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What You'll Learn In Today's Episode
  • The real details on what it takes to put your kids on the payroll
  • A helpful framework for talking to your clients about business expenses and what might be deductible
  • The critical pieces you will need to document to stay on the IRS's good side.


This week Steven is joined by Mike Jesowshek, host of the Small Business Tax Savings Podcast and it’s one you won’t want to miss. The internet is full of headlines on tax planning topics but far too often those headlines are not accompanied by the information you need to actually get things done. Of course we are all about implementation and taking action so Steven and Mike get into the details of what it actually takes to get the tax benefits of putting your own kids on the payroll. They also discuss a broader framework you can use as you talk to your clients about how to think about the expenses they put through their business.

Ideas Worth Sharing:

Get some more of the dirt underneath it to understand- what actually needs to be done to implement this in my business. - Mike Jesowshek Click To Tweet You can't just assume that it's going to be worth the trouble of register or trademarking your business name just to try to throw your personal expenses in there. - Steven Jarvis Click To Tweet There's a lot of, I think opportunities and lessons outside over and above just the tax savings around this idea of hiring your kids. - Mike Jesowshek Click To Tweet

About Retirement Tax Services:

Steven and his guests share more tax-planning insights in today’s Retirement Tax Services Podcast. Feedback, unusual tax-planning stories, and suggestions for future guests can be sent to

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Read The Transcript Below:

Steven (00:50):

Hello everyone, and welcome to the next episode of the Retirement Tax Podcast. I am your host, Steven Jarvis, CPA, and in this show I teach financial advisors how to deliver massive value to their clients through tax planning. And today I have a special guest who’s not only going to share some insight on how you can work with your clients, but also probably some things that might apply to you as the advisor as a business owner. So joining me today is Mike Jesowshek, who is the host of the Small Business Tax Savings Podcast and actually a returning guest. Mike was a guest early on in the Retirement Tax Services podcast. So Mike, welcome back.

Mike (01:25):

Yeah, Steven, thanks for having me again.

Steven (01:27):

Yeah, of course. Always excited to see other people who spend so much time and energy sharing great information around tax planning. And one of the reasons I’m excited to have you on is that while I spend a lot of my time more focused on what individuals can do as is in the name of your podcast, the Small Business Tax Savings podcast. I mean, your whole emphasis is really around working with small business owners.

Mike (01:49):

Yeah, exactly. I’ve been, I started Entrepreneur Journey when I was pretty young and I started at the age of 14, got into online marketing industry, so never intended to be an accountant by any means, but kind of made waves throughout the online marketing industry. Went to college. My backup plan was, Hey, I’m going to get my accounting degree as a backup plan in case this whole marketing thing doesn’t work out. And here I am today talking about taxes. But that was what sparked me initially to get into the small business realm because that’s what I was in, that’s what I was always working in. And so I got faced with a lot of tax bills early on before I got even started getting into this part of the space. And I did a lot of research, did a lot of things myself that got me to get that initial idea of, oh, there’s opportunities out there that so many business owners are missing out on. So many business owners don’t even know is out there for them. And that was really my passion is to bring that awareness to every small business owner out there.

Steven (02:49):

I love you providing that context. I think any business owner is just as committed as you are to saving taxes, but probably not as committed as you were and as you currently are to doing the research to figuring out how that all works, which is why I love being able to talk about it on a podcast like this. Now, before we just dive into a laundry list of potential tax strategies, it seems like online that’s quite often what you find is just this kind of menu of just, Hey, take your pick. Just whatever sounds nice. Just go ahead and do that. And there are definitely a lot of different potential strategies. But before we go down that rabbit hole, how do you just kind of frame this from just a higher level of how should business owners be thinking about their tax situation more generally before they get into specific strategies?

Mike (03:28):

Yeah, I think the first idea is, and we talk about this all the time, is that, and I’m guilty of this and other areas in my life, is that we spend so much time learning. We’re listening to podcasts, we’re reading books, we’re doing a ton of learning, but then we never take that next step and actually apply it so someone can listen to your podcast, someone can listen to my podcast and have this great knowledge on different tax strategies, but it’s that implementation piece that is key. So I always say the first thing that we want people to realize is the difference between taxes and tax planning. Because when most people hear the word tax, they’re thinking, okay, I meet with my accountant in February, March, April, sometime in that timeframe, give ’em my documents, they file it, and then that’s the last I want to hear about the word tax until next year.


