What happens when you hand the mic to Stackers? You get a mailbag episode loaded with real-life money challenges, surprising lessons, and a few “wait, what?” moments. Joe Saul-Sehy, OG, special guest Anna Allem (a CFP® with her own winding journey into the profession), and Neighbor Doug dig into your most pressing financial questions—no fluff, no jargon, and definitely no shortage of basement-style tangents.
This week’s listener lineup serves up a buffet of topics: how to turn an HSA into a stealth retirement account, whether a Roth conversion is the right move (and when), the tricky little details that make or break a trust, and what’s happening in the ever-shifting world of auto insurance. Along the way, we get into the mental game of money—why positive thinking might be more than motivational fluff—and how planning isn’t just about the plan on paper.
From Anna’s seasoned perspective to OG’s no-nonsense approach and Joe’s knack for cutting through the noise, you’ll walk away with strategies you can actually use. Plus, we can’t resist a detour into AI at the Wendy’s drive-thru (yes, it’s a thing), proving once again that money talk is always better when you leave room for curiosity.
What You’ll Learn This Episode:
- How to decide if a Roth conversion makes sense for your tax picture
- Ways to supercharge an HSA for long-term wealth (and not just medical expenses)
- Trust basics you might be overlooking—and why that could cost you.The latest trends in auto insurance and how they might affect your ratesWhy mindset matters just as much as math in building financial confidence Questions to Ponder (or Argue Over in the Basement)
How do you decide when to update your insurance coverage versus just shopping for a better rate? FULL SHOW NOTES: https://stackingbenjamins.com/questions-from-the-stacker-community-1730
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy!
If you were starting an HSA today, how would you use it—medical safety net or stealth retirement account?
Have you considered a Roth conversion? What’s the one factor holding you back?
When it comes to trusts, do you prefer to keep heirs in the loop or keep plans private until needed?
Our Special Guest: CFP® Anna Allem
Big thanks to Anna Allem for joining us today. To learn more about Anna, as well as the team of advisors that work with OG, visit Financial Advisor | Bannerman Wealth | Who We Are. To find time on Anna’s calendar, visit stackingbenjamins.com/og.
Doug’s Trivia
- What instrument did the chimpanzee use to beat five stock analysts in a stock-picking competition back in 1993, run by a Sweedish newspaper?
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
- 3 Questions You’re Dying To Know about Estate Planning (SB1723)
- Donor Advised Funds 101 (with Adam Nash) (SB1724)
- The Shocking Retirement Hack That Has Nothing to Do With Money (SB1697)
- Learn the Efficient Frontier!
Join us Friday!
Be sure to tune in on Friday when we’re all about unintended consequences in money and work-life systems like credit scores. How do you work around the downsides?
Written by: Kevin Bailey
Miss our last show? Listen here: Unpacking Two Big Ideas: Infinite Banking and Saving For Young Children (SB1729)
Episode transcript
[00:00:00] opener: My plan is sound mathematically sound. It cannot fail. It’s perfect. Three months from now, I will be worth $50,000 independent for life. [00:00:23] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show. [00:00:38] Doug: I am Joe’s mom’s neighbor, Doug, and today the star of the show is you. We are sharing your calls, emails, notes in our Facebook group, and more as we dive into HSAs, trusts, auto insurance, the Efficient Frontier Health and retirement, and whole bunch of stuff I can’t think of. And now here are three people who are buckled in and ready to answer your questions. [00:01:01] Doug: It’s Joe og. And CFP Anna Alo can’t figure out. I was gonna give her the whole Oji g treatment and I couldn’t figure out how to do that. [00:01:13] OG: N’s in a syllable, it’s a lot harder. [00:01:15] Doug: Alum mum. Right? Maybe next time we gotta put Anna at the top. I think it would just sounded like Anna Aluminum if I did that. [00:01:23] Joe: Hey everybody, welcome back to the Stacky Benjamin Show. [00:01:25] Joe: I am Joe Saul Sea. Hi, average Joe Money on X Twitter, whatever it, uh, you might call it these days. And the guy who these days and every day we call OG on the show is sitting across from me. Mr. OGs here. How are you, brother? [00:01:39] OG: Oh, I’m just happy to be here. It’s the middle of the week. It’s a middle of a short week, so it’s, it’s even better. [00:01:44] Joe: You know what I dislike about Labor Day Week is you get to Friday and you’re like, wow, that was great. But then the following Wednesday, like, are you kidding me? I still have two days left of this. Like, I have to work all five days. How tough is that? [00:01:59] OG: Tough for a guy like you [00:02:00] Joe: fi find. We’ll find a way to get through it. [00:02:02] Joe: Of course, next week I go to Portland, so I get to work exactly one day next week, which is, uh, not too tough. Woohoo. [00:02:08] OG: How are you [00:02:09] Joe: gonna [00:02:09] OG: handle it? [00:02:09] Joe: The person who’s going to hopefully do all the work, OG on this show is a woman who you have the pleasure of working with and alum joins us. How are you? [00:02:19] Anna: Hey everyone. [00:02:21] Anna: I’m good, thanks. Well, [00:02:22] Joe: welcome to the party, Anna. Your life must be a party ’cause you get to work with OG every freaking day. [00:02:29] Anna: Yeah, I talk to him Monday through Friday. Oh, it’s a blessing. Yeah. Pinch me. [00:02:34] Doug: Look how forced that smile looks. [00:02:39] Doug: Why holding up that sign that paycheck Depends on it. Say nice things or else [00:02:46] Joe: it’s like that my boss told a funny joke. Laugh, right. Uh, it’s great. The golf clap. Wait, yeah, I’ve heard that laugh before. So Anna, what’s your favorite part of being a CFP? [00:02:57] Anna: My favorite part of being a CFP, I didn’t expect that to be the first question. [00:03:01] Anna: It’s really fun working with people. Recently I transitioned from associate advisor where I was working more under Josh and another advisor, and then transitioned into being lead advisor. And it’s super fun being able to talk to clients, give them advice, and just become kind of friends with them. Yeah, I really enjoy that. [00:03:22] Anna: It’s, um, super fun every day. I’ve just grown to really, really like it. Growing into this role now. [00:03:29] Joe: That was always my favorite piece. Watching people attain their goals. [00:03:31] Anna: Mm-hmm. And [00:03:32] Joe: knowing that every day you help them get a step closer. I, I don’t know, when you see people’s, uh, able to afford to help their kid buy the first car or you know, somebody getting a house or retiring, like that was super fun. [00:03:46] Joe: But if you had advice for people just breaking into the business. ’cause as you know, this is a hard business, being a financial planner. We get questions all the time from people about being a financial planner. What would your best advice be to somebody who thinks they might wanna be a financial planner? [00:04:00] Anna: I think finding the right people to help guide you in the path. I know, well you still clearly haven’t found that. I know we’re laughing about, about og, but we’re still looking [00:04:10] OG: for that. [00:04:12] Anna: He has been an amazing mentor to me. Obviously he’s my boss too, but. I don’t know if I would be where I am right now as a lead advisor and working with clients without him. [00:04:23] Anna: Oh, Doug, it’s getting deep. Okay. Alright. [00:04:24] Doug: Yeah, let already oh [00:04:27] Joe: and C, tell me more. Don’t stop. Tell me more. Worst, don’t stop guest ever. We’re sorry Anna. Can’t stay. Not at all. We’re super happy you’re here today with us, Anna, to help us answer our stacker questions as if you’re brand new here. We have a phenomenal community and you have asked us a lot of questions. [00:04:46] Joe: If you have a question for us, by the way, head to stacky Benjamins dot com slash voicemail and we’ll answer your question as well. We try to answer at least a couple a week in just a second. Anna and OG and I are gonna dive in, but before that, we’ve got a couple sponsors to help us keep on keeping on so that you don’t have to pay any money for any of this. [00:05:04] Joe: Goodness. So we’re gonna hear from them and then Anna OG and I starting off with a question about Roth conversions. [00:05:18] Joe: Our first question comes from stacker Paul, who is uh, well, he’s ready to do some Roth converting guys. Hey Paul. [00:05:28] caller: Hi, Joe and og. Really grateful for the show. Thank you. You’ve taught me so much. I’m now confident it’s time for a big jump into NFTs. I’m 62 gainfully employed in a semi-retirement job to pass the day and buy some healthcare. [00:05:41] caller: The kids are in college or have successfully fledged the nest. Our family reached our fine numbers some years back with no debt and a portfolio of low cost ETFs mimicking Vanguard target-date funds with a good dose of Paul Merriman’s, small cap value added in, and years of safe cash assets. After three decades of marital bliss, my spouse abruptly decided to become a free agent. [00:06:03] caller: The divorce attorney does has since settled and with the division of wealth, I may be homeless, but I have the substantial chunk in fresh traditional IRA. In my asset column, things break down to about 500,000. In the traditional IRAA comfortable Roth 400 K in a taxable brokerage I bonds and CD ladders. [00:06:20] caller: Tax-wise, I routinely land in the low end of that 22nd percent bracket. Here’s my question, with regard to entering the complex moving parts of Medicare and Social Security taxes in the next three to eight years, what’s the best play for Roth conversions? Should I push the, convert all the traditional IRAs over in the next three years and swallow hard at 24% or draw conversions out in a decade? [00:06:42] caller: Doug, the dad jokes work for me. Keep up the good fight in Carolina. [00:06:47] Joe: Hey Paul, or I’m not even gonna, I can’t even refer to him as he referred to himself, Paul from Caroline. [00:06:54] Doug: Let’s just answer the question. [00:06:56] Joe: You know what I love Paul. I love the fact that you are able to keep your sense of humor through all of this. [00:07:03] Joe: I may be homeless, but, uh, that’s great and to really, um, be positive. You’ve done a great job saving and I think that’s really gonna help you going forward. And