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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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10 Ways Certified Tax Planners Can Prepare for Increased IRS Focus on Documentation During Audits
The IRS is ramping up scrutiny of high-net-worth individuals and businesses, increasing audit rates by over 50% for those earning above $10 million. Recent IRS initiatives backed by Inflation Reduction Act funding have intensified enforcement on wealthy taxpayers, large partnerships, real estate investors, and tech businesses. IRS agents are digging deeper during audits and expecting taxpayers to produce more documentation to support every position on their returns. To help clients navigate this environment, certified tax planners must take proactive steps to bolster documentation and audit readiness. Below are ten authoritative strategies, complete with industry examples, IRS policy references, and best practices, to prepare for the increased IRS focus on documentation.

Best Practices for Surviving (and Helping Your Client Survive) an IRS Audit
Few things strike fear in our clients’ hearts more than an IRS notice, especially one that says a client’s tax return is being examined or audited. While this must be dealt with on a timely basis, it is not a reason for you, the tax professional, or the client to panic. Here, I’ll discuss a range of best practices to ensure the success of your client’s case, plus what to do when things go awry.
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Editor’s Pick: BOI Reporting: A Game of Legal Ping-Pong
For tax professionals trying to guide their clients on Beneficial Ownership Information (BOI) reporting, the last few months have felt like watching a never-ending game of legal ping-pong. Deadlines have been set, overturned, reinstated, delayed, and challenged in court—leaving many businesses (and their advisors) unsure of when, or if, they

CTA on Pause! What Tax Pros Need to Know About the Nationwide Injunction and BOI Reporting
On December 3, 2024, a U.S. District Court judge issued a nationwide preliminary injunction prohibiting FinCEN from enforcing the Corporate Transparency Act (CTA) and its associated Reporting Rule. This injunction halts the January 1, 2025, deadline for Beneficial Ownership Information (BOI) reporting, leaving many tax professionals and business entities questioning

Tax Scams: What You Need to Know About “Sovereign Tribal Tax Credits”
Tax scams come in many shapes and sizes. Some schemes aim to steal money or identities, while others present as legitimate-looking investment opportunities with promises of reducing tax bills. These offers often come from law firms, investment groups, financial advisors, and even sophisticated organizations. They tempt taxpayers with strategies like

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
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Inventory Expensing and The Cash Method: Changes from the TCJA
Join Lucien P. Gauthier as we discuss these two changes made by the TCJA in depth.

Taking the Mystery Out of Revised Energy Credits for Individuals
Learn valuable tips to help your clients claim the new residential energy and electric vehicle credits.

Tax Season 911
Your preparedness plan to create tax savings and survive the busiest of times without falling into old habits!
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Featured Authors

Amber Gray-Fenner is an Enrolled Agent and tax practitioner specializing in tax returns, planning, and representation for individuals and small businesses. She owns Tax Therapy, LLC in Albuquerque, New Mexico.

Matt Metras, EA, owns MDM Financial Services in NY, specializing in bookkeeping and taxation for cryptocurrency clients. He’s an educator on cryptocurrency taxation and actively engages in community advocacy.

Jeff Stimpson, has been a tax and finance writer for 25 years. Hee contributes to publications like Accounting Today and Financial Advisor. His other credits include sales tax, technology, and practice management, residing in New York.

Annette Nellen is a professor and tax program director at San José State University, with extensive involvement in tax organizations and a focus on tax policy, cryptocurrency, and education.

Peter J Reilly graduated from the College of the Holy Cross, worked in CPA firms like Joseph B Cohan and Associates and CCR LLP, and now runs a tax practice while writing for Forbes.com.

Thomas Gorczynski, EA USTCP CTP, is a tax expert known for speaking and educating on federal tax law. He’s editor-in-chief of EA Journal, co-author of the PassKey Learning Systems EA Review Series, and runs a tax practice in Phoenix, Arizona.
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Think Outside the Tax Box provides tax reduction strategies along with practical
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