And we’re saying, no, no. That’s completely opposite thinking tax planning is a completely different season than tax prep and filing. And so tax planning are things that we’re learning implementing throughout the year before 12/31, and then once 12/31 hits, now we go into that tax filing season. So I think it’s important for business owners to understand that aspect. And then when I go down that route, I also say, Hey, most people think that tax savings are just for the rich, just for the wealthy. And when we look at the stuff that we’re teaching our podcast, I always say, for the most part, most of the strategies we’re talking about can be applied. Whether you’re making a thousand dollars a year on a side hustle or you’re making a million dollars a year on a successful business, most of these strategies can be applied across the board. And so that’s the other piece that we kind of want to do a mind shift to say, Hey, these strategies are not just for the rich, not just for the wealthy, the same strategies that they’re using you can use as well. And now obviously there’s different strategies for those that are higher income earners and things that we can go down a different route with that, but it doesn’t mean that what we call our core tax strategies aren’t available to business owners regardless of their size. 

Steven (05:19):

I appreciate you making that point because since my focus is more on the individual side, quite often I’m more often dealing with just the, Hey, I’ve got a side hustle as opposed to the full-fledged business. And that’s one of those things I have to overcome with a lot of people is this idea that, oh, well, if my business ever gets to a certain size or if it ever gets more complicated, then I’ll worry about tax planning. So now, I mean, to your point, Mike, that’s exactly backwards. The level of income shouldn’t dictate whether we’re looking at potential strategies. It certainly will impact to what level we can take advantage of them, but especially with somebody with a side hustle with only a few thousand dollars of income, then actually my mindset’s a little bit different because if you’ve only got a few thousand dollars of income, I’m probably looking to see how do we offset all of that revenue? Whereas if you’re to the point where you’ve got a million dollars in sales, I probably can’t help you offset all of that, but there’s still strategies there, but we can’t just wait for this fictitious someday of, oh, I’ll eventually get to that.

Mike (06:14):

Exactly right. And we see that so often is that, and I always say, if you are an individual, what is one way that you can save on taxes? I say start a business, buy a rental property. Those are two strategies right away that you can save on taxes. And it’s this idea of you’re generating income, but there’s potential that there may be no tax. You don’t have to pay taxes on that income. And so when we look at what we call our core tax strategies, it all starts with this idea of after-tax and pre-tax dollars. And so when we look at after-tax dollars, I like to give an example of a W2 earn versus a business owner. And so I always say, think about when COVID started and maybe you were working in an office, now you’re sent home and you have to go out and buy a desk.


You’re working from home, you got internet, you have utilities that you’re using at home, you have to buy a chair for your home office. And as a W2 worker, none of that’s deductible. You don’t get a tax deduction for any of those items. You’re just paying out of pocket. So you get your paycheck, you get taxes taken out, and then whatever’s left over is your after tax dollars. And any spending that you do with that money is considered after tax spending. But when we flip that switch and look at it from a business owner, you have your sales or your revenue from your business, and then you have all these expenses that you put into it, and then whatever’s left over is what you’re taxed on. So any of those expenses that we can get into the business are what we call pre-tax spending.


It’s items that you’re getting a deduction from prior to your money getting taxed. And so as a business owner, we always say, how can we shift more of our after-tax spending into pre-tax spending? And so as an example, that home office that we’re using, that chair that we bought, that desk that we bought now as a business owner, those are all tax deductions. Instead of using after-tax spending as we would as a W2 employee, we’re now doing pre-tax spending on those deductions. And so many accountants, so many people out there hear from their accountants and they’ll say, Hey, you have a good income year. Your business is doing good this year. Maybe you should go out and buy a piece of equipment, or we’ll go buy a new truck before the end of the year so we can get some big expenses on the books.


And we say, well, of course if you need a new truck or if you need a new piece of equipment go out and it makes sense business wise to do it, make those purchases, yes, there are tax advantages to that, but from a standpoint of spending money just to save on taxes, the ratio of what you’re saving just doesn’t make sense. So we say, let’s flip that switch slightly and say, how can we, instead of just going out and buying something that we don’t need, how can we take spending that you’re already doing in your day-to-day life, find a business purpose for it and move it from after tax spending into pre-tax spending to help offset that income in your business.

