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LLC as S Corporation: Square Peg Meets Round Hole?

At different times over the course of the last thirty days or so, I have seen reports describing various plans to increase income taxes and/or wealth taxes on the “rich” that have either been endorsed or proposed by the likes...more

Private Foundations, Closely Held Businesses, And Distribution Requirements

“Show Me the Money”- Much has been written in recent months about how well the investment portfolios of private foundations have performed over the last several years. For example, a study conducted by the Council on...more

Business Expenses Paid by Shareholder, But Whose Deduction Is It?

Constructive Transfers- It is axiomatic that the tax treatment of interactions between a closely held business and its owners will generally be subject to heightened scrutiny by the IRS, and that the labels attached to such...more

Dividing the Multi-Family Corporation

Sibling Rivalry- You have probably encountered family-owned corporations in which the founder’s offspring are involved in the business to varying degrees. They may even own some equity, typically having received such equity...more

Shared Appreciation Interest: Debtor-Creditor or Partners?

When is a loan not a loan? When it’s something else – for example, equity. This is one of those pesky facts and circumstances issues that plague courts, taxpayers, and tax advisers to no end. Debt- On one end of the...more

Moving to the U.S.? Have You Planned for the Estate and Gift Taxes?

It is a fact that the phenomenon of human migration has been a major force in the history of the world. Indeed, among the themes that have remained constant during my years of practice, there are two that may be...more

Planning for the Interest Charge on Installment Sales: Decanting a Grantor Trust?

I recently encountered an interesting situation in which someone suggested that a grantor trust be decanted into a non-grantor trust before the end of the taxable year. The reason? To avoid the special interest charge that...more

New York to Taxpayer: “Forget What the Feds Said, You’re a ‘Responsible Person"

Where is the Economy Heading? According to the data released Friday by the Department of Labor, the U.S. economy added approximately 528,000 jobs in July, reducing the unemployment rate to 3.5 percent. Although this...more

S Corps with Real Property: Separating Shareholders & Partnership Envy

Tax Alchemy? How many of you remember Section 138509 of the Ways and Means Committee’s markup last September of what would have been the Build Back Better Act? (A moment of silence, please.) Allow me to jog your memory....more

The Transaction That Failed – Tax Treatment of Termination Fees

Deal Costs, Generally- Every purchase and sale of a business, whether from the perspective of the seller or the buyer, is about economics, and few items will impact the economics of the transaction more certainly or...more

Statutory Residence in New York: Time to Rethink the “Permanent Place of Abode” Test?

Escape from New York- According to data released by the IRS earlier this year, the pandemic triggered a “wealth migration” that saw high-tax states like New York lose high-income earners to low-tax jurisdictions such as...more

Will New York Be Looking At Your Federal Tax Return? Probably

State Finances- Much has been written over the last few weeks about the unprecedented financial cushion that many states have accumulated thanks to federal support prompted by the pandemic and larger-than-expected tax...more

Current Partnership Distributions: When Do You Figure Your Basis?

Withdrawing Value- In general, the owners of a closely held business have several options by which they may withdraw money from the business without selling their interest in the business....more

The Deduction of Cannabis Business Expenses Following New York’s 2023 Budget

The 2023 Budget- Last week, the New York Legislature passed the State’s 2022-2023 Budget. The $220 billion Budget reflects an $8 billion increase over last year’s budget (a more than 3 percent jump). It is also $4 billion...more

[Webinar] Lunch & Learn Series: A Refresher on Form 990: Tips and Traps for Tax-Exempt Organizations - April 14th, 12:00 pm - 1:00...

Please join us as Louis Vlahos and Bernadette Kasnicki provide a refresher on preparing Form 990, the tax return for tax-exempt organizations. We will review…...more

Constructive Dividends and The Closely Held C Corporation

Withdrawing Value- Any tax adviser who has represented closely held businesses and their owners long enough realizes there are certain recurring themes that transcend the otherwise unique characteristics of the industry of...more

Reasonable Compensation Meets The Principal Shareholder of a C Corp

Double Tax- The shareholders of C corporations have long sought legitimate operational and transactional structures by which they may reduce the double tax hit that is realized when such a corporation distributes its...more

Tax Court’s Decision On Assumption of Liability in M&A – A Clean Block or Goaltending?

Assumed Liabilities- If a taxpayer were to sell the assets that comprise the taxpayer’s business, they would realize gain if the amount realized by the taxpayer from the sale is more than the taxpayer’s adjusted basis for...more

Taxing NFTs as an Investment in “Art”

Segue- Earlier this month, the Treasury released a study in which it examined how transactions in “high-value art” may facilitate the laundering of illicit proceeds.[i] The study also considered efforts that be undertaken by...more

Me, Myself, and I: Tax Liabilities and Dealing with One’s Own Business

“It’s My Business”- The owner of a closely held business will often find it difficult to distinguish the business from their own person. That is certainly true for a sole proprietorship. In many cases, unfortunately, the...more

Deferring the Tax Hit on a Grant Equity to an Employee – Are You Prepared to Enforce the Forfeiture Provision?

“Would I ever leave this company? Look, I’m all about loyalty. In fact, I feel like part of what I’m being paid for here is my loyalty. But if there were somewhere else that valued loyalty more highly, I’m going wherever they...more

The Liquidation of a Partner’s Interest Under NYC’s Unincorporated Business Tax

Taxes and Snowy Weather? How many of you awoke Saturday to find that the winter storm about which we had heard so much during the preceding days had lived up to its hype? What was your first thought? “Fudge,” right?...more

Gifting Business Interests Before Selling the Business? Think Valuation

Counting the Days?- We are 302 days away from the national mid-term elections, to be held November 8, 2022, yet the first full week of the new year has already highlighted some of the economic issues with which the...more

New York’s Pass-Through Entity Tax, F Reorgs, and the Sale of An Electing S Corp

Timing- I had planned to post this piece during the third week of December, a day or so after the exchange between Senator Manchin and the White House sealed the fate of the Build Back Better plan, at least in its current...more

‘Tis the Season . . . to Recall Taxes?

Mention the “tax season” and most folks think of the weeks leading up to the April 15 deadline for filing one’s federal individual income tax return and paying the associated income tax. Truth be told, given the number of...more

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