Highlights From Green’s 2020 Trader Tax Guide

January 7, 2020 | By: Robert A. Green, CPA | Read it on

 

Use Green’s 2020 Trader Tax Guide to receive every trader tax break you’re entitled to on your 2019 tax returns. Our 2020 guide covers the 2017 Tax Cuts and Jobs Act’s impact on investors, traders, and investment managers. Learn various smart moves to make in 2020.

Whether you prepare your 2019 tax returns as a trader or investor, this guide can help. Even though it may be too late for some tax breaks on 2019 tax returns, you can still use this guide to execute these tax strategies and elections for tax-year 2020.

Tax Cuts and Jobs Act

Tax Cuts and Jobs Act (TCJA) was enacted on Dec. 22, 2017, and the law changes took effect in the 2018 tax year.

Like many small business owners, traders eligible for trader tax status (TTS) restructured their business for 2019 and 2020 to take advantage of TCJA. Two tax changes caught their eye: The 20% deduction on qualified business income (QBI) in pass-through entities, and suspended investment fees and expenses, which makes TTS even more crucial. (TCJA continues to allow itemized deductions for investment-interest expenses and stock borrow fees.)

TCJA didn’t change trader tax matters, including business expense treatment, Section 475 MTM ordinary gain or loss treatment, and wash-sale loss adjustments on securities; it didn’t change TTS S-Corps’, Solo 401(k) retirement contributions and health insurance deductions, either. TCJA also retains the lower Section 1256 60/40 capital gains tax rates; the Section 1256 loss carryback election; Section 988 forex ordinary gain or loss; and tax treatment on financial products including options, ETFs, ETNs, swaps, precious metals, and more.

2018 and 2019 tax forms

TCJA required significant revisions to the 2018 income tax forms. Some of those changes confused taxpayers, so the IRS revised the 2019 tax forms. The redesigned two-page 2018 Form 1040 resembled a postcard because the IRS moved many sections to six new 2018 Schedules (Form 1040). It was a block-building approach with the elimination of Form 1040-EZ and 1040-A.

The 2019 Form 1040 has three schedules, not six. The IRS moved some items back onto the Form 1040.

The IRS significantly changed Schedule A (Itemized Deductions). TCJA suspended “certain miscellaneous itemized deductions subject to the 2% floor.” These deductions were included in “Job Expenses and Certain Miscellaneous Deductions” on the 2017 Schedule A, lines 21 through 24. The revised 2018 Schedule A deleted these deductions, including job expenses, investment fees and expenses, and tax compliance fees and expenses.

The 2017 Schedule A also had “Other Miscellaneous Deductions,” not subject to the 2% floor, on line 28. That’s where investors reported stock-borrow fees, which are not investment fees and expenses. The 2018 Schedule A changed the name to “Other Itemized Deductions” on line 16.

TCJA introduced a new 20% deduction on qualified business income for 2018, but the IRS did not draft a tax form for it. Taxpayers used a worksheet for the calculation and reported a “qualified business income deduction” on the 2018 Form 1040, page 2, line 9. For 2019, the IRS introduced Form 8995 (Qualified Business Income Deduction Simplified Computation) and Form 8995-A (Qualified Business Income Deduction).

Business traders fare better

By default, the IRS lumps all traders into “investor tax status,” and investors get penalized in the tax code — more so with TCJA. Investors have restricted investment interest expense deductions, and investment fees and expenses are suspended. Investors have capital-loss limitations against ordinary income ($3,000 per year), and wash-sale loss deferrals; they do not have the Section 475 MTM election option or health insurance and retirement plan deduction strategies. Investors benefit from lower long-term capital gains rates (0%, 15%, and 20%) on positions held 12 months or more before sale. If active traders have segregated long-term investment positions, this is available to them as well.

Business traders eligible for TTS are entitled to many tax breaks. A sole proprietor (individual) TTS trader deducts business expenses and is entitled to elect Section 475 MTM ordinary gain or loss treatment. However, to deduct health insurance and retirement plan contributions, a TTS trader needs an S-Corp to create earned income with officer compensation.

Don’t confuse TTS with the related tax-treatment election of Section 475 MTM accounting. The 475 election converts new capital gains and losses into business ordinary gains and losses, avoiding the $3,000 capital loss limitation. Only qualified business traders may use Section 475 MTM; investors may not. Section 475 trades are also exempt from wash-sale loss adjustments. The 20% deduction on qualified business income includes Section 475 ordinary income but excludes capital gains, interest, and dividend income.

A business trader can assess and claim TTS after year-end and even going back three open tax years. But business traders may only use Section 475 MTM if they filed an election on time, either by April 15 of the current year (i.e., April 15, 2019 for 2019) or within 75 days of inception of a new taxpayer (i.e., a new entity). For more on TTS, see Chapter 1.

Can traders deduct trading losses?

Deducting trading losses depends on the instrument traded, the trader’s tax status, and various elections.

Many traders bought this guide hoping to find a way to deduct their 2019 trading losses. Maybe they qualify for TTS, but that only gives them the right to deduct trading business expenses.

Securities, Section 1256 contracts, ETNs, and cryptocurrency trading receive capital gain/loss treatment by default. If a TTS trader did not file a Section 475 election on securities and/or commodities on time (i.e., by April 15, 2019), or have Section 475 from a prior year, he is stuck with capital loss treatment on securities and Section 1256 contracts. Section 475 does not apply to ETN prepaid forward contracts, which are not securities, or cryptocurrencies, which are intangible property.

Capital losses offset capital gains without limitation, whether short-term or long-term, but a net capital loss on Schedule D is limited to $3,000 per year against other income. Excess capital losses are carried over to the subsequent tax year(s).

Once taxpayers get in the capital loss carryover trap, a problem they often face is how to use up the carryover in the following year(s). If a taxpayer elects Section 475 by April 15, 2020, the 2020 business trading gains will be ordinary rather than capital. Remember, only capital gains can offset capital loss carryovers. That creates a predicament addressed in Chapter 2on Section 475 MTM. Once a trader has a capital loss carryover hole, she needs a capital gains ladder to climb out of it and a Section 475 election to prevent digging an even bigger one. The IRS allows revocation of Section 475 elections if a Section 475 trader later decides he or she wants capital gain/loss treatment again.

Traders with capital losses from Section 1256 contracts (such as futures) may be in luck if they had gains in Section 1256 contracts in the prior three tax years. On the top of Form 6781, traders can file a Section 1256 loss carryback election. This allows taxpayers to offset their current-year losses against prior-year 1256 gains to receive a refund of taxes paid in prior years. Business traders may elect Section 475 MTM on Section 1256 contracts, but most elect it on securities only so they can retain the lower 60/40 capital gains tax rates on Section 1256 gains, where 60% is considered a long-term capital gain, even on day trades.

Taxpayers with losses trading forex contracts in the off-exchange Interbank market may be in luck. By default, Section 988 for forex transactions receives ordinary gain or loss treatment, which means the capital-loss limitation doesn’t apply. However, without TTS, the forex loss isn’t a business loss and therefore can’t be included in a net operating loss (NOL) calculation — potentially making it a wasted loss since it also can’t be added to the capital loss carryover. If taxpayer has another source of taxable income, the forex ordinary loss offsets it; the concern is when there is negative taxable income. Forex traders can file a contemporaneous “capital gains and losses” election in their books and records to opt out of Section 988, which is wise when capital loss carryovers exist. Contemporaneous means in advance — not after the fact using hindsight. In some cases, this election qualifies for Section 1256(g) lower 60/40 capital gains tax rates on major pairs, not minors.

A TTS trader using Section 475 on securities has ordinary loss treatment, which avoids wash-sale loss adjustments and the $3,000 capital loss limitation. Section 475 ordinary losses offset income of any kind, and a net operating loss carries forward to subsequent tax year(s). TCJA’s “excess business loss” (EBL) limitation for 2019 is $510,000 married and $255,000 other taxpayers applies to Section 475 ordinary losses and trading expenses. Add an EBL to an NOL carryforward. See TCJA changes in Chapter 17.

Tax treatment on financial products

There are complexities in sorting through different tax-treatment rules and tax rates. It’s often hard to tell what falls into each category. To help our readers with this, we cover the many trading instruments and their tax treatment in Chapter 3.

Securities have realized gain and loss treatment and are subject to wash-sale rules and the $3,000 per year capital loss limitation on individual tax returns.

Section 1256 contracts — including regulated futures contracts on U.S. commodities exchanges — are marked to market by default, so there are no wash-sale adjustments, and they receive lower 60/40 capital gains tax rates.

Options have a wide range of tax treatment. An option is a derivative of an underlying financial instrument and the tax treatment is generally the same. Equity options are taxed the same as equities, which are securities. Index options are derivatives of indexes, and broad-based indexes are Section 1256 contracts. Simple and complex equity option trades have special tax rules on holding period, adjustments, and more.

Forex receives ordinary gain or loss treatment on realized trades (including rollovers), unless a contemporaneous capital gains election is filed. In some cases, lower 60/40 capital gains tax rates on majors may apply.

Physical precious metals are collectibles; if these capital assets are held over one year, sales are subject to the collectibles capital gains rate capped at 28%.

Cryptocurrencies are intangible property taxed like securities on Form 8949, but wash-sale loss and Section 475 rules do not apply because they are not securities.

Foreign futures are taxed like securities unless the IRS issues a revenue ruling allowing Section 1256 tax benefits.

Several brokerage firms classify options on volatility exchange-traded notes (ETNs) and options on volatility exchange-traded funds (ETFs) structured as publicly traded partnerships as “equity options” taxed as securities. There is substantial authority to treat these CBOE-listed options as “non-equity options” eligible for Section 1256 contract treatment. Volatility ETNs have special tax treatment: ETNs structured as prepaid forward contracts are not securities, whereas, ETNs structured as debt instruments are.

Don’t solely rely on broker 1099-Bs: There are opportunities to switch to lower 60/40 tax capital gains rates in Section 1256, use Section 475 ordinary loss treatment if elected on time, and report wash-sale losses differently. Vital 2020 tax elections need to be made on time. See Chapter 3.

Entities for traders

Entities can solidify TTS, unlock health insurance and retirement plan deductions, gain flexibility with a Section 475 election or revocation, prevent wash-sale losses with individual and IRA accounts, and enhance a QBI deduction on Section 475 income less trading expenses. An entity return consolidates trading activity on a pass-through tax return, making life easier for traders, accountants, and the IRS. Trading in an entity allows individually held investments to be separate from business trading. It operates as a separate taxpayer yet is inexpensive and straightforward to set up and manage.

An LLC with S-Corp election is generally the best choice for a single or married couple seeking health insurance and retirement plan deductions. See Chapter 7.

Retirement plans for traders

Annual tax-deductible contributions up to $62,000 for 2019 and $63,500 for 2020 to a TTS S-Corp Solo 401(k) retirement plan generally saves traders significantly more in income taxes than it costs in payroll taxes (FICA and Medicare). Trading gains aren’t earned income, so traders use an S-Corp to pay officer compensation.

There’s also an option for a Solo 401(k) Roth: If you are willing to forgo the tax deduction, you’ll enjoy permanent tax-free status on contributions and growth within the plan. See Chapter 8.