Steven (08:54):

Mike, I really like how you’re presenting that framework. And for advisors listening, this is really helpful for how you explain these concepts to your clients as well because you’re taking this beyond what I typically see on social media and on the internet because there’s plenty of people who will tell you, Hey, you should go start a business so you can save all this money in taxes. The one that drives me nuts is when I have taxpayers who say, well, should I create an LLC? So that’s tax deductible. It’s just like, no, who started that and where can I find them? But I like that you’re taking it further than that and you reinforce it there at the end that we’ve got to make good decisions and then figure out a tax efficient way to do that. Going and buying that Gwagon, just so you can save on taxes, doesn’t actually put you ahead unless that’s what you were already planning to do.


Same with starting a business. If there’s something you’ve been excited about that you want to go out and do, by all means start a business. Let’s talk about how to get tax deductions in there, how to get more into that pre-tax spending. But you can’t just assume that it’s going to be worth the trouble of register or trademarking your business name just to try to throw your personal expenses in there. There’s got to be, you mentioned in there, there’s got to be a business purpose for this, but quite often there’s more that we can do if we’re proactive and intentional.

Mike (10:06):

Oh yeah. I mean, so true. And I always can’t give an example. Let’s just imagine that for easy math, you’re in the 25% tax bracket and you go out and buy a hundred thousand dollars vehicle for your business. Sure, you buy a hundred thousand dollars vehicle, you just saved roughly over time $25,000 in taxes, but you just spent a hundred thousand dollars. And so sure, if you needed that a hundred thousand dollars vehicle, you got it at a discount, you paid 75,000 for it instead of a hundred thousand for it. But ultimately, if you only needed a $50,000 vehicle, now you just spent a hundred thousand or you spent $75,000 for a vehicle that you only need to spend $50,000 for. And so it’s that kind of shifted mindset that so many small business owners get stuck in a trap buying things, spending on things that they don’t really need just because their tax advisors saying, go do this because they’ll save on taxes. And they’re right. They do save on taxes, but is it the best way to save on taxes? I don’t believe so. I think there’s so many other ways that we can shift after tax spending to pre-tax spending in a much more efficient and a much easier way to help save on taxes while still growing wealth.

Steven (11:10):

So again, for the advisors listening, you can’t take for granted that your clients understand these concepts. These are things that are worth revisiting before you dive into the really exciting sounding and glamorous tax strategies that make for TikTok videos, make sure that your clients are doing the basics and then move on. But Mike, I know that this is a great framework for where this starts, but I know that you go a lot further than this as you work with clients, as you kind of build that foundation of, okay, I mean, the starting point is, Hey, should we really be buying that truck or not? Can we deduct that chair desk if we’re a business as opposed to a W2 employee? What are some other things that you’re doing with business owners that help them get more into that pre-tax bucket?

Mike (11:51):

Yeah, one of my favorite strategies, especially for those with kids, is bringing your kids into your business. So it’s this idea of hiring your kids and this strategy, the idea behind it is one, how can we start introducing our kids to this idea of working for money? So how do they put work in, get paid for it? The second one is how can we maybe if our kids might be taking this business over at some point, or we at least want them to make that decision of, is this something that they want to do with they can get involved in that business at a young age and really kind of get their feet wet in whatever your business might be. So when we look at hiring our kids, and then there’s obviously the tax savings piece to it, and so generally stating, depending on how your business structure is set up, but the idea behind it is there’s a potential that you could pay your kids out of your business and they pay no income taxes on that.


There’s no social security withholding, there’s no Medicare withholding, there’s no federal unemployment. It’s just we write a check from our business to our kids, we get a business deductions and our kids pay no income taxes on that income. And now obviously there’s stipulations. Okay, how does that work? How much do we have to pay them? What type of entity structure do I have to have set up? But this is a strategy that you are essentially shifting income from. You’re not worrying about the kitty tax or anything like that, but you’re shifting income from your bracket to your kids’ bracket. And not only above that is that once that money’s in your kids’ bracket, now they have earned income. Now they could fund a Roth IRA if they want to. And so we have clients that they have a 10 year old that we’re funding a Roth IRA for.


