Pay Your Taxes In Bitcoin, Trigger Tax Losses On Price Drop Too

With Bitcoin and other crypto prices down again, many holders don’t want to sell. But if you owe taxes, how about paying them in Bitcoin? Selling now may trigger tax losses to use next year too. In Ohio, you can now make state tax payments in Bitcoin. It’s only for Bitcoin at present, but the permitted crypto should expand according to Ohio beat out Arizona, Georgia, Utah and New Hampshire, where efforts to accept crypto for taxes failed. The transaction fee is zero during an initial three-month introductory period, and then 1% thereafter. Even if you owe taxes to Ohio, that does not necessarily mean you qualify. So far, this is just for businesses operating in Ohio. If you operate a business in Ohio and have a tax bill, you can register at All payments are processed by third-party processor, BitPay. Payments are converted to dollars before deposit into a state account. 

Ethereum, Bitcoin and Ripple coins (physical). (Photo by Ulrich Baumgarten via Getty Images)

Payment Protocol-compatible wallets include BitPay Wallet; Copay Wallet; Wallet; Mycelium Wallet; Edge Wallet; Electrum Wallet; Bitcoin Core Wallet; Wallet; BRD Wallet; and Bitcoin Cash (BCH) Wallets. If you don’t have one, says you can create one. 

Remember, the IRS ruled that cryptocurrency is property in Notice 2014-21. That classification as property has some big tax consequences, accentuated by wild price swings.  If you owe $5,000 in taxes, you could pay the $5,000 in dollars. If you pay with $5,000 worth of Bitcoin, as long as the crypto is worth $5,000 when you pay, you’re home free, right? Not really. You need to consider the sale you just made. The transfer of the crypto to the tax man is a sale, and that could mean more taxes for the year of the payment. If you bought the crypto for $5,000 the day you pay your taxes, there’s no gain.

But suppose you bought the crypto a year ago for $1,000 and it’s worth $5,000 when you use it to pay taxes? That’s right, you have a $4,000 gain. Hopefully, it is a long-term capital gain, which would make the taxes lower. But you still have taxes to pay—because of your tax payment. You could trigger a tax loss too, if you had bought the crypto for $7,000 and transfer it for taxes when it is worth $5,000. All sorts of transfers can trigger taxes. For example, payments using virtual currency made to independent contractors are taxable transactions to both parties. The recipient has income measured by the market value at the time of receipt.

What’s more, as with other payments to independent contractors, payers engaged in a business must issue IRS Forms 1099. You can’t enter “1,000 Bitcoin” on IRS Forms 1099. You must value the payment in dollars, as of the time of payment. A payment made using virtual currency is subject to Form 1099 reporting just like any other payment made in property. The person paying the independent contractor with crypto just sold it. Whether that triggers a gain or loss depends on the payor’s tax basis. The gain might be capital or ordinary. If you hold it for more than a year, the best deal is long-term capital gain treatment.

But actually, gain or loss depends on whether the virtual currency is a capital asset in your hands. Most people can probably say they are investors in crypto, not a dealer or someone using it in their trade or business. But it is worth considering. Ordinary income vs. long term capital gain treatment can spell a big difference. You might have to pay only 15% on long term capital gain. But top long term capital gain rates are 20%, plus the possibility of the 3.8% net investment income tax under Obamacare.

Every time you transfer crypto, you might trigger gain or loss. Tax basis and holding period are important, as is record keeping. If you receive virtual currency as payment, you must you include its fair market value in income. Report the fair market value in U.S. dollars on the date you receive it. If you “mine” virtual currency, you have income from mining, and the fair market value of what you produced is income.

via Robert W. Wood


13.3% California Taxes Triggers Moves & Trusts To Avoid Taxes

California income taxes are high, up to 13.3%. Plenty of people try to avoid California taxes by moving shortly before a major income event. That is not a new idea, although there is more of it now than ever before. One added reason is the federal tax law’s $10,000 cap on deducting state taxes. You might not feel the pain of that rule until you prepare your 2018 tax return, but that time is coming soon. Besides, many high tax state residents start thinking of moving right before a big income event. They might be selling a company, settling a lawsuit, or sitting on a mountain of Bitcoin. Done carefully, and with the right kind of income, a tax-motivated move can cut the sting of California’s high 13.3% state tax.

