Welcome to THINK OUTSIDE THE TAX BOX, the premier on-line publication for tax reduction information!
Here at TOTTB, we produce in-depth, easy to understand, exhaustively cited, essays on the topic of tax reduction for our subscribers! And, every two weeks, we add more articles and more features like our live webinar events, private Facebook group, downloadable “Client Alerts” and Infographics, features like our blog, Around the Tax World, an aggregator of all the news happening in the tax world!
If you aren’t a subscriber yet, please understand that this blog is a very small part of what we do. If you really want to dig in, SUBSCRIBE! (We offer a 30-day money back guarantee, you have nothing to lose!)
Around the Tax World- May 7, 2026
In The HeadlinesThe S&P 500 stalls as the war in Iran continues and the Federal Reserve meets on interest rates.
What's New In The Tax World?Republican lawmakers look to woo voters with lower capital gains taxes
State-By-State-UpdatesCalifornia’s “billionaire tax” makes it a step closer to the November ballot.
Tax Planning TipsWho can benefit most from the IRS’ free tax withholding tool?
READ MOREAround the Tax World- April 23, 2026
In The HeadlinesJust how bad is the energy crisis? Experts assess the impact of the ongoing war in Iran.
What's New In The Tax World?Despite the OBBBA tax cuts, polls show that most Americans think they are overpaying on taxes—a sentiment that could impact midterm elections
State-By-State-UpdatesHawaii’s climate cruise tax is blocked by an appeals court—what’s next?
Tax Planning TipsAs annuity sales reach record growth levels, what does this mean for tax planning?
Around the Tax World- April 9, 2026
In The HeadlinesPresident Trump projects an end to the war in Iran in April, causing stocks to rally.
What's New In The Tax World?Did you know tax assessments have an expiration date? Here’s what to know.
State-By-State-UpdatesAlaska struggles with lost revenue from properties erroneously claiming a tax exemption.
Tax Planning TipsAre your investments tax-advantaged—and if not, what needs to change?
Around the Tax World- march 25, 2026
In The HeadlinesThe Federal Reserve keeps interest rates as-is but alludes to a future cut.
What's New In The Tax World?The National Taxpayer Advocate anticipates 2026 challenges due to staffing reductions and retroactive changes to tax law
State-By-State-UpdatesCalifornia adds animated and competition TV shows to its Film & Television Tax Credit Program.
Tax Planning TipsHow do the OBBBA tax policies impact retirement planning?
Around the Tax World- march 10, 2026
In The HeadlinesThe Trump administration takes a 10% stake in Intel.
What's New In The Tax World?The IRS has released a new OBBBA schedule: Taxpayers can now claim a tax exemption on tips, overtime, and car loan interest
State-By-State-UpdatesCalifornia lawmakers are torn over a new gas tax study.
Tax Planning TipsHow could A.I. impact the way taxpayers approach filing season?
Around the Tax World- February 24, 2026
In The HeadlinesTariffs and A.I. top the “Global Risks Report” for 2026.
What's New In The Tax World?Why are tax refunds being issued more slowly this year—and how might this impact the economy?
State-By-State-UpdatesGeorgians could see an extra $500 through the surplus tax refund program.
Tax Planning TipsHeirs are waiting for more than a year to receive tax refunds after a loved one’s death
Around the Tax World- February 10, 2026
In The HeadlinesA.I. is headed to outer space: Elon Musk closes a record-setting deal as SpaceX acquires startup xAI.
What's New In The Tax World?What’s new with the clean fuel tax credit?
State-By-State-UpdatesCalifornia’s proposed mileage tax won’t make it onto the highway just yet.
Tax Planning TipsThese are the scams to watch out for this tax season
Around the Tax World- January 27
In The HeadlinesHow will the “sell America” trade impact U.S.-centric investments?
What's New In The Tax World?Has your state resolved to lower individual income taxes in 2026?
State-By-State-UpdatesAlabama cities filed a lawsuit against the internet sales tax—now the legislature is pushing back.
Tax Planning Tips2026 could be the year you reap maximum benefits from homeowner tax deductions
Around the Tax World- January 8
In The Headlines2026 kicks off with labor market concerns and a slowly rebounding stock market.
What's New In The Tax World?The long-debated ACA health subsidies have expired—what’s next?
State-By-State-UpdatesCalifornia asks an important question: is a tax on billionaires worth losing a few?
Tax Planning TipsElon Musk donates $100 million Tesla shares to charity before the year-end.
NOT A MEMBER YET?
SUBSCRIBE TO GET ALL OF OUR
GREAT ARTICLES AND RESOURCES!
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.
