Loopholes Archives - Think Outside the Tax Box

Loopholes

By Ted Stotzer

Selected Techniques to Monetize Tax Attributes

In the prior article "Tax Trends in M&A and What It Means for Your Clients," we had discussed certain techniques to, e.g., maximize net operating loss (“NOL”) and interest expense deduction utilization in the context of M&A transactions. This article examines certain additional strategies to monetize expiring, latent, or otherwise disallowed tax attributes.

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Do Those Tricks Really Work?

On the website for Axium Wealth, Charles Dombek tells us that: “Most CPAs are historians that tell their clients how much they make, how much they owe, when and where to file their taxes, and oftentimes how to write large checks at the last minute when you least expect.” When it comes to Axium, though: “We help clients recover dollars they unnecessarily pay in State and Federal income taxes.” Axium also helps clients diversify capital into off-market passive real estate and alternative investments. Before Axium, there was The Optimal-Financial Group LLC. Of course many of the readers of Think Outside The Tax Box are CPAs, or EAs or others who both help their clients be compliant and advise on ways to minimize their liability. When I was practicing I would call the things I might suggest my “bag of tricks.”

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TAX COURT ROUNDUP – November 2024

It's been said that the United States Tax Court is "a vital cog in the financial machinery of the country," and October proved that point yet again.

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Editor’s Pick: The Future of Digital Product Taxation—What Tax Professionals Need to Know

As states increasingly focus on taxing digital products, tax professionals need to be aware of how these changes will affect their clients and businesses. The Multistate Tax Commission (MTC) is at the forefront of efforts to create more uniform approaches to taxing digital goods, and their proposals could have far-reaching consequences for compliance, pricing strategies, and audit risks. Here’s a breakdown of the major proposals under consideration and how they will impact sellers of digital products—and the tax professionals advising them.

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Striking a Balance: Pitching to the Umpires of Tax Law – Understanding US Tax Court Judges through the Art of Baseball Analogies

In this fascinatingly original article, we explore the striking parallels between America's pastime and the high-stakes world of tax litigation. Prepare to be surprised as we reveal the hidden connections between the umpires of the diamond and the judges of the Tax Court. From the precise strike zones of regular judges to the veteran expertise of senior judges, and the specialized skills of special trial judges, you'll gain a newfound appreciation for the officials who keep the game of tax law fair and balanced.

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Editor’s Pick: Tax Planner Faces Malpractice Claims Over Decades-Old Tax Advice—What Went Wrong?

In a case that every tax professional should take note of, the prominent law firm Sidley Austin LLP finds itself defending against claims that it provided faulty tax advice over two decades ago, leading to massive IRS liabilities for a family. The plaintiffs, the Cáceres family, are seeking to recover $7 million after settling with the IRS, claiming Sidley's advice on a complex asset liquidation set them up for disaster. The kicker? The lawsuit was filed over 25 years after the advice was given. So, how are the plaintiffs still able to pursue the case? It all boils down to a claim of fraud—and how that could toll the statute of limitations.

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2024 Winter Education Series Event

Summer may have ended but the education never does here at Think Outside the Tax Box! Join us this winter for our brand-new series of live webinar events spotlighting an intriguing mix of topics all focused on improving you, your business, and your ability to better serve your clients! All of these live events are included FREE with your Basic or Professional subscription and include Continue Education Credits for those who qualify! Winter time is a great time to be part of the Think Outside the Tax Box community! Here are the details of what we have in store for you…

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Tax Policy and Reform Considerations for the Next President and 119th Congress

Something we never have a shortage of are proposals to change our tax systems. When it’s election time, we hear even more proposals, as well as how various parts of our tax system are flawed, usually due to actions or inactions of the opposing party. We also hear lots of incomplete statements, promises of tax changes too costly to be enacted, and ideas that will be replaced by the time the winner gets down to crafting a real set of tax and budget proposals. This article describes some of the tax proposals of the two presidential candidates along with suggestions on how we should analyze them against principles supporting effective tax systems, with highlights of some important facts seemingly missing from current tax discussions. These proposals are also relevant to members of Congress as to whether they support any of them and how they align with tax changes that the member would like to see enacted.

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TAX COURT ROUNDUP – October 2024

Much of what happens in Tax Court is run-of-the-mill. Once the tax general practitioner learns the jurisdictional limits and procedural moguls, s/he can advise clients whether to spend the sixty bucks and the certified mail fees when TAS, Examination or Appeals can't deliver an acceptable result. Following the Court's orders and opinions for a while should do that. I try to present the less-than-usual, below-radar points for generalists and specialists.

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