And think of the power behind hiring your kids for six, seven years in your business while also funding a Roth IRA that’s going to be growing tax-free for their entire life. Or hey, if they get to college and now they get to a point where they say, I need some money and there’s no other resource out there, well, they can pull from that Roth IRA, at least the principal piece that we put in there and use it for whatever funding they might need. So there’s a lot of, I think opportunities and lessons outside over and above just the tax savings around this idea of hiring your kids. I always say, you’re going to support your kids either way, right? You’re going to send them to basketball camps, you’re going to send them to amusement parks with their friends, and you’re typically just going to say you’re going to use after-tax spending for that.


But how can we shift that spending into pre-tax? How can we still support our kids, but also now get a tax deduction for it, have them potentially pay no income taxes for it, teach them the business, teach ’em this idea of earning money and hiring them in our business. Now, there’s some things that we need to be careful with. There’s some things we need to document. They need to be doing real work. They need to be getting paid a reasonable rate for the work that they’re doing. They need to be a certain age where it makes sense. So there’s definitely some dot our I’s and crossing our T’s that we need to do, but the potential there is really large. Now, what I hear from a lot of people and they say, that’s sounds great, but I’m an attorney. What are my kids going to do in a law firm?


And I always say, this is the opportunity for us to get a little creative. I’ve never found a business that I could not find something that their child could do in their business. And so in that attorney example, we had a conversation a couple months back. Attorney said, Mike, I’m a solo law firm. There’s nothing my child can do in that. I said, well, do you guys do any social media marketing? Do you guys do any direct mail? Could they be stuffing envelopes? Could they be cleaning out the office? Could they be shredding paper? Is there things that they can be doing in that realm? And the attorney came back and said, well, I’m referral based only. I don’t even have social media accounts, so there’s no purpose for them to help in that area. I said, well, that’s funny because what you just told me there gave me a great idea for your kids.


You said you had no social media accounts. I know you’re a referral only, but would it hurt to have a social media account? Would it hurt to upkeep a social media account that maybe your 15 year old can post things on, post articles on post images on? And not only are you potentially maybe getting an extra business from that or maybe getting your business in front of your current client’s eyes in an area that they maybe hang out, but now we’re also taking advantage of this tax advantage. And so it’s this idea of we want to look at what does the tax law allow us to do, and then how can we get creative and make that make sense for us? And sure, it takes some effort, it takes a little work for us to find that reasoning behind it, but ultimately, the work to do most of these tax strategies is not that much for the tax benefit that we can get from it.

Steven (16:13):

So Mike, let’s keep talking about this. The hiring your kids one, because this one does come up a lot similar to starting a business. I think this is one that’s easy for people to kind of throw headlines out about, but then I see a gap, you mentioned it before, that the implementation is what counts. The knowledge that you and I can share with people is interesting, but it’s the implementation that counts. So advisors listening to this, they’re like, Hey, I’ve got a 12 year old at home. I’ve heard this a dozen times before. I’ve never done anything with it because, and maybe you’ve already addressed what some of their concerns might have been, but as you work with a business owner, what’s that next step? I’ve got a business, I’ve got a kid logistically, what do I do now?

Mike (16:50):

Yeah, so the first thing I look at is let’s look at your entity structure. How are you set up? Because that’s going to determine is this income really taxable? How do we treat this income and what does that look like? So depending on where your business is, you may be set up as an S corporation. We could obviously talk for days about how an S corporation may make sense for some businesses. But if you’re set up as an SS corporation or a C corporation and you hire your kids within that business, you have to pay, you have to withhold for social security tax and Medicare tax and federal unemployment on that income for them, and then maybe whatever kind of state taxes that you might have as well. So if you hire them in an S corp or a C corp, their income would still be tax free up to the standard deduction.


So 12, $13,000 a year, they would pay no federal income tax on it, but you as the employer and them as the employee, would still have to pay their share of social security, Medicare, federal unemployment. If you’re set up as a sole proprietorship or a single member LLC, and they’re a direct dependent of yours, now payments to them because they’re a direct dependent of yours and you’re disregarded entity, you do not need to withhold for Social Security and Medicare. You do not need to withhold for federal unemployment. So the first thing, when they’d come to me, I’d say, okay, let’s look at your entity structure. Are you set up as an S corporation? Okay, now we might want to start a family management company. We might want to start a single member LLC or a sole proprietorship that does services for your SS corporation and that family management company.


