Most people only think about taxes twice a year: while filing, and while dreading filing next time. That gap is exactly where expensive surprises are born. Today’s episode is a genuine mid-year tax tune-up, the kind of checkup that takes maybe twenty minutes and can quietly save you from an ugly bill, an unexpected penalty, or a refund that wasn’t actually a win. No jargon-heavy lecture, just a clear walkthrough of what to check right now while there’s still time to fix it.
What You’ll Walk Away With
- Why a big tax refund last year tells you almost nothing about whether you’re on track this year
- The four numbers you actually need to know to build your own mini tax forecast in one sitting
- How the IRS “safe harbor” rule works, and the two different percentage thresholds that keep you penalty-free
- A common myth about side hustle income that trips up more people than you’d expect
- Why switching to a Roth 401k without a plan can quietly blow a hole in your monthly cash flow
- The real math behind donor-advised funds, and why writing a check to charity may be leaving money on the table
- A simple gut-check for figuring out whether you need a professional or can handle a financial fix yourself
Why This Matters Now
In your 40s, your financial life usually gets more complicated before it gets simpler: a raise here, a side hustle there, maybe two incomes in the household, maybe a bonus that shows up at an inconvenient time. Each of those changes quietly shifts what you owe, and waiting until April to notice means you’ve lost your best chance to do anything about it. A twenty-minute check now isn’t about becoming a tax expert. It’s about making sure next spring is boring instead of stressful, which, when it comes to taxes, is exactly the goal.
From the Basement
A home AC disaster turns into an unexpectedly useful lesson about getting a second opinion before writing a big check, whether it’s for a repair, a service, or apparently, a $3,000 HVAC estimate that turned out to be a $300 fix. Consider it a bonus lesson in trusting your gut when something doesn’t add up.
Resources Mentioned
IRS Estimated Tax Payments — where to make an estimated payment directly
Stacking Benjamins Tax Guide — free guide for organizing your mid-year tax review
Stacko Financial Action Month board — the interactive game with a money move for each day
Field Kit Finance — track net worth, spending, and subscriptions in one place
Daffy — donor-advised fund platform referenced for charitable giving strategy
Our Headline
Doug’s Trivia
- What money-related profession did Martha Stewart have before becoming a television icon?
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Other Mentions
- Donor Advised Funds 101 (with Adam Nash) (SB1724)
- Stacking Benjamins Tax Planning Guide
- Stacking Benjamins Field Kit » The Stacking Benjamins Show
- Free Personal Finance Cheat Sheets
Join Us Wednesday
Tune in on Wednesday when we’ll help make bad budgets good and good budgets great with the king of budgeting, Jesse Meacham.
Written by: Kevin Bailey
Miss our last show? Listen here: Why Smart People Make Dumb Money Decisions (SB1877) | Stacking Benjamins
Episode transcript
[00:00:00] Joe: It is Monday in mom’s basement, and that means OG just took a sip of coffee. I’m about to take another sip of coffee. Doug, you got the coffee out?
[00:00:07] Doug: I’ve already had three, and I am so amped up.
[00:00:10] Joe: This is … It’s gonna be a bad day, OG.
[00:00:12] Doug: It’s … Yeah. These people need to listen fast because my mouth’s gonna be moving.
[00:00:17] Joe: The words we don’t wanna hear Doug say is, “I’ve already had three.” Yeah. Like, that is, that is bad news. What’s good news, though, is that at the beginning of every week, we toast the people that kept us safe all weekend, the people who’ve been working a lot of, lot of overtime to keep us safe, men and women in our armed forces.
[00:00:34] Joe: So raise your mugs, Stackers. On behalf of the men and women making podcast in mom’s basement and the men and women stack of Benjamins across the world, here’s to you. Thank you so much for all you do. Let’s go stack some Benjamins together now, shall we?
[00:00:48] Doug: Thanks, everybody. Uh-oh. Sounds like somebody’s got a case of the Mondays.
[00:00:59] Doug: Live from Joe’s mom’s basement, it’s The Stacking Benjamins Show.
[00:01:14] Doug: I’m Joe’s mom’s neighbor, Doug, and how’s your tax situation looking? I know what you’re thinking, “Doug, it’s only August.” And I say to you, “Hey person I made up for this open, you should think about taxes now so that it’s all great next April.” So on today’s show, it’s your just past midyear tax checkup. What should you toggle to get the best tax treatment on your money?
[00:01:35] Doug: We’ll share. And that’s not all, it’s Financial Action Month, so we’ll take one square from the Staco game board and help you make an easy and profitable money move. And even with all that, I’ll still save time for some of my trivia you can brag about to your friends, because everybody loves when you bring up random facts out of nowhere, right?
[00:01:57] Doug: At least that’s what I find. And now, two guys who are probably sitting around bragging that they get to work with this guy, it’s Joe and O-G-G-G-G.
[00:02:11] Joe: That’s right Stackers, welcome to the place where I sit here and pinch myself, ’cause I get to sit next to Doug. It is the Stacking Benjamins show. We’re super happy that you’re here.
[00:02:20] Joe: It is Monday, we’re getting nerdy today OG, ’cause it is midyear, just past midyear tax evaluation, tax planning in mom’s basement.
[00:02:32] OG: You could see my desk right now. I’ve got, uh…
[00:02:36] Joe: Got all the tax stuff ready to go.
[00:02:38] OG: Yeah. Sucks.
[00:02:40] Joe: It does suck. But you know what’s cool is, it sucks a lot less if you handle it now, if you handle it today, and we’re gonna get into this in a little bit.
[00:02:48] Joe: Wait,
[00:02:48] OG: you’re talking about 25 taxes that are on extension, right?
[00:02:51] Joe: Uh, I am not. ‘
[00:02:52] OG: Cause that’s what I’m dealing with. I mean, is there something I’m supposed to be doing besides that? ‘Cause I got till, you know, this is what, ear- early August-ish. I got till October to get this done. Are you telling me there’s something else I’m supposed to be doing on my taxes besides this?
[00:03:06] Joe: Believe it or not- Say it ain’t so … we’re gonna talk 2026 on today’s show. So- Oh, boy … uh, Stackers, get ready to make some moves. Get your documents out. We’re gonna talk about exactly what you should get out, and, uh, how to maybe, maybe tweak a little bit, uh, so that you don’t have to do some big tweaking next April.
[00:03:26] Joe: Hey, it is Financial Action Month. We’re kicking it off with today’s show. You can get your name submitted to win a copy of Stacked, my book, pretty comprehensive book, about how to do your financial plan. You’ll find that at stackingbenjamins.com/staco, because the big thing is Staco, that’s the game we play, it’s like bingo, where you can take different financial actions.
[00:03:49] Joe: We’re gonna walk through one of those, Doug, as you mentioned earlier, walk through one of those today. So a lot on tap. We’re gonna get right into it, but first we got a couple sponsors who help us keep on keeping on. We’re gonna hear from them, and then we are going to do some midyear tax planning. Let’s get it rolling
[00:04:08] headlines: Hello, darlings.
[00:04:10] headlines: And now
[00:04:15] Joe: it’s time for your favorite part of the show, our Stacking Benjamins headlines Guys, I came across a Kiplinger piece from senior tax editor Kelly R. Taylor about mid-year tax planning, and my first reaction was probably the same as yours. We just finished taxes. Heard from OG. I’m still working on taxes.
