Do you operate your business as a corporation, a partnership, or a proprietorship, or as an LLC taxed as one of these three entities? Your choice of entity impacts whether you can create a no-hassle, tax-free fringe benefit for you and/or your employees’ smartphones. In this article, you learn the rules that apply and which ones give you the best benefits.

Don’t let tax deadlines catch you off guard! Stay organized and save more with our 2024 Federal Tax Calendar for small businesses and self-employed taxpayers. Download your calendar now!

Proposed IRS regulations scheduled to go into effect for the 2025 tax year will require people and companies that help customers transfer digital assets such as Bitcoin to file a new Form 1099-DA with the IRS. This form reports information similar to that reported for stock sales, such as sales proceeds, as well as (starting in 2026) tax basis and gains and losses. The new reporting rules will apply to digital asset trading platforms, payment processors, many wallet providers, and other “digital asset brokers.”

Fearing chaos, the IRS has acted on its own to delay implementation of new tax reporting requirements that were scheduled to apply to third-party settlement organizations such as PayPal beginning with the 2023 tax year. The old rules for filing Form 1099-K will continue to apply for 2023, and a new transition rule will go into effect in 2024. Full implementation of the new requirements won’t occur until 2025.

Your year-end tax planning doesn’t have to be hard. This article takes your daily business activities and identifies easy year-end tax-planning moves you can make today. Our six strategies will increase your tax deductions or reduce your taxable income so Uncle Sam gets less of your 2023 cash.

The Augusta rule gets its name from the Masters Golf Tournament where some members and others who live in the area receive tax-free rent by renting their homes for a week or two. You don’t have to live in Augusta to benefit from this rule, as this article shows.

Don’t let tax deadlines catch you off guard! Stay organized and save more with our 2023 Federal Tax Calendar for small businesses and self-employed taxpayers. Download your calendar now!

Do you have a tax-deductible office in your home? Do you have a cleaning lady who cleans not only your home but also your office? If so, is the cleaning lady an independent contractor or a W-2 employee?

Billions of dollars are raised each year through crowdfunding websites such as GoFundMe and Kickstarter. Whether this money is taxable income to the recipient depends on whether it is a gift, a payment made in return for a reward, a loan, or a payment made in return for equity ownership in a business.

If you purchase an electric car or a plug-in hybrid electric vehicle to use in your business, you can qualify for a brand-new commercial clean vehicle tax credit worth up to a whopping $40,000. But that’s not all.

The IRS examiner can make a mistake. But the question is: Will you know it’s a mistake? In the situation described in this article, the tax code contains the answer. The taxpayer simply had to be familiar with it.

If you have self-employment income, you pay self-employment taxes (Social Security and Medicare taxes) on your net self-employment earnings. Not all income is self-employment income and some surprising types of income are considered self-employment income, as explained in this article.

There’s much to see in this short question and answer, such as the single-member LLC, sole proprietorship, corporation, payroll taxes, self-employment taxes, and tax-free income.

The IRS rewards business owners who are proactive in fixing their worker classification mistakes using the Voluntary Classification Settlement Program (VCSP). With this program, you can correctly classify your workers at a minimal cost and without the risk of an employment tax audit.

The IRS Classification Settlement Program (CSP) offers a chance to settle your employment tax debt due to worker misclassification if you do not qualify for Section 530 relief. CSP agreements typically result in a substantial reduction of assessed employment taxes, especially if you misclassified workers over several years.

The Section 530 safe-harbor provisions allow employers to avoid penalties, if certain tests are met, on workers improperly classified as independent contractors. The employer must have filed all appropriate federal tax returns, treated similar employees consistently, and had a reasonable basis for classifying the individuals as independent contractors.

Stay with family and friends when traveling for business. And then create tax deductions by paying them for your business lodging. You have a choice: deduct the cost of staying at the big hotel downtown, or deduct the cost of staying with your friends or family. Either way, the choice of location does not change the fact that you are on a tax-deductible business trip. The side benefit is that doing this right creates tax-free income for your friends and relatives.

In this article, you will learn when a partner can deduct unreimbursed partner expenses (UPE) and when the partnership can treat certain activity as if the partner were a 1099 independent contractor.

Here’s a sad story of a dentist who did not file his tax returns. Of course, as you know, the failure to file tax returns often gets the IRS’s attention. In this case, it did, and this dentist suffered accordingly.