And I’d say that in air quotes because we might not actually call it that, but it would be a company that provides services for our S-corps, but now we can hire our kids out of there to avoid that idea of social security, Medicare taxes. So that’s the first place we go. And then once we get, okay, we understand what route we’re going on that line, now it’s like, okay, let’s find out what we want to do with our children. What kind of job are they going to do? I recommend setting up a job description, say, here’s what our child’s going to do, have a job description on file. And again, everything we’re talking about here is just stuff that we have on file. We’re not submitting this job description to the IRS. We’re not doing any of that, but we’re putting it on file.


So if the IRS ever comes knocking, we just send them our file and we’re good to go. There’s nothing to argue with. We have the documentation already. So set up a job description. What is your child going to be doing for your business? Sit down with your child, look through your business. What can they be doing? Set up an employment agreement. We’re actually hiring our kids in this business. Once we have those set up, then we can get the child working. What is an hourly rate for them? And I always say that hourly rate has to be reasonable. If they’re going to be cutting lawn at your office, we can’t be paying them $200 an hour, unless $200 an hour for whatever reason in your area is a reasonable rate for long cutting service. But we have to be paying them a reasonable rate while also taking into consideration their age and experience.


So obviously our child, we’re going to pay less than we would pay a professional lawn service because they’re in that business. So we need to find out what is that hourly rate that we’re paying them. Then start a time sheet, what are they doing? What’s the date, how many hours they’re putting in? What did they do that day? And start having a time sheet that records those payments that we’re eventually going to make to them. And then it’s just as simple as processing the payment from the business account to the child’s account. If you’re paying them through an S corporation or C corporation, you got to obviously go through the whole payroll process. If you’re paying them out of a sole proprietorship, single member LLC, it’s just taking that check, sending it from the business account to your child’s personal account. A couple key things we want to make sure we’re doing is we can’t be having our child then pay us rent to live in our house or having our child then taking that money and going buying groceries for our family.


So we still need to maintain those regular parental activities. But going to a basketball camp doing those types of things, that’s not a normal parental activity. So that would be fine with them using those funds for that. Or again, as we kind of talked about, now they have earned income. Let’s fund a Roth IRA. That’s one of my favorite things to do with small business owners and hiring their kids. So that’s the process or wave that we would go down is you have a few documents on file that we’re keeping and making sure that we dot the I’s cross our T’s, have support to back this up in the event of an IRS audit. And then having understanding what is our entry structure to make sure that we’re doing it in the most tax advantage way to save the most in taxes.

Steven (21:01):

I appreciate you going into the details there, Mike. I know a lot of people have questions around that, and that provides such a better framework for, okay, here’s how we actually get this done. Because too often tax planning strategies are left at the headline of, Hey, you should hire your kids. And then people either go and they do it wrong. They skip all the documentation, they don’t understand the legal structure, they don’t look at the employment laws in their state. They skip all these important details that can get you in a lot of trouble, which to your point before these aren’t so cumbersome that you can’t overcome them and that it makes it not worth it. You just need to know what you’re getting into. Mike, on the flip side of this, are there any things that you look for when it comes to hiring kids that you say, Hey, if these things exist, then it probably isn’t a good idea?

Mike (21:45):

No, and I would just go back to your point there is that there’s a lot of noise out there on social media, and so most of that noise is good noise, is true noise. Most of those headlines that you see, those TikTok videos that you see, most of the time it’s true information. What’s missing is those core details like, okay, now how do I actually do it? And I think that that’s so key is that when you see something on TikTok, you see something that sounds so attractive and something that would be relevant and make sense to you, take that and continue the research on it because it’s just a little bit more legwork that you need to do. Watching a minute clip about hiring your kids is going to give you, Hey, that’s a potential, that’s an idea, but that’s not something that we just go and implement off of a minute long video.


So just a little bit of legwork that you need to go there to do that. As far as hiring your kids, I would say tax hall, one thing that supports is seven and under or seven and over, I should say. So if you have a child that’s seven and under, I would say walk that line a little bit more carefully. There’s no tax law that necessarily denies it. It’s just tax law has approved seven and over. There’s cases that support that. So we have clients that their kids under seven do do some work in their business, but again, let’s make sure that it’s reasonable. What are they doing for you? A child that’s three years old, making $12,000 a year probably doesn’t make sense. I don’t know many jobs where that would make sense, but a child that’s three years old, four years old, making a thousand dollars a year because they’re doing a little things here and there, sure, that could be potential, but I usually try to say, Hey, let’s do seven and older is a safe route to go down.