[00:04:28] Joe: Why are we bringing them back into the basement? Didn’t Doug put the tax records in a grocery bag marked “Do not open until panic season”?
[00:04:36] Doug: Panic season.
[00:04:38] Joe: Doug, where do you keep your tax documents?
[00:04:41] Doug: All right. So in all seriousness, I do have a… Uh, there aren’t many documents that you keep anymore, like actual paper documents.
[00:04:48] Doug: There not many you get. So I, you know, I have a… For the few that I might get, I’ve got a old-school manila folder that sits in a spot on my desk or, you know, in my desk, and that goes there. And then I just create a digital file folder and throw stuff in there as they come.
[00:05:06] Joe: It’s perfect. It’s all password protected with the password being password?
[00:05:09] Doug: Oh, yeah. 123.
[00:05:10] Joe: Yeah. It’s like the Louvre making Louvre their password.
[00:05:15] Doug: And putting the really valuable stuff right near the window.
[00:05:18] Joe: So you just can’t make it up. But this piece makes a great point. The best time to make tax decisions isn’t when you’re filing the return, because by then the year’s closed. So today, uh, we’re gonna create your mid-year tax checkup.
[00:05:33] Joe: We aren’t preparing anybody’s return. We’re gonna figure out whether a tax surprise might be coming and what we can still do about it. So the first half, we’re gonna try to make sure there are no surprises. In the second half, we’ll talk about some cool tax planning techniques. And by the way, before we start this, I should do the, uh, disclaimer.
[00:05:50] Joe: I should have, Doug, sent you the disclaimer for you to read that federal taxes are complicated. State rules are different. Major transactions deserve help from a qualified tax professional. This is for entertainment purposes only. How’s that? Is that good?
[00:06:02] Doug: It was okay. I mean, but now we know why I’m here.
[00:06:05] Joe: We do. All right, what are, what are the questions we ask? Because at this point in the year, OG, what we want to do is we want to build a forecast, right? What do we need to gather before we start making tax moves?
[00:06:19] OG: Oh, well, this is something that we actually tackle every second half of the year for clients.
[00:06:24] OG: This is one of the kind of standing review segments in our planning year. What are the things that we look for? Uh, well, we look for obviously your completed 2025 return, you know, because that’s the basis for all of the changes from ’25 to ’26, right? Because you’ve got really accurate data from ’25, clearly, because you just filed it, and that’s the starting point.
[00:06:48] OG: The 2025 return is, you know, the basis for here’s all the changes we’re going to make, you know, or the changes that, that can happen from ’25 to ’26, and it’s a good barometer for where you’re at relative to where you were pacing this time last year. So we know where ’25 is. The next thing we want to look at is all of your pay stubs and income earnings for this year Obviously forecast that out for the rest of the year.
[00:07:11] OG: If you get paid a bonus in the second half of the year, maybe that’s a little harder to guesstimate what it’s gonna be, but by this time maybe you have some idea of what that is. And then the other piece is what are the other tax things that you’ve done so far this year that we need to be aware of? Did you make any charitable contributions?
[00:07:27] OG: Did, have you paid, uh, property taxes or real estate taxes? Have you done any capital transactions? Did you buy or sell any property, any stock? Have you done any conversions? Are you thinking about doing any conversions? Most people honestly wait until the end of the year for that, or should wait until the end of the year.
[00:07:43] OG: But that just gives us a basis of, like, where all the bodies are buried right now.
[00:07:46] Joe: Yeah.
[00:07:46] OG: And now you get to start trying to manipulate that data for the next six months to figure out, you know, what, what kind of changes we need to be.
[00:07:53] Joe: Yeah, I like everything that you said, and in my head I’m breaking those up kind of into four things.
[00:07:59] Joe: First is, based on last year and where I am this year, how much money do I expect to make? If you think the business is going well this year and you get bonuses, my bonus is gonna be about the same. Those are the hard parts, as you know, OG. These lumpy one-offs can change things, but we gotta look at what the expected full year income.
[00:08:18] Joe: So I love the fact that you go back, look at last year compared to where you were at this point last year. How does it look? Second, your expected deductions and credits that you’re gonna get. Third, how much tax do I think I’m gonna pay? And then fourth, how much have I already paid? So have I, have I already paid enough in to make sure that I’m gonna be okay?
[00:08:39] Joe: Because a big thing that happens, OG, one thing that happens is people assume if I got a big tax refund last year, well, then I’m good. You know, without going through the stuff that you talked about. They’re like, “Oh, I’m good. I got a big refund last year.”
[00:08:53] OG: Yeah. Well, maybe you got a big refund because you got a, a one-off bonus, and they withheld it appropriate.
[00:08:58] OG: Actually, more likely than not, while tax surprises on the upside are annoying, um, obviously the more- detrimental tax surprise is the one where you owe money that you didn’t expect. And a lot of times people will say things like, “They tax my bonus at a higher rate.” No, all of your income is taxed at the same rate.
[00:09:18] OG: It’s just, you know, well, not all the same rate, but it’s the same schedule, right? It’s just they withhold it at a different rate. Either, either they’re obligated to because of how it’s coded in the IRS, or they do it as a, as a favor to you because, you know, they know, like, if you don’t, uh, we know how much money you make ’cause we pay you every day, so- This
[00:09:37] Joe: could end badly if you don’t
[00:09:38] OG: yeah, if we don’t take out 40% of this, you’re gonna owe a big chunk of it on the back end, and it never feels great. But you gotta account for that, you know, every year, and once you’ve build the baseline for that, you know, that data, then if you do have a one-off surprise, you know, it’s October 20th and your boss goes, “Hey, here’s a bonus for 20 grand,” you’re like, “Oh, great.
[00:09:58] OG: Thanks, I guess,” you know, you can just add that line item into your model and, and figure out where you’re gonna be.
[00:10:04] Joe: Well, and that is, and I love that you went there, ’cause this is really where I wanna go next, which is having that big refund, okay, to your point, that’s fine. But There are two questions that people should be asking, and they’re not the same question.
[00:10:20] Joe: Number one is, how much will I still owe? Am I gonna owe, do I project that I’m seeing that I’m gonna owe, and how much will that be? And then second, and this is a different question, will I face an underpayment penalty? Because I think a lot of people don’t realize, OG, that if you don’t stay close enough, you’re going to run afoul of what’s called the Federal Safe Harbor.
[00:10:39] Joe: You’re gonna have a penalty because throughout the year you didn’t withhold enough. Can we talk about that a second? What, how does this penalty work?
[00:10:46] OG: Yeah, penalties suck in everything, sporting events- … tax events. Generally speaking, the yellow card or red card is a really bad thing to get, you know?
[00:10:56] Doug: Dating.
[00:10:57] OG: A dating penalty?
[00:10:59] Joe: Yeah. Can you see having an IRS agent come to your house, and he stands there in front of you and doesn’t say anything, and then, like the soccer ref, he just puts up the red card?
[00:11:08] OG: I mean, that would be bad. You’d be like, “Oh,
[00:11:10] Joe: no!” No, no, no, no, no. Throws this
[00:11:11] Doug: yellow handkerchief at your front door.
