Tag Archives: tax planning

CARES Act Allows 5-Year NOL Carrybacks For Immediate Tax Refunds

March 28, 2020 | By: Robert A. Green, CPA | Read it on

Live Updates:

March 28: On March 27, 2020, President Trump signed into law the Coronavirus Aid, Relief, and Economic Security (CARES) Act. This bill includes significant economic aid and tax relief provisions. Some tax relief applies retroactively to 2018, 2019, and 2020. Today, I focus on NOL carrybacks.

If you have a net operating loss (NOL) from business activities in 2018, 2019, and 2020, you should consider filing NOL carryback claims going back five years. 

Active traders who are eligible for trader tax status (TTS) are considered businesses with NOLs. A TTS trader might have significant trading expenses or Section 475 ordinary losses comprising an NOL. 

CARES temporarily suspends tax-loss limitations from the Tax Cuts and Jobs Act (TCJA) for 2018, 2019, and 2020. TCJA had repealed two-year NOL carrybacks, only allowing NOL carryforwards limited to 80% of the subsequent year’s taxable income. As you may remember, TCJA introduced the excess business loss (EBL) limitation, where aggregate business losses over an EBL threshold ($500,000 for married and $250,000 for other taxpayers for 2018) were considered an NOL carryforward. 

CARES lifts these TCJA limitations and allows taxpayers to recalculate 2018 and 2019 NOLs and file refund claims going back five years for immediate tax relief. Taxpayers will be able to carryback 2020 NOLs five years, too, but not until they file 2020 tax returns in 2021. 

TTS traders with Section 475 ordinary losses and those without 475 but who have significant NOLs from expenses (i.e., borrow fees on short-selling) should consider NOL carrybacks, too. 

Here’s an example

Joe Smith, a TTS trader with Section 475, filed a 2018 income tax return showing a $400,000 NOL. Joe’s NOL came from trading expenses ($50,000) and Section 475 trading losses ($350,000); he had no other income or loss.

Under TCJA, Joe’s only option is an NOL carryforward; therefore, his draft 2019 tax return has a low income, utilizing a small portion of his NOL. Joe has more trading losses and expenses YTD for 2020, so he is holding a deferred tax asset. Joe is thrilled that CARES opens the door to NOL carrybacks because he had substantial taxable income from other activities in years previous to 2018. 

We await IRS and state guidance on CARES to indicate precisely how Joe and his tax preparer should proceed with NOL recalculation and carryback returns. We have questions:

  1. