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Office Hours Q&A 2023-12-19

December 19, 202353 min read

Welcome to our latest edition of Tax Sherpa's Office Hours! In this Q&A session, recorded on December 19th, 2023, our team, including Neal, the founder, and Serena, our Operations Manager, dives deep into the pressing tax questions faced by small businesses, solopreneurs, and 1099 contractors. From navigating the complexities of cryptocurrency taxes to understanding the nuances of business expense deductions, we cover a wide range of topics that are crucial for effective tax planning and savings. Join us as we unravel these queries, offering insights and advice to help you navigate the challenging world of taxes. Continue reading below to explore all the questions and answers discussed in this informative session.

Question 1: Cryptocurrency Taxes


In Section 1 of our Office Hours, we tackled the intricate world of cryptocurrency taxes. I emphasized the critical importance of maintaining accurate records, especially in the rapidly evolving sectors of Decentralized Finance (DeFi) and gaming finance (GameFi). Given the complexity and variability of transactions in these areas, meticulous documentation is key. I also highlighted the necessity of reporting all crypto transactions to avoid legal complications, underscoring that transparency in tax reporting is essential in the ever-watchful eye of tax authorities. This section serves as a crucial guide for anyone navigating the convoluted landscape of crypto taxation.

Question 2: Are Tax Payments Business Expenses?

In Section 2 of our Office Hours, starting at [00:17:50], we delved into the nuanced topic of whether tax payments can be considered deductible business expenses. The answer is not straightforward and largely depends on the specific business structure and the nature of the tax in question. For instance, in a personal scenario where an individual is employed and receives a W-2, the taxes owed on that income are not deductible for the individual. This segment provides a comprehensive look at various scenarios, emphasizing that the deductibility of tax payments as business expenses varies and must be evaluated on a case-by-case basis.

Question 3: Augusta Strategy in Court

In Section 3, starting at [00:24:50], we discussed the Augusta Strategy and its recent scrutiny in court. I explained that while the strategy remains valid, it's essential to approach it with caution and adherence to regulations. The court case in question demonstrated how excessive and unrealistic applications of the strategy can lead to its rejection. The court emphasized the importance of maintaining reasonable and justifiable expenses, rather than exploiting the strategy solely for tax benefits. This section serves as a cautionary tale, highlighting the importance of using such strategies within the bounds of legitimacy and always recommends consulting with a tax professional to navigate these complex scenarios.

Question 4: Red Flags in Tax Filings

In Section 4, starting at [00:25:40], we discussed the red flags in tax filings that often trigger audits. I highlighted how disproportionate home office deductions and inflated mileage claims are common audit triggers due to frequent misuse. Additionally, the misuse of fuel tax credits was identified as a significant red flag. These areas, often abused for larger deductions, draw scrutiny from tax authorities. I advised on the importance of maintaining proper documentation and making reasonable claims, underscoring the need for honesty and accuracy in tax filings. This section serves as a caution to be judicious and compliant in claiming deductions to avoid unnecessary complications with tax audits.

Question 5: Making Small Companies Less Owner-Dependent

In Section 5, which begins at [00:31:30], we explored strategies for making small companies less owner-dependent. The key lies in systematizing operations and empowering staff for greater autonomy. I discussed how, at Tax Sherpa, we are actively implementing this by building a robust team, where I continue to lead the strategy but have stepped back from day-to-day operations like doing tax returns. This shift was partly due to health reasons but also a deliberate strategic choice.

A pivotal reference in this discussion was Scott Fritz's book, which outlines a methodology for business owners to systematically reduce their operational involvement. The essence of Fritz's approach is identifying core business activities that only the owner can perform and gradually outsourcing or delegating other tasks. This process not only enables the business to operate more autonomously but also allows the owner to focus on strategic growth rather than being entrenched in daily tasks. The narrative provided a clear roadmap for business owners to start this transition, emphasizing the importance of careful planning, team training, and strategic delegation.

Question 6: Owner's Draw, Distribution, and Salary

In Section 6, starting at [00:46:00], we discussed the differentiation between an owner's draw, distribution, and salary in various business structures, focusing on their tax implications and legal considerations. An owner's draw is essentially the same as a distribution, often used interchangeably in partnerships. However, in some cases, partnerships may have a guaranteed payment, sometimes referred to as an owner's draw, which effectively serves as a substitute for salary. This guaranteed payment carries similar payroll tax implications and is typically a fixed amount paid to one or more of the owners. Understanding these distinctions is crucial for business owners to make informed decisions regarding their compensation and to comply with tax regulations. This segment of the video provides essential insights into navigating these aspects of business ownership, highlighting the importance of aligning compensation structures with legal and tax requirements.


As we conclude this insightful session of Office Hours with Tax Sherpa, let's reflect on the key takeaways from our discussion. From the intricacies of cryptocurrency taxation and the nuances of deducting tax payments as business expenses, to the judicial perspective on the Augusta Strategy and identifying red flags in tax filings, our journey has been extensive. We also delved into making small companies less dependent on their owners, highlighting the importance of systematizing operations and empowering staff. Furthermore, we unraveled the complexities around owner's draw, distribution, and salary in various business structures, emphasizing their distinct tax implications and legal requirements.

Each of these topics underscores the diverse challenges and opportunities in the realm of taxation for businesses and individuals alike. While we've provided a wealth of information, remember that every situation is unique and benefits from personalized guidance.

If you're seeking tailored advice to navigate these complexities and optimize your tax strategy, we encourage you to book a discovery call with us. Our team at Tax Sherpa is dedicated to helping you understand and make the most of your tax situation. Click on the 'Book an Appointment' link here on our site to schedule your session. Let us help you embark on a path towards more informed and effective tax planning.

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[00:00:00] Hey, everybody, it is six o'clock at least where I am this Tuesday, which means it is time for Tax Sherpa live. And this week is office hours. This is just [00:00:10] open Q and a, where you can ask whatever you like. I will say that I will take any question. I'm not qualified to answer any question, but [00:00:20] anything tax related, I'm good.

