Stop Leaving Money on the Table at Tax Time (SB1798)

Taxes don’t have to feel like something that happens to you.

Joe Saul-Sehy, OG, and Neighbor Doug break down the biggest recent tax changes and, more importantly, how to use them intentionally instead of accidentally leaving money on the table.

This isn’t about memorizing the tax code or becoming a DIY CPA. It’s about understanding where the real opportunities are right now, which moves matter most at different life stages, and how smart planning today can quietly add up to thousands of dollars over time.

From new deductions to retirement-focused strategies, this episode helps you move from reacting at tax time to planning all year long.

What You’ll Learn:

• The most important recent tax changes and who actually benefits from them

• How the expanded SALT deduction works and when it matters

• What the new senior deduction could mean for retirees and near retirees

• Why maximizing retirement accounts isn’t just about saving for later but lowering taxes now

• How Health Savings Accounts create one of the most powerful tax advantages available

• When tax loss harvesting helps and when it’s mostly noise

• Why managing your tax bracket in retirement can be as important as investment returns

• Smarter charitable giving strategies that align generosity with tax efficiency

• How education savings tools fit into a broader tax plan for those who need them

• Common tax season mistakes that quietly cost people money every year

This Episode Is For You If:

• You suspect you’re paying more in taxes than you should

• Tax planning feels overwhelming so you just deal with it in April

• You want to understand which tax moves actually matter at your life stage

• You’re tired of hearing about strategies that don’t apply to your situation

• You’re ready to stop reacting to taxes and start planning for them

This episode is for anyone who wants their tax strategy to support their bigger financial goals, not work against them. If you’re looking to keep more of what you earn and make fewer “wish I’d known that earlier” decisions, this is one to queue up.

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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Our Headline

• Tax Deductions for 2025 That Can Get You a Bigger Refund: SALT, Seniors and More (Wall Street Journal)
• 8 Smart Tax Planning Strategies for Individuals in 2025 (Allied Tax Advisors)

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Doug’s Trivia

• What singer, who recorded hits like “Always On My Mind,” “Whiskey River,” “Bloody Mary Morning,” and “I Gotta Get Drunk,” settled with the IRS in 1992 after the IRS said he owed $16.7 million, and ultimately settled for $9 million?

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Want more than just the show notes? How about our newsletter with STACKS of related, deeper links?

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Other Mentions

• Protect your identity with our newest tool, The Vault

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Join Us Wednesday

Tune in on Wednesday when we’re joined by Whitney Elkins-Hutten, who takes us through her journey from not having much money to wildly affluent.

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Written by: Kevin Bailey

Miss our last show? Listen here: How to Get 1% Better Without Burning Out (SB1797)

Episode transcript

[00:00:00] Joe: It is Monday. My feet are cold, but my, uh, heart is warm because I get to spend time with you two. 

[00:00:06] Doug: God, you’re really bad at lying. 

[00:00:10] Joe: What are you talking about? Lying? This is like a Hallmark movie. We’re beginning February. What’s more romantic than spending a day recording with you guys? Oh, so 

[00:00:21] Doug: nice. Did you just say Fred Brewery?

[00:00:23] Doug: That brewery, 

[00:00:24] Joe: isn’t it? There’s an R in there. A brew. There’s an r. 

[00:00:27] Doug: Come on. You 

[00:00:28] Joe: know what else there is? 

[00:00:29] Doug: There is, but I mean, only weirdos say it. It’s like saying salmon. 

[00:00:34] Joe: I’ve, I, I’ve said that before too. I may have, although I may not remember it. That’s a story for another day. Let’s raise our mugs 

[00:00:42] Doug: raising 

[00:00:43] Joe: because we got some troops.

[00:00:44] Joe: We need to salute, saluting on behalf of the men and women making podcasts in mom’s basement and the men and women. Trying to stack Benjamins. Here’s to all the people that, uh, kept us safe all weekend long. Thank you for all you do. Let’s go stack some Benjamins together now. 

[00:01:01] Doug: Thanks everybody. 

[00:01:02] Joe: Stacky, stacky.

[00:01:04] Doug: Joe. The bottom of your mug is red. Does that mean you’re excited to see me?

[00:01:10] opener: Oh, it’s Monday, baby. It’s Monday, start of the new week. It’s raining outside. It’s cold, it’s gloomy. There’s every reason to not be excited, but guess what, baby? We are excited, we’re motivated, we’re dangerous and disciplined. We have a new week in front of us. A new week to chase after every dream. We want a new week

[00:01:37] Doug: live from Joe’s mom’s basement. It’s the Stacking Benjamin Show.

[00:01:52] Doug: I am Joe’s mom’s neighbor, Duggan. Ah, February. Sorry, February. Quiet candle. It dinners romantic evenings and prepping my taxes. Yes, the good times. So what’s different this year on today’s show, the seven big tax changes that might put a bigger refund in your pocket. What are they? Get your pens ready because we’ll cover every one of them on today’s show.

[00:02:19] Doug: And that’s not all. This is a variety show, ain’t it? I’ll also share a TikTok minute about how to save money while you’re traveling and then I’ll share some twangy trivia. And now two guys who are romantic old softies about money. It’s Joe and oh,

[00:02:43] Joe: hey there, stackers. We are your romantic text prep companions, although you should consult your text advisor even though you listen to the Stacky Benjamin Show. I am Joe Sulci. Hi, happy Monday. We’re super happy that you’re here. Sit back, relax, grab your favorite utensil to take notes. There’s a utensil utensil to take notes since you guys are the 

[00:03:06] OG: No, I think it 

[00:03:06] Joe: utensil the police 

[00:03:07] OG: like your utensil.

[00:03:08] OG: As in, 

[00:03:09] Joe: yeah. 

[00:03:09] OG: Did you put your tinsel on the tree yet? 

[00:03:11] Joe: That’s right. So that your house burns down. How long has it been since they put tinsel on a tree? We used to do that when I was a kid. Did you? 

[00:03:18] OG: Yeah, in-laws. Oh my 

[00:03:19] Doug: gosh. 

[00:03:20] Joe: Wow. That is a blast for in the past, but, uh, we’re not gonna get into that ’cause og It is officially February, it’s officially tax prep season.

[00:03:31] Joe: It’s time for people to go, go, go. I 

[00:03:33] OG: think you’re a few days behind if you’re waiting until the 1st of February 

[00:03:36] Joe: to get going on your taxes. 

[00:03:38] OG: Yeah. Shouldn’t you be rocking and rolling already? Nobody, nobody else has their stuff done. January 2nd, like all lined up in a big pile, like ready to scan this, send to the CPA.

[00:03:48] OG: No. That’s what’s 

[00:03:48] Joe: wrong with you. That’s just me. If you haven’t done that yet, that is, that’s a hundred percent you. I’ve known you for how long? It’s a hundred percent. You, January 2nd. You’re like, let’s go. Come on. 

[00:03:57] OG: Actually, I have changed my opinion about taxes. I used to be the perennial, like extension filer, like, oh, I’ll just extend it.

[00:04:04] OG: And all that happens when you do that is you just extend the pain. First of all, you still have to pay in April and so you have to like kind of do your taxes anyway to get an idea of how much money you’re gonna owe. So you’re like 90% of the way done. And I understand sometimes you can’t, if you have a tax form that doesn’t come until August or something, you gotta wait.