20% deduction on qualified business income

TCJA introduced a new tax deduction for pass-through businesses, including sole proprietors, partnerships and S-Corps. Subject to haircuts and limitations, a pass-through business could be eligible for a 20% deduction on qualified business income (QBI).

Traders eligible for TTS are a “specified service activity,” which means if their taxable income is above an income cap, they won’t receive a QBI deduction. The taxable income (TI) cap is $421,400/$210,700 (married/other taxpayers) for 2019, and $426,600/$213,300 (married/other taxpayers) for 2020. The phase-out range below the cap is $100,000/$50,000 (married/other taxpayers), in which the QBI deduction phases out for specified service activities. The W-2 wage and property basis limitations also apply within the phase-out range. Investment managers are specified service activities, too.

QBI for traders includes Section 475 ordinary income and loss and trading business expenses. QBI excludes capital gains and losses, Section 988 forex and swap ordinary income or loss, dividends, and interest income.

TCJA favors non-service businesses, which are not subject to an income cap. The W-2 wage and property basis limitations apply above the TI threshold of $321,400/$160,700 (married/other taxpayers) for 2019, and $326,600/$163,300 (married/other taxpayers) for 2020. The IRS adjusts the annual TI income threshold for inflation each year. For more information, see Chapter 17.

Affordable Care Act

TCJA did not change the Affordable Care Act’s (ACA) 3.8% Medicare tax on unearned income. The net investment tax (NIT) applies on net investment income (NII) for individual taxpayers with modified AGI over $250,000 (married) and $200,000 (single). The threshold is not indexed for inflation. Traders can reduce NIT by deducting TTS trading expenses, including salaries paid to them and their spouses. Traders may also reduce NII with investment expenses that are allowed on Schedule A, such as investment-interest expense and stock borrow fees. Investment fees and other investment expenses suspended from Schedule A also are not deductible for NII.

ACA’s individual health insurance mandate and shared responsibility fee for non-compliance, exchange subsidies, and premium tax credits continue to apply for 2019 and 2020. However, TCJA reduced the shared responsibility fee to $0 starting in 2019.

For more information, see Chapter 9 and Chapter 15.

Investment management carried interest

TCJA modified the carried interest tax break for investment managers in investment partnerships, lengthening their holding period on profit allocation of long-term capital gains (LTCG) from one year to three years. If the manager also invests capital in the partnership, he or she has LTCG after one year on that interest. The three-year rule only applies to the investment manager’s profit allocation — carried interest. Investors still have LTCG based on one year.

Investment partnerships include hedge funds, commodity pools, private equity funds, and real estate partnerships. Many hedge funds don’t hold securities for more than three years, whereas, private equity, real estate partnerships, and venture capital funds do.

Investors also benefit from carried interest in investment partnerships. TCJA suspended “certain miscellaneous itemized deductions subject to the 2% floor,” which includes investment fees and expenses. Separately managed account investors are out of luck, but hedge fund investors can limit the negative impact by using carried-interest tax breaks. Carried interest reduces a hedge fund investor’s capital gains instead of having a suspended incentive fee deduction.

International tax matters

When it comes to global tax matters, we focus on the following types of traders: U.S. residents living abroad, U.S. residents with international investments, U.S. residents moving to U.S. territories like Puerto Rico (with substantial tax breaks), U.S. residents surrendering citizenship or green cards, and nonresident aliens investing in the U.S. with individual U.S. brokerage accounts or through an entity. See Chapter 14.

 


Execute S-Corp Officer Compensation With Employee Deductions Before Year-End

December 10, 2019 | By: Robert A. Green, CPA

TTS traders need an S-Corp trading company to arrange health insurance and retirement plan deductions. These deductions require earned income or self-employment income. Unlike trading gains, S-Corp salary is considered earned income.

The S-Corp must execute officer compensation, in conjunction with employee benefit deductions, through formal payroll tax compliance before the year-end 2019. Otherwise, traders miss the boat. TTS is an absolute must since an S-Corp investment company cannot have tax-deductible wages, health insurance, and retirement plan contributions. This S-Corp is not required to have “reasonable compensation” as other types of businesses are, so a TTS trader may determine officer compensation based on how much to reimburse for health insurance, and how much they want to contribute to a retirement plan. If you are in the QBI phase-out range, you might wish to have higher wages to increase a QBI deduction. For payroll tax compliance services, I recommend paychex.com; it has a dedicated team for our TTS S-Corp clients. Sole proprietor and partnership TTS traders cannot pay salaries to 2% or more owners.

TTS S-Corps may only deduct health insurance for the months the S-Corp was operational and qualified for TTS. Employer-provided health insurance, including Cobra, is not deductible. It doesn’t need to be profitable for the health insurance deduction.

A taxpayer can deduct a contribution to a health savings account (HSA) without TTS or earned income. HSA contribution limits for 2019 are $3,500 individual and $7,100 for family coverage. There’s an additional $1,000 for age 55 or older. Some employers offer a flexible spending account (FSA) for covering health care copayments, deductibles, some drugs, and other health care costs. Both HSAs and FSAs must be fully funded and utilized before the year-end.

TTS S-Corps formed later in the year can unlock a retirement plan deduction by paying sufficient officer compensation in December when results for the year are evident. Traders should only fund a retirement plan from trading income, not losses.

You must open a Solo 401(k) retirement plan for a TTS S-Corp with a financial intermediary before the year-end 2019. Plan to pay the 2019 100%-deductible elective deferral amount up to a maximum of $19,000 (or $25,000 if age 50 or older) with December payroll. That elective deferral is due by the end of January 2020. You can fund the 25% profit-sharing plan (PSP) portion of the S-Corp Solo 401(k) up to a maximum of $37,000 by the due date of the 2019 S-Corp tax return, including extensions, which means Sept. 15, 2020. The maximum PSP contribution requires wages of $148,000 ($37,000 divided by 25% defined contribution rate). Tax planning calculations will show the projected outcome of income tax savings vs. payroll tax costs for the various options.

Consider a Solo 401(k) Roth, where the contribution is not deductible, but the contribution and growth within the Roth are permanently tax-free. Traditional plans have a tax deduction upfront, and all distributions are subject to ordinary income taxes in retirement. Traditional retirement plans have required minimum distributions (RMD) by age 70½, whereas Roth plans don’t have RMD.

Setting up a TTS S-Corp for 2020
If you missed out on employee benefits in 2019, then consider an LLC with S-Corp election for 2020. You can form a single-member LLC by mid-December 2019, obtain the employee identification number (EIN), and open the LLC brokerage account before year-end to begin trading in it on Jan. 1, 2020. The single-member LLC is a disregarded entity for 2019, which avoids an entity tax return filing for the 2019 partial year. A spouse can be added as a member of the LLC on Jan. 1, 2020, which means the LLC will file a partnership return for 2020. If you want health insurance and retirement plan deductions, then your single-member or spousal-member LLC should submit a 2020 S-Corp election within 75-days of Jan. 1, 2020. The S-Corp should also consider making a Section 475 MTM election on securities only for 2020 within 75 days of Jan. 1, 2020.

Clients of our firm GNM should sign up for S-Corp Tax Compliance (Traders) and work with their assigned CPA before the year-end.

If you want to set up an LLC in December with S-Corp election for 2020, start with a 45-minute paid consultation with Robert A. Green, CPA. You can purchase our entity formation service afterward.


Tax Planning At Year-End Generates The Most Savings

October 26, 2019 | By: Robert A. Green, CPA | Read it on

The best way to reduce income taxes is with year-end tax planning. Don’t wait until February when you begin preparation of 2019 tax returns; that’s too late for many tax savings strategies.

If you have an S-Corp that is eligible for trader tax status (TTS), don’t miss that section further down below, which includes essential year-end transactions, including formal payroll tax compliance for officer compensation. That unlocks the health insurance and or retirement plan deductions.

Defer income and accelerate tax deductions
Consider the time-honored strategy of deferring income and accelerating tax deductions if you don’t expect your taxable income to decline in 2020. We expect tax rates to be the same for 2020, although the IRS will adjust the tax brackets for inflation. Enjoy the time-value of money with income deferral.

Year-end tax planning is a challenge for traders because they have wide fluctuations in trading results, making it difficult to forecast their income. Those expecting to be in a lower tax bracket in 2020 should consider income deferral strategies. Conversely, a 2019 TTS trader with ordinary losses, waiting to be in a higher tax bracket in 2020, might want to consider income acceleration strategies.

Taxpayers with trader tax status in 2019 should consider accelerating trading business expenses, such as purchasing business equipment with full expensing.

Don’t assume that accelerating itemized deductions is also a smart move; there may be two problems. TCJA suspended and curtailed various itemized deductions after 2017, so there is no sense in expediting a non-deductible item. Even with the acceleration of deductible expenses, many taxpayers will be better off using the 2019 standard deduction of $24,400 married or $12,200 single. If itemized deductions are below the standard deduction, consider a strategy to “bunch” them into one year and take the standard deduction in other years.

Accelerate income and defer certain deductions
A TTS trader with substantial ordinary losses (Section 475) under the “excess business loss limitation” (EBL, see below) should consider accelerating income to soak up the allowable business loss, instead of having an NOL carryover. Try to advance enough income to use the standard deduction and take advantage of lower tax brackets. Be sure to stay below the thresholds for unlocking various types of AGI-dependent deductions and credits.

Roth IRA conversion: Convert a traditional IRA into a Roth IRA before year-end to accelerate income. The conversion income is taxable in 2019, but the 10% excise tax on early withdrawals before age 59½ is avoided providing you pay the conversion taxes from outside the Roth plan. One concern is that TCJA repealed the recharacterization option; you can no longer reverse it if the plan assets decline after conversion. There isn’t an income limit for making Roth IRA conversions, whereas there is for making regular Roth IRA contributions. For example, a taxpayer filing single has a $405,000 TTS/475 ordinary loss. However, the excess business loss limitation is $255,000, and $150,000 is an NOL carryover. Consider a Roth conversion to soak up most of the $255,000 allowed business loss, and leave enough income to use the standard deduction and lower tax brackets.

Sell winning positions: Another way a trader can accelerate income is to sell open winning positions to realize capital gains.

Consider selling long-term capital gain positions. The 2019 long-term capital gains rates are 0% for taxable income under $39,375 single, and $78,750 married filing jointly. The 15% capital gains rate applies to taxable income up to $434,550 for filing single and $488,850 married filing jointly. The top bracket rate of 20% applies above those amounts.

Net investment tax: Investment fees and expenses are not deductible for calculating net investment income (NII) for the Affordable Care Act (ACA) 3.8% net investment tax (NIT) on unearned income. NIT only applies to individuals with NII and modified adjusted gross income (AGI) exceeding $200,000 single, $250,000 married filing jointly, or $125,000 married filing separately. The IRS does not index these ACA thresholds for inflation. NII includes capital gains and Section 475 ordinary income.

Business expenses and itemized deduction vs. standard deduction

Business expenses: TTS traders are entitled to deduct business expenses and home-office deductions from gross income. The home office deduction requires income, except for the mortgage interest and real property tax portion. The SALT cap on state and local taxes does not apply to the home office deduction. TCJA expanded full expensing of business property; traders can deduct 100% of these costs in the year of acquisition, providing they place the item into service before year-end. If you have TTS in 2019, considering going on a shopping spree before January 1. There is no sense deferring TTS expenses because you cannot be sure you will qualify for TTS in 2020.