it seems like asset allocation wise, you have a lot going on. But let’s talk about this. Uh, Anna and og, he’s got this issue. He’s in the 22% bracket, but he’s looking at coming up additional taxes on Medicare and social Security. [00:07:27] Joe: First of all, I think we gotta break down what is this Roth conversion thing anyway, og, like, what is he trying to do? What’s he trying to accomplish with a Roth conversion for our new stackers? [00:07:38] OG: At the base level, when you contribute money to retirement, you’ve basically picking, do you wanna pay taxes on that today or pay taxes on the future? [00:07:47] OG: For the longest time, especially people that have been, you know, saving money for a long time or been in the workforce for a long time, the default answer was save money before you pay taxes. So your pre-tax 401k or traditional IRA, that sort of thing. It’s been a while since the Roth has been out 25, 20, almost 30 years now. [00:08:05] OG: But in the workplace plan department, Roth 4 0 1 Ks, surprisingly, are still pretty rare. I think everyone has one now, but still, most people don’t participate in the Roth 401k. And I think a lot of that has to do with just inertia. But basically over his career he’s put a bunch of money in pre-tax accounts, so he hasn’t paid taxes on this money at all. [00:08:23] OG: And in exchange for that, as that money sits there and grows and done his, does his thing for 30 years, like he said, he’s not paid a dime of taxes. The trade off is, is that the IRS says eventually you gotta start paying us. You know, you pay taxes when you withdraw the money, and then if you don’t wanna withdraw it, they still make you pay taxes with a minimum schedule of withdrawal starting when you turn 73, increasing day 75 here shortly. [00:08:44] OG: But 73. So what he’s talking about is, can I strategically decide to pay taxes on this money today and be in charge of when I wanna pay those taxes? Or is it better to wait, or is it better to do some sort of combination of that? So you could take that pre-tax money, move it to a tax free bucket, which makes it tax free forever. [00:09:04] OG: But along the way, you know, on that little trip from one bucket to the other, you gotta pay the IRS some taxes. So the question is, is do I do the default plan starting at 73? Do I just take the money out as I need it and pay taxes when I need it? Or do I be more intentional and try to pay taxes at the rate at which I wanna pay it and move this into a, the tax free bucket? [00:09:23] Joe: Yeah. For anybody considering doing this, let’s break down just the pieces. The first thing is, so, oh geez, you explained the money is in. A pre-tax account, then you’re going to take the money out of that account, you’re gonna move it over to the Roth account. You’re going to have to calculate what the tax is before you do that. [00:09:42] Joe: ’cause you have to pay the tax one time without penalty today. And then whoever your custodian is, Schwab, fidelity, Vanguard, whoever it might be, they will help you make that transfer. And then when you pay your taxes, you pay the tax bill, you declare it on your taxes and you pay, you pay the tax [00:09:58] OG: bill. And a lot of times along the way they’ll withhold taxes as part of that conversion. [00:10:03] OG: So if you say, well I’m gonna convert a hundred thousand, you take a hundred thousand out of your IRA and you decide I want to pay 20,000 in taxes, so you put 80,000 back in your Roth, it’s kind of a less than ideal way to do it because you can see what’s happening, right? You’re taking a hundred grand out of your accounts, but only putting 80 back in. [00:10:20] OG: It’s much better to have that cash set aside, you know, outside of your investment accounts to be able to pay that tax. Um, but effectively that’s, is there [00:10:27] Joe: just a box to check that says, I don’t want you to withhold. [00:10:30] OG: Yeah, you have to do that. You have to tell the custodian, like you said, Schwab or Vanguard or whomever, you have to tell them how much you wanna withhold for taxes, if any, and just recognize that at the end of the year you’re gonna get a 10 99 that says, here was the, here’s what you did. [00:10:44] OG: And then, you know, you fold that into your tax return. [00:10:47] Joe: So here is then the problem he’s up against, he says he’s in the 22% bracket in, in the bottom. So normally I would say take as much as you can up to the next bracket, see how much tax that is, and convert as much Roth as you can. But he’s looking at possibly higher taxes in the future if he waits too long because later on there’s gonna be tax Anna, there’s gonna be tax on his Medicare and social security if he waits too long. [00:11:12] Anna: Yeah. So my thought on this situation here is that absolutely max out 22% bracket, if you can. Why not even get into the 24% bracket too? You’re not too far off at that point. Go into that area as well. Do that before you’re 62. Do that before you get into where if you do have Roth conversions that are going to affect income, that could eventually affect your Medicare premiums. [00:11:39] Anna: That is where it gets a little bit more dicey. If you can get this done now and you do have the cash, like OG was saying, you can pay the taxes with cash as opposed to taking money out of the actual conversion amounts you’re putting less in, um, that would be probably the best bet that you have. But ultimately it’s what can you afford to do? [00:11:58] Anna: Can you afford to pay the taxes right now on that and still put money into the Roth and pay the tax bill with cash or is cash a little bit strapped right now and maybe this isn’t the best time. Like OG said, you could really wait until you are forced to do it at RMD age and you’re forced to take money out and do taxes. [00:12:16] Anna: You don’t have to do Roth conversions. It’s just optimizing your portfolio at that point. [00:12:21] Joe: I love the idea of simplifying things by doing as much. Now, Anna, I like what you said there. I can see the calculation. I don’t think this is as easy as I do one or the other. ’cause I also like that, you know, Anna, you were talking about having the money to pay the tax maybe available ’cause, ’cause OG to your point, if you have them withhold y you’re taking money away from your retirement and you don’t want to do that. [00:12:43] Joe: Og I feel like it’s a little more complicated than, than Paul’s making it. I can see the spreadsheet here. Mm-hmm What’s the tax gonna be if I wait versus what’s the tax gonna be if I front end load this? I feel like there’s some nuance in deciding how this, and that’s gonna depend on not just his income today, but where he expects his income to be later. [00:13:05] OG: Well, it, I mean the reality is, is that all of those things count and the things that are un. Forecastable also count. So the thing that we don’t know is what are really gonna be the tax rates in 10 years from now, or 15 years from now when this break even eventually is supposed to happen, right? Because if you take money out of your account today, even though it’s, you know, you say, well, I’m gonna pay for it from cash, it’s still outta your net worth, right? [00:13:27] OG: It’s like if you had a million dollar net worth, now you have a 980,000 net worth. That’s just, that’s just how that works. And so the question is, how fast can you recover that 20,000 that you lost and pass what would’ve been a million dollars growing instead of 980,000 growing, if that makes sense. And so that break even can take 10 years, or 12 years, or 15 years. [00:13:47] OG: And the big unknowable thing is what is gonna be the tax rate? Like Anna said at 73 when he has to take the money out. What if tax rates are 15% and you took it out at 24? You know, that’s a really bad trade. Just like if tax rates are 32 and you took it out at 24, you’re gonna high five yourself. So I think there’s some unknowable things. [00:14:07] OG: The other piece is. And Anna alluded to this as it relates to your Medicare premiums that look back is two years. So if he’s 62 today and you know, thinking, okay, well maybe next year I’m gonna, I’m gonna start taking advantage of these Roth conversions, you have to forecast your income for what that’s gonna forecast, what that’s gonna do to your Medicare premiums two years in advance. [00:14:28] OG: We don’t know what the Medicare premiums are looking like in two years, except we know that they’re gonna be more expensive if you cross a certain threshold. So that’s an IM impossible thing, but something you have to take into consideration. And then the last piece, I think, but then also [00:14:39] Joe: to stop you right there. [00:14:40] Joe: Yeah. That is another reason to bias toward doing more now. [00:14:43] OG: Yeah. The known, known versus the unknown. Unknown, I think. And simplicity like you said. And I think the third piece of this is really just from a cashflow standpoint. You know, when you retire early on in your retirement is generally when you’re spending the most money, right? [00:14:58] OG: Like that’s when you do the trips, that’s when you, you know, you said you still got kids in college. It’s kind of the people say this, the, the, that’s the go-go years. That’s the time you’re doing those things. So what happens if you, you have all these fun plans and then you also have a major cashflow issue. [00:15:13] OG: You need a roof repair, or there’s a car accident and you have insurance deductibles or you know, whatever healthcare issue and you have some out of pocket expenses. So now you have this big healthcare expense, or you have this big out pocket expense. You weren’t planning on top of a year that you were planning on having a pretty good and now you also owe the government 50,000, probably not the year to do Roth conversions, even if mathematically from a tax standpoint it makes sense. [00:15:35] OG: So I think Roth conversions are a year by year decision that you make the decision in the fourth quarter based on what’s going on. You know, what’s going on in the market, what’s going on, my cash flow, how are things doing? For a lot of people this year, the stock market’s up, they’re feeling pretty confident, you know, from their investment portfolios. [00:15:52] OG: Maybe you’re ahead of your glide path of where I thought I should be for the end of the year. Maybe it makes sense to do a Roth conversion this year for some amount. [00:16:00] Joe: Let’s, uh, speak briefly to our younger stackers. I think that Anna, there’s a case to be made here to just avoid Roth conversions and if you can afford it, put money in the Roth 