[00:04:19] OG: But for the vast majority of people extending just kicks the can down the road in the sense of like, now you just ruined your summer. 

[00:04:27] opener: Yeah. 

[00:04:27] OG: Because summer’s gonna come and it’s gonna be like, right. The kids gonna start going back to school and you’ll be go, you’re gonna go, oh crap. Myself, do my tax. Oh, frick.

[00:04:36] OG: And now you’re trying to find stuff from 20 months ago to get to your CPA because it’s due on October the 15th if you’re filing your personal returns. So I try very hard to be the first person in the door. So I do, I send all, all the business stuff is already gone, uh, to the CPA the second week of January.

[00:04:55] OG: Like QuickBooks is updated, the banks are reconciled. Start going, 

[00:04:59] Joe: well, that wonderful conversation. We with Hannah Colbeck at the beginning of uh, December og. She even said, if you’re one of the first people there, you get your tax person when they’re fresh. Like if you’re working with a professional, you get them when they’re fresh.

[00:05:12] Joe: You get them when they’re excited. If you’re taking it in their April 8th or April 10th. 

[00:05:19] OG: Well, I mean, the reality is. I mean, look at the industry. There’s not enough people, there’s not enough tax prep people, whether it’s contract workers, you know, during the busy period or just, or CPAs and enrolled agents.

[00:05:30] OG: There’s just not enough of them in the country. So when you get to March or April, you’re, you know, you’re back of the back of the line. Yeah. So I wanna be done. I wanna start that audit clock baby, 

[00:05:41] Joe: get that done, have, have my next 11 months to myself now worrying about my taxes. Love, love 

[00:05:47] OG: that. I know you guys, some people are yelling right now.

[00:05:49] OG: They’re like, 

[00:05:50] bit: but 

[00:05:50] OG: Schwab doesn’t send my 10 90 nines until the middle 

[00:05:53] bit: of February. I can’t. 

[00:05:54] OG: Okay. 

[00:05:54] Joe: Just get the rest of it ready 

[00:05:55] OG: and be done with everything else. Like have it all ready to go. And then when you get the 10 99, put it on the pile. Bang. Done. 

[00:06:02] Joe: I had some other news that came up recently. A HAI got on that text stream where somebody you don’t know, texts you about every other day, ask you how you’re doing or do you wanna meet for coffee or some other phishing scam that ends up with my bank account empty and didn’t actually end up going out for coffee.

[00:06:19] Joe: When I signed up for our new product, the Vault, I was our first user by the way. Immediately I saw exactly what awesome tool this was because it told me, bam, your phone number was lifted off the dark web beginning in mid 2024, and that was the same time that those texts appeared. So I began then very quickly, well, actually I didn’t do anything.

[00:06:39] Joe: The vault started taking me off these lists, 56 of them in my case, but there’s three or four more that it finds all the time. And the cool thing, that’s about one 20th. Of what the vault does. Check it out at Stacking Benjamins dot com slash vault to see how it works. Finally, take control of your subscription management identity protection, getting removed from those trash list and controlling your credit.

[00:07:00] Joe: All of that Stacking Benjamins dot com slash vault. We got a great show today, but we do have a couple more sponsors who keep us keeping on keeping on so that you don’t pay a dime for any of this. Goodness, Doug, as I always say, stacky Benjamin show always free and worth every penny. That’s why we have our sponsors.

[00:07:17] Joe: So let’s hear from them. Was that a giggle? Was that a There it is. That’s 

[00:07:24] Doug: a Pillsbury Doughboy. That’s what I sounded like. Like that 

[00:07:27] Joe: you did. Like somebody punched that just poked a finger right in the stomach. Brown 

[00:07:33] Doug: belly. 

[00:07:33] Joe: We’re gonna hear from them and then we’re diving into helping you maybe keep a few more bucks in your pocket this tax season.

[00:07:48] Joe: The inspiration for today’s discussion comes to us from the Wall Street Journal. This piece was written by Ashley Ebing and Richard Rubin. The new tax rules that can get you a bigger refund this year. There are seven of them, og, so, mm-hmm. Let’s dive into exactly how we can maybe help our stackers keep more money.

[00:08:07] Joe: We’ll, also a link to this, if you have a Wall Street Journal subscription, you missed it. On our show notes page at stack you Benjamins dot com, first of all, the standard deduction, bigger up by 750 bucks. This one’s gonna be easy, og. I mean, your tax software is gonna do this one for you, but the standard deduction up to 15,000, seven 50, that’s a $750 increase from a year ago.

[00:08:30] Joe: So there’s a few dollars. 

[00:08:32] OG: And that’s the single one. 

[00:08:34] Joe: That’s the single standard deduction. 

[00:08:36] OG: Yeah. And the other thing that this helps too, by the way, is it makes it so if you’re, ’cause I think married joint is, I mean, is it double? Is it 31? 

[00:08:43] Joe: Married? Filing jointly for 2025 is 31 5. 

[00:08:47] OG: If you’re not gonna be at the $15,000 level or 30 2K level for married filing joint, it eliminates all the record keeping.

[00:08:57] OG: Don’t worry about it. We’re back to like, well, I gotta get all my stuff ready for taxes. It’s like. There’s not a lot of stuff anymore if you’re not donating a bunch of money, if you don’t have a bunch of mortgage interest, if you don’t have a bunch of property taxes, which are, you know, limited in some places, and that’s one of your, that’s, I bet that’s one of your items on your list here, property tax changes.

[00:09:18] OG: But if you’re not at 30, 32 K, then don’t stress it. You just take the the line item and go. The good news is that the tax software, CPA, TurboTax, whatever, is gonna calculate all that for you anyway. 

[00:09:28] Joe: There truly isn’t much there that you need to do. Like it’s, it’s just gonna, that’s gonna happen now, if you’re 65 and older, you’re also getting 2000 bucks.

[00:09:37] OG: You get a little kick. Yep. Little kicker. 

[00:09:39] Joe: Additional standard deduction. 

[00:09:40] OG: You guys have that to look forward to here shortly. That’s cool. 

[00:09:43] Joe: There’s also the new senior deduction for an additional 6,000 bucks. That’s a big one. That’s gonna last just the next, uh, three years. 

[00:09:50] OG: Mm-hmm. 

[00:09:51] Joe: Let’s talk about the salt deduction because this was a huge difference.

[00:09:55] Joe: It is up to $40,000, which is a $30,000 increase over last year. This is one of the big changes in the big beautiful bill. What is the salt deduction for people that don’t know what that means? 

[00:10:08] OG: Well, until this year, you were limited. And this all goes back to the 2017 tax law change between 2017 and today.

[00:10:18] OG: You are limited in the amount of deduction you could claim for state and local taxes. That’s what SALT stands for. So your property taxes, your state taxes, used to be able to exclude that income basically from your federal tax. Well, because only rich people pay taxes, they limited that to $10,000. Well, that kind of backfired because they went, oh.

[00:10:40] OG: Actually turns out other people pay taxes too, not just the 

[00:10:45] Joe: uber 

[00:10:45] OG: wealthy billionaires and trillionaires that you’re trying to tax into oblivion. So, so they changed it and now you can go up to 40 K, but it’s still limited by income. So there’s an income threshold and it decreases. Um, I don’t have the number off the top of my head and I’m sure it’s in the article, but again, nothing that you have to keep track of.

