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

Summary

The Stacking Benjamins Show

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

Date: February 2, 2026
Hosts: Joe Saul-Sehy, OG, Doug

Episode Overview

This lighthearted but informative episode of The Stacking Benjamins Show dives into the essential tax changes for 2026 that could mean more money back for listeners at tax time. Joe, OG, and Doug discuss seven new tax rules (primarily highlighted in a recent Wall Street Journal article), offer practical tax planning tips, and keep the conversation entertaining with trivia, personal stories, and their signature banter—all aimed at helping listeners "stack more Benjamins."
Tone: Friendly, playful, jargon-light, educational.

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Key Discussion Points and Insights

1. Tax Season Philosophy & Prep Mindset

• Start Early: OG stresses being ahead on tax prep to reduce stress and avoid last minute filings, noting the limited availability of CPAs come March and April.
  • Quote: "You still have to pay in April... For the vast majority of people, extending just kicks the can down the road. Now you just ruined your summer." (04:13–04:35)
• Professional Advantage: Early filers get priority attention from their tax advisors.
  • Quote: "If you're one of the first people there, you get your tax person when they're fresh, when they're excited." — Joe (05:01)

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2. The 7 Big Tax Changes for 2026

Sourced from Wall Street Journal (Ashley Ebling and Richard Rubin)

1. Increased Standard Deduction

• Single: Up $750 to $15,750
• Married Filing Jointly: $31,500
• 65+ Additional Deduction: $2,000; New Senior Deduction: $6,000 (for next three years)
• Quote: "There's a few dollars. This one's going to be easy... your tax software is going to do this one for you." — Joe (09:54)
• Note: Most filers will find tax prep simpler; fewer need to itemize.

2. Expanded SALT (State and Local Tax) Deduction

• Raised Limit: Up to $40,000 (phased out for higher incomes: phases down starting at $500K AGI; at $600K+, the deduction cap reverts to $10,000).
• Quote: "They changed it, and now you can go up to 40k, but it’s still limited by income... if you're in that sweet spot... you get a little bit of a benefit there." — OG (11:38–12:47)

3. New Tips Income Deduction

• Up to $25,000 for qualifying service industry workers.
• Important Criteria: Income must be legitimately classified as tip income (not mandatory service charges or unqualified reclassifications).
• Quote: "If you don't work in a tip business, don't try to make part of your income, tip income. And if you do, get some pro help." — OG (15:04–15:50)
• Online Creators/Patreon angle: Potential for creators to use this, but must tread carefully.

4. Overtime Pay Deduction

• Up to $12,500 for eligible workers.
• Requires precise classification; not all overtime will count.

5. Auto Loan Interest Deduction

• Deduct up to $10,000 in new car loan interest.
• Quote: "Have you looked at the price of a new car recently? ...All those things now." — OG (16:34)

6. Increased Child Tax Credit

• Maximum increased by $200 per child.

7. Charitable Giving Adjustments (previewed, expanded later)

• New Floor (2026): Deductions only count once charitable contributions exceed 0.5% of AGI.
• Cap: Itemized deductions (for high income) capped at 35% of AGI.

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3. Additional Tax Planning Strategies & Smart Moves [Second Segment]

Based on an Ally Text article, the hosts discuss:

1. Retirement Account Maximization

• Prioritize employer match; increase contributions with raises.

2. Tax-Loss Harvesting

• Not as important for younger/smaller investors except with crypto (no wash sale rules yet), but can offset gains or up to $3K of ordinary income.

3. Health Savings Accounts (HSAs)

• Triple tax advantage: deduct contributions, grow tax-free, tax-free distributions for healthcare.
• Use for now or later (“don’t let perfect be the enemy of good”).
• Quote: "If you're somebody who just has an HSA and you're using it tax free to pay for your stuff... Still beautiful." — Joe (35:09)

4. Strategic Tax Bracket Management

• Diversify buckets (pre-tax, Roth, brokerage) for flexibility in retirement.
• Don't get caught up in “all Roth vs. all pre-tax” arguments; unknowns make flexibility king.
• Quote: “We don’t know where tax brackets are going to go... Give yourself the flexibility.” — Joe (38:34)

5. Charitable Giving Strategies (detailed)

• New limits/floors make timing and batching gifts more important.
• Standard deduction minimizers: consider giving larger amounts less often to maximize deductions.

6. 529 Plan Optimization

• Use for state tax deduction and tax-free growth/withdrawals.

