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Trust Fund Recovery Penalty & The Closely Held Business

Depending upon what you read or, perhaps more accurately, depending upon how much you believe of what you read, you may be aware that many closely held businesses are concerned about their future. Most of these survived...more

Estate, Gift, GST & Related Income Tax Proposals – What is the White House Doing?

Earlier this week the White House released its Fiscal Year 2025 Budget. Of course, the federal government has not yet adopted a budget for the Fiscal Year 2024 even as we approach that year’s halfway mark. But I digress. The...more

Rescission, Repossession, Real Estate – The Three R’s of Unwinding a Sale

How many times have you wished that you could undo something from your past, perhaps a string of incoherent statements made at a client dinner while slightly under the influence, or an expletive-filled email composed and sent...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

Intercompany Loan Treated As Constructive Distribution and Contribution

Heads I Win, . . . - When closely held corporations that are under common control engage in any intercompany transaction, it is prudent for the corporations and their shareholders to ensure that the transaction is being...more

Nothing Lasts Forever –Expiring Tax Provisions

The Long-Term View- Among its core functions, federal tax policy seeks to encourage those behaviors among businesses that, in the long run, will have a lasting positive effect upon the nation’s economy as a whole. ...more

Partnership Losses on Related Party Sales – The IRS Provides Some Clarification

Few individual owners of a closely held business would be surprised if you explained to them that the IRS and the Federal courts generally will subject many transactions between certain “related” persons to heightened...more

Taxes and the 2024 Election: ‘Tis the Season to Plan and Act

This is The End- I have dreaded the year end for as long as I can remember. As a teenager and then as a young adult I associated the final quarter of the year, and especially the period beginning on Thanksgiving 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

Activities Contrary to Public Policy – Revoking the Tax Exempt Status of Universities

It appears that many of the country’s colleges and universities believe they have not already contributed enough to the decline of American education and to the erosion of our society, generally. These institutions of...more

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

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

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

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

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