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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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Payroll Taxes — The Nail in the Small Business Coffin

“Two men showed up saying they were from the IRS because I hadn’t paid my taxes. It scared me to death. Am I going to jail? Can they do that? I’m scared.” That is what the taxpayer blurted out as soon as I answered my business phone. Now before you say, “Timalyn, no way!” Yes, way! This was February 2020 when the world was still open, and the IRS was wide awake. Revenue officers were still on the phone making calls and showing up to businesses. Since the pandemic, many taxpayers, business owners included, have become lax in taking care of their tax obligations. This is due not only to many small and micro businesses still struggling financially, but also because the IRS has not been as aggressive the past few years. Business owners with employees are in a far more dangerous position if they have not kept up with their taxes. That’s why we’re going to look at one of the worst types of taxes to get behind on, payroll taxes. One of my mentors even refers to them as the “kiss of death” to business owners. The penalties for not paying payroll taxes can bury and put the nail in the coffin of most small businesses. Let me show you how these taxes can be the grim reaper. Let’s start from the top with what payroll taxes are and how the payroll tax penalties work.

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CURRENT EDITION

Worrisome Messages Subtly Delivered Via Recent Tax Developments

Tax professionals are inundated with tax developments from all branches of the government and from all levels of government on a daily basis. Our technical tax knowledge expands weekly. Given the immensity of tax law changes in P.L. 119-21 (July 4, 2025), informally named the One Big Beautiful Bill Act (OBBBA), and the guidance we’ll continue to get over the next few years along with non-OBBBA updates, we might run out of time and bandwidth to step back and ask what additional relevance this guidance, as well as various reports issued by the government every day, mean for the well-being of our tax system. This article unpacks select tax law changes and government documents to offer four subtle messages within them. Generally, the messages don’t bode well for an effective tax and revenue system. The article ends with some suggestions on what can help improve our tax system.

Sirius Solutions and the S Corp or Partnership Choice

The Fifth Circuit Court of Appeals opinion in Sirius Solutions L.L.L.P. v. Commissioner may change our views of entity choice. If the decision holds up, partnerships will be able to effectively make the portion of limited partner income subject to self-employment tax whatever they want, including zero. This contrasts with the IRS position upheld by the Tax Court in Soroban Capital that treated all of the income of limited partners who were active in the business as self-employment income.

Niche Down to Scale Up: How Specialization Drives Visibility and Profitability

For many accountants, narrowing our focus can feel risky. We are trained to serve anyone who needs help and provide stability in any financial situation. Choosing a niche often raises concerns: Will we turn away good clients? Will we limit opportunities or reduce business stability? These are common doubts many of us have faced in our careers.

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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