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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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FEATURED CONTENT
The Tax Lives of Performing Artists
Performing artists are everywhere. Whether you’re a fan or indifferent, they’re tough to ignore. They color our world with print, broadcast, and social media coverage. We have actors, musicians, newscasters, and podcasters performing live, streaming online, captured on film/radio/television, and just about everywhere in an expanding online universe. We celebrate their triumphs, empathize with their trials, feel shocked at their gaffes, and grieve for and with them. We may not think we have much in common with performers, but we do have one commonality: We’re all taxpayers! A performer’s life may seem glamorous, but it’s hard work and not always financially predictable. The tax lives of performers are complicated. They have income and expenses, but with many twists and peculiarities. Twists and peculiarities can make it both interesting and complex when navigating the Tax Code, but performing artists need tax reduction, too. Tony Nitti said, “It has to suck to make your living as an artist.” But paying taxes as an artist doesn’t have to suck when you have a great tax plan. To read more about the unique tax planning opportunities available to performing artists, continue reading.
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CURRENT EDITION
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.
Structured Installment Sales Making Comeback – How Good A Tool Is It?
Structured Installment Sales (SIS) have been making a comeback. Historically low interest rates starting in 2011 made them go out of favor. Starting in 2018, insurers started coming back into offering them. MetLife expanded its SIS solution to 49 states, Puerto Rico and D.C. in 2022. You need to know about SIS and it deserves a place in your toolbox. You might not be using it as often as the toolmakers imply. I took a look at SIS in 2023 and was a little more enthusiastic about it than I am now. Let’s dig in.
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.
