My Favorite Day of the Year!

Summary

Armstrong & Getty On Demand: "My Favorite Day of the Year!" – Detailed Summary

Episode Release Date: April 23, 2025
Host: Armstrong & Getty
Guest: Stephen Moskowitz, Founder and Tax Attorney at Moskowitz LLP

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Introduction

In the "My Favorite Day of the Year!" episode of Armstrong & Getty On Demand, hosts Armstrong and Getty delve deep into the often daunting subject of taxes with their esteemed guest, Stephen Moskowitz. As a seasoned tax attorney and founder of Moskowitz LLP, Stephen brings clarity, expertise, and a touch of enthusiasm to what many consider a dry topic. This episode is a treasure trove for listeners seeking to demystify the complexities of tax laws and maximize their financial benefits.

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Meet the Guest: Stephen Moskowitz

Stephen Moskowitz is not just any tax attorney; he is a passionate advocate for leveraging tax laws to one's advantage. With years of experience representing a diverse clientele, Stephen has become a trusted name in the realm of personal and business taxes. His approach combines deep legal knowledge with practical advice, making tax strategies accessible to all.

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Favorite Day of the Year: April 13th

At the beginning of the discussion, Stephen shares his favorite day of the year: April 13th, as mentioned at [02:51]. While this might seem unconventional given the typical association of mid-April with tax season stress, Stephen reveals the personal significance tied to this date, setting the stage for a candid conversation about taxes.

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Timely Tax Return Filing Tips

One of the primary topics Stephen addresses is the importance of timely tax return filing. He emphasizes the pitfalls of procrastination, advising listeners not to emulate the frantic, last-minute rush often depicted in movies ([03:09], [04:00]). Instead, he recommends:

• Filing for an Extension: While filing an extension grants more time to submit tax returns, it's crucial to understand that it does not extend the time to pay any owed taxes ([03:09]).
• Payment Plans: If unable to pay the full tax amount, Stephen advises filing the return regardless and paying what one can, subsequently setting up a monthly payment plan with the IRS.

"If you're reasonable with them, they’ll be reasonable with you. You can work something out. You don’t have to be afraid of it." ([04:50])

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Demystifying the IRS

Contrary to popular belief and Hollywood portrayals, Stephen reassures listeners that the IRS is not the monstrous entity often depicted. He explains that the majority of IRS employees are merely performing their duties, and with honest communication, taxpayers can navigate their obligations without undue stress.

"The IRS is portrayed as monsters. They're not; most of them are just doing their job." ([04:10])

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Maximizing Tax Benefits for Everyone

A standout moment in the episode is Stephen's emphasis that tax benefits are not exclusive to the wealthy. He outlines various deductions and incentives available to individuals across the income spectrum:

• Homeowners: Deductions on mortgage interest and real estate taxes.
• Business Owners: Depreciation on machinery and buildings, accelerated deductions, and pension contributions.
• General Benefits: Tax deductions for setting up pensions, retirement plans, and more.

"The tax law has something for everybody in it. It’s worth it. Knowing it, studying or going to somebody who does, there’s just so much there." ([06:32])

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The Ever-Expanding Tax Code

Stephen delves into the historical growth of the tax code, highlighting its complexity and the challenges it presents:

"When you argue tax law, it’s one of the things you don't realize about tax law, but that’s part of the beauty of it, or at least the way the system works." ([06:54])

He compares the current tax law to a vast tapestry, continuously woven with new interpretations, amendments, and judicial decisions, making it both a fascinating and intricate field.

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Home Office Deductions: Benefits and Drawbacks

With the rise of remote work, many listeners are curious about home office deductions. Stephen provides nuanced insights:

• Eligibility: To deduct a home office, the space must be used exclusively for business purposes. Even a single-room studio apartment can qualify if appropriately designated ([11:41]).

• Potential Downsides: Deducting part of one's home for business purposes can convert that portion from a principal residence to business property, affecting tax benefits upon the property's sale. This can introduce complexities like depreciation recapture ([11:41]).

"It’s like medicine. This is a good medicine, but there's a side effect which may or may not affect you." ([12:32])

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Strategic Pension Planning

One of the most enlightening segments revolves around pension plans and their strategic tax benefits:

• Deferred Deductions: Contributions to pension plans can often be deducted not only in the current tax year but also when filing for an extension, allowing for significant tax shields ([15:52]).

• Multiple Plans: For high earners or those with substantial incomes in a given year, setting up multiple pension plans can exponentially increase deductible amounts, effectively reducing taxable income ([15:52]).

