Amber Gray-Fenner, EA NTPI Fellow USTCP, Author at Think Outside the Tax Box


Amber Gray-Fenner, EA NTPI Fellow USTCP

Amber Gray-Fenner is an Enrolled Agent, National Tax Practice Institute Fellow, and United States Tax Court Practitioner. She is the owner of Tax Therapy, LLC in Albuquerque, New Mexico. Amber’s practice focuses on tax returns and tax planning for individuals and small professional businesses with a bit of representation thrown in to keep things spicy. In 2020 Amber was selected as one of the Top 100 Must Follow Tax Twitter Accounts. Amber was born and raised in Las Vegas, Nevada, and has a Bachelor of Arts in English from UNLV.

READ MORE BY Amber Gray-Fenner, EA NTPI Fellow USTCP

Split Dollar Life Insurance

Using Split-dollar Life Insurance as a Tax Loophole

I’m no fan of needlessly complicating people’s tax situations, and I often remind readers to consider administrative overhead and compliance costs in addition to tax savings when evaluating tax strategies. The following strategies work best for high-net-worth taxpayers and medium to large “small businesses.”

I’m not talking about people who think they are high-net-worth, but if even after the estate tax exemption was doubled, you have to file an estate tax return (Form 706), this is you. If your individual or business net worth is in or is approaching the double-digit millions, this may not apply to you – yet. Keep reading anyway because it may be only a matter of time before you can use it or one of your “I wanna be a playa” clients comes to you asking about this strategy because they saw it on TikTok.

Keep reading to learn more on how to save.

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Turning Services Into Property Can Create a Non-recognition Event

Turning Services into Property Can Create a Non-recognition Event

It’s not often that we get to wave a magic wand and turn a taxable transaction into a non-taxable transaction, but partnership taxation offers us this opportunity. Partnership taxation is extraordinarily flexible and combines tax-favored aspects of both corporate entity taxation and individual taxation.

Proper planning and use of this flexibility can actually turn a contribution in return for a partnership interest from a recognition event that results in taxable income to you to a non-recognition event that merely adds to your basis in the partnership.

The difference between contributing services versus property for a partnership interest is huge. Contribute services, and you have taxable compensation. Contribute property, and you have a non-recognition event. Determining whether your contribution is classifiable as property rather than services saves a ton in tax. Keep reading to learn how.

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Thinking About Selling Body Parts as a Side Hustle? Review the Tax Consequences First!

Sometimes my mind is not the safest place to be. I mean face it, a few issues ago I wrote on best practices for doing Al Capone’s tax returns. But how did I even get started thinking about the taxability of a business dealing in black market organs? Well, it started when someone on social media (perhaps looking to supplement the income from their tax practice) asked if the gain on selling a kidney was taxable and, if so, what would be the seller’s basis in the organ? Then there was that time I was having dinner and adult beverages with some tax colleagues in Las Vegas, and we started talking about that old urban legend about waking up in a bathtub full of ice missing a kidney. It was a fun night, and we all woke up with all of our kidneys and other organs in place. Nevertheless, I found myself wondering (and continuing to wonder) about the tax consequences of transacting in human body parts—one’s own or those illegally harvested from others. Turns out, there have been some court cases on the topic which means that the discussion is more than merely theoretical.

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Taking Cash from Your C Corporation: Which Tactic is Best for You?

Being a shareholder owner of a C corporation comes with certain benefits, including the ability to take cash from your business. How to do so depends on your short- and long-term goals and consideration of the tax trade-offs. This article will discuss the options available to shareholder owners, other than borrowing, to realize cash from a corporation that is expected to continue.

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Soapbox Ethics: Circular 230 And the Unauthorized Practice of Law

The beneficial ownership reporting requirement established by the Corporate Transparency Act has created a fair amount of chaos concerning whether providing reporting services to clients is the unauthorized practice of law (UPL). While some state bar associations have come down on one side or the other as to whether certain types of reporting are UPL, the Treasury offers no clear guidance. What the IRS has made clear recently is that Circular 230 ethical obligations extend to matters beyond what the Loving case determined was “practice before the IRS.”

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Segregating Activities Can Optimize Tax Savings for Professional Gamblers, Gamers, and Contestants

You’re tax professionals. You don’t need me to tell you that the money you are going to win in the virtual office pool on “the big game” is taxable income. You also don’t need me to tell you can’t net your winnings with the cost of the wager. You don’t, right? Most of the rules for reporting gambling income and deducting gambling losses for individuals are well understood with the possible exception of the session rules for slot machine play. I’m not going there—well, not in this article. This article is going to explore the nuances of tax optimization for people who have decided to go all in and turn their leisure time activities into a job.

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Retirement Tax Planning — Retirement Plans for the Sole Proprietor

Many of the same tax advantages perceived as being only available with entity taxation are also available to Schedule C sole proprietors and that includes funding retirement plans. It’s perfectly OK to start and continue to run a business as a sole proprietorship filing a Schedule C for when it makes financial and administrative sense to do so.