Yet even moving to avoid California taxes can be tough. If you are dealing with the state’s notoriously aggressive Franchise Tax Board you can still have problems. A related and newer approach that is still largely untested involves setting up a new type of trust in Nevada or Delaware. A ‘NING’ is a Nevada Incomplete Gift Non-Grantor Trust. A ‘DING’ is its Delaware sibling. There is even a ‘WING,’ from Wyoming. Let’s say you can’t move quite yet, so you wonder if a trust in another state might work? The usual grantor trust you form for estate planning doesn’t help, since the grantor must include the income on his return.

Credit: Shutterstock

Some sellers hold significant assets and move states before they sell. California may have a claim on some of the sales proceeds even if the move is well-timed, bona fide, and permanent. Indeed, California can also dispute the move, arguing that a move in March really was not a move until July. With a Nevada or Delaware Incomplete Gift Non-Grantor Trusts, the donor makes an incomplete gift to the trust, and the trust has an independent trustee. The idea is to keep the grantor involved but not technically as the owner. New York State changed its law to make the grantor taxable no matter what, but California has not yet done so. Thus, some marketers of NING and DING trusts offer it as an alternative or adjunct to the physical move. The idea is for the income and gain in the NING or DING trust not to be taxed until distributed. At that point, the distributees will hopefully no longer be in California. The chosen trustee must not be a resident of California.

Tax-deferred compounding can yield impressive results, even if it is only state income tax that is being sidestepped. If the NING or DING trust is being used to fund benefits for children and will grow for years, it may make even more sense. Parents frequently fund irrevocable trusts for children, and may not want the trust to make distributions for years. The parents might also remove future appreciation of trust assets from their estates. For tax purposes, most trusts are considered taxable where the trustee is situated.  For NING and DING trusts, one common answer is an institutional trust company.

For trust investment and distribution committees, the committee members should also not be residents of California. Even if you jump through all the requisite hoops, the NING or DING trust may still pay some California tax. For example, if the trust has any California source income, it will still be taxable by California. Interest, dividends and gains from stock sales are intangibles, typically not California sourced. But gain from California rental properties or the sale of California real estate is sourced to California no matter what.

Outside of New York residents, the jury is out on NING and DING trusts. The facts, documents, and details matter. California tax lawyers know that the state rarely takes aggressive tax moves lying down. Still, California seems more likely to attack these trusts in audits rather than through legislation. Even so, state tax fights in California can be protracted and expensive. But if one is careful, willing to bear some risk, and there is sufficient money at stake, the calculated risks can make sense.

via Robert W. Wood

Give Employees Guns For Christmas? Get Tax Bill

Especially in these highly charged times, guns are not the most universal of gifts. But one company this holiday season has given guns to its staff, prompting some mixed reactions. The owners of a novelty glassware company gave employees pistols and rifles, a “unique and memorable” Christmas present. A Wisconsin boss gave his entire staff guns for Christmas. Bruce and Ben Wolfgram are father-and-son owners of Benshot, a Wisconsin-based company selling drinking glasses embedded with bullets. Sixteen employees got the gifts. “Our main motivator was personal safety and protection, but we live in a local hunting community so we already know how people feel about weapons,” Ben, 35, told Yahoo Lifestyle. “We also know our employees and their families well, so there’s lots of trust here.”

photocredit: Getty

The mechanics involved a collective $8,000 in gift cards to gun stores. Employees had to undergo a gun-safety course at work. Given the $500 per employee, the taxes are worth considering. Aren’t gifts tax-free? Not always, and distinguishing between income and gifts can be tough. If gifts are made out of “detached and disinterested” generosity, they aren’t taxable. But gifts to employees beyond small amounts are usually viewed as compensation by the IRS. Any individual can give gifts to another and avoid gift tax as long as the gifts are no more than $15,000 a year. And if they’re really gifts, there is no income tax either. Still, get used to thinking that taxes apply everywhere. If you win the lottery or hit it big at the casino, you pay tax. If you win goods instead of cash, their value is income. When Pontiac gave away cars on Oprah, the recipients were on the hook for taxes even though they didn’t receive cash.

