The Chris Voss Show - The Chris Voss Show Podcast – Maximize Your Business Tax Savings with Expert Tips from Douglas Carpenter

Episode Date: November 9, 2025

Maximize Your Business Tax Savings with Expert Tips from Douglas Carpenter Books4hospitality.com About the Guest(s): Douglas Carpenter is a seasoned financial expert with over 40 years of experience in the industry. As a Certified Public Accountant (CPA) and Chartered Financial Analyst (CFA), Douglas started his career as the youngest registered stockbroker in America at the age of 17. He has worked at a top four accounting firm and held various consulting and chief financial officer roles. Currently, Douglas owns and operates Comprehensive Accounting Solutions, providing a full spectrum of accounting services, particularly for small businesses and the hospitality sector. Episode Summary: In this engaging episode of The Chris Voss Show, Chris talks with Douglas Carpenter, a renowned CPA and CFA, about smart financial strategies for businesses as the year-end approaches. Douglas shares his extensive knowledge on tax-saving tactics, business accounting, and financial planning, aiming to help business owners maximize their tax returns and keep more money in their pockets. As tax season looms on the horizon, Douglas's expert advice is especially pertinent. Throughout the conversation, Douglas delves into various strategies for minimizing tax liabilities, discussing everything from different business structures like S Corps and C Corps to the importance of understanding cash flow and business accounting. He offers insights into how businesses can leverage opportunities for tax deductions, highlighting the need for strategic financial planning throughout the year. The importance of having a knowledgeable tax advisor is also emphasized, with Douglas warning against the risks of poorly managed finances and tax filings. Key Takeaways: End-of-Year Tax Strategies: Business owners should focus on maximizing their tax efficiency before the end of the year, utilizing strategies such as HSA contributions, equipment purchases, and appropriate salary distributions. Business Structure Insights: Choosing the right business structure (e.g., S Corp, C Corp) is crucial for tax efficiency and should align with your overall financial strategy. Professional Financial Advice: Engage a qualified CPA for expert financial advice and ensure you are not overpaying on taxes. Relying on professional help can unveil potential savings. Importance of Documentation: Meticulous record-keeping and proper documentation of business expenses are essential and can lead to significant savings if managed correctly. Cash Flow Management: Douglas highlights the critical nature of cash flow management for businesses, asserting that understanding and predicting cash flow are crucial for sustaining and growing a business. Notable Quotes: "Billionaires do pay taxes. They don't overpay taxes. You shouldn't overpay your taxes either." "What are you going to do different next quarter that you didn't do this quarter?" "Fulfill your obligations, but don’t pay more than you absolutely have to. There's a lot more that people leave on the table than they realize." "Don't cheat on your taxes. It’s not worth the risk when you can save in legal ways." "Cash flow is the lifeline of any business. Knowing where your business stands today and where it's headed is crucial."

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Because you're about to go on a moment. Monster Education Roller Coaster with your brain. Now, here's your host, Chris Voss. Hi, Moses, Voss here from thecrisVos Show.com. Well, you're doing with our least things that makes it official. Welcome to over 16 years, 2,500 episodes of the Chris Voss. About to turn over to 2,600. And we're putting out just 48 new shows a month with some of the most amazing minds and authors

and all that good stuff. Be sure to refer the show to your family, friends, and relatives. We appreciate your support. Go to goodreads.com, Fortress Christchast Christfoss, Facebook, or I'm sorry, yeah, Facebook.com, Fortressch, Chris Foss, YouTube.com, Fortress, Sch, Chris Foss. And there's some other places out there. I don't remember what it is, but you know what it is because you heard this a million times before. Opinions expressed by guests on the podcast are solely their own and do not necessarily

reflect the opinions of the host or the Chris Foss show. Some guests of the show may be advertising on the podcast, but it's not an endorsement or review of any kind. Anyway, guys, we have an amazing young man on the show. We're talking about his business, his insights, entrepreneurship, and many other things. And also, you know, this is the time of year right now. It's November. We're recording this in 2025.

