Category: Tax

One of the nuances that come up in tax planning involves the interplay of state law and federal tax law. This brings in all of the nuances and challenges under state law to federal tax law. For example, one common nuance in business transactions arises when the parties to a business arrangement do not document……

Do you own a company and want to sell to de-risk your holdings but don’t want to pay tax now? And when you do sell, do you still want lower capital gains rates? That’s the most common goal for those considering tax planning. Capital gains rates are lower than ordinary income rates. Tax planning focuses……

A core principle of U.S. law and a foundation of our legal system is the presumption of innocence. The burden of proof lies with the accuser, not the accused. This underpins the right against self-incrimination and the right to legal counsel to mount a vigorous defense. However, this framework unravels if the accuser can access……

Our tax law imposes penalties on taxpayers who fail to file tax returns or pay taxes on time, unless the taxpayer can show “reasonable cause” for the delay. In United States v. Boyle, the Supreme Court established a bright-line rule that reliance on an accountant or agent does not constitute “reasonable cause.” There are nuances……

Programs involving third-party vendors providing rewards, like hotels, airlines, and fuel companies, can amass substantial value over time. The term “substantial” is an understatement. “Massive” is more fitting. The tax law for these arrangements is not clear as it touches on concepts like trust funds, accounting methods, and redemption deductions. Given the size of the……

Many believe that once you elect an entity’s tax classification, you are locked into that choice for at least 5 years. Conventional wisdom says that the tax status cannot be changed within a 5-year or 60-month period. However, a recent IRS private letter ruling shows this is not necessarily the case. In PLR 202341001, the……

There have been several lawsuits filed against the IRS for unlawful disclosure of taxpayer information. These include a suit filed by President Biden’s son, a lawsuit filed by the IRS against IRS contractor Charles Edward Littlejohn for leaking taxpayer information to news outlets–which apparently included former President Trump’s tax returns and returns for many other……

Many people have experienced the pain of an investment gone wrong. You put money into a business, loan funds to a friend, or participate in a real estate venture, expecting strong returns. But instead of profits, you end up suffering losses when the deal unravels. It leaves you wondering – can I at least deduct……

Payroll taxes kill businesses. It is very easy to get behind, whether the business owner uses the funds to pay other expenses or due to a mistake. Once there is a payroll tax balance, it can be very difficult to catch up. The penalties and interest compound the problem. If you’re a business owner and……

Tax attorneys frequently come from an accounting background. This may seem like an unrelated skill, but it often plays a pivotal role in effective tax planning. The ability to navigate revenue and expenses and debits and credits not only ensures accurate financial reporting but also lays the foundation for strategic tax planning. Tax planning often……