There are a number of advantages to having a retirement account. Of course, when you contribute to a retirement account, you can deduct your contributions from your taxable income. This can result in significant savings come tax time. Additionally, the money in your retirement account grows tax-free. This means that you can potentially earn a lot more on your investment than you would if it were subject to taxation. A retirement account gives you the peace of mind that comes with knowing you have a cushion to fall back on in retirement. No matter what happens in the markets, you will always have access to your retirement savings. This can provide a great deal of security during uncertain economic times.

While retirement accounts can be a great way to save for the future, there are also some potential drawbacks to consider. For one thing, retirement accounts often come with strict penalties for early withdrawal. This means that if you need to access your savings before retirement age, you may be subject to significant fees. Additionally, retirement accounts can be complex and confusing, making it difficult to keep track of your progress.

While retirement accounts can be a helpful tool for saving, it’s important to be aware of the potential drawbacks before you decide as a sole proprietor whether or not to open one. Click here to explore the different types of retirement plans available to sole proprietors and the pros and cons of each.

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Retirement Tax Planning – Work for All Seasons of Life

The single best skincare tip for avoiding wrinkles is to stay out of the sun. What does this have to do with retirement tax planning? Well, much as skincare shouldn’t stop when the first wrinkle appears, tax planning for retirement shouldn’t stop at retirement. Tax planning for retirement is an ongoing balancing act that, in a perfect world, begins with the first earned income and continues for the remainder of the taxpayer’s life. The trick is to balance tax strategies that help while a client is working with tax strategies that are going to benefit the client once they retire all without having a crystal ball as to how tax laws may change in the short- or long-term future. This article is the first in a four-part series that explores tax planning strategies both before and during retirement and discusses the importance of pro-active planning before and during retirement.

Keep reading to learn more…

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Retirement Tax Planning – Having a Rough Year? Turn Lemons into Lemonade by Using Business Losses to Offset Roth IRA Conversions

A ROTH conversion can be a very powerful tool for your retirement. While you don’t receive a tax break for deposits to your ROTH account, qualified withdrawals from the account are tax-free, even earnings. This is an excellent way to avoid tax increases. Let’s say your taxes rise due to increases in tax rates, or because you earn more, which catapults you to a higher tax bracket, ROTH IRA conversions can save you a ton of money in taxes over the long term.

The disadvantage, of course, is that tax is due on the amount you convert based on the value at conversion. But many times, such as when you are in a temporarily low tax bracket, have large deductions during the year, or in a year with business losses, can provide optimal opportunities to convert with little to no tax expense.

Looking for more strategic times to convert? Keep reading to learn more.

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Qualifying Your Clients for the R&D Credit

Companies that specialize in the Credit for Increasing Research Activities (also known as the R&D tax credit) sell hard to our clients. During tax season they are online looking for businesses who may qualify for this credit—especially startups. They cast an extremely wide net that has the potential for a lot of bycatch. While it’s true that the R&D credit is often overlooked by small businesses and their return preparers, it’s not as easy to qualify for the credit as some of these companies want small business owners to believe. Savvy tax professionals can help to ensure that their qualifying business clients receive the benefit of this credit while avoiding situations that would make them ineligible for it.

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Making Smarter Retirement Account Distributions by Asking When, Why, and Where

As a proactive client, you often ask your tax professional about the tax effects of taking distributions from your retirement accounts. Unfortunately, it seems that proactive clients are in the minority. More often, your tax professional only learns about your retirement account distribution when the Form 1099-R arrives with your other tax documents.

Proactive tax planners can improve their tax savings strategies by asking the when, where, and why that can help reduce negative tax consequences and can make you look like a problem-solving rock star to your clients.

Whether you are looking for proactive ideas to implement on your own, or you want to be a problem-solving rock star with your tax planning clients, keep reading to learn how to make smart retirement account distributions.

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Just Good Business: What to Consider When Choosing an Entity

Just Good Business: When It’s Time to Hire a Pro

Often, clients and potential clients grumble when their tax professionals recommend hiring a bookkeeping and/or accounting professional. Why? Because many people (including some tax practitioners) simply do not understand the miraculous complexity that is double-entry accounting.

As some are probably aware, proper bookkeeping and accounting are much more than simply entering income and expenses into a software program. Nevertheless, it is sometimes difficult to explain the nuances of and the necessity for double-entry accounting to clients.

Following are the specific circumstances under which clients should hire a professional bookkeeper and/or accountant. And remember, what works for clients also works for busy tax and accounting professionals.

You may, after reading this article, decide that it’s in your own best interests to outsource your business’s tax and accounting work both for peace of mind and for time and money saved. So, when is it just good business to gently insist that your client hire an accounting professional? Keep reading to find out.

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Just Good Business: What to Consider When Choosing an Entity

Just Good Business: What to Consider When Choosing an Entity

It’s every tax professional’s favorite answer to the question “How is your business organized?” “I have an LLC.” It’s the non-answer answer. Unfortunately for many clients and practitioners, clients often decide to form an LLC for no reason other than “they said I should” and more often cannot provide a good answer when the practitioner asks, “Who is ‘they?”