"You set up pension plans, and by the way, you can have multiple pension plans in the same year, you set up multiple pension plans, and then you make multiple plan your contributions in one calendar year, you get a gigantic deduction against that fantastic year." ([14:37])

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Importance of Professional Guidance

Throughout the conversation, Stephen underscores the value of professional tax advice:

• Avoiding Self-Cheating: Many individuals inadvertently cheat themselves by not fully utilizing eligible deductions and benefits.
• Complexity Handling: Given the intricate nature of tax laws, professional guidance can uncover hidden opportunities for substantial savings.
• Long-Term Benefits: Investing in a tax professional can result in significant financial gains, often outweighing the costs.

"Most people cheat on their taxes. They cheat themselves by not taking advantage of everything they're entitled to." ([15:52])

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Notable Quotes

• "A positive cash flow with a tax loss, isn't it the most beautiful words in the English language." – Stephen Moskowitz ([05:32])

• "You set up pension plans...you make multiple plan contributions in one calendar year, you get a gigantic deduction against that fantastic year." – Stephen Moskowitz ([14:37])

• "Knowing it, studying or going to somebody who does, there's just so much there, and yet so many people treat it with despair. And it's horrible. You have to take a look at all the good things that they're there." – Stephen Moskowitz ([06:32])

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Key Takeaways

1. Proactive Filing: Don't delay tax filings. Utilize extensions appropriately and ensure timely payments to avoid penalties.

2. Leverage Deductions: Tax laws offer a plethora of deductions and benefits tailored to various financial situations. Understanding and utilizing them can lead to significant savings.

3. Seek Professional Help: Given the complexity of tax codes, consulting with a tax professional can maximize benefits and minimize errors.

4. Stay Informed: Continuous learning about tax laws empowers individuals to make informed financial decisions and capitalize on available incentives.

5. Balance Benefits and Drawbacks: While deductions like the home office offer advantages, it's essential to be aware of potential long-term implications.

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Conclusion

The "My Favorite Day of the Year!" episode of Armstrong & Getty On Demand serves as an invaluable guide for anyone navigating the labyrinthine world of taxes. With Stephen Moskowitz's expert insights, listeners gain a clearer understanding of how to optimize their tax strategies, avoid common pitfalls, and harness the full potential of available deductions. Whether you're a freelancer, a business owner, or an individual taxpayer, this episode equips you with the knowledge to approach taxes with confidence and strategic intent.

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For more insights and detailed discussions, tune into the full episode of Armstrong & Getty On Demand.

Transcript

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[Ryan Seacrest]

But first, let's talk taxes with Stephen Moskowitz, the founder and tax attorney at Moskowitz llp, longtime friend of the Armstrong and Getty show and advisor on matters tax as well. Stephen, how are you doing?

[Stephen Moskowitz]

Great. My favorite day of the year, April 13th.

[Armstrong and Getty Host]

Yeah, not mine.

[Ryan Seacrest]

Yeah, you're the only one, but. So you're always brimming with interesting tax talk. You love your job as much as anybody in America. So what's top of mind for you today to communicate to the good folks?

[Stephen Moskowitz]

You know, there, there's so much. If you haven't done your tax return by now, don't be like in the movies. Work until midnight to get it out. Go on extension. Now, the extension is an extension of time to file, not an extension of time to pay. But if you can't pay your taxes, don't make the mistake of not filing return. File it, pay what you can, and then you can do a monthly payment plan. And you know, I know in the movies the IRS is portrayed as monsters. They're not, you know, like any large group, there's always a bad apple and there's always somebody great. But most of them are just doing their job. If you're reasonable with them, they, they'll be reasonable for you. You can work something out. You don't have to be afraid of it. You can work something out. That's what we do for people. But the bottom line is these problems are fixable. And I've seen over the years so many people, they go into hiding, they do these horrible things, they punish themselves way worse than the government ever would, and there's no need for that. On the other hand, there's so many tax benefits. If you're a do it yourselfer, there's a lot of good things to read. You might also want to consider talking to somebody. There's so many advantages, especially if you're in business. You take a look at the Fortune 500, that's one of the things that originally motivated me to become a tax attorney because, you know, as a CPA first and I watched these giant corporations making billions of dollars and legally paying little or no taxes. And how can that Be. Our tax law is based on two things. One, getting money from us, we all know about that one. But the other one, in a democracy, the government can't order us to do things, but they want us to do things because it's good for the economy. So how they get to do it, they pay us. And that's the secret of all these tax deductions. There's all kinds of tax incentives. We see simple ones like buying a house, you get a tax deduction for mortgage interest and real estate taxes. You set up a pension for yourself, you get a tax deduction for that. There's so many benefits where, if you have depreciation on machinery or buildings, there's ways to accelerate that and get way more. Get these huge deductions. Another thing, to me, the most beautiful words in the English language or a positive cash flow with a tax loss, isn't it.