[00:11:01] OG: ’cause the software, your CP will calculate this for you automatically. But if you’re in that sweet spot of not quite making a bunch of money and still have a lot of taxes due, whether it’s property taxes, you know, real estate taxes, what have you, or uh, state taxes, local taxes, you get a little bit of a benefit there, which paying taxes on taxes kind of suck.

[00:11:22] OG: So I get. 

[00:11:23] Joe: Yeah, that deduction, by the way, those numbers we can just go over that begins to phase out for taxpayers who have a modified adjusted gross income, that’s the income at the bottom of the first page of your tax return. By the way, if you’ve never gone through this, just take out a tax return and read the lines and it’ll start to make sense exactly how this stuff works.

[00:11:43] Joe: But modified adjusted gross income exceeding half a million dollars, or if you’re married, filing separately, 250,000 bucks. Deduction reverts to the previous cap at 10,000 for people with a modified adjusted gross income of 600,000 or more. So for those people, they will, they’ll still see a little more hurt.

[00:12:06] Joe: Brand new one this year, OG Tips, income deduction. Talking to our friend, pt, who is an accountant and also the creator of the FinCon Conference. Saw him at a conference last week and he was talking about the number of creators when he’s doing tax planning. He’s like. Is there an opportunity to get tips?

[00:12:25] Joe: Is there a way for your audience to tip you? Are there a way for people that you work with to tip you? Is, is there a tip? Now you gotta be very careful, like he said, and you don’t wanna classify something as a tip. That’s not a tip, but this is $25,000 is an income deduction if you’re somebody who’s working in the service industry.

[00:12:44] OG: I mean, again, this has to be a beyond reproach here. Ultimately, the tip income has to be from business that is qualified to get tips. You can’t just be like, I am a garbage man and part of my income is tip income. Like nobody tips their garbage people, you know? And so that’s not a thing, and it’s very difficult to reclassify your income as tip income if you’ve already.

[00:13:09] OG: You know, if you don’t have the system set up, if you work in the service business, if you’re a server or you work at a coffee shop, your paycheck already shows that. You know what I mean? Like they already calculate that in there and so it’s easy to, you take advantage of that benefit, but to go back in time and be like, well, actually 25,000 of my income was tip income.

[00:13:28] OG: Probably not super easy. The other thing that I read about this was if it’s a mandatory. Tip, it doesn’t count. So like for example, let’s say that you work at a real fancy restaurant. 

[00:13:40] Doug: I was gonna say, so like every restaurant now. 

[00:13:42] OG: Well, yes, but I was thinking about in the context of like you’ve got an eight person table, you’re at the big fancy steakhouse in town, and they say they added, we automatically include a 20% gratuity on party over six.

[00:13:55] OG: Right? Like that’s very common thing to see. Apparently. That’s what this article said that I read. I didn’t read the tax code. That doesn’t count because that’s not a gratuity, that’s a automatic service charge, basically. So a lot of stuff to still come. Basically, if you don’t work in a TIP business, don’t, no, don’t try to make part of your income tip income.

[00:14:16] OG: And if you do work in a tip business or if you’re the owner of a tip business, you really gotta tread carefully and get some pro help here on how to classify this because it’s not super clear and easy. 

[00:14:26] Joe: PT works with people in the online world and a lot of these people at Patreon, right. Maybe people listen to podcasts where they have a Patreon Yeah.

[00:14:33] Joe: Or something, and he’s, he’s talking to some of these creators about, Hey, is there an opportunity for a Patreon because this is, uh, a, maybe another income stream if you’re somebody that works online. And B, it also is a tax opportunity that might not be here forever. 

[00:14:48] OG: Yeah. Maybe. 

[00:14:49] Joe: Next up overtime, pay deduction, $12,500.

[00:14:52] Joe: Again, work with your tax accountant on this one because a lot of stipulations on overtime pay. You can’t start reclassifying your income is overtime pay, but if it has been historically, there could be a deduction there. Auto loan interest deduction new this year of uh, up to $10,000. Sochi. 

[00:15:12] OG: I mean, have you looked at the price of a new car recently?

[00:15:15] OG: Interestingly, that has not had an effect I don’t think, on car sales from what I’ve seen in terms of manufactured data and, and retail car sales. Nobody’s buying new cars right now. It seems like interest rates suck and apparently people are finally tired of spending $120,000 for an Oldsmobile or whatever the hell you know, cost to buy one 

[00:15:37] Joe: for a smart car.

[00:15:38] OG: One of those things now. 

[00:15:38] Doug: And he calls us old and he is referring to Oldsmobiles 

[00:15:42] OG: fun 

[00:15:42] Doug: fact, which is a make that hasn’t been made. I 

[00:15:44] OG: actually, an Oldsmobile was my first car that I bought myself. 

[00:15:48] Doug: Ah, 

[00:15:48] OG: believe that or not. 

[00:15:49] Joe: What’s the first car you bought yourself, Doug? 

[00:15:51] Doug: Uh, first car I bought myself was a Chrysler Horizon Dodge.

[00:15:56] Doug: Is it a Dodge Horizon? Same vehicle. And, uh, just 10 short days before I paid it off, it was found in a lake. 

[00:16:03] OG: Wow. And no one knows how it got there. 

[00:16:07] Joe: Was found. 

[00:16:09] Doug: No. The crappy thing is I still had to pay it off. It’s not like I did it. Yeah. 

[00:16:13] bit: Okay. 

[00:16:13] Doug: It got stolen and uh, I can’t figure out how the insurance 

[00:16:16] Joe: company found it out there.

[00:16:17] Doug: Are you kidding me? I had public liability, public damage. Only on that car. There was no theft, nothing. That was a total loss for me, 

[00:16:25] Joe: and it was gone. I was a Chevy Monte Carlo. With the ceiling that no longer stuck. You know the ceiling. Oh, 

[00:16:31] Doug: the hood liner. The headliner was 

[00:16:33] Joe: uh, yes. Yeah. All came down. 

[00:16:35] opener: Yeah, 

[00:16:35] Joe: it was good.

[00:16:35] Joe: I tried to put a new radio in that I bought one of these aftermarket stereos ’cause it really didn’t have one. I put it in. I didn’t know what that grounding wire was for. I had no idea. So I got the two hooked up. I, I hit, I hit the ignition, cranked 

[00:16:48] Doug: it 

[00:16:48] Joe: with my hand on the radio, and I just felt this weird buzzing sensation.

[00:16:53] Joe: And then I turned the TV off and it shot me outta the car at the radio like I was, as I found out what the grounding wire was for 

[00:17:00] OG: you were the grounding wire. 

[00:17:01] Joe: I was apparently the grounding wire. Yeah. Uh, little electronics education there as it were. So these different tax rules, if you live in a state with high state or local taxes, obviously I think you wanna look at the salt deduction.

[00:17:17] Joe: If you’re somebody that works where you get a lot of overtime, or you work in a traditionally tip field, you definitely wanna dive into those with your tax team. If you have a. Child, the maximum tax credit went up by 200 bucks. Let’s see what else we got in here. Of course, we mentioned 65 and older. We’ve got the $6,000 deduction for people 65 or older.

