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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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Side Hustles and Tax Tussles: Tax in the Gig and Share Economy Part One
I can recall looking for a part time job in local newspapers when I was in high school. Sometimes a friend and I would ride around with our $2.29 per gallon gas looking for places that were hiring. Facebook was gaining popularity but not for job posting. So, searching for jobs on my phone via an app was unimaginable. Advances in technology have changed the way that we do things in the world. Everything an individual needs to find a job is right at their fingertips. There are more opportunities to find gigs and be your own boss if that’s what one desires. There’s no question that the way people find ways to earn income has changed. What has not changed is the fact that the IRS wants their share of the income earned. But how do we apply the tax code to these new ways that taxpayers are earning money? We are going to break that down in this three-part series. Whether your client is doing odd jobs on an app like TaskRabbit, driving for Lyft, renting out their home or car, you will know how to guide them. This is what we are going to cover today with a focus on rideshare, delivery, and other service gigs.
Read MoreCURRENT EDITION

Will AMT Make a Comeback After OBBBA?
Following Betteridge’s Law of Headlines, the answer to the question posed in the headline is, “no.” Actually — because we’re talking about taxes here — we can say the answer is never so definitive, so let’s change it to “probably not.” But it’s more complicated than it may seem.

Why Citizenship, Residency, and Domicile Matter
If you spend any time in the world of cross-border taxes, you start to notice a pattern: the hardest problems usually begin with a deceptively simple question—who gets to tax you? And the answer is rarely as simple as “the country where I live.” That’s because tax systems don’t rely on just one concept to decide who belongs in their net. They use citizenship, residency, and domicile. These terms sound similar, and people often use them interchangeably in casual conversation, but in tax law they mean very different things. For globally mobile individuals, understanding the difference matters. You can be a U.S. citizen, a tax resident of another country, and still have your long-term home base tied to a different jurisdiction altogether. Each label can trigger different tax consequences, different filing obligations, and different planning opportunities.

Sophisticated EMR Software Meets Old-School Skimming: Lessons From The Aryanpure Case
The simplest way to reduce your taxable income from an S corporation is to take some of the gross receipts directly into your personal account without running them through the corporate books. Don’t mention this to your tax preparer and make sure they don’t find out. If you get caught by the IRS, though, hire an expert to explain why it is your preparer’s fault. This plan did not work all that well for a couple, both physicians, who were running two medical family medical clinics through an S Corporation called MedExpress. They ended up being liable for the fraud penalty which has the collateral effect of extending the statute of limitations indefinitely. At 75% the fraud penalty is as bad as it can get without losing your liberty.
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.

