It’s not unusual for small-business owners to fall behind in their tax return filings. Often taxpayers fail to file in one year and then multiply that one year into several years of unfiled returns. In this article, we give you a road map for getting your individual, corporate, and payroll taxes IRS-compliant with as little tax as possible and the fewest penalties possible.
Traditionally, tax rules put up major hurdles for small businesses seeking deductions for items such as furniture, computers, smartphones, and tablets. Now the IRS has made an important change that allows all businesses that have the right expense policy in place to elect expensing of these assets. This is a new and important change for 2016 and beyond, but you need to act fast to get this in place.
This article takes your daily activity and identifies five easy year-end tax-planning strategies. Here are two examples from the article: prepaying your expenses under the IRS safe harbor and simply not billing customers and patients until 2016. These two strategies are certainly easy, as are the other three strategies in this article.
As a small business owner, you have good odds of someday facing a penalty for late filing and/or late payment of your or your corporation’s taxes. It’s likely you will think that you have to pay the penalties. But as you’ll learn here, when you know the rules of the road, you can travel the IRS mercy path and have those penalties forgiven.
You can make your tax life easier with a business credit card—but only if you use that business credit card correctly for tax purposes. For example, charging an expense to a credit card does not make it tax deductible. You need more proof. And you could create a type of double jeopardy if you operate your business as a corporation.
If your tax debts have spiraled out of control, don’t give up hope. You may be able to use one of four IRS-created relief procedures to reduce or eliminate your debt. And if these methods still aren’t enough, find out whether bankruptcy can eliminate your remaining income tax liabilities.
This article gives you easy year-end tax planning strategies for your everyday business. For example, prepaying your expenses under the IRS safe harbor and simply not billing customers and patients until 2015. These two strategies are certainly easy, as are the other three strategies in this article.
In this precedent-setting case, the Tax Court had to decide for the first time whether a tax preparer’s fraud extends the statute of limitations for IRS audit of the client return when there is no charge of fraud against the client. If the court rules against the client, then by precedent a tax preparer’s fraud extends the client’s allowable audit period from three years to forever.
The thought of an IRS audit is a worry, no question. But it’s worse when the IRS wants a lot of your money. And it’s even worse yet when the IRS wants your money because it interprets the law incorrectly and at the time you see the IRS adjustment, you have no idea whether the IRS is right or wrong.
You need basic books and records to avoid trouble with the IRS. If you have inadequate books and records and also make a large cash deposit in the bank, you might visit with the IRS every two weeks for about a year as the taxpayers in this case did. That’s a lot of unpleasant face time with an IRS agent.
Would you like to deduct business meals with your spouse? What would the IRS think about that? If the IRS said that the meals were not deductible, what would the courts say? You would think there are hundreds of rulings and court cases that explain this. Not so. There is one tax rule that mostly assures the deduction, but it requires an addition. Spend a few minutes learning how tax law treats your spouse when it comes to business meals.
Lost records are not a death warrant when it comes to audits. But if your tax advisor tells you that you can replace your missing records with an affidavit, you need to change tax advisors. This type of affidavit is a bad idea. It will not help you. Find out what you should do instead.
Do you know for what period of time you have to keep your tax records? You may have heard three years, four years, six years, and seven years. All of these can be correct, but also 17 years can be correct with a depreciable building that you sold in year 14. Because you need to keep the records for the required periods, you need to know what those required periods are.
If you are suffering or about to suffer an IRS audit, you should know how your tax positions stack up against the IRS examiners’ positions. In most cases, you are discussing the facts, not the law, and you prove your facts with receipts, canceled checks, and logbooks. Once you get into the law, you need to know the rules that trump other rules. This article explains how you use the laws, rulings, and other IRS documents to prove the legal side of your case in an audit. And should your case advance beyond the IRS audit to the courts, this article helps you understand what the courts are looking for.
Tax law grants relief, if you want to call it that, when you lose your tax records through no fault of your own. For example, say a flood, theft, hurricane, or earthquake caused the loss of your tax records. Your relief is the right to substantiate your deductions using a reasonable reconstruction of those records. Yikes, how long will that take?
Learn how today’s restaurant and other receipts printed on thermal paper can create big trouble for your tax deductions. Over time, the images on thermal paper can totally disappear. And of those that have not yet totally disappeared, you have many that you can’t read. This means you need to create a plan that includes scanning or photocopying thermal receipts.
What happens if the IRS makes a mistake in its publication or instructions? Is this your problem, or what? And how would you know if the IRS made a mistake? This article explains how the IRS made a mistake in its publication and in its instructions on the gross-income limit that applies when you want to claim the home-office deduction and have more than one place of business.
