Your Mid-Year Tax Checkup: Fix Problems Before They Become April's Problem (SB1878)

Summary

The Stacking Benjamins Show – Episode SB1878

“Your Mid-Year Tax Checkup: Fix Problems Before They Become April's Problem”

Hosts: Joe Saul-Sehy & Josh ‘OG’ Bannerman, CFP
Date: August 3, 2026

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Episode Overview

In the spirit of “fun and functional,” Joe, OG, and Doug dedicate this episode to the concept of a mid-year tax checkup. The goal: help listeners avoid common tax pitfalls well before April rolls around, using smart, proactive strategies to forecast, adjust, and optimize their financial and tax situation for the second half of the year.

They tackle:

• Why (and how) to review your tax standing now—not just at the end of the year
• The importance of accurate withholding and estimated payments
• Practical tax moves during the year, including retirement contributions, investments, and charity
• Identifying who needs professional help vs. what you can do yourself
• One actionable money move (Stacko Challenge) for immediate savings

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Key Discussion Points and Insights

1. Why Do a Mid-Year Tax Checkup? (06:25–08:29)

• Don’t Wait for Surprises: The best time to make tax decisions is before year-end. Filing your tax return is too late to fix problems for the prior year.
• Use Recent Data: Leverage your just-filed return and year-to-date income to forecast your total tax liability.

Quote:

“The best time to make tax decisions isn’t when you’re filing…because by then the year’s closed. So today, we’re going to create your mid-year tax checkup.”
— Joe (06:46)

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2. Building Your Tax Forecast: What to Gather & Evaluate (08:13–12:14)

• Key Documents/Info to Review:

  • Last year’s (2025) completed tax return
  • Current year pay stubs and projected bonuses
  • Charitable donations, property taxes, real estate transactions
  • Capital gains, conversions, side hustles

• Steps in the Forecast:

  • Estimate full-year income
  • Assess likely deductions/credits
  • Project total 2026 tax liability
  • Calculate tax already paid (withheld and estimated payments)

• Avoid Overreliance on Refunds: A big refund in 2025 doesn’t guarantee the same result in 2026; income, deductions, and tax law may have shifted.

Quote:

“If you got a big tax refund last year, well…without going through…[the forecast steps] you’re like, ‘Oh, I’m good, I got a big refund last year.’”
— Joe (11:03)

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3. Avoiding Tax Penalties: Understanding the “Safe Harbor” (12:14–18:22)

• Federal Safe Harbor Rules:

  • Withhold at least 110% of last year’s tax bill or 90% of this year’s estimated liability to avoid penalty
  • Tax payments should reflect income throughout the year, even for lumpy incomes

• Estimated Payment Deadlines Are Confusing: Not truly “quarterly,” so use IRS guidance

• Penalty Avoidance Strategies:

  • Proactive adjusting of withholdings if you get a big bonus or income spike
  • Pay extra estimated taxes after lumpy income events

Quote:

“Penalties suck in everything—sporting events, tax events…The yellow card or red card is a really bad thing to get.”
— OG (12:57)

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4. Tax Myths & Moves: Rapid-Fire Game (18:22–23:03)

A fun quiz for Doug and listeners. Key takeaways include:

• Review withholding after raises, job changes, or major life events—not just annually.
• A prior year’s refund does NOT guarantee you’re fine this year.
• Leaving profits in a side hustle account doesn’t shield it from taxes (unless special business structures apply).
• Writing “business development” on a margarita machine receipt is audit bait unless you run a bar, etc.

Memorable Moment:

“You purchase a margarita machine and write business development on the receipt… Please let that be true.”
— Doug (22:49)

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5. Fixing Problems Before Next April (23:03–23:56)

How to Close the Gap:

• Adjust withholding
• Make estimated payments
• Increase withholding for the rest of the year, if underpaid
• Out-of-sight, out-of-mind approach: up paycheck withholding now, rather than waiting and risking a cash crunch or payment plan later

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6. Mid-Year Offensive Moves: Optimizing Retirement/Charity/Investments (31:28–41:29)

a) 401(k) Changes (31:34–33:59)

• Roth vs. Traditional: Carefully consider the cash flow impact before switching—especially if you’re upping Roth contributions, which can unexpectedly increase your tax bill.

“If you do this with two people, you’re talking about…a $15,000 swing in cash flow…If you’re not accounting for that right out the gate, you have some problems.”
— OG (33:09)

b) Health Savings Accounts (HSA) (33:59–36:51)

• HSAs are great but only if the higher-deductible health plan makes sense for you.
• Evaluate out-of-pocket risks vs. tax advantages honestly.

“I’m not entirely convinced that it works out exactly perfect…You have to evaluate that very carefully…”
— OG (34:06)

c) Tax Strategies for Investments (36:52–41:29)

• IRA Conversions: Best to consider in late year when income is predictable
• Tax Loss Harvesting: Only worthwhile if you’re intentional and systematic
• Charitable Giving: Donor Advised Funds (DAFs) are an efficient way to give appreciated assets, avoid taxes, and simplify recordkeeping—even for smaller amounts

“There is no reason…to be donating money to charity via cash instead of a donor advised fund.”
— OG (38:28)

d) Asset Location Adjustments

• Revisit where you hold tax-inefficient assets, but realize that for most people, the impact is minor compared to other planning steps

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7. DIY vs. Professional Help (41:29–42:30)

• DIY: If you have the competency and time, go for it!
• Professional/CPA: If your situation is complex or the impact could be significant, it’s worth seeking tailored advice

“You either have the competence and the time and energy to devote to it… If you don’t and the impacts are big enough…look for outside help.”
— OG (42:15)

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8. Stacko Financial Action Month: Quick Win Challenge (43:14–44:44)

• Stacko Game: Like bingo for financial actions; focus on practical, fast money moves
• Action Pick: Check your digital subscriptions. OG saved $150 by unbundling Apple services his family didn’t use.