Ideally, small business clients should consult both an attorney and a tax professional when deciding to form a business entity under state law. Because while state law governs entity formation and many aspects of entity administrative compliance, federal and state tax law determines which tax returns you need to file and which tax laws apply to the entity.

It is just good business to make a mindful, proactive choice when choosing a type of business entity. Making a conscientious choice means asking the right questions. And when choosing a business entity, asking the right questions means asking questions about matters other than simply tax considerations.

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Just Good Business

Just Good Business: Partners in a Real Estate Deal? Think Twice Before Forming That LLC

The limited liability corporation or LLC is one of the most popular entity choices for small business owners. And for good reason. An LLC is relatively simple to form and, as the name suggests, it provides a limited amount of liability protection for business owners.

Nevertheless, some business owners are often unaware that an LLC has no inherent tax advantages (because, as our readers know, the Feds disregard it for tax purposes) over other types of entities (or even no entity at all). You should always be encouraged to make your entity choice based on a variety of factors, including both potential tax treatment and the administrative burden associated with it.

How do you use an LLC to save tax, and better yet ensure it isn’t costing you more than it needs to? Keep reading to find out.

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Just Good Business

Just Good Business: How to Keep Business Records for Tax Compliance

One of the most common non-tax questions clients ask tax professionals is “How long should I keep this?” “This” could mean bank records, copies of tax returns, or virtually any other piece of business information. This reasonably comprehensive overview focuses on keeping business records for tax compliance, specifically, what to keep and how long to keep it in case a taxing authority ever decides to examine (audit) a business return. Records management is an entire field unto itself! Hiring an in-house records manager is beyond the needs or the budget of most small businesses, but it’s important to understand that proper records management is serious business.

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Just Good Business – Review Your Insurance Policies

Regular readers of this column may know that I came involuntarily to the tax business. I inherited it from my mother in 2010. Less well known is that the tax business was Mom’s side hustle. Mom’s main business was as an independent insurance agent.

The insurance side of the business closed in 2017, but during the time I was administering that side of the business (I was never a licensed agent), I learned a lot about insurance. One of the most important lessons I learned was that the longer you hold a policy, the more the rates increase and that it pays to make the effort to review (and shop) your various insurance policies regularly.

Another important lesson was that all coverage is not equal and, just as when looking for a tax professional, price should be a consideration but not the consideration.

The third important lesson was to know your coverage before you need the insurance. Many times we had to remind a customer they had refused uninsured motorist coverage to save a few dollars after an uninsured motorist totaled the client’s vehicle or to explain the limits of flood coverage after a building flooded.

Regularly reviewing your insurance policies for coverage and value provides peace of mind and is just good business. Click here to learn the ins and outs of getting a great deal.

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Just Good Business – Review Your Fixed Asset List for Hidden Deductions

Most businesses require the purchase of equipment or other property to help generate income. How you deduct the costs of these business assets depends on what it is and how long it will be useful (what are called asset classes and the Business Use Percentages (BUP)).

In some situations, you can deduct the full cost of the asset the year you buy it, rather than depreciating it over time, but many times you are deducting a portion of what you paid for the property each year you have it.

Fixed assets are assets that have a useful life of more than one year and/or are not expected to be converted to cash within a year (those types of assets are current assets). Land, buildings, furniture, and equipment (including vehicles) are the most common types of fixed assets for businesses.

Fixed asset listings are records of the costs of business property and what tax deductions or improvements have been made over time. Unfortunately, these lists can get quite messy and confusing over time, especially the longer a business is in operation, and the more frequently you have changed tax professionals.

What most business owners (and even their tax advisers) don’t know is that there are often thousands in tax savings contained on these lists, especially when they are messy or confusing.

There are four savings opportunities buried in these records and what you do with them can result in less cash to the IRS.

Continue reading to learn more.

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Just Good Business – Review Your Beneficiary Designations

It seems so simple, right? You open an account and as you complete the paperwork, you enter something on the line labeled “Beneficiary,” and that’s that. But how many accounts are there? What about other assets? What about, well, life? Because life happens, it can have odd effects on the distribution of assets. This is a cautionary tale of unintended consequences and a reminder to review your beneficiary designations, if not annually, at least every time you experience a major life event.

Consider a retired couple one of whom has a large 401(k) (or similar) account. Both have Social Security and true pensions, as well. Typically, the Social Security and pension benefits will end with the death of the individual. The 401(k), however, remains and the listed beneficiary is the spouse. The beneficiary spouse dies before the spouse with the 401(k). Upon the death of her spouse, the account holder creates a will using a popular online tool, which does not advise her to review beneficiary designations on her bank, brokerage, and retirement accounts.

Keep reading to learn what to check, when, and how to avoid what goes wrong.