It's almost the end of the year. If you're a business owner or individual, you definitely want to plan your taxes because this is the last part of the year to get in, you know, whatever sort of write-offs and framing and different techniques you can do to save on taxes next year when you file them. You know, everyone does the last-minute thing. We've got an amazing young man on the show to talk to us about that. Douglas Carpenter, who's a CFA and CPA, a certified public.

Public accountant and chartered financial analyst. Douglas brings to companies over 40 years of business experience. He began his career at age 17, becoming the youngest registered stockbroker in America. He majored in accounting, worked five years at a top four accounting firm, and moved on to various consulting and chief financial officer positions. He's owned and operated comprehensive accounting solutions for seven years. His firm provides a full range accounting services to companies in all industries with a specialty in the challenging hospitality sector. His firm has a high-end specialty in providing tax-saving strategies to small business. Welcome the show. How are you, Douglas? Very well. Thank you for having me on the show, and I really appreciate

you referring to me as a young man. Give us your dot com so people can find you on the interwebs. We are at Solutions byCHS.com. It's a big, you know, Solutions with an S-B-B-Y-C-H-S. Charlie-Henry-Sanual. We cater to all kinds of small businesses, and we try to save your money on taxes in addition to doing a great job on your books. What's the constant life, death and taxes? Absolutely. You know what? It's the time of year that everyone's thinking holidays and having time off.

And you know what? I hate to insert that in there, but you really should be thinking about taxes too. That means don't forget to send a gift and a Christmas card to your tax guy. Yeah, they'll appreciate that very much. Now, you guys tend to target a lot of business to business. What is it? What's important for business owners to be thinking about right now? We do target a lot of businesses.

What they should be thinking about are the things you need to do to prepare for taxes. A lot of the year is over already. We understand that. We do a lot of analysis, but often we're going backwards. And we find in case over case over case, how much money's been left on the table. Our average business client that comes to us will look at a previous year return. We generally find what they could have done with the right strategies. We'd save them anywhere between $30,000 and up on their taxes.

It is amazing. Even a relatively low profit business can save money on taxes. So we look for all kinds of things, credits, ways of going through the tax system, and making sure you get the most out of it. What do you find that $30,000? That's a pretty good sum of money. I like businesses that, you know, make $10,000 and save $30,000. thousand. Is that possible? No, that isn't, although if you're making 10, you shouldn't be paying

anything. That's true. That's true. So what are some things business owners are overlooking? I mean, what contributes to that 30,000 if you want to tease out that a little bit? We don't expect you to give us a secret sauce, but tease that if you would. No, absolutely. It's, you know, you start with the basics, and there's a lot of things that businesses miss business owners. They're busy running a business. That's what they do. And then they go to get their tax return done. And, And a lot of people think that they're getting, you know, tax advice and tax planning and everything else, you're not. You're getting your tax return done. The person who's doing it may point out, hey, you should contribute more money to an IRA or something like that.

But they're not doing a deep dive into your situation. So some of the things that you might be looking at, let's talk about the basics, the 401Ks, the profit sharing, things such as that, passed through entity tax, which is significant to a lot of businesses. These are things that, you know, that they don't want to miss out on and make sure that to take advantage of. There's several segments to what we talk about. One is the tax savings side. The other is proper documentation, making sure that everything you do is documented. You'd said something in people, you know, people, there's a saying out there that billionaires don't pay taxes. And that's not true. Billionaires do pay taxes. They don't overpay taxes. You shouldn't overpay your taxes either. Yeah. And some people do. It's, you know, they just figure, oh, whatever,

it must be the right thing to do. But the great thing about being a business owner and entrepreneur is there's so many different things you can write off. There's, you know, and in business expenses if you take care of them and stuff. And what about structure, business structure? You know, there's a C-Corps, the S-corps, the sole proprietorships. Is that a thing that you take and help people do? Absolutely.