Action Step:

“Check your subscriptions…pause the podcast, do that right now, and you will put some money in your pocket.”
— Joe (44:09)

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Notable Quotes

• On Tax Surprises:
  “While tax surprises on the upside are annoying, the more detrimental tax surprise is the one where you owe money that you didn’t expect.” — OG (11:03)

• On Adjusting Withholding:
  “I’m a big fan of out-of-sight, out-of-mind. I think it’s better to take a little out of every paycheck to catch up…than it is to say, ‘I’ll be good for it in April.’ Slippery slope.” — OG (23:39)

• On Professional Help:
  “Find somebody you trust and stick with them…If you don’t and the impacts are big enough…then yeah, I think you need to look for outside help.” — OG (42:14)

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Key Timestamps

• 06:25 — Introduction to mid-year tax planning & why it matters now
• 08:29 — What to gather for a tax forecast; four main steps
• 12:14 — Understanding withholding, bonuses, and tax penalties/safe harbor
• 18:22–23:03 — Tax moves vs. myths: rapid-fire game segment
• 23:03–23:56 — Immediate fixes: withholding, estimated payments
• 31:28–33:59 — Optimizing 401(k) & Roth vs traditional decision
• 33:59–36:51 — HSA considerations and healthcare costs
• 36:52–41:29 — Investment decisions: conversions, loss harvesting, DAFs
• 41:29–42:30 — Who should DIY tax planning vs. use a pro
• 43:14–44:44 — Stacko actionable financial challenge: cancel unused subscriptions

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Memorable Moments

• Doug’s “audit bait”: Suggestion to write off a margarita machine for “business development” got laughs—and a serious caveat!
• IRS agents and “red cards”: Colorful soccer metaphor to explain tax penalties (13:06–13:28)
• OG’s real-life win: Saved $150/year by micromanaging Apple subscriptions (44:00)

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Actionable Takeaways

1. Run your mid-year tax checkup:

• Project your income, deductions, and taxes for the full year
• Check if your withholding/payments have you on track

2. Adjust sooner, not later:

• Increase withholding now vs. scrambling in April
• Make estimated payments after unusual income events

3. Consider tax-advantaged moves:

• Weigh retirement savings, HSAs, and charitable giving options

4. Play along with Stacko:

• Pick one micro-action for immediate savings (e.g., canceling unnecessary digital subscriptions)

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Further Resources

• Stacko game & tax guide: stackingbenjamins.com/guides
• Donor Advised Funds episode with Adam Nash: Linked in the show notes

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Summary:
This lively, content-packed episode delivers a highly actionable mid-year tax strategy for listeners. Using their signature banter and humor, Joe, OG, and Doug make intimidating tax topics approachable, break down the mechanics of safe withholding and strategic tax moves, emphasize the importance of planning, and offer quick ways to save money right now. Whether you do your own taxes or use a pro, this episode will motivate you to take control now—before next April sneaks up.

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For more depth, discussion, and show notes: stackingbenjamins.com

Transcript

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[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.

[Doug]

I've already had three and I am so amped up. This is.

[Joe]

It's going to be a bad day, Og.

[Doug]

It's. Yeah, these people need to listen fast because my mouth's going to be moving.

[Joe]

The words we don't want to 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 have been working a lot of a lot of overtime to keep us safe, men and women in our armed forces. So raise your mugs, stackers, on behalf of the men and women, make a podcast. To 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?

[Doug]

Thanks everybody.

[Joe]

Uh oh.

[OG]

Sounds like somebody's got a case of the mundus.

[Doug]

Live from Joe's mom's basement, it's the Stacking Benjamin Show. 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 mid year tax checkup. What should you toggle to get the best tax treatment on your money? We'll share. And that's not all. It's financial action month, so we'll take one square from the Stacko 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? At least that's what I thought and now two guys who are probably sitting around bragging that they get to work with this guy. It's Joe and. Oh, jj. Juja G.

[Joe]

That's right. Stackers. Welcome to the place where I sit here and pinch myself because I get to sit next to Doug. It is the Stacky Benjamin show. We're super happy that you're here. It is Monday. We're getting nerdy today. OG because it is mid year, just past mid year. Tax evaluation, tax planning in mom's basement.

[OG]

You could see my desk right now. I've got.

[Joe]

Got all the tech stuff ready to go.

[OG]

Yeah, sucks.

[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. We're going to get into this.

[OG]

You're talking about 25 taxes that are on extension, right? Because that's what I'm dealing with. Is there something I'm supposed to be doing besides that? Because I got till. You know, this is what, 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?