For employees, the IRS considers certain gifts or benefits too small to tax, so called de minimis benefits, including such things as:

  • Controlled, occasional employee use of photocopier
  • Occasional snacks, coffee, doughnuts, etc.
  • Occasional tickets for entertainment events
  • Holiday gifts
  • Occasional meal money or transportation expense for working overtime
  • Group-term life insurance for employee spouse or dependent with face value not more than $2,000
  • Flowers, fruit, books, etc., provided under special circumstances
  • Personal use of  a cell phone provided by an employer primarily for business purposes

But not all holiday gifts are tax free. Whether an item or service is de minimis depends on all the facts and circumstances. Notably, if a benefit is too large to be considered de minimis, the entire value of the benefit is taxable to the employee, not just the excess over a designated de minimis amount. If your employer gives you a turkey, ham, or other item of nominal value at Christmas or other holidays, don’t include the value of the gift in your income. However, if your employer gives you cash, a gift certificate, or a similar item that you can easily exchange for cash, you must include the value of that gift as extra salary or wages regardless of the amount involved.

If something is taxable, the employer must withhold extra taxes from the employee’s cash pay to make up for any property given in kind. Can’t you claim it was a gift? A briefcase or a country club membership from your boss is not made from “detached and disinterested generosity.” Instead, it is meant to reward you for a job well done, and to help secure your services in the future. It is worth checking out the IRS rules for what constitutes a de minimis fringe benefit.

If employee works unpaid overtime and you reward him with tickets to the Super Bowl, they are wages. You’re supposed to increase the withholding on his cash wages to cover the value of the tickets. But that works only if you pay with a combination of cash and goods. If a buddy who isn’t a regular employee helps out at your business occasionally and you thank him with tickets? The IRS says to report them as pay on Form 1099. The IRS likes those forms, and increasingly relies on information matching. And that’s one reason why mistakes with Form 1099 can cost big.

via Robert W. Wood

Need A Tax Opinion? Here’s Why You Might Want One For IRS

I write tax opinions, so I am biased about their value. Yet it surprises me how many people pay for tax opinions without thinking about what they are getting. Conversely, many don’t get a tax opinion despite the need. If you wait until you are audited, it is too late. What exactly is a tax opinion? Distinguish between tax opinions about your own situation from tax opinions attached to investment programs. The best type of tax opinion is customized. It is formal written advice about your own tax circumstance, whatever they are.

You might have settled some litigation and received money, or paid big legal fees. You might have moved states, liquidated a business, sold or exchanged a stockpile of Bitcoin, or had an involuntary conversion or casualty loss. You might have received a legal settlement you hope is tax free because of physical injuries or sickness. You might be claiming that your stock sale proceeds are tax exempt as qualified small business stock. Whatever your situation, you want formal tax advice about the strengths and weaknesses of your position before you file your return and spend your money.

IRS Audit report and calculator on a desk.

Tax opinions are usually thorough, discussing your facts and numbers, and the legal authorities. But when it comes to the bottom line conclusion, tax opinions generally conform to one of the following choices:

  • Not frivolous = There’s a 10% to 20% chance your argument will prevail.
  • Reasonable Basis = There’s a roughly one in three chance you’ll win.
  • Substantial Authority = There are cases both ways, but there’s probably about a 40% chance you’ll win.
  • More Likely Than Not = The odds are better than 50% that you’ll win.
  • Should = It’s about 60% likely that you’ll win.
  • Will = Your tax treatment is nearly assured.

Under IRS standards, the tax practitioner must assume there will be an audit. That way, the opinion’s conclusion is not based on audit lottery. In reality, of course, audits are rare. One common question is the extent to which an opinion will get you out of penalties if the IRS disagrees with your treatment. In general, the higher the standard of opinion, the more it can help with penalties. However, even a lower level opinion helps. Even an opinion that you have a reasonable basis for your tax position can be enough to protect you if you disclose your position on your return.

Of course, just penalty protection isn’t enough. You don’t want to end up paying all of the tax and all of the interest, even if there are no penalties. What you really want is to have your tax position upheld. An opinion can help. In fact, an opinion can help put you in the best possible light on both the facts and the law. Although customized tax opinions are arguably the best kind, there is another type of tax opinion. Some tax opinions are marketed in connection with investment offerings. 