Employee business expenses: Ask your employer if they have an “accountable plan” for reimbursing employee-business costs. You must “use it or lose it” before the year-end. TCJA suspended unreimbursed employee business expenses. A TTS S-Corp should use an accountable plan to reimburse employee business expenses since the trader/owner is an employee of the S-Corp.

Unreimbursed partnership expenses: Partners in LLCs taxed as partnerships can deduct unreimbursed partnership expenses (UPE). That is how they usually deduct home office expenses. UPE is more convenient than using an S-Corp accountable plan because the partner can arrange the UPE after the year-end. The IRS doesn’t want S-Corps to use UPE.

SALT cap: TCJA’s most contentious provision was capping state and local income, sales, and property taxes (SALT) at $10,000 per year ($5,000 for married filing separately) – and not indexing it for inflation. Many high-tax states continue to contest the SALT cap, but they haven’t prevailed in court. The IRS reinforced the new law by blocking various states’ attempts to recast SALT payments as charitable contributions, or payroll tax as a business expense. Stay tuned to news updates about SALT.

Investment fees and expenses: TCJA suspended all miscellaneous itemized deductions subject to the 2% floor, which includes investment fees and expenses. TCJA left just two itemized deductions for investors: Investment-interest expenses limited to investment income, with the excess as a carryover, and stock borrow fees for short-sellers.

Standard deduction: TCJA roughly doubled the 2018 standard deduction and suspended and curtailed several itemized deductions. The 2019 standard deduction is $12,200 single, $24,400 married, and $18,350 head of household. There is an additional standard deduction of $1,300 for the aged or the blind. Many more taxpayers will use the standard deduction, which might simplify their tax compliance work. For convenience sake, some taxpayers may feel inclined to stop tracking itemized deductions because they figure they will use the standard deduction. Don’t overlook the impact of these deductions on state tax filings where you might get some tax relief for itemizing deductions.

Estimated income taxes and AMT

Estimated income taxes: If you already reached the SALT cap, you don’t need to prepay 2019 state estimated income taxes by December 31, 2019. Pay federal and state estimated taxes owed when due by January 15, 2020, with the balance of your tax liabilities payable by April 15, 2020. You can gain six months of additional time by filing an automatic extension on time, but late-payment penalties and interest will apply on any tax balance due. (See Tax Extensions: 12 Tips To Save You Money.)

Many traders skip making quarterly estimated tax payments during the year, figuring they might incur trading losses later in the year. Catch up with the Q4 estimate due by January 15. Some rely on the safe harbor exception to cover their prior year taxes. TTS S-Corp traders should consider withholding additional taxes on year-end paychecks in connection with retirement plan contributions, which helps avoid underestimated tax penalties since the IRS treats wage withholding as being made throughout the year.

AMT: In prior years, taxpayers had to figure out how much they could prepay their state without triggering alternative minimum tax (AMT) since state taxes are not deductible for AMT taxable income. It’s easier in 2019 with SALT capped at $10,000 and because TCJA raised the 2019 AMT exemptions to $510,300 single and $1,020,600 married filing jointly. Taxpayers subject to AMT should not accelerate AMT preference items.

Avoid wash sale loss adjustments

Wash sales: Taxpayers must report wash sale (WS) loss adjustments on securities based on substantially identical positions across all accounts, including IRAs. Conversely, brokers assess WS only on identical positions per the one account. Active securities traders should use a trade accounting program or service to identify potential WS loss problems, especially going into year-end.

In taxable accounts, a trader can break the chain by selling the position before year-end and not repurchasing a substantially identical position 30 days before or after in any of his taxable or IRA accounts. Avoid WS between taxable and IRA accounts throughout the year, as that is otherwise a permanent WS loss. (Starting a new entity effective January 1, 2020, can break the chain on individual account WS at year-end 2019 provided you don’t purposely avoid WS with the related party entity.)

WS losses might be preferable to capital loss carryovers at year-end 2019 for TTS traders. A Section 475 election in 2020 converts year-end 2019 WS losses on TTS positions (not investment positions) into ordinary losses in 2020. That’s better than a capital loss carryover into 2020, which might give you pause to making a Section 475 election. You want a clean slate with no remaining capital losses before electing Section 475 ordinary income and loss. (See How To Avoid Taxes On Wash Sale Losses.)

Trader tax status and Section 475

Trader tax status: If you qualify for TTS (business expense treatment — no election needed) in 2019, accelerate trading expenses into that qualification period as a sole proprietor or entity. If you don’t qualify until 2020, try to defer trading expenses until then. You may also capitalize and amortize (expense) Section 195 startup costs and Section 248 organization costs in the new TTS business, going back six months before commencement. TTS is a prerequisite for electing and using Section 475 MTM. (See How Traders Get Enormous Tax Deductions, And Investors Do Not.)

Section 475 MTM: TTS traders choose Section 475 on securities for exemption from wash-sale loss rules and the $3,000 capital loss limitation — and to be eligible for the 20% QBI deduction. To make a 2019 Section 475 election, existing individual taxpayers had to file an election statement with the IRS by April 15, 2019 (March 15 for existing S-Corps and partnerships). If they filed that election statement on time, they need to complete the election process by submitting a 2019 Form 3115 with their 2019 tax return. Those who missed the 2019 election deadline may want to consider the election for 2020. Capital loss carryovers are a concern; use them up against capital gains but not Section 475 ordinary income. Once you make a 475 election, it remains in effect; you don’t have to elect it every year. You are entitled to revoke a 475 election, in the same manner, you elect it. If you stop qualifying for TTS, then 475 treatment is suspended until you requalify.

If you make a Section 475 election by April 15, 2020, it takes effect on January 1, 2020. In converting from the realization (cash) method to the mark-to-market (MTM) method, you need to make a Section 481(a) adjustment on January 1, 2020. It’s unrealized capital gains, and losses on open TTS securities positions held on December 31, 2019. Do not apply Section 475 to investment positions. If you are not a TTS trader as of year-end 2019, then you won’t have a Section 481(a) adjustment. (See Section 481(a) Positive Adjustment Spread Period Changes.)

A “new taxpayer” entity can elect Section 475 within 75 days of inception. That would come in handy if you missed the individual sole proprietor deadline (April 15, 2019) for choosing Section 475. Forming a new entity on November 1, 2019, or later, is too late for establishing TTS for the 2019 short calendar year. Consider waiting until January 1, 2020, for starting a new entity with TTS and electing Section 475.

20% deduction on qualified business income
In August 2018, the IRS issued proposed reliance regulations (Proposed §1.199A) for the TCJA’s 20% deduction on qualified business income (QBI) in pass-through entities. On January 18, 2019, the IRS issued the final 199A regs. The proposed and final regulations confirm that traders eligible for TTS are a “specified service activity,” which means if their taxable income is above an income cap, they won’t receive a QBI deduction. The 2019 taxable income (TI) cap is $421,400/$210,700 (married/other taxpayers). The phase-out range below the cap is $100,000/$50,000 (married/other taxpayers), in which the QBI deduction phases out for specified service activities. The W-2 wage and property basis limitations also apply within the phase-out range. Investment managers are specified service activities, too.

QBI includes Section 475 ordinary income and loss, and trading business expenses. QBI excluded capital gains and losses, Section 988 forex and swap ordinary income or loss, dividends, and interest income. Our firm took a favorable position on QBI for traders. (See A Rationale For Using QBI Tax Treatment For Traders.)

TCJA favors non-service businesses, which are not subject to an income cap. The W-2 wage and property basis limitations apply above the 2019 TI threshold of $321,400/$160,700 (married/other taxpayers). The IRS adjusts the annual TI income threshold for inflation each year.

Taxpayers might be able to increase the QBI deduction with smart year-end planning. If taxable income falls within the phase-out range for a specified service activity, or even above for a non-service business, you might need higher wages, including officer compensation, to avoid a W-2 wage limitation on the QBI deduction. Deferring income can also help get under various QBI restrictions and thresholds.

Net operating losses and the Section 1256 loss carryback election

Net operating losses: Section 475 ordinary losses and TTS business expenses contribute to net operating loss (NOL) carryforwards, which are limited to 80% of taxable income in the subsequent year(s). Get immediate use of some or all of NOLs with a Roth IRA conversion before year-end and other income acceleration strategies. TCJA repealed NOL carrybacks after 2017 with one exception; farmers may carry back an NOL two tax years. TCJA made NOL carryforwards unlimited, changing the carryforward period from 20 years. Repealing NOL carrybacks negatively impacts TTS traders using 475 ordinary loss treatment. We helped traders obtain significant NOL refunds before 2018, which helped them remain in business. An “excess business loss” (EBL) over the limitation is an NOL carryforward, and accelerating non-business income won’t avoid EBL. (See EBL below.)

Section 1256 loss carryback election: The only remaining carryback for traders is a Section 1256 loss carryback to the prior three tax years, offset against 1256 gains, not other types of income. Any loss remaining is carried forward. Consider making a Section 1256 loss carryback election on a 2019 Form 6781 timely filed with a 2019 tax return.

There are other tax advantages to trading Section 1256 contracts. They have lower 60/40 capital gains tax rates, meaning 60% (including day trades) use the lower long-term capital gains rate, and 40% use the short-term rate, which is the ordinary tax rate. At the maximum tax brackets for 2019, the top Section 1256 contract tax rate is 26.8% —10.2% lower than the highest ordinary rate of 37%. Section 1256 tax rates are 4.2% to 12% lower vs. ordinary rates depending on which tax bracket applies. Section 1256 contracts are marked-to-market (MTM), so you don’t have to do tax-loss selling at year-end. (See Trading Futures & Other Section 1256 Contracts Has Tax Advantages.)

Limitations on excess business losses and business interest expense

Excess business loss limitation: TCJA included an “excess business loss” (EBL) limitation of $500,000/$250,000 (married/other taxpayers) for 2018. (The 2019 inflation-adjusted limit is $510,000/$255,000 (married/other taxpayers). Aggregate EBL from all pass-through businesses: A profitable company can offset another business with losses to remain under the limit. Include wage income in aggregate EBL. Other types of income and non-business losses do not affect the EBL calculation (i.e., capital gains and losses). EBL over the limit is an NOL carryforward.

Example of EBL limitation: TTS/475 trader filing single has an ordinary loss of $500,000 for 2019. It’s considered a business loss. He has income from wages of $100,000, so his net EBL is $400,000. The 2019 EBL limitation is $255,000 and the 2019 NOL carryover to 2020 is $145,000 ($400,000 minus $255,000).

Business interest expense: TCJA introduced a limitation on deducting business interest expense in Section 163(j). The 30% limitation should not impact most TTS traders because the $25 million three-year average “gross receipts” threshold applies to net trading gains, not proceeds. That’s good news because if gross receipts used total sales proceeds on trades, then a TTS trader with trading losses might have a business interest expense limitation. With net trading gains being the standard, only more substantial hedge funds might be impacted.

S-Corp officer compensation, health insurance, and retirement plan deductions
TTS traders need an S-Corp trading company to arrange health insurance and retirement plan deductions. These deductions require earned income or self-employment income, and trading gains are not that. S-Corp salary is considered earned income.

