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Disclaiming to Save Taxes

It’s not enough for the founder of a closely held business to have successfully established the business. The business has to grow, not only to increase profits, but also to make it more competitive and to diversify its...more

Hospitals and Community Benefit: Senators See a Shortfall

For many weeks, we’ve been hearing about the IRS’s plans to use the funding provided under the Inflation Reduction Act[i] to increase and expand its compliance and enforcement efforts with respect to the wealthy, high-income...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

The Trust Fund Penalty – Times May be Tough, But Don’t “Borrow” from Withheld Taxes

It’s wonderful to be part of a successful business, especially in a strong economy. The owners are probably enjoying a more than just decent return on their investment and, in most cases, are getting along well enough. The...more

Open Transaction Treatment for The Liquidation of a Partner’s Interest

Another Mess- Congress has only a few days to avert a “shutdown” of the federal government. It’s not looking good in the House, as Speaker McCarthy has struggled to bring certain members of the majority into line, while...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

Withholding Taxes: Deferred Comp and Services Overseas

Approaching Year End- Which holiday do you dread the most? For me, it has always been, and likely will always be, Labor Day. Of course, with each passing year, anything that I describe as “always” is less meaningful than...more

Tax Compliance: Self-Assessment, Transparency, and Enforcement

NY’s Almost There- Back in June of this year, New York’s legislature passed a bill that, if enacted, would create the first state-level public database with information regarding the ownership of limited liability...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

Transferee Liability for Estate Tax: The Downside of Being a Beneficiary

Death of a Parent- In the context of a family-owned business, it is often the case that the matriarch or patriarch of the family is also the chief executive of the business. They may have founded the business, or they may...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

Partnership Losses But No Outside Basis? Too Bad

Losses Weren’t Always Bad- Most tax advisers are aware that, prior to the Tax Reform Act of 1986 (the “TRA”),[i] the Code placed few limitations on the ability of an individual taxpayer to use deductions from a particular...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

Enough Already – Eliminate Downward Attribution and Accidental CFCs

It’s Complicated- The Code includes a number of complex rules that are aimed at those overseas business and investment activities of U.S. taxpayers that Congress has determined may result in the improper deferral or...more

Thomas Paine and Today’s Tax Debates

Earlier this week, the United States celebrated the 247th anniversary of its declaration of independence from the United Kingdom of Great Britain, though the latter did not formally recognize the independence of its thirteen...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

Corporate-Owned Life Insurance, a Redemption, and The Value of a Decedent’s Stock

Estate Tax – It’s a Killer- One of the reasons often given for eliminating the estate tax is the substantial economic burden it places upon the estate of a deceased business owner and upon the business itself. Specifically,...more

Tax Planning for Business Owners Who Shortchange Themselves

Something’s Wrong- Of late, a not insignificant number of the business owners with whom I’ve been working have raised some concern over whether they are financially prepared for the next stage of their lives. ...more

Supreme Court Upholds IRS Collections Summons Without Notice

The Supremes- The Constitution has figured prominently in the news of late. In the days preceding the initial discussions among members of the Administration and the Congressional leadership regarding the debt ceiling,...more

Can You Be Sure You’ve Left New York Before The Sale of Your Business? Will It Matter?

Hasta La Vista N.Y.- Wealthy individuals continue to leave New York for tax friendlier jurisdictions. Be Prepared- Some of these taxpayers take a very methodical approach toward planning for their departure. They...more

Indirectly Held Profits Interests and Rev. Proc. 93-27

At war with Russia in eastern Europe, a nascent competing world order, mass shootings and bank failures at home, questionable audit practices by the Big 4 . . . everywhere, debt ceilings and the risk of default, inflation,...more

Selling Your Business? Careful of Pre-Sale Contributions of Stock to Charity

Charitable Giving Update- According to a recent report on charitable giving, the number of donors at every level of giving dropped during the first three quarters of 2022. The number of new donors was down by over 19...more

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