[Armstrong and Getty Host]

It's romantic in your life.

[Stephen Moskowitz]

I mean, it brings a tear to the eye. It's so emotional. To me, the bottom line is there's so much there where you can, you can benefit. And I mean, there's benefits for everybody. It's not just for rich people. It's for everybody. If you're on the lower end of the income scale, the government gives you all kinds of benefits for you, for your kids, family members. If you're on the other end, there's ways that you can deduct your yachts and everything in between. The tax law has something for everybody in it. It's worth it. Knowing it, studying or going to somebody who does, there's just so much there, and yet so many people treat it with despair. And it's horrible. You have to take a look at all the good things that they're there. You just have to know about them.

[Armstrong and Getty Host]

So we talk a lot about. You've talked a lot about how the complexity of the tax code. I mean, if, if we're starting the tax code today, nobody would want to end up with what we currently have, even though it's so hard to change. But like, when you started many years ago, how many pages or rules were there compared to today?

[Stephen Moskowitz]

Oh, you know, I remember when I was in grad school, the professor actually went over that and he took it even back further where he basically showed us with his hands. He said when he started in tax, basically the tax law was. And he opened his fingers to show us now. He said, today, this is back when I was in school, he opened his arms, he said, that's not wide enough. And what happens is it's not just the law, it's the interpretations. A lot of what we do is we argue over what did the legislators in their infinite wisdom provide for us. And oftentimes the judges can't agree. And so many times we'll do a settlement because both sides say, well, we don't really know what they meant. So rather than have the judge decide, let's make a deal. And again, you see judges disagreeing, you say appeals judges disagreeing with trial judges. It's almost like nobody knows. It's a grand mystery, one of the mysteries of life going through this. It really is. I mean, I know how excited I get about tax law, but it really is the mysteries of life. And in real life, it's not a black and white mathematical. One plus one equals two. That's the right answer. It's like going into the museum and looking at the paintings and say, what's the most beautiful painting here? It's a matter of interpretation. And there's so much of the tax law like that, what the legislators mean. And when you argue tax law, it's one of the other things too. You try to figure out what did they mean and you, you negotiate about it to try to figure out what they mean. That's something people don't realize about tax law, but that's part of the beauty of it, or at least the way the system works.

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[Ryan Seacrest]

Real life, the topic I've probably heard the most from people being confused about is if they're working remotely, part time or full time. They've got a home office. I've got a home studio. Can you deduct the equipment you buy? The chair you're sitting on? What are the pros and cons of that?

[Armstrong and Getty Host]

Your WI fi because you're using it at home?

[Stephen Moskowitz]

Yeah, you may be able to. And what you have to watch out for, the most common was the home office. People say, can I deduct the home office? Now, in order to deduct it, the way you do it is you say, okay, if you use a portion of your home exclusively for business, you can deduct it. And even if you had a studio apartment that's one room, how can you do that? The tax court has ruled us, we use a portion of that room exclusively for business. You can do it, but you have to watch out. There's a downside to doing it. And the downside to doing is it converts that portion of your home from your principal residence, which has all kinds of tax benefits, into business property, which doesn't. So if you sell the house, then all of a sudden you learn about things you have to give back, like depreciation, recapture and other things. So it's. If you're thinking about deducting home office, you can do it if you qualify, but you may not want to.

[Armstrong and Getty Host]

I never thought about the end when you go to sell your house and that, that's not a house, that's an officer selling. And here's the everything that goes with that.

[Stephen Moskowitz]

Exactly. So the bottom line is it's kind of like medicine. This is a good medicine, but there's a side effect which may or may not affect you. So we talk about that. And the bottom line is another thing that's really good for people is if you're an independent contractor, you set up your own business and then you take pension deductions, retirement, and there's so many benefits, you get a big tax deduction. And one of the things with retirement, like we're here, it is, it's April 15, and you say, well, these are all good things for next year, but there's some things you can still do. Suppose you put your return on extension today. There's many different types of pensions. Most, but not all of them provide for an exceptional tax plan. Because most things with tax plan, you have to write the check by December 31, 24, deduct the 24. Not with most of the pension plans you have up to the time of filing the return plus extension, which means suppose you put your return on extension today. That gives you half a year to set up a pension in 2025, fund it in 2025, and then you can elect to deduct it from your 24 taxes. So the bottom line, think about you earned money last year. You have another six months, happy year to earn money put away for yourself and take a deduction for last year, 24. I mean, to me, this is just fascinating.

