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Your Year-End Tax Guide – Ep. 309

  • by Judson Crawford
  • •    October 13, 2026
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by Judson Crawford
CPA, Partner

How proactive planning can simplify year-end tax strategies and financial decisions.

In this episode of the Accumulating Wealth podcast, Judson Crawford and Hunter Satterfield explore the essential tax planning moves to help reduce your tax liability as the year ends. With special guest Keith Klein, CWA Partner, they discuss marginal tax rates, year-end adjustments, and strategic decisions that can significantly impact your 2026 tax bill. They walk through changes to 1099s, the PTE tax, and highlight the Augusta Rule, among other significant points. If minimizing your tax liability and maximizing deductions is your goal, this episode is your go-to resource. 
 
Have questions or ideas for Hunter and Judson? Reach out at cainwatters.com/wealth.

WHAT YOU’LL LEARN

  • Key tax planning steps to take before year-end
  • Simplified insights on 1099 changes
  • The importance of asset placement for tax purposes
  • How to leverage retirement contributions for tax benefits
  • Strategic impacts of early tax payments

Questions Answered in this Episode

How can business owners prepare for year-end tax filings?  

By reviewing income projections and maximizing deductions before the end of the year. 

What is the pass-through entity (PTE) tax?  

The PTE tax strategically shifts state income tax to a business entity, enhancing deductions. 

What 1099 changes do you need to be aware of? 

The federal reporting threshold for 1099s increased from $600 to $2,000 starting in 2026. Identify vendors early and process 1099 filings in a timely manner to avoid penalties. 

How does the SECURE Act 2.0 influence your retirement planning?  

It updates contribution limits and provides startup credits for 401(k) plans. 

Key TakEaways

  • Tax planning timing can maximize efficiency and reduce liability
  • Understand recent tax law changes
  • Asset purchase timing affects tax deductions
  • Timely financial reviews prevent costly mistakes

Who's this episode for?

  • Business owners
  • Professionals aiming to optimize financial outcomes
  • High-income earners interested in reducing liabilities
  • Individuals with charitable giving plans

ABOUT THE HOSTS

Hunter Satterfield – CPA & Partner

  • Financial Advisor with Cain Watters & Associates since 2007
  • Chief Investment Officer

Judson Crawford – CPA & Partner

  • Financial Advisor with Cain Watters & Associates since 2004
  • Public speaker, New associate mentor, Marketing Committee member

Reach Hunter and Judson here: cainwatters.com/wealthpodcast/

About the show

The Accumulating Wealth Podcast helps business owners and professionals make smarter financial decisions through insights on tax strategy, investing, and long-term wealth planning.

Additional Resources

Podcast video
  • Podcast Video
Full transcript

Welcome to the Accumulating Wealth podcast. I’m Hunter Satterfield. And I’m Judson Crawford. We’re CPAs, wealth advisors, and partners at Cain Watters and Associates, a financial services firm here to help you navigate the decisions you face every day. I don’t know about you, Judson, but I feel like I went to sleep last night and it was just June. 

Then I woke up this morning, and somehow, it’s already October, which basically means December is tomorrow, and we need to be ready for it. And by being ready, I’m guessing you don’t mean updating your Amazon holiday wish list? Not quite. I’m talking about our annual year-end tax reminder list: the things business owners should review before December 31st to help reduce liability and avoid surprises. And because taxes are always better with backup, we brought in a guest to help us walk through what to keep on your radar.  

All right, listeners as always, wonderful topic, lots to cover here. We’re going to move relatively quickly, so you might want to slow us down for the first time ever. But Judson, we have one of our esteemed multi-episode recording guests with us, right? Yeah, and not only is he a multi-episode guest, he is one of the partners that for the last few years has written our year-end tax planning blog. So that’s what we’re going to be talking about today, taxes. That’s right. 

One of our Red Raiders, many of the Red Raiders that are here at the office. We are joined by Keith Klein. Hello, Keith. Hello. Welcome. Thank you for having me. Yeah, I think this is my fourth or fifth time on the podcast, so I appreciate the welcome back here. 

Yeah, you have record numbers for listeners because everybody actually cares about the year-end tax planning stuff, so. True. Well, and I think, Judson, a good place to start is this is not one of those years, listeners, where it’s like marginal rates are changing dramatically. I mean, it’s 37 this year is the highest rate, 37 next year. 

