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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
Getting Maximum Value from Small Business Stock Losses
When an individual sells a stock for a loss, it is a capital loss, and Congress makes it difficult for individuals to use their capital losses. The tax law only allows capital losses to the extent of capital gains. If capital losses exceed capital gains, the individual can only use up to $3,000 per year against ordinary income ($1,500 if married filing separately). However, there is a way around this rule: Losses on Section 1244 stock are ordinary losses, and claiming this valuable tax benefit allows an individual to save thousands of dollars in tax in the year of sale compared to the standard capital loss treatment. Let’s review what qualifies as Section 1244 stock, what benefits a taxpayer can get from Section 1244 stock, and how to claim those benefits on a tax return.
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CURRENT EDITION
What Do You Ask Indie Game Developers at Tax Interviews?
When you take on a new client, the tax interview is one of the most crucial elements of ensuring that their tax documents are prepared correctly. Both individual and business clients should provide you with a road map for their current tax situation, what they expect it to look like in the near future, and how your tax planning and preparation skills will help them with their business or financial goals. To focus specifically on business clients, questionnaires that the client fills out beforehand can efficiently cut down on facetime. This allows you more time to ask focused questions and learn about your client’s business needs and environment. But if your client is a game developer, specifically an indie game developer, there’s some nuanced questions you should ask in person or as an addendum to your questionnaire after you’ve read about the basics of doing business with game developers.
Using AI In Your Tax Practice? Choose The Nuclear Option
I always know when something, especially something bad, is trending on social media. Why? Because I’m not on social media and I still hear about the issue. Lately, I’m getting disturbing reports of the cavalier attitude that many tax practitioners are taking towards the use of AI in their practices. Apparently even the IRS is catching on because in late June 2026 the Office of Professional Responsibility (OPR) sent a bulletin to practitioners reminding them of their obligations under Treasury Circular 230 and how the circular’s provisions apply to using AI in a tax practice. The bulletin includes a decent list of best practices, and I recommend reviewing the bulletin and the applicable sections of Circular 230 after you finish this article.
Help Your Clients Implement a Fortune 500 CFO Strategy
For decades, some of America’s largest corporations have used a financial strategy that gives their CFOs greater control over insurance costs, helps them finance risks the commercial market handles poorly and creates an opportunity to retain underwriting profit when losses come in below expectations. Approximately 90% of Fortune 500 companies have captive insurance subsidiaries.¹ Historically, the economics favored organizations with substantial capital, large insurance programs and the resources to support their own insurance operations. Small and midsize businesses rarely had the scale to justify the cost and complexity. That equation has changed. A mature network of specialized insurance professionals and structures now allows qualifying privately held businesses to pursue many of the same risk-financing advantages. Federal tax law can further improve the economics for certain smaller insurance companies. For CPAs and tax professionals, this creates an advisory opportunity. The challenge is recognizing which clients could benefit and what conditions must exist before recommending it.
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.
