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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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Bob Dylan Shows How to Beat an Imminent Tax Increase

Timing might be one of the oldest, most valuable tax strategies known. Essentially, a timing strategy allows a taxpayer to pay tax when rates are generally lower rather than when in a higher tax bracket or when facing increasing tax rates. Given this, 2020 may have been an optimal time to sell capital assets if tax rates rise under the new administration. President-elect Joe Biden has suggested taxing capital gains as ordinary income for high-income taxpayers (more than $400,000), as well as raising the top tax rate from 37% to 39.6%. Here’s how to cash in on the lower rates and, more importantly, when. While tax law changes seldom pass quickly, we often see changes made retroactive to the beginning of the year they are voted into law. Based on a recent story in The New York Times, Bob Dylan may have anticipated the increase when he sold the copyrights to his catalog of more than 600 songs for $300 million. Not to fret if you found yourself missing the beat of Dylan’s lead, there are many things a taxpayer can do to reduce capital gains tax, especially for self-created works of art. Here’s how.

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CURRENT EDITION

Editor’s Pick: The Future of Digital Product Taxation—What Tax Professionals Need to Know

As states increasingly focus on taxing digital products, tax professionals need to be aware of how these changes will affect their clients and businesses. The Multistate Tax Commission (MTC) is at the forefront of efforts to create more uniform approaches to taxing digital goods, and their proposals could have far-reaching consequences for compliance, pricing strategies, and audit risks. Here’s a breakdown of the major proposals under consideration and how they will impact sellers of digital products—and the tax professionals advising them.

Striking a Balance: Pitching to the Umpires of Tax Law – Understanding US Tax Court Judges through the Art of Baseball Analogies

In this fascinatingly original article, we explore the striking parallels between America’s pastime and the high-stakes world of tax litigation. Prepare to be surprised as we reveal the hidden connections between the umpires of the diamond and the judges of the Tax Court. From the precise strike zones of regular judges to the veteran expertise of senior judges, and the specialized skills of special trial judges, you’ll gain a newfound appreciation for the officials who keep the game of tax law fair and balanced.

Dodging the IRS Penalty Flag: Avoiding the Accuracy-Related Penalty

A penalty specifically for taxpayers who have made a mistake on their return. That’s how I explain the accuracy related penalty to taxpayers. This penalty carries a punch as well, with 20% of the tax the IRS didn’t receive due to the taxpayer making a mistake. This seems harsh out of context. The reason for this harshness is because the IRS considers these “mistakes” to be intentional due to taxpayer negligence. This is one of the reasons at my firm that we encourage our clients to take their time when filling out the intake form and gathering their documents. Omitting an income document can be costly in the end to both you and your client. The IRS will hit your client with penalties that they could have avoided, and you may compromise the integrity of your firm.

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.

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