Tax Tuesday Episode 138: Startup S-Corp

Jeff: Yeah. Jeff Webb, CPA and Director of the Tax Department. I’m here all the time. You’re probably seeing Toni on Tax Tuesday. 

Toni: I’ve been on a few Tax Tuesdays. 

Jeff: Oh, not Tax Tuesday but Toni Talks.

Toni: Toni Talks, and if you’re a Platinum Client, you’ve most certainly seen me on Platinum Office Hour answering all of your questions. Anyway, just go ahead and get started. It looks like we have some people going ahead and posting in the chat. If you can hear us, type in yes. 

“Yes, yes, yes.” Okay, very good.

Jeff: If you can’t hear us, type in no. 

Toni: Nice one, Jeff. To get started, we’ll go over some of the Tax Tuesday rules. You can ask live questions via the Q&A feature in Zoom. It looks like some folks have already started doing that. You can send in your questions at taxtuesday@andersonadvisors.com. We go through those questions and we bring them to you every other Tuesday. We’ll answer from here as well as answering your live questions. If you need a detailed response, you will need to become a Platinum or a Tax Client. 

Jeff, someone’s asking, “What is Platinum Office Hour?” If you’re a Platinum Client, we have a daily Zoom meeting for all of our clients who like to attend from 4:00–5:00 Pacific. They come in and ask any of their tax or asset protection questions with us. We’re always manned with one of our attorneys and one of our tax advisors for you.

This is a fast, fun, and educational format. We want to give back and help educate. We consider ourselves an education company first.

Jeff: If you’re going to ask questions, make sure you do it in the question side, not the chat side. We will attempt to answer all of the questions, but if you ask a question in the chat, it’s likely not to get an answer.

Toni: Right, so we’ll go over some of the questions that we’re going to be answering for you today.

“I have three different businesses and plan to add more. How should I pay myself from each one for maximum tax benefits? I’m on a payroll and receiving a K-1 for each company, but my tax debt is stacking up. I also try to purchase more property or refinance some of my other ones but at times, my debt-to-income ratio interferes with the process.” I thought that was shorter. I think Toby is messing with us. We’ll answer that.

“Do wholesalers of land need to pay self-employment tax?” That is a short one but that’s a good one. We’ll answer it.

“To maximize tax benefits as a realtor, is there a catch to it being your full-time business? I have a salaried job that I rarely work more than 20–30 hours a week and do a realtor business as well. Is there a catch that limits some tax breaks for real estate or if real estate isn’t considered my main job?” That’s a very good question. We’ll answer that. 

“Could you please review how LLCs can work with 501(c)(3)s for both to maximize benefit? The LLC being a for-profit and the 501(c)(3) being non-profit. How can they interface without violating any tax code?” Be a disqualified person, prohibited transactions, and self-dealings just pop into my head. We’ll go over that.

“If I run my real estate business from my home, can I deduct a portion of all home expenses, i.e., property tax, utilities, insurance, et cetera?” Toby would love that one. We’ll go over that.

“Startup S-corp has no revenue yet. If I file taxes jointly with my husband, any concerns?” Smooth. We’ll go over that.

Jeff: I like the extra commas you put in there.

Toni: “What is the best way to pay your children (teenagers)”—good, so they can hold something—“when they work in your business? Payroll, cash at time of service, then year ending 1099?” We’ll answer that.

“I reimburse myself for my health insurance premiums through my C-corp. My fiancé and I are planning to get married later this year and I will become eligible to get my health insurance through her employer. Is it permissible to reimburse her for my portion of the premium through that same C-corp? This is an entity that was setup by Anderson Advisors.” Good call. We’ll answer that.

Jeff: Good question. 

Toni: “Can you explain how to invest in stocks from an LLC and how it is beneficial on taxes? What are our write-offs if we are investing in stocks?” Trick question, right? We’ll answer that. 

“Can I use an S-corp to serve as a management company for my real estate investment if the real estate is held by my Wyoming Holding and Illinois single-member managed LLC? Are there any tax benefits to this strategy?” We can make some. We’ll answer that. 

“If I have an S-corp, can I use a combination of Section 179 and 168(k) for equipment or business vehicles?” Jeff will answer that. 

Jeff: I will do so.

Toni: “Is it better to file married jointly or separate?” We’ll answer that.

“Is it better for a single member LLC to file taxes as a disregarded entity or as a partnership? And why?” We’ll answer that as well. 

These are some fantastic questions. All right, we’re hopping right in, folks. 

Jeff: Yeah.

Toni: Seems like. 

Jeff: We’re going to answer the one Toby threw in there.

Toni: I think Toby did some adding on here. 

“I have three different businesses and plan to add more. How should I pay myself from each one for maximum tax benefits? I’m on payroll and receiving a K-1 for each company, but my tax debt is stacking up. I also try to purchase more property or refinance some of my other ones but at times, my debt-to-income ratio interferes with the process.” 

I think we’re going to have to approach this in some bite-sized pieces because the part of this that sticks out to me, obviously we don’t have any specifics. We don’t know what kind of businesses these are, what kind of entities they’re in, but the clue, the breadcrumb I could see there is, “I’m on payroll and receiving a K-1 for each company.” 

In order to be on payroll and receive a K-1, you’re going to have to be an S-corporation. If you’re a partnership receiving a K-1, you are not an employee so you would not receive a payroll, a W-2.

Jeff: I’m assuming that they’re investing in rental properties, especially since they talked about they’re trying to buy more properties and they have problems getting additional financing to buy more. We see that sometimes, especially if you’re very leveraged. It becomes more difficult to get additional loans even though you’re still securing the loans with those properties. And the bank’s main concern is can you make the payments on these loans based on your income stream?

Toni: Right. Debt-to-income ratio, you’ve got a balancing act issue is what’s happening here because in order to get that debt-to-income ratio to be what a lender would want it to be, you’re going to have to pay yourself a payroll. But you pay yourself a payroll and the payroll is going to increase that tax that you’re talking about that’s stacking up. You actually have to look at it and go, which one is going to be worth it to me? Because we can’t, on the one hand, omit deductions so that we have a higher net income to show the finance company, and also go on the heels of that and add deductions so that we don’t have that tax burden. 