There will be some minor inflation adjustments on the different income limits for the marginal brackets. But this is not like a rush out, Judson, before the end of the year and buy stuff, right? Yeah, no big breaking tax planning news compared to prior years. It’s just the typical blocking and tackling that you need to think about before the end of the year because obviously you also don’t want to overpay in taxes. 

And like you said, there’s no rush to go out and do something that you don’t need to do, but you want to do the things to be as tax efficient as possible, and so that’s kind of what we’re here to talk about. And then there are some things that are regulated by tax that aren’t necessarily tax savings that you just need to think about because you need to do them before the end of the year. 

 That’s right. And so, we’ll just kind of rip through these, folks. Keith, you want to start with… the 1099 thing was like a big thing that our clients were all like, “Oh, that’s awesome that that’s a new thing.” We talked about it earlier in the year, but you want to talk about the changes to 1099s? 

Yeah, yeah. The basic change is very simple. So, the limit for what you pay to vendors and you had to issue them a 1099 was $600, and it had been there for the last, I don’t know, 10 years or so. And they increased it significantly, we think, to $2,000. We kind of asked our accounting department to go and look and see, “Hey, how much less work are you guys going to have to do with this new 1099 limit? Is it really going to kind of help us out and keep January moving along with prepping year-end books and things like that?” And the answer’s no. 

It’s only about a 5% reduction based on what we saw. Now, it can vary widely based on your particular situation obviously, but most vendors that you’re paying, you’re paying over $2,000 to, so you’re still going to have to issue close to the same number of 1099s. 

Yeah, and this again, listeners, is something that will need to be done before January 31, but it’s a good time as you approach the end of the year to just start to identify those. So, you can either prep them yourself, or if you work with us on the accounting side, we can as well. Shall we move on? Big penalties on these 1099s if you don’t get them done in time. Big time. So, it is important. Yeah, make sure you get those W-9s in. 

I think we need to move on to the devil of all devils, worse than PPP loans. What do we need to do here, Judson? It’s just gone on and on and on and on. It’s the devil. We were hoping that it wouldn’t go on and on, but it has, and that is the PTE tax or the pass-through entity tax. Keith, what is that? 

So that is when you live in a state with a high state income tax, basically your Schedule A deduction for most of our clients is limited to $10,000. That’s generally just eaten up by their property tax. So, it’s really advantageous for all of our clients to pay their state income tax through their corporate legal entity, their S corp, or their building flow through entity, to basically get the full 37% deduction instead of a 0% deduction if you just paid it personally because you’re already capped basically based on your property taxes usually. 

Yeah, and by each state, there’s certain elections you have to make. I think the big thing, kind of like you said, Keith, is that if you have positive corporate income, I’d say over probably $50,000 or $75,000, you really need to make sure that you’re electing this PTE and paying part of your state income taxes through your entity or you’re losing out on tax deductions, literally losing dollars. 

Yeah. And it needs to be done before the end of the year if you want to take the tax deduction this year. So that’s the key thing here is it needs to be paid by 12/31, which for many of our clients, we’ve already told them what payment is due, but for those that don’t use us, that’s something they need to hash out. 

Yeah, 100%. You need to have your CPA, if you’re using a local CPA, be proactive and take a look at what he thinks your flow through income’s going to be, so you can get that PTE tax paid in. Because if you pay it in January, you’ll still get the deduction, but you’re getting it next year, so you’re waiting a long time for that. 

And when you pay it in through your corporate entity, a lot of clients I feel like get confused, like, “Am I paying more state income tax?” You’re not. You’re basically getting a full credit in most instances flowing through to your personal return on the state side. 

All right, so I think the next one is just good, Judson, to just highlight broadly that, listeners, you need to go make sure that you have looked at your projected W-2 or your last pay stub before the end of the year. 

There’s a lot that we can cover here, guys, but like, man, we see this all the time where something was missed throughout the year and we’re not going to grab the highest HSA deduction, or we’re not going to grab the 401(k) deferral. Like, how often do we see that missed? And it might be $500, $700, but it’s still a deduction that we’re missing. 

Yeah, and once you miss it, you miss it. Like, you get through the end of the year, if it’s only $700, you’re probably not going to want to go back and amend a W-2 and go through all that hassle. So, the stuff that needs to be done by the end of the year has to be done by the end of the year. So, a level of compliance check by your CPA or by your planner here at Cain Watters would really behoove you. 