Absolutely. I'm glad you brought that up because that is a major thing that we look at. Most businesses are generally when they're established. we find that they have been set up correctly. I would say that S-Corp is very often the right answer, but not always. There are situations where you wouldn't. I don't want to really get too deep into that. Because the disclaimer I'm going to give here is anything that we say on the show, you need to go to a professional and make sure that it's correct. Everything has a caveat. Everything in the tax system is one way, and then there's six different exceptions to it. So you really have to get good advice.

But to address your point, there are things, considerations if you have, say, an S-Corp versus a 1065 versus a C-Corp that are very different. A C-Corp is taxed by itself. You receive a salary and dividends to the C-Corp, whereas 1065, which is a partnership or an S-Corp, or if you're doing a single-member LLC, which will go on your Schedule C, all of that flows through to you. So basically, whatever the business owns, it flows through to you. but there are things you have to consider S-corp's in particular. You need to pay yourself a salary. It needs to be reasonable. There's a lot of considerations in there.

A lot of things to take care of. I'll give you an example of something that someone missed. I mean, a lot of what I'm going to give you today is examples of things that people have missed. And one is health insurance. You pay your health insurance. Your company can pay the health insurance and it's deductible, but it has to be done correctly. It's done one way in a partnership. It's done another way for a.

a disregarded entity, which is a single member LLC, and yet a different way for an escort. Yeah, so interesting to plan for this and stuff. So I guess there's still, even though we're halfway through November, there's still moves you can make to maximize your tax returns next year and stuff as a business. Yeah, you know what? And since you do that, I'm going to basically run to a little bit of a laundry list that are put together here of some of the things to consider it. This may be, you know, come at you kind of fast, and there are details to it, but these are the things to talk with your tax advisor. First of all,

you know, HSAs, that is, you know, health savings accounts. These are extremely good tax vehicles. You put aside so much money for either medical expenses, you could save it for the future medical expenses, and it's tax-free if it's used for medical. If not, it's tax-deferred. There is some penalty if you don't use it for medical, but who isn't going to get older and use their HSA for medical expenses? That's something that you would want to establish. Of course, you know, there's your 401Ks, your profitory plans, they need to be set up by December 31st. You do a set by IRA, you have a little bit longer. You want to look at your proper salary if you're in an S corp. There could be capital loss harvesting. If you have capital gains,

you want to look for some capital losses. Maybe take up to $3,000 if you have an overall capital loss. There are equipment purchases that you can make this year that could be fully depreciatable or at least partially. You might consider backdoor Roth conversions. These are the things that you should be talking with your advisor. One of the most important in basics is getting your right estimates. Make sure you don't pay interest and penalties on the estimates that you put in. Make sure you've made enough estimated taxes. The general rule, and there are a few exceptions here, but it's 90% of, if you've paid in 90% of your current year taxes, or 100 to 110% of your prior year, you're covered. States are all a little bit different. You're pretty close to that,

but they're all a little bit different. But that's what you should be aiming at. One other thing, and I'm going to give this as a quick tip to a lot of business owners, they make money in the last quarter of the year. And I've heard this before. I said, I can't make quarterly estimates that are even. They don't make any money the first six months of the year. And then little, it and then I make it all in the end. So what should I do? There's a form actually. It's a 2210 that you file with your tax return that says, hey, I made all my money in the last quarter, which is why I didn't make my estimates in the first three quarters. However, that's, you know, that's if that's the case, that's what you do. If that's the case. What else? What do individuals

maybe need to take care of? I know you focus a little bit on businesses, but individuals can still make some moves, maybe, especially maybe they own a company. For me, you know, maybe I need to do something to balance up my individual taxes to get savings on business or how I pay myself, et cetera, et cetera, I don't know. They are one and the same. You know, an owner is not disconnected from their business return, even if it's a C-Corp. They're not, they're not disconnected. And there is a definite connection between the two. So you have to take your tax planning with a holistic approach. It needs to be looked at from both the business perspective and all the businesses you own and a lot of the people we have own multiple businesses. There can be interactions between