One thing—since it looks like what you have are S-corporations, maybe three, maybe not—is you might look at doing the C-corporation because the C-corporation allows you to have a lot more control over what income is going to be on your personal tax return versus an S-corporation where all of the income is going to flow through to your personal tax return. What you’re in control of there is how much of it you’re going to pay payroll tax on. You can control how much you’re going to take out of the S-corporation payroll versus how much you’re going to take out of the corporation as what is referred to as a nondividend distribution.

Ultimate question here seems to be, “How should I pay myself from each one of the businesses for tax benefit?” It really and sincerely depends. We simply don’t have information in this question. But if we are talking about an S-corporation—as I assume we are because we’re on payroll and we’re receiving a K-1—you really just have to look at making sure you’re only paying yourself a reasonable salary. You’re not paying yourself more than that, subjecting yourself and your S-corporation to increased payroll taxes. 

After that, it’s a matter of doing reimbursements from your S-corporation for your out-of-pocket expenses. Maybe the 280A meeting room deduction is a way you can get income out of the S-corporation tax-free. There are some options in doing that, but it’s going to have a lot to do with tax planning.

Jeff: And it all goes back to what you said originally with, this is a fine line you’re walking. You can either have good income for loan purposes or bad income, lower income, for tax purposes. Every time you come up with an additional deduction, you’re hurting yourself on the loan side.

The good news is since this is an S-corporation, lenders tend to take more into account for the income coming from those. If these properties were just owned in your name, they tend to acknowledge about 70% of the income coming through from the individually-owned. 

Possibly, what you may want to do is build up a war chest. It may take you a year or two before you can make your next move. We do see this fairly often with people who are highly leveraged in their properties, and they can’t pull the trigger onto the next property. 

One thing you may want to consider, fortunately, this usually only affects when you use cost segregation where you’re going to cost segregating those properties. You’re going to take a hit on income in one year, possibly be able to roll it the other years, but that’ll be another question you have to answer with lenders on why your income is so low.

Toni: But you have more control over that, too. People are led to believe it’s some juncture. Everybody gets very excited about the cost segregation. I don’t blame them. I do, too. But the piece of it that they get caught up on is the bonus depreciation—which we’re going to talk about later—that we can go ahead and reclassify in a cost segregation all of these expenses that are not structural components. We can accelerate them and deduct them all in the first year. 

That’s true. There’s no falsehood there. But what you’ve done is you’ve taken out your structural components and reclassified them as personal property, which is going to be depreciated over shorter periods, so 5, 7, 15 years. Nobody said you have to take the bonus depreciation and put them all in the one year. Look at it and see. Maybe you just take the 15-year property, or maybe you just take the 7-year and leave the 5 to depreciate over that 5-year period so you could spread out that benefit, but at least it’s not 27½.

Jeff: And if you have three businesses, all of real estate in them, you don’t have to cost-seg every single one of them this year. You could do one this year, one next year, and one year after that. You’re kind of spreading out that deduction.

Toni: Anything you want to say? 

Jeff: No, I think I’ve said enough. 

Toni: We’ve done that question to death? Okay, next one. “Do wholesalers of land need to pay self-employment tax?” Possibly. 

Jeff: That’s a ‘depends’ question. We think of wholesaling as you buy the land, you sell the land. You don’t do anything to the land. 

Toni: I don’t think of it as buying and selling. You’re selling the rights to the contract when you’re wholesaling. Unless you’re a wholesaler, that’s double closing. It can work out both ways, but at the end of it, the income we’re talking about, whether you’re using a wholesale trust, whether you’re doing a double close, which by the way I typically recommend. Going the way of the wholesale trust because the double close can hit you with additional paperwork and expense, but it’s deductible. At any rate, the income earned through wholesaling is going to be from a fee, almost like a finder’s fee. That is going to be ordinary income. 

The question is are you doing it in your personal name? If you are double closing, you’re buying and selling real estate, and you’re doing that in your personal name, what comes next? […] which we don’t love because that comes with a whole host of other problems.

Let’s just roll back to the actual question. “Do I have to pay self-employment tax?” Yes. Reel me back in. I’ve been hanging around Toby too much. 

“Do I have to pay self-employment tax on it?” It depends on if you’re doing it in your personal name or if you are doing it in an LLC taxed as disregarded, meaning in the eyes of the IRS, it is non-existent and it is simply reported on your personal tax return. In that event, yeah, it’s going to be subject to self-employment tax. 

However, if you are wholesaling which we more so recommend in a corporate entity, be it an LLC taxed as a corporation, be it that you’ve left it a C, or you make the S election, that way, you do not have to pay self-employment tax. If you’re a C-corporation, obviously, C-corporations don’t pay self-employment tax. If you’re an S-corporation, the income flowing through is not subject to self-employment tax. However, you are going to have to pay yourself a reasonable salary which people get tripped up on a lot on because the IRS is so good at explaining things like reasonable, right? 

To be more specific, the IRS does not define what reasonable means, so we have to come up with what reasonable means when we’re using an S-corporation. I know that’s not the question so we won’t deep-dive into that right now. But suffice to say, if you are wholesaling, that is going to be ordinary income. If it’s reported on your personal tax return, it is going to be subject to self-employment tax. What’s the answer to that? Don’t report it on your personal tax return. No. Put it in a corporate entity so we can avoid all of that madness.

All right. Next one. “To maximize tax benefits as a realtor, is there a catch to it being your full-time business? I have a salaried job that I rarely work more than 20–30 hours a week and do a realtor business as well. Is there a catch that limits some tax breaks if real estate isn’t considered my main job?” 

Jeff: There’s really nothing I’m aware of just because you’re a realtor. Lots of people are realtors as a second job. I think what might be confusing is real estate professional versus realtor. With a real estate professional, it’s being somebody who’s in the business of renting out properties to others. 

Toni: I picked this question for the very reason that you’re getting into right there. There is the confusion of qualifying as a real estate professional per IRS definition and being a realtor. You actually don’t have to have a real estate license to qualify as a real estate professional per IRS. It can help, and I know that we have a lot of people who invest in real estate who like to have their license so they have access to the MLS, but you don’t have to be a realtor to qualify as a real estate professional. 

Jeff: Right. It is helpful especially if you’ve spent a lot of time doing real estate that you can make yourself a real estate professional. Also, one of the issues with being a realtor, in many states, they have to be a realtor in their name which means they’re subject to self-employment tax, to what we were just talking about in the last slide. 

If you can, I normally suggest that you try to be a realtor through an S-corporation. Sometimes, certain states make you register that entity as a brokerage, not just a real estate company. Again, this is something you have to check on state by state. 