2019 S-Corp: The S-Corp must execute officer compensation, in conjunction with employee benefit deductions, through formal payroll tax compliance before the year-end 2019. Otherwise, traders miss the boat. TTS is an absolute must since an S-Corp investment company cannot have tax-deductible wages, health insurance, and retirement plan contributions. This S-Corp is not required to have “reasonable compensation” as other types of businesses are, so a TTS trader may determine officer compensation based on how much to reimburse for health insurance, and how much they want to contribute to a retirement plan. Keep an eye out for the QBI deduction; if you are in the QBI phase-out range, you might wish to have higher wages to increase a QBI deduction. For payroll tax compliance services, I recommend paychex.com; they have a dedicated team for our TTS S-Corp clients. Sole proprietor and partnership TTS traders cannot pay salaries to 2% or more owners.

Health insurance deduction: A TTS S-Corp may only deduct health insurance for the months the S-Corp was operational and qualified for TTS. Employer-provided health insurance, including Cobra, is not deductible. A TTS S-Corp doesn’t need to be profitable for the health insurance deduction.

Health Savings Account: A taxpayer can deduct a contribution to a health savings account (HSA) without needing TTS eligibility or earned income. HSA contribution limits for 2019 are $3,500 individual and $7,100 for family coverage. There’s an additional $1,000 for age 55 or older. Fully fund and utilize the HSA before year-end.

Flexible Spending Account: Some employers offer a flexible spending account (FSA) for covering health care copayments, deductibles, some drugs, and other health care costs. Fully fund and utilize the FSA before year-end.

Solo 401(k) retirement plan: A TTS S-Corp formed later in the year can unlock a retirement plan deduction for an entire year by paying sufficient officer compensation in December when results for the year are evident. Traders should only fund a retirement plan from trading income, not losses.

You must establish (open) a Solo 401(k) retirement plan for a TTS S-Corp with a financial intermediary before the year-end 2019. Plan to pay the 2019 100%-deductible elective deferral amount up to a maximum of $19,000 (or $25,000 if age 50 or older) with December payroll. That elective deferral is due by the end of January 2020. You can fund the 25% profit-sharing plan (PSP) portion of the S-Corp Solo 401(k) up to a maximum of $37,000 by the due date of the 2019 S-Corp tax return, including extensions, which means September 15, 2020. The maximum PSP contribution requires wages of $148,000 ($37,000 divided by 25% defined contribution rate). Do tax planning calculations to see the projected outcome of income tax savings vs. payroll tax costs for the various options.

Consider a Solo 401(k) Roth, where the contribution is not deductible, but the contribution and growth within the Roth are permanently tax-free. Traditional plans have a tax deduction upfront, and all distributions are subject to ordinary income taxes in retirement. Traditional retirement plans have required minimum distributions (RMD) by age 70 ½, whereas Roth plans don’t have RMD.

Setting up a TTS S-Corp for 2020
If you missed out on employee benefits in 2019, then consider an LLC with S-Corp election for 2020. If you wait to start your entity formation process on January 1, 2020, you won’t be ready to trade in an entity account on January 1, 2020. Instead, you can form a single-member LLC by mid-December 2019, obtain the employee identification number (EIN), and open the LLC brokerage account before year-end. The single-member LLC is a disregarded entity for 2019, which avoids an entity tax return filing for the 2019 partial year. If desired, add your spouse as a member of the LLC on January 1, 2020, which means the LLC will file a partnership return. If you want health insurance and retirement plan deductions, then your single-member or spousal-member LLC should submit a 2020 S-Corp election by March 15, 2020. The S-Corp should also consider making a Section 475 MTM election on securities only for 2020 by March 15.

Tax-loss selling of financial instruments
If you own an investment or trading portfolio, you have the opportunity to reduce capital gains taxes via “tax-loss selling.” If you realized significant short-term capital gains year-to-date in 2019 and have open positions with substantial unrealized capital losses, you should consider selling (realizing) some of those losses to reduce 2019 capital gains taxes. Don’t repurchase the losing position 30 days before or after, as that would negate the tax loss with wash-sale loss rules.

The IRS has rules to prevent the deferral of income and acceleration of losses in offsetting positions that lack sufficient economic risk. These rules include straddles, the constructive sale rule, and shorting against the box. Also, be aware of “constructive receipt of income” — you cannot receive payment for services, turn your back on that income, and defer it to the next tax year.

Tax-loss selling is inefficient for short-term positions that reduce long-term capital gains. It’s also a moot point with Section 1256 and Section 475 positions since they are mark-to-market positions reporting realized and unrealized gains and losses.

Married couples should compare filing joint vs. separate
Each year, married couples choose between “married filing jointly” (MFJ) vs. “married filing separately” (MFS). TCJA fixed several inequities in filing status, including the tax brackets by making single, MFJ and MFS equivalent, except for divergence at the top rate of 37% for single filers, retaining some of the marriage penalty. There are other issues to consider, too.

Married couples may be able to improve QBI deductions, AGI, and other income-threshold dependent deductions, and credits with MFS in 2019. It’s wise to enter each spouse’s income, gain, loss, and expense separately and have the tax planning and preparation software compare MFJ vs. MFS. In a community property state, there are special rules for allocating income between spouses.

Filing MFS might unlock a QBI deduction, where one spouse might price the other spouse out of a QBI deduction based on exceeding the income cap for a specified service activity.

Miscellaneous considerations for individuals
Sell off passive-loss activities to utilize suspended passive-activity losses.

Maximize contributions to retirement plans. That lowers AGI and other income thresholds, which can unlock more of a QBI deduction, reduce net investment tax, and unlock credits and other tax benefits. Consider non-deductible IRA contributions.

The IRS has many obstacles to deferring income, including passive-activity loss rules, a requirement that certain taxpayers use the accrual method of accounting and limitations on charitable contributions. TCJA allows more businesses to use the cash method.

Consider a charitable remainder trust to bunch philanthropic contributions for itemizing deductions. (Ask Fidelity or Schwab about it.)

Donate appreciated securities to charity: You get a charitable deduction at the FMV and avoid capital gains taxes. (This is a favorite strategy by billionaires, and you can use it, too.)

Retirees must take required minimum distributions (RMD) by age 70½ unless it’s a Roth IRA. Per TCJA, consider directing your traditional retirement plan to make “qualified charitable distributions” (QCD). That satisfies the RMD rule with the equivalent of an offsetting charitable deduction, allowing you to take the standard deduction rather than itemize charitable contributions.

TCJA improves family tax planning: Section 529 qualified tuition plans now can be used to pay for tuition at an elementary or secondary public, private or religious school, up to $10,000 per year (check with your state). The 2019 annual gift exclusion is $15,000, and its $155,000 to noncitizen spouses; the 2019 unified credit for federal estate tax is $11.40 million per person, and “step-up in basis” rules still avoid capital gains taxes on inherited appreciated property. TTS traders should also consider hiring adult children as employees. (See How To Save Taxes With Children.)

TCJA created Qualified Opportunity Zones (QOZ) “to spur economic development and job creation in distressed communities throughout the country and U.S. possessions by providing tax benefits to investors who invest eligible capital into these communities. Taxpayers may defer tax on eligible capital gains by making an appropriate investment in a Qualified Opportunity Fund and meeting other requirements,” per Opportunity Zones Frequently Asked Questions.)

Adam Manning CPA contributed to this blog post. 

This blog post is an updated version of chapter 9 on tax planning in Green’s 2019 Trader Tax GuideFree upgrade: If you purchase Green’s 2019 Trader Tax Guide after October 15, 2019, we will email you online access to Green’s 2020 Trader Tax Guide around the middle of January 2020.

Our CPAs are standing by in November and December to help clients with 2019 year-end tax planning. Our tax compliance service includes tax planning and preparation, and we look forward to helping you execute the above tax strategies. Please contact us soon.

Consider a 45-minute consultation with Robert A. Green, CPA to discuss eligibility for TTS and if an entity if helpful to you. Upgrade to our entity formation service after, if warranted.

Join my upcoming Webinar on November 13, 2019, or watch the recording after to learn more about this content: Tax Planning At Year-End Generates The Most Savings

 

 


How To Save Taxes With Children

October 8, 2019 | By: Robert A. Green, CPA

Children are lovely, but they also cost a lot of money on childcare and education costs. With careful tax planning, you can generate significant tax savings.

Consider shifting a portion of investment income from the parent’s tax return to the children. However, avoid having too high unearned income for younger children as that might trigger the “kiddie tax,” which defeats the intended purpose. (See below: The “kiddie tax” rules and how they affect you.)

If you have a family business, consider hiring your children to shift earned income to the children’s lower tax brackets. For sole proprietorships and LLC/partnerships, you might also save social security taxes. (See below: Tax benefits of putting junior family members on the payroll.)

There is a litany of tax planning strategies to consider while saving for education, including college. These include qualified tuition programs (“529 plans”), tax-exempt bonds, Coverdell education savings accounts, tuition tax credits, employer educational assistance programs, college expense payments by grandparents and others, the student loan interest deduction, borrowing against retirement plan accounts, and withdrawals from retirement plan accounts. (See below: Tax planning for college, and Qualified tuition programs-”529 plans”)

As a working parent, you might qualify for the dependent care credit or an employer-provided dependent care flexible spending account (FSA). Determine which one is better for your tax bracket and needs. (See below: Dependent care credit/dependent care flexible spending account.)

The new tax law, TCJA, made the child tax credit (CTC) more valuable, and more taxpayers should qualify for this credit. (See below: Child tax credit.)

Client Letters from Thomson Reuters/Tax & Accounting:

  • The “kiddie tax” rules and how they affect you (page 3)
  • Tax benefits of putting junior family members on the payroll (page 5)
  • Tax planning for college (page 7)
  • Qualified tuition programs-”529 plans” (page 14)
  • Dependent care credit/dependent care flexible spending account (page 16)
  • Child tax credit (page 20)

We are emailing a PDF file containing the above Client Letters, so sign up for our Email List.

If you would like to discuss any of these tax planning strategies, contact your assigned CPA in our firm, or consider a consultation. Contact us with any questions.

Thank you,

Robert A. Green, CPA
CEO, GreenTraderTax.com
Managing Member, Green, Neuschwander & Manning, LLC

 


What You Trade Can Make A World Of Tax Difference

September 29, 2019 | By: Robert A. Green, CPA | Read it on

There’s a bevy of financial products to trade with a wide assortment of tax treatment. Traders have access to U.S. and international equities, futures and other Section 1256 contracts, options, ETFs, ETNs, forex, precious metals, foreign futures, cryptocurrencies, and swap contracts. Broker-issued Form 1099-Bs might not provide the best available tax treatment, and in some cases, there are no 1099s issued.

Securities
Securities traders have ordinary tax rates on short-term capital gains, wash sale loss adjustments, capital-loss limitations, and accounting challenges.