[Joe]

Believe it or not, we're going to talk 2026 on today's show. So stackers, get ready to make some moves. Get your documents out. We're going to talk about exactly what you should get out and how to maybe, maybe tweak a little bit so that you don't have to do some big tweaking next April. 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@Stacky Benjamin.com stacko because the big thing is Stacko. That's the game we play. It's like bingo where you can take different financial actions. We're going to walk through one of those. Doug, as you mentioned earlier, walk through one of those today. So a lot on tap. We're going to get right into it. But first we got a couple sponsors who help us keep on keeping on. We're going to hear from them and then we are going to do some mid year tax planning. Let's get it rolling. In business, there's no room for guesswork. Every shipment matters. Every deadline counts. When you're trying to keep operations running smoothly, the last thing you need is uncertainty. That's why reliability is at the core of USPS ground advantage. Every package moves through a Secure nationwide network tracked from door to door with affordable upfront pricing and and delivery you can depend on. Because knowing your logistics are handled lets you focus on everything else. Visit usps.comground advantage to start shipping with confidence. USPS ground advantage we Mean business. In business, there is no room for guesswork. Every shipment matters. Every deadline counts. And when you're trying to keep operations running smoothly, the last thing you need is uncertainty. That's why reliability is at the core of USPS Ground Advantage. From the moment your package is first scanned in, it moves through a secure nationwide network, aiding in a timely and accurate delivery. You get near real time tracking so you can keep up with your shipments. And with affordable upfront pricing, there are no hidden fees or surprise surcharges to throw off your cost sheets. It all adds up to predictable deliveries you can depend on. Because knowing your logistics are handled lets you focus on everything else. Your customers, your team and the future you're building. Visit USPS.com ground advantage to start shipping with confidence. USPS ground advantage we mean business.

[OG]

Hello darlings.

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[OG]

Our stacking.

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Benjamin's Headlines.

[Joe]

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 here from OG I'm still working on taxes. Why are we bringing them back into the basement? Didn't Doug put the tax records in a grocery bag? Mark, do not open until panic season.

[Doug]

Panic season.

[Joe]

Doug, where do you keep your tax documents?

[Doug]

All right, so in all seriousness, I do have a. There aren't many documents that you keep anymore, like actual paper documents. Not many. You get. So I, you know, I have a. For the few that I might get, I've got an 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.

[Joe]

It's perfect. It's all password protected with the password being. Password.

[Doug]

Oh yeah. 1, 2, 3.

[Joe]

Yeah, it's like the Louvre making Louv

[Doug]

their password and putting the really valuable stuff right near the window so you

[Joe]

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 we're going to create your mid year tax checkup. We aren't preparing anybody's return. We're going to figure out whether tax surprise might be coming and what we can still do about it. So the first half, we're going to 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 disclaimer. 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?

[Doug]

It was okay. I mean, but now we know why I'm here.

[Joe]

All right, what are the questions we asked? 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?

[OG]

Oh, well, this is something that we actually tackle every second half of the year for clients. This is one of the kind of standing review segments in our planning year. What are the things that we look forward? Well, we look for, Obviously your completed 2025 return, 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. The 2025 return is 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. If you get paid a bonus in the second half of the year, maybe that's a little harder to guesstimate what it's going to 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? Have you paid 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, but that just gives us a basis of where all the bodies are buried right now.

[Joe]

Yeah.

[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.

[Joe]

Yeah, I like everything that you said and in my head I'm breaking those up kind of into four things. 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 going to be about the same. Those are the hard parts. As you know, OG these lumpy one offs can change things, but we got to look at what the expected full year income. 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 going to get. Third, how much tax do I think I'm going to pay? And then fourth, how much have I already paid? So if I have, I already paid enough in to make sure that I'm going to be okay. 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.

[OG]

Yeah, well, maybe you got a big refund because you got a one off bonus and they withheld it appropriately. Actually, more likely than not, while tax surprises on the upside are annoying, 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. 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 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, we know how much money you make because we pay you every day.

[Joe]

So this could end badly if you don't.

[OG]

Yeah, if we don't take out 40% of this, you're going to owe a big chunk of it on the back end and never feels great. But you got to account for that every year. And once you've built 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, Thanks. I guess, you know, you can just add that line item into your model and figure out where you're going to be.

[Joe]

Well, and that is. And I love that you went there, because this is really where I want to 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 number one is, how much will I still owe? Am I going to owe? Do I project that I'm seeing that I'm going to 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. You're going to have a penalty because throughout the year, you didn't withhold enough. Can we talk about that a second? How does this penalty work?

[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.

[Joe]

You know, 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.

[OG]

I mean, that would be bad. You'd be like, no, no, no, no, no, no, no.

[Doug]

Throws this yellow handkerchief at your front door.

[OG]

Just hear like, tweet, tweet, tweet, tweet, tweet, tweet, tweet. Like, this big, big flag comes your way.

[Joe]

Like, please don't, please don't, please don't. Red card. Oh, crap.

[OG]

Prior to the tax withholding, personal foul. Not withholding enough on that guy. Yeah, penalties suck, man. And if you can avoid them, the better, better you are. The IRS assumes that you earn a consistent income throughout the year. So if you say that you make 100 grand, if your W2 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 didn't earn 200 grand evenly throughout the year. 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 those quarterly estimated payments, which is also kind of stupid because it's not really quarterly. And I, as a taxpayer, business owner, just cannot understand how someone set this up and then called it quarterly.