7. Income Timing & Deferral

• Recognize and manage income (and deductions) in optimal years.

8. Asset Location Optimization

• Place tax-inefficient investments in sheltered accounts; tax-efficient funds in taxable accounts.

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4. Notable Quotes & Memorable Moments

• On tax procrastination:
  "Now you just ruined your summer. Because it can be like—kids start going back to school and you're going, ‘Oh crap, I still do my tax!’" — OG (04:13)

• On the new purpose-driven auto loan deduction:
  "Which to OG to your point, could be one tenth of the interest that you paid on that high-interest loan." — Joe (18:24)

• On hotel rooms and personal boundaries:
  "I would rather sit in a hotel lobby and drink coffee all night than share a room with another human being—not even my kids. I'll sleep in the car." — OG (28:31)

• On the never-ending Roth vs. pre-tax debate:
  "This is an idiotic argument because we don't know where tax brackets are going to go... Give yourself flexibility." — Joe (38:15)

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Timestamps for Key Segments

| Segment | Timestamp | |---------------------------------------------------- |-----------| | Opening banter and tax preparation mindset | 00:00–06:01 | | Seven Big Tax Changes for 2026 | 09:18–20:57 | | Tips Income and Overtime Deductions | 13:54–16:34 | | Auto Loan Deduction and Car Talk | 16:34–20:57 | | Tax Planning Smart Moves (Retirement, HSA, etc.) | 31:03–42:14 | | Debating Roth vs. Pre-tax and Flexibility | 37:38–39:35 | | Charitable Deduction Changes | 39:35–40:50 | | Personal finance trivia and TikTok minute | 26:10–31:01 | | Seattle vs. Boston Super Bowl meetup plug | 45:31–49:13 | | Three big to-dos and closing jokes | 49:13–51:50 |

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Fun & Notable Moments

• Willie Nelson IRS Story:
  Story about Willie Nelson settling $16.7M in back taxes. Quips about tax shelters:
  “Where do homeless accountants live? In tax shelters, right?” — Doug (50:01)

• Movie Theater Sticker Shock:
  A humorous bit about someone spending nearly $290 at the movies—including 28 hot dogs—as a tongue-in-cheek take on inflation and lifestyle creep. (42:14–44:54)

• Hotel Room Banter:
  Running joke about OG absolutely refusing to share a hotel room, even with friends or family, leading to a lively TikTok discussion segment. (28:31–30:50)

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Actionable Takeaways (Doug’s “Big Three”)

1. Review Tax Changes:
   Tax rules and your life change every year—review both and grab opportunities for bigger refunds.

2. Be Strategic with Flexibility:
   Don't obsess over precision (e.g., all Roth vs. all pre-tax). Build flexibility and adaptability into your financial plan.

3. Check the Updated Tax Guide:
   Stacking Benjamins’ monthly-updated tax guide is available at stackingbenjamins.com/guides.

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Resources Mentioned

• Show Notes & Tax Guide
• Wall Street Journal Tax Article (if you subscribe)
• [Ally Text Tax Optimization Article]
• OG and Anna’s Financial Planning Team

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Closing Thoughts

Combining solid, practical tax tips with humor and banter, Joe, OG, and Doug help make tax season less intimidating—and maybe even a little fun. Listeners are reminded to stay adaptable, maximize their deductions, and always check with qualified professionals when it comes to nuanced or complex tax situations.

Final Joke:
"There are three types of accountants: those who can count and those who can’t." — Doug (50:22)

—Summary prepared for listeners who want to keep more money in their pocket this tax season and enjoy the ride doing it!

Transcript

[Joe]

It is Monday. My feet are cold, but my heart is warm because I get to spend time with you two.

[Doug]

God, you're really bad at lying.

[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?

[Doug]

Oh, so did you just say February?

[Joe]

Isn't it? There's an R in there. There's an R. Come on. You know what else? There is.

[Doug]

There is. But I mean, only weirdos say it. It's like saying salmon.

[OG]

I've.

[Joe]

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.

[Doug]

Raisings.

[Joe]

We got some troops we need to salute.

[Doug]

Saluting.

[Joe]

To have the men and women making podcasts in mom's basement and the men and women trying to stack Benjamin's. Here's to all the people that kept us safe all weekend long. Thank you for all you do. Let's go stack some Benchmans together now.

[Doug]

Thanks, everybody.

[Joe]

Stacky.

[OG]

Stacky.

[Doug]

Joe, the bottom of your mug is red. Does that mean you're excited to see me?

[Unidentified Motivational Speaker]

Oh, it's Monday, baby. It is 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.

[Doug]

Live from Joe's mom's basement, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor, Doug, and. Ah, February. Sorry, February. Quiet, candlelit dinners, romantic evenings, and prepping my taxes. Oh, yes, the good times. So what's different this year on Today's show? The 7 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. 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 to guys who are romantic old softies about money, it's Joe and. Oh, Juju. Ja Ji.

[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 Salsi.

[Doug]

Hi.

[Joe]

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.

[OG]

No, I think it's police. Like your tinsel, as in.

[Joe]

Yeah.

[OG]

Did you put your tinsel on the tree yet?

[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?

[OG]

Yeah.

[Doug]

Oh, my gosh.

[Joe]

Wow. That is a blast from the past. But we're not going to get into that. Cause, oh, gee. It is officially February. It's officially tax prep season. Time for people to go, go, go.

[OG]

I think you're a few days behind if you're waiting till the 1st of.

[Joe]

February to get going on your taxes.

[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 into the cpa? No.

[Joe]

What's wrong with you? If you haven't done that yet? That is. That's 100% you. I've known you for how long? It's 100% you. January 2nd. You're like, let's go. Come on.

[OG]

Actually, I've changed my opinion about taxes. I used to be the perennial, like, extension filer. Like, I'll just extend it. 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 going to owe.

[Doug]

So.

[OG]

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 got to wait. 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. Yeah. Because summer's going to come and this can be like, right. The kids just start going back to school, and you're big. You're going, oh, crap, I still do my tax. Oh, frick. And now you're trying to find stuff from 20 months ago to get to your CPA because it's due on October 15th if you're filing your personal return. So I try very hard to be the first person in the door. So I do. I send.

[Joe]

All.

[OG]

All the business stuff is already gone to the CPA the second week of January. Like, QuickBooks is updated. The banks are reconciled. Start going.

[Joe]

Well, that wonderful conversation we with Hannah Cole back at the beginning of 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, you get them when they're excited. If you're taking it in there April 8th or April 10th.

[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 enrolled agents, 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. So I want to be done. I want to start that audit clock, baby.

[Joe]

Get that done. Have. Have my next 11 months to myself, not worrying about my taxes. Love.

[OG]

I know you guys, people are yelling right now. They're like, but Schwab doesn't send my 1099 until the middle of February. I can't.

[Joe]

Okay, just get the rest of it ready.

[OG]

Be done with everything else. Like, have it all ready to go. And then when you get the 1099, put it on the pile. Dud.

[Joe]

I had some other news that came up recently. I found out how I got on that tech stream where somebody you don't know texts you about every other day, ask you how you're doing or do you want to 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. When I signed up for our new product, the Vault, I was our first user, by the way. Immediately, I saw exactly what an 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 text appeared. So I began then, very quickly, well, actually, I didn't do anything. 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 twentieth of what the Vault does. Check it out@stacking benjamin.com 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. All of that. Stacking benjamin.com 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. So let's hear from them. Was that a giggle? Was that a. There it is.

[Doug]

The Pillsbury Doughboy. That's what I sounded like you did.

[Joe]

Like somebody punch that. Just poke finger right in the stomach.

[Doug]

Round belly.

[Joe]

We're going to hear from them and then we're diving into helping you maybe keep a few more bucks in your pocket this tax season.

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[Joe]

Another pina colada?

[OG]

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[OG]

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[Doug]

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[Joe]

Inspiration for today's discussion comes to us from the Wall Street Journal. This piece was written by Ashley Ebling and Richard Rubin. The new tax rules that can get you a bigger refund this year. There are seven of them. OG so let's dive into exactly how we can maybe help our stackers keep more money. We'll also link to this if you have a Wall Street Journal subscription, you missed it in our Show Notes page@stacking benjamins.com first of all, the standard deduction bigger up by 750 bucks. This one's going to be easy, OG I mean, your tax software is going to do this one for you. But the standard deduction up to 15,000 7:50, that's a $750 increase from a year ago. So there's a few dollars.

[OG]

And that's the single one.

[Joe]

That's the single standard deduction.

[OG]

Yeah. And the other thing that this helps too, by the way, is it makes it so if you're. Because I think Mary Join is, I mean, is it Double, is it 31.

[Joe]

Married filing jointly for 20, 25 is 31,500.