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Just Good Business – Review Your Administrative Compliance

Tax season is in full effect, and it is likely that you are seeing and coping with the effects of poor administrative compliance on the part of your small business clients. Instead of bemoaning the fact that so many clients “don’t get it” use some of the time you’re spending on the return to prepare a list of administrative compliance items that the client needs to address. Then, set a (paid) planning appointment for later in the year to help the client address those items. If you do this, and if the client heeds your advice, next filing season more (if not always all) of the client’s administrative compliance will be in order by the time you start preparing their returns. It’s a win-win. Your client gets the opportunity to ensure that they are meeting administrative requirements that protect them from liability or penalties. You get cleaner paperwork (and peace of mind) moving into next filing season. Read on to learn more!

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Just Good Business – Review Your Accounting and Tax Compliance

Here we are in the thick of another tax season and tax professionals everywhere are bemoaning the standard litany of issues: unreconciled bank accounts, balance sheets that don’t balance, unfiled 1099s, etc. It doesn’t have to be this way, at least not for you and your clients. Tax season is actually the perfect time to review and/or set and implement best practices for tax and accounting compliance in your clients’ businesses—and yours. Physician, heal thyself.

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Just Good Business – Review and Shop Your Financial Accounts

The fourth quarter just started and it’s time to have your clients take a look at their financial services game plan. With interest rates approaching historic highs now is the time to review financial accounts to ensure high returns on cash investments, optimize reward-bearing accounts, and minimize interest paid and fees for financial products and accounts. The goal of this review is to ensure that investments and rewards programs are tuned for optimal results and to minimize interest and fees throughout next year. I won’t be providing much in the way of specific, prescriptive advice. I am not a registered investment advisor or a certified financial planner, nor do I recommend specific products, services, or institutions (other than a subscription to this publication). Rather, I will be providing a framework for the review, encouraging you to ask good questions about the goals for the various accounts, and reminding you to consider the big picture as well as the role each part plays in it.

Let’s get started!

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Just Good Business – Develop or Review Your Employee Handbook

An employee handbook is usually designed to cover everything a new hire needs to know to get started at their job. Depending on the size of the company “everything a new hire needs to know” can be either a vast amount of information or a much smaller amount. Many small, closely held businesses may not have an employee handbook because they don’t feel they are large enough to warrant it or they (mistakenly) believe that necessary information is getting communicated effectively and consistently to all staff members. Often having an employee handbook isn’t something most businesses think about until it’s too late (for example, when an employee files a lawsuit for discrimination or a worker’s compensation claim). Even businesses that have an employee handbook may not give it much thought once it has been developed. But developing and maintaining a useful employee handbook is just good business. Why? The employee handbook explains a company’s culture and values and is a valuable reference tool for employees looking for information on company policies. It can save management time (and money) and can help to prevent or mitigate legal issues for the company.

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Just Good Business – Curate Your Tech Stack

We’ve all done it. And most other business owners are doing it, too. What is “it”? Succumbing to the promise of “there’s an app for that” and registering for technology of all kinds – and then not using them. You should review and curate your tech stack at least once a year. Why? Because in business, plans often change. Priorities change, new challenges arise, and new opportunities appear. Curating your tech stack annually is just good business.

Curating isn’t simply about getting rid of products and services that aren’t meeting your needs it’s also about mindfully adding technology that will help your business to grow (if that’s your goal), help you provide better customer service, and help you manage your business in a way that, one hopes, frees up your time for other activities whether those activities are business- or life-related. Nevertheless, it’s often necessary to clear bandwidth-sucking technological clutter before shifting our focus to identifying problems that tech can solve. Too much tech clutter (like too much physical clutter) can prevent you from seeing problems (and potential solutions) clearly.

Additionally, this is an activity that can cut unnecessary expenses from your bottom line and improve upon technological advances. It is possible since the time you first subscribed to an application that there are better, cheaper alternatives.

Here’s what to consider step-by-step to grow your take home pay and improve your business practice.

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Just Good Business – Curate Your Subscriptions

Do you ever feel like your inbox is out of control? Perhaps you even have more than one out of control inbox. Do you find yourself getting vapor-locked from information overload? Do you consider the phrase “inbox zero” and feel like it’s as achievable as driving to the moon?

It’s time to work on that. An uncurated collection isn’t a collection it’s a hoard, and an uncurated information library isn’t a library it’s a digital fire hazard. Digital clutter can be as detrimental to your professional life as physical clutter is to your personal life.

Before you start curating, however, I recommend giving some thought to how you want to go about it. For example, I have a work e-mail that is for clients to reach me that I only access when I am at my desk working.

In general, my work e-mail is not the e-mail to which my subscriptions are sent—not even the tax-related subscriptions. My work e-mail is for clients only (and a few colleagues). That way, if I want to read tax news when I’m not working, I’m not distracted by e-mails from clients.

At the same time, my tax news goes to a different inbox. My shopping ads go somewhere else as well. While I don’t recommend having one e-mail address for each type of communications, having a few different e-mail addresses (one for “work work”, one for work reading and networking, one for personal use and shopping) can help to create boundaries that will keep you from being distracted by work when you are trying to shop and vice versa.

Once you have your various inboxes set up (or not), it’s time to take a cold hard look at all of that digital clutter. Let’s face it, most of us don’t read the consumer disclosures when we sign up for something or use a business’ website.