Securities include:
- U.S. and international equities (stocks)
- U.S. and foreign equity (stock) options
- narrow-based indexes (an index made up of nine or fewer securities)
- options on narrow-based indexes
- securities ETFs structured as registered investment companies (RIC)
- options on securities ETF RICs
- commodities ETFs structured as publicly traded partnerships (PTP)
- volatility ETNs, structured as debt instruments
- bonds
- mutual funds
- single-stock futures

Securities don’t include:
- Section 1256 contracts
- precious metals (collectibles)
- ETFs structured as publicly traded trusts (PTT)
- CBOE-listed options on ETF PTPs and ETF PTTs
- CBOE-listed options on ETNs
- volatility ETNs structured as prepaid forward contracts (PFC)
- cryptocurrencies (intangible property)
- forex (spot and forwards contracts)
- swap contracts

The IRS taxes securities transactions when a taxpayer closes an open trade – hence the term “realization method.” Taxpayers can defer capital gains by holding open securities positions at year-end.

With “tax-loss selling,” investors realize losses before year-end. Be careful not to re-enter those positions within 31 days; otherwise, the planned tax loss might defer to 2020 as a wash sale loss adjustment.

Short-term capital gains (STCG) use ordinary tax rates, currently up to 37% for 2019 and 2020. Long-term capital gains (LTCG) rates are significantly lower, and they apply to sales of securities held for 12 months or more. The LTCG rates are 0% for the 10% and 12% ordinary brackets, 15% in the middle brackets, and 20% in the top 37% bracket. (See 2019 Tax Brackets.)

The mark-to-market (MTM) accounting method is different. MTM taxes realized and unrealized capital gains and losses at year-end. Traders eligible for trader tax status (TTS) are entitled to elect Section 475 MTM ordinary gain or loss on securities and or commodities. (See How Traders Get Enormous Tax Deductions, And Investors Do Not.) Section 1256 contracts have MTM by default. (See 1256 contracts below).

Capital losses, including capital loss carryovers, offset capital gains without a limitation. A net capital loss for the year is limited to $3,000 against other income like wages. Capital loss carryovers don’t expire; they are deferred tax assets. If you have excess capital losses, don’t rush to elect Section 475 ordinary income as you need capital gains to use up capital losses. Look at all sources of capital gains, including sales of real property and intangible property. Trading entities and hedge funds can pass capital gains to the owner’s tax return.

Section 1256 Contracts
Section 1256 contracts enjoy lower 60/40 capital gains tax rates, summary tax reporting, and easier mark-to-market accounting.

Section 1256 contracts include:
- U.S. regulated futures contracts (RFCs)
- options on U.S. RFCs
- U.S. broad-based indexes made up of 10 or more underlying securities – also known as stock index futures
- options on U.S. broad-based indexes
- foreign futures if granted Section 1256 treatment in an IRS revenue ruling (see list)
- non-equity options (a catchall)
- CBOE-listed options on commodity ETF publicly traded partnerships (PTP)
- CBOE-listed options on precious metals ETF publicly traded trusts (PTT)
- CBOE-listed options on volatility ETN prepaid forward contracts and ETN debt instruments
- forward forex contracts with the opt-out election into Section 1256(g) on the major pairs, for which futures trade (we make a case for spot forex, too)
- forex OTC options (Wright court)

Section 1256 contracts have lower 60/40 capital gains tax rates: 60% (including day trades) subject to lower long-term capital gains rates, and 40% taxed as short-term capital gains using the ordinary rate. At the maximum tax bracket for 2019 and 2020, the blended 60/40 rate is 26.8% — 10.2% lower than the highest ordinary bracket of 37%. There are significant tax savings throughout the income brackets. The LTCG rate in the lowest two ordinary brackets is 0%. (See our table Section 1256 tax rates vs. ordinary rates.)

Section 1256 contracts are marked-to-market (MTM) daily. For tax purposes, MTM reports both realized activity from throughout the year and unrealized gains and losses on open trading positions at year-end. The 1099-B is one page with summary reporting.

There is a Section 1256 loss carryback election. Rather than use the 1256 loss in the current year, deduct 1256 losses on amended tax return filings, applied against Section 1256 gains only. Form 1045 is better than 1040X. It’s a three-year carryback; unused amounts carry forward. TCJA repealed most NOL carrybacks, so this is the only remaining carryback opportunity for traders. (See Trading Futures & Other Section 1256 Contracts Has Tax Advantages.)

Options
Tax treatment for options is diverse, including simple (outright) and complex trades with multiple legs.

Options taxed as securities:
- equity (stock) options
- options on narrow-based indexes
- options on securities ETFs RIC

Options taxed as 1256 contracts:
- non-equity options (a catchall)
- options on U.S. regulated futures contracts and broad-based indexes
- CBOE-listed options on commodity ETF publicly traded partnerships (PTP)
- CBOE-listed options on precious metals ETF publicly traded trusts (PTT)
- CBOE-listed options on volatility ETN prepaid forward contracts and ETN debt instruments
- forex OTC options (Wright appeals court)

Generally, options listed on a commodities exchange, a qualified board or exchange (QBE), are a 1256 contract unless the reference is a single stock or a narrow-based stock index. A securities ETF RIC is like a stock in this regard.

Three things can happen with outright option trades:

- Trade option (closing transaction).
- The option expires (lapses).
- Exercise the option.

There are special rules for the holding period for long-term capital gains. (See Tax Treatment Can Be Tricky With Options and ETFs.)

Exchange-Traded Funds (ETF)
Securities, commodities, and precious metals ETFs use different structures, and tax treatment varies.

Securities ETFs: Securities ETFs are registered investment companies (RICs). Selling a securities ETF is deemed a sale of a security, calling for short-term and long-term capital gains tax treatment on the realization method. As a security, wash sale loss adjustments or Section 475 apply if elected.

Commodities ETFs: Commodities ETFs use the publicly traded partnership (PTP) structure. PTPs issue annual Schedule K-1s passing through Section 1256 tax treatment on Section 1256 transactions to investors, as well as other taxable items. Selling a commodity ETF is deemed a sale of a security, calling for short-term and long-term capital gains tax treatment using the realization method. It’s a security, so it’s subject to WS losses and a 475 election if elected.

Taxpayers invested in commodities ETFs should adjust cost-basis on Form 8949 (capital gains and losses). That ensures they don’t double count Schedule K-1 pass-through income or loss. Form 1099-B and trade accounting software do not make this adjustment, so you need to make a manual adjustment.

Physically backed precious metals ETFs: They usually choose the publicly traded trust (PTT) structure (also known as a grantor trust). A PTT issues an annual Schedule K-1, passing through tax treatment to the investor, which in this case is the “collectibles” rate on sales of physically-backed precious metals (such as gold bullion). Selling a precious metal ETF is deemed disposition of a precious metal, which is a collectible. For collectibles held over one year (long-term), sales use the “collectibles” rate —capped at 28%. Short-term capital gains use the ordinary rate. Precious metals and ETFs backed by precious metals are not securities, so they are not subject to WS loss adjustments, or Section 475 if elected.

Forex
Forex transactions start off receiving an ordinary gain or loss treatment, as dictated by Section 988 (foreign currency transactions). Ordinary losses are generally better than capital losses, providing the trader has other income to absorb the loss. With eligibility for TTS, an excess ordinary business loss is a net operating loss (NOL) carryforward.

Section 988 allows traders to file a capital gains election to opt-out of Section 988 ordinary treatment. It must be done contemporaneously in your books and records. You can make, or retract, the opt-out election on a “good to cancel” basis at any time during the year. If you have a capital loss carryover, then consider a capital gains election.

The capital gains election on forex forwards allows the trader to use lower 60/40 capital gains rates in Section 1256(g). There are two requirements: It must be on “major currencies,” and the trader must not take or make delivery. “Major currencies” means currency pairs, which also trade as futures on U.S. commodities exchanges. We make a case for including “spot” forex in Section 1256(g). (See A Case For Retail Forex Traders Using Section 1256(g) Lower 60/40 Tax Rates.)

Foreign futures
By default, futures contracts listed on international exchanges are not Section 1256 contracts. If the international exchange wants Section 1256 tax treatment, they must obtain an IRS Revenue Ruling granting 1256 treatment. Only a handful of international futures exchanges have Section 1256 treatment: Eurex, LIFFE, ICE Futures Europe, and ICE Futures Canada. Foreign futures are otherwise ST or LT capital gains. (See Tax treatment for foreign futures.)

Precious metals
Physical precious metals are “collectibles,” which are a particular class of capital assets. If you hold collectibles over one year (long-term), sales are taxed at the “collectibles” tax rate — capped at 28%. (If your ordinary rate is lower, use that.) If you hold collectibles one year or less, the short-term capital gains ordinary tax rate applies no different from the regular STCG tax rate.

Volatility products
There are many different types of volatility-based financial products to trade, and tax treatment varies.

CBOE Volatility Index (VIX) futures are Section 1256 contracts with lower 60/40 MTM tax rates. The NYSE-traded SVXY is an exchange-traded fund (ETF), taxed as a security. The iPath S&P 500 VIX Short-Term Futures (VXX) is an exchange-traded note (ETN).

Volatility ETNs. Many issuers structure volatility ETNs as prepaid forward contracts (PFC), which provides a deferral of taxes until sale (realization). Long-term capital gains rates apply if held 12 months or longer. (i.e., VXX). However, prepaid forward contracts are not securities. Therefore, they are not subject to WS loss adjustments and Section 475 if elected. Many 1099-Bs treat ETN PFC as securities subject to WS. Consider departing from the 1099-B with footnote disclosure. Some ETNs, like UGAZ, are debt instruments taxed as securities, which means they are subject to WS losses and Section 475 if chosen. (Check the tax section of the ETN prospectus and see Other Financial Products.)

Cryptocurrencies
Selling, exchanging, or using cryptocurrency triggers capital gains and losses for traders. The IRS treats cryptocurrencies as intangible property; not a security or a commodity.

The realization method applies to short-term vs. long-term capital gains and losses. If you invested in cryptocurrencies and sold, exchanged, or spent some during the year, you have to report a capital gain or loss on each transaction. Include cryptocurrency-to-currency sales, crypto-to-alt-crypto trades, and purchases of goods or services using crypto.

U.S. cryptocurrency exchanges issue a Form 1099-K to accounts with transactions over a certain threshold. The problem for the IRS is that many cryptocurrency transactions on exchanges around the world are not evident for tax reporting. Cryptocurrency investors should download all crypto transactions into a crypto accounting program that is IRS-compliant.

Wash sales do not apply to intangible property. Use the first-in-first-out (FIFO) accounting method. Intangible property should use the specific identification method, but that requires broker confirmation of each trade, which is not possible.

TCJA restricted Section 1031 like-kind exchanges to real property, starting in 2018. That rules out using like-kind exchange on crypto-to-crypto trades (i.e., Bitcoin for Ethereum). It’s questionable whether crypto traders could have used Section 1031 before 2018 to defer capital gains taxes. The IRS promised the public more advice on crypto, and it recently mailed tax “education” notices to crypto traders. I hope the IRS addresses Section 1031, hard forks or chain splits, and several other open questions. (See Watch Out Cryptocurrency Owners; The IRS Is On The Hunt.)

Swap contracts
The Dodd-Frank financial regulation law promised to clear private swap transactions on exchanges to protect the markets from another swap-induced financial meltdown. Remember those credit default swaps with insufficient margin? When Congress enacted Dodd-Frank, traders hoped that clearing on futures exchanges would allow Section 1256 tax treatment. They were wrong: Congress and the IRS immediately communicated that Section 1256 would not apply to swap transactions, and they confirmed ordinary gain or loss treatment.

