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Closely Held Businesses and Their Owners Ask: What’s Big and Beautiful in the Recent Tax Law?

The “One Big Beautiful Bill Act” (the “Act”) was signed into law last week, on July 4. As promised by the White House, the Act extends – i.e., purports to make “permanent” – many of the otherwise expiring provisions that were...more

Taxes: An American Obsession?

Last week the United States celebrated the 249th anniversary of its declaration of independence from Great Britain. In celebration of the occasion, President Trump signed into law the One Big Beautiful Act which, among other...more

Writing Off A Loan – Simultaneous COD Income and Bad Debt Deduction? Not Necessarily

If you’ve been around closely held businesses long enough, you know that a transfer of money between a business and its owner, or between two related businesses, is sometimes characterized by the parties as a loan (“related...more

The Limited Partner Exclusion From Self-Employment Tax – But Who Is A Limited Partner?

An Agency Under Siege - The mission statement of the IRS reminds taxpayers that it is their responsibility to understand and meet their tax obligations, while it is the role of the IRS to “enforce the [tax] law with...more

Terminating a Trust? Don’t Forget to Consider This Tax Issue

Every conveyance of property or of an interest in property from one person to another is prompted, or at least influenced, by economic considerations. The parties to the transaction may swap properties, or one party may...more

State Taxation of a Nonresident’s Gain from the Sale of Stock –The Shot Heard Round the Country?

Last month, Bloomberg carried an article about a “small but growing trend” of states that are either cutting their individual income taxes or phasing them out entirely. According to the article, the states adopting these...more

Observations on Charities, Taxes, and Cash Flow

Few provisions of the Code have a single, clear meaning that leaves no room for interpretation. Even many of those that, on the surface, appear fairly straightforward, are usually open to alternative “understandings.”...more

“Hey Mom, Can I Have A Few Bucks?” Is It A Loan? A Gift? A Little of Each?

A parent will sometimes transfer money to a child to enable the child to make an investment that the child could not otherwise make on their own. For example, the child may have identified an attractive business opportunity...more

Transferring the Family Business To A Private Foundation? Are You Sure About That?

Charitable organizations are dependent, in no small part, upon the financial support of many successful business owners. The generosity of these individuals and their organizations may be a manifestation of several factors...more

NYC Transfer Tax, Charities, and Single Purpose LLCs – Are Lenders Beneficiaries?

According to the New York City Comptroller, the City collected approximately $1.13 billion in Real Property Transfer Tax (“RPTT”) in the FY 2024. The Comptroller’s Office has forecast that $1.21 billion of RPTT will be...more

New York Sales Tax: When a Responsible Person Acts Irresponsibly

Late last year, the Office of the State Comptroller (the “OSC”) estimated that sales and use tax receipts would increase by 2.3% in the SFY 2024-2025. The OSC also projected that collections from sales and use taxes would...more

Business Owner Borrows from Their Private Foundation – A Different Form of “For Profit Philanthropy”?

Many successful business owners attribute some part of their success to their community. For some of these owners, it is not enough to simply acknowledge this “debt”; they feel an obligation to share some of their financial...more

Not Aware of Your Business Partner’s Tax Situation? Maybe You Should Be

If you’ve worked with the owners of closely held businesses for even just a few years, you have realized they are only half joking when they complain about having the government as a partner. Consider how much federal, state,...more

Employer to Nonresident Employee: “You Cannot Work in New York”; New York to Employee: “We Will Tax You Anyway”

You are probably aware that many employers are discarding the fully flexible, remote work policies that were forced upon them – as “nonessential” businesses – during the COVID-19 pandemic[i] and which they retained as an...more

Expiring Federal Transfer Tax Benefits – Nothing is Certain or Lasts Forever

Just a few weeks ago, many individual taxpayers, driven by what they viewed as the relatively imminent expiration of the enhanced federal transfer tax exemptions, sought advice on how to leverage their remaining exemption and...more

The Status of the Corporate Transparency Act – It’s Not Clear

Few would argue that the federal government does not have a legitimate interest in preventing, detecting, and punishing tax fraud, money laundering, and other financial crimes. Likewise, I imagine few would disagree with the...more

The Holidays – A Time for Family, Reflection and. . . GST Tax Planning?

How was your Thanksgiving? I hope you celebrated the holiday in a pleasant setting with folks whose company you enjoyed, and with plenty of good food. I hope you participated in some interesting conversations or joined in...more

Abandoning N.Y. Domicile – Must the Business Owner Abandon Their N.Y. Business?

During the weeks leading up to the Presidential election, the media carried stories about wealthy supporters from each Party who had announced their intention to leave the country if the other Party’s candidate became...more

Choice of Entity for a U.S. Business- Passthrough Status Matters Beyond the U.S. Border

Decisions, Decisions - The owners of a closely held U.S. business will have to make many difficult decisions during the life of the business. Among the earliest of these is the so-called choice of business entity, the...more

Challenge to Collection Due Process? Will Supreme Court Affirm IRS’s Offset of Valid Refund With Disputed Tax Liability?

Earlier this year the IRS announced that, as part of its larger compliance efforts begun last fall under the Inflation Reduction Act, the agency’s stepped-up enforcement activity with respect to high wealth, high income...more

Thinking About Making Taxable Gifts Before the 2026 Sunset?

As we will see shortly, it is often “better to give than to receive,” though this statement begs the obvious question of whether it is better to do so during one’s lifetime or upon one’s death. Many well-to-do individuals...more

New York Tax Continues to Inconvenience Nonresidents Working Remotely

Last Friday, New York’s Governor Hochul delivered the following remarks at the annual meeting of the Business Council of New York State:“Someone asked me today, are we going to raise income taxes? I said, ‘I’m not raising...more

Unconstitutionally Excessive FBAR Penalties? It Depends

You may recall that earlier this year the IRS launched an initiative to pursue 125,000 “high-income, high-wealth” taxpayers who have not filed taxes since 2017. These were cases where the IRS received third party information...more

New York’s Tax Treatment of Compensatory Restricted Stock and Dividends in the Hands of a Nonresident Executive

As far back as I can remember, the end of August has always elicited a sense of dread comparable to what many schoolchildren, and a fair number of adults, experience every Sunday afternoon. In retrospect, I cannot say that...more

When A Shareholder Loses Control of Their S Corporation

If given their druthers, most transactional corporate attorneys would prefer to spend their day practicing “happy law,” by which they typically mean transactions that involve capital formation, mergers and acquisitions, joint...more

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