Example: Your broker pitches you to buy an interest in an LLC owning railroad cars that will carry special food products. You get a prospectus showing you’ll get depreciation and tax credit benefits worth five times your investment in the first 12 months. You can’t sell for three years, but who needs sales proceeds when you’re getting tax benefits like that! A tax opinion included with the prospectus says it is “more likely than not” you’ll get your tax benefits. You may have had no contact with the law or accounting firm rendering the opinion.

You probably don’t think of them as looking out for your interests, as they are representing the promoter or sponsor of the investment program. Still, it’s clear you’re supposed to be impressed by the opinion. You may get your own tax adviser to formally or informally opine on it too. Be careful with tax opinions of this sort. Sometimes, these investments go bad. The IRS may deny the tax benefits, and there may be litigation. One type of litigation is with the IRS. Another is between investors and promoters if the investment goes under or tax benefits are denied.

To return to the customized type of tax opinion, try to plan ahead and get some tax advice before you sign documents or make major decisions that will impact your taxes. Often, that kind of tax advice can precede a formal tax opinion naturally. That way, the tax adviser is part of the process and can help shape the tax opinion and make it stronger. And once the tax opinion is written and your tax returns are filed, you have a ready source of authority if the IRS comes knocking. If they do, don’t hand the opinion to the IRS. Instead, use it as a ready source to cut and paste into targeted responses to the IRS. Having all that work done in advance can make a world of difference.

via The Tax Lawyer

Wesley Snipes Loses $23.5 Million Tax Case, Offers IRS Tiny 4% Compromise

You have to hand it to Wesley Snipes for persistence. His various run-ins with the IRS haven’t gone so well over the years, and he now has another tax case loss to count. His latest loss was in U.S. Tax Court, which sided with the IRS. It was part of his running feud over old IRS bills that are still valid but that Snipes says he cannot pay. He offered a fraction, about $842,000 to wipe out $23.5 million, but the IRS said no. Next, Snipes argued that the IRS abused its discretion. His most famous tax case, of course, was his criminal trial. In fact, he was one of the more high profile criminal tax defendants in recent memory, facing an all-out prosecution on multiple serious felony tax evasion counts.

Wesley Snipes attends the LA Premiere of “The Equalizer 2” at the TCL Chinese Theatre on Tuesday, July 17, 2018, in Los Angeles. (Photo by Richard Shotwell/Invision/AP)

In 2008, Snipes was convicted of three misdemeanor counts of failing to file tax returns. He got jail time, reporting to McKean Federal Correctional Institution on December 9, 2010. He finished at an adjacent minimum security Club Fed, and was released in April 2013. During 1999 through 2001, Snipes avoided $7 million in taxes by listening to an accountant and anti-tax advocate who claimed  you did not legally have to pay taxes. Eddie Ray Kahn and Douglas P. Rosile were convicted of tax fraud and conspiracy, and they both drew longer prison terms than Snipes. Snipes was making about $40 million from 1999 to 2004 that not paying taxes was hard to fathom.

Yet the big victory for Snipes was that he was acquitted of felony tax fraud and conspiracy charges. Although he didn’t file false tax returns, even his misdemeanor convictions meant a sentence of 3 years. Snipes argued that his sentence was unreasonable, that he couldn’t get a fair trial in Ocala, Florida because of his race, etc. Even the U.S. Supreme Court turned him down. Yet most of Mr. Snipes’ fights with the IRS have been over civil tax collections. With defendants convicted in tax cases, there can be a spillover impact. The IRS wants to collect what it is owed in the criminal plea agreement or court order, and may send other bills too.

Snipes’ was trying to resolve all his tax debts and move on, so he resorted to taking the IRS to court. The IRS made assessments in 2013, going back more than 10 years:

  • 1999 – $177,263.99
  • 2001 – $2,573,977.70
  • 2002 – $1,497,644.97
  • 2003 – $4,576,925.66
  • 2004 – $5,625,612.45
  • 2005 – $3,526,946.38
  • 2006 – $5,777,543.18

Mr. Snipes requested a Collection Due Process Hearing (filing IRS Form 12153) seeking an offer-in-compromise or installment agreement. He was trying to work it out with the IRS. He even paid off the two amounts the IRS wanted for 1999 and 2002. In early 2014, Snipes made the IRS an offer of about $842K, or 4% of the roughly $23.5M tax debt. The IRS didn’t think that was enough. The IRS tried to verify his income and assets, claiming that Snipes used a shell game of trusts and other entities. Snipes accused the IRS of making arbitrary determinations, and claimed the IRS was abusing its discretion in not cutting him a deal. The procedural bickering continued.

