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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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Don’t Forget the Cohan Rule but Try Not to Need It

We are creeping up to the centennial of the Cohan rule. Learned Hand’s opinion for the Second Circuit in Cohan v. Commissioner came out on March 3, 1930 . I love this rule so much that I've made it the Prime Directive in my own book, Reilly’s Laws of Tax Planning: “If you don’t have documentation, at least have a plausible story.” However, subsequent legislation, changes in societal expectations, and the passage of time have eroded the usefulness of the Cohan rule for taxpayers. In recent years, there have been more instances of courts refusing to apply it than allowing its use. That’s why in Reilly’s Sixteenth Law of Tax Planning, I advise people to “being right without substantiation can be as bad as being wrong.”

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CURRENT EDITION

The Benefits Your Military Veteran Clients Aren’t Using (And Why That’s a Planning Problem)

Why aren’t more veterans using the benefits they’ve earned? Part of the problem is awareness, and part of it is discomfort (for both veterans and advisors). After all, veteran benefits are rooted in service-connected health and trauma, placing them in a category that often feels more personal than financial. That alone can deter veterans from discussing their disability compensation and keep advisors from broaching the subject altogether. The result is financial plans that look optimized on paper but are built on incomplete assumptions and missed opportunities – opportunities that have been more than earned.

Start the Year Right: Your WISP Doesn’t Have to Be a Tax Season Nightmare

The mere mention of a WISP makes most tax professionals want to suddenly lose their internet connection. It sounds bureaucratic, technical, and deeply unfun. But here’s the good news: creating and maintaining a WISP does not have to feel like a compliance root canal. And ignoring it can turn into something far worse than an IRS audit. Let’s talk about why you need one, what it’s actually supposed to do, and how to get it done without wrecking your sanity in the middle of filing season.

Fleeing High Tax States And The Stickiness Of Domicile

Part of preparing to leave a high state tax is facing up to the fact that the tax collectors of high-tax states can be kind of clingy. There is more to changing your residence for tax purposes than simple steps like a new driver’s license and a change in voter registration.

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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