[00:17:42] Joe: Uh, we also have. This new car, if you took out a loan to buy a new car as much as $10,000 in interest, which to OG to your point could be one 10th of the interest that you paid on that high interest loan on that? 

[00:17:56] OG: That’s 

[00:17:56] Joe: crazy. Crazy 

[00:17:57] OG: how much these things cost now. 

[00:17:58] Joe: Bajillion dollar car 

[00:17:59] OG: and they’re like unfixable too.

[00:18:01] OG: You know, I’m not handy in any way, shape, or form. Like I could change a tire and I could change oil if I had to. You know, all the technology that we think is super cool in cars makes it. Almost impossible to fix because you need a computer engineering degree. And then on top of it, all these companies are now charging you subscriptions for different things, which is kind of interesting also.

[00:18:21] OG: Oh, did you want heat? You, you wanted the heated seats to work. 

[00:18:23] Doug: Right, right. 

[00:18:24] OG: Oh, that’s $8 a month. It’s like, are you fing kidding me? I dunno. Old man yells at cloud. 

[00:18:31] Joe: Mm-hmm. A friend, a friend of mine yesterday was telling me that their elderly parents just had to replace their furnace that was 46 years old furnace.

[00:18:43] Joe: Amazing. 46 years old. 

[00:18:44] OG: Yeah. They were in for a shock. 

[00:18:47] Joe: It all had this one little part every time that just needed to be replaced, and the furnace person was like, this has been a beautiful machine. Easy to fix. Same problem all the time. Inexpensive part, and now we have to replace it with something that’s a whizzbang thing that’s gonna die in 10 years and it’s gonna cost you 18,000 bucks.

[00:19:07] OG: Yeah, I mean, I just got an email from WiMo, right? The company that does, um. Like the home automation stuff. 

[00:19:14] Joe: Sure. 

[00:19:14] OG: They were bought by Alcon or went the other way anyways. They just were like, oh yeah. All that stuff you have that you bought over the last five or eight years. Yeah. We’re just not, you know, just 

[00:19:24] Joe: doesn’t work.

[00:19:25] OG: Yeah. It’s like, sorry. 

[00:19:28] Joe: Yeah, it’s incredible. 

[00:19:29] OG: Could my light switches still work? No. No. Just buy new stuff. 

[00:19:33] Joe: Yeah, duh. Just go buy it again. Uh, we will link to this in our show notes page at stacky Benjamins dot com. In the second half of today’s show, we are gonna dive into another piece that talked about all the different tax things that you should be looking at, or at least eight.

[00:19:50] Joe: Other smart tax moves that you should look at any year, 2025, or any year. We’ll dive into those. We also have our TikTok minute, but first we’re gonna talk taxes. When we talk about today’s date in history. Doug, some guy a few years ago, had a little tough time with taxes. Well actually. I think, uh, m maybe started to solve the problem.

[00:20:10] Doug: Uh, well, let’s just see where this takes us, Joe. Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and let’s talk IRS because it was on today’s date back in 1992, that one country music and hall of fame recording artist settled with the IRS over his tax bill. The IRS said he owed $16.7 million in unfiled taxes, seizing his bank accounts and pad locking his properties.

[00:20:35] Doug: What singer? Who recorded hits like always on my mind? Whiskey River, bloody Mary Morning, and my personal favorite, I gotta get drunk. Settled with the IRS for 9 million bucks. I’ll share his name and more of the story as soon as I make sure I go hide my wallet from Joe’s mom. That woman likes to levy taxes when you’re not looking.

[00:21:05] Doug: Hey there, stackers. I’m on time taxpayer as far as you know, and guy who wants the IRS to know just how little money I make. Joe’s mom’s neighbor, Doug, today we’re shining the spotlight on a singer who owed the IRS, according to them, over $16 million. Of course, according to OG, I always owe him 20 bucks.

[00:21:26] Doug: So you know how that feels. The singer blamed his accountants Price Waterhouse for setting up all kinds of tax shelters and I guess the IRS didn’t think we’re all that shelter ’cause they sure found him pretty easily. He released an album in 1992 to try and help his situation called the IRS tapes, who will Buy My Memories, which included outtakes, bloopers, and lots of glimpses into the creative process.

[00:21:50] Doug: So who was the singer songwriter now in the Rock and Roll Hall of Fame? Of course, it’s Willie Nelson. And now here comes the Poncho and Lefty podcasting. Joe and og, 

[00:22:03] Joe: all the Federally say, could have had him any day. Love that song. Og You Big Willie Nelson fan? 

[00:22:11] OG: Uh, I mean not, no, I wouldn’t, I wouldn’t say a big, 

[00:22:15] Joe: but it’s like you can’t not be a casual fan like you’re a Willie Nelson song.

[00:22:18] Joe: You’re like, oh, that’s good. I’m like you. I’m like, yeah, I’m not a big fan, but still. 

[00:22:22] OG: Right. Seems like a cool dude to hang out with. 

[00:22:24] Joe: I think he would be. He’s always baking something. 

[00:22:29] Doug: Mm. 

[00:22:31] Joe: Maybe himself, you know, he ended up, uh, suing his accountants, uh, for $45 million saying that, uh. He didn’t know how this stuff worked and Price Waterhouse came back goes, dude, you were in all the meetings.

[00:22:44] Joe: Like you knew exactly what we were setting up. Don’t say that you’re not. 

[00:22:49] Doug: Ignorance is not a defense. 

[00:22:50] Joe: Yeah, they eventually settled outta court and everything was private. You have no idea how that ended, but, 

[00:22:55] Doug: but he got like a 45% discount with the IRS when he settled there. So that sounds like a strategy.

[00:23:02] Joe: Even more than that, because I think they originally thought Doug, they originally thought he owed way more than that, uh, $16 million. They were going after him for, like, originally they said he owed like, I think 28 million. So just a huge, huge discount. 

[00:23:16] Doug: Wow. 

[00:23:17] Joe: So there’s your lesson. Just cut another album to help pay your taxes, sue your accountant, and life is good.

[00:23:24] Joe: That’s maybe not the lesson that we, that we need from that. Hey, time for our TikTok Minute. This is the part of the show where we shine a light on a TikTok creator who’s either doing something brilliant or air quotes brilliant stacker. Jen sent this one in. Jen was wondering the same for us as what we’re gonna hear in this video, guys.

[00:23:43] Joe: How much money do you think, uh, comedian, neighbor Gatsy has made? Now speaking of Willie Nelson, most people in Dallas, you know, to have somebody who will fill that big arena, what’s the big arena where the stars play? OG and the Mavericks? 

[00:23:58] OG: American Airlines. 

[00:23:58] Joe: American Airlines Arena, like filling that up one night is yeah, an incredible feat.

[00:24:05] Joe: Nate Ga sold out three shows. Three, yeah, that’s like sold out. Incredible one and had to add another one and add another one. Three shows for this comedian. Dude’s rolling in money. 

[00:24:14] Doug: He’s got a little extra in his checking account these days, 

[00:24:17] Joe: so he’s super wealthy and obviously becoming very popular very quickly.

