CURRENT EDITION

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.
READ MORE2025 Winter Education Series Event Calendar
Think Outside the Tax Box proudly presents the 2025 Winter Education Series! This October through December, we are bringing our loyal subscribers five webinars featuring some of the brightest minds in tax. Each high quality webinar is filled with engaging content, actionable insights for your clients, and they all come with continuing education credits for those who qualify. All of this is included in your regular subscription! Check out what we've got in store for you!
Read MoreIs It Time to Hire in Your Firm?
After my second busy season as a solo practitioner, I made a terrible mistake within my firm. I hired my first employee. As a matter of fact, I hired someone who also had tax and accounting experience. You may be thinking, “What? Hiring is the solution if you were feeling overwhelmed.” That is true, if you are assuming that I had the proper systems in place. The mistake I made was hiring an employee before I was ready. The money was there and ready. The work was there and ready. It only took a few weeks to realize that I didn’t have a capacity issue. I had a systems and processes issue. I am not suggesting that you should work yourself to full capacity, absolutely not. I am suggesting that before you attempt to pass along a task to someone else or put in place automation that you have a written-out process.
Read MoreYou Don’t Need a Bigger Stack — You Need a Better Portfolio
In every tax Facebook group or conference session, there's always that one pro excitedly talking about the latest app they've added to their "tech stack." But here's the dirty little secret: most of us aren't running integrated tech stacks. We're juggling a mix of disconnected tools that may or may not play nicely together. Let's stop pretending we're all building perfectly integrated ecosystems. What we really need is a tech portfolio—a curated collection of tools that serve our actual needs, reflect how we really work, and support the kind of client experience we want to deliver. A portfolio recognizes reality: tools don’t have to talk to each other perfectly. They just need to work for you. So let’s explore how to build a smart, efficient, and secure tech portfolio that helps you thrive whether you’re a solo professional or managing a growing team.
Read MoreTracking and Measuring Your Business Development Efforts: KPIs for CPAs
As CPAs, we were trained to work with precision, accuracy, and strategy in everything we do. However, business development has not been part of our standard training; therefore, many accounting professionals not only struggle with business development tactics but also shy away from tracking and measuring the impact of their efforts. But here's the truth: Just as we track and measure other financial data, it is essential to measure business development efforts in order to improve. You can unlock significant growth in your firm by understanding which key performance indicators (KPIs) to track, how you manage your practice, how you acquire new clients, and how to increase your revenue.
Read MoreAre There Tax Consequences of The GENIUS Act? It Depends!
The Guiding and Establishing National Innovation for U.S. Stablecoins Act became Law on July 18, 2025. It “establishes a regulatory framework for payment stablecoins,” which are defined in the legislation as “digital assets which an issuer must redeem for a fixed value.”
Read MoreQualified Opportunity Zones After the One Big Beautiful Bill Act: What’s Changed and What It Means for Real Estate Investors
On July 4, 2025, the One Big Beautiful Bill Act (OBBBA) became law, representing the most significant reform of the QOZ program since its inception. It made the program permanent, tightened eligibility rules, introduced a rural-focused investment vehicle, and imposed robust reporting requirements. For tax professionals and investors, understanding these changes isn’t just about compliance – it’s also about strategy.
Read MoreVibe Preparing: Ignoring Partnership Agreement Impacts on K1s
Nothing derails a busy season schedule like being forwarded emails from client’s investors asking “are you sure the loss is allocated correctly?” It can expose a weakness in technical expertise – especially when it’s a partnership K1. Whether the operating agreement includes Safe Harbor or Target Capital allocations is one of the most important places to start for a preparer. And knowing these basics can be the difference between a confident reply or a lost week.
Read MoreDeducting Gambling Losses: Part 2: Sessions Method
Recently I polled my peers on a social media platform dedicated to tax professionals. My hope was to find a resource for tax rules on a state level for handling gambling sessions. I knew it would be an uphill battle to get the information needed for a comprehensive guide state-by-state. What surprised me was the response. A large percentage of tax professionals were either unaware of gambling sessions or were unclear on how gambling sessions were handled in their state. Since gambling sessions might be the best way to reduce taxes on gambling wins, a lot of money might be left on the table with clients paying the price. Even if the state a tax professional prepares most tax returns for does not have gambling, the likelihood a client travels to a state that does, gambles, and wins is high.
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CURRENT EDITION

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.