401k immediately. [00:16:11] Anna: Yeah, that’s step one. Even for him, if he’s contributing to a retirement account, make sure you’re contributing to Roth and if you’re young and your tax bracket isn’t as high as maybe it potentially could be in the future, make sure you’re maxing out on the Roth side as opposed to pre-tax, and then that way you don’t run into this situation in the future. [00:16:30] Joe: Yeah, if you could afford the little bit of pain now to pay the tax today, I always like I was biased toward the Roth. Let’s move on to episode 1724. We had Len Penso riding along with us. The main thrust of that episode was talking about donor advised funds with Adam Nash from Daffy, Adam Nash, of course, one of the creators of Wealth Front before he created Daffy. [00:16:56] Joe: During that conversation, remember our headline was about auto insurance and about the dos and don’ts of having an auto claim and stacker. Betsy had this comment about auto insurance. She said one thing a lot more people could self-insure if they chose to. Is roadside assistance. I dropped mine a long time ago. [00:17:17] Joe: I keep my older but reliable car in good repair. I carry jumper cables and a spare tire and I know how to use both. I know how to get around without a car and if it were necessary, which it hasn’t been yet, I could summon and pay for a tow truck. I think a lot of time OG people don’t think about summon. [00:17:32] Joe: I can conjure. All right wizard. I know [00:17:35] OG: I can conjure a tow truck. [00:17:37] Joe: Betsy’s standing on the side of the highway in her, uh, in her wizard cap, [00:17:41] OG: like the big book open and there’s like a cauldron Griffin door sweatshirt throwing like a dead field mouse in there and it bubbles up. [00:17:48] Joe: Just like Paul had a name for himself. [00:17:50] Joe: Betsy’s name now is Gandalf, Betsy Gandalf. But I think Betsy brings up a good point, which is I think OG often we get these riders on insurance like the tow truck, the roadside assistance, and we think, well wait a minute. If I didn’t pay for that and I know my way around a car a little bit, I might be able to save a few bucks in self-Insure. [00:18:11] OG: Yes, I agree with this a hundred percent. Like even if you don’t know your way around a car, how much is an Uber and a tow truck Once every X number of years? You know, it’s not that much. I remember one time, this is before we had kids, we were driving up to my wife’s cottage in Michigan in the wintertime. [00:18:27] OG: The snowplow had gone down the main road, but nobody had plowed the driveway and everybody from up north knows how. This is. The snow gets kinda this big mound at the end of the driveway [00:18:37] Doug: always. And it’s right after you’ve just shoveled it. [00:18:39] OG: Yeah. Well, no one shoveled this, so it was right after it snowed, so it was even worse. [00:18:43] OG: You know, it’s like midnight or something by the time we’ve gotten up there and I’m driving a little sedan and I’m looking at this going, how are we gonna get in the driveway? I’m like, you know, obviously Leroy Jenkins it, right? Like, ah, and just go, just [00:18:55] Joe: floor it. [00:18:55] OG: That was a bad idea. What could go wrong? [00:18:57] OG: So we end up like teeter tottering, half on the snow. Oh no. And half, you know, back of the car is sticking out into the road. So you trudge into the garage and try this, digging it out ourselves. It’s finally one 30 in the morning. I’m like, this is ridiculous. Which is a call, a tow truck. So call a tow truck. [00:19:13] OG: They’re like, it’s gonna be an hour before we get somebody out there. It turns out it was two. And then I get out there and the guy’s like, it’ll be 300 bucks. And I said, yeah, did you take credit card? And he’s like, no, I take cash. You’re kidding me. And I’m like, well, cash is in town like 10 miles away and it’s icy roads. [00:19:30] OG: He goes, it’s okay. I’ll follow you. If you get stuck, I’ll pull you out again. I drive, I had to drive all the way into town to give to the ATM to get this guy some cash to turn around and drive back by myself. The route I just came, hoping I don’t put it into another ditch. Finally pull into the neighbor’s driveway and just park it for the day. [00:19:48] OG: He gets up the next morning and he goes, I was really stupid of you to try to do that last night. And I said, oh, where you up? And he goes, oh yeah, I watched it for my bedroom. Just the whole time I was going, what kind of idiot is this? He said, I got this nice plowed, you know, 10 car driveway. ’cause he has a, a apartment building. [00:20:02] OG: And he says, why didn’t you just park in that? I said, well, I would’ve, if I would’ve known I could. He’s like, well, yeah, that story [00:20:08] Doug: sounded like the Michigan version of deliverance with the banjos playing. And the guy’s like, oh, I’ll, it felt like it. I’ll wait for you to get cash. [00:20:14] OG: It felt like it. This was long before find my friend on iPhone and you know, had to tell the wife, if I’m not back in three hours, call the police [00:20:23] opener: ing. [00:20:23] OG: So the tow truck was 300 bucks. And that’s where I’m getting at with this story. Yes. And I could have just as easily. Had that on my car insurance that whole time, it still would’ve taken the two hours to get somebody. It just would’ve been included in my car insurance for the last 25 years. [00:20:36] Anna: I feel like it makes sense when you have maybe younger kids who maybe drive like an older car. [00:20:43] Anna: When I was 16, 17, 18, I drove an old Ford Explorer that. Every time I drove down a hill and took a left turn, the car would shut off. [00:20:57] OG: That is awesome. That is such a great, that is such a great feature of the Ford Explorers. Yeah, the 1987 Explorers, that was my favorite year, [00:21:05] Doug: rather limiting. [00:21:06] Anna: I still drive one, it’s a little bit newer and I don’t have the same issue. [00:21:10] OG: You can turn left now. [00:21:12] Anna: I did call a tow, well, we had AAA at the time, called them probably four or five times a year. [00:21:17] Anna: So in that case, I was getting a little bit of a benefit there by having the AAA as opposed to calling a tow truck every time, paying $300 for it to be towed. And also, I was a 16-year-old, a 17-year-old. I had one number I had to call. I knew what to do in the situation and that’s all I had to do. Now, maybe I don’t necessarily need it, I have it, but it is nice and it’s not very expensive either. [00:21:42] Joe: Well, and that’s the thing, right, is cost versus benefit. I think people often aren’t evaluating, how big is this annoyance versus the amount that I pay, and is it worth it to pay for that? My bias when it comes to insurance, and Betsy, I’m glad that you brought this up. Thank you for the note on this. My bias is different, I think, than most people’s, is when, when they start out, when I was, when I was young and broke, I tried to raise my deductibles. [00:22:07] Joe: I tried to make sure that there was as much coming outta my pocket as possible, which was a hundred percent stupid. It was so stupid. But the reason was, was that I didn’t have any cash. So I thought a great place to save money was in my insurance premiums. That’s the last place you want to save money because you don’t have an emergency fund. [00:22:24] Joe: It’s actually, once you get that emergency fund in place, that you can then bias more toward, uh, having, having less insurance or deciding, you know, is it worth it for somebody else to take the risk so that I just don’t have to think about it. Betsy, thanks a ton For the question, we’ve got stacker Eric, who called in? [00:22:42] Joe: Guys, Eric wants to talk about trusts. You ready to talk about trust? OG is trust issues. Doug. Yeah. [00:22:49] OG: I want to talk about this. It all stemmed from that trust fall that you guys walked away from. We need to do this as an intervention. [00:22:56] Joe: And by the way, before we move on, I do wanna say something too about OGs cottage story, which Doug, you and I know about the earlier years of og heading up to the quote cottage. [00:23:10] Joe: Mm-hmm. Mm-hmm. Which people think is a mansion on a lake. Oh goodness. I think this is like, what was it, OG like, uh, 22 adult people in a, in a 600 square foot house. Yes. Well, I [00:23:19] OG: mean, in the wintertime there’s nobody there because no idiot drives up in the snow. Because the driveway’s not plowed. What kind of dummy goes to the cottage in the middle of the winter? [00:23:29] Doug: Just one. [00:23:30] OG: Yes. [00:23:31] Doug: I think OG said to me once the place is so small I need to go outside to change my mind. [00:23:37] OG: It’s a little snug. It’s very homey. You get a lot of family time. [00:23:42] Joe: Yeah. What was that, that joke they talk about, uh, one comedian was talking about like, uh, Manhattan apartments. It was really spacious. [00:23:48] Joe: There was room for a bottle of water and a pencil. Right. It was great. Alright, on to Eric and uh, trust what you got. Eric [00:23:58] caller: Joe OG and dub. Quick question for you. Can a third party trust get a step up in basis? My wife and I have a son with some disabilities and we’ve left everything in our, uh, beneficiary information to his third party trust so as not to screw up his benefits, but I’m curious as to whether or not that trust can get a step up in basis. [00:24:19] caller: Thanks. Appreciate you guys. Bye. [00:24:23] Joe: Eric, thanks so much for the call. And first, I, I wanna applaud you on doing the work that it takes, and this is not og uh, a small amount of work to make sure that special needs trusts are in place so that if something happens to you, that you’re able to do the right thing. [00:24:39] OG: This is why this stuff exists, right, is to make sure that you can take advantage of all the full benefits that you’re entitled, and then also protect the, the money, basically. [00:24:48] Joe: Yeah, the income stream makes sure that everything’s set up. So if something happens to Eric that his beneficiary’s taken care of, Doug. [00:24:55] Doug: Well, before we dive into how, let’s, let’s talk about why, why is Eric interested in stepping up the basis? Great question, Doug. [00:25:02] Joe: So why, why is he looking for a step up in basis? What does that mean? Anna, [00:25:06] Anna: step up in basis is when, if Eric were to pass away the assets that are sitting within his trust, get moved into his child’s special needs, trust, those securities or whatever else is sitting in there. [00:25:20] Anna: The cost basis that it’s at