Whenever you provide your e-mail address to a business or use their website your e-mail address is captured. Unfortunately, not only does the business with which you are transacting use that as consent to e-mail you, often the use disclosure includes authorization for the business to sell your data (either anonomized or not) to other businesses. That’s why when you order custom business swag from one company you are not only inundated with additional e-mail from that company but you start getting e-mail solicitations from businesses selling similar or complementary products and/or services.

The same thing happens when you register for continuing education classes, enter a drawing at an expo using your business card, or join a professional organization. You start getting e-mail solicitations from that company, but if, or when, that company monetizes their e-mail list, your e-mail address is included. Yay! (Can you sense my sarcasm?)

I read once that it takes an average of nine “touches” to convince a consumer to make a purchase. Unfortunately because e-mail is relatively inexpensive and easily automated, many retail businesses use it to make all of those touches. Between regular shopping, gift shopping, professional organizations, professional news, regular news, it’s really easy for the amount of e-mail into your various inboxes to get completely overwhelming in a short period of time. That’s why it’s just good business to spend some time once or twice a year curating your subscriptions!

If the thought of trimming down your subscriptions gives you FOMO, keep reading for some tips and tactics to make sure you still get important notifications while eliminating the excess.

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Just Good Business – Review Your Office Security

Office security. It’s for you and your small business clients. Sometimes small business clients who have relatively low-tech operations don’t think they need to think much about office security. That’s just not true. Almost every small business has some level of liability exposure for theft of client information or their own information (banking, credit cards, account passwords, etc.)—even businesses that don’t consider themselves “web based” or “high tech” may have client or company proprietary information they want to keep secure and private. Often business owners focus on cyber security (and with good reason). But a good, comprehensive security plan creates a safety triangle around important information and the property that holds it. The three sides of this triangle are cyber security, physical security, and (at the base of it all) operations security. Keep reading to secure your future!

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Just Good Business – Find Your Audience

The first rule of good writing is “Know your audience.” I would argue that this rule applies to your tax practice as well. Tax professionals, it’s time to find your audience. If you want to be the best tax professional you can be, while preserving your physical and mental health, take a moment (or several) to define your ideal client. Your ideal client is your audience. Deciding which clients you want to work with will serve you well during tax season and beyond…

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Is the Residential Clean Energy Credit Worth It?

Have you ever gone into a dealership to purchase a car? It’s been a while for me, but one of the things that keeps me from vehicle shopping is just how difficult it is to ascertain the actual price of the vehicle. The salesperson wants to run a credit check and then talk to you about how much payment you can afford. They want to factor rebates and trade-in value of your existing vehicle to the payment they quote you without ever telling you what you are paying for the car. The entire negotiation often becomes about the monthly payment (regardless of the term of the loan) rather than the car’s price.

Indeed, personal finance websites almost always recommend negotiating the three aspects of your car purchase separately: the vehicle’s price, the trade-in amount for your vehicle, and the financing. Otherwise, you run the risk of both buying more car than you can afford and being upside down in the loan (owing more on the vehicle than the vehicle is worth) shortly after you make the purchase.

What does this have to do with the expansion of the Residential Clean Energy Credit, you ask? More than you might think. My husband, after talking to a neighbor, recently decided to start shopping for solar panel systems with the idea of saving money on (or largely eliminating) our monthly power bills. What followed was a crash course in residential solar energy sales and the associated economics.

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Famous Bad Citizens and the Code That Caught Them – Al Capone

At its peak, Alphonse (Al) Capone’s criminal empire was worth approximately $1.3 billion when adjusted for inflation. On June 5, 1931, Capone was indicted on multiple counts of income tax evasion. At the time the maximum penalty for his offenses was 32 years in jail and $80,000 in fines (almost $1.6M in inflation adjusted dollars). The prosecution in Capone’s case “documented Capone’s lavish spending, evidence of a colossal income. The government also submitted proof that Capone was aware of his obligation to pay federal income tax but failed to do so.”

Click here to keep reading about this fascinating case…

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Facts, Circumstances, and Forever Stamps

The price of a forever stamp increased from $0.58 to $0.63 on January 1, 2023. A tax pro posted this fact as a public service announcement on Facebook. Of course, tax pros being tax pros, someone chimed in, “Do I have to recognize a capital gain upon disposition of my forever stamp?” And of course, someone (me) felt obliged to answer, “It depends.” A direct message followed this bit of tax drollery on Twitter that says, “In theory, if I’m holding stamps as an investment, they would be a capital asset.” And so it begins…

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Home Vacation Deductions

End of Summer Tax Savings: Summer Home Rentals and Summer Jobs for the Kids

Considering hiring your kids to work in your business or renting property you own to your business to save money on taxes? Both of these strategies can work (and work well), but often those promoting them (the mainstream media, social media, etc.) hold forth heavily on the benefits of the strategies without considering the nuances and fine print that can end up costing money rather than saving it if you end up on the bad side of an audit.