[Joe]

So horrible.

[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 if you're self employed, something like that. April 15th for Q1. Okay. Stands to reason that's in the ballpark. Also April 15th for any mistakes from the prior year. Okay. You know, kind of self inflicted, I guess, maybe, but it's a big day. June 15th because that.

[Doug]

Right. Because we feel like it.

[Joe]

Because somebody doesn't know math.

[OG]

And September 15th because that also. Yeah. But then your taxes are due October 15th, if you filed an extension or September 15th, you know, anyways, it's.

[Doug]

So my takeaway from this is it's just always tax day. There's just always a tax deadline.

[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. 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. 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 under withhold as long as you're at 110% of last year's, you're not going to have a. You're going to still hold the taxes, but you're not going to have a penalty due.

[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 going to get the penalty.

[OG]

You're not going to get a penalty Just to be clear, 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 going to totally hit the 110 if I did that, but I'm not going to make as much money. You still have to have 90% of your liability. 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 payments. And the first one due April and then June, September, and then October. 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, could only pay it in September or January. You can jump online and be like, hey, my bonus paid in August. And I've, you know, I need to get this money, this extra money that I know I'm going to owe sent to the irs. Get it out of my hands. Basically, you just go online and IRS.gov and make estimated payment.

[Joe]

Yeah, I know people that like that. The second that they get it, just get rid of it. So there's no.

[OG]

Just ship it to the irs. You're going to owe the money anyway. You know, and I get the whole argument that people have about, like, well, I can put this money in my account and earn the 3%. You can. You're right.

[Joe]

There's a lot of know yourself in this.

[OG]

Or you will spend it and. And then April will come around and you'll be like, ah, crap. Now I have a payment plan. I'm under withheld. I owe interest, I owe penalties. It can get pricey in a hurry.

[Joe]

Doug, let's turn this into a game.

[Doug]

I. I'm terrified of this every episode.

[Joe]

Joe, you're going to have the ruling. But, Doug, I'm going to 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. Ready?

[Doug]

Yeah. Okay.

[Joe]

I received a raise or I changed jobs, so I should review my withholding tax move or tax myth.

[Doug]

Useful move.

[Joe]

Yeah. What other changes? Oh, gee, should make us think, you know what? I should probably look at my withholding. Besides a raise or change in jobs.

[OG]

Well, I think where people 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. The math will say, oh, the first $10,000 tax at this rate, and so on and so forth.

[Joe]

They don't think about the fact you've got two jobs.

[OG]

Yeah. So the W4 does ask you that opportunity. It does give you that opportunity to fill in that information so that the correct column basically is used in your withholding. 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, if you get divorced, family life events are going to 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. Those are probably the biggest ones.

[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 what was withheld there. But yeah. Question two, Doug. I received a big refund last year. Some withholding must be correct this year.

[Doug]

No, I'm going to say myth.

[Joe]

That is a myth. Last year's refund tells us weapon. Last year doesn't matter toward this year, a lot of things could have changed. Question 3. I can make one giant estimated payment in December and automatically erase any earlier underpayment penalty.

[Doug]

No, the years are. That's a myth, right? The years are totally separate. Oh, gee, if I heard your question correctly.

[OG]

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. Surprise, surprise, surprise.

[Joe]

Yeah. Round four. Question four. Increasing your withholding late in the year may work differently from making a late estimated payment.

[Doug]

Duh. Holding late in the year works differently. I'm going to say useful, but I don't know.

[Joe]

That's a tax move. That's some good tax planning going on there, Og. I think.

[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.

[Joe]

That's why we're doing this show right now. Question 5. 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?

[Doug]

No, that's. That's not how that works.

[Joe]

You've seen that before, though. Oh, gee, tell me there's no way you haven't seen somebody think that. Well, I'm just gonna leave it in the business so I'm not personally taxed on it.

[OG]

Well, I mean, to be fair, it does matter what kind of business it is.

[Joe]

It does, yes.

[OG]

But generally speaking, small. But 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. 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 going to show up on your personal tax return as earnings, and then you have to pay taxes on it.

[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 because it doesn't help all of our stackers. But when you're setting up the business, you got to know. Last one, Doug. You purchase a margarita machine and write business development on the receipt to write it off.

[Doug]

Please let that be true.

[OG]

Please let that be true.

[Doug]

Oh, gee, but it's not.

[OG]

I mean, do you own a bar or golf course? Well, wedding venue, I think those are fine. Yeah.

[Joe]

Yeah. To your point, OG that could be audit bait, Doug, 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. The third thing we could do, increase withholding from our remaining income the rest of the year. Oh, gee, you like any of those better than the others?

[OG]

I'm a big fan of out of sight, out of mind. So if you're going to 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, I'll be good for it in April. Slippery slope.

[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 going to move from defense to offense. We're going to talk about what we still can do with retirement accounts, HSAs, investments. What can we do to put ourselves in a stronger position before December 31st here at our just past mid year checkup. Doug, let's do our trivia checkup. What do we got in the tank today?

[Doug]

Hey there, stackers. I'm Joe's mom, Bob's neighbor Doug. And look 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? 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.

