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The Hobby-Loss Grouping Rules

The IRS is not a government agency. It does not have to earn a profit. It does not even have to be concerned about keeping basic books and records. Unlike the standard that it imposes on even the...

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The Hobby Loss Rules: Planning for Unprofitable Businesses

American culture still has a hint of the protestant work ethic. There are people in the United States who still work hard and are willing to take risks to make things happen. The country benefits if...

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Bad Debt Deduction Not Allowed Until Business Fails

If you lend money to a failing business and the business eventually fails, can you take a bad debt deduction?  And if so, when?  The U.S. Tax Court addressed this in Cooper v. Commissioner, 143 T.C....

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Tax Deductions for Hobby Survives IRS Scrutiny

There are quite a few cases where the IRS disallowed loss deductions for “hobbies.” There are also quite a few cases where the courts have upheld the IRS’s position. These cases are decided based on...

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Grouping Nonpassive Activities Under the PAL Rules

Taxpayers are often surprised to learn that some losses may not be netted against gains in the current tax year. This is often due to the passive activity loss and material participation rules. The IRS...

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Is a Bad Debt Deduction Triggered by Cease-and-Desist Court Order

Determining the allowable tax year for a loss is a common challenge for taxpayers, often relying on identifying a triggering event. There is very little guidance as to what can qualify as a triggering...

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Bad Credit Results in No Bad Debt Deduction

When it comes to taking a bad debt deduction, the IRS tends to scrutinize more closely, especially if the loan is from a friend or family member. The courts have developed various factors that they...

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Subchapter S Corporation Losses Limited by Tax Basis

One of the benefits of Subchapter S corporations is the ability to have losses flow through from the business’ tax return to the individual shareholder’s tax return. These flow-through losses are...

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Facts Needed to Support a Bad Debt Deduction

When taxpayers claim a deduction for a bad debt, it can trigger an audit by the IRS. The IRS has a vested interest in ensuring that taxpayers are not taking advantage of tax laws to reduce their tax...

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IRS Rejects Court’s Passive Activity Loss 5% Owner and Grouping Decision

The passive activity loss (“PAL”) rules can limit the ability to deduct losses from passive activities, such as rental losses.  The real estate professional and activity grouping rules can allow...

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A Partnership is Worth Less, Not Entirely Worthless

The complexities surrounding tax loss deductions can be particularly challenging for taxpayers. While claiming tax losses for worthless securities may seem like a straightforward process, the IRS often...

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Documenting Tax Losses for Worthless Securities

tax loss for a worthless security, taxpayers must document the loss and establish several key elements. These elements include proving the existence of the security, the amount invested in the...

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Is Election to Waive NOL Carryback Irrevocable?

You have to be careful when electing to waive the right to carry back a net operating loss. This is particularly true if there are items on your tax returns from earlier years that the IRS may...

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Bad Debt Deduction for Real Estate Lender for Non-Real Estate Loan

In the world of finance and investing, making loans is often seen as a relatively safe way to earn a higher rate of return than other investment opportunities. For many individuals, this means...

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Avoiding Hobby Loss Limits for Long-Term Projects

Long-term projects often lose money. They often do so for several years. This is the result of a project that needs capital to build infrastructure or to develop a new market or to capture market...

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Bad Debt Tax Deduction for Guarantee Payment?

When an individual or company guarantees a loan for a third party, they are essentially agreeing to assume responsibility for the debt if the borrower defaults on their payments. In some cases, the...

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Tax Planning for the Start-up Limitation Rules

Our tax laws include start-up rules that limit the ability to deduct certain business and investment expenses. For business owners and investors with other sources of income, this can result in funds...

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Can “Business Synergies” be an Asset that Increases a Tax Loss?

The tax consequence of a transaction often depends on how one characterizes or describes the transaction. Business synergies are often cited as the rationale for merger and acquisition deals. In a...

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Tax Loss Planning: The At-Risk Rules

Are you purchasing a business or real estate that involves financing a business or investment that is likely to produce tax losses in the future? Or have you already made the purchase? If so, there may...

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Hobby Loss vs. Start-Up Expense?

Just about every business starts out with losses. This is the nature of start-ups. The activity will either gain traction and produce income and possibly a profit or, eventually, the activity end. This...

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