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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

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

Funding the Buyout of a Deceased Shareholder With Corporate-Owned Life Insurance – Did the Court Decide Connelly Correctly?

You may have heard or even read about the U.S. Supreme Court’s recent decision regarding the date of death value of a deceased shareholder’s shares in a closely held corporation that owned a life insurance policy on the...more

Trust Beneficiary Engages In Like Kind Exchange Using Trust Property

It is a basic principle of the income tax that the gain or loss realized by a taxpayer from the conversion of property into cash, or from the exchange of property for other property that differs materially in kind from the...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

Transfers Within the Family Business: Gifts or “Ordinary Course” Transactions?

It is not uncommon, in the context of a business entity in which a family owns a controlling or substantial interest, for an adviser to encounter intersecting gift and income tax issues. This week’s post will consider one...more

Shareholder-Transferee Liability for a Corporation’s Income Tax

Would you be surprised to learn that most shareholders of closely held corporations, and especially those with minority or merely passive interests, believe they cannot be held responsible for the tax obligations of their...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

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

Supreme Court to Decide: No Realization Means No Moore Income Tax?

Many of you, perhaps most, may have read about a case that will be heard by the U.S. Supreme Court during its current term. The case, Moore v. United States, comes out of the Ninth Circuit Court of Appeals. The Supreme Court...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

Pre-Consolidation Conversions in the Accounting World – Tax Considerations

Another Change- Last week BDO confirmed that it was going to convert from an entity organized as a limited liability partnership under state law to one organized as a corporation. With that, BDO became the latest in a...more

Some Observations On Recent Conversions of Partnerships to “C” Corporations

Decisions- It is often the case that the optimal form of legal entity through which a business should operate, at least for income tax purposes, will depend in part upon the stage of its life cycle in which the business...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

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

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

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

Shareholder Beware: Personal Liability for N.Y. Sales Tax

Limited Liability? Many individual taxpayers who invest in a closely held business, including one organized as a corporation, fail to appreciate there are circumstances in which they may be held personally liable by a...more

Unreasonable Compensation As Constructive Dividend, Redux

An often-explored theme of this blog is the frequency with which similarly situated owners of similarly situated closely held business, facing a similar set of economic circumstances, and presented with a similar set of...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

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

Selling Your S Corporation’s Business? What If It’s Not an S Corporation?

Haste Makes Waste? How many of you are suffering from Build Back Better Fatigue? Seriously, it’s a thing. Sure, the House passed its version of the President’s tax and spending bill on November 19, and the Senate...more

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