[Joe]

If you're like me, you've been juggling a lot this summer. Between travel and communicating with the kids, you've, if you've got kids at home, it's even more juggling for you. Hot night. So we're headed over to the neighbor's pool. There's a lot going on and now that travel's hopefully starting to slow, we're getting back into the routine. We're. Well, it's time to take control. You know what, Even when it's out of control factor makes it easy for you. Even when you're on the go factor makes chef crafted dietitian designed ready to eat meals so you don't have to choose between real food and convenience. There's over 175 ban ingredients. Every factor meal is designed around what supports a healthier lifestyle and nothing that doesn't. Factor meals are ready in two minutes. They require no prep, no cleanup. So even on the days your schedule is completely chaotic, eating well, it's still achievable. Listen to some of these meals that I've had recently. You ready for this? This is some crazy stuff. Queso poblano chicken. Oh my goodness. Spicy pork bolognese and cavatappi. Don't know what cavatappi is but it's kava yum yum. I'll tell you that I love the fact that I can eat healthy and I can do it quickly. I I use factor. I think you should too. So let's eat real stackers head to factor meals.com sb50off and use code sb50off and you'll get 50% off and one free breakfast per box for one year while supplies last until 1031 2026. That's code sb50off at factor meals.com sb numeral 50off at factor meals.com c website for more details. It's incredible at a small company like Stacking Benjamin's how one one hire makes all the difference in the world. If you're a small business, the right hire can be make or break Hoping the right people see your job posting isn't the best growth strategy. When the pressure's on, you need the right hire. This is a job for Sponsored Jobs Indeed. Sponsored Jobs is a boost whenever you need to find quality talent. When workplace chaos hits and you need the right hire, this is a job for Sponsored Jobs. Hiring Indeed is all you need. Stop struggling to get your job post even seen at other sites. Get matched with and higher quality candidates who can drive the results you need. Reach candidates that meet your specific criteria like skills, certifications or locations. Sponsor Jobs Boost your job post on search results so you can reach the people that can help your business thrive. Plus, with Indeed Sponsored Jobs you only pay for results. People are finding quality hires on Indeed right now in the minute I've been talking to you. Listen to this. Companies like yours have made 27 hires on Indeed according to Indeed Data worldwide. And Sponsored Jobs posted directly on indeed are 95% more likely to report a hire than non sponsored jobs. So spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results when you need the right person to cut through the chaos. That's a job for Indeed Sponsored Jobs. And guess what? Our stackers are going to get a $75 sponsored job credit. That's you to help get your job the premium status it deserves@ Indeed.com podcast. Just go to Indeed.com podcast right now and support Stacking Benjamins by saying you heard about Indeed in mom's basement. Indeed.com podcast terms and conditions apply. Need a hiring hero? This is a job for Indeed Sponsored Jobs. It's August and here in Texas we start dreaming about cooler weather. Time to start turning over the closet. And that's why I love shopping at Quince. Quince is all about having fewer, better pieces. And their clothes are made with premium materials, built to last and designed to become the ones you reach for day after day. If you're still hanging on to the same worn out basics, Quint makes it easy to upgrade. They have premium denim and tailored chinos from just $60 and the kind of perfect fit structure and high quality fabrics you'd expect from a luxury designer brand. But everything at quints is priced 50 to 80% less than similar brands. They work directly with ethical factories and cut out the middlemen. So you're paying for high quality, not brand markup. And I'm headed north and I'm excited about taking my cashmere sweater with me. And on those cool nights out in the desert at fincon, it's going to be great as well. So upgrade your everyday. Go to quint.comsp for free shipping on your order and 365 day returns. Now available in Canada and the UK too. That's Q-U-I-N c e.comsb for free shipping and 365 day returns. Quints.comsp.

[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 related profession before she ruled the boob tube? 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.

[Joe]

Wow. What?

[Doug]

Too soon? And now back to two guys trading their insider knowledge on how money works. It's Joe and og.

[Joe]

Og, you're. You are a big fan of frosting, aren't you?

[Doug]

No, no.

[Joe]

Huge frosting lover.

[Doug]

He's not. This is how the audience will know that you wrote that trivia and not me. Because neither OG or I like frosting.

[OG]

So gross.

[Doug]

And I can't eat carrot cake.

[Joe]

I didn't know you couldn't eat carrot cake.

[Doug]

No, there's nuts in carrot cake.

[OG]

Weak constitution, that's why.

[Doug]

Oh nuts. Nuts kill me.

[Joe]

Well, now we know. Now we know the secret sauce. Og, when we've. We've had enough.

[OG]

Between an occasional almond and a whiff of cat dander, we could take Doug down in a heartbeat.

[Doug]

I Am a fragile hot house flower.

[Joe]

Well, let's talk about something else that's fragile, which is your tax situation.

[Doug]

I gotta take another day off.

[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 going to hype more money in my 401k. I think before you do that, you probably got to look at how your employer match works because you could make your tax situation better, but you might end up making your overall situation worse depending on how your employer matches.

[OG]

Well, I think where I see this happening more frequently is when, you know, somebody Online says Roth 401ks are better than traditional pre tax. You go, I'm just going to 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 going to 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 yeah, you know, now that money is going to be reduced from your paycheck because it's going to auto, you know, you're going to 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 friggin grand a year, where's that going to go? It's going to go on credit card or it's going to go and reduce cash reserve, you're going to eat into your emergency fund. And if you're not accounting for that right out the gate, you have some problems.

