his son, but I think probably you’re better to handle this, so I’m gonna pass this one over to you guys.
[00:48:39] opener: Hey, Joe and team. Uh, appreciate the show. Love everything you guys give us. Question for you, my son in his mid-20s is in the Army. Uh, 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?
[00:49:01] opener: Thank you.
[00:49:02] Joe: 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.
[00:49:21] Joe: 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, uh, 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.
[00:49:43] Joe: That’s the, that’s 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.
[00:50:07] Joe: 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, the important part is to focus on more savings.
[00:50:25] Joe: Like, that, that is, is a really good one. So I like that. 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.
[00:50:46] Joe: 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, Texarkana.
[00:51:07] Joe: This was advice directly to people your son’s age, and it w- 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.
[00:51:27] Joe: 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, and just looking at Lacey’s recent shows, how financial independence gives you more career options. You know, when you leave the military, you’re gonna be looking at career options.
[00:51:46] Joe: A lot of people struggle with that when they leave. How to make smarter money decisions, uh, 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.
[00:52:04] Joe: Pretty amazing to run a Chick-fil-A. I don’t know if you know, Anna, do you know how much money those people make?
[00:52:09] Anna: I don’t know, but that would be really fun.
[00:52:11] Joe: We recently did- It
[00:52:12] Anna: wouldn’t even be about the money for me.
[00:52:16] Joe: I know. I would have three of those shakes every day.
[00:52:19] Anna: Me too.
[00:52:20] Joe: Doug, what’s that Jim Gaffigan joke?
[00:52:22] Joe: I think I’m lactose intolerant. Are you drinking
[00:52:24] Doug: gravy?
[00:52:24] Joe: I, I think I’m lactose intolerant because I’ve had- Oh … three milkshakes today and I feel like .
[00:52:30] Anna: Did you try their chicken and waffles yet?
[00:52:32] Joe: No, but those little chicken mini, the breakfast mini- Mm-hmm … biscuits, oh my goodness.
[00:52:37] Anna: Same.
[00:52:38] Joe: 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.
[00:52:50] Joe: 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? 7 Brew? If you’re somebody who’s making a 7 Brew franchise, you have to, you know, get the building permit, you’ve gotta go through and, it, like, they, they help you do it, but you’ve gotta build the facility.
[00:53:11] Joe: 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 all the training that they give you. So- And
[00:53:20] Doug: you’re working on the floor-
[00:53:22] Joe: You are working …
[00:53:22] Doug: almost every day.
[00:53:23] Joe: Yes. Yes, you are pretty much just a super high-paid manager.
[00:53:26] Joe: Imagine you’re managing one Chick-fil-A making a million dollars a year.
[00:53:30] Anna: That’s crazy. Okay
[00:53:31] Joe: It’s a pretty good one I’m gonna quit my
[00:53:32] Anna: job.
[00:53:33] Joe: Yeah. But Lacey Langford, uh, The Millmo 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, uh, that’s a great place to start.
[00:53:42] Joe: Because the cool thing is Lacey has a lot of, uh, government-related and, uh, 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’ve saved you some time and energy?
[00:54:03] Doug: How about don’t trust the guy with the Trans Am?
[00:54:07] Anna: Doug, I don’t even know what that means.
[00:54:10] Joe: If he… Yeah.
[00:54:11] Anna: Is that a car?
[00:54:12] Joe: That is too old a reference, Doug.
[00:54:14] Anna: Yeah. Okay.
[00:54:14] Joe: Yes, yes. I
[00:54:15] Anna: met my husband- With
[00:54:16] Doug: the Camaro.
[00:54:17] Joe: Yes. That would be like saying if he asks you if you want to see his record collection, he really doesn’t want to show you his record collection.
[00:54:28] Anna: 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, um, using a Roth, whatever it is that you have access to, is really important. And just even if you can only do $100 a month or if it’s $50 a month, whatever it is, throw that into that account.
