Client Alert
Trust Issues: Don’t Try to Save Your Way to the Trust Fund Recovery Penalty
When people reach out to me about reducing their tax bill, there are two things that they bring up. The first is starting an LLC, and the second is converting their business to an S-Corp. When I ask why they think an S-Corp will help, the common knee jerk reaction response is to eliminate self-employment tax. It is true that their net income will no longer be subject to self- employment tax and neither will their distributions. However, what they fail to learn in their S-Corp online class from YouTube university is that they need to be on payroll if they are working in the business. Not only that, but they also need to receive reasonable compensation while on payroll. So, what happens if they go a year or two without being on payroll before they find this out? The TFRP is the biggest ouch a business owner can face and threatens to close businesses each year. It's the penalty that business owners pay for stealing from their employees and the IRS. To better understand it, let's look at what the trust fund is, how the IRS calculates the penalty, and who is responsible.
Read MoreCharitable Contributions From Your IRA: Tips and Traps
A really neat thing happens when you turn 70 and ½. Your IRAs essentially turn into donor advised funds if you don’t need all the money in them to make ends meet. Rather than withdraw money from your IRA to make charitable contributions, you can make them out of the IRA. So instead of an itemized deduction, you get an exclusion from adjusted gross income. For some people this might be a wash, but for most it probably isn’t. Besides the possibility of not being over the standard deduction threshold, there are a host of computations and thresholds that involve AGI. There are some things you need to watch out for, but first let’s go over the basics.
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Tax Loss Harvesting with Cryptocurrency
In the Fall of 2025, Bitcoin reached an all-time high of over $120,000. Since then, it fell over 40% to under $70,000 in the first quarter of 2026, before slightly recovering, currently resting around $75,000 as of this writing. With the steep drop in the price of Bitcoin and other cryptocurrencies, a common question from taxpayers is whether they can use the current losses to offset their other income. Large investors and professionals such as Grant Cardone and Shehan Chandrasekera (Head of Tax Strategy at Cointracker) have suggested that cryptocurrency can be sold and bought back immediately to claim the tax benefits. As with most things, the answer to this is not as simple as they portray, and many commentators, influencers, and sometimes professionals, miss the intricacies of cryptocurrency taxation.

The Kwong Tsunami: Why Form 843 Claims Could Soon Flood Your Practice
The buzz around the Kwong v. United States decision is quickly turning into something very real for practitioners: potentially a wave of Form 843 claims tied to COVID-era penalties and interest. With voices like Frank Agostino pushing for action, the message is clear: dig into client transcripts and don’t sit this one out, even though the outcome is still being litigated.

The Strategic Tax Analysis Process: Your Systematic Approach
Early in my career as a tax professional, I thought identifying strategic opportunities was primarily a function of technical knowledge. If I just knew enough tax law, I assumed the right strategies would naturally reveal themselves when reviewing a client’s situation. This assumption led to a haphazard approach where I might spot a planning opportunity for one client but completely miss an identical opportunity for another simply because I wasn’t methodically looking for it. This inconsistent approach changed when, leaning on my training as an instrument rated pilot, it occurred to me that I should be following a structured process that assures that I won’t miss any opportunities. That observation transformed my practice. I realized that identifying strategic opportunities isn’t just about what you know—it’s about how systematically you apply that knowledge. Even the most knowledgeable tax professional will miss opportunities without a structured methodology for uncovering them. In this article, I’ll share the systematic strategic analysis process I’ve developed over three decades of tax practice. This methodology doesn’t replace technical knowledge—it magnifies its impact by ensuring you consistently identify opportunities across diverse client situations.