Toni: Yeah, and to your point, there are certain states and I’ve seen it in states where it’s allowed for you to receive your real estate commissions through the S-corporation as long as the 100% sole owner of the S-corporation is a licensed real estate agent and the broker still refused to pay the S-corporation because of their understanding and interpretation. That’s okay. There are just extra steps we have to go through to work around that and we do have those extra steps for you. 

In this one, they say, “I have a salaried job and I rarely work more than 20–30 hours and do realtor business as well.” Let’s assume there that this salaried job has nothing to do with real estate, but if it did, do we have to be more than a 5% or 2% owner to be able to count that in your real estate professional time? Do you remember?

Jeff: I do not remember.

Toni: I want to say 5%. As long as you’re a more than 5% owner in that business and it is related to real estate, you can actually still count the time doing that salaried position in your hours for real estate professionals. 

What am I talking about when I say hours for a real estate professional? In order to qualify as a real estate professional under IRS terms, you are going to need to meet two tests, one of them being a two-prong. First one is material participation test. I believe that’s seven different tests that you can meet, but there’s really only the three that stand out. That’s the more than 500 hours in real estate; you can do that with aggregating. There’s the more than 100 hours in significant participation or something like that. Then, there’s the no one else spent more time than me on the activity to meet material participation. That’s one. 

The second test is two-prong. It’s more than 50% of services performed in real estate and at least 750 hours logged for real estate. When you marry those two things, more than 50%, if I work 750 hours W-2, I have to have 751 hours logged. 

Jeff: Let’s use this example. Say she’s working 30 hours a week. She’s going to have 1500 hours at the end of the year. You have to have more hours of that in your real estate activities than what you have in your non-related job. 

Toni: If you actually are a realtor, you can include that time when you are logging these hours as long as you are a more than 5% owner of the real estate business. If you’re a realtor who’s simply receiving a 1099 for their commissions, then you’re a sole proprietor. 

Jeff: You’re the 100% owner of that business.

Toni: Exactly right. “Is there a catch that limits some tax breaks if real estate isn’t considered my main job?” That’s the whole point. If you can qualify as a real estate professional, that takes your income or loss, I should say, from the real estate activity from being passive to being non-passive. 

Non-passive losses, unlike passive losses, are deductible against your ordinary income. That’s the real reason why you want to qualify as a real estate professional. There may be a considerable tax break for you. You’re experiencing paper losses especially with the cost segregation if you can qualify as a real estate professional. 

They’re just smashing through the questions, aren’t they?

Jeff: I just noticed that. We do have a number of people. Piao in tax. Christos is helping out. Eliot from your department, one of our tax advisors. 

Toni: One of my guys, so you can trust him.

Jeff: Tabia is on the help with bookkeeping. Who am I missing? I know I’m missing somebody. If I’m missing, I’m thinking of you. 

Toni: You’re in here.

Jeff: Toby has just put out this new book, Infinity Investing. If you’ve been on Tax Tuesday before, you’ve heard him talk about it. Infinity Investing is Toby’s get-rich-quick book. It’s absolutely not that—

Toni: Get rich slow.

Jeff: Get rich slow. It’s about smart investing, building up, I like to say your war chest, so it becomes impossible to spend the cash flow without a really bad drug or gambling habit. 

Toni: What I can tell you is I actually did attend the very first Infinity Investing. That contained a lot of what’s in this book. I tell you, it completely changed the way I thought about net worth and things like that, the power of passive income where you can get it. You guys might want to check that out. 

Jeff: There’s the link for it, aba.link/infinitybook.

Toni: Back to the questions. “Could you please review how LLCs can work with 501(c)(3)s for both to maximize benefits? The LLC being a for-profit and the 501(c)(3) being non-profit. How can they interface without violating any tax codes?” Very carefully. No. I guess it really depends on what kind of LLC we’re talking about and really what it is you’re trying to accomplish by moving the funds out of your non-profit into your for-profit. 

Jeff: Let’s start where we usually see LLCs working within the 501(c)(3). If the 501(c)(3) is doing affordable housing or things of that nature, we may put one, two, or three LLCs in there to protect the properties from each other.

Toni: The LLC is disregarded to the 501(c)(3).

Jeff: Yes, exactly. What she said.

Toni: You got to be careful with that, too, on a state by state basis because not all states allow the disregarded LLC to benefit from the 501(c)(3)’s tax-free status, tax-exempt status. Texas being one of those states. We had several LLCs disregarded to a non-profit, and then we had to go in and get the exempt status for every single one of those disregarded LLCs. You want to be careful of that. Just make sure you’re working with a non-profit specialist when you’re setting these kinds of things and structures up.

Jeff: As far as a for-profit LLC that is maybe disregarded to you or that you have ownership in, working with a 501(c)(3) that you set up and donated money to can be a really heavy proposition. Like you said, it depends on what the relationship is, what are they doing. 

If the LLC is a real business and they’re selling stuff to the 501(c)(3) at fair market value—what they would sell to the public for—that’s one thing. It’s when you start getting into bargaining issues where you’re lowering already lower prices, or worse, even higher prices to the 501(c)(3) for you to get a bigger deduction or whatever. That can really be a problem.

Toni: I suppose if the LLC is not a related party to the 501(c)(3), then you could contract that LLC for services and the 501(c)(3) would be able to pay the LLC for services. I find no difference in that from just paying yourself a salary for working for the 501(c)(3), especially if the LLC is a disregarded entity to you personally.

Jeff: An important role to remember is arms length transaction. If it’s between the for-profit LLC and your non-profit, it really needs to be an arms length transaction—everything at fair market value. If you’re paying yourself a salary, it’s got to be what is a reasonable salary for what you’re doing for the non-profit. We’ve seen where people will put in $200,000 into a non-profit and then want to pay themselves a salary of $100,000 out of the non-profit. That doesn’t really work.

Toni: Let’s go the other way around and the LLC is making contributions to the 501(c)(3) because that could be another situation. With that, I would only recommend that you make a charitable contribution from an LLC to a 501(c)(3) if that LLC is taxed as disregarded or maybe a partnership because that way, it’s just going to flow through to your personal tax return and be subject to the charitable contribution limits that you have personally which is far more beneficial than the corporate charitable giving deduction which is what, 20% of taxable income for corporations?

Jeff: Corporation is 20%. I’d love to see that drop. 