If it's if it's outside that meeting of life, I'm happy to take a stab at it. But your mileage may vary. Yeah. Office [00:00:30] hours is just once upon a time I was a graduate student and I had to have office hours as a TA. Just people come by and ask questions.

And that's how this whole thing works, so we have [00:00:40] questions from the live audience. I see one already in from arrows. And we've got questions that have come in from clients and people we've talked to over the past couple of weeks. Actually just got [00:00:50] off a call with somebody and we'll get into some of the questions there that were brought up.

Because it's actually pretty important as far as what to do when your [00:01:00] relationship with a tax person goes bad. So that is something, unfortunately, we are. On the fortunately for us, because, we pick up our clients, but [00:01:10] unfortunately for the people involved, that can lead to a lot of stress and problems.

All right. So let's get into it. So who am I, who are we? [00:01:20] We're Tax Sherpa. I'm Neil founder of Tax Sherpa. Serena here is our ops manager. She keeps the ship running. And I do these days my [00:01:30] job is mostly strategy where. We will work on client's positions and figure out what's the best way to do things.

And then things like this, where, I'm out [00:01:40] there, I'm the pretty face. dOne over 50, 000 tax returns, quarter billion dollars with the payments processed billions of dollars worth of client earnings, all of that [00:01:50] kind of stuff. Our site taxsherpa. com. You can find all the important things there.

You can book an appointment. You can read our blog publish a new blog yesterday. I think it was yesterday. We try to keep that [00:02:00] up to date. So be sure to check that out. This is me. So my story of how I got into the tax world is an [00:02:10] unusual one. I went to school for engineering, not for accountancy, which is how most people get into the tax world.

So I went to school for engineering, got [00:02:20] all the way through my, or to my senior year was interning out in Texas in Austin, and then I realized that I didn't want to do this anymore. So [00:02:30] I can actually pinpoint the moment. So I was I was working for AMD, which is Intel's competitor to make computer chips.

And I happened to be there during the [00:02:40] time that the first one gigahertz processor was released. It was a big deal stock shot up to 60 bucks or something. All of my employee stock purchase plan shares [00:02:50] were locked up for a year. So I couldn't do anything on the pump, but it was nice to see at least.

And then towards the end of the term, around May or so we had a company award [00:03:00] ceremony and Joe, he got three patents, let's give him his plaque, let's give him a hand. He's a great company, man, et cetera. And this, the ceremony was, I don't know, [00:03:10] an hour long, something like that.

And the VP of I can't remember which VP it was, one of the VPs was doing the presentation. And the last one [00:03:20] said, this is a real special award. Bob here, he had a two week European vacation booked with his family approved months ahead of time paid for [00:03:30] the whole works. And he, when it came to crunch time and we had to get products shipped.

He canceled his plans and came into work like a good company man. And let's give him a [00:03:40] hand. Here's a plaque and people are clapping. And it was at that moment. Then I realized I'm never going to be able to work at a corporate environment. So [00:03:50] just, it's not going to fit my personality and that's not bashing anybody who does, but it's just for me, not going to work.

So thus began my [00:04:00] entrepreneurial journey. I read rich dad, poor dad, somewhere around there maybe a couple of years later. And that really lit a fire under me, did a whole bunch of stuff. Mostly failures, but survived long enough. And [00:04:10] then in 2007, I started getting letters from the IRS saying that I owed them 1.

3 million. And so that was the, my entry into the tax world. [00:04:20] That's quite, quite a brutal slap in the face, but. I've been through that whole journey where if you get a letter or letters, they'll send you, repeated [00:04:30] letters. If you ignore all those and the number's big enough, they will start sending you certified mail letters where you have to sign for them.

And if you ignore all those, you'll start getting phone calls from revenue agents. And if you ignore [00:04:40] those, they'll start going after whatever they can find bank accounts jobs. If you have high price assets like cars and boats and that kind of thing, they'll go after those. So I went through that whole [00:04:50] thing and.

In fixing my own problems this took years, by the way, this whole process. So it takes years to start and then it takes years to go through. So it took a [00:05:00] lot of willpower on my part to not fix my problem for that long. But I finally, when they started garnishing my wages from my job, I was tutoring high school kids at the time.

Then that [00:05:10] really got my attention because, I couldn't couldn't buy food. So that was a problem. And so it fixed my own problem. I ended up hooking up with this former wall street tax attorney. And he helped me fix [00:05:20] my problems. I ended up paying zero of that 1. 3 million and he was in a phase in his business where he needed lots of help.

So he had the tax knowledge, but he didn't know how to run a [00:05:30] business. So he was struggling with growth. And I had, 10 years of entrepreneurial experience, some good, some bad. And I took all those lessons and I applied them to his business. [00:05:40] And we were able to triple his business over a couple of years, which was pretty incredible.

And then so I started doing tax returns in 2011 under his guidance. And I [00:05:50] went through a very old school kind of apprenticeship rather than, taking courses in college. But it turns out I'm the better for it. So what I didn't know. At that time was that the things he [00:06:00] was doing was not the things that other people do in the tax world.

So because he came from this wall street tax planning background, they used to deal with the New York stock specialists the people who administered the [00:06:10] markets. It was always strategy. It was always, what can we do? It was always, how can we improve this specific for the client? And that can be a client making 20 grand.

It could be a client making 2 million. It's just, different strategies apply at different [00:06:20] scales for different things. So that's how I learned. And that's how I did, 50, 000 tax returns over the past, decade plus on, billions of dollars worth of [00:06:30] revenue.

And, we save clients 20, 30 million a year. And I parlayed that into tax Sherpa. Tax Sherpa. tHat I started in 2019, which really [00:06:40] got started in 2020 though it was founded for the people like me, because what happens is in the tax world, like I'm in these mastermind groups with, tax advisory services and all this kind of stuff.

And [00:06:50] the push from the coaches and the gurus and everything is always, find high earning clients, charge them more. That's basically the. And I have seen [00:07:00] people charge 150, 000 just for a tax return, and it was, this was a corporate tax return, but still it's just a tax return and it's not even to put them, not even to [00:07:10] figure out what the numbers are to go into the tax return.

It's just take the numbers you already have, put them in the form. And that's, a little bit crazy in my opinion, if the company is willing and able to pay it, then so be it. [00:07:20] So that's one end of the spectrum. The other end of the spectrum is your corner tax. Rep place, your H and R blocks or Liberty taxes, Jackson Hewitt.

And there's a bunch of them [00:07:30] and, those people are, let's call the minimally trained and I could hour after hour of stories that I've seen with people [00:07:40] bringing in old tax returns from these places, but basically they are. They're okay. If you have a very simple tax situation, if you have a W2, [00:07:50] that's it.

Then you go to them. That's okay. Even then sometimes they screw it up, but I'll try to be charitable. I'm in a good mood today. But it's the people in the [00:08:00] middle, the people that are, are self employed or have a small business or freelancers or somewhere in there. And they can't afford, [00:08:10] crazy fees for a tax return.

And if they go to the corner tax person, they just end up getting screwed because that person doesn't know how to handle. Business taxes and how to do strategy or planning or anything. [00:08:20] And those are my people. So if you also can't hold a job because you're unemployable, because you can't have people telling you what to do, , [00:08:30] then you're gonna, you're gonna fit in with tech.

She, So obviously we handle other people as well, but that's really, my core tribe, just because of my own life experience there.[00:08:40] So that's who we are and what is we do. We have a whole team, Serena is our ops manager. We've got a tax team, bookkeeping team, and we can handle, soup to nuts, but, that's what we do.

We help those people in those [00:08:50] more advanced situations figure out how to save tons of money on their taxes. This is office hours. So let's get into the questions. And [00:09:00] before we get into your questions, I have a question for you. And my question for you is what is the root problem with overpaying on your taxes?

So should take a second and think [00:09:10] about that and say, okay, let's just say you overpaid by 20, 000 this year or last year. Most people are done filing 2022s at this point. [00:09:20] So what's the real problem with that? You already paid it. Life has gone on. Okay. So here's my problem with it. It's [00:09:30] wasting 20 percent of your life.

Most people, at least the people that, that we talk to are usually paying somewhere between 20 and 40%. [00:09:40] When you factor in everything, we factor in federal income tax, payroll tax, self employment tax, additional Medicare tax state income taxes. All that stuff, it ends up somewhere in [00:09:50] that 20, 40 to 40 percent range.

And what is 20%? So a lot of times we'll come in and we'll create a blueprint for somebody. And the blueprint is [00:10:00] the method by which we apply tax strategy various kinds in order to reduce the tax liability. So the, the net result [00:10:10] is we'll say people on average between 20 Obviously numbers are dependent.

Everybody's situation is unique, but that's our bulk of what we see. [00:10:20] And so if we take your tax rate from, let's say, just take the middle, take it from 30 percent down to 20%, which is pretty common. We just saved you 20 percent of your life. [00:10:30] And so if it's, if you were paying 30 percent all in 30 percent of 365 is 109 days, [00:10:40] 109 days that you're working for the government, essentially various governments.

It could be state, could be local, could be federal. And if we take it down to [00:10:50] 10%, that saves you 74 days during the course of the year. Now, I know that's might be oversimplifying, on, on a work day, how much [00:11:00] of your time is really focused on yourself? It relatively little, if you have a job that requires going somewhere, going to an office or something, there's waking up, there's getting ready.

There's getting in the car or the train [00:11:10] or whatever you do, there's getting there. Then there's the actual work. Then there's the lunch break, which you're still pretty much at work. There's the afternoon or evening and then there's the commute home [00:11:20] and then there's the decompressing and then there's the getting ready for tomorrow.

If you're awake 16, 18 hours a day and you're spending, eight, nine hours, like [00:11:30] being paid that's not real. That's not reality because you have 12 hours all in for all the things that go into. Go into doing the job that you have. [00:11:40] And so how much quality time do you have with yourself with your family, with, whatever it is you want to do with your hobbies, work days are work days, right?

That's why they're called work days. [00:11:50] And so I've come to realize, and this is actually a recent realization for myself that what we really do beyond the money and the money's great. And I think [00:12:00] that. The money is better served in your pocket, doing whatever you want with it, reinvesting in your business, going on vacation is going to Vegas.

Whatever you want to do is better than giving it to [00:12:10] the government. I truly believe that. But on top of that, even more important is the time that you get back. And that's time that you could do anything you want,[00:12:20] cause you're able to use that time for yourself rather than being forced to work for it, for the feds.

So that's. That's my question and [00:12:30] my answer that's the critical problem with overpaying on your taxes. It is just, it's just bad for the world, basically, and bad for you in particular. [00:12:40] But I also have the answer to all tax questions. And the answer is, it depends. It depends. It depends because it does.

And, accountants and lawyers are famous for saying [00:12:50] this. And it really does depend because everything is dependent upon what's called facts and circumstances. Or you'll hear lawyers talk about a fact pattern. So it depends on what the [00:13:00] situation is, how it applies to you and your particular situation.

And my favorite example is how the if a hundred dollars gets put in your bank [00:13:10] account, how much tax do you owe on that? And the answer is it depends, was that income? Does that income have offsetting expenses? Was it a gift? Was [00:13:20] it alone? Was it randomly dropped from the sky like the COVID stimulus checks were, so it depends.

So just knowing a number does not tell you anything about. [00:13:30] What the actual impact is, because it depends on the situation. So that's the short answer to everybody's questions, but I know people want more. , so we'll get into it. And [00:13:40] I see s Serena, can you see the the chat, I don't know if you're on this or not.

Nope, I'm not seeing anything. Okay we've got arrows arrows is asking, Hey, Neil do you do [00:13:50] personal crypto taxes? I have most of my transactions and coin link, but I've recently came to the point of entering my Splinterlands transactions. And so I'm overwhelmed. Yeah, it is overwhelming. So let me give [00:14:00] you, give everybody a little bit of background on crypto taxes.

sO back in, I think it was 2013, the IRS published a a document where they [00:14:10] established their position on cryptocurrency and they said, this is property. Now I happen to agree with them that it is property. But that, that creates a whole bunch of complicated [00:14:20] scenarios that, that happened as a result.