Yeah, just go and look at what your final payroll is set to be. Make sure you max your 401(k) out, all of your other deductions. Make sure nothing gets wonky with your federal or state income withholding throughout the year, that it’s really on track there. 

But then also, Judson, I think there’s a broader conversation of also just making sure that you’re capitalizing on the QBI deduction, which, listeners, this is one that we haven’t talked about in a while, but it was made permanent by the One Big Beautiful Bill Act, and it’s this opportunity to shift the amount you’re taking from salary versus K-1 and get an additional deduction from QBI on your federal return. 

But there’s nuance to how much you take here, and it does have to be justified before the end of the year because it’s affected by how much you take in W-2. So, I think Judson, for a lot of our clients, we’ve already done this for them throughout the year. Right. But this is another process of going through and looking at your W-2 versus your K-1. 

Yeah, I think that, like you were talking about, there’s balance with how much you pay in W-2. For a lot of our clients there’s the balance with how it affects their pension plan. But if you are in a situation where your taxable income, let’s say, is going to be less than $500,000, then this QBI deduction really is one you need to look at. 

That’s for a married filing joint couple. So, if your income is going to be at that $500,000 level or below, then you can qualify for this QBI deduction, and you may not want to maximize that W-2 as much as you may. So again, it’s like that balance between tax planning, making sure you’re getting all of those things within your W-2 like you just talked about, Hunter, but also not wanting to leave deductions on the table. 

That’s right. All right. Another quick, easy one is the S corp premiums for health insurance. S corp. So, a lot of you listeners know about this one. We talk about it a lot with our clients as well. Just have to get that number at the end of the year, make sure it’s added to your W-2, get that over to your payroll company. So please don’t forget that one. 

Perhaps let’s do a little talk, but we’ll skip over this next one, and we’ll come back to it. Keith, let’s do a little talk about accelerating purchases by the end of the year. If I finance it, do I get the deduction? Do I have to pay before the end of the year? Is it placed in service? We already talked a little bit about the difference between this year and next is not that big of a deal. But how does that all work as far as when something gets to be deducted? 

Yeah, I mean, because there’s no change in the marginal rate, if you feel like your business is going to do approximately as well in 2026 as it’s going to do in 2027, there’s not a whole lot of credence to accelerating a ton of deductions, like paying supply bills in advance or paying that January rent earlier or whatever it is. 

But if you are in a situation where, like, you’re an ortho practice, you had a great year of starts, and all of a sudden you know your production’s really high, so you know those collections are coming in 2027, then it may make sense to hold back a little bit and actually move some into the next year or vice versa, just depending upon kind of what you know about your own business and what’s going to happen over the next 12 months going into 2027. 

Yeah, I think there’s so much to be said about preparedness, because if you know where you are from a tax standpoint, you have a lot better knowledge about whether you need to accelerate some expenses or whether you can defer those expenses. I think that a lot of times, clients, if they don’t really know where they’re at, they tend to want to accelerate expenses just because they don’t know, right? 

And I think that, there was an old saying, knowing’s half the, what was it? GI Joe? Knowing’s half the battle. Knowing’s half the battle. Yeah, you had it and then it just fell off. Yeah. Well, it’s late. It’s afternoon. Well, and you’re old. And I’m old. When you get old… yeah. GI Joe was a few years ago. Yeah. Grandpa Jud’s going to be an awesome one to hear some sayings from. They might be a little inappropriate from time to time. But as Hunter said, knowing is the fight of the battle. Half of it. Oh, half of it. Yeah. 

So again, listeners, this is one where regardless of when you pay for it, the asset just has to be placed in service. We go over this time and time again because that’s all that matters. Is it in your practice? Did you use it for treating a patient of any sort? And so, if you want to take the deduction in 2026, make sure that happens. Whether you finance it at 0% for 12 months, whether you finance it at 3% for 36 months, whether you pay cash for it, none of it matters. It just needs to be in your practice. 

The one subtle nuance here is that equipment companies still play this. Supply and equipment companies still play this a lot to get people to buy things, and there are discounts to be had. There are really good deals to be had. So, if this is one that’s like, “Hey, there’s a really great deal, I can get really good financing, X, Y, Z,” I do think it makes sense to accelerate if you need it anyway. 