Would you like to find more tax deductions for your business? This taxpayer created an ESOP as one way to gain more tax benefits from his business. He also created a management services corporation to provide services for his existing corporation. But he made one common and most tragic error. He just did not do the work.
Don’t claim that home-office tax deduction! It’s a red flag. Whoa! What’s a red flag and who says so? This article debunks the red flag for the home-office deduction.
Lawmakers reduced your deduction for legitimate business entertainment meals from 100 to 80 percent in 1986 and then from 80 to 50 percent in 1993. That might be good news. It could protect you from the dreaded Sutter rule, where you could lose all your entertainment meal deductions if you didn’t spend more, or differently, than you spend on yourself. Yes, tax laws can be strange.
The Federal Housing Authority (FHA) guarantees loans so that lenders can make mortgage loans with lower down payments, lower closing costs, and easier credit qualifications. When the mortgage crisis hit, the FHA changed the rules for mortgage companies that had independent contractors brokering FHA mortgages. The change allowed only W-2 employees to sell FHA loans, and thus many mortgage companies converted their brokers from independent contractors to W-2 employees. For many, this new W-2 status produces a totally unfair tax result that can be overcome with knowledge.
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.
Tax law limits the home mortgage interest deduction to a maximum mortgage balance of $1.1 million. But what happens when you have an office in your home for which you claim tax deductions and also have a mortgage in excess of $1.1 million? In this article, the IRS agent incorrectly disallowed some home-office mortgage interest, and the tax professional had difficulty finding the tax law that would overcome the disallowance.
One of our subscribers encountered a tax preparation firm that charges a commission for amending past returns. Our subscriber asked this question: “Is such a commission legal?”
How does the tax law treat the classic car when you use it for business? Can you deduct it just as you would any car you use in business? Learn how some tax law changes enabled the classic car as a business asset and why that can work to your advantage.
Your mileage log may not be an estimate of mileage. Further, you need a mileage log that proves mileage. With a weak, suspicious, or error-filled mileage log, by law, neither the IRS nor the courts may give you any vehicle deductions—and we mean none, not a penny.
Doing your taxes yourself using tax preparation software is dangerous business. You might realize the danger up front and decide that you need some type of audit defense or representation insurance in case of an IRS audit. And then, once the audit commences and you engage your audit defense team, find yourself in the soup like the couple in this article.
Protect yourself and your receipts by digitizing them. You will like the results. Digitized receipts make the IRS smile and, of course, that makes you smile too. Without digitization, some of your receipts will disappear.
Is your worker an independent contractor or an employee? You want to get this right at the beginning. But if you improperly classified an employee as an independent contractor, the IRS has a tax penalty relief program for you. Should the IRS plan not have the best relief for you, consider the Section 530 employer protection plan.
The appeals court remanded the Shellito case back to the Tax Court along with its road map for establishing the Section 105 plan. In the right circumstances, the 105 medical plan creates tax deductions where none existed before, and its tax-free fringe benefits can operate as the sole remuneration to the employee-spouse.
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.
You learn valuable business and documentation strategies from IRS audit manuals. We spend time reading these. In this article, we reviewed the IRS audit manual on self-employed lawyers and carved out selected business and documentation strategies you can use to audit-proof your deductible business entertainment.
How do you lose deductions to the IRS in an audit? Worse, how do you compound that loss of deductions by taking your case to court? In this article, see how one proprietor managed to do both.
Renting to your corporation can produce tax advantages. Even failing to collect the corporate rent, as the individual did in this court case, can produce tax advantages.
The cabin at the ski hill could be a hotel, a residential rental property, or a personal residence. It depends on your personal use of the property; the length of rental periods; and documentation of your time, others’ time, expenses, and activities.
The IRS is in the midst of its largest hiring initiative in years. Therefore, the increase in IRS audits seen during the last few years is expected to continue at an even greater rate.
Special documentation rules apply to entertainment and vehicles. One rule requires you to document your entertainment and vehicle use within one week of the activity. Another rule says you don’t need receipts if the expenditure is less than $75—but you still carry the burden of proof.
The CPA in this court case operated as an S corporation with a low salary. The low salary got the IRS’s attention. To salvage bigger things, the CPA had to take the IRS to court
When the IRS invites you for a tax audit, the examiner does not know that you hired your children. This fact surfaces during the initial interview or survey process, and the IRS instructs its examiners to examine this hire closely. You avoid all the problems when you have the right records.
When you fail to seek reimbursement for an expense, you often have no write-off. However, there are exceptions to this general rule, as examined in this tax audit tip
The tax strategy of renting property you own personally to your businesses needs your attention if you want tax benefits. Similarly, special recharacterization rules apply to rentals of land and also when land is a big part of the rental.