Toni: Is 20% under CARES? It was 10%.

Jeff: Right. It was 5%, then was raised to 10%, and then 20% under CARES. Correct.

Toni: But for at least 2020 and 2021 under CARES, 100% of your AGI is what you’re able to donate and deduct on the personal level. You could see the difference there. Big difference. You can go three ways with the LLC’s relationship with the 501(c)(3). You can have an LLC that’s disregarded to the 501(c)(3) or even owned by the 501(c)(3) so you could separate out some of the assets. You can have a services relationship between the 501(c)(3) and the LLC. Or you can have the LLC making charitable contributions to the 501(c)(3). All of which, I don’t know if I’d say we ran down the pros and cons, but touched on.

Jeff: Now I’m going to change it a little bit before we move on. What if this LLC is a corporation?

Toni: In what direction?

Jeff: Either way but more likely, say the corporation is selling services to the 501(c)(3). Is that corporation a big enough cut-off between the grantor and the 501(c)(3)?

Toni: I think so.

Jeff: I think so, too. Okay, you can proceed.

Toni: But again, if it’s an LLC taxed as a corporation, that’s exactly when we say no. You don’t want to go the other way, meaning putting money, making charitable contributions from the LLC taxed as a corp to the 501(c)(3) unless you get that 20%. All you get is 20% of taxable income of the corporation.

Jeff: Yeah. I’ve seen a lot of people who make donations through their corporations, especially mostly only 5%. They’d make a $10,000 contribution to be able to deduct a couple hundred dollars.

Toni: And did not understand that that was not going to be the case.

Jeff: That’s why we have somebody else who can explain it to them.

Toni: You get told charitable contributions are deductible about up to 60% of your adjusted gross income. The thought is that that is going to apply to all my business entities and myself. Just for clarity sake for you guys today, you heard it here first at Tax Tuesday. That is not the case.

Let’s move on unless Jeff, you want to interrupt again or are you good? You good? Okay. Next question, “If I run my real estate business from home, can I deduct a portion of all home expenses, i.e., property tax, utilities, insurance, et cetera?” 

Jeff: As the question’s written, yes, but there are a couple rules. We talked about home offices. We’re talking about a Schedule C, a sole proprietor. It does have to be exclusive and regular use of that space. If that’s the case, you have a home office. You do all your business there. It’s also supposed to be your primary place of business.

Toni: That’s a good question. What you’re talking about is the business use of home deduction that we get to take on our 1040, but we’re talking about real estate. Let’s assume we’re talking about rental real estate.

Jeff: So we’re talking about reimbursements, not home office.

Toni: They didn’t say they had a corporation. This is how we work, folks. You guys think you’re sending us these simple questions and we have a million more to throw back at you. Just starting bare-bones is where I’m going to go with this, just face value. “I’m running a real estate business from my home.” Let’s say we’re doing it in our personal name. Don’t do that. And let’s say this real estate and add this fact, I’m adding this fact, but let’s say the real estate business is rentals. Now what? We’re done. There’s no business use of home deduction on a Schedule E page one, right?

Jeff: No. I think in that case, if it was rental properties, that’s really when it comes into play. I want to have a corporation to manage my rentals.

Toni: Yeah, because rental real estate on the personal tax return is considered passive activity and investment. In order to be able to do business use of home, we wouldn’t be able to do that in 2017, but in 2018, the Tax Cuts and Jobs Act took our investment expenses off Schedule A. We can’t do that. 

The next option is to what Jeff was just talking about and getting yourself into a corporation as a management entity.

Jeff: In that case, you’re considering your corporation is actually managing rentals. They could be collecting rent, paying expenses, just managing your LLCs as a whole. Then, you can pay that corporation to do that. 

They can also reimburse you for the use of your office, what we would call an administrative office, not a home office, where the corporation works out. Those reimbursements include the items we have here, property tax, utilities, insurance, numerous other things, repairs, direct expenses to the office.

Toni: I get this question a lot. Oh, you were going into the direct and indirect. Sorry, go ahead.

Jeff: Direct expenses would be expenses that only apply to that office space. You paint that off, that’s a repair for that office. You paint the kitchen, that’s actually not a deductible item. Period. Things that happen on the outside of the house—your pool maintenance, your house being painted, your lawn care—also does not get included. 

I’m sure we’ve talked about it in the past where you calculate all these expenses and then you deduct a portion of them based on square footage, number of rooms, or one of the other acceptable methods.

Toni: Someone says, “Schedule E, UBE—unreimbursed business expenses.” We are not on Schedule E page two.

Jeff: Unreimbursed business expenses are from an S-corporation or partnership, not from Schedule E page one.

Toni: One of the questions that we actually get asked a lot is where are you putting that on the tax return? I’m on my corporate tax return. I’ve reimbursed for all of these business use percentage of all of my indirect and 100% of my direct. I’ve given them to you and your team. Where do you put it on the tax return? What do you label it with? What do you classify that?

Jeff: The corporation side? You could list it as little as employee reimbursements or you could be a little more detailed and say, administrative office reimbursements. Whatever you feel comfortable with.

Toni: I like administrative office, I do. It doesn’t imply that you’re doing rent or anything like that, but I do like administrative office.

Jeff: Your corporation reimbursed you $10,000 over the year. Where do you put that on your 1040?

Toni: You put it in your pocket. Why are you putting it on your 1040?

Jeff: That’s exactly right. Reimbursements are not taxable to the recipient.

Toni: Ultimate answer to this question is yeah, under certain circumstances, you can take advantage of the business use of your home if you’re in the real estate business. 

If that real estate business is active so it lands on your Schedule C—you’re a realtor, let’s say—then you would be able to take the business use of home deduction on the 1040. If it’s rental real estate, that’s Schedule E. You’re not going to be allowed that deduction. We’re going to recommend you go with a corporation so you can reimburse. 

To the point Jeff was making a moment ago there, within in turn, making management fee payment to our corporation which is a deduction on your Schedule , page one.

“Startup S-corp has no revenue yet. If I file tax jointly with my husband, any concerns?”

Jeff: We need a seeing-eye dog or something?

Toni: No. Not to the dog, but no to the question. None really that I can think of, Jeff?

Jeff: The only concern would be if your husband doesn’t know about your S-corporation. You might want to tell him beforehand. 

Toni: It will cause some marital issues here. 