Yeah. I highlighted one word in that whole four bullet points, and it’s the word “need.” If you need the equipment, if you need the new iTero, if you need the new cone beam, yeah, buy it. There are probably good discounts. You can accelerate the tax deduction if that’s in your best interest. But I also have a lot of clients that feel like they’re almost making money when they buy equipment at the end of the year. You’re not, because you’re going to have phantom income for the next four or five years after you do it. Your equipment supply rep can be a great salesman but make sure you need that piece of equipment. 

Does it say, “if you need or your friend has?” Right. Oh. No. Hmm. Judson, you want to do qualified leaseholds here? 

So, like, what if people did renovations this year? What if they’re not done yet? Do we get to take deductions for those? If you’re not done… So, the IRS says that basically assets have to be placed in service. So, if you have a renovation, if you have a new building, anything like that, you essentially have to be moved in and using those assets to take them, okay? 

I think the big thing on these leaseholds is if you remember back, because all of you have listened to our tax planning podcast over the last few years, leasehold improvements and how much you could take in the first year, otherwise known as bonus, was on this declining scale where it was like we could take 100% and then 80% and then 60%, and then with the OBBB, they said, “You know what? 100% bonus is in effect. It’s permanent.” So now you can write off 100% of your leaseholds. 

What I think really matters here is that most of the time for our clients, if they have a decent amount of leaseholds in place, that probably means they also have equipment, they probably have different types of things in, because you’ve done some sort of renovation or new addition. 

What’s important here is that there’s a lot of ways you can tackle this, and what you may want to do is not lean on the Section 179 and lean on the bonus depreciation, because that’s going to maximize what you can take over the next five years as opposed to the next 15 years, right? So, it’s all this balancing act. 

And really that just goes back to having a plan, right? I think with a lot of our clients, we’ve talked to them about this already. If the renovation’s big enough, we’ve recommended something called a cost segregation study, which can be highly beneficial. But you don’t want to go into a big renovation without a plan of what this looks like. 

I think I’m going to come up with a new tagline, “Having a plan is 56.5% of the battle” I like it. Judson Crawford. Yeah. It’s true, though. Okay. So- GI Judson. Oh, no. No, no, no, old man. We’re not calling you that. 

So maybe we’ll talk a little bit, we’ll go back to this point, a little DB plan talk. So, folks might have considered in the past, Keith, like an additional pension plan, which we’re not going to go into the specifics on these, because we’ve talked about them at length, but like a cash balance or defined benefit plan, and sometimes I think they’re like, “Oh, I can’t set that up because it’s the end of the year.” You actually still can, right? 

Yeah, you actually can, and you can even set up a DB plan for 2026 in 2027. Whoa. Mind blown. Yeah, so you have a lot of time there, but setting up a DB plan is not “Hey, I’m sitting on a lot of money right now, I want to fund this for one year, get some tax deductions, and then move on with my life,” because when you go into a DB plan, you’re there for a presumption of 10 years. 

You’re going to have a serious relationship with this plan. You are. You’re going to get to know it really well. But the dollars you can save over that longer term period of time is significant. So, if you know that you have the cash flow and you want to save taxes over a longer period of time and want to save for retirement, they can be highly beneficial. 

Highly beneficial, but you also have to look at it… you want to have a DB plan that you’re funding $100,000, $80,000 minimum. You want to be putting some significant dollars in there because they also come with a pretty high admin cost, right? That’s correct. If you’re only putting $30,000 additional into a DB plan, that’s probably not really helping you out once you factor in admin costs and all that, so. Yep. 

Okay we are almost to the SECURE Act 2.0, folks. I know you’re super excited, and Keith is going to roll up his sleeves and be ready to talk about that. But while he does, last thing before the end of the year, if you had any personal expenses that you paid that should be business expenses, right? 

So maybe it’s like, “oops, I picked out the wrong credit card,” or “I had to use a personal check for that.” You know what a check is, Judson? It’s been a while since we’ve seen those. I wrote three today. No, you didn’t. I swear. And then put a stamp in an envelope? You have no idea. Okay. If you wrote a personal check and you need to pick that up for business, make sure and reimburse yourself through your business entity. 

Keith, SECURE Act 2.0, you are up. What do people need to know? Yeah, so- What do they need to know about SECURE Act 2… Stop. We’re not doing this. t’s been a long day for me, Judson. 

