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
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
Many successful business owners attribute some part of their success to their community. For some of these owners, it is not enough to simply acknowledge this “debt”; they feel an obligation to share some of their financial...more
2/10/2025
/ Business Entities ,
Charitable Organizations ,
Compliance ,
Corporate Governance ,
Donations ,
Enforcement Actions ,
Internal Revenue Code (IRC) ,
IRS ,
Limited Liability Company (LLC) ,
Loans ,
Nonprofits ,
Private Foundations ,
Tax Exempt Entities ,
Tax Liability ,
Tax Planning
If you’ve worked with the owners of closely held businesses for even just a few years, you have realized they are only half joking when they complain about having the government as a partner. Consider how much federal, state,...more
1/28/2025
/ Business Entities ,
Business Ownership ,
Closely Held Businesses ,
Enforcement ,
Enforcement Actions ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Limited Liability Company (LLC) ,
Partnerships ,
Tax Court ,
Tax Liability ,
Tax Planning ,
Tax Returns ,
Withholding Tax
Just a few weeks ago, many individual taxpayers, driven by what they viewed as the relatively imminent expiration of the enhanced federal transfer tax exemptions, sought advice on how to leverage their remaining exemption and...more
1/14/2025
/ Estate Planning ,
Estate Tax ,
Federal Taxes ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Limited Liability Company (LLC) ,
Limited Partnerships ,
Partnerships ,
Tax Exemptions ,
Tax Liability ,
Tax Planning ,
Tax Returns ,
Trusts
How was your Thanksgiving? I hope you celebrated the holiday in a pleasant setting with folks whose company you enjoyed, and with plenty of good food. I hope you participated in some interesting conversations or joined in...more
12/11/2024
/ Beneficiaries ,
Exemptions ,
Generation-Skipping Transfer ,
Gifts ,
Grantors ,
Irrevocable Trusts ,
IRS ,
Modification ,
Private Letter Rulings ,
Probate Courts ,
Taxable Income ,
Transfer Taxes ,
Trust Distributions ,
Trusts
Earlier this year the IRS announced that, as part of its larger compliance efforts begun last fall under the Inflation Reduction Act, the agency’s stepped-up enforcement activity with respect to high wealth, high income...more
10/31/2024
/ Audits ,
Compliance ,
Debt Collection ,
Deficiency Notices ,
Documentation ,
Due Process ,
Inflation Reduction Act (IRA) ,
IRS ,
Overpayment ,
SCOTUS ,
Solicitor General ,
Statute of Limitations ,
Tax Appeals ,
Tax Court ,
Tax Debt ,
Tax Levy ,
Tax Liability ,
Tax Returns
As we will see shortly, it is often “better to give than to receive,” though this statement begs the obvious question of whether it is better to do so during one’s lifetime or upon one’s death.
Many well-to-do individuals...more
10/11/2024
/ Clawbacks ,
DSUEA ,
Estate Planning ,
Estate Tax ,
Estate-Tax Exemption ,
Exclusions ,
Gift Tax ,
Gift-Tax Exemption ,
Grantor Retained Annuity Trusts (GRATs) ,
Grantor Trusts ,
GST ,
Holding Periods ,
IRS ,
Portability ,
Sunset Provisions ,
Tax Cuts and Jobs Act ,
Tax Exemptions
You may recall that earlier this year the IRS launched an initiative to pursue 125,000 “high-income, high-wealth” taxpayers who have not filed taxes since 2017. These were cases where the IRS received third party information...more
9/18/2024
/ Bank Secrecy Act ,
Citizenship ,
Civil Forfeiture ,
Excessive Fines Clause ,
Failure-to-File ,
FBAR ,
Foreign Bank Accounts ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Reporting Requirements ,
Tax Appeals ,
Tax Avoidance ,
Tax Debt ,
Tax Penalties ,
Taxable Income ,
Voluntary Compliance ,
Voluntary Disclosure ,
Willful Violations
If given their druthers, most transactional corporate attorneys would prefer to spend their day practicing “happy law,” by which they typically mean transactions that involve capital formation, mergers and acquisitions, joint...more
8/20/2024
/ Board of Directors ,
CEOs ,
CFOs ,
Corporate Dissolution ,
Deficiency Notices ,
Embezzlement ,
IRS ,
K-1 ,
Misappropriation ,
S-Corporation ,
Settlement Agreements ,
Shareholder Distributions ,
Shareholders ,
State Courts ,
Stock Transfer ,
Tax Returns ,
Taxable Income ,
Whistleblowers
There is no denying that many parts of the Code are complex and, in some cases, too obscure for many “laypersons” to comprehend. Over time, this reality spawned the need for advisers who are both knowledgeable and experienced...more
8/12/2024
/ Business Expenses ,
Capital Gains ,
Fair Market Value ,
Foreign Persons ,
Internal Revenue Code (IRC) ,
IRS ,
Limited Liability Company (LLC) ,
Non-Resident Aliens ,
Partnership Interests ,
Tax Cuts and Jobs Act ,
Tax Deductions ,
Taxable Income
Over the last couple of years, several of my friends have become citizens of the country from which their parents emigrated to the U.S. Also during that period, some acquaintances took advantage of the so-called “golden...more
7/26/2024
/ Citizenship ,
Exit Tax ,
Foreign Corporations ,
Foreign Investment ,
Golden Visa ,
Green Cards ,
Income Taxes ,
Investment Property ,
IRS ,
Like Kind Exchanges ,
Real Estate Investments ,
Replacement Properties ,
Tax Liability ,
Tax-Deferred Exchanges