Jeff: But I want to go back to the very first part where you say, “Startup S-corp has no income.” Because it is an S-corp, it still has a requirement to file a return, issue K-1s. It may not have a thing on them, but it still has to go through that process. 

Toni: And it might have deductions and you’re capturing your startup expenses on that first return. If it has deductions, no income, you’re going to have an S-corporation with a loss which you potentially can take on your personal tax return depending on what other kind of activity you have. 

Just keep in mind that S-corporations are also subject to the hobby loss rules so we just have to make sure that the S-corporation is profit-motive. If you do have losses in the S-corporation two out of the five tax years, it could trigger you for inquiries with the IRS to make sure you are in business with a profit motive in the S-corporation. But honestly, S-corporations are just so limited.

Jeff: Yeah. You know she said a profit motive, not profitable. You have to be able to prove that you are attempting to make a profit in your S-corporation or in any hobby. 

It’s a very subjective test. We always talk about the three out of five profitable years. That’s just one of about a dozen tests that they look at for profitability.

Toni: They look at a lot of factors but the three out of five is just for safe harbor. If you’re profitable three out of five years, they’re not going to look at you.

Jeff: Yeah. If we apply that to all entities in Uber, DoorDash, and a couple others, Tesla would’ve been a hobby for the past 10 years.

Toni: Basically, if you enjoy doing it, it’s a hobby. This is a hobby for me then. If Toby watches the playback on this, I would still like to get paid for this hobby. Please and thank you. Anything else to add to that one?

Jeff: No.

Toni: All right. Very good. 

“What is the best way to pay your children (teenagers) when they work in your business? Payroll, cash at time of service, then year ending 1099?” A couple of things that I will open up with. Glad that you mentioned that it’s a teenager because the question that comes up a lot is what is the age limit on when I can hire my kids? Can I hire my one-year old? Can I hire my two-year old? There isn’t one. You can hire your children to work for the business as long as they’re capable of doing what you’ve hired them to do. 

You can’t say that you hired your toddler—I know you probably wouldn’t—to do janitorial work. […]. I have a 19-year old. She’s better at some of these social media. She knows more about a lot of that stuff than I do, so I can hire her to handle my social media marketing, networking and things like that, setting up my website, and so on and so forth. I could pay her at market rate for those services.

Then, we have people who hire their toddlers, their babies, whatever as models for marketing materials and such. That’s something that the child would be capable of doing, so just keep that in mind. When you’re going to pay your children, first you have to figure out what they are capable of doing and what they are going to be paid for doing that.

Now, the best way to pay them, I’d say, number one is if you are hiring them through an entity and LLC that is disregarded to you or taxed as a partnership with only the parents as the members of that LLC, you can pay them W-2 and they would be subject to FICA. No unemployment on that either, right?

Jeff: No. I don’t think so.

Toni: No unemployment on that. I know you don’t do unemployment if you hire a spouse or is it siblings?

Jeff: I’m not sure about the siblings, but I know what you’re getting at.

Toni: Spouse or parents. You have those. But if it’s your child, you’re getting around payroll taxes if you’re doing W-2 from an entity that’s disregarded to you. You have to do the W-2 so you have to do the payroll recording. You actually have to run the payroll. 

Another good thing when you’re doing that is if you pay them under $12,000, they’re not going to have to pay any tax because that’s going to be their standard deduction. Now, you can even pay them another what? Is it $6000 for IRA contributions?

Jeff: If you want to make it traditional, but we often recommend that they do the $12,000 put it all into a loss.

Toni: Okay. You could do that, too. 

Jeff: But to your point, if they want to put in a traditional IRA, they could pay them $18,000 and not pay a dime on tax.

Toni: Exactly. Another way to do it is if you’re going to pay them directly from the C- or S-corporation. If you’re going to pay them directly from the C- or S-corporation, they’re going to be subject to payroll tax, so you may as well just do it with a 1099.

Jeff: Now, I’m going to object to that because I’ve been thinking about this. You would think that they would be equal because the payroll tax on one side’s going to be the same as the self-employment tax on the other side, correct? 

Toni: Yeah.

Jeff: But one difference is if I’m paying payroll tax on your check, I get to deduct that on my entity, so it does lower the income at that point.

Toni: But don’t you get the ½ self-employment tax on the […] as an adjustment?

Jeff: Yes, you do. I […] to you before the W-2s. It establishes payrolls. Well, it’s going to establish payroll taxes either way, social security and all.

Toni: Well, here’s why I like the 1099. I’m going to tell you why I like the 1099. It’s simply because what I can do now for my corporation is I can set up an LLC where my child is the member-owner of the LLC and I’m the manager. I retain control over that LLC and they can’t go off spending all of the money that I’ve paid them—W-2 or 1099—on a kegger. There, I maintain control so I can make sure that they’re spending the money the way that I intend it for them to do it. In that way, if I’m doing this, let’s say to help them save up for college instead of just putting it into a college fund or whatever, I’m going to pay them so I get a deduction from my business, and they have money now in an LLC to pay for their college expenses, their room and board, whatever ancillary expenses they may have as it relates to going to school. I retain control of the LLC. That’s why I like it and I also think that the 1099 just makes for simpler reporting.

Jeff: I will give you that, that the payroll reporting is a pain following quarterly reports and annual reconciliations.

Toni: Especially if your child is the only employee that you have. If you have a battery of other employees, it makes no difference adding one more. 

Jeff: Now, what if I have a C-corporation, I’m hiring my minor child, and I’m paying them payroll. If I have a 401(k) plan, can I bring them into that?

Toni: Yeah. Oh, did you say if you’re paying them 1099? 

Jeff: No. 

Toni: Okay. If you have a 401(k) and you hire your child W-2, if you didn’t offer them participation, that would be considered discriminatory, wouldn’t it?

Jeff: Yeah, but I know some of the plans have age limitations.

Toni: Oh, I see where you’re going with that. I think you’re good.

Jeff: I think most of the plans, you could still add them.

Toni: I think so.

Jeff: You may also add them through a medical reimbursement plan. 

Toni: Don’t ever ask questions you don’t know the answer to. I only ask questions I know the answer to. Anything else you wanted to add to that one?

Jeff: No. I’ve been told not to. 

Toni: All right, let’s keep rolling. Oh, was that it?

Jeff: No. We have a number of different ways to follow Anderson, Facebook, Twitter. Do we have Twitter?

Toni: Yes. 