Roger D. Lorence JD contributed to this blog post.

Join my upcoming Webinar on October 23, 2019, or watch the recording after to learn more about this content: Trader Tax Strategies 2019 Year-End Update

For more information on wash sales and Section 475, see How Traders Get Enormous Tax Deductions, And Investors Do Not.

For more in-depth information, see Green’s 2019 Trader Tax Guide


How Traders Get Enormous Tax Deductions, And Investors Do Not

September 28, 2019 | By: Robert A. Green, CPA | Read it on

Traders eligible for “trader tax status” (TTS) deduct business expenses, startup costs, and home office deductions. A TTS trader may elect Section 475 for exemption from wash sale loss adjustments (deferrals), the $3,000 capital loss limitation, and to be eligible for a 20% qualified business income (QBI) deduction. Trading income is not self-employment income, so TTS traders don’t owe SE taxes. Using an S-Corp, TTS traders create earned income to maximize health insurance and or retirement plan deductions.

Lacking TTS, investors get peanuts in the tax code. TCJA, the new tax code suspended investment fees and expenses along with all other miscellaneous itemized deductions subject to the 2% floor. Two itemized-deductions for investors survived tax reform: Investment-interest expense limited to investment income, and stock-borrow fees. With the state and local tax (SALT) limitation and roughly-doubled standard deduction, many investors don’t get any tax deductions for investment-related expenses.

The IRS does not permit investors to elect Section 475, so they are stuck with wash sale loss adjustments, and the $3,000 capital loss limitation. Short-term capital gains are subject to ordinary tax brackets. Investors benefit from long-term capital gains, providing the investor holds a position open for 12-months or more. Long-term capital gains rates are 0%, 15% and 20% for 2019 and 2020. Traders can have segregated investments for LTCG, too. 

How to qualify for trader tax status
Satisfy the below requirements based on my analysis of tax court cases and years of experience working with traders. 

· Substantial volume – at least four total trades per day, 15 per week, 60 per month, and 720 per year annualized (Poppe court). Count open and closing trades separately.
· Frequency – a trade execution on 75% of available trading days. That’s close to four days per week.
· Average holding period under 31 days (Endicott court bright-line test).
The above factors are the “big three.”
· Continuous trading with few sporadic lapses.
· Time – four hours per day, including trading, research, and administration.
· Intention to run a business and to make a living. It doesn’t have to be a primary living.
· Business setup (multiple trading devices, monitors, and a home office).
· Materiality (Pattern Day Trader minimum for securities of $25,000; $15,000 otherwise).

Assess your facts and circumstances for TTS towards the year-end. If you rise to the level of TTS, then deduct business expenses, startup costs, and home office expenses on Schedule C, a partnership, or S-Corp tax return. TTS business expenses do not require an election with the IRS; whereas, Section 475 does require a timely election. TTS does not convert capital losses into ordinary losses; a Section 475 election is necessary for ordinary gain or loss treatment. 

TTS business expenses
If you are eligible for TTS, you are entitled to deduct the below items, and more:

· Tangible personal property up to $2,500 per item, including computers, monitors, desks, and mobile devices.
· Section 179 (100%) depreciation, 100% bonus depreciation, and or regular depreciation.
· Amortization (expensing) of startup costs (Section 195), organization costs (Section 248), and software.
· Education expenses after the commencement of TTS.
· Section 195 startup costs may include education expenses within six months of beginning TTS.
· Publications, subscriptions, market data, charting services, self-created automated trading systems, cloud computing, professional services (accountants and attorneys), chat rooms, mentors, coaches, supplies, media, communications, travel, meals, seminars, conferences, supplies, assistants, office rent, and consultants.
· Home-office expenses for the business portion of your home. (See Home Office Tax Deductions Are Fantastic: Learn How To Do It.)
· Margin interest expenses. (Not limited to investment income like investment interest is.)
· Stock-borrow fees and other costs for short-sellers.

Wash sale loss adjustments
Wash sale loss adjustments on securities cause headaches and potentially higher tax bills. If a taxpayer repurchases substantially identical securities within 30 days before or after realizing a tax loss on securities, the IRS uses the wash sale (WS) loss rule. That defers a tax loss to the replacement position’s cost basis.

For example, if you sell Apple stock at a tax loss on December 15, 2019, and repurchase a substantially identical position (Apple stock or option) on January 10, 2020, the 2019 wash sale loss defers to 2020. It’s critical to avoid WS at year-end in taxable accounts by breaking the 30-day chain. Sell the position by year-end for a tax loss, and don’t repurchase a substantially identical position for 31 days. If you want to catch a rally in January, then consider it may not be so bad to defer a loss as it’s just a timing issue.

It’s essential to prevent WS losses throughout the year between taxable and IRA accounts because it’s a permanent WS loss. The IRS does not allow a WS loss to be added to cost basis in the IRA. 

There are other ways to avoid WS. TTS traders can elect Section 475 on securities to be exempt from WS. Traders can choose to trade instruments that are not considered securities, including futures, forex, precious metals, and cryptocurrencies. 

WS rules for taxpayers and brokers are different. The IRS requires taxpayers to calculate WS losses based on substantially identical securities positions (i.e., Apple equity vs. Apple options), across all taxpayer’s brokerage accounts, including IRAs and spousal accounts if married/filing joint. Conversely, the IRS requires brokers to calculate WS based on identical securities (an exact symbol) per the one brokerage account. This apples vs. oranges is problematic since the IRS seeks to match broker 1099-Bs with taxpayer Form 8949s. Many accountants and taxpayers do not know these differences in the rules. Consider trade accounting software that is compliant with IRS rules for taxpayers, and you should explain overall differences in tax return footnotes. (See How To Avoid Taxes On Wash Sale Losses.)

Elect Section 475 for additional tax benefits
The IRS permits TTS traders to elect Section 475 ordinary gain or loss treatment on securities and or commodities. Section 475 trades are exempt from wash sale loss rules, and the $3,000 capital loss limitation. Short-term capital gains use the same ordinary rate as Section 475, except 475 also unlocks a potential QBI deduction. There are significant tax benefits on Section 475 ordinary losses vs. capital losses. TTS traders can deduct a 475 ordinary business loss against wages and other income; thereby bypassing the capital loss limitation. Excess ordinary losses are a net operating loss (NOL) carry forward.

TCJA introduced a 20% qualified business income (QBI) deduction for sole proprietors, partnerships, and S-Corps. TTS trading is a “specified service trade or business” (SSTB) subject to a taxable income threshold, phase-in and phase-out range, and taxable income cap. If you exceed the taxable income cap, you don’t get a QBI deduction on an SSTB. QBI includes Section 475 income/loss net of trading business expenses; whereas, QBI excludes capital gains/losses, interest, dividends, and other investment income. (See A Rationale For Using QBI Tax Treatment For Traders.)

Most futures traders prefer to skip a 475 election to retain Section 1256 60/40 capital gains rates; they don’t want ordinary income. However, if you have a significant trading loss in 1256 contracts, then consider a 475 election on commodities. You can revoke a Section 475 election in a subsequent year, in the same manner, you elected it. (See more about Section 475 and how to choose it in my blog post, Traders Elect Section 475 For Massive Tax Savings.)

Join my upcoming Webinar on October 23, 2019, or watch the recording after to learn more about this content: Trader Tax Strategies 2019 Year-End Update

For more in-depth information, see Green’s 2019 Trader Tax Guide


Home Office Tax Deductions Are Fantastic: Learn How To Do It

August 24, 2019 | By: Robert A. Green, CPA | Read it on

Since 1999, the home-office deduction is no longer a red flag — millions of Americans benefit from this deduction each year. Countless taxpayers run businesses from home, and the IRS understands this. The income-requirement rule also limits the use of this deduction for profitable enterprises, which appeases IRS concerns about abuse and hobby-loss businesses. Before the IRS liberalized home-office deduction rules in 1999, a more stringent requirement was that business taxpayers needed to meet clients in their home office. Now, the only requirement is administration work, and another principal office outside the home doesn’t negate the deduction.

Many small-business owners, including traders eligible for trader tax status (TTS), operate from a home office. Some of them also conduct their business from job locations using cloud computing, apps, and mobile devices. They can qualify for the home office expense deduction in this situation, as well. The IRS does not permit investors to take a home office deduction.

Convert personal home costs into business expense deductions. This same concept applies to many other items such as phone, Internet, furniture, fixtures, and more. Keep in mind that business income or TTS trading gains are needed to unlock most home-office deductions. If a business doesn’t have sufficient net income, the otherwise allowable home office deductions are carried over to the following tax years. (In this situation, hopefully, the person remains in the business and has net income in subsequent years to use the carryovers.)

There are several special requirements and rules for the home office deduction. A home office must be exclusively and regularly used for business, meaning children and guests can’t use this room. Report “indirect expenses” on Form 8829 and include every expense and cost related to the home. For example, include depreciation or rent, utilities, insurance, repairs and maintenance, security, cleaning, lawn care, and more.

Include mortgage interest and real property taxes, too, and this home-office portion doesn’t require income. The remaining part of mortgage interest expense and real property taxes are Schedule A itemized deductions.

Real property taxes on Schedule A are part of the new tax law (TCJA) SALT limitation. However, the home office portion or real property tax is not subject to the SALT limitation.

To calculate the home-office deduction, take the square footage of the home office (and all related business areas such as storage, hallways, and bathrooms). Divide that by the total square footage of the home (10-15% is customary). Alternatively, taxpayers can do the apportionment based on the room’s method. Form 8829 multiplies the home-office percentage by the indirect expenses. If the business files a partnership return, report home-office expenses as unreimbursed partnership expenses (UPE) on Schedule E. For S-Corps, use an accountable reimbursement plan before year-end.

Per Thomson Reuters/Tax & Accounting Client Letter (see list below):

“Sales of homes with home offices. If you sell-at a profit-a home that contains, or contained, a home office, the otherwise available $250,000/$500,000 exclusion for gain on the sale of a principal residence won’t apply to the portion of your profit equal to the amount of depreciation you claimed on the home office.”

Depreciation expenses on the home office over the years save taxes at ordinary income tax rates. Recapture of depreciation on a sale of the principal residence is taxed up to a 25% capital gains rate, which is unique to Section 1250 property. Tax deferral is another value. The rest of the home enjoys the exclusion of capital gain up to the limit.

If a taxpayer sells his principal residence at a loss, the net loss is not deductible. However, the recapture of depreciation income might not exceed the loss amount, meaning there is no taxable income from depreciation recapture to report on the tax return.

TCJA capped state and local income taxes, sales taxes, real property taxes, and personal property taxes (SALT) itemized deductions on Schedule A at $10,000 per year (any combination thereof), and $5,000 for married filing separately. TCJA also reduced itemized deduction limits on mortgage interest expenses and casualty losses.

Home office tax benefits for employees
Employers require some employees to work from a home office. The new tax law (TCJA) suspended unreimbursed employee business expenses as itemized deductions. That leaves only one other way to arrange a tax benefit for home office expenses. An employee can seek reimbursement from an employer for home office expenses through an accountable reimbursement plan. The employer deducts home office expenses and does not include this payment on the employee’s W-2 as taxable income.