[Ryan Seacrest]

So that would be like a small business person who had a really great 2024 and is getting hammered with taxes. It can in effect shield some of that income from tax by putting it in a pension plan, like retroactively.

[Stephen Moskowitz]

Ah. And when somebody gives you something nice, what do you say?

[Ryan Seacrest]

Thank you.

[Stephen Moskowitz]

The lawyer Says, more, I want more. And what happens is, with the really great year you talked about with the pension plans, if you had a fantastic year, one of the things you can do, they're so flexible, is you can make multiple plan year contributions in one calendar year and get a much, much bigger deduction for that year. So suppose you were a salesman or you had something else, you had a big sale, you made a lot of money. What you want to do is you want to get, let's say that was 24. You say, I'm looking at these taxes. I hate all these taxes. So you set up pension plans. And by the way, you can have multiple pension plans in the same year, you set up multiple pension plans, and then you make multiple plan your contributions in one calendar year, you get a gigantic deduction against that fantastic year. And it's one of the ways you don't pay taxes on it. See, this stuff really lives, doesn't it?

[Ryan Seacrest]

And then you end up taking it out years down the road when you're paying at a much lower rate, theoretically. All right, we've got like two more minutes. Stephen, anything else you want to squeeze in before we let you go?

[Stephen Moskowitz]

Yes, before you send your taxes in, you really want to learn as much as you can, either on your own for reading or going to somebody that does this. Because most people cheat on their taxes. They cheat themselves by not taking everything to which they're entitled. And, you know, there's just so much to the tax law. I know it's really complex, but there's so many benefits for you. So the bottom line is like so many other things in life, you get out of it what you put into it, learn about it, or go to somebody that does this for a living, and you can really benefit. You see, there's so much difference in people's taxes. And again, my example is the Fortune 500. Look at all the money they make. Look at how little, little or nothing you pay in taxes. That's not just for the Fortune 500. That's for everybody that knows about it. It's there for you. It's alive, it's legal. And that, that's what I do for a living. And no kidding, this stuff fascinates me. And it's so great to be able to legally do this.

[Ryan Seacrest]

Stephen Moskowitz, Moskowitz llp, longtime friend of the show. Stephen, always a pleasure to talk to you. It's always interesting if you want to talk to Stephen. One triple eight, ten tax deal. One triple eight tax deal. Stephen, thanks for the time Appreciate it.

[Stephen Moskowitz]

Thanks so much. I had a great time, as always.

[Ryan Seacrest]

Got it.

[Armstrong and Getty Host]

Now, obviously he gets paid to do taxes, so, you know, he would have an incentive to convince you to have a guy. But I don't doubt that that's true. Absolutely true that the majority of people cheat on their taxes. The cheating is you cheat yourself by not taking advantage of everything.

[Ryan Seacrest]

Yeah. And this is, again, this is not a commercial in any way, but. And it depends on your financial circumstances, where you are in your life, and a hundred other things. So. So, you know, it's entirely up to you. But our experience, Jack and me, as individuals and as business partners has been you spend hundreds and save thousands by consulting professionals. And maybe your situation is you'd spend thousands and save tens of thousands, you know, again, depending on your life circumstance. But that's been our experience.

[Armstrong and Getty Host]

One of my main takeaways from knowing Steven, and I think he brought this up at a lunch we were at with him one time, is, is the idea of. And it's changed the way I think about things. But like, would you. I mean, a basic question of would you rather get. Would you rather have. Be receive $50,000 or $80,000? Well, obviously I'd rather receive the $80,000. What are the tax implications? How is the 50,000 coming to you? How's the 80,000 coming? Is it coming through income? Did your grandma live it to you? You know, is it a prize you won? It's a. Because there are different tax implications for all these different things. You might be better off with the 50,000 than the 80,000. If it was a gift, then if it was income, blah, blah, blah. And you always have to look at that end of it.

[Ryan Seacrest]

It should not be that dizzying, but it is.

[Armstrong and Getty Host]

Right. I hope you enjoyed that. I did. I always get something out of it.

[Ryan Seacrest]

More on the way.

[Armstrong and Getty Host]

Stay here.

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[Stephen Moskowitz]

Hello.

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