Jeff: We have a number of different methods. You can see them all in the slide. Your eyes are probably better than mine. On social media, we also have—I think we may talk about this later, some of our YouTube and things of that nature—tons of material out there for you to look at. 

Toni: Stay up-to-date on our upcoming events, webinars, live streams, things like that. Again, we are such an education company. We want to make sure that if we know, you know. If you follow us on social media, you’ll know.

Jeff: One of the reasons frankly that I like for people to know this stuff is it makes my life so much easier.

Toni: It makes pretty easier conversations.

Jeff: Yes, it does.

Toni: We’ll keep rolling. This one looks a little bit of a mouthful. “I reimburse myself for my health insurance premiums through my C-corp. My fiancé and I are planning to get married later this year and I will become eligible to get my health insurance through her employer. Is it permissible to reimburse her for my portion of the premium through the same C-corp? This is an entity that was set up by Anderson Advisors.”

Jeff: Here’s what we got. Let’s say that your fiancé currently has all of her insurance paid for by the employer. Once you get married, you will be on her plan and she’s going to have to pay for your portion of the insurance. 

Now comes in the ‘that depends.’ The payment is (say) $500 a month. If that $500 a month is going through a pre-tax plan—a 125 Plan, Cafeteria Plan, whatever you want to call it—you’re already receiving the tax deduction for that. If it’s not, if it’s $500 that you have to fork out, to pay for to keep you healthy, that $500 can be reimbursed by the corporation. It doesn’t matter if it’s your wife’s plan. Once you get married, you’re in this together. That’s how these accountable plans are treated and medical plans. You are one entity inside this entity.

Toni: You don’t actually have to be married to be able to reimburse for her plan. You have to be married in order to benefit from her plan, but you don’t have to be married in order to reimburse her from this plan. If she’s an officer, director, or employee of the C-corporation, she can participate in the plan.

Jeff: Right.

Toni: Anything else to add to that one? I think I’m good, too.

“Can you explain how to invest in stocks from an LLC? How is it beneficial? What are our write-offs if we are investing in stocks?”

Jeff: We got to start using smaller words.

Toni: “How to invest in stocks from an LLC?” Number one, you have to set up a brokerage account in the name of the LLC, or you’re going to have to transfer your brokerage account if you just have one in your personal name to the LLC. You’re just going to have to contact your brokerage firm if you have a current account to see if it is going to be possible for you to do that.

Jeff: Have you seen some issues with that? They’ll try to trade through an LLC or an entity, that they want to charge you more money?

Toni: Not as often as you think. There are some brokerage firms—we really should probably compile some sort of a list—that will charge professional fees when you put your brokerage account in an LLC because they are classifying you as a professional. I just told them I’m not a professional. I know nothing. It didn’t work. Anyway, there are ways around that. That is just to use a personal property trust, put the brokerage account into the personal property trust, and have the beneficiary of that professional property trust be the LLC. 

Ultimately, what we’re looking for in investing in the LLC is asset protection, so we need that personal property trust beneficiary into that LLC still. We still want an LLC for aggregate liability. We don’t think anybody is going to slip and fall on one of your stocks, but you probably will at some point—hopefully not—have some outside liability. 

Toby likes to say, if your teenage son is driving your car and runs over a gaggle of nuns, you now have outside liability. If the brokerage account is in your personal name, it’s going to be up for grabs in any litigation. We’re doing the LLC for asset protection and how we put that brokerage account into that LLC is going to depend on the brokerage firm. 

Again, if you already have the brokerage account in your personal name, contact the brokerage firm and just let him know, hey, this is an LLC that’s disregarded to me personally. I still retain control. It’s going to be reported as a personal tax return, and so on and so forth. Just explain it to them. If the brokerage firm is going to require you to close your positions in order to open them up back in the LLC, of course, we’re not going to recommend you do that. You’re just going to start a new brokerage account in the LLC and systematically start moving things over. 

There is no tax benefit if you just have a brokerage account in an LLC that is taxed as a disregarded or partnership. To get tax mitigation, you have to have a corporate entity. Whether that means we’re just going to have the LLC taxed as a corporation—because we do that, too—or that means we’re going to have the LLC, make it a partnership with you being the individual, being the majority partner, say 80%, and the corporation being minority, say 20%. In that way, we’re getting our income shifting or income splitting, however you want to say it. 

In that case, we have a brokerage account. The tax benefits would be, off the top, 20% of my capital gains are not going to hit my personal tax return. It’s going to go up to the corporation. I’m going to be able to take all these lovely tax deductions that I’d be able to take on a corporation that I’m not otherwise able to take on it my personal tax return. I like the medical benefits; we had someone asking about it a while ago. 

Jeff: Here’s the important thing that Toni brought up much earlier, one of the earlier slides. The investment expenses were deducted under miscellaneous itemized deductions. Those are gone. However, if we have the corporation managing the trading or managing the LLC, perhaps we’re giving them a guarantee payment. We’re not giving them a management fee. We never want to do that. Maybe, we give them guarantee payment.

That corporation can pay those expenses directly, whether it’s to buy software, buy articles, or whatever it may be—those types of investment expenses—and write those investment expenses off as ordinary expenses. It gets whatever payment they are receiving from the LLC.

Toni: We have someone in the chat. I’m going to feed into it even though we want you guys to ask your question in the question and answer. I can’t help myself. 

“New to the term disregarded. Would you please explain it?” Disregarded is a federal term mostly in it. It just means that for federal purposes, the IRS does not recognize the LLC and it’s just going to be reported wherever it’s required to be reported on the owner’s tax returns. If you’re the owner of the disregarded LLC and you are flipping real estate—I don’t know why I chose that—it’s just going to get reported on your schedule C as if the LLC didn’t exist.

Jeff: It basically means that we don’t pay any attention to it. It’s disregarded. Who owns this LLC that you keep talking about?

Toni: It’s an asset protection tool, it’s not a tax tool. It doesn’t become a tax tool until you elect the corporate status. 

Jeff: A disregarded LLC is always going to be a single-member LLC. Once you add a second member, it’s a partnership or something else.

Toni: Unless you’re married filing jointly in a community property state. You hate me, don’t you? 

Jeff: I like you because I have to. 

Toni: “What are our write-offs if we are investing in stocks?” It depends. If we’re treating this as a business activity, you now have an LLC taxed as a partnership with the corporation being one of the partners. Now you spun off this corporation into an actual business that is in the business of managing other business entities like our LLC. It’s the managing member of the LLC. That’s what is in the business itself. 

