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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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Charlie Sheen Settles with IRS For $3.3 Million And A Possible Share in Future Earnings

Charlie Sheen’s tax woes seem to be at an end. I mainly remember Sheen as the star of Two and a Half Men, but there is a lot more to his career and fame than that. As I related back in January, IRS has been trying to collect on Mr. Sheen’s 2015, 2017 and 2018 returns. Many people have the impression that failure to send in the balance due with your return. will result in 87,000 agents willing to use deadly force knocking on your door, but it really doesn’t work that way. There is a lot of process. In some circles I think the return balance due is viewed as the sticker price on cars used to be or full tuition at a well-endowed university that wants to have a sprinkling of representation from the 99% attending…

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CURRENT EDITION

Remember, Influencers, the IRS Follows You Too!

The influencer marketing industry was able to grow during Covid as many advertisers had to adjust or cancel their marketing campaigns. This was because more people were sitting at home consuming content on social media. This new opportunity for smaller influencers has created a new group of taxpayers who need to know their new filing obligations. They’ll also be open to tax planning strategies that you have to help them reduce their tax liability.

Hobby Loss Regulations And Loper Bright

For me, the most exciting Tax Court opinion of 2025 was Judge Joseph Goeke’s supplement to his 2024 opinion in the case of Gary M. Schwarz. With a $1,851,878 tax deficiency, it is the largest hobby loss opinion since 2019. (The really big dollar cases tend to settle.)

Consult, Don’t Convince: Turning Discovery Calls into Advisory Opportunities

The most successful accountants aren’t the ones who pitch the hardest, they’re the ones who listen the most. When you ask better questions, you can diagnose problems that clients didn’t even know they had, which then helps us clarify outcomes instead of listing services. When we shift from “convincing” to “consulting,” discovery calls stop being “sales” conversations and start becoming advisory conversations. And advisory conversations naturally lead to advisory engagements.

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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