[Joe]

Now it could be big tech surprise.

[OG]

Yeah, yeah, you're 22 and this is your first job or you just got a huge pay raise, you know, because you change companies, you're like, what should I do? Like that's a perfect time to do that, like make that switch, you know, all in. Because you know it's going to have a, it's not going to 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 going to happen? And then I don't care who you are, 15 grand. You know, it's. It's a notice of a thousand bucks a month or twelve hundred bucks a month is somewhat noticeable in, I would say, the vast majority of people's cash flow.

[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 going to get a big refund back, well, then this might be a great time to change over to the roth.

[OG]

Could be.

[Joe]

Assuming you can, you can absorb it.

[OG]

Yeah, yeah.

[Joe]

Let's talk about HSAs. Putting money in the HSAs, how could that potentially change the second half of the year, tax wise?

[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? Like, there's no rule against you saving money anyway, you know what I mean? So if you had $8,000 to save, yeah, it's nice to put it in HSA because 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 going to pick the hsa, because that's supposed to be awesome. 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 little foreshadowing what Doc G is going to talk about in a couple of days. There's not a lot of transparency in the healthcare space, unfortunately.

[Joe]

Yeah. Remember when Beth Pinsker was on, she was talking about the fact that HSAs haven't grown the way that people expected them to grow because 100. What you're talking about OG people like, do I really want that much out of pocket?

[OG]

I mean, dude, we spend, I think, our premium for our family. I have a small business plan, right. I think it's three grand a month, 3,500amonth. 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'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. How?

[Doug]

How?

[OG]

Like what does that get me? I got 3x 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.

[Doug]

Wow.

[OG]

I guarantee effing t that if I ran that through insurance it would have been 2, 500 bucks.

[Doug]

Oh yeah.

[OG]

And, and I'm on the hook for the copay anyway. We don't need to turn this into an insurance.

[Progressive Commercial Auto Insurance Announcer]

No.

[Joe]

And again, we will be talking about, we are going to 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 want to have some tax help. Like really think through your overall plan. If hsa.

[OG]

I mean, glad I have one. 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 on to it and waits for till I'm 107 to start spending.

[Joe]

Well, and the downside there too, I mean the estate planning issues around hsa.

[OG]

Estate planning? Yeah. Record keeping, you know, I just, I don't know.

[Doug]

Yeah.

[Joe]

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

[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.

[Joe]

That's it. You know, tax wise though.

[OG]

Yeah. Taxes be damned. That's my answer. It's like if you don't have the number one performer as of August 1st, statistically, you are going to lose money next year.

[Joe]

So yeah. Your goal is to pay more in taxes. What are you doing staying diversified, like let's get with it.

[OG]

Yeah, I. On the tax front 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, late Thanksgiving time because you need to have some pretty good certainty on where your, where your income's going to be. The second thing is 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. There is no reason, if you have non qualified assets, 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. It's inexpensive, it takes a little bit of time, but it's not the end of the world. And if you're going to say, well, I only do $100 a month in my church envelope, awesome, 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? They skip taxes and you don't pay taxes and you get to replenish your investment account or re, you know, rebases your tax account. I don't know how to say it any differently. Like you're, you're basically right, sizing it, you know, 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. You know, record keeping wise is one line item, like charitable fund donation, 1500 bucks this year, done. You don't have to keep track of all the receipts. You know, people 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. You just have to sit down and do it. The only reason you don't want to do this is because of your own personal vanity of you want to like hand the check, you know what I mean? Like, you want to be seen filling out the check and putting it in the envelope and putting it in the

[Joe]

church plate or skipping the envelope and handing it to somebody to show that you're a good, good person.

[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, doesn'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? 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 want to give the money away yet, but you know, you want to be charitable. And so you're like, I don't believe in anything strong enough to give them any of my money, but I want to build that muscle. Boom. You put it in the donor advice fund. You don't have to give it out of the donor advice fund. The donation, the charity that you're doing, the charitable event is when you take it from your brokerage account, goes in the donor advice fund. So I think everybody should have one of those though if you have charity

[Joe]

on top of mind, we will link to. By the way, Donor Advised funds is a whole different episode on its own. We spoke with Adam Nash, who is the creator of Daffy, a donor advised fund company. We'll link to that in the show notes. If you want to go deeper on Donor Advised Funds, what about evaluating og your tax location? Like asset location? You know, I've got something that throws off a lot of dividends in my non qualified account. I got pretty tax efficient stuff in my ira. Do we want to tweak that too?

[OG]

I mean, it's definitely 401 stuff. I'm not. There's bigger, bigger problems to have than.

[Joe]

Yeah, again, juice squeeze.

[OG]

I mean, what are you talking about? You have a million dollars in your brokerage account. A diversified ETF portfolio is going to kick off 20 grand of dividends, which, by the way, are taxed at a pretty preferential rate relative to income.

[Joe]

It's not zero, but it's not the first thing you're looking at.

[OG]

I mean, it could be zero. Dividends are tax free up to a certain amount.

[Joe]

So I want to end on this. Who should be doing these things themselves and who really needs that professional tax person?

[OG]

I think that this is a great linkage to my H. VAC story from earlier last week. I guess maybe toward the end of a show, you maybe caught it, but Doug said it succinctly. So I'm gonna give Doug all the props in the world.