[00:11:14] Joe: You’re, you’re-
[00:11:14] OG: You just hear, like, tweet, tweet, tweet, tweet, tweet, tweet, tweet. Like, as this big, big flag comes your way. Be
[00:11:18] Joe: like, “Please don’t, please don’t, please don’t.” Red card, oh, crap.
[00:11:21] OG: Prior to the tax withholding. Personal foul- … not withholding enough on that guy. Yeah, penalties suck, man. Um, and if you can avoid them, the better, better you are.
[00:11:34] OG: The IRS assumes that you earn a consistent income throughout the year. So if you say that you make 100 grand, if your W-2 says 100 grand, they assume that you earn that in $8,000 increments every month. And so your, your withholding account, your tax payments should match that level of income. Now, the reality is, is that sometimes we don’t earn money that way, and then it’s incumbent on you to tell your CPA or to tell the IRS that, “Hey, I di- I didn’t earn 200 grand evenly throughout the year.
[00:12:05] OG: I earned 100 evenly throughout the year, and then literally on December 28th, I got a check for 100 grand.” Now, that buys you out of that tax penalty problem to some degree, but you still have to have the withholding in by, you know, those quarterly estimated payments, which is also kind of stupid, because it’s not really quarterly.
[00:12:25] OG: And I just, I as a taxpayer/business owner just cannot understand how someone set this up and then called it- Oh, it’s horrible … quarterly.
[00:12:35] Joe: So horrible.
[00:12:36] OG: And no one has ever challenged this. Like, no one has… Or maybe they have, and they just don’t win. But your taxes are due January 15th. That is for Q4 of the prior year, your tax withholding payments, I should say, uh, if you’re self-employed, something like that.
[00:12:51] OG: April 15th for Q1- Okay. Stands to reason that’s in the ballpark Also April 15th for any mistakes from the prior year. O- o- okay. You know, kind of self-inflicted, I guess maybe, but it’s a big day. June 15th, because that-
[00:13:14] Joe: Right. ‘Cause we feel like it. ‘Cause somebody doesn’t know math.
[00:13:18] OG: And September 15th, because that also…
[00:13:24] OG: Yeah. But then your taxes are due October 15th if you filed an extension, or September 15th if, you know, anyways, it’s, um-
[00:13:32] Doug: So my takeaway from this is it’s just always tax day. There’s just always a tax dl- deadline.
[00:13:36] OG: It certainly feels like that if you’re a business owner, I can tell you. So the way that you avoid the tax penalty on your personal income tax side is one of two things.
[00:13:44] OG: You can either withhold 110% of last year’s tax bill. So there’s a line item on your tax form on the second page that says, “This is your total tax.” And that number is whatever it is, and now you’ve withheld more than that or less than that, and that’s how they calculate your refund or your tax bill due.
[00:14:02] OG: But that number, this is your total tax number. If you multiply that by 110%, that gives you what’s called your safe harbor number for next year. So as long as you hit that, you’re good. And you know, look, if you go win the lottery, and you make $77 million in Powerball, and you underwithhold, as long as you’re at 110% of last year’s, you’re not gonna have a pen- you’re gonna still owe the taxes, but you’re not gonna have a penalty due.
[00:14:25] Joe: Yeah, when you say you’re good, it doesn’t mean you’ve paid the right amount of tax, it means you’re not gonna get the penalty.
[00:14:30] OG: You’re not gonna get a penalty.
[00:14:31] Joe: Just to be clear.
[00:14:31] OG: The second way to avoid the penalty is to withhold 90% of your total liability In that example of having a large income or maybe your income was high last year, now it’s smaller this year, so you’re like, “Well, I’m gonna totally hit the 110 if, if I did that, but I’m not gonna make as much money,” you still have to have 90% of your liability.
[00:14:51] OG: So this requires a little bit of planning. So those are the two numbers. Usually what your CPA does or what TurboTax does when you fill out your taxes is it prints off coupons for your tax withholding for those due dates. That is basically 110% divided by those four, four payments, you know, and, uh, you know, the first one due April, and then, uh, June, September, and then October.
[00:15:14] OG: But a good rule of thumb is to definitely check it in July, August time period, see where you’re at, run that model like we were talking about, and then you give yourself September, October… There’s no rule that says you have to pay it in September, or I should say can only pay it in September or January.
[00:15:31] OG: You can jump online and be like, “Hey, my, my bonus paid in August and I’ve, you know, I need to get this money, this extra money that I know I’m gonna owe sent to the IRS, get it out of my hands,” basically. You just go online and IRS.gov and make estimated payment.
[00:15:46] Joe: Yeah, I know people that like that. The second that they get it, just get rid of it so there’s no-
[00:15:51] OG: Just, just ship it to the IRS.
[00:15:52] OG: You’re gonna owe the money anyway. You know, and I get the whole argument that people have about like, “Well, I could put this money in my account and earn the 3%.” You can. You’re right.
[00:16:01] Joe: There’s, there’s a lot of know yourself in this.
[00:16:03] OG: Or you will spend it, and then April will come around and you’ll be like, “Ah, crap.
[00:16:08] OG: Now I have a payment plan, I’m under withheld, I owe interest- Yeah … I owe penalties.” It can get pricey in a hurry.
[00:16:15] Joe: Doug, let’s turn this into a game
[00:16:17] Doug: I, I’m terrified of this every episode, Joe …
[00:16:20] Joe: you’re going to have the ruling. But Doug, I’m gonna give you a statement. You tell me whether it’s a useful tax move or a myth we need to bury behind the water heater.
[00:16:28] Joe: Ready?
[00:16:29] Doug: Okay.
[00:16:31] Joe: I received a raise or I changed jobs, so I should review my withholding. Tax move or tax myth?
[00:16:39] Doug: Useful move.
[00:16:41] Joe: Yeah. What other changes, OG, should make us think, “You know what? I should probably look at my withholding,” besides a raise or change in jobs?
[00:16:50] OG: Well, I think where people, uh, make some mistakes here is if they have more than one job, and together those jobs make good income, but each one individually maybe is a little bit lower.
[00:17:02] OG: The math will say, you know, oh, the first $10,000 taxed at this rate- Oh … and so and so forth. And so- They don’t think
[00:17:07] Joe: about the fact you’ve got two jobs.
[00:17:09] OG: Yeah. So the W-4 does ask you that opportunity. It does give you that opportunity to fill in that information so that the, the correct column basically is used in your withholding.
[00:17:20] OG: That’s a mistake, I think, on the downside. I think on the upside, you know, obviously, if you have kids, if you get married, uh, if you get divorced, family life events are gonna have an impact on which boxes you check. If you turn 65, you know, you get to check a box. You guys, you know, it’s coming. So you get a few extra bucks.
[00:17:38] OG: Those are probably the biggest ones.
[00:17:40] Joe: Yeah. The only other one I can think of that we talked about earlier was the bonus, right? You get a big unexpected bonus, and you’re like, “Oh, maybe I need to look at- Yeah … what was withheld there. But yeah. Question two, Doug: I received a big refund last year, so my withholding must be correct this year.
[00:17:58] Joe: Uh,
[00:18:00] Doug: no, I’m gonna say myth.
[00:18:01] Joe: It is a myth. Last year’s refund tells us what happened the last year. Doesn’t matter toward this year. A lot of things could’ve changed. Question three: I can make one giant estimated payment in December and automatically erase any earlier underpayment penalty.
