LOOKING FOR LEGAL WAYS
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
Segregating Activities Can Optimize Tax Savings for Professional Gamblers, Gamers, and Contestants
You’re tax professionals. You don’t need me to tell you that the money you are going to win in the virtual office pool on “the big game” is taxable income. You also don’t need me to tell you can’t net your winnings with the cost of the wager. You don’t, right? Most of the rules for reporting gambling income and deducting gambling losses for individuals are well understood with the possible exception of the session rules for slot machine play. I’m not going there—well, not in this article. This article is going to explore the nuances of tax optimization for people who have decided to go all in and turn their leisure time activities into a job.
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CURRENT EDITION
An Analysis of the OBBBA’s Trump Accounts (Part 1)
The One Big Beautiful Bill Act, signed into law by President Trump on July 4, 2025, added a new tax saving tool for minors, the aptly named Trump Accounts. In this article, I go over the details of the new Trump Accounts. In part II, I will discuss some of the potential tax planning opportunities and pitfalls related to the new accounts.
Student Loans After the OBBBA Part 1: New Rules Every Advisor Needs to Know
Big changes are coming to the student loan world (yet again), and they’re not the kind you can just skim past. The One Big Beautiful Bill Act (OBBBA) has reshaped how much students will be able to borrow, how they’ll repay it, and which programs will qualify for federal aid going forward. For financial and tax professionals, these shifts aren’t just policy updates. They’ll set the stage for how you’ll advise clients for years to come… and could even change the way you manage your own student loans. In Part 1 of our OBBBA student loan series, we break down the nuts and bolts of these new rules to help advisors (and borrowers) get some clarity on the collective question: “Seriously, what’s going on with student loans?”
IRS And Courts Have Wisdom to Offer Startup Businesses
There is a wealth of business wisdom in a fairly unlikely area. All the businesses involved lost money, sometimes enormous sums. The source is the litigation and regulation around Code Section 183 of the Internal Revenue Code – Activities not engaged in for profit. In order to deduct those losses against other income, taxpayers need to convince the IRS or the court that they had an honest objective of making a profit. The determination of whether an activity is carried on for profit is made by reference to objective standards. Is it possible that following those standards might contribute to you being profitable? It’s worth thinking about.
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.
