All Articles - Think Outside the Tax Box

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By Jeff Stimpson

How to Deal with Huge Tax Debt

The only thing scarier than owing Uncle Sam a lot in taxes is being unable to pay the bill. Luckily, the Internal Revenue Service has ways for you to whittle what you owe. Just make sure which method works for you, depending on such factors as the size of your tax debt and what you can afford to pay and when. Don’t panic. Here’s how individual taxpayers can proceed – and what to watch out for.

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Finally – SALT Cap Workarounds to Bypass Schedule A Limits

Ever since TCJA passed, taxpayers in high income tax states have been wincing each time they see the $10,000 limitation appearing on Schedule A. But while the law included this $10,000 state tax deduction limit for individuals , it did not include a limit for partnerships, S, or C corporations. To clarify the deduction’s limitation, the IRS issued a notice blessing an entity-level tax and accordingly, many states have implemented such a tax. This allows you the ability to bypass the $10,000 limit on Schedule A and deduct the state taxes paid as a business expense. As of this writing, 19 states have passed what are known as “pass-through entity taxes,” but there are pros and cons to using this loophole. If you are the owner of a pass-through entity and pay more than $10,000 each year in state taxes, this workaround may increase the state tax deduction beyond the limit. Keep reading to learn how.

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To the Moon: Tax Saving Strategies for Meme Stocks

Think back to January 2021. A new President was sworn in; Twitter was obsessed with “Bean Dad,” and the term “Meme Stock” entered popular culture. A previously obscure subreddit called “Wall Street Bets” began making front page headlines. Average Americans took their “Stimmies” and invested them into unpopular companies, some on the verge of failure, and started making double digit percentage gains per day by pitting their collective holdings to short squeeze institutional investors. Companies that no analyst listed as a good buy, such as a retail video game store (retail is still a thing?), a movie theater chain (in the middle of a pandemic) and multiple cell phone companies (that don’t produce Apple or Android phones) all began to skyrocket overnight. As of this writing, GameStop Corp. ($GME) was up nearly 2000 percent in the last year. It’s likely while riding the adrenaline rollercoaster, most investors were not thinking about taxes. There are no taxes on the moon, but it’s not too late to plan for tax consequences here on Earth.

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Even an Existing Business Can Claim the $100,000 of COVID Relief Money for Startups

You might be a startup without even knowing it. If you are not a startup business today, you could be shortly. The incentive to start a business and hire employees is especially high now due to the Employee Retention Credit (ERC). With a special rule specifically for startups, the government will pay 70 percent of the first $10,000 of an employee’s wages in both the third and fourth quarters of 2021. This means it’s possible a business with as few as eight employees can claim the maximum $100,000 under the Recovery Startup Business rules (RSB). Even an existing business may qualify as a startup to claim RSB ERC. There are steps a business can still take today to qualify. A new business activity, reorganization, change in ownership, related company, business purchase, or even a more detailed review of the average receipts calculations could trigger a qualification. Read on to learn more about this planning opportunity and the rules to do it well.

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Tax Court Allows Defense Contractor to Claim Afghanistan as Tax Home

Question: We have a client who is moving out of the country, can they qualify for the foreign earned income exclusion? Answer: Deborah C Wood owned a house in Texas but was able to convince Judge Lauber of the United States Tax Court to rule that her true home was Kandahar Airfield in Afghanistan. This saved her most of the $95,301 in additional tax that the IRS was seeking for the years 2012-2016, not to mention penalties and interest. The narrative that allowed her to win the case is worthy of study by those who represent expatriates who may qualify for the foreign earned income exclusion. There is another lesson in the case, though and that is to seek good tax advice sooner rather than later.

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Are Electric Vehicle Credits Really Worth It? Spoiler Alert: It Depends!