Should you or your corporation be unlucky enough to face an IRS audit, there is one record that stands out as critical to your audit health. If you are missing this one record, the IRS audit can quickly expand to other areas of your tax return.
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.
Do you own a business that withholds taxes from employees? If so, you need 100 percent certainty that the withheld payroll tax monies are going to the IRS. You can achieve 100 percent certainty with the IRS EFTPS registration..
You can keep records that reduce the chances of an IRS physical inspection of your office in the home.
To deduct a loss on a charter fishing activity, you must materially participate in the activity. When the activity is organized as an LLC, you have more choices for material participation than a limited partner.
If you understate your gross income by more than 25 percent, the IRS can adjust that return for six years, rather than the traditional three-year statutory period for audits. In this clarifying regulation, the IRS explains that an overstatement of basis counts as an understatement of gross income for the 25 percent test.
You need a mileage log on your business vehicle. With no mileage log, you can try the alternate-proof method, but the odds are better than 9 to 1 that you will lose. This article gives you a perfect mileage-log system free.
Credit cards are valuable time-saving assets when used correctly by the business taxpayer. Incorrect use damages both your wallet and your time management.
Swiss UBS AG and other supposed tax havens and secret banks are divulging the names of tax cheats to the U.S. government.
The woman in this audit learned how knowledge can turn what appears as a nightmare (an IRS audit) into a positive happening—meaning cash refunds for the year of the audit and subsequent years. As the old sayings goes, “knowledge is power.”
This article empathically answers the “show me where it says that you can use three cars for business” question.
The court made it clear that every taxpayer may properly use the tax law to reduce his or her tax burden, but the use of paper entities that fail the economic reality test does not work.
If you are looking for tax deduction trouble from the IRS, do this: Don’t file your tax return or at the very least, file it well after the filing deadline.
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 has a procedure in place where you can ask “not to be audited” this year for the same items for which you were audited last year.
Ownership and involvement in your business may not be sufficient if your business suffers an operating loss. To deduct a business loss, you must materially participate in the business.
A real estate rental is automatically in the passive bucket if you do not qualify as a real estate professional. In this court case, a real estate agent qualified her real estate agent work time as time spent in a real property trade or business. Thus, she qualified to deduct her real estate rental property losses.
Two tax attorneys told our group that time spent as a real estate agent actually worked against you for the time test (more than 50 percent) to qualify as a real estate professional. The attorneys claimed that in audits the IRS is disallowing the unlimited loss to people who are full-time agents, treating their agent work time as non–real estate time and thus making it just about impossible to meet the 50 percent test.
The law gives you no choice but to keep the proper tax records on a timely basis. This is pretty easy when you know what to do. One easy rule to follow is to never commingle your activities in your bank accounts. Both the rule that requires a mileage log and the rule that requires a time log are more difficult, but absolutely essential to proving your deductions.
Over 1.6 million businesses collectively owe the IRS more than $58 billion. Who to blame: cheating government contractors, a lenient IRS, irresponsible lawmakers, dishonest businesses. What to do, and how to protect yourself against a dishonest payroll service.
When using tax preparation software, be alert to automatic calculations that could place improper amounts on your tax returns.
Be careful when appealing an IRS case to a higher level. Usually cases are for the technical merits of your issue or facts; seldom does it result in an expansion of the examination.
One taxpayer is in big trouble: he owes $61,000 in overdue taxes. Why? Bad records. We give him recommendations on what to do, but he is not in good shape.
In an ISP, the IRS asserted that the Section 105 medical reimbursement plan may not reimburse the employee-spouse for the cost of health insurance purchased in the employee-owner’s name. This court case held that this IRS position is wrong and that the owner may deduct the cost of medical insurance purchased in his name when that insurance is covered by the Section 105 medical reimbursement plan.
Answering “yes” to the 11 puts you on the road to audit-proof status for your Section 105 medical reimbursement plan.
When you use an intermediary to complete a Section 1031 exchange, you sell one property and place the cash on deposit with the intermediary. If the intermediary goes bankrupt causing your exchange to fail the time test, you are on the hook for the taxes.
New tax rules have pretty much killed the once-common tool and car allowances as expense reimbursement methods.
Carolyn Federson lost all of her rental property loss deductions when the court rejected some of the details of her rental property time records and made its own estimate of the time she spent on her rentals.
Anti-alienation provisions prevent ordinary creditors from levying pension payments. The IRS does not suffer these provisions.