By 2016, the Tax Court had rejected motions by both Snipes and by the IRS, and sent the case back to IRS Appeals. Eventually, the IRS said it would take about $9.5M to settle it. That wasn’t a bad deal, but Snipes stuck with his original offer of $842,061.  The IRS rejected it, and an IRS manager did too. Snipes went back to Tax Court arguing that the IRS abused its discretion. Amid more procedural wrangling, the Tax Court seemed to have an easy time upholding the IRS and rejecting Snipes’ claims. The IRS simply didn’t abuse its discretion, and that was that. One of the factors was cooperation. The IRS could not track down all the assets and determine who owned what, and Snipes was apparently not much help.

Snipes also tried arguing “economic hardship.” But the court said no to that too. It can work if there is a long-term illness, medical condition, or disability making you incapable of earning a living, if it is “reasonably foreseeable that your financial resources will be exhausted providing for care and support during the course of the condition.” Did Snipes fit that mold? Hardly. Another ground is if your monthly income is exhausted by providing for care of dependents without other means of support. Even with some assets, there can be economic hardship if you are unable to borrow against the equity in your assets, and if liquidating the assets would render  you unable to meet basic living expenses.

Again, the court didn’t think Snipes fit into any of these sympathetic situations. He didn’t fit the bill. Speaking of bills, with interest continuing to run, Snipes may want to take his tax arguments back to the drawing board.

via The Tax Lawyer

In Weinstein Sex Harassment Settlements, Taxes Await Plaintiffs

The fact that settlement talks may be starting between Harvey Weinstein, his namesake company and some plaintiffs won’t make most people think about taxes. But before anyone signs a settlement agreement, they should. After all, just about everything is taxed. Sexual harassment might be verbal, physical or both. And it might impact victims in a variety of ways. Those are some of the reasons there is no one-size-fits-all solution to the tax issues in this context. The tax treatment of litigation damages is varied and complex. But the rule for compensatory damages for personal physical injuries is supposed to be easy. They are tax free under Section 104 of the tax code.

Harvey Weinstein, former co-chairman of the Weinstein Co., arrives at state supreme court in New York, U.S., on Thursday, Oct. 11, 2018. Weinstein’s lawyer, Benjamin Brafman, has said in court filings that prosecutors withheld evidence that would have made the grand jury think twice about charging him, such as friendly emails one accuser sent after the alleged rape. Photographer: Peter Foley/Bloomberg

Yet exactly what is “physical” isn’t clear. For that reason, many sexual harassment victims where there is little or no physical contact usually have to pay taxes on their recoveries. Some of it seems to be semantics. If you make claims for emotional distress, your damages are taxable. If you claim the defendant caused you to become physically sick, those damages can be tax free. If emotional distress causes you to be physically sick, that is taxable. The order of events and how you describe them matters to the IRS. If you are physically sick or physically injured, and your sickness or injury produces emotional distress, those emotional distress damages should be tax free.

Wording in the settlement agreement is important, and so are IRS Form 1099. Some of the line-drawing comes from a footnote in the legislative history to the tax code adding the ‘physical’ requirement. It says “emotional distress” includes physical symptoms, such as insomnia, headaches, and stomach disorders, which may result from such emotional distress. See H. Conf. Rept. 104-737, at 301 n. 56 (1996). Tax free money is better than taxable money, and the wording in settlement agreements can sometimes matter in a very big way. However, you don’t want to face claims by the IRS or state tax authorities several years later, adding interest and penalties. If you have to pay tax, there’s a double whammy. You might assume that if you have a contingent fee lawyer, at least the lawyer’s fees are not income to you.

However, plaintiffs who use contingent fee lawyers are treated as receiving 100% of the settlement, even if their lawyer takes 40% off the top. The Supreme Court said so in Commissioner v. Banks, 543 U.S. 426 (2005). That means plaintiffs must figure a way to deduct the fees. In 2004, Congress enacted an above the line deduction for legal fees in employment cases, and many harassment cases arise in employment. Since 1994, plaintiffs in employment cases have been taxed on their net recoveries, not their gross, but only if they properly claim this above the line deduction. In sex harassment cases, though, that is now on hold.