those businesses as well. If you have a business, you might have expenses that you incur personally, your cell phone, some of these things that you use for business, you want to reimburse yourself before the end of the year, those expenses. One of the ways of doing it, I think that's the best way documented. If you ever work for a company, you had an reimbursement form. It was an employee reimbursement. You submitted it with all your receipts and the company paid you. You can do the same thing with your own company. Treat it the exact same way. Even sign the report if you want it, if you really want it to be official. But have all those receipts, put them in as if you were an employee asking for reimbursement for these expenses. But do it before the end of the

year. Yeah. Once the end of the year closes out, you're kind of, it's done. right? It's kind of closed up. There are some things that you can consider after the end of the year. It's profit sharing and things like that that give you more time. You can set up a CepIRA up until the time you file your return. If you have an extension, it can go

all the way to the extension. But most of the things you want to consider are now. Definitely. Consider it now. Or else? Personal overpay. Yeah. I mean, is there ways, you know,

there's a lot of these billionaires, what they do is they do different games where they, you know, a lot of their money is tied up in stocks, their value is tied up in stocks, and then they take, I think my understanding is they take out loans to against those stock holdings. And then, of course, they can write off the loans or the interest in the loans, I guess, or something like that. Is there ways to do some of these tricks and tips that these billionaires are up to? You absolutely can. It depends on whether it's necessarily worth it, but yes, there are certainly ways of cashing out, if you will. It's another thing with C-Corp's.

If you have money in a C-Corp, you're going to pay double taxation. You're going to pay on the C-Corp level, and then when you take a dividend. But instead of it taking dividend, you can take a loan. There's some paperwork that you have to file. It really does need to be a loan. It's not a thing you have to pay interest on it. If it's personal interest, then you're not going to be able to deduct that. But it can be done.

And a lot of people do it. Hmm. Well, that should be, that should be definitely interesting. So people will take and try some of these tips and stuff. Why is it important to not do your own taxes, maybe? And how do you, how do you know if you have a good tax guy? I like, I like tax guys that are a little risky and to take advantage of stuff. I don't like guys that are a little too conservative. That's just me. But how do you, how do you make sure that, you know, your guy knows what he's doing when you're interviewing accounts? That's a good question. I'm not going to say this. I probably should say there's a lot of people that don't. I mean, you know, that's, you know, first of all, if you're doing your own taxes, you probably should also be your own lawyer, maybe be your own dentist as well. That is very true. You know, I probably spend, and I'm not exaggerating three hours a day, every day, seven days a week, studying tax codes, things. I mean, I'm in my mailbox looking at, you know, tax newsletters are coming in and reading them as I walk up my driveway. because I'm excited about this stuff and I want to see.

But if you're not doing that, you're not going to get everything. And you don't just have one tax code. Every state has a tax code too. And then you have the AMT on top of it. So if you can know all that, maybe it can come work for me. It's, you know, there's a lot to that. As far as you're professional, the question is, are they going above and beyond? And by that is, it's pretty easy to tell.

If they're asking you, give me your shoebox and let me put all the information down in your return, they're filling in a form. I mean, that's basically the first. That's not really what, you're not getting much out of it. Sometimes they don't even ask to write questions. You want a taxpayer that's going to ask you a lot of questions, maybe to the point where you're like, I've had enough of this, but they're asking you enough questions.

They're making suggestions. And if you're not sure of their suggestions, they can cite the tax code. And they can say, okay, this is where it comes from. That takes a little extra work. I wouldn't expect them to do that up front. But if you're not sure of something, The other thing is, if it sounds shady or too good to be true, get a second opinion.

If somebody's, I mean, who were those? I think it was a gentleman who played in the movie, the Blade movies, and he got some weird tax folks that were telling him, oh, you don't have to pay taxes. And so he went along with whatever his scheme was, and he ended up going to prison. You're right. Be careful who you listen to and make sure you get second opinions and stuff. And, you know, you find somebody who knows what they're doing. and can take advantage of.