currently, let’s just say it’s $10, the market value is a hundred dollars today, the day that Eric passes away, the new cost basis is a hundred dollars when it goes to his child’s trust. What that means is. The child when they take the assets out, are going to pay less in taxes, less in capital gains taxes on that asset. [00:25:44] Joe: Yeah. Here’s a shortcut. Stackers that doesn’t work as well as people think that it does. They will often put two people’s name on the same account to try to just pass it on to a beneficiary. So let’s say I own a bunch of Microsoft stock that I bought in 1995, and I still have it today, but I put Doug’s name on the account with me. [00:26:07] Joe: Now I pass away. Doug has all the tax due, ’cause Microsoft has gone up by a bunch. When Doug sells it, his name’s on the account. People make this mistake all the time thinking it’s a shortcut and avoids probate and it does. But we created a huge tax problem if Doug were my beneficiary. I then would pass it on to Doug today. [00:26:28] Joe: Wait, wait, wait, wait. And there would be, none of Doug would pay none [00:26:32] Doug: of that tax. Yeah. Well, hold on. Why did you say if Doug were my beneficiary, I didn’t like that part. That’s, uh, we, we will take that offline. [00:26:40] Joe: A [00:26:40] OG: meaning to talk to you about something. [00:26:41] Joe: There’s only a few things you have to do to earn it. [00:26:43] Joe: You gotta earn it, Doug. You gotta earn [00:26:45] OG: it. This is very common, by the way, with houses. For some reason, people love to do this and they act all, they’re just so proud about it. Like, oh, I, boy, did I pull one over the government That don’t happened to [00:26:56] Joe: my immediate family. [00:26:57] OG: I did this and how great is this? And you’re like, yeah, you just, uh, what, what, what’d you build the house for in 1940? [00:27:03] OG: Grandma, oh, grandpa built it for $8,000. It’s like, well, great news now. Everybody’s gotta pay freaking taxes on this. We could’ve just got it tax free if we just had a normal beneficiary. Super easy. [00:27:15] Joe: That’s all we had to do. So we know that people get a step up in basis. Og does this third party trust get a step up in basis? [00:27:22] OG: Yeah, it’s the same thing because the trust is just an extension of you when, let me put it this way, assuming that the money gets transferred into the special needs trust on Eric’s death, then yes, that’s what would happen. Or if his trust converts to a special needs stress or something, if he’s putting money into a trust today that is met for his kid and is a irrevocable trust, then it is what it is, right? [00:27:47] OG: Like then that’s the gift as of today. So I think he means like, Hey, I’ve got money and when I pass away and my spouse passes away, then this money is meant for my child and it’s gonna go into a special needs trust to take care of him. In that case, yes, asterisk, this is something you want to talk to your estate planning attorney about, and also your tax person just to double check because there might be some nuances here that we’re not. [00:28:10] OG: Talking about with with a big, broad brush stroke. But generally speaking, if it’s your money and it goes to somebody else, they get step up. [00:28:19] Joe: After the break, we are going to have our TikTok minute. This is a part of the show where we shine a light on a TikTok creator who’s either creating some brilliance or air quotes. [00:28:27] Joe: Brilliance, we got one coming up, but first, Doug, time for our break. For today’s trivia. What’s going on, man? [00:28:39] Doug: Hey there, stackers. I’m Joe’s Mom’s Neighbor, Doug, and have you ever heard of that contest between a chimpanzee and professional stock traders? Well, that happened this week. Back in 1993, a Swedish news newspaper pitted the chimp against five stock analysts, and you’ve already guessed what happened, right? [00:28:58] Doug: Of course, the chimp won. But here’s the question. What instrument did the chimpanzee use to beat the five analysts? I mean, besides the wooden club? I’ll be back right after I go monkey around during the break. [00:29:20] Doug: Hey there, stackers. I’m expert, stock picker and guy who’s used to working with Monkeys Joe’s, mom’s neighbor, Doug. Ah, if only Joe and OG could be trained the way these scientists trained that chimp to pick stocks, we wouldn’t have to work in the basement. Check that we would, but we wouldn’t have to. I mean, why would we pass up on free rent and the peaceful Zen-like sound of water constantly dripping. [00:29:45] Doug: So anyway, after a month, the chimpanzee earned 190 bucks. On an initial investment up 1,250, the stockbrokers, they only earned 130. So what instrument did the chimp use to beat the five stock analysts? If you said a dart, you won. And now three people who love throwing darts at financial security, Anna, Joe, and og. [00:30:11] Joe: Did the Wall Street Journal did something similar to that as well. Og, I think I remember the Wall Street Journal also doing a competition that was, don’t recall very much like that. Yeah. But very, very famous moment when the chimp throw in the Dart beat the analyst. Hey, let’s see if you can guess the TikTok minute. [00:30:30] Joe: This is the part of the show where we shine a light on a TikTok creator who’s either creating something brilliant or air quotes Brilliant. Anna, it’s your first time here. You think we’re gonna see some brilliance or some air quotes? Brilliance today on the TikTok minute. [00:30:43] Anna: I don’t know if I’ve seen much brilliance on TikTok, so I’m gonna say air quotes Brilliance [00:30:48] Joe: Boy, Doug. [00:30:50] Joe: You could tell who works. Apple doesn’t fall for from the tree does it day. How’d you get through that interview, Anna? With that point of view, I can hire [00:30:57] Doug: her. [00:30:58] Joe: You know the good news about this one, stacker Jenny, uh, sent this in our meetup group in Minneapolis, St. Paul just watched Join or Die. That documentary we discussed back on episode 1697, where we talked about how if you join a group and you don’t isolate, as you get older, you’re much more likely to not only be happy, but also have some longevity. [00:31:18] Joe: While stacker, Jenny said this has a lot to do with the same thing. Bob Lodi at Seed Time Money had this related stat. On TikTok, here’s Bob. [00:31:29] TikTok: People who say that their health is poor are 400% more likely to die in the next four years than those who say that they’re healthy. What? Even if they are equally healthy at the time. [00:31:39] TikTok: So not like some like backyard hillbilly study. This is at Yale. [00:31:43] opener: Wow. Um, [00:31:44] TikTok: five other studies that involved 23,000 participants mirrored that same result. Oh my gosh. I think this has deep implication to our finances. Mm-hmm. Because I, I see so many people that have spoken things like, I’m just bad with money. [00:31:58] TikTok: Mm. We’re always broke. It’s always hand to mouth. It’s, there’s never enough. My challenge to you is to ask yourself, what are you speaking over your life? What have you been speaking over your finances, over your family? Are they aligned with his word? Mm-hmm. Or are they aligned with fear? And so, bottom line, you know, this isn’t magic this, but I think our words are more powerful than we realize. [00:32:19] TikTok: Great stuff actually [00:32:21] Joe: from From Bob? [00:32:22] Anna: Yeah. I take it back. I take it back. Yeah. [00:32:24] Joe: It looks like the new kid was wrong. It is pretty rare. I mean, Bob Loic great guy at Seat Time Money, but you know, you guys work with people every day. And Anna, it’s so funny. Back when I was a financial planner, if somebody was positive and optimistic and had a kin do attitude, I’d meet with them again for their next meeting and they’d accomplished a bunch of stuff. [00:32:43] Joe: Mm-hmm. And if somebody came into the meeting and goes, I don’t have enough. I can’t do it. I can’t. Even if these two people to Bob’s point, had the same amount of money and the same opportunity, man, just that attitude difference changed everything. [00:32:56] Anna: Yeah, I think they also call it a scarcity mindset. So when you are really concerned about your resources and you’re really concerned about what’s gonna happen with your finances in the next year, you’re really caught up in just like what’s happening today and you have really negative mindset. [00:33:13] Anna: I really do see that those people have a harder time progressing and, and moving towards their financial goals, like you were saying. Whereas the people who. Have a positive mindset and are really excited about what they’ve accomplished already and what’s to come. I find that they do move a little bit faster towards those goals, which is really awesome. [00:33:33] Anna: I’ve been trying to do that in my own life too, not just with finances, but every other part of my life, whether it’s fitness goals or finance goals, career. Anything really you can apply this to. It’s not just finances. [00:33:46] Joe: It is so wild. It’s funny, this is what I like OG about the financial plan is that I would have clients come into my office and I’m sure nothing has changed. [00:33:54] Joe: Right? Well, I see it on social media all the time. I know nothing has changed. People would come in, they want to talk about what’s going on with the government, what’s going on in quote society, what’s going on with Jerome Powell and the Fed, what are they gonna do, these statistics that have nothing to do with them. [00:34:10] Joe: And when I would refocus and go, Hey, our plan says that you need to have $42,000 by today in your retirement funds. Let’s count that. And all of a sudden we’d get rid of all that crap and we’d focus instead on whether you’re a header behind on your own goal. Like wow, the cha, the change in attitude when we focused on your goal instead of all the other stuff changed the whole game. [00:34:35] OG: There’s so many different things here. I was thinking about the Napoleon Hill Book, think and Grow Rich, like how old is that book? Right? And it’s all about mindset and positive mental attitude. And the thing that you focus on is what’s gonna show up in your life. You can think about Stephen Covey and the Seven Habits book. [00:34:51] OG: Tony Robbins has a big thing about, you know, it’s impossible to lie to yourself. So when you’re talking about your, your money stuff, or like, you know, you sit there and you stew or you think about your fitness goals or you know, whatever, and you, and you’re just kind of going like, why can’t I get this