[00:24:21] Joe: If you haven’t heard him, the dude’s really funny. Dusty Slay a funny comedian, but I bet 90% of our audience doesn’t know who he is, but still very funny. And then two other comedians, Aaron Weber and Brian Bates, they’ve been doing a podcast together and they were doing a live show and they took questions from the audience.

[00:24:37] Joe: And, uh, well, Jen wants to know the same for us as what they ask Nate Per gatsy, dusty, slay, and the rest of these comedians. 

[00:24:47] TikTok: How about you guys are all on the road together? There’s only two hotel rooms available. Who’s rooming with whom? 

[00:24:55] bit: I’ll, oh man. I think Nate’s got 

[00:25:00] OG: his own room. 

[00:25:01] bit: That’s exactly,

[00:25:07] bit: I. And I guess I sleep in the middle. ’cause you need the plugs for the cpa, 

[00:25:16] Joe: the other three in one bed. And Dusty says I’ll sleep in the middle ’cause the other two need the plugs for the CAP machines for them. 

[00:25:21] Doug: Joe, if it’s us on the road, I’ll just say right now, um, you and I are bunking together.

[00:25:27] Doug: Absolutely. 

[00:25:28] Joe: I think we vote for OG to have his own room. 

[00:25:30] Doug: Yeah. 

[00:25:32] Joe: Jen, to answer your question, all three of us vote OG gets the room. 

[00:25:37] OG: I would rather. Sit in a hotel lobby and drink coffee all day, all night. Like stay up all night and just play on my phone. Then share a room with another human being, and not even my kids.

[00:25:50] OG: Nope. Like if there’s only money for one hotel, I’ll sleep in the car. It’s not happening ever. 

[00:25:56] Joe: It is. Well, Doug, because I’ve been in a hotel with OG before and I walk downstairs and here is OG at like four o’clock in the morning and I’m like, what’s going on? He’s like, there’s this woman up there, Mrs. Og, that’s making me share a room with her and I refuse.

[00:26:11] OG: No, she’s, she’s fine, obviously. But um, I remember one time. I, my afterschool activity that I was doing, and we had to stay the night and my, the guy that I traveled with was like, Hey, we should just drive back. And I’m like, no, it’s kinda long. I’m gonna stay the 19th. And I could tell he was just kinda like, I don’t know that I wanna spend the money to, you know, it’s a commitment and that’s cool.

[00:26:36] OG: Like I get that. And so I was like, listen, I have enough Marriott points, not a flex. Just I have enough to get us a room at the. Fairfield, you know, it’s like they’re like 17,000 points, so that’s totally fine. And he is like, okay, cool. Like that works for me. And so we walk in there and I’m like, check it in.

[00:26:53] OG: And I’m like, and then he needs his key too, and she pulls up, she’s like, okay, here’s your key. And we walk up to the third floor and I’m like, all right, this is me. And he’s like. What do you mean? I was like, yeah, you’re like two rooms down, bro. It’s like, did you buy me my own room? I’m like, yes, I am not gonna stay in another room with another human being.

[00:27:14] Doug: It is worth 

[00:27:14] OG: the money. Would rather have fewer Marriott points. 

[00:27:18] Doug: When we went skiing and the fin turn came, we got a place that had like two separate, it was like a condo, you know, two separate bedrooms and a central living area. Thank God separating the two bedrooms. ’cause I heard noises, Joe. I don’t know what goes on in there, but there I did.

[00:27:34] Doug: I’m glad. I think I know he, why he wants to be by himself because things happen in that room over, it’s like an exorcism. 

[00:27:41] OG: It reminds me of that joke. 

[00:27:42] Doug: Yeah, it is. It’s like Linda Blair. 

[00:27:45] OG: What do you mean an exorcism? That’s a joke. It’s not an APR Gazi joke, but it’s a joke. 

[00:27:51] Joe: That’s another day. Or we, we, we can’t share that one.

[00:27:54] OG: Oh, I’ll tell you guys, I’ll tell it later. 

[00:27:55] Joe: Okay. All right. Uh, ti time to move. Thanks, Jen for that TikTok minute. Yes, OG gets its own room and, uh, I think we all agree exactly. I, it was very easy for us to figure that one out. 

[00:28:07] Doug: Oh, yeah. No. Thinking. 

[00:28:09] Joe: Let’s dive back into tax planning. I. For this beautiful Monday because this, uh, other piece from Ally text.com that we’ll link to in the show notes has eight areas of your life that you should really look at in any given year to have a better tax strategy.

[00:28:26] Joe: Number one is og, and this is huge. Just retirement account maximization. Make sure that you’re just maxing out your retirement. You want a tax break and you want a better retirement. Max out those retirement accounts. 

[00:28:38] OG: At least to the employer match contribution, right? If your employer does, you know, a 50 cent match on the first 6%, you gotta be doing six.

[00:28:46] OG: ’cause it’s a free 3%. It’s a, it’s a free 50% return on your, in your money. So absolutely have to take advantage of that. And then, um, I’m a big fan of contributing as much as you possibly can for no other reason than outta sight outta mind. You know, like if you make a hundred thousand dollars and you can save 24,500 this year in your 401k, whether it’s pre-tax or Roth immaterial, you know, and live on the rest and you know, do that.

[00:29:13] OG: When you make $200,000, it’s still only 24,000 and you make 300,000. It’s only 24,000. The sooner you get to the max, the sooner you can go like, okay, that box is checked. I don’t have to do that one ever again. Like easy. You know, it’s not easy. 

[00:29:27] Joe: Yeah. 

[00:29:28] OG: Get there. 

[00:29:28] Joe: Well, and I like a suggestion here. ’cause you know the strategy is, well I can’t afford to do that right now, or I can’t afford to put the max in.

[00:29:36] Joe: When you get a raise, if you get a raise in 2026, pay yourself first with that raise. Like do the bump with the raise to help yourself get there. Like you get new income. Second on their list. Get into tax loss harvesting. Now, I often see people in their twenties, you know, really excited about tax loss harvesting.

[00:29:56] Joe: These aren’t the people that really need to do it. It truly is. If you’ve got money in brokerage accounts, take advantage of this idea of tax loss harvesting. How do you do that og? 

[00:30:08] OG: I’m with you. I think that this is a big headline that has very little impact for the vast majority of people. The only thing that I would really pay attention to is if you have crypto, there’s no wash sale rules in crypto right now.

[00:30:22] OG: Let’s say that you’re, you know, you go, Hey, I wanna buy, you know, a thousand bucks a Bitcoin, and, and a week later it’s down to like $700, right? Because that can happen, right? I would sell that that day and rebuy it that minute. Because you get to write off that $300 loss and then you reset your cost basis back to 700.

[00:30:44] OG: The downside of doing it with little dollars is the transaction costs, and that may or may not be worth it, but capital gains losses are only beneficial to offset other gains or other capital gains of something down the line. So. If you’re like, I’m gonna tax loss harvest this $8,000 of this mutual fund that I lost money on, and then I’m gonna turn around and do like, okay, cool, but, but for what?

[00:31:10] OG: Like if it’s just a line item on your tax, like you can only deduct 3000 a year above your gains. It’s not zero, but it’s not a lot either. So this is a maybe for me. 

[00:31:24] Joe: Third on the list is, uh, health savings account. Triple tax advantage. If you’ve got a health savings account available. This, uh, I think after you get past the match in your 401k could be the number one place to put money.

