CURRENT EDITION

Lessons Learned from the Tax Court: What’s at Stake?
Astute readers of this publication may recognize that I frequently write on Cryptocurrency and also on Tax Court cases. It feels like Christmas to me to be able to write about a tax court case about crypto. This is only the Third Tax court case to even mention crypto, and the first to look at the underlying principles of taxation. (The other two were about including crypto assets in a CDP hearing and a frivolous tax protester argument). Today’s case, Paschall v. Commissioner, is about the taxation of staking income.
READ MOREThe Hidden Benefits of Private Placement Life Insurance (PPLI) for High-Net-Worth Families
For wealthy families, the world of finance can feel like a high-stakes chess game. With increasing state and federal income tax rates, new tax laws on the horizon, and the complexities of private investments like hedge funds, finding ways to grow and transfer wealth efficiently is more important than ever. Enter life insurance—a tool not just for its traditional role of providing death benefits but as a strategic ally in tax-efficient wealth management. In particular, Private Placement Life Insurance (PPLI) offers unique advantages that make it a worthy consideration for those with sophisticated financial needs and significant liquidity.
Read MoreThe Cryptocurrency Basis Day of Reckoning is Upon Us
Late on a Friday afternoon at the end of June 2024, the IRS dropped nearly 400 pages of new Digital Asset (née Cryptocurrency) Guidance. Most of it related to the forthcoming form 1099-DA. Along with the massive tome of terrible bedside reading, the service also published two new Notices and a Revenue Procedure. The Notices were about boring stuff, like temporary penalty abatement for backup withholding on digital asset transactions. This Revenue Procedure, however, will impact nearly every taxpayer that owned crypto prior to January 1, 2025. This procedure, RP 2024-28, has gone largely unnoticed thus far. On the surface, it seems like a godsend to taxpayers. Below the surface though, it is a ticking time bomb.
Read MoreReflecting On Syndicated Conservation Easements
In late June, IRS announced it would be mailing out a time-limited settlement offer that would allow taxpayers who are haunted by an investment in a syndicated conservation easement to settle. As I write this, the terms of the settlement have leaked. They strike me as overly generous. It does seem that the syndicated easement campaign of the IRS is coming to a close.
Read MoreDo Clients Owe Income Tax in Different States?
No client’s ever happy about having to pay state income tax in addition to federal, but at least in the past that chore was straightforward: Make money in a state, probably the one where you live and work, and you owe tax on what you made if that state has an income tax. Enter the computer and the fax machine, later the modem, email and Zoom. Then enter the pandemic and widespread remote work from home that’s largely lingered after Covid faded. Cap it off with the new maneuver of moving from a high-tax state to a low-tax one but not completely severing all former work and life connections. It is any surprise, really, that states would try to squeeze tax revenue out of that using regulations still unchanged from the past? And for punishing what that state suddenly thinks are tax cheats? Do you have a client a state might be interested in? How many states? And how do you actually know?
Read More2024 Endless Summer Education BONUS Series Calendar
Our 2024 SUMMER EDUCATION SERIES was such a big hit that we've decided to bring you two BONUS webinars! Every webinar comes with free continuing education credits for those who qualify! Keep reading for more details...
Read MoreTax Principles Analysis of the Celsius Bankruptcy
In Matt Metras’ excellent article on tax reporting for clients who receive settlements from the Celsius bankruptcy, he says “It’s unclear if this section could apply to digital asset bankruptcies for a variety of reasons outside the scope of this article.” Matt provides an example of the IRS’ preferred method of accounting for settlement proceeds as published on the Taxpayer Advocate’s website. Matt also notes that the TAS tax tip lacks any citations to substantial authority. It may or may not be taxpayer friendly. The articles published by many cryptocurrency exchanges are also citation free and, after a cursory review, seem geared in a larger sense toward helping exchange users account for the settlement accurately on the exchange itself. In this article, I would like to look at the forest of tax law principles that the Celsius bankruptcy settlement puts into play rather than any specific tax reporting tree. Welcome to the jungle.
Read MoreTax Trends in M&A and What it Means for Your Clients
M&A activity during Q1 2024 has experienced the strongest start in two years, with over $549B in global deal volumes, representing a 28% increase from Q1 of 2023. However, gone are the days of easy financing and 0% interest rates – the federal funds rate is currently between 5.25% - 5.50%, forcing taxpayers to rethink their deal structures and consider certain tax cost optimizing strategies, which are discussed in this article.
Read MoreLeveraging Video Marketing: Accountants Captivate Clients through Visual Storytelling
Digital marketing is always changing, and as accountants, we must find innovative ways to connect with our prospects and clients. Enter video marketing—a dynamic tool revolutionizing how financial professionals communicate complex concepts, build trust, and cultivate lasting client relationships. In this article, I will expand on the key benefits of video content, its transformative power for accountants, practical implementation tips, and strategies for measuring impact.
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CURRENT EDITION

Lessons Learned from the Tax Court: What’s at Stake?
Astute readers of this publication may recognize that I frequently write on Cryptocurrency and also on Tax Court cases. It feels like Christmas to me to be able to write about a tax court case about crypto. This is only the Third Tax court case to even mention crypto, and the first to look at the underlying principles of taxation. (The other two were about including crypto assets in a CDP hearing and a frivolous tax protester argument). Today’s case, Paschall v. Commissioner, is about the taxation of staking income.

What’s New With Hobby Loss: Recent Developments in Section 183
Recent developments in the Section 183 (Hobby loss) area have not led me to change my basic conclusions. Taxpayers who have a sincere objective of ultimately making a profit should not hesitate to claim losses from the underlying activities. That is so even if you believe that profits are improbable. It is critical that they meet the standard of behaving in a businesslike manner. The other regulatory factors should not be ignored, but often there is not that much you can do about them. Reilly’s 18th Law of Tax Planning – Honest objective trumps realistic expectation.

The Art of Income Shifting: Powerful Planning Strategies That Stand Up to Scrutiny
Income shifting strategies address taxation at its most fundamental level by directing income to taxpayers in lower brackets or with offsetting deductions. Unlike many tax strategies that merely time recognition or enhance deductions, effective income shifting can permanently reduce the tax burden on a given dollar of income—often creating tax savings that compound year after year. In this article, we’ll explore systematic approaches to income shifting that create extraordinary value for clients while maintaining impeccable compliance.