[Joe]

What's going on?

[Doug]

Whoa.

[OG]

You were like, you got three choices. Your choices are get a second opinion, become an expert on your own, and whatever the third one was. So I really took it to heart.

[Doug]

Find somebody you trust and stick with them.

[OG]

There you go. Find somebody you trust.

[Doug]

Me.

[OG]

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.

[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. If you go to stackybenjamins.com guides you'll see our tax guide. And that's a nice place to start to begin getting your handle on how this whole tax planning thing works. That's a wrap on our big focus tax planning. It is financial action month here. Mom's basement. And if you're playing Stacko with us.

[Doug]

Us.

[Joe]

Let's take a look, guys. Because the Stacko 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. Let's do it.

[OG]

I can do anyone I want. I can tell you what I just did. I just got an email from Apple saying that their Apple one subscription is increasing the price. And so I went online and I checked. So number six, check your subscriptions. I went through and I figured out that it's not better for us to bundle it as a family because the people don't use all of the things like we use two of them. So we're going to unsubscribe from the ones that we don't use and basically unmundle the service and save myself 150 bucks a year.

[Joe]

That's fantastic. Yeah. We canceled Apple for the summer. I think we're going to get it back in a couple months. There's now a couple series on there that we want to watch, but that's a great one.

[OG]

Well, you're talking about Apple tv. I'm talking about like the whole Apple ecosystem thing. Thing.

[Joe]

Yeah, yeah. Check your subscription 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. Take that money now and add it to one of your accounts.

[Doug]

Go to Culver's.

[Joe]

Exactly. Oh, man.

[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 a field kit. You can cancel everything right from there.

[Joe]

Take the field kit, the field kits, the old vault stacky benjamin.com fieldkit and they, they'll cancel it for you. And hopefully by this point, OG as you and I talked offline, hopefully field kits 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. 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. They need to be a little better organized, whatever it might be. Hey, great time.

[OG]

I'm organized. I have some piles right here.

[Joe]

Somebody feels seen Doug. Somebody feels like I'm talking directly.

[OG]

I will tell you I am, I am happy. Sometimes you find little tax surprises. So in my infinite wisdom last year, I might add my infinite wisdom, I paid my property taxes twice in 2025.

[Joe]

Bam.

[OG]

Bango, Bango double tax benefit. Now, of course this causes a little bit of a tax problem in 26, but that is 26 a problem to deal with.

[Doug]

That's a story for swim in the

[OG]

Scrooge McDuck money of 2025 for a while. Yeah, buddy. Good job, OG Strategery.

[Joe]

Which one is that?

[Progressive Commercial Auto Insurance Announcer]

There's.

[Joe]

There's 25 spaces on Stacko. That must have been space. 26. Pay your property taxes twice.

[OG]

Double pay, pull forward, pull forward expenses.

[Joe]

Yeah, that's gonna do it for today. Doug, what should we have learned on today's show?

[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 reaching to your tax mess next year. Tried to squeeze two or three more taxes in there, but it was two. Okay, one more time. I gotta say it. It was too taxing. Second, that Stacko tip. Go do it. Now you get to use that cool red Stamper thing you bought just for Stacko. But the big lesson, don't tell Joe's mom. She's Martha Stewart of Texarkana. 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 Stacko board and play [e-mail] stacko everybody's doing it. This show is the property of SP Podcast, LLC, Copyright 2026 and is created by Joe Salsihai. You'll find out about our awesome team [e-mail] along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello and oh yeah. Before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor Doug and we'll see. See you next time back here at the Stacking Benjamin Show.

[Joe]

It's August and here in Texas we start dreaming about cooler weather. Time to start turning over the closet. And that's why I love shopping at Quint. Quint is all about having fewer, better pieces and their clothes are made with premium materials, built to last and designed to become the ones you reach for day after day. If you're still hanging on to the same worn out basics, Quint makes it easy to upgrade. They have premium denim and Taylor chinos from just $60 and the kind of perfect fit structure and high quality fabrics you'd expect from a luxury designer brand. But everything at Quint is priced 50 to 80% less than similar brands. They work directly with ethical factories and cut out the middlemen. So you're paying for high quality, not brand markup. But I'm headed north and I'm excited about taking my cashmere sweater with me and on those cool nights out in the desert at fincon, it's going to be great as well. So upgrade your everyday. Go to quince.com sp for free shipping on your order and 365 day returns now available in Canada and the UK too. That's Q U I N C E.comSB for free shipping and 365 day returns. Quince.comSB. Welcome to the after show. This is the part of the show that doesn't exist. What's going on with your air conditionings that we're going to talk about?

[OG]

This is just a question that I have and I would appreciate any H Vac professional to walk me through this because I'm not an H Vac pro. You know that's not my jam. 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 and exactly what Oil looks like. Then I can get the oil out. Why is my oil pink? It's like, oh my God.

[Doug]

Yeah. Tell me you don't know how to change oil. You're not telling me.

[OG]

I did actually change a complete. Like now we're going to 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 like, you know, you had to like take the lug nuts off before you jack the tire up so you get the little torque, you know, I'm like, I didn't miss any of that. And I was pretty proud of myself.

[Doug]

Were you brave enough to drive the car away after you changed the tire?