[00:18:18] Doug: No. The years are…
[00:18:19] Doug: That’s a myth, right? The years are totally separate.
[00:18:21] Joe: OG?
[00:18:22] Doug: If I heard your question correctly.
[00:18:23] OG: Um, yeah, no, that would be bad. I mean, you could do it if your income is lumpy like that. But if it’s relatively uniform, you will be, uh, surprise, surprise, surprise.
[00:18:36] Joe: Yeah. Round four, question four: increasing your withholding late in the year may work differently from making a late estimated payment.
[00:18:48] Doug: Uh, increasing and holding late in the year works differently. I, I’m gonna say useful, but I don’t know.
[00:18:57] Joe: That’s a tax move. That’s some good tax planning going on there, OG, I think.
[00:19:00] OG: I mean, you should evaluate it, and if you are under withholding and it’s the middle of the year and you can crank that up a little bit, that’ll, that’ll definitely help.
[00:19:08] Joe: That’s why we’re doing this, uh, show right now. Question five, “My side hustle earned a profit, but I left the money in the business checking account so I don’t have to pay a tax on it.” A f- …
[00:19:20] Doug: No. That’s, that’s not how that works.
[00:19:25] Joe: You’ve seen that before though, OG. Just tell me there’s no way you haven’t seen somebody think that.
[00:19:29] Joe: “Well, I’m just gonna leave it in the business so I’m not personally taxed on it.”
[00:19:32] OG: Well, I mean, to be fair, it does matter what kind of business it is.
[00:19:35] Joe: It does, yes.
[00:19:36] OG: But generally speaking, small b- you said side hustle, so that to me, that implies, you know, a small business. After your expenses in a small business, you know, your run-of-the-mill mom-and-pop shop type of thing, we’re not talking about, you know, General Motors here.
[00:19:51] OG: I mean, although it works similarly. You have your income, you minus out your expenses, that’s your profit. That profit number then is basically passed through to the owners of the company. If you’re the only owner, it just shows up whether you spend the money or you don’t, or you consume the money or you don’t, or transfer it from your account or you don’t, the profit is gonna show up on your personal tax return as, as earnings, and then you have to pay taxes on it.
[00:20:17] Joe: This is where it’s really important when you set up the business to know what type of business I’m setting up, what the positives and negatives are of different ways of setting up the business. That’s for a different episode, ’cause it doesn’t, uh, help all of our stackers. But when you’re setting up the business, you gotta know.
[00:20:33] Joe: Last one, Doug, “You purchase a margarita machine and write business development on the receipt to write it off.”
[00:20:42] Doug: Please let that be true. Please let that be true.
[00:20:45] Joe: OG?
[00:20:45] Doug: But it’s not.
[00:20:47] OG: I mean, do you own a bar? Or golf course?
[00:20:51] Joe: Well …
[00:20:53] OG: Wedding venue? I think those are all fine, yeah.
[00:20:56] Joe: Yeah, to your point, OG, that could be audit bait, Doug.
[00:20:59] Joe: But it depends on what type of business you’re running. All right, now we know whether a problem is coming, so we have done our am I ahead of the game, am I behind the game. How do we fix it while there’s still time? I mean, the first thing we can do, OG, is we can adjust withholding. The second thing we can do is we can adjust our estimated payments.
[00:21:22] Joe: The third thing we could do, increase withholding from our remaining income the rest of the year. OG, you like any of those better than the others?
[00:21:32] OG: I’m a big fan of out of sight, out of mind. So if you’re gonna be owing money, I think it’s better to take a little bit out of every paycheck. to catch up or to be even money than it is to say, “Oh, I’ll just…
[00:21:45] OG: I’ll be good for it in April.” Slippery slope
[00:21:49] Joe: In the second half of today’s discussion, we’re going to get beyond the essential checkup where we projected the year, we compared the expected tax with the tax already paid. We figured out how to start fixing the problem. After Doug’s trivia, we’re gonna move from defense to offense.
[00:22:06] Joe: We’re gonna talk about what we still can do with retirement accounts, HSAs, investments. What can we do to put ourself in a stronger position before December 31st here at our just past midyear checkup? Doug, let’s, uh, do our trivia checkup. What do we got in the tank today?
[00:22:26] Doug: Hey there, Stackers. I’m Joe’s mom’s neighbor, Doug, and looky here. It’s our old pal Martha’s birthday. Yes, that’s right, the queen of homemaking skills, Martha Stewart, is having a big day. So let’s ask you a Martha-related question. What was Martha Stewart’s money-related profession before she became a television icon?
[00:22:48] Doug: I’ll be back right after I go help Joe’s mom with the frosting on her latest creation. She always has too much, so I, I guess I’ll have to find a home for the rest of it.
[00:23:03] Doug: Hey there, stackers. I’m frosting gobbler… That doesn’t sound right, and guy who knows a great carrot cake from the smell, Joe’s mom’s neighbor, Doug. You and I are celebrating the queen of decorating’s birthday today, and before the break, I asked you a question about our good friend, Martha. What was her money-related profession before she ruled the boob tube?
[00:23:25] Doug: The answer, back in 1967, Martha launched her career as a stockbroker, and continued down that path for seven years. It was later, I’m told, that she was promoted to inside trader.
[00:23:38] Joe: Wow.
[00:23:39] Doug: What, too soon? And now, back to two guys trading their insider knowledge on how money works. It’s Joe and OG.
[00:23:49] Joe: OG, you’re, you are a big fan of frosting, aren’t you?
[00:23:52] Doug: No. No.
[00:23:53] Joe: Huge frosting lover.
[00:23:54] Doug: He’s not. Hate, hate frosting. This is how the audience will know that you wrote that trivia and not me- … because neither OG or I like frosting.
[00:24:02] OG: So gross.
[00:24:03] Doug: And I can’t eat carrot cake.
[00:24:05] Joe: I didn’t know you couldn’t eat carrot cake.
[00:24:06] Doug: Well, there’s nuts in carrot
[00:24:07] OG: cake. He’s a weak constitution, that’s why.
[00:24:10] Doug: Oh, nuts, nuts kill me.
[00:24:13] Joe: Well, now we know. Now we know the secret sauce, OG. When we’ve- Yeah … we’ve had enough.
[00:24:18] OG: Between an occasional almond and a whiff of cat dander, we could take Doug down in a heartbeat. Oh, yeah.
[00:24:24] Doug: I am a fragile hot house flower.
[00:24:28] Joe: Well, let’s talk about something else that’s fragile, which is your tax situation.
[00:24:31] Joe: My nose is
[00:24:32] OG: all stuffy. I must go to the hospital.
[00:24:35] Doug: I’m gonna take another day off.
[00:24:38] Joe: We handled the immediate tax payment problem in the first half of today’s episode. Let’s take a look at moves that could improve your larger financial plan. One move OG people make right away is to go, “Okay, I’m gonna hide more money in my 401.
[00:24:52] Joe: I think before you do that, you probably gotta look at how your employer match works, ’cause you could make your tax situation better, but you might end up making your overall situation worse depending on how your employer matches.
[00:25:07] OG: Well, I think where I see this happening more frequently is when, you know, somebody online says Roth 401s are better than traditional pre-tax.