So, the vast majority of the SECURE Act 2.0 changes have already come online but just wanted to highlight a few things that are still relatively new and if you haven’t listened to the podcast in a year or two or you missed this one last year, just make sure you’re aware of them. 

If you do start up a 401(k) plan and you have fewer than 50 employees, you’re going to get some startup credit, so make sure your CPA knows. Typically, we will know if you set that up if you’re working with us on that, and we’ll be able to take those credits for you. Those credits kind of diminish down as you get over 50 employees. 

But also, if you have a SIMPLE IRA or a SEP IRA, you do have the ability to do Roth in either of those categories. But what we’re finding is a lot of financial institutions, the custodian of that money isn’t set up to track your Roth contributions, so you have to check with your financial custodian there on the Roth stuff and make sure they’re equipped to handle it. 

The big one on the 401(k) deferrals, if you’re over 50, you get an extra $8,000 catch-up contribution. If you made under $150,000 last year, you have the option to treat that as either traditional or Roth. If you made over $150,000, it must be Roth. And then you also still have the strange super catch-up, as I call it, if you’re aged 60 to 63, so for those four years that maximum catch-up contribution increases to $11,250. 

Yeah, so there’s a lot of nuances there, listeners. You can take this just very simply. If you’re over 50, you double need to check your W-2. Make sure the catch-up is on there. Make sure it’s being treated correctly between Roth and pre-tax, and also, incidentally, that your tax projection that your CPA is preparing includes that proper treatment. 

Because if your CPA is saying, “Oh, that catch-up’s pre-tax,” and you made over $150,000, it will not be, and that will be a tax surprise for you. So, if you’re over 50, whether it’s the catch-up or super catch-up, you need to double, double-check this number. 

So, let’s move on to some personal tax planning, guys, and Judson, there’s new, new, new information. There is new information for 2026, and if you haven’t seen it, there’s been a lot of chatter about it recently. We’ve talked about it on the podcast quite a while ago, but we now have these things called Trump accounts. That’s right. So, on the Trump account, the reason it is something that we’re bringing up here is you do, again, have the opportunity for each kid to get $5,000 contributed in there by employers, family, friends, Michael Dell, Judson Crawford, all those different types of people, so. 

But that $5,000 is by the end of the year. It’s only up till age 18, so my oldest and unfortunately, my middle also do not qualify for that. But I think this is one… there’s some creative opportunity maybe for, like, grandparents for Christmas to contribute into kiddos’ accounts, their grandkids’ accounts and things like that. Even if it’s a couple of hundred bucks, that’s a big win. 

Yeah, I think the big change here when you boil it down, is that this allows you to get money for your kids in a tax-advantaged environment without them having any wages, without them being an employee somewhere, which is not something that’s been available before this. 

Some of our clients, their kids get wages through their business or other places, and so they’ve been funding a Roth IRA, but this is for those that don’t. Yeah, and it’s also extra if you want to do that as well. That’s right. I mean, it’s an opportunity to do both if you’ve got the cash flow around and the grandparents want to contribute in. 

I just want to say, listeners, that if you have not set one up for your child under 18, you have to go do this, alright? We are seeing clients’ kiddos that are getting real dollars from benefactors who are contributing by zip code, by state, where you pull up your kid’s Trump account and there’s $100 from Michael Dell in there. 

I don’t care what your politics are, you have to go set one up. The app is incredible. Go set it up. This is opportunity for your kiddos to get money from others as well as yourself. And maybe we’ll do a little deep dive in the future, Judson, on the four different types of kiddos accounts. That could be a fun episode. We probably should. It’s time for a review of that. Yeah. 

Let’s do a little charity. That’s a popular thing for our clients, Keith, to do at year end. It’s a good thing. It’s a good thing. It’s a very good thing, as Ebenezer Scrooge would tell you at some point in that play. 

So, let’s break this down a little bit. Let’s first just talk about the changes to donor-advised funds, and then we’ll go to kind of the next – because there are a lot of changes to charitable giving. Yeah. So, what’s the big change to donor-advised funds for those that have them? 

Yeah, so essentially, 2025 was the best year to fund your DAF. Right now, they’ve put some limits on it where you just can’t do as much in your DAF. If you do a cash contribution, that’s capped at 60% of your AGI, so you have to know what your AGI is or an estimate of what your AGI is going to be and then make sure you don’t do above that 60% limit, or you’re not going to get the deduction you think you’re getting. 

