LOOKING FOR LEGAL WAYS
TO REDUCE TAX?
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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The Ultimate Year End Tip Guide and the Search for the Great Shelter
Coming up on the end of the year, year end planning is kind of a ritual for me. I take my first pass in early November and will do it again no later than December. It is pretty boring. I thought it would be worthwhile to do a survey of a variety of year end tips articles. What is going on here is something like Ahab’s hunt for the great white whale. I am looking for something to help out HENRY. HENRY stands for High Earnings Not Rich Yet. I wrote about the quest in 2019. I found nothing much for HENRY then, and this year’s batch of advice articles really does not offer much. The articles do not all say exactly the same thing, but there is a lot of commonality. Due to the sophisticated nature of the readership of TOTTB, I will just allude to the tips, not explain them in detail, because I am going someplace else with this. There is nothing dramatic for HENRY coming from conventional advisers, which accounts for HENRY’s vulnerability to sketchy tax shelters. I will share a bit about what I have seen in that department and reflect a bit.
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Lessons Learned from the Tax Court: An Olive Branch in Tax Court
“Everything is deductible until the audit” is an adage frequently repeated in the tax preparation industry. Generally, it’s mentioned tongue-in-cheek, but today’s taxpayer (and her tax pro boyfriend) may have taken it a bit too literally. Additionally, cutting corners may seem like a time-saving strategy in the moment, but the potential to backfire can’t be ignored. In this case, the taxpayer is about to learn things the hard way.

Two Tax Systems: The Fundamental Divide That Shapes Every Client Strategy
As tax professionals, we must recognize a profound truth that most Americans never fully grasp: The United States doesn’t have a single tax system, it has two fundamentally different systems operating in parallel. Understanding this dichotomy is perhaps the most important insight you can share with your clients, as it forms the foundation for virtually every advanced tax strategy.

When Your Client’s Business Fails: Easing the Tax Pain
The Internal Revenue Code provides several meaningful tools to ease the tax pain when a business fails. The problem is that many of these provisions require advance planning, timely action, or both. If you’re not looking for them, you’ll miss them, and your client will pay for it. In this article, we’ll look at net operating losses, Section 1244, worthless stock and bad debts, the hobby loss rules, cancellation of debt, and key opportunities to look back at prior years.
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.