[00:25:16] OG: You know, I’m just gonna do that, unknowingly adding $8,000 to their tax bill, which could be fine in the long run if you believe that you’re at a, you know, lower income tax bracket today, and in the future it’s gonna be higher, and this money’s tax-free. But if you haven’t accounted that, for that from a cash flow standpoint, and God forbid you do this with two people, you know, you’re talking about could easily be $15,000 swing in cash flow, where-
[00:25:41] Joe: Yeah
[00:25:41] OG: you know, now that money is gonna be reduced from your paycheck, ’cause it’s gonna auto… You know, you’re gonna have a higher, higher gross income, or taxable income I should say. You know, you might owe some money on the back end, but if you don’t have that flexibility in your cash flow to absorb 15 frigging grand a year, where’s that gonna go?
[00:26:00] OG: It’s gonna go on credit card, or it’s gonna go in reduced cash reserve. You’re, you’re gonna eat into your emergency fund. And if you’re not accounting for that right out the gate, you have some problems. Now- It
[00:26:09] Joe: could be big tax surprise, yeah.
[00:26:10] OG: Yeah. If you’re 22 and this is your first job, or you just got a huge pay raise, you know, ’cause you changed companies, and you’re like, “What should I do?”
[00:26:16] OG: Like, that’s a perfect time to do that. Like, make that switch, you know, all in because, you know, it’s gonna have a… Uh, it’s not gonna have as big of an impact. But I see people do these things without seeing the second or third domino down the line, and like, what’s gonna happen? And then, um- I don’t care who you are, 15 grand you know, it’s- Yeah
[00:26:36] OG: it’s a notice. Or 1,000 bucks a month or 1,200 bucks a month is somewhat noticeable in, um, I would say the vast majority of people’s cash flow.
[00:26:43] Joe: But if you’ve got good cash flow and you just did the projection during the first half of today’s show, and it looks like you’re gonna get a big refund back, well then this might be a great time to change over to the Roth.
[00:26:55] OG: Could be,
[00:26:56] Joe: yep. Assuming you can, you can absorb it, yeah.
[00:26:58] OG: Yeah.
[00:26:59] Joe: Let’s talk about HSAs, putting money in the HSAs. How could that potentially change the second half of the year tax-wise?
[00:27:06] OG: Well, it’s another pre-tax account, right? We’ve talked about HSAs before. I’m not entirely convinced that it works out exactly perfect What I mean by that is does the increased healthcare cost that you’re out of pocket now offset the fact that you now get to save more money?
[00:27:24] OG: Like, there’s no rule against you saving money anyway. You know what I mean? So if, if you had $8,000 to save, yeah, it’s nice to put it in an HSA ’cause it’s, you know, you get some tax benefits. But I think you have to evaluate that very carefully, I guess is what I’m saying. When it comes down to, you know, your health insurance benefits at work, I think everybody is just so drawn to, “Oh, I’m gonna pick the HSA ’cause that’s supposed to be awesome.”
[00:27:47] OG: And it’s like, well, maybe if you pick the health insurance that is a little different, you know, you would still be out of pocket the same. I don’t know. Like, it’s hard to project that, and a little foreshadowing what Doc G’s gonna talk about in a couple of days, there’s just not a lot of transparency in the healthcare space, unfortunately.
[00:28:07] Joe: Yeah. I remember when Beth Pinsker was on, she was talking about, uh, the fact that HSAs haven’t grown the way that people expected them to grow because 100% what you’re talking about, OG, people are like, “Do I really want that much out of pocket?”
[00:28:21] OG: I mean, dude, we spend… I think our premium for our family on a small business plan, right, I think it’s three grand a month, 3,500 a month.
[00:28:30] OG: And when we just had this thing with my middle kid about his hand, went to this hand specialist, and they’re like, “Okay, let me check your insurance.” I’m like, “Whoa, pump the brakes. I, I’m not fixing to spend 2,500 bucks today, so how about you let me know what the cash price is?” And they’re like, “Well, we collect $200.”
[00:28:48] OG: How, how… Like, what does that get me? I got three X-rays, time with the PA, time with the surgeon, and a new brace for my kid, like a brace for his thumb, and it was $211.
[00:29:01] Doug: Wow.
[00:29:01] OG: I guarantee F and T that if I ran that through insurance, it would’ve been 2,500 bucks co-pay. Oh, yeah. And, and I’m on the hook for the co-pay anyway.
[00:29:11] OG: I don’t… We don’t need to turn this into an insurance debate. I just-
[00:29:14] Joe: No … rage against the machine And again, we will be talking about, we are gonna talk about that machine on Thursday with, with Doc G. So the HSA can help, but don’t go get an HSA just because of the fact that you think you wanna, uh, have some tax help.
[00:29:27] Joe: Like, really think through your overall plan if, uh, HSA’s gonna be a good thing. I mean, I’m
[00:29:31] OG: glad I have one. Yeah. Glad I’ve got money in there that’s growing. I use it. I, I don’t… I’m not one of these guys that, like, holds onto it and waits for, till I’m 107 to start spending, you know?
[00:29:43] Joe: Well, and the downside there, too, I mean, the estate planning issues around HSAs.
[00:29:47] Joe: Uh,
[00:29:47] OG: estate planning. Yeah, record keeping. You know, I just, I don’t know.
[00:29:51] Joe: Yeah. Let’s finish up this discussion with your investments, OG. Here in August, what should I be looking at with my investments tax-wise if I’m auditing?
[00:30:02] OG: Tax-wise on investments? Well, I guess you’d probably just look and see what’s the best performer for the year, and then make sure all your money’s in it.
[00:30:10] Joe: That’s it.
[00:30:10] OG: You know?
[00:30:11] Joe: Tax-wise, though.
[00:30:13] OG: Yeah. The taxes be damned. That’s my answer. It’s like, if you don’t have the number one performer as of August 1, um, statistically, you are gonna lose money next year, so, um-
[00:30:24] Joe: Yeah, your goal is to pay more in taxes. What are you doing staying diversified? Like, let’s get with it.
[00:30:28] OG: Yeah, I, on the tax front, uh, with investments, I think there’s a couple of major levers that you can pull. I think you can be strategic around IRA conversions, if that’s something that’s going on in your world, and you’ve got pre-tax money, and you have an idea of where those brackets are. But I wouldn’t do that until December or, you know, like Thanksgiving time, because you need to have some pretty good certainty on where your ta- where your income’s gonna be.
[00:30:51] OG: Um, the second thing is, um, certainly on capital gains treatment and tax loss harvesting, the jury’s out on whether or not the juice is worth the squeeze there if you’re not very, very, very tactical and don’t have an exact system built in. But I will tell you one thing that I think is, is uniformly true now across the board.
[00:31:10] OG: There is no reason, if you have non-qualified assets, so if you have a regular brokerage account, there is no reason to be donating money to charity via cash instead of a donor-advised fund.
[00:31:21] Joe: Mm. Mm-hmm.
[00:31:22] OG: It’s inexpensive. It takes a little bit of time, but it’s not the end of the world. And if you’re gonna say, “Well, I only do $100 a month in my church envelope,” awesome.
[00:31:32] OG: Take that out of the frigging highest tax thing that you have in your investment account, and put the $100 a month back in your investment account, and buy the, rebuy the thing at a higher basis. You know? So you’re, you’re giving the charity the, the tax problem, which they don’t, they don’t deal with, right?
