If you’re reading this post, you survived the Thanksgiving holiday – hopefully, without much family drama. Then again, there may have been moments, inspired by an overload of obligatory togetherness, that caused you to think...more
12/3/2025
/ Beneficiaries ,
Death Benefits ,
Income Taxes ,
Insurance Contracts ,
Insurance Industry ,
Insurance Regulations ,
Internal Revenue Code (IRC) ,
Investment ,
Life Insurance ,
Loans ,
Policy Terms ,
Reporting Requirements ,
Tax Code ,
Tax Court ,
Tax Litigation ,
Tax Returns ,
Taxation
It’s not at all unusual to encounter the owner of a New York business who dreams about leaving the State. The reasons often given for the desired move include, among others, the cost of doing business in New York, the State’s...more
11/25/2025
/ Audits ,
Business Entities ,
Department of Revenue ,
Domicile ,
Enforcement Actions ,
Florida ,
Income Taxes ,
New York ,
Non-Resident Income Taxes ,
Non-Residents ,
Penalties ,
State Taxes ,
Tax Appeals ,
Tax Audits ,
Tax Authority ,
Tax Liability ,
Tax Litigation ,
Tax Planning ,
Tax Returns ,
Taxation
An Extension of Credit -
When one person lends money to another, the lender expects the borrower to repay the loan by an agreed-upon time. In order to compensate the lender for the borrower’s use of the lender’s money (the...more
11/18/2025
/ Borrowers ,
Buyers ,
Contract Terms ,
Corporate Sales Transactions ,
Creditors ,
Debt Instruments ,
Deferred Payment Products ,
Earn-Outs ,
Income Taxes ,
Installment Agreements ,
Interest Income ,
Interest Rates ,
Internal Revenue Code (IRC) ,
Lenders ,
Loans ,
Merger Agreements ,
Payment Terms ,
Promissory Notes ,
Sellers ,
Settlement Agreements ,
Tax Liability ,
Tax Planning ,
Taxation ,
Trusts
The enactment earlier this year of the One Big Beautiful Bill Act (the “Act”)generated a fair amount of excitement in the business community.
If one had to identify a single provision of the Act in which the owners and...more
11/6/2025
/ Acquisitions ,
Business Ownership ,
Business Taxes ,
Capital Gains ,
Gain Exclusion ,
Income Taxes ,
Internal Revenue Code (IRC) ,
New Legislation ,
One Big Beautiful Bill Act ,
Popular ,
Qualified Small Business Stock ,
Small Business ,
Startups ,
Tax Exemptions ,
Tax Incentives ,
Tax Legislation ,
Tax Planning ,
Tax Reform ,
Taxation
It is axiomatic that a transaction between related businesses – i.e., businesses that are owned or controlled directly or indirectly by the same interests (a “controlled group”) – will generally be subject to heightened...more
10/22/2025
/ Arms Length Transactions ,
Controlled Foreign Corporations ,
Corporate Taxes ,
Corrective Actions ,
Cross-Border Transactions ,
Enforcement Actions ,
Foreign Subsidiaries ,
Income Taxes ,
Intangible Property ,
Intellectual Property Protection ,
Internal Revenue Code (IRC) ,
International Tax Issues ,
IRS ,
Tax Court ,
Tax Evasion ,
Tax Liability ,
Tax Litigation ,
Transfer Pricing
As part of its enforcement efforts, the IRS annually identifies what it describes as potentially abusive transactions that taxpayers should avoid. According to the agency, some of these transactions are focused on more...more
10/10/2025
/ Administrative Procedure Act ,
Disclosure Requirements ,
Enforcement Actions ,
Final Rules ,
Internal Revenue Code (IRC) ,
IRS ,
Judicial Review ,
Jurisdiction ,
Loans ,
Notice of Proposed Rulemaking (NOPR) ,
NPRM ,
Penalties ,
Proposed Rules ,
Reporting Requirements ,
Rulemaking Process ,
Statutory Interpretation ,
Tax Avoidance ,
Tax Scams
As we discussed a few weeks ago, the IRS is charged with enforcing the U.S. federal tax laws; i.e., it is responsible for processing tax returns and for collecting taxes. As part of its collection function, the agency may...more
10/2/2025
/ Fraud ,
Internal Revenue Code (IRC) ,
IRS ,
Statute of Limitations ,
Statutory Interpretation ,
Tax Advice ,
Tax Assessment ,
Tax Audits ,
Tax Court ,
Tax Evasion ,
Tax Fraud ,
Tax Liability ,
Tax Preparers ,
Tax Returns
Last week, an amicus brief was filed with the First Circuit Court of Appeals in support of a taxpayer’s challenge to the U.S. Tax Court’s dismissal of the taxpayer’s petition for lack of jurisdiction. The Tax Court determined...more
9/24/2025
/ Appellate Courts ,
Equitable Tolling ,
Filing Deadlines ,
Internal Revenue Code (IRC) ,
IRS ,
Jurisdiction ,
Litigation Strategies ,
Notice Requirements ,
Statute of Limitations ,
Statutory Interpretation ,
Tax Appeals ,
Tax Court ,
Tax Legislation
A quick review of the cannabis landscape reveals that most of the tax-related activity remains at the state level. At present, most states have decriminalized the use of cannabis products; it remains illegal in only a...more
9/19/2025
/ Cannabis-Related Businesses (CRBs) ,
Controlled Substances Act ,
Internal Revenue Code (IRC) ,
IRC Section 280E ,
IRS ,
Pass-Through Entities ,
Qualified Business Income ,
S-Corporation ,
Section 199A ,
Statutory Interpretation ,
Tax Court ,
Tax Deductions ,
Tax Litigation ,
Tax Planning ,
W-2
In the fictional world of John Wicks, the High Table enforces a strict code of conduct without which the lives of its inhabitants would mimic life in a Hobbesian state of nature.