Does it help the length of term that someone's been in business? You've been in business for, what, seven, eight years now or something like that? With this firm, yes. Obviously, I have a little bit more experience than that, but it does. It's important that they're not fresh out, you know, of what they do. And also their credentials. CPA is very important, I think. How much tax experience do they have?

What, you know, what do they do? And what do they specialize in? Not everybody specializes in every type of tax. there's nonprofit, there's trusts, there's estates, there's personal, there's business, all types of businesses. Some of the firms will specialize in a lot of different areas and they can cover everything, but make sure the person you're dealing with has the right experience. You can go to a big firm, but if you're not getting someone with that experience, you're not really getting much out of it.

Not getting much out of it. It's really important that you take advantage of everything you possibly can. And what about trust? Do you get into the trust area of the accounting and stuff like that? We do trust. We work with attorneys actually on trusts, especially in the setup and the recommendation of them and how they're used. There's a lot of tax planning that trust can be used for, especially in estate tax planning.

But this, again, is an area that falls under legal with accounting support. That's kind of the way we look at it. Got to run abast the attorneys. So they give it that rubber stamp. What are some of the things that you guys do in your business that maybe we haven't talked about? We should tease out to people. What we do is we do full accounting. We sound like, you know, I'm talking today as if all I do is tax, and it feels that way sometimes.

But I will tell you that we deal with, we do a lot of bookkeeping. We do a lot of accounting for business. We see a lot of books that come in. We have to do forensic work where, and by that I mean the books have not been correct in many years. We go back and we figure that out. You find that there's a loan on the balance. that's been there for five or eight years and the owner tells you, I don't know what that is.

And I see that more than you would think. Really? Wow. Oh, yes. Messy books. What about those? I've never known anyone personally, but what are those people who keep two sets of books? You heard of those folks? If you're talking about the people that aren't doing this correct,

you've got a real problem. First of all, I don't think I'd be interested in your business. but you know it was interesting because I had somebody that came in about two years ago and they outwardly admitted that they had not been let's just say they had not been doing their books correct and not that I wanted to know anything more but they did want them done right they didn't think that their last practitioner they got a little bit of a scare with an audit notice they weren't fully audited but they said you know what I want to sleep at night I want to do this. We did it, and the

interesting thing was, by doing it the right way and hitting all the right tax, financial, and planning areas, we saved them more money than he was cheating. Oh, really? Yeah. That's an interesting endorsement. Yeah.

Yeah. I mean, people sometimes cheat. I have to emphasize, don't cheat on your taxes. Don't cheat on your taxes. If you owe the tax, you pay the tax. But don't overpay the tax. Yeah, just don't overpay. I mean, The IRS gives you plenty of different things that you can utilize to take advantage of write-offs and different tax strategies. At the end of the day, if you make a lot of money, you're going to pay taxes.

That is the bottom line. But there's a lot of ways to defer them, avoid them, but evade is the word we don't use. Yeah. I used to have guys that come to work for me. We were in the mortgage business at the time, and we pay them a draw of like $2,500, but we had a lead system. So we could flood them with leads, and their earnings could really take off. And they would literally go from like $2,500 to making use within about four to five months, $20,000 a month, or at least $10 to $20, our top guys would make $20. And but they would go through this curve.

And a lot of times when we paid him the $2,500 a month, they could live on that. And then we, you know, we took them up. And the first thing I started complaining about is, I didn't realize all the tax you pay when you make all this money. And I'm like, it's a privilege, dude. I mean, would you rather live on the 20 money you started with and pay taxes on that? Or would you rather make 10 to 20 grand? And sure, your percentage of taxes is higher, but you're still making more money. It's so funny on people who are like, I just don't like paying all the taxes.