It happens all the time. A client comes in with the receipt for a new hybrid or electric vehicle and is expecting a huge tax credit to offset some of the purchase expense. It’s a fact that hybrid and electric vehicles cost more (some estimates say an average of $19K more) than their internal combustion engine (ICE) based counterparts. And, despite the fact that hybrids and fully electric vehicles continue to gain market share, it has continued to be difficult to quantify exactly how much fuel and maintenance cost savings offset the larger price tag. Often, the time span for offsetting the difference in purchase price is much longer than many taxpayers want to keep their cars. Taxpayers hope tax credits will help them to recoup the difference in purchase price more quickly than fuel and maintenance cost savings. Do they? Are electric vehicle tax credits really worth it? Well, it depends.

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COVID Relief Money Is Still Hiding in Plain Sight: The Employee Retention Credit

Business COVID relief funds have been plentiful. We have seen it all from state and local grant programs to the Restaurant Revitalization Fund and Paycheck Protection Program (PPP). The dollars have flowed freely during the past two years although some programs were certainly simpler than others. The Employee Retention Credit (ERC), unfortunately, has been the most complex and misunderstood relief program. It deserves serious consideration along with a second and third look. ERC has suffered from a branding problem, from repeated changes, and because the PPP overshadowed it. The CARES Act brought both programs to life in March 2020 , but small businesses quickly ignored the ERC in favor of the forgivable PPP loans. A taxpayer could only choose one of these programs until the December 2020 COVID relief law retroactively allowed them to coexist in the same business. But once again a second round of PPP loans overshadowed the ERC. Perhaps now with the grants awarded and PPP funds issued, the ERC can finally get the attention it deserves. The benefits are tremendous at up to $5,000 per employee in 2020 and $28,000 per employee in 2021. Opportunities abound for businesses and advisers to be on the hunt for ERC eligibility both obvious and obscure. Today, let’s review the program and cover some of the unusual ways to qualify.

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Wash Up for Tax Savings – Cryptocurrency and the Wash Loss Rule

When recognizing capital gains during a tax year, it can often make financial sense to sell assets that have lost value to offset profits in other investments or regular income. In this situation, you swap stocks, bonds, or mutual funds by buying a similar asset, selling the old asset and taking a loss. This strategy is called tax-loss harvesting, and it can be applied under certain circumstances which will lower your taxes. Yet while the tax deduction might seem appealing, you might have a hard time locking in that loss forever, and you may be inclined to repurchase the same investment in case the value rebounds. This strategy may appear brilliant on paper; however, the IRS doesn’t allow such manipulation just to reduce taxes. The Wash Loss Rule prevents traders from realizing a tax loss on a position that the taxpayer reacquires within 30 days after (or before) selling a security. But a little known loophole may allow you to complete a wash sale and claim your deduction without recognizing the loss forever as long as it is crypto. Cryptocurrency continues to be an area where the rules don’t always seem to make sense. Most experienced investors are already familiar with the “Wash Loss Rule,” while many newer investors have recently learned about it the hard way. To learn this valuable strategy for offsetting your capital gains while remaining in the investment gain for expected future growth, continue reading to learn more.

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California’s AB-5 And Its Impact On Small Businesses That Work with Independent Contractors

Question: I run a virtual business with no employees, but independent contractors perform all the work. I heard about that case in California. Should I be doing something different in my business? Do I owe any penalties for how I’ve done it in the past? Answer: Effective January 1, 2020, AB 5, later AB 2257, radically changed the rules and criteria for determining whether a worker’s classification is independent contractor or employee. The so-called “gig law” was effective based on a California Supreme Court case from 2018. The significance of the ruling is that it changed the criteria of worker classification and held that workers are presumptively employees and the burden is on the hiring entity to establish that a worker is an independent contractor not subject to wage order protections in California. Although this is a change impacting California employers, the rest of the country has eagerly watched and hoped to cash in on the changes that would generate billions in employment taxes. Businesses that prefer to work with independent contractors such as Uber and Lyft were quick to propose a ballot initiative in 2020 that the voters passed and now drivers are exempt from the new criteria (insert eyeroll here). Want to know how to get your own exemption from AB-5? Continue reading.

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