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?

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

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

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

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

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 customer base. Such “smart” growth will attract talented employees to the business, facilitate borrowing, prepare the business to withstand economic downturns, and make it more attractive to potential buyers.Continue Reading Disclaiming to Save Taxes

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 28-percent larger than it was in 2022.[i]

The CBOs’ report attributed the increase to a combination of lower revenues and higher outlays. Can you guess which expenditure was among those most responsible for the increase? If you said payments of interest on the federal debt, you were right.Continue Reading Debtor Corp’s S Election: “Property” in Bankruptcy?

Ups and Downs

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 business’s employees feel secure in their position; hopefully, they also feel valued.

This rosy picture can change rather quickly, however, when the overall economy, or the industry in which the business operates, experiences a downturn.[i]Continue Reading The Trust Fund Penalty – Times May be Tough, But Don’t “Borrow” from Withheld Taxes

Another Mess

Congress has only a few days to avert a “shutdown” of the federal government.[i]

It’s not looking good in the House, as Speaker McCarthy has struggled to bring certain members of the majority into line, while more moderate members of his party have displayed a willingness to reach across the aisle to secure a temporary funding bill.[ii]

Meanwhile, it seems that the members of the minority[iii] have been content to watch the GOP’s drama unfold.Continue Reading Open Transaction Treatment for The Liquidation of a Partner’s Interest

Toll the Bells

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 members.[i]

For example, there are no restrictions on (i) the ownership of equity in an LLC, (ii) the number of members it may have, and (iii) the varying classes of economic interests it may issue its members and its ability to specially allocate items of income, gain, loss and deduction.[ii] In addition, the LLC is treated as a pass-through for federal income tax purposes; it does not pay an entity-level tax on its taxable income – instead, such income is reported by and taxed to its members.[iii]Continue Reading ESBTs and the Carryover of S Corporation Losses