[OG]

If you're not going to be at the $15,000 level or 32K level for married filing joint, it eliminates all the record keeping. Don't worry about it. Back to, well, I got to 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 limited in some places. That's one of your, that's. I bet that's one of your items on your list here, property tax changes. But if you're not at 30, 32K, then don't stress it. You just take the line item and go. The good news is that the tax software, CPA, TurboTax, whatever, is going to calculate all that for you anyway.

[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 2,000 bucks.

[OG]

You get a little kick. Yep.

[Joe]

Kicker, additional standard deduction.

[OG]

You guys have that to look forward to here shortly. That's cool.

[Joe]

There's also the new senior deduction for an additional $6,000. That's a big one. That's going to last just the next three years. Let's talk about the salt deduction because this was a huge difference. 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?

[OG]

Well, until this year, you were limited. And this all goes back to the 2017 tax law change between 2017 and today, 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, actually, turns out other people pay taxes too, not just the Uber will. Billionaires and trillionaires. So. So they changed it, and now you can go up to 40k, but it's still limited by income. So there's an income threshold, and it decreases. Nothing that you have to keep track of because the software, your CPA 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 state taxes, local taxes, you get a little bit of a benefit there, which paying taxes on taxes kind of sucks. So I get that.

[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. But modified adjusted gross income exceeding half a million dollars, or if you're married, filing separately, 250,000 bucks, the deduction reverts to the previous cap of 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. 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? Is there a way for your audience to tip you? Are there a way for people that you work with to tip? Is. Is there a tip now? You got to be very careful, like he said, and you don't want to classify something as a tip. That's not a tip. But this is $25,000 as an income deduction if you're somebody who's working in the service industry.

[OG]

Yeah. I mean, again, this has to be 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'm 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, 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 take advantage of that benefit. But to go back in time and be like, well, actually, 25,000 of my income was tip income, probably not super easy. The other thing that I read about this was if it's a mandatory tip, it doesn't count. So, for example, let's say that you work at a real fancy restaurant.

[Doug]

I was going to say. So every restaurant now?

[OG]

Well, yes, but I was thinking about in the context of you've got an eight person table, you're at the big fancy steakhouse in town, and they say they add, we automatically include a 20% gratuity on parties over six. 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, don't try to make part of your income, tip income. And if you do work in a tip business or if you're the owner of a tip business, you really got to tread carefully and get some pro help here on how to classify this because it's not super clear and easy.

[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 or something. And he's talking to some of these creators about, hey, is there an opportunity for a Patreon? Because this is 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.

[OG]

Yeah, maybe.

[Joe]

Next up, overtime pay deduction, $12,500. Again, work with your tax accountant on this one because a lot of stipulations on overtime pay. You can't start reclassifying your income as overtime pay. But if it has been, historically. There could be a deduction there. Auto loan, interest deduction, new this year, of up to $10,000.

[OG]

Ochi, I mean, have you looked at the price of a new car recently? 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 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.

[Joe]

One for a smart car.

[OG]

All those things now.

[Doug]

And he calls us old, and he's referring to Oldsmobiles.

[OG]

Fun fact.

[Doug]

Make that hasn't been made.

[OG]

I actually. An Oldsmobile was my first car that I bought myself, believe that or not.

[Joe]

What's the first car you bought yourself, Doug?

[Doug]

First car I bought myself was a Chrysler Horizon. Is it a Dodge Horizon? Same vehicle. And just 10 short days before I paid it off, it was found in a lake.

[OG]

Wow. And no one knows how it got there.

[Joe]

Was found.

[Doug]

No. The crappy thing is I still had to pay it off. It's not like I did it, okay? It got stolen. And I can't figure out how the.

[Joe]

Insurance company found it out there.

[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.

[Joe]

And it was gone. Mine was a Chevy Monte Carlo with the ceiling that no longer stuck. You know, the hood liner.

[Doug]

The headliner was.

[Joe]

Yes. Yeah. All came down. It was good. I tried to put a new radio in that. I bought one of these aftermarket stereos because 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 it with my hand on the radio, and I just felt this weird buzzing sensation. And then I turned the TV off, and it shot me out of the car, the radio. As I found out what the grounding wire was for.

[OG]

You were the grounding wire.

[Joe]

I was apparently the grounding wire. Yeah. 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 want to look at the salt deduction. If you're somebody that works where you get a lot of overtime or you work in a traditionally tip field, you definitely want to 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. 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 tenth of the interest that you paid on that high interest loan on that.