Gambling requires good strategies not only in your gambling activity, but also for tax purposes. You need to report your gambling income and losses in your tax returns and keep tax records whether you win or lose, whether the gambling is legal or illegal, and whether the gambling is a tax defined business or hobby.
Terry Gerber was sentenced to two years and six months in federal prison for tax evasion.
The taxpayer in this case relied on his lawyer, but that lawyer did not know the home-office rules. Then, the judge misapplied outdated rules to his home-office deduction, costing this taxpayer $7,000.
Technically, cash basis taxpayers deduct checks when they are delivered and negotiable. For the most part, the courts and the IRS employ practical applications to make this rule easy for you.
Robert Walters’ auto deductions sank from $10,878 to $966 because of poor record keeping. Do the best thing you can do for yourself. Keep a good mileage log next to your appointments. This can be easy, and it will save your bacon if you get audited.
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.
One taxpayer is audited, and told incorrect information by an IRS agent. We give her proof to support her position.
The ability to deduct rental property losses can alter investment returns by as much as 40%. In many cases, the ability to deduct the losses can make the sole difference in making a profit or incurring a loss on the rental.
If you own a condominium, cottage, cabin, lake or beach home, ski lodge, or similar property, tax law might consider your property a hotel. The purpose of this article is to alert you to the tax issues that surround a vacation-home hotel.
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.
Tracy Topping saved $251,462 in taxes when she proved that her horse activity was not a hobby, but a promotional tool for her business.
From a legal standpoint, income taxes are levied on an annual basis, so that each year represents a new liability and a separate cause of action. Under this principle, taxpayers do not establish entitlement to deductions in one year merely on the basis of allowance of similar deductions in a previous year.
The IRS has very specific rules regarding record-keeping for deductions. One husband-and-wife team lost over $31,000 because of bad records. Know the law!
The IRS is not a forgiving entity. Even if a fraudulent payroll service is charged criminally, as in this case, you are still responsible for the taxes you owe. We give you a sound strategy to avoid payroll fraud.
Vincent Allen hired a tax preparer to file his tax returns. The preparer was charged with fraud. Although the IRS did not bring the fraud charge against Allen, users of fraudulent preparers could easily be charged and convicted of fraud themselves.
4% of Americans are audited each year. Do you know what two line-item expenses are most vulnerable to a Schedule C audit? Take our quiz and find out!
Anthony Lee was sentenced to seven months in prison and three months of home detention for failure to file his tax returns. He owed $76,853 in taxes and an extra fine of $10,000. Know the law!
The IRS puts out its audit manual every year. It not only contains information on how to audit, but also gives information on disallowing deductions. We dissected the audit manual and give you 11 audit-proofing tactics to ensure you get the deductions you deserve.
You have probably read that the home office increases your chances of IRS audit. We’ve read that, too, but we don’t believe it. Regardless, there are a few things you can do to make your home-office audit-proof.
In March 2007, the IRS released its latest audit statistics. Your odds of avoiding an audit are getting worse.
Dr. Rinker lost over $60,000 of deductions when her tax preparer lost her records. Don’t lose your tax records, and don’t give your original records to anyone, not even your tax preparer!
Even if you do not owe any money, you move right to the front of the line for an IRS audit if you do not file your taxes on time. Always file a tax return, even if you cannot pay the tax.
Learn from one taxpayer’s mistake: if you hire a lawyer for tax court, hire a tax lawyer.
IRS auditors do most of the audits. They are not accountants (IRS agents are accountants); they might be wrong about tax law. It’s your responsibility to know the law and use it to prove your point. This article tells you how to use court rulings and documents that enforce your rights in your tax-law partnership.
Answer this question: Could you prove that you filed last year’s tax return? Is your proof credible enough that it will stand the scrutiny of the IRS?
Revenue procedure 2007-16 allows you to make a change in depreciation after you sell, trade, or abandon property. The new procedures make some prior procedures obsolete and make revisions easier.
Getting the IRS to give you an advance ruling on a transaction or deduction can be very worthwhile. It now costs money, but it might be worth getting the opinion you seek. If your ruling does not fit into the three major categories they list, your fees may vary. The highest fee is $50,000 for a pre-filing agreement.
The law contains no reasonableness test for mileage. There are very specific rules for recording mileage. We recommend that you keep a mileage log for three consecutive months to prove your business-mile percentage.
You need to know the rules to protect yourself not only from the IRS, but also from the courts. If you don’t take the proper position on your home-office deduction, neither the IRS nor the courts give consideration to the arguments you should have raised that would have won your deductions.
It matters not that you used a paid tax preparer to help you, you commit tax fraud and face jail time when you take illegal tax protestor positions on your tax returns.
When you receive a 1099 or a W-2, you should file a tax return even if no return is required.