[00:31:37] Joe: ’cause you can use it later on for retirement if you want to and get very similar tax advantage for retirement, but you also have it available for healthcare. Like, I don’t know, I think the HSA is the way to go if you’ve got one available. 

[00:31:48] OG: HSAs are great. You gotta be careful of, uh, how much cash your HSA requires you to have in the cash portion.

[00:31:54] OG: You could spend an entire year contributing to an HSA and never get to invest a dollar because your company. Good point. You know, the HSA company mandates a certain amount of cash. You know, there’s, again, balancing ACT tier is at worth hanging on to all these receipts and record keeping for two decades to get the tax free age 65 thing?

[00:32:12] OG: Or is it just better to use some of it as you go? Well, what we do, honestly, is we have, you know, we’re like old now, so we have prescriptions, right, that show up every quarter. Like, you know, you gotta take this medicine now. It’s just part of the deal. So I just used the debit card of the HSA to be the payment method for.

[00:32:33] OG: Automated prescriptions, or if I have a copay, that’s the card that’s on file at the doctors, you know, nets out net positive because I don’t spend as much on healthcare as I do going into the HSA every year, which is great. So I’m, you know, net adding to the HSA, but it also removes it for me from like having to keep track of all that stuff year after year.

[00:32:54] OG: It’s just. It’s kind of a use some now and save some later strategy for us. 

[00:32:59] Joe: Yeah. I remember my friend Belinda Rosenblum from Own Your money.com, who works with entrepreneurs on their tech systems and setting up better automation, and I remember her talking about the HSA with a OG and going, you know what?

[00:33:12] Joe: It is great if you can keep those receipts for three decades, but don’t let good be the enemy of perfect. If you’re somebody who just has an HSA and you’re using it tax free to pay for your stuff now. It’s still beautiful, like it still is a fantastic opportunity for you. So don’t get all worked up about, oh my God, I’m not, you know?

[00:33:30] OG: Yeah. If you have a few years where you don’t have a lot of expenses, I mean that money will pile up. It’s what, $8,500 now is the limit. So, you know, if you have five out of 10 years where you don’t really use it or use very little of, it could easily have 50, $80,000 in an HSA, and now your HSA is gonna make as much money invested as you contribute.

[00:33:51] OG: So you get to kind of that break even point where it’s gonna start snowballing on top of itself. So I think it’s great to use for a little bit of now money and. And potentially future money. 

[00:34:01] Joe: The next several get a little more granular. Now. I think those first few are pretty widespread, but for people that are in retirement, especially strategic tax bracket management, meaning looking at those different pots of money.

[00:34:16] Joe: If you’re not in retirement yet, making sure you got enough money in the Roth or money that comes out. Tax free bucket from the top of your tax triangle. Enough money that’s flexible, and of course deciding when and how to take money outta that pre-tax. Strategically. Thinking about that a little bit I think can go a long way thinking about it a lot.

[00:34:37] OG: Yeah, I mean, all of the decisions that you make when you get toward retirement are all gonna have secondary effects. Also, things like Medicare premiums and. The RMD requirements in the future and that sort of thing. So paying attention to it. I think when you’re early on, making sure that you just have some flexibility.

[00:34:55] OG: Should I do pre-tax or Roth? Yeah, I don’t know. Whatever you want. I mean, there’s. An argument on either side of that, but I think you better get to retirement with a bunch of money in pre-tax, a bunch of money in tax free and a bunch of money in brokerage. Your definition of bunch is subject to interpretation, just so that you’ve got the flexibility to say, okay, this year I need X dollars.

[00:35:16] OG: I know this much is coming from social security. You know, like, how can I manipulate the other three buckets to get the income stream that I need at the lowest possible? Cost basically. 

[00:35:28] Joe: You know, it’s funny, Doug, for several years we talked about the dumbest discussion in personal finance was the whole share checkbook.

[00:35:37] Joe: Thing. 

[00:35:38] Doug: Oh yeah. 

[00:35:38] Joe: Do I share a checkbook? And you just poking your eye out like, oh God, we’re having this discussion again. Yeah. I think the Roth versus pretax, you know, lately we’ve got some people coming out going, no, you should definitely do pretax because of blah, blah, blah, blah, blah. Mm-hmm. And then are people going, no, you should do all Roth because of blah, blah, blah, blah, blah.

[00:35:54] Joe: I think this is an idiotic argument ’cause we don’t know where tax brackets are gonna go. So why would you optimize for something that we don’t know versus give yourself the flexibility to go wherever the hell the river moves. 

[00:36:04] Doug: Oh, you think it’s dumb because there’s an obvious answer? 

[00:36:07] OG: No, there’s 

[00:36:08] Joe: no obvious answer I think because there is no obvious answer.

[00:36:11] Doug: Okay. ‘

[00:36:11] Joe: cause everybody’s solving for something that we don’t know. We don’t know where tax brackets are gonna go. So we don’t know if taking all pre-tax today is the best decision. We also, oh, I see, know where tax brackets are gonna go. So we don’t 

[00:36:24] Doug: those. So today might not be the best ’cause other people on that argument have said, do it now, because it could get, I mean, essentially what they’re saying is do it now because it could get worse.

[00:36:32] Doug: It’s the devil we know right now. So take the bullet now. That’s where I thought you were going with that. 

[00:36:38] Joe: Well, people say take the bullet now because your tax bracket is gonna be higher today than it will ever be if you’re in your prime working years. So go ahead and take the pre-tax today to take the biggest tax break that you can get right now ’cause you’re gonna pay less tax.

[00:36:53] Joe: When you’re in retirement. 

[00:36:55] Doug: All right, 

[00:36:55] Joe: well, that’s a false thing because, or your, your money 

[00:36:57] OG: compounds into infinity and you’re 80 years old with $13 million in an ira, and I would argue that might be the richest you ever are in your life at that point. 

[00:37:07] Joe: Yeah. We just, we just don’t know. Give yourself flexibility.

[00:37:11] Joe: Stack your Benjamins dot com slash tax triangle. If you’re lost on what the hell we’re even talking about. But staying flexible really gets you where you want to go. Uh, number five on here. I won’t spend a lot of time on charitable tax giving strategies. Oh gee, 

[00:37:24] OG: well, there’s been some changes to that this year for 2026, the amount of money that you, I’m gonna screw this up ’cause I’m doing it off of memory here.

[00:37:32] OG: But it’s like the amount of your income, the first 1% of that that you give away isn’t counted. From a tax standpoint. So if you make 200,000 and you give 2000 to charity, you don’t get to write off the 2000. Somebody’s gonna write in and go, that’s not it. I, I, something like that. All that to say that it matters, right 

[00:37:53] Joe: here it is.

[00:37:53] Joe: It is a half percent 

[00:37:55] OG: okay 

[00:37:55] Joe: floor starting in 2026, individual taxpayers will only be able to claim a charitable deduction if their contributions exceed half a percent of their adjusted gross income. This means smaller donations may no longer provide a tax benefit unless they’re combined or strategically timed.

[00:38:12] Joe: There’s also a 35% cap on itemized deductions for high income individuals. Total itemized deductions, including charitable contributions capped at 35% of your adjusted gross income. 

