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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

Tax Considerations and the Reclassification of Marijuana – We’re Not There Yet

Having been swept along for nine days “by the force of the hostile winds on the fishy sea,” Odysseus and his crew came to a strange land. After securing their ships, Odysseus sent some of his “companions ahead, telling them...more

The Supreme Court’s Non-Opinion On The “Realization” of Income – A Lost Opportunity?

In less than four months, the citizens of the United States will be electing their next President to a four-year term. They will also be deciding which of the two major political parties will “control” the Senate, the House,...more

Collecting an Individual’s Unpaid Taxes from Their Controlled Entities

An anonymous thinker, lost to history, is credited with having said that the unofficial motto of the IRS is, “We have what it takes to take what you have.” In some instances, the truth of the above statement is manifested in...more

“C’mon Man! Tax the Rich!” Business Owners Face Tax Increases*

Last week, Sen. Warren reintroduced her “Ultra-Millionaires” wealth tax proposal to the Senate. Query her timing. The measure has the proverbial snowball’s chance in Hell of being enacted by this Congress.Perhaps the Senator...more

The Family-Owned Business, Stock Options, And Personal Goodwill – a Smorgasbord of Tax Issues

Many of us have encountered variations of the following scenario: a parent owns and operates a business; one or more of their children are employed in the business; as the children mature and become more experienced and...more

The Family Business – Compensating Family-Employees

Hope you had a good Thanksgiving Holiday. Some of us probably feel we ate or drank either too much or not enough, watched too much or not enough football, or spent too much time discussing politics and the state of the...more

Debtor Corp’s S Election: “Property” in Bankruptcy?

Uncertain Future- The Congressional Budget Office (“CBO”) recently released some data for the federal government’s 2023 fiscal year. According to the CBO, the federal budget deficit for the year was $1.7 trillion, or...more

ESBTs and the Carryover of S Corporation Losses

Since 1995 to the present, the LLC has emerged as the entity of choice for the vast majority of entrepreneurs. This form of business entity owes its success to the flexibility and to the tax benefits that it affords its...more

Self-Employment Tax and the Limited Partner – Substance Over Form, or Something Else?

Last week, the IRS announced “the start of a sweeping, historic effort to restore fairness in tax compliance by shifting more attention onto high-income earners, partnerships, large corporations and promoters abusing the...more

Sale of Mortgaged Property – Amount Realized or COD Income

Do you feel as challenged as I do when someone asks you to explain the term “Bidenomics”? I know that it is predicated upon the imposition of higher taxes on businesses and their owners, which have not yet materialized....more

Should Closely Held Businesses Be Charitable?

Faulty Framework? The question posed above is not intended to be rhetorical. Rather, it is one that the owners of a closely held business should consider thoroughly before transferring or committing any business assets to...more

Debt or Equity? The Never-Ending Question For Closely Held Businesses

What Was Intended? Transactions between commonly controlled, closely held businesses are often conducted in an informal manner. This is unfortunate because, in the absence of documentation, it is sometimes difficult to...more

The President’s 2024 Federal Budget: “Reforming” the Taxation of High-Income Taxpayers

The Budget and Accounting Act of 1921 established the requirement that the President submit a budget to Congress for the upcoming fiscal year. Among other things, the proposed federal budget affords the President an...more

The Closely Held Business and The Tax Gap

Have you ever wondered whether you were barking up the wrong tree? That the solution to a problem may be found, not in the approach to which you were already committed and invested, but in an altogether different direction?...more

Trusts, the Death of a Shareholder, and The S Corporation Election

The Key Person- The closely held corporation is often a fragile creature. Too often, its continued success and well-being are overly dependent upon the continued involvement of one individual – namely, the founder and...more

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

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

Leaving New York? Can You Prove It?

“Summertime and the Living” Isn’t Easy- Summer in the New York Metro Area can be challenging. Some would say it sucks. It gets really hot. When it rains, it pours – no spritz here. The humidity is oppressive. Ironically, a...more

An S Corporation’s Sale of Real Property Following the Death of Its Shareholder

Don’t Do It- There are certain generally accepted “dos and don’ts” of which almost every investor is certainly aware. For example, do not put all your eggs in one basket; if an investment seems too good to be true, stay...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

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

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