[OG]

It's crazy how much these things cost now. Bajillion dollar car and they're like unfixable too. I'm not handy in any way, shape or form. I could change a tire and I could change oil if I had to. 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. Oh, did you want heat? You wanted the heated seats to work, right?

[Joe]

Right.

[OG]

Oh, that's $8 a month. It's like, are you effing kidding me? I don't know. Old man yells at Cloud A friend.

[Joe]

A friend of mine yesterday was telling me that their elderly parents just had to replace their furnace that was 46 years old. Furnace amazing. 46 years old.

[OG]

They were in for a shock.

[Joe]

It all had this one little part every time that just need 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 whiz bang thing that's going to die in 10 years and it's going to cost you 18,000 bucks.

[OG]

Yeah, I mean I just got an email from wemo, right. The company that does like the home automation stuff.

[Joe]

Sure.

[OG]

They were bought by Belkin 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, it was just not, you know, just doesn't work. Yeah, it's like, sorry.

[Joe]

Yeah, it's incredible.

[OG]

Could my light switches still work? No, no, just buy new stuff.

[Joe]

Yeah, duh. Just go buy it again. We will link to this in our show notes page@Stacky Benjamin.com in the second half of today's show, we are going to dive into another piece that talked about all the different tax things that you should be looking at or at least eight other smart tax moves that you should look at any year 20, 25 or any year we'll dive into those. We also have our tik tok minute. But first we're going to talk taxes. 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 maybe started to solve the problem.

[Doug]

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 padlocking his properties. What segment? 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.

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[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, so I 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 sheltery, because they sure found him pretty easily. He released an album in 1992 to try and help his situation, called the IRS Tapes who'll Buy My Memories, which included outtakes, bloopers, and lots of glimpses into the creative process. So who was this 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 of podcasting.

[Joe]

Joe and OG all the federali say could have had him any day. Love that song. OG you big Willie Nelson fan?

[OG]

I mean, not. I wouldn't. I wouldn't say a big.

[Joe]

But it's like, you can't not be a casual fan. Like your Willie Nelson song. You're like, oh, that's good. I'm like you. I'm like, yeah, not a big fan, but still.

[Doug]

Right.

[OG]

Seems like a cool dude to hang out with.

[Joe]

I think he would be. He's always baking something, Maybe himself. You know, he ended up suing his accountants for $45 million, saying that he didn't know how this stuff worked. Price Waterhouse came back, goes. Dude, you were in all the meetings. Like, you knew exactly what we were setting up. Don't say that. You're not.

[Doug]

Ignorance is not a defense.

[Joe]

Yeah, they eventually settled out of court, and everything was private. You have no idea how that ended, but.

[Doug]

But he got, like, a 45% discount with the. When he settled there, so that sounds like a strategy.

[Joe]

Well, even more than that, because I think they originally thought. Doug, I. They originally thought he owed way more than that $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.

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[Joe]

So there's your lesson. Just cut another album to help pay your taxes, sue your accountant, and life is good. That's maybe not the lesson that we. That we need from that. Hey, time for our Tik Tok minute. This Is the part of the show where we shine a light on a Tik Tok 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 going to hear in this video. Guys, how much money do you think comedian Nate Brady 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.

[OG]

American Airlines.

[Joe]

American Airlines Arena. Like, filling that up one night is an incredible feat. Nate Bergazzi sold out three shows. Like, sold out one and had to add another one and add another three shows for this comedian. Dudes rolling in money.

[Doug]

He's got a little extra in his checking account these days.

[Joe]

So he's super wealthy and obviously becoming very popular very quickly. 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 and. Well, Jen wants to know the same for us as what they ask. Napergazzi, Dusty Slay and the rest of these comedians. You guys are all on the road together. There's only two hotel rooms available.

[Doug]

Who's rooming with whom? I think Nate's got his own room. That's exactly right.

[Joe]

I like that.

[OG]

And I guess I sleep in the.

[Doug]

Middle because you need the plugs for the seat.

[Joe]

You're the three in one. And Dusty says, I'll sleep in the middle. Cause the other two need the plugs for the CPAP machines for them.

[Doug]

Joe, if it's us on the road, I'll just say right now I'm. You and I are bunking together. Absolutely.

[Joe]

I think we vote for OG to have his own room. Yeah, Jen, to answer your question, all three of us vote OG gets the room.

[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 than share a room with another human being and not even my kids. Nope. Like, if there's only money for one hotel, I'll sleep in the car. It's not happening ever.

[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 4 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.