The expression “I’m from the government, and I’m here to help you” is often counted as one of the three great lies. Toss that thinking out the window when you consider the PPP loan forgiveness rules that apply to the self-employed with no employees. For sure, this process is a government help to Schedule C taxpayers who took the time to obtain their PPP cash infusions.

When you are self-employed with no employees, the PPP program is a COVID-19 gift. If you now have your PPP funds, you need to review this article for insights on how to handle the money. After all, the idea is to have the loan forgiven.

Don’t overlook the COVID-19 Payroll Protection Program (PPP) if you are self-employed with no employees. For this program, you (as a self-employed taxpayer) count as an employee, and with only yourself, you qualify for the COVID-19 cash.

The federal government has given you many ways to find relief from the effect of COVID-19 on your business. You have to like the rescue. But it does require you to make choices as to which assistance to accept, because the selection of one type may preclude benefiting from a second type.

If you are in business for yourself—say, as a corporation or self-employed—payroll taxes and self-employment taxes are likely two of your biggest tax burdens. Here’s some possible good news: Congress decided to give you significant relief from these taxes due to the COVID-19 pandemic. We’ll tell you what relief options are available and whether or not you qualify.

Many workers across the U.S. are going to suffer improper reclassifications because of the California Supreme Court’s decision in Dynamex and the resulting new California law. As you will see in this article, the Tax Cuts and Jobs Act (TCJA) compounds the tax problems for the workers who are reclassified.

You didn’t issue Form 1099s to your contractors. Now, the IRS is auditing your tax return, and the auditor claims you lose your deductions because you didn’t issue the Form 1099s. Is this correct?

An auto dealer sent its customer a bogus 1099 because the customer refused to return to the dealership and redo the “no interest” loan to an interest-bearing loan. The dealer made a mistake originally and then wanted the customer to help fix the problem—at the customer’s expense. The customer said no. Later, when the bogus 1099 showing interest income from the no-interest loan showed up in this customer’s mailbox, the customer took this dealership problem to the IRS.

Get ready. You may be about to experience another encounter with the law of unintended consequences. The Tax Cuts and Jobs Act gives you a possible 20 percent tax deduction on your rental property income. But that’s only if your rental property is a trade or business, and that comes with its own burdens.

The life insurance sales professional who receives a W-2 with the statutory employee box checked is in a special tax category for income and employment tax purposes and also sits in a favored category under the new Section 199A deduction rules. But he or she may not be favored for 1099 income.

Lawmakers make business owners report to the IRS certain payments made to workers such as payments of $600 or more to independent contractors. The rules and deadlines for reporting independent contractor payments on Form 1099-MISC can be tricky. But when you know the rules, you can employ strategies that minimize the impact of these reporting requirements on your business.

Few things can rock your world like the prospect of losing your home. In a foreclosure, the lender sends you one or two Form 1099s that will worry you too. The 1099s could show that you have cancellation of debt income (that’s taxable income). And then, just to pile on, the foreclosure that took away your home might trigger a taxable gain. That’s all bad news. But when you know the rules, you’ll see that you can make some or all of the bad-news tax problems go away.

You likely want to hire independent contractors whenever possible. But if you are bending and breaking the rules, you face big back taxes, horrific penalties, and interest. So, a question for you: Have you been misclassifying your workers? If so, the IRS has a good deal that lets you off the hook with just a tiny payment. We’re talking a fraction of what you would otherwise owe if you lost your contractor classification in an IRS employment tax audit.

If you hire workers and want to classify some of them as independent contractors, you absolutely need to know about Section 530 and its safe harbor. By law, Section 530 is the first step in an employment tax audit. And if you don’t know about Section 530, you are making a potentially fatal financial mistake.

You save employment taxes when you hire workers as independent contractors. But you want to make certain that the workers are indeed contractors, or you could subject yourself to some expensive tax penalties. In this article, we show you three steps to independent contractor status for your workers.

That ugly alternative minimum tax (AMT) can raise its snakelike attack when you least expect it. In this court case, by changing the medical practice from a solely owned corporation to practicing as an employee of an education institution, the surgeon looked squarely in the eyes of the AMT and lost almost $20,000.

If you have workers who are paid on a 1099 as independent contractors, you need to avoid one fatal mistake. When you make this fatal mistake, you subject your worker employment classification to either the tax court’s common-law seven-factor test or the IRS’s 20-factor common-law test. Both of these tests are hard on the employer and often result in harsh reclassification of the 1099 independent contractors to W-2 employee status.

