At the beginning of every year, the IRS informs the public of those tax matters on which the IRS will not issue letter rulings. Typically, these are areas of the tax law that are under study at the IRS, and that the IRS hopes to address through the publication of a revenue ruling, a
Oh No! Valuation Discounts Under Siege?
Dr. Peter Venkman: This city is headed for a disaster of biblical proportions.
Mayor: What do you mean, “biblical”?
Dr Ray Stantz: What he means is Old Testament, Mr. Mayor, real wrath of God type stuff.
Dr. Peter Venkman: Exactly.
Dr Ray Stantz: Fire and brimstone coming down from the
Tax Free? That’s Not What I Wanted.
Silly Question?
“Which do you prefer: a taxable or a non-taxable transaction?”
Most taxpayers would probably respond that they prefer a non-taxable transaction. After all, who wants to pay tax if they don’t have to?
Closer analysis, however, may reveal that given a particular taxpayer’s situation, a taxable transaction may yield a better result.
Don’t Be Passive About Losing the “S” Election
They’re Still Here
Once upon a time, before the advent of limited liability companies (“LLCs”), taxpayers would occasionally acquire real property in a corporation rather than in a limited partnership.
The corporation may have been created to hold the real property, or it may have been an operating company that, for some misguided reason, decided
The Disgruntled Shareholder & “Breaking” the S Election, Part I
During the course of the year, we encounter a number of shareholder disputes. Sometimes we represent a minority shareholder; sometimes we represent the corporation or the majority shareholders. 
Regardless of who the players are, the resolution of the dispute will involve some economic deal. The economic deal, in turn, will depend in no small part
Treat It Like A Loan
For most closely-held businesses, and especially for those that are newly-formed, the infusion of capital is of paramount concern because it may be needed to fund start-up costs, operations and, eventually, expansion. In some cases, the capital may be obtained from investors in exchange for an equity interest in the business; in others, the capital
Captive Insurance, Part II: Application
In yesterday’s post, we provided an overview of captive insurance entities. Today, we will consider the specific facts of two different so-called captives, and whether or not they qualified as such according to the Tax Court and the IRS, respectively.
The Captive Arrangement in the Tax Court
In Rent-a-Center v. Commissioner, the Court
Increased Complexity? Not Enough to Get Past the IRS.
A recent decision touched upon a theme that has been considered in several of our blogs: the “substance over form” doctrine, under which the legal form of a transaction – that would otherwise result in a beneficial tax result for a taxpayer – will be disregarded in order to give effect to its “true”
Selling a Family Asset: It Makes Business Sense– Will the IRS Care?
Here We Go Again
It is a common theme of these posts that a transaction has to make sense from a business perspective, that it should not be undertaken primarily for tax purposes, and that the goal of tax planning should be to maximize the economic benefit of the transaction by reducing the resulting tax
Shareholder Buy-Outs In A Closely-Held Corp: Part II
Our last post examined what are commonly thought of as the most “direct” income tax consequences arising from a the buy-out of a departing shareholder by way of a cross-purchase or redemption of his or her shares. However, there are a number of other tax consequences to be considered that are no less direct, and