If your tax records are destroyed in a fire, the IRS allows you to reconstruct the records. Reconstruction takes a big effort. Protect your records so that you don’t have to reconstruct them.
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.
Today’s computer and Internet technology give you a variety of new safeguards that you can use to protect your tax records. When thinking about your records, keep this one overriding rule in mind: no records, no deductions.
It is highly unusual for the IRS to revoke a private letter ruling. You can protect yourself from a revocation by making a proposed transaction the subject matter for the ruling.
Tax benefits for the bed and breakfast require adherence to the transient, vacation home, and hotel rules. Under these rules, personal use can destroy deductions. Further, the length of transient stays determines the types of services you need to provide, if any, to qualify the bed and breakfast for tax-favored hotel benefits.
Bad records can cost you just about every tax deduction. You can testify as to your deductions, but without the records that turns out worthless. When it comes to your taxes, paper talks.
If you don’t have the tax records or if you are just not cooperative, you could enable the IRS to use the bank deposits method to determine your taxable income. This is a bad thing. When the IRS uses the bank deposits method to determine your tax liability, you generally pay a whole lot more tax.
Not filing your tax returns on time because you lost or misplaced your tax records is going to make your tax life miserable. The trouble is so bad that you need to consider an “offer in compromise.”
This taxpayer won his deduction for going to the library located 36 miles away from his home and next to his parent’s home. The IRS lost its argument that the taxpayer should have used the library near his home rather than drive 36 miles to the library where he also could visit with his parents.
The IRS fulfilled its promise and audited twice as many Form 1040-Schedule C taxpayers and S corporation returns. Your odds of audit vary by both choice of entity and gross receipts in that entity.
Many sporting events qualify for a 100 percent entertainment deduction rather than the traditional 50 percent. This is true for both participants and spectators. To qualify for the 100 percent entertainment deduction, the net proceeds of the event must go to charity—as they do in a PGA Tour golf tournament.
When you start a new business activity or you do a business activity on the side, you must establish a profit motive. One easy way to demonstrate the profit motive is to show the time you spend on the activity. This taxpayer had no proof of time worked, so he looked suspicious to the court.
The properly used business condo does not run up against the vacation-home, passive-loss, or entertainment-facility rules.
Making a lot of money is no excuse for keeping bad records. Top off the bad records with failing to give adequate documentation to your CPA and you add to your misery index with negligence penalties. The taxpayer in this court case had to shell out about $5 million in taxes and over $1 million in penalties.
The law requires the taxpayer to maintain records sufficient to establish his income and deductions. In select circumstances, estimates provide a rational basis for deductions. With respect to vehicle, entertainment, meals, travel, and gifts; estimates are out and neither the court nor the IRS may grant your deductions without the prescribed records.
Both the IRS and the courts have approved pencil as adequate for tax entries.
The taxpayer’s tax preparer told him to create an “Affidavit of Facts” to support his tax deductions. This was a useless exercise. This tax preparer, the one who recommended the useless affidavit, lost his enrolled agent status, and the time of this trial was forbidden by the United States government to prepare tax returns.
Interest paid on a life insurance loan to buy a home does not count as deductible mortgage interest.
The auto dealer sent this 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.
This taxpayer embezzled money from his employer, got caught, and died in jail. Before he died, the embezzler sent the embezzled money to the IRS as an estimated tax payment.
The IRS told lawmakers that a number of people were cheating on vehicle donations and that some changes in the rules could put a quick stop to that. This court case explains why lawmakers went along with the IRS and enacted the changes that are in effect today.
To make sure that the IRS will treat the C corporation’s advances to the employee-owner as tax-favored loans rather than tax-penalized dividends, make sure you can answer “yes” to the seven questions.
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.
The IRS audit manual states: “If you rent all or part of your residence to your employer and use the rented portion when performing services for the employer, you cannot deduct home-office expenses attributable to the rental.” Thus, forget the rental to the corporation and use the corporate-reimbursement-to-the-employee strategy for maximum benefits.
This taxpayer had his CPA with him during the IRS audit of his tax return. When the home-office deduction came up, the CPA agreed with the IRS that this taxpayer did not qualify for the home-office deduction under Soliman—a Supreme Court case that lawmakers made obsolete in 1999 with enactment of a new law. Thank goodness this taxpayer was a subscriber to this newsletter and, because of that subscription, knew the rules on the home office.
During an audit, the IRS can pretty much allow or disallow whatever it wants. In this first stage of the audit process, the burden of proof is on you.
Under tax law, your vehicle is considered “listed property.” The IRS has a regulation that applies the $75 receipt rule to listed property.