Now, as that managing member, I’m going to be writing off any mileage concerns to any travel I have to do related to the activity of managing—my cell phone expenses, my internet expense, my administrative office, so on and so forth. Ordinary business expenses is what I’m doing in the corporation. 

I see LP managed by a C-corp. It’s not an LP. An LP is a limited partnership and that’s not the direction you want to go in. It should be an LLC managed by a corporation. Unless of course, if you already have an LP. If you do, it’s perfectly fine. 

Jeff: The LLC is the preferred way to go now since the Tax Jobs and Cuts Act. 

Toni: Correct. That takes care of that. What do you think?

Jeff: One of the examples in the good old days. Some brokerage firms were charged thousands of dollars a quarter a month for advisor’s fees. People would write them off under miscellaneous deductions under itemized deductions. Since we can do that anymore, what we can do is throw those fees onto the corporation. Allow the corporation to deduct them.

Toni: Yeah. Exactly. We have someone else saying, “When you say LLC taxed as a corporation, do you mean an S-election status?” I do not. I mean C-corp.

Jeff: I had to learn to do that. 

Toni: What?

Jeff: I would either say S-corporation or corporation. I’ve noticed a lot of people, a lot of our clients, say S-corporation or C-corporation? I had to push myself into that direction.

Toni: Is that it? No.

Jeff: No. We are not done. This is what we talked about earlier about subscribing to Anderson Advisors’ YouTube. I think we’re on Apple Play or whatever it’s called now. There are tons of educational videos out there, free to look at. I think Clint’s producing more an hour or something like that. 

Toni: “Can I use an S-corp to serve as a management company for my real estate investment if my real estate is held by a Wyoming Holding LLC and Illinois single-member managed LLC? Are there tax benefits to this strategy?” Let’s set the stage so everybody can understand. What we’re assuming you’re doing is an Illinois single-member that’s holding the property and that single-member is disregarded to your Wyoming Holding LLC. The question is, “Can I use an S-corporation as a management company for the Illinois single-member LLC?” because that’s the LLC holding the property. Go ahead. 

Jeff: Yes, you can. That doesn’t mean yes, you should. 

Toni: I love you, Jeff. We are of one mind on this. Go ahead.

Jeff: When I see using especially from a disregarded entity and using an S-corp for a management fee, they’re basically doing this. We’re taking money out of this pocket and we’re putting it back over in this pocket. Nothing has really changed. That’s why we recommend using the C-corporation because the C-corporation isn’t you. The S-corporation is. Where you might use it if you have multiple members, maybe the ownership is not exactly the same. 

Toni: I would really only use an S-corporation if I was doing property management for properties I don’t own. But if it’s a property I own, I’m usually going to recommend a C-corporation for the exact same reason that Jeff is referring to there. 

Here’s the rub. S-corporations can take some of the same deductions as C-corporation can take. You have an accountable plan in an S-corporation because an S-corporation is considered a separate taxpayer where you’re concerned because you’re going to be paying yourself W-2 from it. S-corporations can have an accountable plan, so it can reimburse you for your out-of-pocket expenses. It can do the Section 280A meeting room expense deduction. It cannot do the medical expense reimbursement. I say it cannot but we’re not actually seeing anything that can and cannot.

Jeff: It’s an exception to the 2% […].

Toni: Let’s lay the stage if you did do it. Let’s say you did have a medical reimbursement plan in the S-corporation, and the S-corporation is reimbursing you and deducting medical expenses. S-Corporations, like partnerships, have to have separately stated items. It’s just going to be Schedule K: Separately Stated Item, going to flow through to your personal tax return onto your Schedule A. It just took the long way around to be subject to that 7.5% floor limitation on the medical expenses, which is why we don’t love it. We want to make those medical deductions on the C-corp tax return.

Let’s just say, for argument’s sake, I used my S-corporation. I did my accountable plan expenses. I did my 280A. We can do medical insurance premiums through the S-corporation. You have to add that in your W-2. 

Let’s say I did all of that stuff and it totals up to $20,000. I could do a management fee to the S-corporation of up to $20,000 and make a wash. No income is flowing through to me personally because it was net zero. You either want it to net zero or a loss. What happens to S-corporations that shows losses two out of five tax years? 

Don’t love using the S-corp. You also don’t want to misstep and end up with positive income flowing through to the S-corporation just like what Jeff was talking about. You’re just taking money out of one pocket and putting into another pocket.

Especially in the case of rental real estate. You’ve now taken passive income and turned it into active income that is required to pay you a reasonable salary. You potentially added a payroll tax to it. 

For a number of reasons, there aren’t really any tax professionals—at least none that should be still remaining in this building—who would recommend doing an S-corporation over a C-corporation. But can you do it? Yes. Where it has its place is if you are managing properties or anything for that matter that’s not your own. You can see why I picked that one, the passion. 

Jeff: I do. I need a tissue.

Toni: Oh, thank you. 

Next question. “If I have an S-corp, can I use a combination of Section 179 and 168(k) for equipment or business vehicles?” I guess we probably should start by explaining what 179 and 168(k) are.

Jeff: Section 179 is the election to expense certain items—newly-purchased items. Section 168(k) is what we call bonus depreciation. It allows you to write-off tangible personal property in the first year if the life of that property is less than 20 years. 

Here’s what it comes down to. With the exception of a few states where they’re a little quirky with 179 and bonus 168(k), bonus is going to take care of almost everything. There’s really no reason to use 179. Section 179 has more limitations than the bonus depreciation does. That will continue to be true until 2023.

Toni: In Tax-Wise on Friday, Toby was asking me, under what circumstance will one use Section 179 over Section 168(k)? It’s like, when 168(k) starts to phase out of this 100% bonus depreciation, then 179 might start looking a little bit more attractive.

Jeff: Let’s say we’re in January of 2023, the 100% bonus is onsetted. Is that a word? We’re looking at a 50% bonus now. That’s exactly what you’re talking about. I’m going to take a bonus of 50% on this new piece of $100,000 equipment I have, so I get a $50,000 of bonus depreciation. The remaining $50,000, I hit with 179. 

Toni: It seems like you were sprinkling it with 179, but that’s okay.

Jeff: One of the things with 179, let’s say we’re doing that. I have $50,000 179. I also have to have $50,000 worth of profit in that company before I take profit. That’s one of the rules for 179. You can only take it against your business income.