[00:38:23] OG: So it may make sense to skip giving this year to give it all in, you know, another year. Give twice as much this year, skip a year.

[00:38:32] OG: Or if you don’t care about that, or if you’re one of the people that you’re just taking the standard deduction anyway, then. Much to do about nothing. 

[00:38:39] Joe: If you are in a state that has a state income tax using 5 29 education savings plan optimization, they work through an example of this couple in a state with tax deduction.

[00:38:52] Joe: A couple in a state with a tax deduction contributes $10,000 to a 5 29 plan for their college. They immediately save 500 bucks on their state taxes, assuming a 5% rate. That $10,000 grows to 25,000 over 15 years. When their child attends college, the entire 25,000 could be withdrawn, of course, tax free. It would’ve had some capital gains taxes if they had not put it in the 5 29 plan.

[00:39:13] Joe: So using 5 29 plans for college, a good idea. Number seven, income, timing and deferral strategies. I think we already got into that. And then, uh, number eight, asset location optimization, meaning having your funds OG that have. High dividends, maybe mutual funds with lots of manager movement inside where they’re buying and selling and there’s capital gains, taxes being created.

[00:39:39] Joe: Even though you didn’t move, your fund manager did. So you get a bill. Putting all that stuff inside your tax shelter and then having the more tax efficient stuff outside your tax shelter can really work on your behalf. We’ll link to these in our show notes page at stacky Benjamins dot com. Guys, let’s uh, wander out on the back porch.

[00:39:59] Joe: It is, uh, super Bowl week, and we’ll get into that in a second before you get to the Super Bowl. Uh, stacker Scott. 

[00:40:04] Doug: Yeah, I mean, he noticed something is really like this was the breaking point for him. All he wants to do is go out to the movies, right? Yeah. With his partner. He just wants to go a couple of tickets to the movies.

[00:40:15] Doug: Talk about sticker shock. $2. Yeah. $287 and 97 cents. Go movies. Two of them to go to the movies and he’s a member of that. It’s like the club, the a MC. Club. There’s more to 

[00:40:27] OG: that story, 

[00:40:28] Joe: Stu. No, hold on. Wait. 

[00:40:31] Doug: Okay. So I’ll take you through it. I mean, it’s a couple of tickets and even he was in that discount club from a MC called Stubbs and even the discount didn’t help that out.

[00:40:39] Doug: So a couple of tickets, some large popcorn. Yeah. How much were the tickets? Large fountain drinks. How 

[00:40:43] Joe: much were the tickets? 

[00:40:44] Doug: Tickets were, looks like about 16 bucks a piece. 

[00:40:47] Joe: 16 bucks each. Does go see a movie. 30, 32 bucks 

[00:40:50] Doug: already. That’s a lot of money right there. Yeah. Uh, large popcorn fountain drink and some hot dogs.

[00:40:56] Doug: 200 and almost 290 bucks for the two of them. 

[00:40:59] Joe: How much was the popcorn? 

[00:41:01] Doug: Uh, 10 bucks. 

[00:41:02] Joe: Yeah. Yeah. Still way overpriced. But anyway, and, and the drink? 

[00:41:05] Doug: Drink was seven 50. 

[00:41:07] Joe: Yeah. And how much were the hot dogs? 

[00:41:09] Doug: Um, hot dogs, well, they were. I’m not sure what the line, I could do the math, but it does appear that, um, one of them was pretty hungry.

[00:41:18] Doug: There were 28 hot dogs, 

[00:41:20] Joe: 20 only 28 hot dogs. I mean, you go to the movie og, the movie theater and you have 28 hot dogs. 

[00:41:25] Doug: Yeah, 28 hot dogs, uh, for $223 and 72 cents. This still seems like price gouging to me. 28 hot dogs is normal. Who doesn’t eat dogs? Who doesn’t hot dogs Go 

to 

[00:41:36] Joe: movie theater. Who among us, throw the first stone, cast the first stone.

[00:41:40] Joe: If you don’t go to a movie theater and have 28 hot dogs while you’re watching your movie, 

[00:41:44] Doug: sir. $8 Hotdogs. 

[00:41:46] OG: What’s your take on the, uh, delivery to your seat 

[00:41:51] Doug: at a movie theater? 

[00:41:52] Joe: We don’t have that theater in Texa. 

[00:41:54] OG: Oh, really? Oh, it, that’s only what we have. I haven’t been in movies in a long time, but that’s, that’s only what we have.

[00:42:00] OG: I was reading something the other day that said, um. Somebody like Matt Damon or somebody who was like, they absolutely hate that, right? Like it’s, yeah, you’re meant to like, lock yourself in a room and focus all your attention on, on this artwork that they just did basically. Right? Instead, you’re like pressing buttons and playing on your phone and like, oh, I, anybody need more, some more hot dogs?

[00:42:21] OG: Okay, cool. I’m gonna order four more hot dogs. And then, you know, the guy comes in like a waiter and Yeah. You know, and kind of in everybody’s way. And I’m kind of there like, we don’t need like. Couches to lie on. 

[00:42:32] Doug: Yeah. 

[00:42:32] Joe: I haven’t been to an Alamo draft house in a while, but when I went 

[00:42:36] OG: Aren’t they all closed?

[00:42:38] OG: They, I think they filed bankruptcy. I 

[00:42:39] Doug: think they might have filed 

[00:42:40] OG: bankruptcy. 

[00:42:41] Joe: Yeah. Oh no. Oh 

[00:42:42] OG: no. Oh yeah. The guy was a piece of crap. I think you like embezzled a bunch 

[00:42:45] Joe: of money. Sony you mean Sony? Because Sony purchased it along time ago, like Sony. Oh, really? 

[00:42:50] OG: Okay. I’m thinking of a different company that, my bad.

[00:42:52] OG: Also Sony’s a piece of crap, so whatever. 

[00:42:54] Joe: Yeah, right. Uh, Sony, uh, send your hate mail to og. 

[00:42:58] OG: We’re not a piece of crap. 

[00:43:00] Joe: Alamo Drafthouse used to do that really well. Used to actually do it where they would, I don’t know, kind of sneak in underneath 

[00:43:08] OG: and, but it’s, it’s already nasty. Like when your, the floor’s all sticky and 

[00:43:12] Joe: not at the draft house.

[00:43:13] Joe: That was a, that was a nice place back when it was Pres, Sony, like it was good stuff. I used to love going to that theater. It was a totally different experience than going to our local cinema. It’s 

[00:43:24] OG: like a drive-in movie. Yeah. 

[00:43:25] Doug: How much were the 28 hotdogs there? 

[00:43:28] Joe: Probably have 11 gajillion bucks, but they had real butter for the popcorn.

[00:43:33] Joe: I did appreciate that. 

[00:43:34] OG: Artisan Pizzas and stuff. It’s like, come on, 

[00:43:36] Joe: so, so, so good 

[00:43:37] OG: in a box of Juju bees and 

[00:43:39] Joe: yes, that was fun Scott, by the way. Thanks for posting that in the basement. 

[00:43:44] Doug: There’s also some fun coming up in about a week, a week from yesterday, the big game Super Bowl is, is about to happen in which, uh, new England host of a fine.

[00:43:56] Doug: Benjamins after dark group will be beating the Seattle Seahawks by score 28 to 24. You 

[00:44:03] Joe: threw down the gauntlet right there. 

