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New tax reduction strategies carefully explained and exhaustively researched every two weeks. Receive breaking news updates on tax law changes. Members only monthly AMA with TOTTB.tax.
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FEATURED CONTENT
Side Hustles and Tax Tussles: Tax in the Gig and Share Economy Part One
I can recall looking for a part time job in local newspapers when I was in high school. Sometimes a friend and I would ride around with our $2.29 per gallon gas looking for places that were hiring. Facebook was gaining popularity but not for job posting. So, searching for jobs on my phone via an app was unimaginable. Advances in technology have changed the way that we do things in the world. Everything an individual needs to find a job is right at their fingertips. There are more opportunities to find gigs and be your own boss if that’s what one desires. There’s no question that the way people find ways to earn income has changed. What has not changed is the fact that the IRS wants their share of the income earned. But how do we apply the tax code to these new ways that taxpayers are earning money? We are going to break that down in this three-part series. Whether your client is doing odd jobs on an app like TaskRabbit, driving for Lyft, renting out their home or car, you will know how to guide them. This is what we are going to cover today with a focus on rideshare, delivery, and other service gigs.
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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.
SIMPLIFIED TAX STRATEGIES &
PRACTICAL IMPLEMENTATION
Think Outside the Tax Box provides tax reduction strategies along with practical
implementation advice in order to reduce your clients’ federal tax bill with ease.