Our below Thomson Reuters/Tax & Accounting Client Letter for “telecommuting employees” states:

“The convenience of the employer requirement is satisfied if: you maintain your home office as a condition of employment-in other words, if your employer specifically requires you to maintain the home office and work there; your home office is necessary for the functioning of your employer’s business; or your home office is necessary to allow you to perform your duties as an employee properly. The convenience of the employer requirement means that you must maintain your home office for your employer’s convenience, and not for your own. This requirement isn’t satisfied if your use of a home office is merely “appropriate and helpful” in doing your job.”

Client Letters from Thomson Reuters/Tax & Accounting:

  • Home office expense deduction for a self-employed taxpayer
  • Exclusion of gain on sale or exchange of principal residence
  • How the home sale exclusion applies to a residence used for residential and business (nonresidential) purposes or to produce rental income
  • Office at home for telecommuting employees
  • Converting a home into rental property

For access to these Client Letters from Thomson Reuters/Tax & Accounting, please join our email list. We send bulk emails a few times per month and include links to Client Letters.


How To Be Eligible For Independent Contractor Tax Status

August 17, 2019 | By: Robert A. Green, CPA | Read it on

There are significant tax advantages for independent contractors (IC) vs. employees.

  • ICs deduct business expenses, whereas, the new tax law (TCJA) suspended “unreimbursed employee business expenses” as miscellaneous itemized deductions.
  • ICs are eligible for TCJA’s 20% qualified business income (QBI) deduction, whereas, employees are not.
  • ICs owe 100% of social security and Medicare taxes (SE tax) on net business income, whereas employers and employees share social security and Medicare taxes 50/50 on salaries.
  • ICs are not enrolled in employer health insurance and retirement plans, whereas employees are. ICs can have individual health insurance and retirement plan AGI-deductions.

You cannot make this determination of IC vs. employee status based on your preference alone. Learn the IRS rules on worker classification. (See IRS resources and Client Letters below.)

Current developments
Some “self-employed individuals” (SEI) hire “professional employer organizations” (PEOs), known as employee leasing companies, to join the PEO payroll and employee benefit plans. The SEI reimburses the PEO for these employment costs, plus a fee. The IRS recently balked at this practice for SEIs.

IRS Chief Counsel Advice (CCA) 201916004 dated April 19, 2019, stated that PEOs could not treat SEIs as employees. PEOs should issue SEIs a Form 1099-MISC for non-employee compensation; not a W-2. This reclassification precludes the SEI from participation in a PEO employee benefit plan. The IRS does not permit sole proprietors, and partners to pay themselves wages. A partnership reports “guaranteed payments” to partners.

Trading income is unearned income. TTS traders use an S-Corp to have officer compensation for arranging employee benefits, including health insurance and retirement plans.

The IRS recently released draft 2020 Form 1099-NEC (non-employee compensation). For the 2019 tax year, a business should continue to report non-employee compensation on Form 1099-MISC box 7. The 2020 Form 1099-NEC will give the IRS more capability to track non-employee compensation. I expect the IRS to examine more companies and challenge their worker classification. Get on the right side of this issue now.

IRS Independent Contractor (Self-Employed) or Employee?
Understanding Employee vs. Contractor Designation

For access to this full blog post, which includes the above-listed Client Letters from Thomson Reuters/Tax & Accounting, please join our email list. We send bulk emails a few times per month and include links to PDFs with Client Letters.

Darren Neuschwander CPA contributed to this blog post.


How To Avoid Taxes On Wash Sale Losses

August 5, 2019 | By: Robert A. Green, CPA | Read it on

Many securities traders incur significant tax bills on phantom income caused by “wash sale losses disallowed” on form 1099-Bs. Traders are often surprised because most brokers don’t report wash sale (WS) loss calculations during the year. In this blog post, learn how to deal with WS loss adjustments and how to avoid them in the first place.

WS loss reporting on 1099-Bs is confusing
Broker 1099-Bs report “wash sale loss disallowed” (box 1g), and it’s not uncommon to see an enormous amount for an active securities trader. The 1099-B also reports “proceeds” (box 1d), “cost or other basis” (box 1e) and several other related amounts. For example, $10M proceeds minus $9.9M cost or other basis, plus $150,000 of wash sale loss disallowed, equals $250,000 of taxable capital gains. The 1099-B cover page has summary numbers, and supplemental schedules include each securities trade for all of these boxes.

The essential point is that WS loss disallowed in box 1g is for the entire tax year. However, WS losses deferred at year-end cause phantom income in the current tax year. Many WS losses during the year might fade away by year-end (see how below). Unfortunately, brokers do not report WS losses deferred at year-end, and clients need that information. If a trader uses trade accounting software, they need this information to reverse WS loss deferrals from the prior year-end on January 1 of the current tax year.

For example, two different traders can have $1M of WS loss disallowed in box 1g. Trader A doesn’t have WS losses at year-end, and she is not concerned with those adjustments during the year. She sold all open positions by year-end and did not repurchase substantially identical positions in January. Trader B also sold all positions by year-end, but he made repurchase trades in January, which triggered $50,000 of WS losses deferred at year-end. Trader B delayed the December WS loss to the subsequent tax year.

Traders need ongoing WS loss information throughout the year to prevent this predicament. Some monthly brokerage statements include cost basis amounts for month-end open positions listed on the report, and other monthly brokerage statements do not.

Most traders don’t realize they have a WS loss problem until they receive 1099-Bs in late February. That’s too late to avoid WS losses. Some traders and tax preparers import 1099-Bs into tax preparation software. Others enter the amounts to Form 8949 and then attach the 1099-B for details. If the taxpayer has cost basis adjustments, the IRS requires Form 8949; listing each securities proceeds, cost basis, WS losses, and other cost basis adjustments. However, there’s a problem relying solely on 1099-Bs because IRS WS rules for taxpayers vary from WS rules for brokers in preparing those 1099-Bs.

WS rules for taxpayers and brokers are different
Taxpayers must calculate WS losses based on “substantially identical securities” (i.e., Apple equity vs. Apple options), across all taxpayer’s brokerage accounts, including IRAs and spousal accounts if married/filing joint. Conversely, brokers calculate WS based on “identical securities” (an exact symbol) per the one brokerage account. This apples vs. oranges is problematic since the IRS seeks to match broker 1099-Bs to Form 8949 prepared by taxpayers.

Trade accounting software can help
Traders should consider using an IRS-compliant trade accounting software or a professional service using such software. Contemporaneous use of the program allows traders to avoid WS loss adjustments with potential WS loss reports. The software/service also gives taxpayers a second opinion vs. broker 1099-Bs.

Taxpayers and accountants are entitled to depart from 1099-Bs and explain why in the tax return footnotes. For example, a 1099-B might treat an ETN prepaid forward contract (i.e., BATS: VXX) as a security with wash sales. However, an ETN structured as a prepaid forward contract (PFC) is not a security, so WS losses don’t apply. A CBOE-listed option on an ETN/PFC is a “non-equity option” in Section 1256, although most 1099-Bs treat these options as securities subject to WS losses. Many brokers rely on tax treatment provided by exchanges, who try to fit financial instruments into two boxes: securities vs. section 1256 contracts.

Traders should try to reconcile Form 8949 proceeds with 1099-B proceeds. However, they should not expect to match cost-basis information, if trade accounting software calculates WS losses differently.

Trade accounting software downloads all trades, and the program automatically calculates WS losses based on IRS rules for taxpayers, not brokers. The program explains the rationale and provides details on various tax reports.

The 1099-Bs might use FIFO or specific identification and try to reflect the same accounting method in a trade accounting program.

For the first year of using trade accounting software, traders should enter open positions from the prior year-end with original-cost basis. Additionally, traders should enter deferred WS losses applied to those open positions. Traders should also enter WS losses deferred on closed-positions repurchased within 30 days in January. Trade accounting programs do not download this information from the prior year.

It would come in handy if the broker provided the WS loss deferred at year-end. If that amount was available, you could enter it as a cost basis adjustment, in addition to open positions with an original cost basis.

In the second year of use, the trade accounting program will automatically carry over open positions and wash sale loss adjustments from the prior year. Consult the program vendor and or trade accounting expert.

Jason Derbyshire of TradeLog software says: “If brokers provide detailed reporting of WS loss deferrals at year-end, TradeLog could utilize that information to help automate input into the software. This information would enable traders to accurately track those deferred losses in the software, and make more informed decisions to capture those losses, if needed, in the following tax year.”

What exactly is a wash sale loss?
A wash-sales loss is a timing issue. If you sell a security for a loss and repurchase it 30 days before or after, you cannot deduct the economic loss immediately in a taxable account. You must add the WS loss to the replacement position’s cost basis, which kicks the can (loss) down the road.

WS loss adjustments made during the year in taxable accounts might not be a problem at year-end. Some fade away. For example, a trader can trigger a WS loss every month during the year but absorb it with a significant capital gain on that security toward year-end. Additionally, the trader can “break the chain” at year-end by selling the position and not repurchasing it for 30 days.

There are also permanent WS losses triggered by IRAs, which are catastrophic. When you sell a position at a loss in a taxable account and repurchase a substantially identical position within 30 days in an IRA, there is no way to record the WS loss. Brokers don’t report these types of WS losses since they don’t calculate WS across more than one account at a time. If you trade in an IRA only (i.e., you do not trade in taxable accounts), then you don’t have these WS loss issues.

Strategies to avoid wash-sale losses
Consider a “Do Not Trade List” to prevent permanent WS between taxable and IRA accounts. For example, a trader could trade tech stocks in his taxable accounts and energy stocks in his IRA accounts.

Taxpayers can “break the chain” on WS losses at year-end in taxable accounts to avoid deferral. If a trader sells Apple equity at a loss on December 20, 2019, consider not repurchasing Apple equity or Apple equity options until January 21, 2020. That avoids the 30-day window for triggering a WS loss. In December 2018, many traders realized tax losses before year-end with a market correction. Some didn’t want to wait 30 days and miss the January 2019 rally, thereby triggering significant WS loss deferral at year-end 2018. Deferral of WS losses can become a problem if it causes a capital loss limitation in the subsequent tax year.

WS loss adjustments during the year in taxable accounts can be absorbed if traders sell/buy those open positions before year-end with a profit.

Consider a Section 475 election. Traders eligible for trader tax status (TTS) are entitled to elect Section 475 mark-to-market (MTM) accounting, which exempts them from wash-sale loss adjustments and the capital-loss limitation. I call it “tax loss insurance.” Don’t enter Section 475 trades on Form 8949; use Form 4797 Part II (ordinary gain or loss). Although Section 475 extricates securities traders from the compliance headaches of Form 8949, it does not change the requirement for reporting each trade on Form 4797.

We recommend trade accounting software to generate Form 4797. If a taxpayer elects Section 475, she will need that software to calculate a Section 481(a) adjustment, too. Even with a Section 475 election, the trader still needs to make the manual entries for open positions and opening-year WS loss adjustments mentioned earlier. The 2019 Section 475 election due date for individuals was April 15, 2019, and March 15, 2019, for existing partnerships and S-Corps.

Section 475 ordinary income is “qualified business income” (QBI). A TTS trader with 475 income net of business expenses is eligible for a 20% QBI deduction, providing the trader is under the taxable income thresholds for a “specified service business.” QBI excludes capital gains, interest, and dividend income.