[OG]

No, she's fine, obviously. But I remember one time, my after school activity that I was doing and we had to stay the night and the guy that I traveled with was like, hey, we should just drive back. And I'm like, no, it's kind of long. I'm going to stay the night. And I could tell he was just kind of like, I don't know that I want to spend the money to, you know, it's a commitment. And that's cool. 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. It's like 17,000 points. That's totally fine. And he's like, okay, cool. That works for me. And so we walk in there and I'm like, check it in. And I'm like. And then he needs his key too. And she pulls up, she's like, okay, here's your key. 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? Like, yes. I am not going to stay in another room with another human being.

[Joe]

It is worth the money.

[OG]

I would rather have fewer Marriott points.

[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 in a central living area. Thank God. Separating the two bedrooms. Because I heard noises, Joe. I don't know what goes on in there, but there I did. I'm glad. I think I know he why he wants to be by himself because things happen in that room.

[OG]

It's like an exercise. Reminds me of that joke.

[Doug]

Yeah, it is. It's like Linda Blair.

[OG]

What do you mean, an exorcism? That's a joke. It's not an aprgazi joke, but it's a joke.

[Joe]

That's another day. Or we can't share that one.

[OG]

Oh, I'll tell you guys. I'll tell it later.

[Joe]

Okay. All right, time to move. Thanks, Jen, for that TikTok minute. And yes, Og gets his own room. And I think we all agree. Exactly. It was very easy for us to figure that one out.

[Doug]

Oh, yeah, no thinking.

[Joe]

Let's dive back into tax planning for this beautiful Monday because this other piece from allytext.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 tech strategy. Number one is, oh, gee, 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 at least.

[OG]

To the employer match contribution, right? If your employer does, you know, a 50 cent match on the first 6%, you got to be doing six because it's a free 3%, it's a free 50% return on your in your money. So absolutely have to take advantage of that. And then I'm a big fan of contributing as much as you possibly can for no other reason than out of sight, out of 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. 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. Yeah, get there.

[Joe]

Well, and I like a suggestion here because, 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 when you get a raise. If you get a raise in 20, 26, pay yourself first with that raise. Like do the bump with the race 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 20s, you know, really excited about tax loss harvesting. 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]

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. Let's say that you go, hey, I want to buy 1,000 bucks of Bitcoin, and a week later it's down to $700. Because that can happen. 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. 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 going to tax loss, harvest this $8,000 of this mutual fund that I lost money on and then I'm going to turn around and do like, okay, cool, but for what? If it's just a line item on your tax, you can only deduct 3,000 a year above your gains. It's not zero, but it's not a lot either. So this is a maybe for me.

[Joe]

Yeah. Third on the list is health savings account triple tax advantage. If you've got a health savings account available, this, I think after you get past the match in your 401k could be the number one place to put money because you can use it later on for retirement. If you want to get very similar tax advantage for retirement, but you also have available for health care, like, I don't know, I think the HSA is the way to go if you've got one available.

[OG]

HSAs are great. You got to be careful of how much cash your HSA requires you to have in the cash portion. You could spend an entire year contributing to an HSA and never get to invest a dollar because your company, HSA company mandates a certain amount of cash. You know, there's again balancing act here. Is it worth hanging onto all these receipts and record keeping for two decades to get the tax free age 65 thing or is it just better to use some of it as you go?

[Joe]

Yeah. I remember my friend Belinda Rosenblum from OwnYourMoney.com who works with entrepreneurs on their tech systems and setting up better automation. And I remember her talking about the HSA with a SOG and going, you know what? 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, 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.

[OG]

Yeah. And 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, you could easily have 50, $80,000 in an HSA. And now your HSA is going to make as much money invested as you contribute. Right. 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 potentially future money.

[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 and 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 out of that pre tax strategically thinking about that a little bit, I think can go a long way. Thinking about it a lot. Yeah.

[OG]

I mean all of the decisions that you make when you get toward retirement are all going to 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. Should I do pre tax or Roth? 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. 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.

[Joe]

You know, it's funny, Doug, for several years we talked about the dumbest discussion in personal finance was the whole share checkbook thing. Oh yeah, do I share a checkbook? And you just poking your eye out like, oh God, that discussion again. I think the Roth versus pre tax, you know, lately we've got some people coming out going, no, you should definitely do pre tax because of blah blah, blah, blah, blah. And other people going, no, you should do all Roth because of blah blah, blah, blah, blah. I think this is an idiotic argument because we don't know where tax brackets are going to 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?