And I'm like, it's a privilege. Just shut up. You know, you bring up an interesting point. And we have some of our businesses are 1065, their partnerships, the 1065, the federal form that you file for them with their partnerships. And one of the questions I get is when should they do distributions. A big distribution year-end, I said, this is what you do. Do it when you file the taxes. They should get a K-1 and a distribution check. And the reason I say that is if you give it to them in December, year-end, they will spend it. They will spend it. And then there's

a big tax bill that potentially comes in. I say, make your distributions at the same time you file your taxes. This way you know exactly what it is. Everything's reconciled. You're all there. And not that you can't make distributions at other times, but for the main ones, I used to do a lot of work in hedge funds. That's when we would do the distributions. For that very reason, you know, people saying, I don't have the money to pay the taxes for this. This way you're giving them a check. There it is to pay the taxes. Yep. Yep. Pay the taxes, as it were. So you guys do accounting so people can work with you on a monthly basis. I guess, where you to sit down and do, what are some variations of accounting that you do?

Do people hand you their books or give you their software? We generally manage the accounting overall. What you get also obviously is the seamless integration between our books and the tax if you decide to engage us for tax as well, and most of our clients do. But really, we're probably underselling ourselves if we just say that all we do is the books, because really what we're being is financial advice. I was a CFO. Several of my staff were former CFOs as well. We look at the numbers and I can't look at your numbers and see a trend that I, you know, that's not within those numbers and not talk to you about it. One of the things that we like to do is have a quarterly conference call with our clients. We talk about how they've performed, what they've done. And one of my key questions that I love to ask this, and it's usually rhetorical they can discuss with me if they want, is what are you going to do different next quarter? that you didn't do this quarter.

Because if you're going to do everything exactly the same, your business will probably perform the same. That might be good, but most people want to advance the business or make it better, and it makes them think, hmm, what can I do this quarter upcoming that'll improve the business? It's a great exercise to have, take a couple hours out every quarter, have that discussion with me. Definitely, you know, because the business isn't growing, is dying. That's the rule of business. That is absolutely true.

It's like a sharp, it's always got to go. It's always got to go up. Yeah, yeah. And so people, you know, if it's not growing, it's dying, you've got to see them revenue numbers go up every month. You've got to be making some progress. Because if not, you're starting to spin out into that cycle. And sometimes once you get so deep, you know,

the next thing up is bankruptcy court. So mine your numbers. What are some other ways that you help people? maybe we have a teased out before we run off. One of the other ways is to manage cash flow. That's probably the most important thing in a business, particularly when you get into something. The others, construction business, things with large projects, very important to understand what your cash flow is and is going to be short-term projections, things like that.

We do budgets, but you know what people really look at is a three-month projection. We kind of joke, but it's not exactly false, is that we can tell you what your financials are three months before they happen. And that really is, we can do projections that look at what you're doing, see it, talk to you a little bit, get some feedback. And I can tell you what your financial is going to be for the next three months. There you go. That's good to know because then you've got to know if you're going up or down or what your future is. But yeah, I always remember, folks, if you're not growing, you're dying.

That's so unadage. I learn in business. And if you're dying often every month, it's just a matter of time. You really start spinning out because you start running out. of cash, cash flow like we talked about and everything else. So final thoughts and pitch out to people as we go out, tell people how they can onboard you, reach out to you, find out more, et cetera, et sure. They can visit our website. It's Solutions byCHS.com. I'm also DeCarpenter at Solutions byCHS.com. They can reach out. I'm more than happy to have a consultation, do tax planning,

deep tax planning, do part of the business. We're just, we're very happy. happy to help in any way that we can. It's been fun and insightful to have you on the show. We certainly appreciate it, Douglas. Thank you so much. I really appreciate it. Thank you, and thanks for us for tuning in. Be sure to check out to his website. Do we get the dot-coms as we go out on you, Douglas?

Yeah, it's, yes. All right. And go to goodreads.com, fortresschristch, chris-foss, Facebook.com, YouTube.com, Fortress, Chris Foss, 1, on the TikToky and all those crazy places. be good to each other. Stay safe. We'll see you guys next time. And that should have a sound.