Business

Can It Get Worse?

I’m certain that most of us were disappointed with the Appellate Department’s decision last week in Prof. Zelensky’s continuing dispute with New York over its application of the notorious “convenience of the employer” test;[i] disappointed, but not entirely surprised.[ii]

One can still hope that the Courts will one day become less deferential toward the tax folks in Albany.

Continue Reading Applying New York’s Convenience Rule to a Former Resident, Truly Remote Non-Resident Employee

Here It Comes

According to many, the long-awaited intergenerational transfer of assets from the Baby Boomer generation, and from what remains of the Silent Generation, to younger members of their families[i] – estimated by some to exceed $100 trillion in total, worldwide, over the next two decades – is well under way.

Most of this shift in wealth will occur within families whose members already count themselves among the wealthiest on the planet.[ii] Indeed, according to one source, “[t]he wealthiest 10 percent of households will be giving and receiving a majority of the riches.” Within that group, the top 1 percent holds about as much wealth as the bottom 90 percent, and it “will dictate the broadest share of the money flow.”[iii]

Continue Reading With Tax Increases Lurking Just Over the Horizon, and With Large Dispositions of Wealth Underway, Now’s the Time to Identify and Correct Earlier Missteps

Personal Use

“But it’s mine!”

That’s not some toddler speaking.

You’ve just advised an entrepreneurial client for the “Nth” time that they should not treat the corporation[i] they control, and out of which they operate their business, as their personal bank account.

Such behavior may jeopardize the limited liability protection that the corporate shield would otherwise afford a shareholder. It may also expose the shareholder to unexpected and unwelcome income tax consequences, as we’ll see shortly.

Continue Reading If I Own the Corp, and the Corp Owns the Assets of the Business, Aren’t  Those Assets Mine?

State of the Economy?

According to statistics released by the Administrative Office of the U.S. Courts for the twelve-month period ending Dec. 31, 2025, bankruptcy filings by businesses rose 7.1 percent and non-business filings increased by 11.2 percent. Total filings have increased each quarter since June 2022, though they remain lower than historical highs.[i]

Do these statistics somehow reflect the state of the U.S. economy, generally?

Continue Reading No Matter How Bad it Gets . . . Pay Your Withholding Taxes?

C’mon Already

New York has once again missed its April 1 budget deadline, in no small part because the Governor’s party, which controls both the State Senate and Assembly,[i] is once again at odds with the Governor over tax policy.

The Legislature is pushing for tax increases on businesses and on high earners, while the Governor opposes raising the personal income tax but is willing to extend the “temporary” increase in the top tax rate for corporations.[ii]

Continue Reading The “Mandated” New York S Corporation Election – Does Investment Income Include Gain from the Sale of Goodwill?

The Struggling Business

When things start to go badly in a business, its owners may feel compelled to take certain extraordinary, and usually ill-conceived, measures “to keep the doors open and the lights on.”

For instance, when faced with a reduction in positive cashflow,[i] the owner may decide to forgo the remittance of sales taxes or employment taxes properly withheld by the business,[ii] or the payment of other taxes owed by the business, and instead divert such funds toward the payment of business expenses.

It’s an old story. The owner of the business acknowledges their failure to satisfy its tax obligations, and recognizes that serious consequences may result therefrom. Still, the owner will rationalize their decision to forgo payment by convincing themselves that once the business has turned the proverbial corner, it will discharge whatever taxes may be owing at that time (plus interest and any penalties).

Continue Reading A Corporation’s Loss of Capacity and the Tax Court’s Jurisdiction

The Tax Court has previously held that a partner who contributes his own note to a partnership in exchange for a partnership interest takes no basis in the interest and their capital account is not credited for the value of the contribution. 

In the case discussed below, an entity that was disregarded for purposes of the income tax received a promissory note from its sole owner, which it then contributed to a newly formed partnership in exchange for an interest in that partnership.[i]

What followed was not intended by the parties.

Continue Reading Unforeseen Tax Consequences Arising From an Elective Change in Entity Classification

Abusing Partnerships?

I am certain that most of you have encountered at least one unscrupulous “advisor” who tried to convince you or your client to take advantage of what they described as a perfectly legal “loophole” in the Code that could generate significant tax savings.[i]  

Over the years, many of these aggressive tax “planning” strategies have utilized the partnership form of business entity[ii] to claim the “as advertised” tax benefits but without demonstrating any independent business or investment purpose for the partnership.

Continue Reading Determining Whether a “Partnership” Should Be Respected For Tax Purposes

LLCs Run Through It

What do you think of when someone mentions Montana? Is it the seemingly boundless landscape from which the largest land-locked state[i] derived its nickname, Big Sky Country?[ii] What about its Rocky Mountain national parks, like Glacier or Yellowstone?[iii]

Until recently, I had always equated Montana with rugged landscapes, honest outdoor living,[iv] flyfishing,[v] and my grandfather.[vi]

Of late, however, Montana, or more accurately, the use of Montana LLCs, has become synonymous with sales tax avoidance (or worse).

Continue Reading Sales Tax Savings With Montana LLCs? Don’t Do It

From Taxable to Tax-Exempt Corp

Travel back with me to 1986, if you will, and the repeal of the General Utilities doctrine. The Tax Reform Act of 1986[i] added Sec. 337(d) to the Code and directed the Treasury to prescribe the regulations necessary to carry out the purposes of the doctrine’s repeal.[ii]

The Technical and Miscellaneous Revenue Act of 1988 amended Sec. 337(d) to specify that the section authorizes regulations to “ensure that these purposes shall not be circumvented * * * through the use of a * * * tax-exempt entity.”

Continue Reading Converting a Taxable Corp Into a Tax-Exempt Entity Via a Bargain Sale – or is it Something More?