So if you have a let's say you're on Coinbase and you buy Bitcoin and then you sell Bitcoin, it acts like [00:14:30] property. It's a capital gain or capital loss. Just if you have a stock for a bond or or if you had, if you were in the trade of. Cars. Like you bought a car and then you sold it [00:14:40] like a collector's item or something.

So that part works. Okay. And there's been no legislation or anything on this. This is just the iris stuck a flag in the sand and they said, we're doing [00:14:50] it this way. I'm like, okay, . We're more or less in agreement with that. And what none of that accounts for is more complicated [00:15:00] scenarios and situations that come about in.

In the non centralized exchange world. So in, in DeFi [00:15:10] or in GameFi. So Splinterlands is a GameFi environment where people play a game. They're rewarded with cryptocurrencies of various kinds. And the game [00:15:20] is played using non fungible tokens. So it's, it gets complicated. And then it also gets into the question of what do you actually have [00:15:30] and what do you not have?

Because some of the opinions that have come out since the 2013 paper has basically said that, you have to do a look through [00:15:40] analysis. What that means is you have to look through the tokens, especially with regard to NFTs, non fungible tokens, and you have to figure out what is [00:15:50] actually going on.

So in in splinter lands you have to actually look at what is happening. So I'm of the position, and this is a position a [00:16:00] defensible position that, staking assets by definition makes them out of your control. And in the tax world, there is [00:16:10] this concept of dominion and control where, if you have dominion and control over an asset, then you own it for, constructive purposes.

If you don't have dominion and control, [00:16:20] then you don't. And my opinion is that in many of these defy cases, you lose dominion and control when things are staked in a system. So what that means [00:16:30] is that you. And again, it depends on how you're administering your various systems and what it is that what event happens first, what event happens second, [00:16:40] but it gets complicated.

So you might have a sale, you might have a no income, you might have a recognizable income event. It all depends on what it is that you're doing. [00:16:50] So as far as how we handle crypto taxes, we'll give you advice. We're not coming through your transactions because it's just an insane number of things.

And we don't have [00:17:00] time for that. The amount we would have to charge to do that kind of thing. It's just astronomical. arRows, if you want to set up a an appointment, go to texture dot com, click the book and appointment link, and [00:17:10] that'll put you on Serena's calendar. If it's crypto specific, I'll drop in as well, just to see what's going on.

And and then we will we will figure out. What is appropriate in your [00:17:20] situation, because, maybe you have income, maybe you don't, maybe you have losses, maybe you don't it's all. Dependent, like it says on the screen. It depends. But that is the [00:17:30] difficulty of dealing with a tax, a tax concept that doesn't actually apply to the things that we're doing because you can do things with cryptocurrency that you can't do [00:17:40] with regular property.

And that creates these vague. Issues. But yeah that's the question. Number one. And Serena, what else do we have [00:17:50] on list? I know we compiled a couple before we got, we went live here. Yes. Yeah. We have a question from our, one of our clients is our tax payments, business expenses.[00:18:00]

Huh. So would it be too short to say it depends? We can, it does depend. All right. [00:18:10] So tax payments being deductible or business expense or not. So sometimes, yes, sometimes no. So what happens is that,[00:18:20] if you have let's just take the personal example first. So you let's say you work for another company, you get a W2, you make a hundred grand, very [00:18:30] clean, very simple.

The tax that you owe on that does not become a deduction to yourself. On that 100, 000, that's just an [00:18:40] additional amount that you owe, and that's just, they're just taking it off the top, essentially. And, various calculations go into that as far as how much becomes taxable and all that kind of [00:18:50] stuff that goes in our tax return.

But the tax itself is not a deduction for your personal. However if you have a state income tax. [00:19:00] That might be a deduction. It depends on the amount. It depends on if you hit the caps, the 10, 000 salt state and local tax limit imposed by the tax cuts and jobs [00:19:10] act. It depends on whether you're able to itemize other deductions or not.

And that depends on your filing status. So state and local taxes can be a deduction maybe [00:19:20] if you satisfy the various conditions on your personal taxes. On most states, if that becomes a deduction, they will then add that back to the state income. And then the [00:19:30] state level will tax you on the total, including the amount you paid to the state.

So it gets, it starts to get weird already. On the business case. [00:19:40] Now, most businesses are flow throughs. They're either schedule C's, 1065, 1120s. These are all flow through in that they, the income or the net income from the business flows through [00:19:50] into your personal tax return, and it becomes included as part of your taxable income.

In those cases, the the most common scenario we see is that. We [00:20:00] do S corporation. So 1120 s. So the company will never pay a federal tax. And so the income flows through to your [00:20:10] personal, it gets included plus or minus, whatever it is, and you'll pay your federal individual income tax on whatever that, that number is.[00:20:20]

And let me just ban somebody real quick.

Okay, there's

that. And then and then[00:20:30] so the federal tax is not. A deduction for the business there. Some states have an entity level tax. So DC has an [00:20:40] excise tax. Washington state has an excise tax. Illinois has a I forget what they call it, but it's a 2, 000 tax. And then in [00:20:50] Tennessee, they have a, they have an external tax like that.

So in those cases, just like on the personal, the state. Income tax become a deduction[00:21:00] for the federal purposes and may or may not be added back on the state level, just depending on the state and how that works out. And so those kind of [00:21:10] complications, then flow through into the personal and gets included with your personal federal tax and personal state tax.

Then just to add another layer [00:21:20] complication. So in the. In the tax cut and jobs act, which was Trump's tax reform back in 2017 they imposed this 10, 000 limit as far as state and local [00:21:30] taxes. What some states have done, and there's a handful, I think they're up to 12 or something, but some states have done is okay, so we can't get around that directly, but [00:21:40] our response to that is that we'll allow a pass through entity tax payment.

So what that does is on the state level let's say you have 100, [00:21:50] 000 of income from a New Jersey company, and that passes through to your personal. So in New Jersey, you can make a pastor election where you could say, okay, I know I'm going to [00:22:00] owe to New Jersey based on this 100, 000. And so what I'm going to do is I'm going to have the company pay New Jersey on my behalf, [00:22:10] knowing that the liability is going to flow through to me, but the company's making the payment.

And there was some some back and forth between the IRS and everything, and they ended up resolving this in [00:22:20] favor of that tax being paid by the company as a deductible expense for the company in those states where they have that. So in some states that [00:22:30] is a strategy and the and the pass through entity tax paid by the company on behalf of the shareholder is a deductible expense.[00:22:40]

So that's a case where it is a deduction other taxes, which are deductible are like payroll taxes are a deduction. At least the employer portion.[00:22:50] Sales taxes. Most people do wrong, honestly, because you're supposed to just exclude it both revenue and expense side. But if you do include it in the revenue, then you do include the the expense [00:23:00] on the expense side.

Depends on which tax depends on the situation depends on the state. And I will tell you that penalties are not going to be deductible for [00:23:10] you. If that becomes an issue then you're stuck. You have to pay tax on the income and to pay the penalty out of your, your proceeds.

[00:23:20] So sometimes yes, sometimes no is is the answer to that one. But it's it gets complicated because that's the bottom line. And just to wrap that one [00:23:30] up. So the most of the provisions of the tax cut and jobs act are ending in 2025. So into 2026, there'll be, revamped or sun setting going back to the [00:23:40] old way.

And that is a very open question as to what is Congress going to do because they can always change their mind, pass a new law. But for now, it looks [00:23:50] like that the. The pass through entity tax idea will cease to exist in in 2026.

Okay. And then we [00:24:00] have another question from a client and they heard that the Augusta strategy was thrown out in court. Neil, is this true? That is not true. That's a good thing for us. [00:24:10] So yeah, I guess it was one of our favorite strategies. So what happens is, so the plan or the guest strategy or the master strategy, it goes by a couple of different terms.

What happened was [00:24:20] there's in Augusta, Georgia, which is down the road from me, the the guys who live around the golf course and big, fancy houses, they wanted to rent out their houses [00:24:30] during the golf tournament, the masters and not pay taxes. So they lobbied Congress and that's now a thing. Under section two 80, a G you can rent your primary [00:24:40] dwelling up to 14 days a year and exclude that rental income from your taxable income.

So it's just it never happened. Just cash money in your pocket.[00:24:50] We can take advantage of this by having having management meetings with your business, that's the basics. So what happened was was that there was a court case I don't know, a year [00:25:00] ago, something like that, where somebody went to court and their version of the guest strategy got thrown out because they were just excessive about it.

They picked crazy [00:25:10] numbers and the court said, Hey, you could have gone to the, all these other places. It would have been way cheaper. So your deduction here is not valid because you did it strictly for the [00:25:20] tax benefits rather than for business purposes. So the strategy itself still perfectly valid.

You just have to follow the rules. You gotta figure out what a real price is. I don't go crazy [00:25:30] with it. It's like most things another set of things that has gotten into into into trouble areas and become red flags. People always. [00:25:40] ask about red flags here are red flags home office deductions, red flag because people abuse it.

Huge mileage deductions is a red flag because people abuse it. And I've seen [00:25:50] people bring in some crazy numbers. What are Serena's favorites? Fuel tax credits, giant red flag because people abuse them. What are some of the red flags? Let's see, home office[00:26:00] fuel credit. The excessive schedule C losses.

Those are a big one. Definitely. Yes, definitely. And conservation [00:26:10] easements are almost an automatic audit. Conservation easement is where you take a piece of property and you donate it to a conservation entity and it's set aside for non [00:26:20] development and it's basically a charitable contribution and people abuse them, crazy numbers.

And so basically every 1 of those gets audited and, [00:26:30] it's a perfectly valid thing to do, but you have to use real numbers. You have to have appraisals. You have to, look at. And what is actually going on instead of just, making up your own pie in the sky [00:26:40] kind of stuff. coNservation easements Oh, another one that's been abused and cause people to have problems is captive insurance.

So [00:26:50] captive insurance is actually a super interesting idea where you have your operating company and it has some kind of risk. So we talked to a lot of e commerce people [00:27:00] and they have giant risks. If Amazon bans them or if Google changes their algorithm, I was just talking to somebody earlier, they were doing some e commerce on Facebook.

Facebook [00:27:10] changed the algorithm and their business just. Died, just, it was doing okay. And then zero, so that's a real business risk. And that's a business risk. You cannot buy insurance for on the [00:27:20] open market. You can't go to, state farm or Geico or whatever and get a policy for that even business specialized business insurance don't ensure that kind of risk.

So what captive insurance does [00:27:30] is you basically form your own insurance company. And whether you do direct insurance or reinsurance there's. Subtleties to that, but you form your own insurance company [00:27:40] and now the operating company will pay a premium for a policy to cover that specific risk, but they can't buy anywhere else.

And so it becomes an [00:27:50] insurance expense to the operating company, but because of special rules around insurance companies, that money coming into the insurance company is not income because they are going to owe that back when a claim is [00:28:00] paid. So the insurance company takes that money. They invest it.

The investment returns are taxable to the insurance company, but that's a percentage of a percentage over the years rather than the whole amount. [00:28:10] And and so that insurance company is building up value, on, on depending on what the actuaries say, it's mathematically valid and.

thEn [00:28:20] they, hopefully someday never have to pay back, but if they do, then they cash out their investments and they pay off the the claim. You get a deduction on the operating company and you get not income [00:28:30] on the insurance company. So that's where you get the benefit. Because you are subtracting on one side and then not adding it back.

And so this is a strategy that gained in popularity [00:28:40] for a number of years. And like so many things, people abused it. And so it went on what they, what the IRS calls the dirty dozen list. Every year they publish a list of, [00:28:50] 12 strategies that they don't like. Not that they're invalid. They just don't like them because people abuse them.

So If you if you're out there and you're listening and you're thinking about doing any of these things, captive [00:29:00] insurance, conservation easements home office deductions fuel tax credits, you got to make sure that you're actually following the rules that you have your documentation that you [00:29:10] are not, picking numbers out of the thin air that are not justifiable.