Consider a new entity. Trading in an entity account might help avoid ongoing WS loss problems. The company is separate from the individual and IRA accounts for purposes of wash sales since it is a different taxpayer. The IRS is entitled to apply related party transaction rules (Section 267) if the entity purposely tries to avoid wash sales with the owner’s accounts. If the company qualifies for TTS, it can consider a Section 475 MTM election exempting it from wash sales (on TTS positions, not investment positions). A “new taxpayer” entity is entitled to elect Section 475 by internal resolution within 75 days of inception. That comes in handy after missing the 475-election deadline for individuals by April 15.

Trade accounting for securities is less complicated with a new entity since there are no opening-year manual entries for WS losses deferred from the prior year-end.

Trade Section 1256 contracts and other financial instruments that are not considered securities for tax purposes. Learn about Section 1256 contracts in my blog post: Trading Futures & Other Section 1256 Contracts Has Tax Advantages.

The following financial instruments are not securities or 1256 contracts: ETN prepaid forward contracts, cryptocurrencies, precious metals, forex, and swap contracts. Only securities are subject to wash sale loss adjustments.

GNM CPAs Darren Neuschwander, Christie Kam, and Amanda Smitson contributed to this blog post.

Learn more about wash sale loss rules in Green’s 2019 Trader Tax Guide.


Watch Out Cryptocurrency Owners, The IRS Is On The Hunt

July 31, 2019 | By: Robert A. Green, CPA | Read it on

The massive tax bust of crypto owners has begun with the IRS mailing 10,000 letters to crypto account owners. These letters educate crypto account holders about the rules and tell taxpayers to review their tax reporting for crypto transactions to be sure they reported income correctly. If necessary, taxpayers should file amended tax returns and or late returns. These tax returns should be marked with the corresponding letter type (i.e., Letter 6173, 6174 or 6174-A) and mailed to a particular IRS address. In other words, these tax filings won’t be a needle in the haystack and the IRS will take a close look. Many audits may follow.

IRS Letter 6173

“We have information that you have or had one or more accounts containing virtual currency and may not have met your U.S. tax filing and reporting requirements for transactions involving virtual currency, which include cryptocurrency and non-crypto virtual currencies.”

The IRS might know there is unreported income based on tax information obtained through enforcement actions, which include the summons against U.S. Coinbase customers. You received the letter because you didn’t file a tax return, which should have included virtual currency transactions. Alternatively, you filed a return but did not report virtual currency transactions. You must reply to this tax notice by submitting a correct late tax return or an amended return. If you disagree with the IRS, the letter requires a full explanation with a signed statement declared under penalties of perjury.

Letter 6173 is a severe tax notice, and you should not dig yourself into a bigger hole with an incorrect reply. In some cases, perjury could be a felony. The letter states, “If we don’t hear from you by the “respond by” date we may refer your tax account for examination.”

I wonder how the IRS will conduct its audits of virtual currency transactions. They will need a list of all coin exchanges and private wallets and probably have to use trade accounting software in the same way a taxpayer would.

IRS Letter 6174

“We have information that you have or had one or more accounts containing virtual currency but may not know the requirements for reporting transactions involving virtual currency, which include cryptocurrency and non-crypto virtual currencies. After reviewing the (educational) information below, if you believe you didn’t accurately report your virtual currency transactions on a federal income tax return, you should file amended returns or delinquent returns if you didn’t file a return for one or more taxable years.”

The key phrase is that the taxpayer “may not know” crypto tax treatment. It sounds like the IRS does not have sufficient information indicating unreported income. Letter 6174 is an “educational letter,” and it states, “you do not need to respond to this letter.” If you received this tax notice, then you should review your crypto tax reporting and consider filing an amended tax return, if appropriate. Consider the IRS advice a warning shot across your bow.

Letter 6174-A

“We have information that you have or had one or more accounts containing virtual currency but may not have properly reported your transactions involving virtual currency, which include cryptocurrency and non-crypto virtual currencies. After reviewing the information below, if you believe you didn’t accurately report your virtual currency transactions on a federal income tax return, you should file amended returns or delinquent returns if you didn’t file a return for one or more taxable years. You do not need to respond to this letter.”

The critical phrase is “may not have properly reported.” That’s different from Letter 6173, which states “may not have met” your tax requirements. Letter 6174-A implies the taxpayer reported crypto transactions, but perhaps not in the proper way. For example, maybe the taxpayer used Schedule C (business income) instead of Form 8949 (capital gains). Perhaps they used like-kind exchanges, and the IRS might not allow that. Conversely, Letter 6173 indicates the taxpayer did not report crypto transactions at all.

The IRS has various types of tax information for virtual currency account owners, and it selected the letter that best matched their knowledge base. The IRS is also using third-party services to obtain more tax information. It’s wise to come clean now if you know you have errors in reporting crypto transactions. Historically, taxpayers have performed better in seeking abatement of penalties if they come forward to the IRS before getting busted first.

Civil and criminal prosecution and FBAR reporting
The IRS stressed, “Taxpayers who do not properly report the income tax consequences of virtual currency transactions are, when appropriate, liable for tax, penalties, and interest. In some cases, taxpayers could be subject to criminal prosecution.” The IRS sent mob boss Al Capone to prison for tax evasion, which was less challenging than indicting him for unlawful bootlegging. Learn about accuracy-related penalties and what constitutes reasonable cause for reduction of penalties.

The IRS Virtual Currency Compliance campaign reminds me of IRS initiatives to hunt down hidden offshore bank and brokerage accounts. FATCA legislation forced foreign banks into reporting on U.S. resident accounts. The IRS Offshore Voluntary Disclosure Program (OVDP) helped taxpayers come clean with voluntary reporting. That led to reduced penalties, which otherwise were onerous. Some tax cheats used foreign bank accounts to conceal business income from the IRS. Others protected assets with offshore structures and only did not correctly report portfolio income.

In retrospect, it seems the IRS made a mistake in (unofficially) waiving foreign bank account report FinCEN 114 and Form 8938 for offshore virtual currency accounts. Virtual currency is “property,” which did not meet the requirements for FinCEN 114 and Form 8938 (Statement of Specified Foreign Financial Assets). There are significant penalties for not filing FinCEN 114 (previously known as FBAR) on time with the U.S. Treasury. Once you put Treasury on notice of owning these accounts, it dissuades you from hiding income from the IRS on those same accounts.

Coin-to-coin exchanges
In the educational section of these IRS letters, it states that crypto-to-crypto trades (i.e., Bitcoin for Ether) are taxable capital gains. The letter does not mention Section 1031 or like-kind exchanges being allowed on pre-2018 trades. (The new tax law TCJA restricted like-kind exchanges to real property only, starting in 2018.) Many crypto traders did not report deferred capital gains on coin-to-coin trades. Some may have, but they omitted the required Form 8824.

I’ve questioned whether coin-to-coin trades qualify for like-kind exchange treatment in years before 2018. Different types of virtual currencies might not be eligible as like-kind property, and coin exchanges are not qualified intermediaries. Multi-party like-kind exchanges require both.

Tax information statements and trade accounting
The IRS letters say to report all transactions whether tax information statements (Form 1099) were sent, or not, for crypto accounts held in the U.S., or abroad. Cryptocurrencies are “property,” not a “security,” so it’s not a “covered security” for purposes of 1099-B reporting. Coinbase, the largest U.S. crypto exchange, appeased the IRS during their fight for obtaining taxpayer information, by issuing a Form 1099-K for larger accounts. The IRS intended Form 1099-K for third-party network transactions for merchants; not traders or investors. Only U.S. exchanges might provide 1099-Ks. Coinbase also provided capital gain and loss reports for later years.

Taxpayers should consider using a trade accounting solution or software program to download virtual currency transactions from all coin exchanges and private wallets. Many crypto owners have accounts around the world, and accounting issues are more challenging when trading on margin. The IRS will likely use this same software in an exam.

Additional IRS guidance coming soon
The IRS keeps promising to publish further advice on crypto tax treatment soon. Why did they send 10,000 education letters if they plan to update their education guidance shortly? Perhaps, it would have been better to publish updated guidance before mailing them. This letter campaign seems a bit like a fishing expedition: The IRS wants more tax returns to analyze before it tackles tax treatment issues further.

Additional guidance is expected to address like-kind exchanges; chain splits, permissible accounting methods, wash sales, Section 475, and more. The AICPA issued a letter containing suggested questions and answers. The basics are clear, and the delay in additional guidance is no excuse for non-compliance.

IRS data analytics
The IRS said it would continue to use data analytics, and perhaps other blockchain technology to uncover more non-compliant crypto taxpayers. The IRS successfully used an independent company Chainalysis on recovering tax information from U.S. Coinbase customers. That may have been one of the sources for this first batch of 10,000 account letters.

What tax evaders didn’t initially realize is that virtual currencies may not be an ideal medium of exchange for concealing income and assets from tax authorities. Unlike using cash (dollar bills), blockchain is a distributed ledger which is available to the public. Non-crypto virtual currency may have a private company centralized ledger, but the IRS might be able to get that through a summons, too. AI, blockchain tools, and crypto trade accounting programs will help the IRS bust crypto tax evaders and taxpayers who are honest but misinformed.

Takeaway
This IRS letter campaign is just the beginning of virtual currency enforcement activities to come. You should take this opportunity to get fully educated, review your reporting, and be sure you are tax compliant. Pay tax liabilities and interest expenses, and then seek abatement of penalties when assessed. Some crypto users might try to claim ignorance or argue they received terrible tax advice. Others might assert that the crypto tax rules were too vague and uncertain at the time of filing. Some tax treatment issues are unknown (i.e., like-kind exchanges and hard forks), but the basics are clear. After receiving these education letters, which are warning shots, there are no grounds for continued non-compliance.

Consult a crypto tax expert immediately after receiving any of the above IRS letters. The CPA can reply to Letter 6173 soon and request more time to file amended returns. The 2018 tax return deadlines are coming up on September 15, 2019, for entities, and October 15 for individuals. Plan to work with your CPA after those dates on amended tax return filings.

Breaking news and more resources

IRS IR-2019-132: IRS has begun sending letters to virtual currency owners advising them to pay back taxes, file amended returns; part of agency’s larger efforts. 

WSJ quotes my partner in IRS Sending Warning Letters to More Than 10,000 Cryptocurrency Holders. “When it comes to preparing tax returns involving cryptocurrencies, Darren Neuschwander, a certified public accountant, said many tax preparers are frustrated because the IRS has long promised new guidance on cryptocurrencies that it hasn’t yet released.” “It’s ironic that the IRS is issuing these letters because we’re still waiting to know more rules,” he said.

IRS Sends Out 10,000 Letters to Virtual Currency Investors, Some of Which Demand a Response, By Ed Zollars CPA for Kaplan Financial Education.

Blockchain Analytics Firm Chainalysis Outlines User Data Policy Amid Coinbase Allegations in CoinTelegraph.

The IRS Has Special Software to Find Bitcoin Tax Cheats. Fortune.com

GreenTraderTax cryptocurrency resources:
Tax Center
Blog posts on cryptocurrencies
Green’s 2019 Trader Tax Guide
Trade accounting service for cryptocurrencies

Darren Neuschwander CPA contributed to this blog post.

 


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