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- 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?
READ MOREAround the Tax World – June 11, 2024
In The Headlines - Spotify is upping their subscription costs—and stock investors are responding favorably.
What's New In The Tax World? - Republicans hustle to assemble a new tax package in preparation for the election.
State-By-State Updates - California lawmakers are debating where online sales tax revenue should be funneled.
Tax Planning Tips - Do you qualify for an automatic extended tax filing deadline of June 17th? Make sure you understand which rules apply for you.
Around the Tax World – May 28, 2024
In The Headlines - Ryan Reynolds turns his entrepreneurial energy toward the world of sports.
What's New In The Tax World? - The IRS is cracking down on large partnerships and companies are evaluating how to prepare.
State-By-State Updates - California is poised to become the first state to levy an excise tax on guns and ammunition.
Tax Planning Tips - The list of vehicles that qualify for the EV tax credit is constantly shifting—which ones qualify now?
Around the Tax World – May 8, 2024
In The Headlines - The Biden administration faces another lawsuit battle against the Chamber of Commerce. The topic? Non-compete clauses.
What's New In The Tax World? - New guidelines for clean energy tax credits will impact electric vehicles, aviation fuel, and monetization of tax credit transfers.
State-By-State Updates - Colorado approves a tax reform package that includes changes to income tax, sales tax, and state revenue refunds.
Tax Planning Tips - Biden’s proposal to tax unsold assets is met with pushback.
Around the Tax World – April 25, 2024
In The Headlines - Samsung edges out Apple as the top phonemaker worldwide.
What's New In The Tax World? - Biden publicly releases his tax returns as presidential candidates continue the conversation on tax policy
State-By-State Updates - Californians living in San Diego county get an extended tax deadline
Tax Planning Tips - Could the expanded Child Tax Credit still manifest in 2024?
Around the Tax World – April 9, 2024
In The Headlines - Will Trump be out $450 million?
What's New In The Tax World? - Scams abound during this tax season: here’s how to avoid falling prey
State-By-State Updates - Illinois is recruiting volunteer firefighters by offering a special tax credit.
Tax Planning Tips - Planning for retirement? Don’t overlook the saver’s tax credit.
Around the Tax World – March 21, 2024
In The Headlines - Will the U.S. become a TikTok-free zone?.
What's New In The Tax World? - A $78 billion tax bill passes the House but hits walls in the Senate
State-By-State Updates - Colorado residents may be eligible for an $800 refund this tax season.
Tax Planning Tips - Is your property tax bill astronomical? Consider whether you can appeal your property tax assessment.
Around the Tax World – March 7, 2024
In The Headlines - H&R Block and TurboTax have been accused of “deceptive advertising” by the FTC.
What's New In The Tax World? - The IRS levels up on cryptocurrency tax compliance with the help of two former crypto executives.
State-By-State Updates - Kansas shuts down a $1.6 billion tax cut package including a flat income tax rate of 5.25%
Tax Planning Tips - Planning your retirement? Consider these states with the lowest tax rates.
Around the Tax World – February 22, 2024
In The Headlines - Who will win in the battle between The New York Times and OpenAI?
What's New In The Tax World? - The popular EV tax credit has yielded $135 million in reimbursements for automotive dealers this year.
State-By-State Updates -California considers a ballot initiative that would limit local and state governments’ ability to raise taxes.
Tax Planning Tips - If you have long-term care insurance, keep in mind these tax deduction limitations.
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.
