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Crossing the Streams[i]

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 such instance in which the IRS was asked to determine the tax consequences of certain transfers of stock by an individual shareholder of the issuing corporation and by the trusts created for the benefit of the shareholder’s family.[ii]  

Before describing these transactions, it may be helpful to briefly review some of the applicable tax principles.

Continue Reading Transfers Within the Family Business: Gifts or “Ordinary Course” Transactions?
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What Corporate Shield?

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 corporations?

I, for one, would not. Over the years, I have both experienced and read about many situations in which shareholders realized too late that the “limited liability” protection the corporate shield affords them under a state’s business corporation law goes only so far, even in cases where the corporation is respected as a separate legal entity.[i]

Continue Reading Shareholder-Transferee Liability for a Corporation’s Income Tax
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Passing the Torch

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 established in the business, some of them may want to assume greater managerial responsibility and to have a greater voice in strategic planning; inevitably, the children become eager to realize a greater share of the economic success enjoyed by the business which they may insist is attributable to their efforts; they want to become owners.[i]

Continue Reading The Family-Owned Business, Stock Options, And Personal Goodwill – a Smorgasbord of Tax Issues
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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 undertaken for a bona fide business reason. It is also important that the form of the transaction, and the parties’ intent for engaging in such transaction, as manifested by its form or structure,  be consistent with the income tax consequences arising therefrom as reported by each of the parties.   

Continue Reading Intercompany Loan Treated As Constructive Distribution and Contribution
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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.[i]

Implicit in this approach toward tax legislation is the enactment of a set of relatively constant and long-lasting rules on which businesses[ii] may rely when planning for the future.

Under this long-term view of tax policy, a provision that is drafted to be short-lived probably should not be adopted unless Congress reasonably determines the provision will generate benefits that endure well beyond its expiration.  

Continue Reading Nothing Lasts Forever –Expiring Tax Provisions
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Related Party Transactions

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 scrutiny (a) to ensure that the related persons have not structured a transaction to gain a tax advantage without also having a bona fide business purpose, or (b) to ascertain whether the intended economic consequences of the transaction are consistent with its form and with how it is reported by the parties for tax purposes.   

However, those same individuals may be taken aback if you described to them some of the measures that Congress has enacted over the years to prevent related persons from realizing certain tax benefits that Congress has determined would be inappropriate in the context of a transaction between related parties.  

Continue Reading Partnership Losses on Related Party Sales – The IRS Provides Some Clarification
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Hide and Seek

A national study released in 2015 reported that “nearly half the residential purchases of over $5 million were made by shell companies rather than named people.”[ii] Because shell companies could often be formed without disclosing the individuals that ultimately owned or controlled them (i.e., their beneficial owners), and could be used to conduct financial transactions without disclosing their true beneficial owners’ involvement, there was a concern that criminals were using such vehicles to launder money through the purchase of real estate and thereby hide, or at least obscure, the illicit origin of their funds. The report explained that many of these purchases were made in all-cash transactions; thus, no lender was involved and, so, the usual due diligence that accompanies a loan application was avoided.[iii]  

Continue Reading NY’s LLC Transparency Act and NYC Real Estate – Albany Wants to Know the Secrets that You Keep[i]
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This is The End[i]  

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 ending on New Year’s Eve, with completing final exams and papers.[ii] After graduating from law school, but being inexperienced with the business of business, I naively hoped that the blues and the anxiety that I had experienced every year during that time of year were finally behind me. Not so.

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

The Office of the New York State Comptroller just released a new report that examines taxpayer migration trends during the pandemic.[i] The report, which builds on an earlier analysis of pre-pandemic taxpayer migration trends, reveals there was much more movement out of the State than was thought initially.

During that period, on a net basis, out-migration from New York skyrocketed, due largely to those leaving New York City; over one in every 100 resident filers left the State. By the end of the period, out-migration rates for families remained much higher than pre-pandemic levels, with married filers leaving at substantially higher rates. The total number of New York’s personal income tax filers declined for the first time since the Great Recession.

Continue Reading New York Can Be Stingy Giving Credit – Resident Tax Credit, That Is
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Mixing Holidays With Business

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 Dis-Union with family or friends. Then there were some who, having overheard in the midst of the merrymaking how someone else had implemented what sounded like a wonderful tax-saving strategy, resolved to do the same themselves for 2024.[i]

Continue Reading The Family Business – Compensating Family-Employees