[00:31:50] OG: They skip taxes, and you don’t pay taxes, and you get to replenish your investment account, or re- re, you know, rebasis your tax account. I don’t know how to say it any differently. Like, you’re, you’re basically right-sizing it, you know- Yeah … from a tax standpoint. It’s $50 a month. Like, where’s the cutoff? I just don’t see why you wouldn’t do this.
[00:32:09] OG: You know, record-keeping wise, it’s one line item. Like, charitable fund donation, 1,500 bucks this year. Done. You don’t have to keep track of all the receipts. You know, people will say to me, “Well, you know, we just like to give a little bit to a lot of different places.” No problem. You just go online and do it.
[00:32:24] OG: You just have to sit down and do it. The only reason you don’t wanna do this is because of your own personal vanity of you wanna, like, hand the check- You know what I mean? Like, you wanna be seen filling out the check and putting it in the envelope and putting it in the church plate
[00:32:40] Joe: Or skipping the envelope and handing it to somebody to show that you’re a good, good person.
[00:32:44] OG: Yeah. Jesus don’t care. He’s good, man. He got enough. He’s okay however you send it to him, you know, or whoever. Don’t have to be Jesus. You can send your money to anybody. But especially as it compounds over time, you know, you think, “Okay, if I’m 30, what’s the value of stripping off my highest tax stuff every year for my charitable contribution?”
[00:33:03] OG: Even if you’re only giving away a little bit of money, you just strip that off. Or you’re trying to build that muscle, you don’t know where you wanna give the money away yet, but you know you wanna be charitable, and so you’re like, “I don’t, I don’t believe in anything strong enough to give them any of my money, but I wanna build that muscle.”
[00:33:18] OG: Boom, you put it in the donor-advised fund. You don’t have to give it out of the donor-advised fund. The donation, the charity that you’re doing, the charitable event is when you take it from your brokerage account and it goes in the donor-advised fund. So, um, I think everybody should have one of those, though, if you have charity on top of mind
[00:33:35] Joe: We will link to, by the way, donor-advised funds is a whole different episode on its own.
[00:33:39] Joe: We spoke with Adam Nash, who is the creator of, uh, Daffy, uh, uh, a donor-advised fund company. We’ll link to that in the show notes if you wanna go deeper on donor-advised funds. What about, uh, evaluating, OG, your, uh, tax location, like asset location? You know, I’ve got something that throws off a lot of dividends in my non-qualified account.
[00:33:58] Joe: I got pretty tax efficient stuff in my IRA. Do we wanna tweak that too?
[00:34:04] OG: I mean, it’s definitely 401 stuff. I’m not… There’s bigger, bigger problems to have than, um-
[00:34:12] Joe: Yeah. Again, juice, squeeze …
[00:34:13] OG: I mean, what are you talking about? You have a million dollars in your brokerage account. A diversified ETF portfolio is gonna kick off 20 grand of dividends, which, by the way, are taxed at a pretty preferential rate relative to income.
[00:34:25] Joe: It’s not zero, but it’s not the first thing you’re looking at.
[00:34:29] OG: I mean, it could be zero. Dividends are tax free up to a certain amount, so.
[00:34:32] Joe: Yeah. I wanna end on this. Who should be doing these things themself, and who really needs that, uh, professional tax person?
[00:34:42] OG: I think that this is a great linkage to my HVAC story from earlier last week, I guess, maybe toward the end of a show.
[00:34:49] OG: You maybe caught it. But Doug said it succinctly, so I’m gonna give Doug all the props in the world. Wait, what? Mad props, Doug. What’s going on here?
[00:34:56] Doug: Whoa.
[00:34:57] OG: You were like, “You got three choices. Your choices are, get a second opinion, become a expert on your own” “And whatever the third one was.” So I really took it to heart.
[00:35:12] OG: You can tell. Find
[00:35:12] Doug: somebody you trust and stick with them.
[00:35:13] OG: There you go. Find somebody you trust. So yeah, I think you’re one of those three people, right? You either have the competence and the time and energy to devote to it, in which case, frigging get after it. If you don’t, and the impacts are big enough, then yeah, I think you need to look for outside help.
[00:35:30] Joe: Big thing today, Stackers, it’s a good time to be a planner, so your mid-year tax checkup, project your full year income, estimate what your total tax is, add up what you’ve already paid, find out whether you’re on track, and then begin tweaking based on all that. We have all these moves and more in our tax guide.
[00:35:49] Joe: If you go to stackingbenjamins.com/guides, you’ll see our tax guide, and that’s a nice place to start to begin getting your handle on, uh, how this whole tax planning thing works. That’s a wrap on our big focus tax planning.
[00:36:08] Joe: It is financial action month here in Mom’s Basement, and if you’re playing Stacker with us, let’s take a look, guys, because the Stacker board looks a lot like the bingo board. We’ve got Scout as the free space in the middle. OG, pick one of these off that our Stackers can do today. Maybe takes them 10, 15 minutes, and we put some money in people’s pockets.
[00:36:27] Joe: Let’s do it.
[00:36:29] OG: I c- I can do any one I want? I can tell you- Yeah … what I just did.
[00:36:31] Joe: Oh,
[00:36:31] OG: good. I just got an email from Apple saying that their Apple One subscription is increasing, the price And so I went online, and I ch- yeah, so number six, check your subscriptions. I went through and I figured out that, uh, it’s not better for us to bundle it as a family ’cause the people don’t use all of the things.
[00:36:50] OG: Like, we use two of ’em, so we’re gonna unsubscribe from, from the ones that we don’t use, and, uh, basically unbundle the service, and, uh, save myself 150 bucks a year.
[00:37:00] Joe: That’s fantastic. Yeah, we canceled Apple for the summer. W- uh, I think we’re gonna get it back in a couple months. There’s now a couple series on there that we wanna watch, but that’s a great one.
[00:37:09] OG: Well, you’re talking about Apple TV. I’m talking about, like, the whole Apple-
[00:37:13] Joe: Uh, ecosystem thing …
[00:37:14] OG: thing. Yeah.
[00:37:15] Joe: Yeah, yeah, yeah. Yeah, check your subscriptions, stackers. That is number six on the list. Pause the podcast, do that right now, and you will put some money in your pocket. But here’s the thing, OG, don’t just cancel the subscription.
[00:37:29] Joe: Take that money now and- Spend it … add it to one of your accounts. Oh.
[00:37:35] Doug: Go to Culver’s.
[00:37:37] Joe: Exact- oh, man.
[00:37:38] OG: And if you don’t know, I will just add to this, if you don’t know where your subscriptions are, you can use the field kit. You can cancel everything right from there.
[00:37:44] Joe: Take the field kit. The field kit’s the old vault.
[00:37:47] Joe: Uh, stackingbenjamins.com/fieldkit, and they’ll, they’ll cancel it for you. And hopefully by this point, OG, as you and I, uh, talked offline, hopefully field kit’s open. If it’s not, it says, “Join the wait list.” So might be a day or two before you are able to do it, but oh, man, I am hoping by the time people hear this, the field kit is open.