Keep reading for how to maximize tax savings on summer homes and summer jobs without getting burned.

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Don’t Let Estate Taxes Force Your Family Business into Liquidation

My mom knew she was going to die. And she knew it would be sooner rather than later. Unfortunately, it was much sooner than she expected. She had time to put her personal affairs in order but ran out of time for figuring out succession planning for her business. Transitioning her sole-shareholder S-corporation shares over to me upon her death should have been straightforward. It wasn’t. But that’s a subject for another article.

Transitioning a family business upon the death of an owner or a significant stakeholder (partner or shareholder) is never easy. Having to grapple with how to pay estate taxes on a closely held business can add complexity and stress to an already fraught process.

With proper planning, however, family and other closely held businesses can avoid having to liquidate assets or sell shares or partnership interests to pay estate taxes. Insurance arrangements, operating agreements that include buy-sell provisions, and gifting strategies can all help to ensure a family business remains in the family and can pay any associated estate taxes. But what happens in the absence of proper planning? What happens when beneficiaries inherit a business they would like to keep family owned or closely held, but which is not liquid enough to pay the associated estate taxes within the required nine months? IRC Section 6166 can come to the rescue.

Continue reading to learn more.

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Deducting Business Meals and Entertainment: The good, the bad, the very recently changed

“Say dog.” My dad once told me that a friend paid for his lunch and said, “Say dog, then I can write this off.” She bred show dogs. File that under “nope.” That is not how the meals and entertainment (M&E) deduction works. Not even before the Tax Cuts and Jobs Act (TCJA) changed the rules.

The deduction for M&E is a favorite of many of our clients and rightfully so. Nevertheless, it can be a fraught area if taxpayers and their advisors don’t have a comprehensive understanding of how the rules for deducting expenses apply across the many different scenarios in which our clients are likely to apply them. The IRS issued the final regulations for deducting M&E expenses under Internal Revenue Code (IRC) § 274 on October 9, 2020. It made some additional, short-term adjustments when the Consolidated Appropriations Act (CAA) became law on December 27, 2020. Here is an overview of the new regulations, how to use them to your clients’ benefit, and how to avoid the most common pitfalls.

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Beyond The Returns – Live Webinar Series Event!

Tax season is always demanding. But what comes after? As a dedicated tax professional, it’s crucial to continually enhance your practice and adapt to an ever-changing landscape.

Introducing the Beyond the Returns Series – an in-depth suite of four live webinars designed to transform your firm’s future.

Led by industry veterans, Amber Gray-Fenner, EA, NTPI Fellow, USTCP and Matt Metras, EA, this series promises actionable insights to ensure you’re well-prepared for the 2024 filing season and the years to come.

Don’t miss out on this opportunity to redefine and rejuvenate your tax practice.

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Benefit Plans Without Breaking the Bank: Save Tax by Being Unfair

Let’s face it, many small businesses would love to offer retirement and healthcare benefits to their employees, especially owner employees. In addition to the obvious benefits (healthcare coverage and tax-deferred retirement savings), providing healthcare and retirement benefits to owner employees through a business can shift non- or partially deductible personal expenses to fully tax-deductible business expenses. Even for non-owner employees, these types of benefits are a great way to provide additional compensation without incurring additional payroll taxes. As with everything tax and business related, however, there are rules and employers must be careful to follow them, especially when it comes to what types of benefit plans are offered and to whom.

Providing healthcare and retirement benefits is expensive which is why many small business owners would like to be able to limit who receives them. But if you think providing benefits is expensive not paying attention to the rules for providing them can be even more expensive. To ensure your clients’ benefits plans remain tax deductible, it is important to understand the federal, state, and local labor and tax laws that affect the plans. This article provides an overview of what small employers and their advisors need to consider when evaluating potential benefits options and takes a more in-depth look at the Internal Revenue Code (IRC) and the Employee Retirement Income Security Act (ERISA) non-discrimination provisions that are most likely to affect small employers.

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Be Careful When Using a C Corp to Avoid the Hobby Loss Rules

Starting a business is hard. Running a business is hard. And often, it isn’t profitable either – at least not right away.

As if losing your money isn’t enough torture, it can get worse. If your business is not profitable and remains that way for a while the IRS can reclassify it as a hobby. This is really bad because while you still have to pay tax on your hobby income, you can’t deduct any of the expenses. Ouch!

One strategy around this is to reorganize as a C corporation (since code section 183 doesn’t apply to them). However, if you’re thinking about using this to deduct expenses from your hobby, be careful! A taxpayer, a courtroom, and a whole lotta cats (explanation later) might change your mind.

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Avoiding the Repayment Cliff: Mitigating the Effects of Miscalculating the Advance Premium Tax Credit

The premium tax credit (PTC) is a refundable credit that is available to certain individuals “whose household income for the taxable year equals or exceeds 100%, but does not exceed 400% of an amount equal to the poverty line for a family of the size involved.” In other words, it’s a refundable tax credit that specifically subsidizes the cost of insurance purchased on a health care marketplace for individuals who are over the federal poverty level (FPL), but not by 400 percent or more.

