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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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FEATURED CONTENT
Avoid IRS Red Flags in Multiple Business Strategies: A Guide for the Wary Tax Business Owner
In the labyrinth of tax planning and business structure, the path to protecting your client’s multiple business strategy from the ever-watchful eye of the IRS can be as intricate as a well-played game of chess. However, while the strategic moves might be complex, the rules of the game are quite clear. Today, let’s dissect these rules with a blend of cautionary tales and cheeky wisdom, ensuring your business maneuvers stay sharp and IRS-compliant. Ever heard of the tax strategy to just “create a new C corporation” and shift income by paying management fees from your main company? Well, so has the IRS, and they are highly skeptical when they see it in the field. The Aspro, Inc. v. Commissioner case serves as a stark reminder for taxpayers about the importance of meticulous documentation and the strict adherence to IRS guidelines for deducting management fees. Aspro, an Iowa-based C corporation in the asphalt-paving business, faced scrutiny over its practice of paying "management fees" to its shareholders, which the IRS and subsequent court rulings reclassified as non-deductible disguised dividends.
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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
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
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
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.
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.