[00:44:05] Doug: Yeah. I mean it’s, I’m just spitting facts. I mean, I love the Sam Donald story. It’s inspiring. But Drake May is a beast and uh, they’re gonna pull it off. It’s 

[00:44:12] OG: a beast that scored what?

[00:44:14] OG: 10 points or 14 points in the final two games. 

[00:44:18] Doug: He’s just a winner. The guy just wins. 

[00:44:20] OG: Okay. 

[00:44:20] Doug: Plus he’s, you know, he’s 

[00:44:21] OG: been with his against a second string quarterback that hadn’t started in five years, but Sure. Yeah. Wow. They really took it to those Broncos. 10 to seven. Woo. I 

[00:44:29] Joe: like this. Even on the episode, we’re getting a little heat 

[00:44:32] Doug: back and forth.

[00:44:33] Doug: Yeah. So we’ve got a Boston. Benjamin’s after dark group. We got a Seattle Benjamin’s after dark group. Those two teams are in the Super Bowl. You do the math, look Tucson. If you wanna have a team in the Super Bowl, start your damn group. 

[00:44:46] Joe: That’s all you gotta do. 

[00:44:47] Doug: Yeah. 

[00:44:48] Joe: We’re actually having our meeting with, uh, Tucson.

[00:44:50] Joe: That’s pretty exciting. Uh, hopefully getting that rolling. And by the way, if you’re in Boston, you’re like, wait a minute. We, we, we don’t have a group yet. Yes, we do. We just have not had a meeting yet. So the group is active online, put in, uh, Stacking Benjamins, Boston, and you will see the group get in. And when that first meeting happens, it’s right around the corner.

[00:45:11] Joe: Doug, and you’ve already seen in the basement, they’re starting to throw barbs at each other. The Seattle group founders 

[00:45:17] Doug: Nice. 

[00:45:18] Joe: And the Boston Group founders. Nice. 

[00:45:20] Doug: I really thought we did have a group in Boston already, because I remember talking about a meeting and I even talked about that. It was right next to the donkeys.

[00:45:28] Joe: We’ve had meetups there when I’ve come to town, but we have not had a a monthly meetup group. We do have one. It is founded. It is rolling. 

[00:45:36] Doug: Nice. 

[00:45:36] Joe: We just have not had our inaugural meeting yet, so Seattle often rocking with our buddies. Uh, Chris and Cole out there in Seattle. If you’re in Seattle and you’re not gonna those meetings, what are you waiting for?

[00:45:45] Joe: Oh, also, by the way, we figured out where our meetup is gonna be in Seattle. When I come out there for meet retirement conference guys, we will be on Thursday. March 5th, six 30 in Capitol Hill at Ian Brewing. We’ve had a meetup there before. Great, great time at Ian Brewing in, uh, Capitol Hill, uh, neighborhood of Seattle.

[00:46:09] Joe: So come join us, Seattle Stackers. We’ll be there at six 30, having some fun Thursday, March 5th. Head to Stacking Benjamins dot com slash meetup to sign up for that. Love to see you guys while we’re there. That’s gonna just about do it today. We got a couple more resources. Number one is. If all this tax stuff is really got you down and you’re like, I don’t even know where to begin.

[00:46:33] Joe: We have a tax guide, we have a series of guides, but our tax guide is fantastic. We update it every month. Stack your Benjamins dot com slash guide. But number two, we talked about tax planning. If you’re somebody that’s like, well, wait a minute, I just need a better team than I have today. Not tax pros, but financial planning pros that help you put the puzzle together so that when you go to your tax team, you already have all the pieces in the right place while G and his team are taking clients head to stack your Benjamins dot com slash og and he and Anna and the rest of the team happy to talk to you about how they can help you make better.

[00:47:11] Joe: Financial planning decisions, which include tax decisions in 2026 and beyond. Alright, those are a couple of cool resources we got, but the last resource we always point to before we say goodbye is Doug telling us what the big three things are. That should be on our to-do list this week. 

[00:47:27] Doug: Oh, I’ll tell you, Joe first, take some advice from our headline.

[00:47:30] Doug: Taxes are always changing and so is your personal situation, so take another look at your taxes and let’s keep some money in your pocket. Second. Gotta make a tough hotel room decision. Here’s one that’s not tough. Let OG sleep by himself. Everyone will be happier, trust me. But the big lesson, don’t tell Joe’s mom accountant jokes.

[00:47:52] Doug: She’s got no sense of humor. Listen to these hum dingers. What kind of humor does an accountant have? The self dere kind, uhhuh uhhuh? 

[00:48:03] OG: Nope. 

[00:48:04] Doug: Yep. 

[00:48:05] OG: That’s not the joke. 

[00:48:05] Doug: She didn’t like this one either, but it’s amazing. Where do homeless accountants live in tax shelters? Doug, right? 

[00:48:14] OG: Yeah. The first one was not self-deprecating, Doug self depreciating.

[00:48:18] OG: It’s gotta be self depreciating, 

[00:48:21] Doug: but they both mean going down. 

[00:48:24] Joe: I think it was self depreciating. 

[00:48:26] OG: The joke has to be self depreciating. 

[00:48:29] Joe: I like how Doug’s telling the joke. Can’t figure out why mom doesn’t laugh. 

[00:48:35] Doug: Okay. Whatever. We can analyze these later. Those are hilarious. I think we can all agree. They’re just hilarious.

[00:48:41] Doug: Of course. I’ve always thought there were three types of accountants, those who can count and those who can’t looking for better tax help. How come I didn’t get the laugh track on that one? 

[00:48:54] Joe: Do you got the crickets track, OG quick, 

[00:48:58] Doug: agree to disagree. 

[00:48:59] Joe: You got it. 

[00:49:00] Doug: Looking for better tax help. Check out our tax guide.

[00:49:04] Doug: We update it every month so that you’ve always got the latest intel. In your pocket, and we include a tax checklist at the top, so you know right where to look for opportunities. Find it at Stacking Benjamins dot com slash guides. This show is the property of SP podcast LLC, copyright 2026, and is created by Joe Saul-Sehy.

[00:49:25] 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 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.

[00:49:44] 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 Benjamin Show.

[00:50:49] OG: I’m pretty sure you guys have heard this before, almost positive that I’ve told you, but there was a young boy in a village many years ago and he had a stutter and uh, Doug already knows it. 

[00:51:01] Doug: This is so good. Please tell it. 

[00:51:03] OG: You don’t know this one, Joe? I don’t. He had a stutter. 

[00:51:05] Joe: I had a stutter though. I was a 

[00:51:06] OG: young boy.

[00:51:06] OG: Enough Village was. It’s kind of like you. And he was asking his parents and, and his parents said, we’re gonna have the, the healing man. The shaman come and he performed all these dances and blessed him with the water and, you know, all that sort of stuff. And, um, stowed the stutter, you know. So then they get the priest to come out and the priest performs an exorcism still to stutter.

[00:51:30] OG: And then somebody in the village said, we could, we could try the prostitute. So the prostitute comes and says, you know what’s going on? And says, I have a son has a stutter, and they’re talking and she says, I’m gonna suck the stutter right out of you. And he goes, oh, like an exorcism.