However, as dangerous and as rule-bound as...more
9/12/2025
/ Appellate Courts ,
Equitable Tolling ,
Federal Taxes ,
Filing Deadlines ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Jurisdiction ,
Notice Requirements ,
Statute of Limitations ,
Statutory Interpretation ,
Tax Appeals ,
Tax Court ,
Tax Liability ,
Taxation
C Corp -
Imagine a closely held and growing start-up business (“Corp”) that was recently incorporated under state law and, so, is treated as a regular C corporation for purposes of the federal income tax.
Thus, Corp will pay...more
9/4/2025
/ C-Corporation ,
Capital Gains ,
Closely Held Businesses ,
Estate Planning ,
Estate Tax ,
Fair Market Value ,
Gift Tax ,
Grantor Trusts ,
Grantors ,
GST ,
Internal Revenue Code (IRC) ,
Popular ,
Private Company Shares ,
Qualified Small Business Stock ,
Shareholders ,
Small Business ,
Startups ,
Tax Planning ,
Taxation ,
Trusts
In the tax world, when someone refers to a “charitable” organization, it is likely they are using the term in its generally accepted legal sense to include not-for-profit corporations or charitable trusts that are organized...more
8/13/2025
/ 501(c)(3) ,
Charitable Organizations ,
Excise Tax ,
Executive Compensation ,
Exemptions ,
New Legislation ,
Nonprofits ,
Private Foundations ,
Public Charities ,
Tax Cuts and Jobs Act ,
Tax Deductions ,
Tax Exemptions ,
Unrelated Business Income Tax
In the months preceding the general election in 2024, the owners of many closely held businesses who had not yet given much thought to the disposition of their future estates, including their businesses, decided they should...more
8/1/2025
/ Business Succession ,
Closely Held Businesses ,
Estate Planning ,
Estate Tax ,
Family Businesses ,
Generation-Skipping Transfer ,
Gift Tax ,
New Legislation ,
One Big Beautiful Bill Act ,
Succession Planning ,
Tax Cuts and Jobs Act ,
Tax Planning ,
Tax Reform ,
Transfer Taxes ,
Trusts
New York’s personal income tax law, like that of other states, conforms with the federal system of income taxation. The reason typically given for such conformity is to simplify tax return preparation, improve compliance and...more
7/24/2025
/ Audits ,
Compliance ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Like Kind Exchanges ,
Limited Liability Company (LLC) ,
New York ,
Partnerships ,
Real Estate Transactions ,
Section 1031 Exchange ,
State Taxes ,
Tax Liability ,
Tax Planning ,
Tax Returns ,
Taxation
The “One Big Beautiful Bill Act” (the “Act”) was signed into law last week, on July 4. As promised by the White House, the Act extends – i.e., purports to make “permanent” – many of the otherwise expiring provisions that were...more
7/14/2025
/ Business Taxes ,
Closely Held Businesses ,
Estate Tax ,
Federal Taxes ,
Gift Tax ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
New Legislation ,
One Big Beautiful Bill Act ,
Partnerships ,
Qualified Small Business Stock ,
Small Business ,
Tax Cuts and Jobs Act ,
Tax Deductions ,
Tax Legislation ,
Tax Planning ,
Tax Reform ,
Tax Returns
Last week the United States celebrated the 249th anniversary of its declaration of independence from Great Britain. In celebration of the occasion, President Trump signed into law the One Big Beautiful Act which, among other...more
7/9/2025
/ Constitutional Challenges ,
Imports ,
Income Taxes ,
New Legislation ,
Sixteenth Amendment ,
Statutory Interpretation ,
Tariffs ,
Tax Cuts and Jobs Act ,
Tax Policy ,
Tax Reform ,
Taxation ,
Trump Administration ,
U.S. Treasury
If you’ve been around closely held businesses long enough, you know that a transfer of money between a business and its owner, or between two related businesses, is sometimes characterized by the parties as a loan (“related...more
6/23/2025
/ Appeals ,
Borrowers ,
Cancellation of Debt (COD) ,
Closely Held Businesses ,
Corporate Taxes ,
Creditors ,
Debt Collection ,
Debtors ,
Income Taxes ,
IRS ,
Loans ,
Related Parties ,