And if you do that. You still might get audited, but you can win. [00:29:20] So that's the whole thing. And then, and at some point you got to make a business decision as to whether this is worth doing or not knowing the potential headaches it can bring, because, [00:29:30] when it comes to audits, the process is the punishment.

Yeah, there's the money aspect, but really the people who fight audits and have somebody who is. I'm not willing to work with them. [00:29:40] It can be extremely painful. I've had clients who were a hundred percent in the right. I'm thinking of one in particular. The question, the the real estate professional status, and this was somebody [00:29:50] who was operating Airbnb full time.

It's a job where they were spending the hours and everything. They had the log books and everything. And it was basically a 50, 000 audit. And. [00:30:00] So there was a not a husband and wife, but a boyfriend and girlfriend, it was the girlfriend that ended up getting audited and the boyfriend who was like managing their finances or [00:30:10] whatever.

His business was blowing up separate from the real estate stuff. And, we sat down and we talked about it and said, okay, you're going to have to do this, that, and the other. You're going to have to, compile your logs. You're going to have to [00:30:20] send them over. You're going to have to show the tie ins that is in the tax business or the accounting business.

We call this tick and tie where we match up different, the transactions and list them out and see, show [00:30:30] how they went into the tax return and all that kind of stuff. And and you are right, you will eventually when it will be a battle and he made [00:30:40] the decision to, the amount of time I would spend on this, I'll lose more than 50, 000 in my other business.

He just decided to pay it, even though he was right, because. He didn't want to go through the process.[00:30:50] thAt's always a decision that you have to make on a case by case basis. So many people, they hear about these lawsuits where the company's just settled, even though they know it's frivolous and they know that [00:31:00] this is nonsense, but the amount of costs that would be to actually litigate this thing is way more than if we just paid it.

And the people doing these attacks know that. [00:31:10] So that's their whole strategy. But, it's. It is what it is. So ideally, if you're doing a high risk strategy you want to back it up, from A to Z. [00:31:20] You, you may want to employ that strategy or not.

And when we talk to clients about different strategies, we will talk about, audit risks and those kinds of things. If you do this, that, and the other, you'll lower your audit risk. If you do [00:31:30] this other thing, you'll raise your audit risk. There's decisions to be made as to what you want to do, what you want, what you don't want to do.

We got a question from Mango Wombo. Do you have any advice [00:31:40] on how to make small company less dependent on its owner? I'm looking for ways to disengage from daily operations. That is a great question, Mango. So yeah I do have in, [00:31:50] in Tax Sherpa, we're going through this where, we're building out the team and, I'm still leading strategy, but I'm definitely not, doing tax returns like I was[00:32:00] part of that is just from health.

I'm not able to, but part of it is is by design as well. So yeah, the there's a number of different approaches to doing this. [00:32:10] And I think the one that's actually Easiest is you have to define exactly what it is that's happening in your business. So [00:32:20] there's general categories, right? So there's marketing, there's sales, there's there's onboarding, there's fulfillment, there's customer service, there's finance, [00:32:30] invoicing collections, accounts, payable accounts, receivable.

There's all these different things. And what you want to do is you want to have a matrix of. The [00:32:40] job on one end, and then the person responsible on the other end. And so you'll have a grid and then you just fill out where you are [00:32:50] currently. So each job is assigned to a person or maybe multiple people.

Maybe it's a team, depending on how complicated your business is and just get your [00:33:00] current state. And figure out who is doing what, as all the things that, from customer is born to, we have, we have operations, we have revenue, we have [00:33:10] expenses, all those kinds of things.

So in, in the business life cycle from birth to death of a particular stream of income. And so map all that out. And [00:33:20] then on a either monthly or quarterly basis, start moving. And figure out what are the things that are in your business that only you can do? So like with Tax [00:33:30] Sherpa I'm the Sherpa, basically how it's worked out.

I have tried avoiding that as well, but that has not worked. I'm here and this is the part, my. [00:33:40] My really extensive experience in a wide variety of areas really allows me to get insight into a lot of different things in the tax world. So that's the unique thing that [00:33:50] I have to keep doing for tax Sherpa.

When it comes to a more basic tax strategy, we're training people up internally and eventually they will take over those [00:34:00] roles. When it comes to marketing and sales and fulfillment, that's pretty much off my plate already, but it's a process, serena's nodding cause she's doing it all.

If you book a [00:34:10] call on taxshopper. com, you're going to talk to Serena and she is, she's fantastic. And she'll diagnose your issues and she'll bring it back to the team and we'll go over all the things that are going on [00:34:20] and figure out the plan. But but, so defining those roles.

And then getting the roles that you don't have to be involved in off your plate. And that can be that can be [00:34:30] accomplished in a couple of different ways. So the first question you always want to ask about a particular task or particular role is, does this need to be done at all? Can we just delete this or trash it?

And [00:34:40] it could be that you're getting in your own way with doing things a certain way. So that's the first thing to look at. Because if you can cut something, that's always going to be the easiest, most cost effective thing to [00:34:50] do. If you decide that you can't trash it and this thing has to be done, then who should do it?

And maybe that person's on your team already. Maybe they're not. But you [00:35:00] want to have a goal as far as, who should be doing what? And then, over time you have to start shifting those things over. Where people get into problem is [00:35:10] in, if they just abandon the business. So it's yeah, I hired a consultant and now I'm doing nothing.

So that does not work. [00:35:20] Anytime you shift a responsibility from one person to another, there's going to be a transition period between where you first, train that person on how to do that thing. So let's say it [00:35:30] is something simple like paying the internet bill, right?

So that comes fairly automatically if you're. If you're at one level, you just automate it [00:35:40] and you just delete that responsibility. You put it on autopay on another level maybe you have a a contract. We've got a client who has a has nurses working [00:35:50] for him and that he created this whole tablet system that they got from I think it was T Mobile or AT& T or one of those.

And. It's actually a complicated [00:36:00] process to pay the internet bill because there's 300 different devices and they have to account for the usage on all the different ones. And, there's rebates [00:36:10] involved. It's a whole thing. So that process has to be trained for somebody during the training period.