[00:54:52] Anna: Invest it. Just get used to, like, what that’s gonna feel like on your budget, and then also what it’s going to look like to actually invest it. Um, it’s a really good exercise with a small amount of money. It’s not gonna make or break you, but it could, it could make an impact long term, mostly on, like, how you’re, you’re…
[00:55:09] Anna: the exercise of it, not necessarily just the actual money at the end of it.
[00:55:14] Joe: 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.” Mm-hmm. Guess what? I’m 58 years old. I still have short-term problems.
[00:55:26] Joe: Like, the short-term- Yeah … problems never go away. You have to, at some point, switch your thinking to do long-term first. You gotta
[00:55:31] Anna: balance it out, yep.
[00:55:34] Joe: 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.
[00:55:45] Joe: If you know somebody that has student loans, maybe you pass along this episode to them. If you s- 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. And that, 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.
[00:56:05] Joe: 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 Lowe is with us. I gotta tell you, just knowing a little bit about her background as a Wharton professor, and about the way she looks at negotiation, we’re gonna talk about…
[00:56:26] Joe: A lot of us are solving for more Benjamins. She asked the deeper question, “What do we want that money for?” Which is, Anna, what you ask all the time. Mm-hmm. Like, what are we actually saving all this money for? Corinne Lowe is gonna get at that with us on Wednesday. I
[00:56:40] Anna: love that.
[00:56:41] Joe: All right, Doug, you’ve got it from here, man.
[00:56:43] Joe: What are the three most important things that should be on our to-do list today?
[00:56:47] Doug: Well, Joe, first, take some advice from Anna and you. Want a 1% interest rate reduction on your student loans, or wanna save $47,500 on your Roth conversion? Get moving now. This year will be over before you blink. Second, disability coverage?
[00:57:06] Doug: 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 Evander Holyfield’s birthday is the same birthday as our very own Paula Pant.
[00:57:25] Joe: Wow.
[00:57:25] Doug: Who, by the way, yeah, she also has a wicked right cross. Pro tip: don’t try to steal a beer out of her fridge. No. Happy birthday, Paula. How about that? Two champions with birthdays today. Thanks to Anna Alam for joining us today. Looking for good financial planning help? Well, assuming she doesn’t quit to go manage a Chick-fil-A-
[00:57:47] Doug: 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.
[00:58:01] Anna: It’s my pleasure, regardless.
[00:58:07] Doug: This show is the property of SP Podcast LLC, copyright 2026, and is created by Joe Saul-Sehy.
[00:58:14] Doug: 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.
[00:58:33] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s mom’s neighbor, Doug, and we’ll see you next time back here at the Stacking Benjamins show
[00:59:41] Joe: 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.
[01:00:01] Joe: 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 1,000 bucks, you’re like, “Yeah, uh, you know, it’s 1,000 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?
[01:00:19] Anna: Yes. I think you can.
[01:00:23] Joe: No. Well g- g- comedian, one of my favorite comedians, Greg Warren can. Listen to how rich Greg is.
[01:00:30] caller: 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, but I’m not gonna stand up here and brag, you guys, about how much money I make.
[01:00:44] caller: But let’s just say I can walk into a Red Lobster and get whatever, okay? Like… I’m making that kind of cash. Like, I’m pulling that down. I’m, 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.
[01:01:06] caller: And I was wearing, like, my third-best shirt. This is six. I, I didn’t look poor. Here’s what happened. I, I go, uh, “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, “A dollar 29.”
[01:01:29] caller: I was like, “I can swing it. I mean- … I mean, I’m gonna have to call my guy, you know?” “We’re, we’re gonna have to move some stuff around. You know, probably put off retirement for a couple years, but I, I, I want the asparagus. Matter of fact, I want three asparaguses or three, three asparaguis. What I’m trying to say is I can spare a guy, okay?
[01:01:50] caller: I, I, I got plenty of guy.”
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