And then again, looking at entity structure. Even if you’re set up as an S corporation and hiring your kids in an S corporation, we have clients that do that. You’re paying Social Security and Medicare, but you’re still saving taxes. So if you pay your child $10,000 a year through an S corporation, sure you’re paying say roughly $1,500 in additional taxes than if you would’ve paid them out of sole proprietorship, but you also still have that $10,000 as tax-free income to them. So there’s a little bit of cost for it, but you don’t have to jump through the hoop of a family management company as we kind of mentioned earlier.

Steven (23:52):

Yeah, I mean, again, Mike, I really appreciate you taking the time to walk through all of that. I’m racking my brain for other details I want to fill in there, but I think you really hit it all. If for people listening, if you were one of those people who had heard of this, but you were hesitant to move forward, there’s your step-by-step process. There’s the things you need to be considering, the things you need to be documenting, the conversations you need to be having, the questions you need to be asking so that you can go and turn what used to just be a nice idea on a podcast into a reality in your business.

Mike (24:19):

And one thing that I always say is how we started our podcast and how I started this idea and focus on content creation is that I was in a position before I even got into tax. I was just doing bookkeeping for small business owners, but I was working with tax professionals. And every time I’d ask them a question about tax-related items, I’d always get that “It depends” answer. And that really frustrated me because I was like, I know it depends, and I know every business and everybody’s situation is going to be different, but for majority of the strategies, at least 90 to 95% of the strategy, it doesn’t depend. It’s the same for every business. And then we’re tweaking it a little bit from there. And so that’s really what pushed me to start doing my own research and eventually getting into this realm of tax planning.


And so my goal with our podcast and all the free content that we put out is to get business owners to that 90%. Let’s get you to there. Let’s talk to you about hiring your kids and not just say, well, you can hire your kids and be over with it. Let’s go into a little bit more details, but get you far enough that you can nearly implement this strategy. And then you just have to tweak it a little bit for your specific scenario. So this idea of hiring your kids, we’re going to talk about the benefits of it, what you need to worry about, what documents you want to have on file, and then if you’re an S corporation, okay, now you might have to tweak it a little bit from someone that’s not an S corporation or if you have a seven year old versus a 15 year old.


We’re going to tweak the strategy slightly for those little instances. But my goal is to get clients so far enough into that strategy that they can start running with it. And so that’s the thing I would just say is just continue that research. If you find something that looks sexy, something that sounds great, there’s a chance that it could be true, and likely oftentimes is true. It might not be as sexy as it sounds in a one minute video, but it’s definitely possible for you to implement. And so it’s just taking that time to research a little bit, get more details, get some more of the dirt underneath it to understand, okay, what actually needs to be done to implement this in my business?

Steven (26:12):

Yeah, that makes a ton of sense. And again, for anyone listening who wants to learn more, especially about business related tax planning strategies, Mike hosts the Small Business Tax Savings podcast. So definitely check it out, subscribe to it. Everyone tells me that most podcast listeners listen to at least seven podcasts. So this is, go listen to his podcast. In addition to the Retirement Tax Services podcast, you’re going to get great information from both. And Mike, you hit it just right on the head of really action is what counts. It’s implementation over knowledge. And so that’s what we’re all about. You’ve been hitting on action items as we go along. So if you have interest in small business, make sure you subscribe to Mike’s podcasts. Make sure that you continue. I like that what you said of continue the research. If you hear something that sounds interesting, that sounds like it might be applicable, make sure you take that extra step to learn a little bit more, to get to that 90% to potentially work with a professional who can help you execute it. But I love that implementation is what counts more than knowledge. Well, Mike, thanks for being here. I really appreciate your time. It’s been a great conversation. 

Mike (27:13):

Yeah, Steven, thanks for having me. 

Steven (27:15):

And to everyone listening, until next time, good luck out there. And remember to tip your server, not the IRS.


The information on this site is for education only and should not be considered tax advice. Retirement Tax Services is not affiliated with Shilanski & Associates, Jarvis Financial Services or any other financial services firms.

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