Business Strategies

Using S Corporations to Minimize FICA And Medicare Tax

When United States Tax Court Judge Paris issued the opinion in the case of Ryan Fleischer in 2016 , it caused quite a stir in the tax blogosphere. And from what I have been able to gather off the record it remains of interest. The Fleischer decision makes it very difficult, if not impossible for some financial professionals to use S corporations to mitigate self-employment tax. Rather than attack on reasonable salary, the IRS took an assignment of income approach, which succeeded throwing planners for financial professionals like Fleischer into a bit of an uproar...

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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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CURRENT EDITION

Qualified Opportunity Zones After the One Big Beautiful Bill Act: What’s Changed and What It Means for Real Estate Investors

Joshua Youngblood, EA, CTRS, CRETS, NTPI Fellow

On July 4, 2025, the One Big Beautiful Bill Act (OBBBA) became law, representing the most significant reform of the QOZ program since its inception. It made the program permanent, tightened eligibility rules, introduced a rural-focused investment vehicle, and imposed robust reporting requirements. For tax professionals and investors, understanding these changes isn’t just about compliance – it’s also about strategy.

Vibe Preparing: Ignoring Partnership Agreement Impacts on K1s

Roger Ledbetter, CPA

Nothing derails a busy season schedule like being forwarded emails from client’s investors asking “are you sure the loss is allocated correctly?” It can expose a weakness in technical expertise – especially when it’s a partnership K1. Whether the operating agreement includes Safe Harbor or Target Capital allocations is one of the most important places to start for a preparer. And knowing these basics can be the difference between a confident reply or a lost week.

Deducting Gambling Losses: Part 2: Sessions Method

Keith Schroeder, EA

Recently I polled my peers on a social media platform dedicated to tax professionals. My hope was to find a resource for tax rules on a state level for handling gambling sessions. I knew it would be an uphill battle to get the information needed for a comprehensive guide state-by-state.
What surprised me was the response. A large percentage of tax professionals were either unaware of gambling sessions or were unclear on how gambling sessions were handled in their state. Since gambling sessions might be the best way to reduce taxes on gambling wins, a lot of money might be left on the table with clients paying the price. Even if the state a tax professional prepares most tax returns for does not have gambling, the likelihood a client travels to a state that does, gambles, and wins is high.