This credit is available as an advance paid directly to the marketplace for qualifying taxpayers who cannot afford (or do not wish) to pay their full monthly premium out of pocket. The amount of the credit is calculated based on estimated annual household income.

When taxpayers receive more advance credit than they are entitled to, they must repay the excess. So, the consequences for an intentional or inadvertent underestimation of annual income can be severe. What follows is an overview of how the credit works and describes strategies for reducing the amount of advance premium tax credit (APTC) the taxpayer must repay both immediately and after the fact.

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Electric Vehicles Credits - Worth It

Are Electric Vehicle Credits Really Worth It? Spoiler Alert: It Depends!

It happens all the time. A client comes in with the receipt for a new hybrid or electric vehicle and is expecting a huge tax credit to offset some of the purchase expense. It’s a fact that hybrid and electric vehicles cost more (some estimates say an average of $19K more) than their internal combustion engine (ICE) based counterparts. And, despite the fact that hybrids and fully electric vehicles continue to gain market share, it has continued to be difficult to quantify exactly how much fuel and maintenance cost savings offset the larger price tag.

Often, the time span for offsetting the difference in purchase price is much longer than many taxpayers want to keep their cars. Taxpayers hope tax credits will help them to recoup the difference in purchase price more quickly than fuel and maintenance cost savings. Do they? Are electric vehicle tax credits really worth it? Well, it depends.

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Any Port in The Storm – Tax Strategies for Boat Owners (Part 2 of 2)

Ever thought of using a recreational vehicle like a boat to lower your taxes? Yes, it’s possible using the right strategies, and there’s no time like the present to make that happen.
Even more than pre-pandemic taxpayers may be considering buying their own island. Those for whom buying an actual island is beyond the budget may be considering buying a boat or an RV for use as a residence, an office, or both.
Whatever the type of use, there are tax strategies available for boat owners if they meet the requirements. As with any tax strategy it is important to have a full understanding of the requirements to ensure the deduction is legal and to ensure the taxpayer can substantiate the deduction should the tax authorities examine the return.
This is the first of two articles discussing the tax strategies available to boat owners. Part 1 focuses on using a boat as a residence, but if that doesn’t meet your needs, stay tuned because Part 2 will cover boats for business use (including as a home office). Why not consider both options and see how your tax savings can help fund your floating condo? Keep reading to learn more.

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Any Port in the Storm – Tax Strategies for Boat Owners (Part 1 of 2)

Ever thought of using a recreational vehicle like a boat to lower your taxes? Yes, it’s possible using the right strategies, and there’s no time like the present to make that happen.
Even more than pre-pandemic taxpayers may be considering buying their own island. Those for whom buying an actual island is beyond the budget may be considering buying a boat or an RV for use as a residence, an office, or both.
Whatever the type of use, there are tax strategies available for boat owners if they meet the requirements. As with any tax strategy it is important to have a full understanding of the requirements to ensure the deduction is legal and to ensure the taxpayer can substantiate the deduction should the tax authorities examine the return.
This is the first of two articles discussing the tax strategies available to boat owners. Part 1 focuses on using a boat as a residence, but if that doesn’t meet your needs, stay tuned because Part 2 will cover boats for business use (including as a home office). Why not consider both options and see how your tax savings can help fund your floating condo? Keep reading to learn more.

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An Alphabet Soup of Confusion: LLCs, BOI, and UPL

By now I hope that all tax professionals have heard of the FinCEN requirement for certain entities to report beneficial ownership information starting in 2024. The requirement is causing confusion because tax and accounting professionals feel that this could be an opportunity to either add value to an existing engagement, could be a new revenue stream, or could be a huge potential for liability. What follows is a brief review of the law and the requirements, an analysis of the main issues, and some recommendations for practitioners wondering how to help their clients while limiting their professional liability.

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All About the Augusta Rule – One of the Tax Code’s Best and Easiest Income “Loopholes”

Do you have homes in destination spots? Places where people flock during specific times of the year? Mardi Gras? Spring break? Sports championships or events? Maybe you own a home in places commonly used as film locations? For example, Albuquerque, New Mexico, is often the site for movie and television productions, and it hosts the Albuquerque International Balloon Fiesta every year (excluding global pandemics, obviously). The 10-day long event hosts well over 100,000 visitors to the city each year. But this article isn’t about Albuquerque tourism, it’s about the easiest tax-free money you will ever make.

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How to Deal with Huge Tax Debt

The only thing scarier than owing Uncle Sam a lot in taxes is being unable to pay the bill. Luckily, the Internal Revenue Service has ways for you to whittle what you owe. Just make sure which method works for you, depending on such factors as the size of your tax debt and what you can afford to pay and when. Don’t panic. Here’s how individual taxpayers can proceed – and what to watch out for.

Client Retention Strategies for Accountants: Building Long-Term Relationships

Client acquisition is crucial for business growth in the fast-paced accounting world. However, retaining existing clients is equally important, if not more so. Servicing long-term client relationships is a testament to your firm’s reliability and is critical to sustained success. My first client is still with me, now more than seven years. Our relationship has grown and changed over time but has also strengthened.