And with appreciated assets, i.e. stocks, which are really powerful to put into these DAFs, right? Because you avoid capital gains tax and get the deduction, right? So those are capped at 30% of your AGI. So, they have put some parameters on this to kind of slow down the amount you can put into a DAF. 

And I’d like to make a personal announcement for all of the planners here at Cain Watters. Please don’t email your planner on December 15th and say that you’d like to contribute stock to a charity or a DAF. It does take a little bit of work to just get the lot numbers and get it contributed over. I think right now is a great time. As you’re listening to this, if you want to give charitably through appreciated stock, right now would be a great time to shoot a note over to your planner. They can adequately prepare. 

Now the reason we do that, folks, is let’s say that you bought Nvidia at $1,000 and now it’s worth $20,000. You’re avoiding that $19,000 gain, and you get a $20,000 tax deduction against your income for the donation of that stock. You cannot sell the stock and then give the money. You have to actually physically give the stock. 

Now if you’re wondering for a second, does a charity that I contribute to, church, school, something else… do they have the ability to take stock? Absolutely. Every single one of them do at this point because this is a very common way to give. Now the really nice part is that you can then just take the $20,000 you were going to give in cash and refund that and buy Nvidia back in, and so effectively you’ve reset your basis and taken a tax deduction for it. Super helpful, but you can’t do it, Judson, in like a day or two. Nope. Takes time. It is a process, so.  

I guess the last thing here, Keith, is there’s now a reduction of charitable giving for the year, correct? Yeah, there’s a floor, right? So, you have to clear that floor of 0.5% of your AGI on any charitable giving you do. So, I agree with you, Hunter, when you said charitable giving’s a good thing, but they’ve kind of made it not as tax advantaged as it has been in the past. 

Yeah, and I think the big thing here is that you just need to understand what that effects on your own income and especially if you’re approaching the end of the year and you’re thinking, “Oh, I may give a few thousand dollars in order to save taxes,” you really need to know where you’re at because if you haven’t already hit that 0.5% AGI floor, you may not be getting a deduction on this. 

That’s right. Hey Judson, what’s 0.5% of your AGI? It’s like $7. Okay. That was quick math you just did in your head. Yeah, I was thinking about it. $7 million times 0.5 I think is more than $7. I don’t do math. 

All right, Keith, let’s talk about tax payments. So, like we know that there’s potential penalties that arise If people don’t pay taxes on time. So again, listeners, you can pay taxes in really two ways on the federal side: through your W-2 withholdings and then also through estimated payments. 

Now, the IRS requires that you pay that evenly throughout the year. W-2, they can’t really figure out when you did, so they just look at the number and they apply it evenly. So that’s why we say we really recommend going in and checking your W-2 and making sure that is appropriate from a tax withholding standpoint. 

But then you also have these quarterly payments that have to go throughout the year as well, and in order to reach that safe basis, we have to get prepared, Keith, because they got a payment in January, right? 

Right. Yeah, so basically, you’re exactly right, Hunter. I mean, if I have a client right now that I do their tax projection here in late October, early November, and I still have the ability, if they’re behind on taxes, to increase their withholding, well, then I’m going to take that opportunity to increase their withholding because, like you said, the IRS is going to treat that as if it was paid in evenly throughout the year. 

 If you wind up having to make, say you made $30,000 quarterly tax payments Q2, Q3, you get to Q4, all of a sudden, it’s $70,000 because you grew, well, now you’re going to get hit with a little bit of interest and penalties on that $70,000. So, if you could keep it at $30,000, increase their federal withholding by $40,000, you’re going to wind up in a much better place. So, there’s a little bit of strategery there that you need to take into consideration. 

That’s not a real word, but I like it. It is. All right. You want to do backdoor Roth IRAs, Judson? Yes, I would think that by now many of our listeners would know and probably have participated in a backdoor Roth IRA, but you have until April of every year to fund your IRA, and therefore then do the conversion. 

But we like our clients often to do this before December 31 so that your IRA contribution and your conversion match every year. There is actually a tax form that needs to be filed with this by your CPA if you’re doing these conversions and sometimes it makes it easier if you have a contribution and the conversion within the same year. 

So, it’s always a good thing. We say if you have the cash flow, it’s a good thing to get that contribution and conversion done early as possible and get it invested anyways. So, while you have until April 15th to do that, it may be a good thing for record-keeping if you consistently do it by the end of the year every year. 