[00:38:06] Joe: All right. Thank you so much for spending time with us. If you know somebody who needs that mid-year checkup, maybe they mentioned they got a big bonus this year, maybe they mentioned that they’re still working on their taxes for this year and they need to be a little better organized, uh, whatever it might be-
[00:38:22] OG: Hey
[00:38:23] Joe: great time.
[00:38:23] OG: I’m organized. Yeah. So- I have the piles right here.
[00:38:26] Joe: Somebody feels seen, Doug. Somebody feels like I’m talking directly to them. I
[00:38:29] OG: will tell you, I am, I am happy. Sometimes you find little tax surprises. So in my infinite wisdom last year, I might add, uh, my infinite wisdom, I paid my property taxes twice in 2025.
[00:38:42] Joe: Bam.
[00:38:42] OG: So bango-bango, double tax benefit. Now, of course, this causes a little bit of a tax problem in ’26- Uh-huh … but that is ’26’s problem to deal with. That’s a
[00:38:52] Doug: story
[00:38:53] OG: for another day. We’re gonna swim in the Scrooge McDuck money of 2025 for a while. Yeah, buddy. Good job, OG.
[00:39:00] Joe: Strategery. Which one is that? Uh, there’s, there’s 25 spaces on Stacko.
[00:39:04] Joe: That must have been space 26, pay your property taxes twice. Double
[00:39:07] OG: pay. Right. Pull forward, pull forward expenses, yeah
[00:39:11] Joe: Ah, that’s gonna do it for today. Doug, what should we have learned on today’s show?
[00:39:15] Doug: Well, Joe, first, take some advice from our tax discussion. Taxes are a lot less taxing if you do some tax planning proactively instead of just reaching to your tax mess next year.
[00:39:26] Doug: Tried to squeeze two or three more taxes in there, but it was too… Okay, one more time. I gotta say it. It was too taxing. Second, that Stakko tip, go do it now. You get to use that cool red stamper thing you bought just for Stakko. But the big lesson, don’t tell Joe’s mom she’s Martha Stewart of Texarkana.
[00:39:48] Doug: Apparently, that doesn’t make her happy because she’ll just correct you and say that Martha is the Joe’s mom of Connecticut. Not sure why that’s triggering, but I’d stay away from it anyway. What are you waiting for? Grab your Stakko board and play along at stackingbenjamins.com/stakko. Everybody’s doing it.
[00:40:07] Doug: This show is the property of SB Podcasts, LLC, copyright 2026, and is created by Joe Saul-Sehy. You’ll find out about our awesome team at stackingbenjamins.com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. And oh yeah, before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know.
[00:40:33] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s mom’s neighbor, Doug, and we’ll see you next time back here at The Stacking Benjamins Show
[00:41:35] Joe: Welcome to the after show. This is the part of the show that doesn’t exist. Uh, what’s going on with your air conditionings that we’re gonna talk about?
[00:41:42] OG: This is just a question that I have. No. And I would appreciate any HVAC professional to walk me through this, because I’m not an HVAC pro. Oh, no. You know, that’s not m- that’s not my jam.
[00:41:57] OG: I can change oil in a car if you buy the oil for me, jack the car up, show me the screwdriver I need to get the oil out- Screwdriver … and exactly what oil looks like, then I can get the oil out Why is my oil pink? It’s like, oh my God.
[00:42:12] Doug: Tell yeah. Tell me you don’t know how to change oil without telling me.
[00:42:17] OG: I did actually change a complete…
[00:42:19] OG: Like, now we’re gonna be totally off the rails. I did change a tire in front of my kids once, and they’re like, “What are you doing?” And I’m like, “I’m showing you how to do this.” And I actually did it, like, first go, no, didn’t miss anything. Didn’t, didn’t, like, uh, you know, how you have to, like, take the lug nuts off before you jack the tire up- Yeah
[00:42:34] OG: so you get the little torque, you know? Yeah. And I’m like, I didn’t miss any of that. And anyway, I was pretty proud of myself.
[00:42:39] Doug: Were you brave enough to drive the car away after you changed the tire?
[00:42:43] OG: No. But I did have a time where I was trying to jump one of my kids’ cars with a… And, and it wouldn’t, it wouldn’t take.
[00:42:50] OG: And so I called my brother, and he’s like, “What, what, what do you got it connected to?” And I told him, he goes, “Oh yeah, that’s insulated.” I’m like, “It’s a big metal bolt in the engine.” He goes, “Yeah, but it’s insulated. You gotta try something different.” And as soon as I did, you know, it was a big spark, and the car starts up right away.
[00:43:03] OG: You know, you’re like, oh. Anyways, I digress. Here’s the problem. So our AC goes out. It’s 150 million degrees in Dallas. Thankfully, we have more than one, so, like, a l- part of the house is, like, hotter than the face of the sun, and another part is tolerable. And, um, you know, we call the emergency number. People come out the next morning, and this kid’s like…
[00:43:25] OG: And I say kid ’cause this is 22-year-old service tech person. Explain what’s going on. He goes out and tests a bunch of things and comes back and says, “Here’s what’s wrong. The power line from the unit outside to the unit inside is not connected. You know, it’s broken. It must have frayed. It’s not getting power, so you need a new one of those.”
[00:43:45] OG: And I was like, “Okay. What’s the ticket? You know, what’s the jam? What are we doing?” He goes, “Well, first of all, I can’t get to it till next Thursday, a week from now. Um, secondly, it’s gonna be pretty pricey ’cause we gotta run this conduit up to your roof line and drill a hole in your roof, and then, you know, this is a big project.
[00:44:01] OG: Gonna take us all day. It’s gonna be three grand.” And I’m like, “Holy schnikes. Okay.”
[00:44:04] Doug: Wow.
[00:44:05] OG: And I argued with him a little bit. I’m like, “Well, why can’t you, you know, fish it through the existing wire?” All this other sort of stuff. And he says on the way out, he goes, “Look, we’re not the cheapest guy in town, so you’ll probably find somebody cheaper, you know, but we guarantee our work,” blah, blah, blah, blah, blah.
[00:44:17] OG: “But if I were you, I would shop it because, you know, you might be able to find somebody that can do this sooner than next Thursday.” Okay. Which obviously it’s 1,000 degrees in Texas, so, you know, I’m trying to get it done. So we call another guy that we had done, done some work with before. He comes over later that day.
[00:44:33] OG: Same story. Here’s what’s going on. Here’s what… He says, “What’s the, uh, what did the other guy say?” And I told him, and he just kind of looks like, “Hmm.” That’s not a nor- I could tell he was like, “That’s not a normal problem.” Like, it could be a problem, but it’s not a normal problem. Comes over, gets out his tools, and he goes, “Well, if it doesn’t have power, you know, then this little tool I have here wouldn’t be lighting up like a Christmas tree.
[00:44:54] OG: So you got power. That’s not the issue. The issue’s gotta be this sensor here, and let me try it.” And he, you know, he’s talking through what he’s doing. I don’t know the first damn thing what he’s doing, but he’s, you know, this reset button’s not resetting. He goes, “Is the breaker off?” And I go, “Well, it’s in the garage.
[00:45:07] OG: I don’t know.” And he goes, “No, no, the breaker’s right here. Did it trip yesterday when this went off?” And I was like I don’t… I wouldn’t know. And so he rewires some stuff, you know, goes, “Okay, I think this…” You know, and then he goes to the breaker, flips it on, it runs. And he goes, “There you go. Okay. Yeah, you’re good.”