Starting in 2018, if a sexual harassment settlement is confidential, the defendant cannot deduct legal fees or the settlement amount. However, it unintentionally seems to also prevent plaintiffs from being able to deduct their own legal fees. The Repeal the Trump Tax Hike on Victims of Sexual Harassment Act of 2018 would change that, making clear that the plaintiffs can deduct their legal fees. But the bill has not yet been passed.

Whenever possible, get some tax advice before your settlement is documented. The IRS isn’t bound by the parties’ tax characterization, but it is often respected if reasonable. And once the documents are signed it will be too late to try to address it. The interactions between physical and emotional injuries and sicknesses are starting to be explored. Some plaintiffs in employment suits have had settlements classified as tax-free. In one case, stress at work produced a heart attack, physical sickness that qualified for tax free treatment. In another, stressful conditions made a worker’s pre-existing multiple sclerosis worse, and that too was considered tax-free physical sickness.

via The Tax Lawyer

How Long Can IRS Audit? Tips To Cut Years And Audit Risks

No one wants to be audited by the IRS, and it is only natural to worry about it. Even if you think your tax return is pristine, gathering receipts is no fun, nor is explaining what you did and why. If your returns have unusual or aggressive items, it can be way worse. So how long must you worry? It pays to know how far back you can be audited, and there are steps you can take to cut your risk. But let’s start with the basics. The IRS usually has three years after you file to audit you. But there are many exceptions that give the IRS six years or longer.

IRS Audit report and calculator on a desk.

The three years is doubled to six if you omitted more than 25% of your income. For years, there was a debate over what it means to omit income from your return. Taxpayers and some courts said “omit” means leave off, as in don’t report. But the IRS said it was much broader, including reporting that has the effect of an omission of income. Say you sell a piece of property for $3M, claiming that your basis (what you invested in the property) was $1.5M. In fact, your basis was only $500,000. The effect of your basis overstatement was that you paid tax on only $1.5M of gain, when you should have paid tax on $2.5M.

In U.S. v. Home Concrete & Supply, LLC, the Supreme Court slapped down the IRS, holding that overstating your basis is not the same as omitting income. The Supreme Court said 3 years was plenty for the IRS to audit. Then, Congress overruled the Supreme Court, and gave the IRS six years in such a case. Six years is a long time. Filing your tax return early won’t help either. The time periods can be even longer in some cases. The IRS has no time limit if you never file a return or file fraudulently. Even so, the practical limit for the IRS to go back is usually six years.

Another scary rule is that the IRS can audit forever if you omit certain tax forms. Plus, once a tax assessment is made, the IRS collection statute is typically 10 years. And, in some cases that ten years can essentially be renewed. That’s one reason the IRS can sometimes go back an astounding 30 years! In Beeler v. Commissioner, the Tax Court held Mr. Beeler responsible for 30 year-old payroll tax penalties.

Figuring out the applicable statute of limitations that applies to your situation–and then waiting it out–can be nerve-wracking. An audit can involve targeted questions and requests of proof of particular items only. Alternatively, audits can also cover the waterfront, asking for proof of virtually every line item. Frequently, the IRS says it needs more time to audit. The IRS will ask you to sign a form extending the statute of limitations, usually for a year. If you don’t sign, the IRS will send you a tax bill, usually based on unfavorable assumptions. Most tax advisers generally tell clients to agree to the extension. However, it’s best to get some professional advice about your own situation. You may be able to limit the time or scope of the extension.

Another hot button that impacts the statute of limitations involves offshore accounts. The IRS goes after offshore income and assets in a big way, and that dovetails with another IRS audit rule. The IRS also gets six years to audit if you omitted more than $5,000 of foreign income (say, interest on an overseas account). That matches the audit period for FBARs, annual offshore bank account reports that can carry civil and even criminal penalties far worse than those for tax evasion.

For all these reasons, be careful and keep good records. You should keep copies of your old tax returns forever. But after a time–many people say seven years–you should be able to throw out records and receipts. Yet some records such as improvements to property that go into your basis, are exceptions. If you remodel your kitchen and sell your house 20 years later, the receipts for your remodeling job are still relevant to your tax return.

via The Tax Lawyer