Business Strategies Archives - Think Outside the Tax Box

Business Strategies

By Peter J Reilly CPA

How Things Go Criminal

If you were to ask most taxpayers what they worry about when it comes to their tax returns, they might say an unexpectedly high tax liability or even a late penalty. Next to none will worry they are at risk for criminal prosecution. There is a sound reason for this. In the fiscal year ending September 30, 2021, taxpayers filed over 261,000,000 tax returns. During that same period, IRS Criminal Investigation (CI) initiated only 2,581 investigations—a paltry 0.00098% of all tax returns filed. While CI entanglements are not a common experience, there are still lessons to be learned from looking at how things can go awry.

So what types of scenarios have resulted in criminal investigations by the IRS, and what can this teach the everyday taxpayer? First of all, working with an expert, such as a Certified Tax Planner, will help you better understand what is permissible by the IRS and reassure you that your returns are fraud-free. For a few tips on what not to do, read the cases below and review our key takeaways for each one.


The 1099 Nightmare

My attitude toward 1099 compliance changed radically about fifteen years ago. The type of 1099 compliance I am talking about is for business to business services. If you are running a bank or a brokerage house, this will not be any help. I was a partner in a regional firm and frankly I never gave 1099 compliance much thought until I was called in to consult on an audit. Then I got this really scary wake-up call...

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Client Alert

Reporting Cannabis on a Federal Return: A Very Basic Primer

You can find new cannabis dispensaries or head shops on every corner in my neighborhood. But purchase and sale of marijuana has not been legalized on the federal level. What’s an ethical tax professional to do, when your client walks in with the news that they’ve started a cannabis business in your state? Read on to find out!

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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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An Unconventional Way to Get More Help

Stories about accounting and tax firms having trouble finding help seem to be popping up everywhere . Also, I pick up a lot of chatter about it on #TaxTwitter. It has even invaded my home. The firm that I consult for occasionally has recruited my covivant Evie as a remote preparer. After we withdrew from the boutique practice that capped our careers, she kept her family and friends freebie 1040 practice. Even the freebie practice has grown as the first of ten grandchildren got her first W-2 last year. So when my high school friend called me and told me that his 25 year old son who had gone from a bachelors in something or other to a series of low level food service jobs was contemplating a masters in accounting, I was enthusiastic. For a long time I have held the view that accounting probably gives a young person the best bang for their educational buck. My buddy had a request though that intimidated me. He wanted me to tell the kid what it was like to be an accountant. When I thought about it, I realized I didn’t have much of a clue as to what it is like to be an entry level accountant. I started thinking about what it was like when I started and how irrelevant that experience seems. Nonetheless, I do have an idea that those of you scrambling to find help might want to consider and it arises from my memories of the old days.

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The Family Business and Taxes Part Two

"I have a way you can avoid paying taxes on part of your household income and get more work done in your business. Are you interested in hearing about it?" Those are two sentences most of our business clients would love to hear. You may be able to e-mail those two sentences to your client after reading this article. Who wouldn't want a way to be more efficient and reduce their tax liability? Have you had clients calling you to ask if they can save $12,000 by hiring their child? My favorite is, "I heard I can pay my child tax-free. Is that true?" I have received the call and e-mail quite a few times. There has been an uptick since 2018. The misinformation makes me cringe, but the strategy makes me smile. So today we are going to look at the strategy and answer these questions: ● How much can a taxpayer pay their child and neither one pays Federal income tax? ● Which business entities does this strategy work with? ● How can a business avoid paying payroll taxes when hiring their child?

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Client Alert

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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The Family Business and Taxes Part One

What is one thing that most business owners have in common? Why did you start your business? Many business owners I have talked to over the past decade started their entrepreneurship journey for similar reasons. Think about your clients and what reasons they have given you and see if these ring true. “I want to be in control of my time.” “I need to spend more time with my family.” “I don’t want a cap on my earning potential.” I find those to be pretty noble reasons. I haven’t come across a business owner yet that says, “I want to pay more taxes for fun.”. So as an advisor how can we help our clients have freedom, time with family, and save on taxes? One strategy is to hire family members. It can’t be any family member though, remember there is a strategy to this. I know some of you are thinking, “that sounds great!”. Then others of you are thinking, “who wants to work with their family?”. Well trust me, when saving money is the topic of discussion more people tend to listen. The least you can do is present your clients with the facts, and here they are: • The taxpayer can avoid paying certain payroll taxes by hiring a family member. • You can help them potentially drop a tax bracket while keeping the spending power in the family. • Protecting a spouse from tax debt. • Lower Federal student loan payments. To do this we have to make sure the client hires their family as employees. This whole strategy goes down the drain if the family member is a contractor that receives a 1099. Today we will focus on how to properly implement the game plan when hiring a parent or spouse.

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Client Alert

Important to Maintain Substantiation for Carryovers

If you build a mini business empire and it subsequently fails, a small consolation prize might be a net operating loss carryover that will shelter some or all of your more modest income for many years. Of course NOLs are only one among many carryovers that need tracking. In my experience the tracking often leaves much to be desired. Changes in tax preparers or even software can result in the loss of valuable carryovers. But that is not the worst of it...

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