All right, we are almost there. We have two more, and these are amazing ones, folks, so you need to listen in. Now, Keith, I hear you like golf. You’re not very good at it, but I hear you like it. Shots fired. Two-time defending champion. Oh, wait. Yeah, yeah. Oh, sorry about that. Yeah, you are pretty good, I guess. 

Have you ever been to Augusta before? I have never been to Augusta. Whoa, somebody doesn’t like golf. But I do love the fact that this thing is called the Augusta Rule. All right, well, what is it? Because it’s named after the greatest golf tournament in the world. 

So, the Augusta Rule is essentially a tax court case that came up when people in Augusta leave Augusta during the Masters Golf Tournament and rent their house out. And essentially the IRS allows you to rent out your home for 14 days tax-free. That sounds fun. It is fun. 

So essentially, if your business, if you’re hosting parties for your staff and things like that at your house, you can pay a modest amount of rent. You can do it up to 14 times. If you do it the 15th time, then it becomes taxable, but if you do it less than 14 times, you can basically get a deduction on the business side, but you’re not picking up the income on the personal side. 

That’s right. And I think for most of our clients, what we would say is that it’s going to be a lot easier. Obviously, you need to have these rental incomes before the end of the year, and you need to have your records on what those days are used for. That’s right. 

All right, last but not least is tax loss harvesting. So, if you’ve listened at all, listeners, this year the market has been volatile. It’s overall up, but a lot of stuff is not up, and so you might have holdings in your accounts that are down. It’s a good opportunity to sell those holdings, recognize a capital loss that could be used to offset a capital gain somewhere in your life, maybe the sale of a building or a sale of another piece of stock or your business or something like that. 

So again, that’s something that’s an individual decision on various holdings, but you would want to do that before the end of the year to lock them in. It’s a good time to review your investments, see what’s going on. That’s right. 

Well, listeners, if you have loved this as much as we have, there’s more, but you have to go to the blog post, right, Judson? That’s right. Once again, look for Keith Klein’s blog post, which is called “2026 End of Year Tax Moves to Consider.” Thanks, Keith. Thanks for having me, guys. Appreciate it. 

Well, the best way to keep up with this is to subscribe to this podcast. That way, you never have to miss an episode, and you can go back and listen to all the others. If you’re enjoying it so far, leave us a review. If you have a question, comment, or suggestion for a future episode, drop us a line at cainwatters.com/wealth. We really do answer these. And if you want to learn more about what we do when we’re not recording these episodes, visit cainwatters.com to see how we’re helping almost 4,000 clients reach their long-term financial goals. 

And war, what is it good for? Absolutely nothing. But if you have a little knowing of something, you have 50% chance that you’ll win a battle. G.I. Joe. 56.5. 

Timestamps

01:02 – Keith Klein Intro 

01:39 – No Major Rate Changes 

02:36 – 1099 Threshold Update 

03:50 – PTE Tax Election 

05:39 – W2 Check and QBI 

08:06 – S Corp Health Premiums 

08:27 – Equipment Timing Rules 

11:42 – Leaseholds and Bonus Depreciation 

13:39 – Defined Benefit Plans 

14:56 – SECURE Act 2.0 Updates 

17:41 – Trump Accounts for Kids 

19:46 – Charitable Giving Changes 

22:52 – Avoid Underpayment Penalties 

24:24 – Backdoor Roth Timing 

25:17 – Augusta Rule and Loss Harvesting 

Have questions or ideas for Hunter and Judson? Reach out at cainwatters.com/wealth. Don’t miss an episode, subscribe and leave the guys a review on Apple Podcast, Spotify, or wherever you listen.

Judson Crawford
CPA, Partner
Since joining CWA in 2004, Judson has helped clients navigate the path to financial freedom for themselves, their families, and generations to come. As a partner, Judson advises clients and hosts the popular Accumulating Wealth podcast.

Cain Watters is a Registered Investment Advisor.  Cain Watters only conducts business in states where it is properly registered or is excluded from registration requirements. Registration is not an endorsement of the firm by securities regulators and does not mean the adviser has achieved a specific level of skill or ability.  Request Form ADV Part 2A for a complete description of Cain Watters investment advisory services. Diversification does not ensure a profit and may not protect against loss in declining markets.  Past performance is not an indicator of future results. 

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