Rental property managers report gross rental income to the property owners on a 1099-MISC. We have seen confusion about this reporting because new laws were enacted in 2010 and then repealed in 2011. This article eliminates that confusion and explains what the property manager needs to report and what the property owner can expect to receive.

If you want to operate your business as an S corporation, you need to recognize that the S corporation is a separate legal entity and that you are an employee agent of that corporation. You also need to ensure that the S corporation is the earner of the income. You may not assign your income to your corporation.

Stay with your mom and dad on a business trip, and create tax deductions by paying them for business lodging. You have a choice: deduct the cost of staying at the big hotel downtown or deduct the cost of staying with your parents. Either way, the choice of location does not change the fact that you are on a tax-deductible business trip.

Learn what is 1099 income and why that often causes an incorrect 1099, which in turn can lead to an IRS audit. Often, correcting an incorrect 1099 on Schedule C compounds the problem. In this article, you learn how to 1099 correctly and what is 1099 income. The definition of “what is 1099 income” may surprise you.

The courts have determined that the alternative minimum tax (AMT) cheats many commissioned W-2 employees out of their rightful deductions. To fix this problem, the courts have allowed certain commissioned W-2 employees to move their employee business expenses from the IRS Form 2106 itemized deduction category to the tax-advantaged sole proprietorship on Schedule C.

You are not self-employed for tax purposes just because your employer says so. This is true even when your employer is the British consulate general.

New law retroactively repeals, as if never enacted, the 2010 law that required three new types of 1099 reporting: (1) 1099 reporting by owners of rental real estate, (2) 1099s for payments to corporations, and (3) 1099s for purchases of property.

Learn why it is important to get the independent contractor classification correct. If your supposed contractor status is in reality employee status, you suffer major penalties.

When the bank forecloses on a home, tax law comes into play in some surprising and often beneficial ways, especially this year. Tax law treats recourse and nonrecourse mortgages in completely different ways, but with a personal residence, the end result can be pretty much the same.

If you are personally liable for a debt and that debt is canceled or forgiven, you include the canceled debt as taxable income on your income tax return. Your situation dictates whether you will pay taxes on this taxable income. You might qualify to exclude the canceled-debt income from taxation altogether or to pay little or no taxes on it this year and then pay taxes in later years.

If you are thinking of hiring your workers as 1099 independent contractors, this article is for you. The article shows you how the rules work and helps you understand what you need to properly classify your workers as independent contractors.

Treasury Secretary Timothy Geithner told the Senate Finance Committee that more 1099 reporting and IRS audits provide the solution to the tax gap.

The IRS ruled that this real estate broker who gives commission rebates and commission reductions at closing does not have to give Form 1099s to his customers who receive the rebates and reductions.

Uriah Jones’ employer was late and didn’t send him his 1099 in time; he didn’t send it to the IRS, even late. Not surprisingly, he was audited. He then took that matter to court and lost. Always report your income, even when you don’t receive the 1099. It’s taxable, regardless of 1099 receipt.

Steven Olmos thought he could slip past the IRS when he changed states. It is not very complicated: the IRS knows if you do not file taxes.

Do not use your Social Security number to collect income on behalf of any other person. This will create nothing but trouble for you.

Not reporting the 1099 information is always a mistake. If you have a rental property that you rented less than 15 days this year, it is not taxable. If you do get a 1099, you should include it in your tax return, but follow our strategy to avoid any problems.

When you receive a 1099 or a W-2, you should file a tax return even if no return is required.

The solo 401(k) is one great retirement vehicle for the independent contractor.

When you win a top producer award trip to a fancy resort or location, create educational events for yourself to qualify your trip for business travel deductions. When you get this right, you offset the 1099 award value with bona fide business travel expenses.

Assigning your personal commissions to your corporation does not work. In this court case, this insurance agent had unfiled tax returns and unpaid taxes for the years he assigned his 1099 income to his corporation.

Hobby gambling can trigger taxes when you have a zero income because the law makes your winnings reportable above-the-line and losses deductible below-the-line.

When you win more than $1,200 at the slots, the casino must report your winnings to the IRS. In this court case, the taxpayers mistakenly reported gambling income of $21,100 and the IRS received 1099s showing income of $44,464. This difference in reported income did not look good in court. But these taxpayers fared far better in court than anyone in their right mind could expect because they had proof that this court liked.