[Doug]

Oh, you think it's dumb because there's an obvious answer?

[OG]

No, there's no.

[Joe]

Because there is no obvious answer.

[Doug]

Okay.

[Joe]

Because everybody's solving for something that we don't know. We don't know where tax brackets are going to go. So we don't know if taking all pre tax today is the best decision. We also don't know where tax brackets are going to go.

[Doug]

So today might not be the best. Because 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. It's the devil we know right now. So take the bullet now. That's where I thought you were going with.

[Joe]

Well, people say take the bullet now because your tax bracket is going to 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 because you're going to pay less tax when you're in retirement. All right, well, that's a false.

[OG]

Or your money compounds into infinity and you're 80 years old with $13 million in an IRA. I would argue that might be the richest you ever are in your life at that point.

[Joe]

Yeah, we just, we just don't know. Give yourself flexibility. Stacky benjamins.com 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. Number five on here. I won't spend a lot of time on charitable tax giving strategies. Oh, gee.

[OG]

Well, there's been some changes to that this year for 2026. The amount of money that you. I'm going to screw this up because I'm doing it off of memory here. 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 2,000 to charity, you don't get to write off the 2,000. Somebody's going to write in and go, that's not it. Something like that. All that to say that it matters, right?

[Joe]

Here it is. It is a half percent 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.

[OG]

Weird.

[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.

[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. 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 ado about nothing if.

[Joe]

You are in a state that has a state income tax. Using 529 education savings plan optimization, they work through an example of this Couple in a state with tax deduction. A couple in a state with a tax deduction contributes $10,000 to a 529 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 have had some capital gains taxes if they had not put it in the 529 plan. So using 529 plans for college. A good idea. Number seven, income timing and deferral strategies. I think we already got into that. And then 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. 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@stacking benjamins.com Guys, let's wander out on the back porch. It is a Super bowl week and we'll get into that in a second before we get to the Super Bowl. Stacker Scott.

[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? With his partner. He just wants to go a couple of tickets to the movies. Talk about sticker shock. $287. Yeah, $287.97 just to go to the movies. And he's a member of that. It's like the club, the amc.

[OG]

There's more to that story.

[Joe]

No, hold on.

[OG]

Wait.

[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 AMC called Stubbs. And even the discount didn't help that out. So a couple of tickets, Some large popcorn.

[Joe]

Yeah. How much were the tickets? How much were the tickets?

[Doug]

Tickets were. Looks like about 16 bucks a piece.

[Joe]

16 bucks each. Just go see a movie. 30, 32 bucks.

[Doug]

A lot of money right there. Large popcorn, fountain, drink, and some hot dogs. Yeah. Two hundred and almost 290 bucks for the two of them.

[Joe]

How much was the popcorn?

[Doug]

Ten bucks.

[Joe]

Yeah. Still way overpriced, but anyway. And the drink.

[Doug]

Drink was 750.

[Joe]

Yeah. How much were the hot dogs?

[Doug]

Hot dogs? Well, they were. I'm not sure what the line. I could do the math, but it does appear that one of them was pretty hungry. There were 28 hot dogs.

[Joe]

20? Only 28 hot dogs? I mean, you go to the movie OG the movie theater and you have 28 hot dogs.

[Doug]

Yeah, 28 hot dogs for $223.72. This still seems like price gouging to me. 28 hot dogs is normal. Who doesn't eat?

[Joe]

Who does go to the movie theater? Who among us throw the first stone? Cast the first stone. If you don't go to a movie theater and have 28 hot dogs while you're watching your movie.

[Doug]

So $8 hot dogs.

[OG]

What's your take on the delivery to your seat at a movie theater?

[Joe]

We don't have that theater in Texark.

[OG]

Oh, really? That's only what we have. I haven't been in the movies in a long time, but that's only what we have. I was reading something the other day that said it was somebody like Matt Damon or somebody was like. They absolutely hate that. Right. You're meant to lock yourself in a room and focus all your attention on this artwork that they just did, basically.

[Joe]

Right.

[OG]

Instead, you're pressing buttons and playing on your phone and like, oh, anybody need some more hot dogs? Okay, cool. I'm gonna order four more hot dogs. And then the guy comes in like a waiter and kind of in everybody's way, and I'm kind of there. We don't need couches to lie on.

[Doug]

Yeah.

[Joe]

I haven't been to an Alamo Drafthouse in a while, but when I went 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.