Loyalty and commitment are two of my core values. I’m always looking to provide value to my prospects and clients to attract and retain them long-term. However, some clients do not fit those values, and I have decided to forgo working with them.

I believe that attracting and retaining the right clients starts with your mission, vision, and core values. However, it is also essential to have effective client retention strategies to ensure clients remain loyal and satisfied for the long haul.

Health Savings Accounts vs Flexible Spending Accounts

With the rising cost of healthcare, our clients are looking to save money where they can, especially if they can save money on their healthcare costs and taxes at the same time. As their trusted advisor, you can offer them a basic understanding of what savings tools are available to your clients. Some of the tools available will come in handy if there is a minor unexpected tax bill this spring.

That is why today we’re going to look at the triple tax advantaged health savings account (HSA) and the health flexible spending account (FSA). We’ll look at what they are, who is eligible to open one, and how they can save your clients money each year.



  • Avoiding Passive Loss Limitations Through Short-term and Alternative Rentals

    Short-term rentals like AirBnb are becoming increasingly popular with taxpayers who invest in real estate. For many taxpayers, the appeal of these properties is the flexibility and cash flow potential. However, there may be an overlooked third tax benefit. In many situations these short-term rentals may not qualify as a rental activity to the IRS, and that may offer a big tax break. While many rental activities generate losses, this can leave taxpayers facing the frustrations of not always getting to deduct those losses right away due to the passive activity limitations.

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    How Business Owners Can Boost Income by Avoiding the $10,000 SALT Cap

    Taxpayers have been whipsawed by confusing rules for the $10,000 limit on deducting state and local taxes (SALT), the most politically charged piece of the Tax Cuts and Jobs Act (TCJA) of 2017. The cap has caused nearly 11 million individuals to lose an annual deduction worth $323 billion. But many owners of private businesses known as passthroughs can avert that financial pain. If you own your company and thus report your business income on your personal federal income tax return, here’s what you need to know.

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    Millions of taxpayers in the United States are using crowdfunding websites like GoFundMe and Kickstarter to raise money for important needs, such as paying medical bills, paying legal fees, or funding a new business venture. Both the IRS and the courts have been surprisingly silent on the tax consequences of crowdfunding platforms. The good news is that established tax law provides a clear road map for answering most tax questions created by raising money from a crowdfunding website. By knowing these rules, taxpayers can use crowdfunding to raise cash and minimize their overall tax exposure.

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    My Client Stuck with a Mistaken C Corporation Election?

    My client formed three limited liability companies (LLCs) to hold his rental properties. Without consulting me, he filed Form 8832, Entity Classification Election, to elect C corporation treatment, effective January 1, 2020, for these LLCs. I want the LLCs to be disregarded entities, which is the most tax-efficient structure for his situation. What is the best way to undo these elections?

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    Quick Guide to Claiming Work-From-Home COVID-19 Expenses to Reduce Your Tax Bill

    This information is particularly important if you are the owner/shareholder of your own corporation – C or S corp. You can set up payroll and designate tax-free reimbursements for you to be working at home – as well other tax-free money for you and for your employees. (We will discuss employees momentarily. Yes, it’s essential.) If being an employee is your main source of income – watch out! The short answer to employees claiming an office in home deduction this year is... There is no deduction!

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    Five Tax Reduction Strategies for the Casual Cryptocurrency Owner

    With so many people looking for more ways to make money outside their 9 to 5 jobs, many are turning to money making methods using technology including trading in cryptocurrency. For tax purposes, the IRS considers cryptocurrencies property, not as currency. Just like other property types, stocks, investments, or real estate, when you sell, swap, or otherwise dispose of your cryptocurrency for more or less than you acquired it for, you incur a tax reporting obligation. As an example, there would be a $1,000 capital gain if 0.1 bitcoin is bought for $2,000 in June of 2020 and then sold for $3,000 two months later. This profit must be reported on the tax return and a certain amount of tax is due on the gain, depending on the tax bracket of the taxpayer. In this example, the gain would be short term requiring the profit to be taxed at the filer’s ordinary tax rate. These rates range anywhere from 0-37%.

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    Extra Taxes on S Corporation Distribution?

    My client plans to take about $15,000 in distributions in excess of his basis from his S corporation construction business. I know this generates tax for him. He’s in the 32 percent tax bracket and single. Does he also have to pay the 3.8 percent net investment income tax and the 0.9 percent additional Medicare tax on this amount? Is there a way for him to avoid taxes on this amount?

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    Reduce Taxable Income Up to $25,000 with Passive Rental Losses

    You have likely heard that owning rental real estate provides great tax benefits. This is true for a multitude of reasons, but there’s one benefit that is arguably the best of the bunch: The Small Taxpayer Allowance for Deducting Passive Rental Losses. Based on average household income levels, more than three-quarters of taxpayers can potentially qualify for this fantastic tax benefit that offers taxable income reduction of up to $25,000.

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