right? [00:35:05] OG: And your brain goes, because you’re an idiot with money. Like that is in your soul at that moment, right? Like there’s no way to, you have to change the thinking on that. When you focus on the things that you can control, it’s so much more powerful because that, that takes away all those externalities. I mentioned a week ago that I got back into Ted Lasso, and I know this is old news for everybody. [00:35:25] OG: I think I’m on the second season and the, it’s the season where the psychiatrist or psychologist is part of the team, and Ted has reluctantly let her into the organization and it’s kind of reached the head where now he’s having this big breakdown, spoiler alert, and uh, and he’s talking about his dad and he’s, you know, I hate my dad and I hated how he did this, and, you know, and this, and she’s just sitting there with him and she goes, what did you love about your dad? [00:35:51] OG: And I know this is all scripted, but this would happen in real life. And I know Anna’s experienced it. And so have I. When people just go, they’re all on the Jerome Powell thing, or they’re all about all this stuff. And you go, well, what’s going well? And they’re like, wait, what? Like, no, no. Like, I get all that, but what’s going well so far? [00:36:07] OG: Because let’s just, just kind of. Put this pendulum back to the middle for just a quick second. And in the show you can see that flip for him. Obviously it’s scripted and it’s meant to be, but that’s how it really would work. It’s a pattern interrupt. It’s a pattern interrupt. ’cause he’s going, I hated my dad. [00:36:22] OG: He did this, he screwed us. You know, he did this, he did this, I hate. And she goes, what did you love about him? And he’s like, wait, what? She’s like, well, what did, there had to have been something. He’s like, well, I mean, there was this one time. And then he tells a story. And you’re right. It totally for those, for those people that have used record players, you know, not, uh, probably just you two guys, but, uh, pc. [00:36:44] OG: Yeah, [00:36:44] Anna: I have one. It’s in the basement. [00:36:46] OG: They’re coming [00:36:46] Anna: back. Oh, [00:36:46] OG: wow. All right. I guess I’m the, yes, I [00:36:48] Anna: have one. Anna [00:36:49] Doug: going old [00:36:49] OG: school. [00:36:50] Anna: Yeah, it’s put away because my one and a half year old would destroy it. But [00:36:55] OG: I have one. It’s got the vintage. All right. Mm-hmm. Who knew? But if you’ve scratched the record, right, that’s what you’re trying to do. [00:37:01] OG: You’re trying to interrupt the pattern, trying to scratch the record. So. I agree with this. TikTok. Fine. There’s one. How about that? There’s one so far. [00:37:08] Anna: I agree too, but you can’t really go wrong on this topic. [00:37:10] OG: No. [00:37:11] Anna: Positive thinking is awesome. I agree with og. Like we’ll have meetings with clients and when you get stuck in that, like, oh, we got daycare bills, we got this that came up the roof, everything’s going wrong. [00:37:23] Anna: And then you show them the big picture and you’re like, well, even if things are going wrong today, you guys are looking awesome. Yeah, yeah. They leave that meeting feeling so good and that gives them motivation, keeps the momentum going. It’s just another level of keeping that positive thinking going. [00:37:39] Doug: Listen to Anna trying to save face here and be like, oh, I was in the whole time. Yeah. I loved this one. Yeah. I knew it was gonna be great, you know, [00:37:46] Joe: and thanks to stacker Jenny for bringing this star attention and for people that haven’t watched this documentary join or Die about not isolating as you get older and about being a part of a community and how important goal is [00:37:55] OG: to isolate. [00:37:56] OG: When I get older, that’s when I’m like, like, I’m looking forward to not having to hang out with you guys. Like when do I get to not do this? You know? I mean, it’s fun at all, but there’s a day when I can like not have to be around people ever again. How great is that gonna be? [00:38:12] Joe: I think you wanna watch this movie OG ’cause Uh, think so. [00:38:14] Joe: All [00:38:14] OG: right. Maybe I’ll check it. [00:38:15] Joe: Yeah. I think a big part of that is, but where would you ask for, [00:38:17] OG: yeah. [00:38:18] Joe: Let’s move on though. Stacker. James has a question. I don’t have any [00:38:20] OG: friends. [00:38:24] Joe: Oh, gee’s. Like, but I don’t want friends. Stacker. James, uh, wants to talk about some end of life planning. [00:38:32] caller: Hey guys, James from Saudi, Daisy, Tennessee here. [00:38:35] caller: Just wanted to let you know that I really enjoyed your episode with Tim on estate planning. I don’t really have a question, but instead a bit of real life situation from my past to highlight the potential for very near end of life planning several years ago, my mother-in-law was nearing death. She was the primary beneficiary of a trust from her husband’s estate, and I was trustee. [00:38:56] caller: The trust had some appreciated assets to attend about a $400,000 gain I could have and thought about distributing the assets to her account so that we as Aris could get the step on vote basis. When it came down to it, while my wife was essentially watching her mother die, I just could not pull the trigger as emotions got in the way and it felt wrong to benefit from my mother-in-law’s death. [00:39:17] caller: I guess my point is there are some end of life tactics that could be implemented. It’s planning, and you should not feel guilty about planning. In my case, if my mother-in-law knew that we could have gotten that sort of step up him basis and I didn’t take it, she would’ve probably given me a talking to, or as we was lovingly said, she would’ve given me the big hairy eyeballs. [00:39:38] caller: As always, I very much enjoyed the show, especially the trivia. You go, Doug [00:39:46] Joe: punished. He had me at hairy eyeballs. I’m a little lost though, James, on what you did. I got it. Oh, talking, you’re nodding. Talking about, yeah. [00:39:53] OG: Yeah. This is an estate planning technique and I think there’s some, I, I don’t think he should beat himself up too badly because I think there’s some limitations here around timing because of this issue. [00:40:04] OG: So what he’s saying is. Mom had some assets that had appreciated and because of the way the trust was structured, if we were gonna inherit it, we were not gonna get the step up. Like, mom got the step up a long time ago, the assets have appreciated and now we’re gonna get the but, but we’re not getting another step up basically is what his thinking was. [00:40:25] OG: So his thought was, well, if I give all these assets to mom right before she dies, like legally give them to mom, then she gives ’em to us. Then we get that step up again. Uh, I’ve seen that work the other direction. So again, estate planning, kind of 3 0 1 here. But let’s say that you’re a, uh, CEO of a company. [00:40:43] OG: You have a bunch of highly appreciated shares and you have 85-year-old parents. What we’ve seen happen is the kid gives, gives mom and dad these appreciated shares. So by the gift they get the basis. So they now have all these shares with a big tax problem. Right. 10 years later, mom and dad die and give the shares back to the kid with the step up in basis. [00:41:12] OG: This is a little bit more complicated, and from an estate planning technique, you definitely need to have a pro here. But I think there’s some timing issues there as it relates to, you can’t do it like on their deathbed and then like, bingo bango look at me tax free. So I don’t think he missed anything here. [00:41:26] OG: No. I swear [00:41:27] Joe: to God she’s still alive. I swear to God she’s still alive. Yeah. He’s like, die dammit. We need the step up. [00:41:35] Anna: Yeah. You know, James, I feel like you did the right thing. Yeah. I don’t know if it would be good if she’s like, you know, last couple days you throw some paperwork interface. [00:41:44] OG: Yeah. [00:41:44] Anna: So I, I wouldn’t beat yourself up about it. Yeah. [00:41:47] OG: But this goes back to like what Tim was talking about in the episode. It’s all about planning, not the plan, right. [00:41:54] OG: It’s, it’s really going through these thinking tools of here’s where we are. Here’s what you know, here’s where all, pardon the expression, where all the bodies are buried, right? Like, we need to know where all the stuff is. Well, too soon, too soon, too soon. She’s still warm for God’s sakes. Um, you gotta have an idea of where all the stuff is so that you can put a good plan together. [00:42:15] OG: And sometimes there’s some unintended consequences and we’re gonna talk about unintended consequences. But you gotta be careful with that plan because what happens if, in my example, you give mom and dad a bunch of shares and you go, wink, wink, nudge, nudge. You can give ’em back to me and they go, actually, we’ve decided we’re gonna donate it to church. [00:42:29] OG: You know, it’s their money right now. They could do what they want and you know, so you gotta be careful. So definitely get a pro here, but I don’t think you should beat yourself up over it, you know? It’s okay. [00:42:40] Joe: Yeah. Great story James. And thank you so much for the kind words about our episode with Tim Semal. [00:42:45] Joe: People wanna go back to that. That’s episode 1723 where we dive into a bunch of questions. And you know what? I [00:42:51] OG: think we should start naming the episodes like, you know, at the beginning of movies where it has the copyright, but it’s in Roman numerals. Can we start doing that? XXVI? Yeah. It would be like MI don’t even What’s 1500 mv? [00:43:06] OG: Mm. Xx. No, that’s cc. [00:43:10] Doug: Uh, [00:43:11] OG: I [00:43:11] Doug: don’t [00:43:11] OG: know. 500 X is 10. [00:43:13] Doug: Yeah, [00:43:13] OG: C is a hundred. I don’t know. [00:43:15] Doug: It was mc. Everything used to be MCM because it was the year 2000 seed before the M made at 19. Yeah, the M is 1,500 [00:43:24] OG: now it’s, mm. Anyways, whatever. Carry on. Right? Joe’s like, I can see Joe’s eyes glazing over. He’s like, what are we talking about? [00:43:31] OG: You have money questions? Let’s change it to Roman. Turns about the Romans. [00:43:34] Joe: Yeah. Let’s talk about the important stuff like changing our numbering to Roman numerals. This, that, that’ll keep him coming back. [00:43:40] OG: M-V-X-C-I-I-L-M-I, I dunno. [00:43:47] Joe: We have a couple more we wanna tackle here in the next few minutes, but we got a nice note from an anonymous person