Having been swept along for nine days “by the force of the hostile winds on the fishy sea,” Odysseus and his crew came to a strange land. After securing their ships, Odysseus sent some of his “companions ahead, telling them...more
7/18/2024
/ Agribusiness ,
C-Corporation ,
Cannabis Products ,
Controlled Substances ,
Controlled Substances Act ,
DEA ,
Decriminalization of Marijuana ,
Drug Trafficking ,
Illegal Activity ,
Income Taxes ,
IRS ,
Marijuana ,
Marijuana Related Businesses ,
Plant Based Products ,
Recreational Use ,
S-Corporation ,
Schedule I Drugs
In less than four months, the citizens of the United States will be electing their next President to a four-year term. They will also be deciding which of the two major political parties will “control” the Senate, the House,...more
7/11/2024
/ Apportionment ,
C-Corporation ,
Conservatives ,
Controlled Foreign Corporations ,
Foreign Corporations ,
IRS ,
Moore v US ,
Partnerships ,
Pass-Through Entities ,
Presidential Elections ,
Repatriation ,
S-Corporation ,
SCOTUS ,
Shareholders ,
Sixteenth Amendment ,
Tax Cuts and Jobs Act ,
Tax Deferral ,
Tax Liability ,
Term Limits
You may have heard or even read about the U.S. Supreme Court’s recent decision regarding the date of death value of a deceased shareholder’s shares in a closely held corporation that owned a life insurance policy on the...more
7/1/2024
/ Business Succession ,
Buy-Sell Agreements ,
Buyouts ,
Certiorari ,
Closely Held Businesses ,
Connelly v United States ,
Estate Tax ,
Fair Market Value ,
IRS ,
Liability ,
Life Insurance ,
Liquidity ,
Redemption Agreement ,
Right of Redemption ,
SCOTUS ,
Shareholders ,
Tax Audits
It is a basic principle of the income tax that the gain or loss realized by a taxpayer from the conversion of property into cash, or from the exchange of property for other property that differs materially in kind from the...more
6/11/2024
/ Beneficiaries ,
Capital Gains ,
Corporate Restructuring ,
Equity Investors ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Like Kind Exchanges ,
Limited Liability Company (LLC) ,
Liquidation ,
Partnerships ,
Property ,
Reorganizations ,
Shareholders ,
Tenancy-in-Common ,
Transfer of Assets ,
Trustees ,
Trusts ,
Wills
An anonymous thinker, lost to history, is credited with having said that the unofficial motto of the IRS is, “We have what it takes to take what you have.” In some instances, the truth of the above statement is manifested in...more
5/30/2024
/ Alter Ego ,
Appeals ,
Audits ,
Bad Actors ,
Bank Accounts ,
Capital Gains ,
Deficiency Notices ,
Income Taxes ,
IRS ,
S-Corporation ,
Sole Proprietorship ,
Summary Judgment ,
Tax Avoidance ,
Tax Court ,
Tax Liability ,
Tax Liens
Earlier this year, the OECD observed there has been a significant increase in global wealth inequality over the last two decades. It also acknowledged that “taxation is a key instrument . . . that governments have at their...more
5/16/2024
/ Audits ,
Capital Gains ,
Federal Budget ,
Foreign Governments ,
Inflation Reduction Act (IRA) ,
IRS ,
Net Investment Income ,
OECD ,
Presidential Elections ,
Surtax ,
Tax Authority ,
Tax Avoidance ,
Tax Increases ,
Tax Liability ,
United Nations ,
Wealth Tax ,
Whistleblowers
Assume that X and Y agree to the following: X will transfer ownership of Prop to Y, and Y will transfer cash to X.
What just happened? Obviously, X has sold Prop to Y. If the amount of cash that X receives is greater than...more
5/6/2024
/ Anti-Abuse Rule ,
Disguised Sales ,
Equity Partners ,
Financial Transactions ,
Income Taxes ,
Internal Revenue Code (IRC) ,
Investment ,
Investment Adviser ,
IRS ,
Limited Liability Company (LLC) ,
Membership Interest ,
Partnership Distributions ,
Partnership Interests ,
Partnerships ,
Promissory Notes ,
Suppliers ,
Tax Avoidance ,
Tax Court
Over the years, I have observed there is only one thing that a taxpayer fears more than being notified by the IRS that their income tax return for a particular taxable year has been selected for audit, and that is being...more
4/24/2024
/ Audits ,
Court of Federal Claims ,
Debt Collection ,
Deficiency Notices ,
Filing Deadlines ,
Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Lack of Jurisdiction ,
Petition for Writ of Certiorari ,
Redeterminations ,
SCOTUS ,
Tax Court ,
Tax Penalties ,
Tax Returns
Imagine the IRS notifies Taxpayer that they have an outstanding tax liability with respect to Tax Year, and that the agency intends to levy on Taxpayer’s property to collect the allegedly unpaid tax. Taxpayer challenges the...more
4/19/2024
/ Income Taxes ,
Internal Revenue Code (IRC) ,
IRS ,
Overpayment ,
Popular ,
Spouses ,
Tax Appeals ,
Tax Court ,
Tax Debt ,
Tax Levy ,
Tax Liability ,
Tax Refunds ,
Tax Returns
As we approach the deadline for paying federal individual income taxes and, generally, for filing the returns on which such taxes are determined, some of you may be recalling how the Inflation Reduction Act of 2022...more
4/11/2024
/ Administrative Law Judge (ALJ) ,
Attendance ,
Compensation & Benefits ,
Federal Employees ,
Income Taxes ,
Inflation Reduction Act (IRA) ,
Internal Revenue Code (IRC) ,
IRS ,
Misleading Statements ,
Paid Time Off (PTO) ,
Performance Reviews ,
Privately Held Corporations ,
Sick Leave ,
Surveillance ,
Tax Returns ,
Termination ,
Treasury Inspector General for Tax Administration (TIGTA) ,
U.S. Treasury