[OG]

No, but I did have a time where I was trying to jump one of my kids cars with a. And it wouldn't take. And so I called my brother and he's like, what do you got it connected to? And I told him, he goes, oh, yeah, that's insulated. Like it's a big metal bolt in the engine. He goes, yeah, but it's insulated. You got to try something different. And as soon as I did, you know, it was a big spark and the car starts up right away. 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 part of the house is like hotter than the face of the sun and another part is tolerable. And you know, we call the emergency number, people come out the next morning and this kid's like. And I say kid, because this 22 year old service tech person explain what's going on. He goes out, 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. 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. Secondly, it's going to be pretty pricey because we got to run this conduit up to your roof line and drill a hole in your roof. And then, you know, this is a big Project can take us all day. It's going to be three grand. And I'm like, holy schnikes. Okay, well. And I argued with him a little bit. I'm like, why can't you 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. 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, which, obviously, it's a thousand degrees in Texas, so, you know, trying to get done. So we call another guy that we had done. Done some work with before. He comes over later that day, same story. Here's what's going on. Here's what he says. What's the. What did the other guy say? And I told him, and he just kind of looks like, hmm, that's not a normal. 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. So you got power. That's not the issue. The issue has got to 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. I don't know. And he goes, no, no, the breakers 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 breaker, flips it on it runs. He goes, there you go, okay, yeah, you're good. 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 because I want to make sure this is actually the fix. He's like, I fixed it, but I want to make sure that this. 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.

[Joe]

Cool.

[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 H VAC people. Is there some sort of like. Like, how do I know that I'm not getting totally screwed along the way? Because if I would 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 3 grand and 300 bucks. 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, goes, well, there's power. Like, didn't he check? 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. 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. I said, I'm going to choose to believe that you guys aren't screwing people out of their money on purpose. That this is maybe just a training issue. Like, maybe just this guy needs a little bit more education or experience, but you might want to invest in that. But how do we handle this, you know, as non educated consumers of this particular or any particular industry? Like, because, you know, you got one of the biggest companies in Dallas that comes out and goes, hey, very confidently, like, I checked everything. Boom, boom, boom. Here's the, here's the problem. Not great news. We're going to fix it for you. Can't do till Thursday. You know, you're like, okay, you know what if I didn't have another guy, I'm sitting this frigging 100 degrees in my house for the next week, going to spend $3,000 only to find out, by the way, that that wasn't the fix. Because they would have done all that and then gone, oh, that ain't it.

[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 H Vac.

[OG]

Use those guys all the time.

[Joe]

All the time.

[Doug]

I know, right? I mean, you just have to either find somebody you trust or have a second opinion or get yourself educated. I can't think of a third fourth option.

[OG]

I mean, is there a chance that this was just a big scammy. Scammy McScammerson? I. I don't know. I would tend not to believe that's not the case. Just maybe it's an educations thing.

[Joe]

Yeah, I would believe it's not the case, only for one reason. I don't think he would have told you to shop him because he couldn't get to it so quickly. If. If he was scamming you. If he was scamming you, he would have tried to get your money today.

[OG]

But I will tell you that the invoice that they sent just said service required 2,900 bucks.

[Doug]

Yeah.

[Progressive Commercial Auto Insurance Announcer]

Wow.

[OG]

Like, it didn't say. Well, like I would want to see labor. Four guys at $200 an hour times three hours, you know, like, that I can wrap my head around, you know, 67ft of high density 24 volt cable, 67ft of conduit, you know, like whatever. You're like, okay, this guy, you know, we price this out and that's how much it costs. You know, they got a markup. I get that. But a line item that says fix it. Three cranes.

[Doug]

I'm with Joe. I think this is like technician error. By that I mean he just was moving too fast. Didn't assume the simplest issue may be the issue.

[OG]

The AAM's razor thing, the. Is the most likely thing.

[Doug]

Exactly. Right? Yeah. And so. And he just kind of. He had a fork in the road and he took the more complicated path. But I, I don't think it was a scam because I think Joe nailed it.

[OG]

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 the wrong diagnosis? Incompetence.

[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, your spidey senses went off. You're like, hold on. And then you asked.

[OG]

Well, most. I was like, I'm going to be on vacation for a week. I can't at my house be 100 degrees and I can't not go on vacation.

[Doug]

Obviously, 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, so you called him, and then he showed up and he was awesome. So, I mean, it's just. You just got to trust your. Your gut on some of those cases.

[OG]

Yeah. Yeah. Anyways, AC was fixed yesterday, so got that going for me, which is nice.

[Doug]

300 instead of three grand.

[Joe]

Well, and I just think my rule of thumb is if maybe if it has a comma in it, I get a second opinion. If the bill has a comma, just ask more than one person. I don't know. I'd love to hear Stackers. Let us know. Either chat about it in Mom's Basement, our Facebook group, or write to us.

[Doug]

Joe stackybenchments.com Imagine how grumpy OG would have been this whole episode if he didn't have his AC fixed. If we were recording this and he was. It was 142 in his house.

[OG]

Yeah, well, like I mentioned there, we do have a few. A couple other ones. So it was just done. Other wing in the house.

[Joe]

You go over to the east wing.

[Doug]

Unreal day.

[Joe]

He'll have Jeeves. Shut off that part of the house.

[OG]

Shut off the west wing. The library. Yeah.

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[OG]

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