in the basement ’cause they were sharing some of their personal financial picture. [00:43:57] Joe: Said, hello. I’m seeking advice about changing my portfolio from its current state to one more in line with the efficient frontier. About 84% of their investments are in the total stock market index where they’re buying just a little bit of everything. About 8% of our market equities are in the total stock market indexes held in our taxable brokerage accounts. [00:44:17] Joe: While I don’t have dollar figures here, the eight percent’s not insignificant. It’s a tad less than my wife and I earned per year. The remaining 92% is simpler. These are tax favored accounts or my 401k, which is reasonably good choices for getting closer to the efficient frontier. Uh, the basic question here that they dive into is when they’re moving stuff over to be more efficient. [00:44:39] Joe: They’re seeing recommendations of us large cap growth and large cap value. And based on their understanding, there’s some overlap between the total stock market indexes and those. So does it make sense in the taxable accounts to go from total stock market index over to the large cap growth, large cap value? [00:44:58] Joe: Like is the juice worth the squeeze to make that? And they’ve held these for a long time, so there’s going to be, they’re gonna be taxes to pay. My initial take on this OG was, was definitely not, I, I don’t think, when you look at the long-term results between the large cap growth or large cap value index and the total stock market index, there is enough of a return difference, volatility difference in a taxable account to make that change. [00:45:27] OG: And especially when you have so much more money outside of the. Taxable accounts and tax favored rebalancing in your 401k or IRAs or Roths. Just make all of your rebalancing choices over there where it’s tax free Doesn’t cost anything easy. Yeah, [00:45:39] Joe: totally. And as you’re selling, sell from those total stock market index positions when it’s appropriate. [00:45:45] Joe: Yeah. Or, [00:45:45] OG: or as you’re purchasing more stuff, stop buying that and start buying your small companies or your international and your brokerage account to help diversify it. But I wouldn’t, I never like martyring myself to the IRS in the spirit of like no marginal improvement. [00:46:00] Joe: Yeah. And especially when you look at the long term results of these, I mean, when I was doing the research about the total stock market index and the s and p 500 over like a 50 year timeframe, and I took different 50 year timeframes, the results were fairly close to identical. [00:46:16] Joe: Were, were not that much different. And I guess it’s gotta be OG because over long periods, the large cap kind of drives the bus. [00:46:25] OG: Well, I mean, this is the fundamental piece around diversification you’re trying to add. Non-correlated assets. And so when you take a look at those different buckets and you say, oh, well I need to add this. [00:46:38] OG: I don’t have any large companies that have been around a long time, is it a diversifier by adding it to your portfolio or not? And clearly it’s not. So why would you add it to, to do what? What’s the purpose? The purpose of diversification is to have a bunch of stuff that acts independently of one another so that you get all of the return of all of the market just kind of over different periods of time that if you look at an asset class and say, if I add this, does it add a. [00:47:06] OG: Diversification benefit non-correlation to my existing portfolio. If the answer is no, then what the heck are you doing? Putting it in there? Yeah. Like you’re just, you’re adding complexity. You’re adding another line item on your statement for no reason. I would say small companies add diversification benefits. [00:47:21] OG: Big companies and small are diversified from one another. International companies are diversified from US companies up and coming countries. So we call that emerging market. That is di a diversifier. Real estate commodities are diversifiers, but if you say, well I can go mid cap growth or small cap growth, which one? [00:47:39] OG: Well, they’re the same. I get that they’re different stocks, but they perform in the similar manner. They’re gonna behave similarly. So if you have mid-cap in your 401k, you don’t get any benefit by having small cap statistically. So just keep it simple. [00:47:52] Joe: Our friend here pointed out that I made a video about this. [00:47:55] Joe: We’ll link to it in the show notes at Stacky Benjamins for people that wanna. Want to look at the basics of understanding how to diversify your portfolio a little more scientifically. I also spoke about this at the Economy Conference last year, and we’ll also link to really a great video that our friend Dyna Miriam made of that event. [00:48:14] Joe: And, uh, me on the stage talking about that and what the happiest retirees. It’s a [00:48:18] OG: really great video of me will like of me. [00:48:21] Joe: It’s so, it’s so fantastic. It’s because it’s me. It’s such a great [00:48:24] OG: video that Diane made of me. I wanna make sure that you guys get another video of me. I’m [00:48:28] Joe: just saying that the production quality was fantastic. [00:48:32] Joe: The fact that you get to there, [00:48:33] OG: put on a pig, Diana [00:48:37] Joe: at me is a bonus. See what I was talking about, Anna? Mm-hmm. This is what it’s like working here. Yeah. It’s super fun. Yeah. Fun in air quotes. Mm-hmm. Last question of the day comes to us from stacker Patrick, and he wants to talk about HSAs, guys health savings accounts. [00:48:51] Joe: Patrick, bring it. [00:48:53] caller: Hey, Joe OG and of course Big D. I have a question about HSAs. I’m married and my wife and I have about $55,000 saved and invested in an HSA in my name. We don’t use that money for current medical expenses. We’re able to pay for those through our normal cash flow every month. It’s just gonna keep building up and we always max out the contributions. [00:49:21] caller: I’m 34 and my wife is a little bit younger than me, so we’ve got a lot of runway here for this. HSA invested dollars to compound. My plan is to save that money for long-term care. If we ever need that, you know, 50 years from now, hopefully by then it could be a substantial amount of money. Is that too much money? [00:49:46] caller: Is that something we should be taking out and withdrawing so it doesn’t get to be too big of a sum? Uh, I’d like to know your opinion, especially because inflation could make it so that current expenses today might not be worth a dinner at the Sizzler in 40 or 50 years. [00:50:05] Doug: Thanks. Before we dive into this, can we talk about how awesome Patrick’s accent is? [00:50:12] Doug: Just, I mean, the Minnesota accent, wherever, you know, North Dakota style, wherever he is calling from, it’s, oh yeah, we gotta worry about the cash flow. I just love, it’s just [00:50:21] Joe: awesome. Dialects all over the world. All over the United States. It’s just so, so fun. Yeah, [00:50:26] Doug: it’s great. So much better than the Michigan accent. [00:50:28] Doug: I just like that he remembered to call you Big D, which we Big D Well, everybody loves the Big D. All the [00:50:32] Anna: callers give you so much love, Doug. It’s huh? Yeah. [00:50:36] Doug: Unwarranted. But [00:50:37] Joe: yeah, not sure why as they should. Uh, by the way, Patrick, before we dig into your question, 34 years old, we just gotta acknowledge this. [00:50:43] Joe: 34 years old and $55,000 in this HSA. That is incredible. Damn. Yeah. Nice job. Nice savings job, Patrick. And it goes back to what Doug’s dad told me, which was. Careful what you, you said it on Monday, there’s a lady [00:51:00] OG: present, [00:51:02] Joe: you said Not that thing. The other thing. Oh [00:51:09] Joe: no. On Monday. On Monday, you said your dad said that saving is not a feeling, it’s [00:51:15] Doug: an action, right? No, he didn’t say that about saving. He just said that in general. He said, we really said it when we were, my wife and I were thinking about, are we ready to have kids? And in that context, his piece of advice was, being ready is a decision. [00:51:30] Doug: It’s not a feeling. [00:51:32] Joe: Okay, well maybe it didn’t apply, but it sounded good at the time. It sounded cool. Yeah. [00:51:38] OG: Why is this like the scene from Anchorman where he’s like, when in Rome? And she’s like, Nope. Still don’t have it. It’s like trying to use all the phrases that he’s learning and [00:51:48] Joe: just throwing stuff out there just [00:51:50] OG: to try new things just to see if it makes sense. [00:51:53] Joe: Patrick, apparently what Doug’s dad said did, does not apply. However, Anna, do you like the idea of the 55,000 earmarking that toward long-term care? [00:52:02] Anna: I love the idea of it. When you are older and you’re 65 or how whatever age after 65, you can take the money out of the HSA for whatever purpose. At that point, you don’t have to your market for long-term care. [00:52:18] Anna: I would say max it out. Max out your HSA, if you can do that. You’re already at 55,000 and he mentioned, is this too much money? No. There can’t be too much money in an HSA because Sure. It could be for long-term care if you want. That’s awesome. If you don’t end up using long-term care, you could take the money out and use it for something else after age 65. [00:52:38] Anna: Doesn’t have to be long-term care, but if that’s how you mentally count it for, then that’s great. [00:52:44] Joe: That’s the cool thing. Patrick, about the HSA, is that this becomes like a supplementary retirement vehicle, Anna. Mm-hmm. I mean, this doesn’t even have to be a health savings account if there’s extra money thereafter. [00:52:55] Joe: 65. [00:52:56] Anna: Yeah. You can kind of look at it as almost like an IRA. You need to know that it’s not 59 and a half, like a regular IRA. If you wanna take it out for stuff other than medical expenses. It’s age 65, so a little bit older, but for the same purposes. You bring it out and you take the money out, you pay taxes on it, but you don’t pay penalties on it at that point. [00:53:17] Joe: Just like a traditional pre-tax 401k. [00:53:20] Anna: Yeah. [00:53:21] Joe: At that point, [00:53:22] Anna: send it. Max it out. [00:53:24] Joe: Yeah, I like that. Do you like the idea of this early OG of earmarking it toward long-term care? [00:53:29] OG: You know, I, I’m one of these people that thinks that everything is for everything. Everything counts, basically. So if it makes sense in your brain to say, well, this is my money for this, then