[OG]

It's already nasty. Like when you're. The floor's all sticky and down at The Drafthouse.

[Joe]

That was a. That was a nice place back when it was pre 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.

[OG]

Like a drive in movie. Yeah.

[Doug]

How much were the 28 hot dogs there?

[Joe]

I took probably of 11 gajillion bucks, but they had real butter for the popcorn. I did appreciate that.

[OG]

Artisan pizzas and stuff. It's like, come on.

[Joe]

So, so, so good.

[OG]

A box of jujubes and yes, that was fun.

[Joe]

Scott, by the way, thanks for posting that in the basement.

[Doug]

There's also some fun coming up. In about a week, a week from yesterday, the big game super bowl is about to happen in which New England host of a fine Benjamin's After Dark group will be beating the Seattle Seahawks by 28 to 24.

[Joe]

You threw down the gauntlet right there.

[Doug]

I mean, I'm just spitting facts. I mean, I love the Sam Darnold story. It's inspiring. But Drake May is a beast and they're going to pull it off.

[OG]

That scored what, 10 points or 14 points in the final two games.

[Doug]

He's just a winner. The guy just wins. Plus he's, you know, he's been with.

[OG]

The string quarterback that hadn't started in five years, but sure, yeah.

[Doug]

Wow.

[OG]

They really took it to those Broncos 10 to 7. I like this.

[Joe]

Even on the episode, we're getting a little heat back and forth.

[Doug]

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 want to have a team in the super bowl, start your damn group.

[Joe]

So you got to do. Yeah, we're actually having our meeting with Tucson. That's pretty exciting. Hopefully getting that rolling. And by the way, if you're in Boston, like, wait a minute, 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 stacking Benjamin's Boston and you will see the group get in. And when that first meeting happens, it's right around the corner, Doug. And you've already seen in the basement, they're starting to throw barbs at each other. The Seattle group founders and the Boston group founders.

[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.

[Joe]

We've had meetups there when I've come to town, but we have not had a monthly meetup group. Well, we do have one. It is founded, it is rolling. We just have not had our inaugural meeting yet. So Seattle often rocking with our buddies Chris and Cole out there in Seattle. If you're in Seattle and you're not going to those meetings, what are you waiting for? Oh also by the way, we figured out where our meetup is going to be in Seattle when I come out there for retirement. The retirement conference. Guys, we will be on Thursday March 5, 6:30 in Capitol Hill at Allegiant Brewing. We've had a meet up there before. Great, great time at Allegiant Brewing in Capitol Hill, the neighborhood of Seattle. So come join us Seattle Stackers. We'll be there at 6:30 having some fun. Thursday March 5th. Head to stacking benjamins.com meetup to sign up for that. Love to see you guys while we're there. That's going to just about do it. Today we got a couple more resources. Number one is if all this tech stuff is really got you down and you're like, I don't even know where to begin. We have a tax guide. We have a series of guides. But our tax guide is fantastic. We update it every month. Stacking benjamins.com 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 stackingbenchments.com OG and he and Anna and the rest of the team happy to talk to you about how they can help you make better financial planning decisions which include tax decisions in 2026 and beyond. All right, those are a couple 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.

[Doug]

Oh, I'll tell you, Joe. First, take some advice from our headline. 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. She's got no sense of humor. Listen to these humdingers what kind of humor does an accountant have? The self deprecating kind.

[OG]

Nope.

[Doug]

Yep.

[OG]

That's not the joke.

[Doug]

She didn't like this one either. But it's amazing. Where do homeless accountants live? In tax shelters, right?

[OG]

Yeah. The first one was not self deprecating, Doug. Self depreciating. It's got to be self depreciating.

[Doug]

But they both mean going down.

[Joe]

I think it was self depreciating.

[OG]

The joke has to be self depreciating.

[Joe]

I like how Doug's telling the joke. Can't figure out why mom doesn't laugh.

[Doug]

Okay, whatever. We can analyze these later. Those are hilarious. I think we can all agree they're just hilarious. 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?

[Joe]

Do you got the crickets track?

[Doug]

OG Quick Agree to disagree.

[Joe]

You got it.

[Doug]

Looking for better tax help? Check out our tax guide. 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 [e-mail] Guides this show is the property of SB Podcast, LLC, Copyright 2026 and is created by Joe Salsihai. You'll find out about our awesome [e-mail] 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. Oh yeah. Before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug, and we'll see you next time back here at the Stacking Benjamin show.

[Joe]

Sat.