You can't just leave them on their own. You gotta train them. You gotta check them. You can say, okay, now do [00:36:20] this. And then you say, did they do that? Okay. Yes. Did they do it? Okay. Yes. And then we can move on. And over, three to six months, really, that's how long it takes for somebody to really [00:36:30] solidify a business activity.

Then you step back more and more, and eventually you just get reports. And you say, okay, were these things done? Yes. Great. Let's move on. And so [00:36:40] how many things you can take off your plate is going to depend on your business. How many people are available to do the things that you can do is going to depend on your business.

One of the [00:36:50] one of the difficulties with entrepreneur led businesses is the E myth. So if you haven't read them, there's a series of books by Michael Gerber called the E Myth. There's the E Myth [00:37:00] Revisited and the E Myth Mastery or something like that. I don't, Michael Gerber, E Myth, search it, it'll come up.

And the E Myth in his formulation is the Entrepreneur Myth. [00:37:10] And the Entrepreneur Myth is that because I'm good at doing a thing, then I can run a business doing that thing. So like in, in tax Sherpa, because I'm good at [00:37:20] tax returns means I can run a business that does tax returns. And that the one thing does not follow from the other.

I know plenty of great people, plenty of great technical [00:37:30] people who cannot operate a business at all. It's a different set of skills. But what ends up happening is because most people who go into business for themselves and who start up, a [00:37:40] a business that ends up hiring people and has a team, then they're really good at that thing.

Like I'm really good at taxes. . The people you bring on don't have your depth of experience. If they did, they [00:37:50] would've started their own companies, right? Where you as one person, as the entrepreneur leader might have been able to do, 50 different tasks.

There's not one other person [00:38:00] out there that's gonna be able to do those same 50. So you have to accept that. And then, understand people's, people's aptitudes and interests and just capabilities as far as how [00:38:10] much they can do of those different things. So hiring people gets expensive quickly.

And for most companies, payroll is the number one expense. And it's because of that function, because, when you start [00:38:20] bringing in outside help, they are just 99 percent of the time, not going to do all the different things that make up your unique skillset. And so there's [00:38:30] going to be redundancy there.

And that's going to be, part of the part of the cost, but, but you get back your time and gain the ability to scale out more. So [00:38:40] it is a trade off and those first few are by far the hardest that's where most people get stuck and you have to design your business in a way that it can afford, that overhead [00:38:50] of that, of just having those people involved and the and the training and upskilling that has to happen in order for them to take over that responsibility.[00:39:00]

I know that's general, but without knowing exactly. Going into your business that's the general strategy. There's a guy I knew through a mastermind named Scott Fritz.[00:39:10] F R I T Z he's out of I think it lives in Vegas now, but he had a, I think he still owns a a PEO where it's a professional employment organization [00:39:20] where if you're a company and you want to hire people, but you don't want to do all the HR stuff you hire, you use a PEO.

He was one of those companies and he did this to himself and he wrote a book called the. [00:39:30] Is that the four hour year or something like that where it's a takeoff of Tim Ferris's thing where he ran he did this process to, through his own [00:39:40] business and was able to reduce his workload from, a full time more than full time kind of operation to four hours a year.

And he did it by, by [00:39:50] systematically outsourcing the things that he didn't need to do. And it turns out he doesn't need to do anything in his business. He was able to replace his talent entirely which is great. And he would just come in like once a quarter [00:40:00] or something and have a meeting and that would be it.

So that's the that's the general idea, but a small company, you're always going to be, involved because [00:40:10] of just because of the size and you're not going to be able to replace all of your skills and needs in the company with other people. But how much and where that split is, it [00:40:20] depends.

It depends. It depends. Neo I have another question for you from a client. And they asked, what makes an owner's [00:40:30] straw, an owner's distribution, and an owner's salary different from one another? That is a great question. All right. I'll start off with, it depends [00:40:40] and it depends on what kind of business structure you have.

So if you're a Schedule C business, that means you are disregarded entity, either your sole proprietorship [00:40:50] or a DBA or a disregarded LLC. So if you're one of those, there is no distinction. And the business is you are the business. So any money that's in a [00:41:00] business account, that's your money. You could do whatever you want with it.

There's no concept of distributions or basis or anything like this. Once your business graduates to a higher level as [00:41:10] either as a partnership or as an S corporation, then we get into where these things start to matter. A company makes money. And let's just say it's a, [00:41:20] it's an S corporation.

Company makes money, it spends money, has expenses. And then at the end of that process, it has a net income or net loss. So let's just say net income for simplicity.[00:41:30] Just to put numbers to an example, let's say S corporation has 50, 000 net income after expenses. So that 50, 000 flows [00:41:40] through onto the owner's tax returns.

It could be one owner. It could be many owners. Whatever their fractional percentage is, that is what flows through onto their tax returns. Now, [00:41:50] If there's an associated 50, 000 there, then the, that 50, 000 can be distributed to the owners, based on their ownership share. [00:42:00] And that's a distribution.

So an escort distributing profit is a non taxable event. It gets into weirdness when the amount distributed. [00:42:10] Is not is greater than the amount of profit and investment that the owner has. So this can get into real estate. [00:42:20] So if you're in a syndication, let's say, and there's, a hundred owners and everybody puts in 10 grand.

And then the property [00:42:30] is bought, it's improved, it's rented, and then later on, it's refinanced. And over the couple of years, it has gone up in value. So now everybody so they take [00:42:40] the refinance money and they distribute a bunch of funds to the owners. So we put in 10, a couple of years later, we get back 15.

Okay. Now, the first 10 is a distribution [00:42:50] against my basis. So that's the investment that the owner made. And so that part is tax free. The 5, 000 extra is what's called excess distribution.[00:43:00] And that actually acts like a capital gain. So it's going to be, taxed at longterm capital gains rates.

So that, that's one item an owner's salary. So [00:43:10] S corporations. When profits flow through into the owner's tax return, it avoids self employment tax. So partnerships carry [00:43:20] self employment tax, S corporations don't. And so that's why there's a reasonable compensation rule on S corporations, but not on partnerships.