that’s okay. [00:53:41] OG: And the ex, the example that I use is, if you had $50 million in your IRA, would you say, well that’s not my, that’s not my health money. That’s for retirement. No. You would be like, I have $50 million. I just would for whatever I want. You know, I can buy a house with it or go on vacation or do whatever. We like to compartmentalize like in our brains, like where things are like, this is my retirement money. [00:54:00] OG: This is my healthcare money. But Anna’s right. I mean, it’s just basically another place to save, you know, another $8,000 or 8,300 bucks, whatever it is this year for, for a couple. And if you don’t use it, this is the big thing that I would say. You’re 30 years old, you don’t have any idea what the future’s gonna be. [00:54:15] OG: No offense to the 30 year olds around, but you don’t know nothing about nothing. Pull up your pants and face North talking to you. Yeah, [00:54:22] Anna: watch it. Wow. [00:54:24] OG: But I’m saying like there’s a lot of life to live between 30 and 65, or in his case 30 and 85 that he’s thinking about for long-term care. You don’t know if there’s gonna be a kid that falls and breaks an arm and that’s a $5,000 deductible. [00:54:36] OG: You have a job loss and then you have a healthcare expense and you’re like, oh, thank God I’ve got this, you know, thing. So it gives you some flexibility. So if you have the cashflow to save it, this is a great place to put it. If it makes you sleep better at night going, this is my, my long-term care money, I did some quick calculation and I said, Hey, if I had 50 grand in an account for the next 50 years and it grew at market rates, I’d end up with about $4 million. [00:54:58] OG: You go, that’s enough for healthcare, right? Or long-term care. Well, long-term care costs $6,000 right now a month, and it inflates by six or 7% a year for the next 50 years. What is it gonna cost About a million dollars a year. So you, there’s, there’s four years. There’s your four years of long-term care, a million bucks a year. [00:55:17] OG: You know, if that’s, if that’s what ends up happening. But I would think about it a little differently. Personally, I would say this is just part of my, part of my net worth that I’m continuing to grow. And the idea of having it in this protected bucket gives me a bunch of flexibility in the future. And that’s really what I’m interested in is can I, you know, it’s the same question that we had at the very beginning where it’s the with Roth and traditional, and we get this question all the time, should I do Roth? [00:55:41] OG: Do both. You need the flexibility because we don’t know what the future’s gonna hold. And having different places where you can strategically take money from, depending on the circumstance, in an advantageous manner that takes the IRS out of the middle of it is awesome. So if you end up with a healthcare expense and you’re 57 and you’re like, bang, tax free, or you retire early and you’re like, I want to do this, boom, tax free, and I do a conversion at 12%, like, that’s awesome too. [00:56:07] OG: So it’s great to have all the different buckets. Keep your foot on the gas. You wanna gain flexibility. [00:56:14] Joe: I wanna go back to earlier, you know, when Betsy was talking about car insurance and she doesn’t need the roadside assistance. Patrick, the more money you have in that HSA, the more you’ll be able to self-insure for whatever you want. [00:56:27] Joe: The long-term care fine. Your, your car insurance, raise your deductible, whatever it might be, just putting more and more money there. Uh, I personally do like the idea of bucketing. I know our, our friend, uh, Alan. Corey did this when he started buying real estate. He would buy a piece of real estate and it would create enough cash flow that he didn’t have to pay the electric bill anymore, and he thought of that house as his electric bill. [00:56:50] Joe: Then the next house was his grocery bill. Then the next house was the gas bill and then the next house. He’s like, ’cause I hate paying bills. So I wanted all these houses. And next thing you know, he had a real estate empire just thinking about the bracketing. So I, I think to Anna’s point and OGs point, Patrick, I’m, I’m gonna third this one. [00:57:06] Joe: If it helps you go forward by putting it in that bucket more approach. How many neighborhood [00:57:10] Doug: did he have to own before he could pay for all his streaming services? ’cause that’s what I’m working on now, right? Yeah. [00:57:18] Joe: 87 I find. Why is it when I cut a streaming service, by the way, immediately they come out with a new show that I get FOMO about. [00:57:26] Joe: I cut Apple TV a few months ago and they came out with that Seth Rogan show that I wanna watch now studio and I can’t. And I, and I can’t watch it. Yeah, it sucks. Yeah, that’s what you said. That’s what you said. But you and I disagree so much that I’m like, oh, I bet I’d like it then. Ah, man. Doug hates [00:57:40] OG: it. [00:57:41] OG: I’m, [00:57:42] Joe: and by the way, again, deeper dive into HSAs. Let’s transition out into the back porch. Although this whole show has been a back porch where the back porch, normally at the end of the show, we have our community piece talk about what’s going on with all of our stackers. But clearly today you showed up with some great questions. [00:57:58] Joe: If you’ve got questions for us, stacky Benjamins dot com slash voicemail, uh, the way James and Patrick and Paul and Eric all called in, you can, I’ll getting t-shirts. Yeah, absolutely. But tonight, HSA 1 0 [00:58:12] Doug: 1. It’s finally tonight, right? We’ve been talking about this for weeks. It’s in a few hours, [00:58:16] Joe: isn’t it? [00:58:17] Joe: Yeah. If we just got done talking about HSAs and you’re like, I don’t even know what the hell. Know you’re talking about just the basics. What is this thing? Open enrollment’s coming up, how does it work? I’ll be on YouTube tonight. Stack your Benjamins dot com slash HSA to sign up and, uh, come join me this evening. [00:58:37] Doug: That’s tonight, September 3rd in the year 2025. Eight 30 Eastern. Eight 30, [00:58:44] Joe: yeah. Eight 30 Eastern, five 30 specific, as Doug likes to say. Specific good stuff on the HSA front. [00:58:52] Doug: Uh, we also, Doug got a couple notes. Yeah, we did. We got a great note from John who said, really enjoyed the discussion about the fan dueling of our 4 0 1 Ks. [00:59:02] Doug: Talking about all the private, maybe [00:59:04] Joe: the Anna. This was a discussion we had about all of the, all the private equity going into 4 0 1 Ks now, and how our, yeah, before we know it, our 4 0 1 Ks gonna be like fandule, where I could just bet inside my 401k whatever I want. [00:59:18] Doug: That’d be smart. Joe. It took you four, it took you 14 or 15 years, but you finally came up with the phrase that will define your career in podcast fan dueling. [00:59:25] Doug: The I fan dueling of our 4 0 1 Ks. It was so good. That was so amazing. Anyway, John said, got to thinking about my diversification and then bam it hit me. I have added DraftKings as well, so there you are. Just changing lives. Joe, John maybe missed the point [00:59:44] Joe: of, of that whole thing, [00:59:46] OG: unless that four way parlay hits, in which case [00:59:49] Joe: fire doesn’t matter. [00:59:51] Joe: Yeah. John, thanks for the kind words. Thank you to all of you for hanging out. Hopefully you can hang out with me and talk about HSAs tonight. Uh, thanks to all of our stackers that helped us make today’s episode. And Anna, thanks to you for hanging out. Thanks guys. Was it ever bit as bad as you thought it was gonna be? [01:00:09] Joe: No, it wasn’t that bad. Done. Wow. [01:00:12] OG: It wasn’t that bad. Put that on a t-shirt. [01:00:15] Doug: That’s what we’re [01:00:16] OG: striving for. How was your time on Stacking Benjamins quote? It wasn’t that bad. [01:00:21] Joe: Not as bad as expected. [01:00:23] OG: Right? It’s like a movie poster with the reviews of like Cisco and Ebert. Not as bad as I thought. [01:00:30] Joe: It’s like the back of Len Peso’s book. [01:00:32] Joe: You know all those reviews. Yeah. Benzo’s an idiot. Five stars. If you’re somebody who’s here though, because you are not hoping to gain a little bit of knowledge about an HSA or you don’t want to hear about John’s DraftKings pics, you’re here because you really wanna put together a full financial plan. [01:00:51] Joe: Well, guess what? OG and Anna’s calendars are open. So if you’re looking for better help in your corner, it’s Stacking Benjamins dot com slash OG gets you to Anna’s and OGs calendar to set up a consultation to talk about how their team can help your team as we man plan for 2025 in plan in 2025. I hate to say this ’cause it feels like the year just started for 2026. [01:01:16] Joe: I think it just threw up in my mouth. [01:01:18] Doug: 2026. This is news to me. I’m really interested that you said this, Joe, because every time I’ve tried to get on either of their calendars, there’s never an opening. It’s so weird. Weird. We’re in this calendar year now You’re busy. Now you’re telling everybody else. Yeah, there’s, there’s availability. [01:01:32] Doug: Doug, we have a [01:01:32] Anna: special link for you, which has no availability, [01:01:37] Joe: but it’s coming. You’re getting ready, Hannah, to open a spot. I’m sure. Uhhuh. Just keep checking, Doug. Refresh the page. [01:01:43] OG: Yeah. Refresh. It’s like trying to get Ticketmaster tickets to the show. You just, it’s what it feels like. Bam. The refresh button. [01:01:49] Joe: Before you refresh, Doug, what are our big takeaways from today’s episode? [01:01:54] Doug: Well, Joe first take our advice on Roth conversions as you’re plotting when they work. Evaluate your tax situation today and in upcoming years. The idea is to pay as little as possible now to create great tax opportunities down the road. [01:02:10] Doug: Second, HSAs, while they’re very good to pay some bills today, they’re even better if you’re able to let them grow. So your earnings pays lots of bills down the road. But the big lesson, don’t tell Joe’s mom about dart throwing monkeys. She’ll turn that into an insult where the monkey is better than Doug at washing windows. [01:02:31] Doug: I’m gonna show you, mom, I’m way better than monkeys at washing windows and I can take out the trash faster than they can do. Watch this. Damn it. She got me again. Thanks to Anna Allam for joining us today. To find time on Anna’s calendar, go to Stacking Benjamins dot com slash og. And finally, thanks to you for joining us with your questions. [01:02:56] Doug: Have more call us at Stacking Benjamins dot com slash voicemail and be a part of our upcoming show. We’ll also include links in our show notes at Stacking Benjamins dot com. This show is the Property of SP podcasts, llc, copyright 2025, and is created by Joe Saul-Sehy. Joe gets some help from a few of our neighborhood friends. [01:03:19] Doug: You’ll find out about our awesome team at Stacking Benjamins dot com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. Oh yeah, and before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. [01:03:38] 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, Duggan. We’ll see you next time back here at the Stacking Benjamin Show. [01:04:41] Joe: Welcome to the after show. This is the part of the show that doesn’t exist. Anna, if, uh, if you want to talk about the, well, you just don’t talk about the after show. Shut your pie Hole. Wow. Like [01:04:52] Anna: actually, like it’s not, [01:04:53] Joe: we don’t, yeah, we don’t talk about it. What happens to the after show stays in the after show? [01:04:57] Joe: Where have you been? [01:04:57] Doug: We’ve had people listen to this show for years. Who we were like, I just discovered there’s a whole different part of the show. Yeah. [01:05:04] Anna: Oh. But it is like, I’ve heard the after show. I’m like, are you guys Not actually, no. But you have out. [01:05:09] Joe: I don’t think you get it. You haven you haven’t heard yet. [01:05:11] Joe: Fight. Fight Club. Heard. Okay. Yeah. Come on. [01:05:13] Anna: Yes. Oh, this is all new to me, [01:05:14] OG: so it’s so [01:05:15] Anna: exciting. If you wanna [01:05:16] OG: be on the inside circle, you have to. [01:05:18] Anna: I feel like I’m like going into Cigar Lounge or something. [01:05:22] Joe: It’s like fight club. I wanna know, you know the secret knock now? The secret handshake. Yeah. Uh, how long has it been since any view have been? [01:05:28] Joe: We also, generally, if you’re new here, we don’t talk about financial planning in the after show either. So if you’re here for financial advice, see you. We’ll see you next time. Sometimes we do, but not today. This is a financial decision that a company made. When’s the last time? Any of you have been to a Wendy’s? [01:05:42] Joe: Let’s say he’s been to the Wendy’s latest ’cause I went yesterday for the first time in years. Okay. You win. No, no, no. I went [01:05:48] Doug: during this show, Joe. I, [01:05:52] Joe: but that I’m saying among the three of you, I will bet money that Doug has been to a Wendy’s sooner than either Anna or og. Yeah. Doug, when’s the last time you went to Wendy’s? [01:06:05] Doug: Uh, I think it was four days ago. Whoa, Anna, how about you? [01:06:11] Anna: It’s probably been like five years maybe. And really just the frosties, like I don’t really eat the meats there. [01:06:18] OG: Yeah. I’m a, I’m a fan of the square cheeseburger, the double square cheeseburger. I can, they so put down with the best of ’em, but it is a bad [01:06:24] Doug: idea. [01:06:25] Doug: It’s a, listen, it’s a spicy chicken meal deal with no mayo, because I mean, I gotta keep the swimmer’s build somehow, right? Mm-hmm. And then you do the $5 biggie bag on the side. [01:06:36] Anna: The what? [01:06:37] Doug: What is that? A five biggie bag. [01:06:39] Anna: What’s a biggie bag? Oh my God. [01:06:42] Joe: It’s the thing that the person next to the drive through is selling all the kids. [01:06:47] Joe: No, it’s not a [01:06:48] Doug: dime bag. Like here’s the [01:06:50] OG: other meal for the other person in your car, sir. Oh, excuse me. [01:06:53] Doug: It’s the side meal. So it’s appetizer. The Biggie bags have like. And they have a $5. You get a meal before [01:07:00] Joe: your meal? Yeah. [01:07:01] Doug: Like an appetizer meal. Yes. And so it’s a burger. You get nuggets. You get fries and a drink. [01:07:09] Doug: That’s just, but they’re little. So that’s the side meal. Do you start with that? Depends on if I’m feeling frisky or not. Sometimes I just chisel that down before I leave the parking lot. And then, yeah, then I get into, then I get into the spicy chicken meal once I get back on I 75. Okay. [01:07:25] Joe: It’s like a method actor, Anna, [01:07:27] Doug: like he’s got, he’s got, [01:07:29] Joe: he’s got a certain, certain setup. [01:07:31] Joe: Wow. He’s gotta be listening to something specific on the radio at the time. [01:07:36] OG: Set the mood light a candle. [01:07:38] Doug: This is, this is my stop. This is my regular stop in West Branch Michigan. As I’m heading up or down I 75. There’s a Wendy’s there that, uh, counts on me to make their monthly rent. [01:07:51] OG: Doug’s here. [01:07:52] Doug: Woo-hoo. [01:07:53] Doug: We’re hitting our [01:07:53] OG: numbers. It’s like the cartoon where they’re like, and they gotta like pull the lever. You know, all hands on deck [01:08:00] Doug: uga. [01:08:02] OG: Yeah. [01:08:02] Doug: Yes. Well why did you bring this up, Joe? It wasn’t just to expose Mike Ney was and [01:08:07] Joe: scene. [01:08:07] Doug: Yeah. We didn’t even need [01:08:08] Joe: to know what I was gonna talk about. That was good enough for me. [01:08:12] Joe: So they have this tie in with the show that we’ve been watching Wednesday, a Tim Burton show, this is the second season they did that stupid thing Netflix does, where they show you the first half of the season and they take a break. Oh, he’s gotta, yeah. Oh God. Then you gotta wait for a few weeks. I’m like, come on, love is Blind [01:08:27] Doug: does [01:08:27] Joe: that too. [01:08:28] Joe: And [01:08:28] Doug: it just [01:08:28] Joe: pisses me. Mm-hmm. I mean, my [01:08:29] Doug: wife off [01:08:30] Joe: either release ’em all at once or do it the one week at a time. So I just get in a cadence, but don’t let me binge half of it in three days and then wait two months. So now I’m waiting for the second half of, of Wednesday, and I like quirky shows like that. [01:08:44] Joe: But your results with Wednesday may vary. I can see why some people wouldn’t love it much. I don’t think, Doug, you’d like Wednesday that much. Have you watched it? [01:08:51] Doug: Nope. And I saw the previews and I’m like, no, that’s [01:08:54] Joe: not me. Yeah, OG wouldn’t like it. Anna, have you watched Wednesday? [01:08:56] Anna: I haven’t. We’re pretty like knee deep in Miss Rachel Elmo, stuff like that. [01:09:03] Joe: So you gotta build up to it. Yeah, [01:09:05] Anna: yeah. The good thing is they’re on YouTube. You can binge ’em if you want, but yeah, we’re Miss Rachel. We’re just of stuck in that. Have you ever heard of Miss Rachel [01:09:12] OG: Coco Mellon? [01:09:13] Anna: She’s like the icon Louis of Gen A or whatever the young generation is right now. Whatever the [01:09:19] Joe: next, next next gen is. [01:09:20] Joe: Yeah, yeah, [01:09:21] Anna: yeah. [01:09:21] Joe: Hmm. No, never heard of it. [01:09:23] Anna: Oh my gosh. Dog, Wendy. My life revolves around Miss Rachel. [01:09:28] Joe: Wendy’s says a tie with the show Wednesday and they have this whole meal that you can get, but Cheryl had like a sore throat yesterday, so she’s like, you know what? I’d really like a frosty. We pull up and they’re advertising the Raven’s blood, frosty, and so we pull up and Wendy’s has made the great idea. [01:09:49] Joe: To make AI be the person at the drive through. So you’re not talking to a person, you’re talking clearly to ai and you can even see as your order’s appearing on the, the screen, it’s printing out the words that you’re saying. It’s printing out the words it’s telling you back as you order. So Cheryl goes, Raven’s blood frosty. [01:10:07] Joe: Oh, I wonder what that is. So I rolled out my window and it says, can I help you? And I said, yes. What’s a Raven’s blood? Frosty. And the AI answers, it’s the frosty that’s in the Wednesday theme meal, whatever they’re calling it, the meal of whatever. We go, well, what is it? Then it tells me again, it’s the frosty that comes in the meal. [01:10:29] Joe: Have you ever gone up to a, a drive-through and gone? So what is a cheeseburger? Oh, it’s the thing that comes in your meal. Like, that’s the answer that I want. What’s a Coca-Cola? Oh, it’s the drink that comes with your meal. Well, unbelievable. What’s a tota? Beans, meat, and cheese. After, after I argue with it a couple times, this woman comes on and she’s like, it’s a dark cherry, frosty. [01:10:55] Joe: And I turn to Cheryl. She’s like, yeah, get me one of those. Get me a medium. But Cheryl likes chocolate ice cream. And so we pull around and the woman working at the drive-through all of her care had been gone weeks ago. Like she just totally, she literally just takes my credit card and I’m trying to ask her, is this a chocolate? [01:11:16] Joe: Frosty a vanilla frosty, or is it like a cherry ice cream? Like, how does this work? She wouldn’t even look at me, so I could ask the question, and then she opens up the, the door with the credit card and the frosty, and she just hands it to me and I go, Hey, I just have a question. She goes, Uhhuh, hands it to me and slams the door shut. [01:11:36] Joe: Oh, [01:11:37] Anna: no. [01:11:39] Joe: So I don’t know what was worse, the AI or the person, like, which piece of this was, but man, it’s gonna, well, that is not [01:11:46] Doug: the flagship Wendy’s in the chain, is it? Apparently not. Yeah. [01:11:50] OG: I was gonna say, the good news is that at after your seat, there’s the, there’s the thing where she just flips the iPad and goes, it’s gonna ask you a question. [01:11:58] OG: Right? You’re like, I bet it is negative 10%. Yeah. [01:12:02] Joe: I love that one too. It’s gonna ask you a question here, and I don’t have anything to do with it. I have no idea what the question is. It’s a surprise to me. It asked me. [01:12:09] OG: Yeah, it’s just a random question, you know, why is the sky blue? [01:12:13] Joe: Yes. Not that you just washed your own car using the whatever. [01:12:17] Joe: Would you like to give us a tip? [01:12:19] OG: That would be actually a good way to do that. Like if instead of be like a good play on that stupid. That’s right. Stupidity. Like it’s gonna ask you a question and then it’ll say like, you know, why is the sky blue? And give you a couple of answers and if you answer correctly, it’s like, hey, you get 5% off your meal. [01:12:33] OG: Good job. [01:12:34] Joe: So stacker’s, just one more thing. If you could just look at your device, you’re listening to this on the device is gonna ask you a question here. I was gonna ask [01:12:40] opener: you a question real quick at [01:12:41] Joe: the end of the episode.
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