Toni: The question is, “If I have an S-corp, can I use a combination?” It’s not necessarily a matter of whether an S-corp. Section 179 and 168(k) is available to S-corporations, C-corporations, individuals, whomever. It just depends on the asset. 

Jeff: Section 168(k) is more flexible than 179 in almost every way you can think of. Section 179, we’ve talked about in the past. If you distribute something to yourself, there may be tax consequences of that. You have to look at how it flows through to you directly. From my readings, that doesn’t happen with bonus depreciation.

Toni: I have not seen that. All right. “Is it better to file married jointly or separately?” What say you, Jeff?

Jeff: Almost always. Not always, but almost always, it’s better to file jointly. The tax breaks are better. The brackets are supposed to be right in the middle. If I have $100,000 tax break here, then it breaks 50-50. On the other side, there are certain things that just go away or eliminate drastically whether they’re retirement contributions, student loan repayments, and so forth. You lose the tuition credit. I’ve always seen it in a couple states, Ohio being one of them because they have a joint filing credit. Somehow, it works out that it’s sometimes better to file separately in that state.

Toni: It’s always better to file separately when your spouse is engaging in criminal acts.

Jeff: True. If your spouse has also generated a lot of hacks that you didn’t know about, unpaid tax. You may want to file separately under the Innocent Spouse clause. There’s two of them—Innocent Spouse and Injured Spouse. If you want to avoid your husband’s/wife’s/spouse’s tax problems, you can. I’m not sure if it works in community property states as well. We’ll leave that for Toby.

Toni: Yeah, we’ll leave that for another day. But it’s true because your spouse is going to have to report their ill-begotten gains if they are engaging in criminal activity. However, you’re not allowed to take deductions against that income. For that and obvious other reasons, probably you should file separately under that occasion. To Jeff’s point, if you’re both law-abiding citizens, then 9 times out of 10, married filing jointly is going to be the best way to go. 

Next one. “Is it better for a single member LLC to file taxes as a disregarded entity or as a partnership? And why?” Actually, Jeff, you touched on that a little bit earlier.

Jeff: It is always better for a single-member LLC to file as a disregarded entity because it can’t file as a partnership. It’s only got one member.

Toni: Oh, that’s not how I read that. This is why I chose it. If you’re talking about a married couple, spouses—

Jeff: You’re good at the supposing part. 

Toni: I answer Platinum questions. I’m only the one that you guys are getting out in the 2–3 business day turnaround time. Those are me. Let’s see. If you are in a single-member LLC and you’re married, filing jointly in a community property state, you have the choice between being a disregarded LLC or a partnership. 

If you are married, filing separately or if you’re married, filing jointly and you’re not in a community property state, you have to be taxed as a partnership unless you work your way around that by using a living trust.

But why is it better one over the other? In one instance, it helps to clean things up a little bit for you on your personal tax return. In the event that you’re being asked to show the personal tax return, it’s not going to list every single one of your properties. 

Let’s say you’re a real estate investor. It’s not going to list every single one of your properties on the Schedule E because all of those properties are going to be on the partnership tax return that’s going to be separate. 

Also, to a point Jeff was making earlier, it makes you better lending-wise. If you have a lender looking at your tax return, especially in commercial lending, and they’re looking at Schedule E, page one versus income flowing through a partnership which is on Schedule E, page two, you will get somewhere between 70%–80% on the Schedule E, page one whereas you get 100% on the Schedule E, page two partnership.

Jeff: I don’t know why, but that’s the way it works. 

Toni: They just don’t know. If they’re looking at Schedule E, page two, they don’t know it’s real estate. All they can see is whether it’s a partnership or an S-corporation and whether it’s passive or non-passive, but they don’t know it’s real estate.

If it’s on Schedule E, page one. They know it’s real estate and they treat it less favorably. That’s the part I don’t know why. I know real estate, but as not favorable? I’m not sure why it’s not as favorable. In their minds, Schedule E, page two is a business activity. 

I think that’s it, guys. That’s all of our questions we have for today, I believe.

Jeff: That’s a link to some of our podcasts. Can you see them? I can’t see. The font is really tiny.

Toni: It just is illustrating some of the podcasts we have available, too. Tax Tuesday is on there. We’ve got Erik Dodds. He’s one of our financial planners. He’s on there. Clint’s on there. Greg Boots has some content. I can see the pictures. He’s on there. You can catch a lot of good content. 

Jeff: Replays are in your Platinum portal. The reason I wanted to go with this is you can see so many Tax Tuesdays. I’m sure it’s the same for some of the other podcasts we do. If you’re a Platinum Member, you can see all of them.

Toni: Yeah. If you’re a Platinum Member, you go into the Platinum portal or go into our video content. You’ll see all of the replays of Tax Tuesday. Just scroll through for mine. You can see the replays of Toni Talks, Coffee with Carl, all of our fantastic contents there. There’s also a frequently asked question area for you. 

If you have questions, which I’m sure you guys do because you kept our guys busy today. We answered 139 questions and we still have 26 hanging out. If you didn’t get your question answered today, you can go ahead and send those to taxtuesday@andersonadvisors.com. We will come back here in another couple of weeks and answer some of those questions for you. You can visit our website at andersonadvisors.com. Is this email or visit? You can send Tax Tuesday questions on the website? 

Jeff: I don’t think you can send questions through andersonadvisors.com, but you can email on that. We will either answer those during Tax Tuesday or answer them straight to you. I know we do have some people trying to answer those questions that you send that may not get asked during Tax Tuesday. We appreciate the time you spent with us. Toby will be back next two weeks.

Toni: Next time.

Jeff: I appreciate you sitting in for him. It was fun to do.

Toni: Yes. Unfortunately you guys, this is not going to be ongoing. Toby will be back. 

I have someone asking, “As a Platinum Member, what number do I call in for the daily call?” It’s not a calling. You’re going to go on the Platinum portal. In the middle banner, you’ll see a hyperlink to log into our Zoom call, 4:00–5:00 Pacific, Monday through Friday with the exception of Holidays. 

Jeff: You’re late. 

Toni: All right. Thank you so much, guys.

As always, take advantage of our free educational content and every other Tuesday we have Toby’s Tax Tuesday, another great educational series. Our Structure Implementation Series answers your questions about how to structure your business entities to protect you and your assets. One of my favorites as well is our Infinity Investing Workshop.

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