And so what, because the S corporation [00:43:30] profit allows you to avoid having to pay social security tax and Medicare tax and unemployment tax. They implemented this rule called the reasonable compensation [00:43:40] rule. So the owner's comp is the compensation that the company pays to the owner for the services [00:43:50] provided by the owner.

Now this gets fuzzy real fast. But basically it pays a wage. So a W2 is issued and payroll taxes are applied and [00:44:00] the. If you look at the court history, the reasonable compensation things that go through court are usually, like everything else. They're excessive kind of things.

They're like, Oh,[00:44:10] company made 200, 000. I paid myself 24, 000. That's reasonable. It's is it, and really it hinges around social security tax because the income tax remains the same [00:44:20] more or less but social security tax is the biggest chunk of that self employment tax.

It's 12. 9 out of the 15. 3. So when these things go through court cases, the IRS always [00:44:30] comes back and says you should have paid yourself. They pick a number and it's always like right near the maximum for social security. beCause every year they raise the cap. That's actually going to be one of the next [00:44:40] great tax hikes is social security tax.

But but. So because you're allowed to avoid that with S corporation profits, that [00:44:50] they counteract that with the reasonable compensation rule and. Just as a quick aside, the reasonable compensation, like what makes it reasonable? Basically, you want to tally [00:45:00] up what it is that you actually do on a day to day basis.

So if you're like mango and you totally outsource yourself and you're not actually doing anything for the business, then there is no [00:45:10] reasonable compensation. You're just an owner, right? But if you're like most small business people, then you're going to have owner shares, owner, profit.

Portions and you're going to have [00:45:20] how much work did I actually do for the business? Was I out there marketing? Was I doing sales? Was I doing fulfillment? Was I doing, this, that, and the other. And, you figure out in your market for a business of your [00:45:30] type. And there are reports you can get to calculate all these kinds of things.

And I spent three hours doing this and two hours doing that and five hours doing this other thing and 12 hours doing the third, the fourth [00:45:40] thing. And you figure out what a blended average would be to actually hire out those jobs and you pay yourself that and that, that's a that's a, an approach that has been [00:45:50] tested and succeeded in court as far as defining what is reasonable.

So that's the reasonable comp or owner's comp portion. And then what was the third one, Serena? I think you had three terms. [00:46:00] Yeah it was the owner's draw, owner's distribution and then the owner's salary. Okay, owner's draw. So owner's draw is more or less the same term as a distribution.[00:46:10]

thEre can be instances in partnerships where you have a a guaranteed payment. Sometimes people call that an owner's draw. So a guaranteed payment is [00:46:20] just a replacement for salary. It, it carries the same payroll tax kind of implications and it's basically just a flat rate that the partnership is going to pay towards [00:46:30] 1 or more of the owners.

And sometimes they'll book that as a draw. But otherwise, yeah, it's just the same as a distribution. Okay. And [00:46:40] then I know we only have about six minutes left. But another question I have for you, Neil, is I thought we were going to close early today, but apparently not. Yeah. No. It's [00:46:50] almost December 31st.

And what I've been hearing from clients is if, is there enough time to create strategies or to be proactive because you only have a [00:47:00] few days left in December. Yeah, that's a great question. So the short answer sides, it depends is yes. So [00:47:10] there, there is time to do a lot of things, not everything.

So there have been strategies we've had to, say next year we can do this, but we don't have time to get these things implemented. But there's a [00:47:20] lot of strategies you can still do. So don't let the calendar dictate your aversion to planning for the end of the year. So I know we're in [00:47:30] constant communication with a bunch of clients right now.

We're trying to tie up loose ends and we're trying to, put some things into place for other clients. Yeah it's still a very active time to be doing all your tax [00:47:40] strategy. And but yeah, there, there are a few things that are just out of time to do. So there's that.

So we got five minutes left. I'm going to cut off the [00:47:50] questions here. And cause I did want to go over just a couple of things, a couple of next steps. Here's what we want you to do. We've got a free [00:48:00] LinkedIn group that we're starting. It's called tactical advice, explore T A X. That was my clever invention.

And this is where we're so like the [00:48:10] recording of this, the slide deck, everything that'll be posted in the LinkedIn group. You just go to texture, but. com slash group. That'll redirect you to LinkedIn. You can join there. And every week we do [00:48:20] one of these now next week we're off because, break between Christmas and New Year's.

And so there won't be one this upcoming week, but every other Tuesday [00:48:30] you just go to taxsherpa. com that slash live and I'll update the, that redirect to always go to the next event. And And those are the two things that we want you to do. [00:48:40] And if you have more questions, you post them in the tax group, tactical advice explored, and small business mastery is the subtitle and, we'll talk about it there.

[00:48:50] And those are, there's going to be for, general questions. So mangoes question about Getting to be less dependent on the owner. That's a perfect question for the tax group where we can [00:49:00] share ideas and go over all those different things. I can give you links to all the things I talked about with the E-Myth and the and Scott Fritz's book.

I have a copy on a USB drive somewhere, but [00:49:10] they gave it to me at a conference. But yeah, so that's what we wanna see you doing next. And otherwise, we'll see you over the next. Oh, there's [00:49:20] our little header thing. We'll see it on the next one, which is going to be two weeks from now, which is the second, I think, is that right?

Yeah. [00:49:30] So January 2nd will be the next live event. And I don't know if we'll do a, so normally we alternate, we do one office hours and then one like a [00:49:40] strategic level presentation. And, so normally next week would be the strategic level, but I don't know if we should push that out or just go back to office hours and keep our regular schedule.[00:49:50]

I'm sorry. What do you think? I think we should do Q and a when we come back. Okay. That works for me. All right. So January 2nd will be office [00:50:00] hours again, and, bring all your questions and we'll see you next time.

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Neal McSpadden

Neal went from owing the IRS over $1,300,000 to Zero and in so doing discovered the world of tax planning. Since 2011 he's helped tens of thousands of clients save hundreds of millions of dollars on overpaid income taxes.

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