[00:45:27] OG: You know, of course I’m like flabbergasted that this guy fixed it. It’s amazing. It’s like miracle work. He wants 300 bucks, which is totally fine, totally respectable. But he said, “I don’t want any of your money yet, ’cause I wanna make sure this is actually the fix.” He’s like, “I fixed it, but I wanna make sure that this, th- there’s nothing else that was broken because of the fact that this thing effectively overheated and it tripped this system that is designed to make it so that you don’t cause further damage, but let’s run it for the day and call me later.”
[00:45:54] Joe: Cool.
[00:45:54] OG: I was like, “Well, let me pay you.” You know? He goes, “Nah, you’re good.” Okay. So here’s my question to all the HVAC people Is there some sort of like, like s- like how do I know that I’m not getting totally screwed along the way? Because if I wouldn’t have called that second guy, the first guy was very convinced that this was the problem, and it clearly wasn’t the problem And there’s a pretty big disparity between three grand and 300 bucks.
[00:46:24] OG: And the fact that this other guy like literally was like, “Well, did he try this?” And like holds the electrical thing up to the wire. You know, and goes, “Well, there’s power. Like didn’t he check the…” Like, it was just like, you know, maybe it’s a little how I feel like when I meet with a client and they’re like, “Well, I have a guy that does it.”
[00:46:40] OG: And you’re like, “Wait, how did you do this? Like, why did you do it this way? Like this is completely wrong, you know? This isn’t the law.” Maybe it’s the same sort of experience. I was telling Doug this story earlier. I wrote an email to the company and I said, “I’m gonna choose to believe that you guys aren’t screwing people out of their money on purpose, that this is maybe just a training issue.
[00:46:58] OG: Like maybe just this guy needs a little bit more education or experience, but you might wanna invest in that.” But how do we handle this, you know, as non-educated consumers of this particular or any particular industry? Yeah. Like ’cause, you know, you got the one of the biggest companies in Dallas that comes out and goes, “Hey,” very confidently, like, “I checked everything.
[00:47:19] OG: Boom, boom, boom. Here’s the, here’s the problem. Not great news. We’re gonna fix it for you. Can’t do it till Thursday.” You know, you’re like, “Okay.” You know? What if I didn’t have another guy? Now I’m sitting in this frigging 100 degrees in my house for the next week, gonna spend $3,000 only to find out, by the way, that that wasn’t the fix because they would’ve done all that and then gone, “Oh that ain’t it.”
[00:47:39] Doug: This is just like every other service that you have to use in your life, all the way from, you know, the top most educatedly required service, whether it’s doctors or nuclear fission scientists, all the way down to HVAC guys or- We use those guys all
[00:47:55] OG: the time.
[00:47:56] Doug: All the time … I, I know, right? I mean, you just have to either find somebody you trust or have a second opinion or get yourself educated.
[00:48:05] Doug: I can’t think of a third- Yeah … fourth option.
[00:48:08] OG: I mean, is there a chance that this was just a big scammy, scammy McScammerson? I, I don’t know. I- Well, I would’ve- … I would tend not to believe that’s not the case, just maybe it’s an educations thing.
[00:48:17] Joe: Yeah, I would believe it’s not the case only for one reason. I don’t think he would’ve told you to shop him because he couldn’t- Yeah
[00:48:23] Joe: get to it so quickly- Excellent point … if, if he was scamming you. If he was scamming you, he would’ve tried to get your money today.
[00:48:29] OG: But I will tell you that the invoice that they sent just said, “Service required, 2,900 bucks.”
[00:48:36] Joe: Wow.
[00:48:36] OG: Like it didn’t say like- No,
[00:48:37] Doug: I’m with Joe.
[00:48:38] Joe: Wow.
[00:48:38] OG: Like I, I would wanna see labor, four guys at $200 an hour times three hours.
[00:48:47] OG: You know, like that I can wrap my head around, you know? 67 feet of high density 24 volt cable, 67 feet of conduit. You know, like whatever. You’re like, “Okay, this guy, we, you know, we priced this out and that’s how much it costs.” You know, they’ve got a markup, I get that, but a line item that says- Fix it. Three grand.
[00:49:07] Doug: I’m with Joe. I think this is y- like, technician error. And by that, I mean he just was moving too fast, didn’t assume the simplest issue may be the issue. What’s that, the
[00:49:19] OG: Occam’s razor thing, the most likely thing- Occam’s
[00:49:24] Doug: razor, exactly … is the, is the most likely thing? Yeah. Exactly right. Yeah, and so, and he just kind of, he had a fork in the road and he took the more complicated path.
[00:49:30] Doug: Yeah. But I, I don’t think it was a scam, ’cause I think Joe nailed
[00:49:34] OG: it. I don’t think it’s scammy, it’s just, it’s like I guess, I guess my question isn’t the scam part, it’s more about, like, how do you protect yourself against-
[00:49:40] Joe: The wrong diagnosis …
[00:49:41] OG: their incompetence.
[00:49:42] Doug: Well, you did it, right? You did it, because if I remember the story you were telling me, you got this big number and you’re like, “Hmm,” your Spidey senses went off, and you’re like, “Hold on.”
[00:49:50] Doug: And then you asked your wife-
[00:49:51] OG: Well, mostly I was like, “I’m gonna be on vacation for a week. I can’t have my house be 100 degrees.” Yeah. “And I can’t not go on vacation,” obviously.
[00:49:59] Doug: But something didn’t smell right to you, and you’re like, “I better get a second opinion,” and you asked Lissa, and she had somebody else you guys had used in the past.
[00:50:06] Doug: So you called- Yeah … him, and then he showed up and he was awesome. So I mean, it’s just, you just gotta trust your s- your gut on some of those cases.
[00:50:13] OG: Yeah.
[00:50:14] Doug: Yeah.
[00:50:16] OG: Anyways, uh, AC was fixed yesterday, so got that going for me, which is nice.
[00:50:21] Doug: For 300 instead of three grand.
[00:50:23] Joe: Well, and I just think my rule of thumb is if, if, m- maybe if it has a comma in it, I get a second opinion.
[00:50:28] Joe: Right. If the bill has a comma, just ask more than one person. I don’t know. I’d love to hear. Stackers, uh, let us know. Either chat about it in Mom’s Basement, our Facebook group, or, uh, write to us, joe@stackingbenjamins.com.
[00:50:45] Doug: Imagine how grumpy OG would’ve been this whole episode if he didn’t have his AC fixed, if we were recording this- Oh, no, we, we wouldn’t be recording this
[00:50:53] Doug: and he was, it was 142 in his house.
[00:50:55] Joe: Yeah.
[00:50:56] OG: Well, like I mentioned there, we do have a f- there’s a couple other ones. So it was just done- … in the other wing in the house.
[00:51:03] Joe: The other wing.
[00:51:04] Doug: Oh, God. You, you, he’d
[00:51:05] Joe: go over to the East Wing-
[00:51:06] Doug: Unreal …
[00:51:07] Joe: for the day.
[00:51:09] Doug: Unreal.
[00:51:09] Joe: He’ll have Jeeves shut off that part of the house.
[00:51:12] OG: Shut off the West Wing, the library.
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