Statutory Interpretation ,
Tax Court ,
Tax Deductions
An Agency Under Siege -
The mission statement of the IRS reminds taxpayers that it is their responsibility to understand and meet their tax obligations, while it is the role of the IRS to “enforce the [tax] law with...more
6/11/2025
/ Corporate Taxes ,
Estate Tax ,
High Net-Worth ,
Income Taxes ,
Inflation Reduction Act (IRA) ,
Internal Revenue Code (IRC) ,
Investment ,
Investment Funds ,
Investment Management ,
IRS ,
Limited Partnerships ,
Partnerships ,
Private Equity ,
Self-Employment Tax ,
Statutory Interpretation ,
Tax Court ,
Tax Liability ,
U.S. Treasury
Every conveyance of property or of an interest in property from one person to another is prompted, or at least influenced, by economic considerations. The parties to the transaction may swap properties, or one party may...more
5/29/2025
/ Estate Tax ,
Gift Tax ,
Grantor Trusts ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Partnerships ,
Property Tax ,
Property Transaction Taxes ,
S-Corporation ,
Shareholders ,
Tax Deductions ,
Tax Liability ,
Tax Planning ,
Taxable Income ,
Taxation ,
Termination ,
Transfer Taxes ,
Trust Distributions ,
Trusts
Last month, Bloomberg carried an article about a “small but growing trend” of states that are either cutting their individual income taxes or phasing them out entirely.
According to the article, the states adopting these...more
4/29/2025
/ Appeals ,
Business Entities ,
Capital Gains ,
Corporate Taxes ,
Income Taxes ,
Non-Residents ,
S-Corporation ,
Shareholders ,
State Taxes ,
Tax Liability ,
Taxation
Few provisions of the Code have a single, clear meaning that leaves no room for interpretation. Even many of those that, on the surface, appear fairly straightforward, are usually open to alternative “understandings.”...more
4/11/2025
/ 501(c)(3) ,
Charitable Organizations ,
Employer Liability Issues ,
Employment Tax ,
Enforcement ,
Enforcement Actions ,
Internal Revenue Code (IRC) ,
Nonprofits ,
Penalties ,
Tax Exemptions ,
Tax Liability
A parent will sometimes transfer money to a child to enable the child to make an investment that the child could not otherwise make on their own. For example, the child may have identified an attractive business opportunity...more
4/1/2025
/ Borrowers ,
Estate Tax ,
Fair Market Value ,
Gift Tax ,
Interest Rates ,
Internal Revenue Code (IRC) ,
Investment ,
IRS ,
Loans ,
Tax Court ,
Tax Liability ,
Tax Planning ,
Trusts
Charitable organizations are dependent, in no small part, upon the financial support of many successful business owners. The generosity of these individuals and their organizations may be a manifestation of several factors...more
3/21/2025
/ Business Ownership ,
Charitable Organizations ,
Closely Held Businesses ,
Compliance ,
Estate Planning ,
Family Businesses ,
Internal Revenue Code (IRC) ,
IRS ,
Partnerships ,
Private Foundations ,
Tax Avoidance ,
Tax Deductions ,
Tax Planning
According to the New York City Comptroller, the City collected approximately $1.13 billion in Real Property Transfer Tax (“RPTT”) in the FY 2024. The Comptroller’s Office has forecast that $1.21 billion of RPTT will be...more
2/27/2025
/ Charitable Organizations ,
City of New York ,
Exempt Organizations ,
Limited Liability Company (LLC) ,
Nonprofits ,
Real Estate Transactions ,
Real Estate Transfers ,
Tax Exempt Entities ,
Tax Exemptions ,
Tax Liability ,
Transfer Taxes
Late last year, the Office of the State Comptroller (the “OSC”) estimated that sales and use tax receipts would increase by 2.3% in the SFY 2024-2025. The OSC also projected that collections from sales and use taxes would...more
2/18/2025
/ Appeals ,
Audits ,
Business Entities ,
Compliance ,
Corporate Governance ,
Corporate Misconduct ,
Delinquency Status ,
New York ,
Noncompliance ,
Penalties ,
Personal Liability ,
Sales Tax ,
Shareholders ,
State and Local Government ,
State Taxes ,
Tax Liability ,
Tax Returns ,
Taxation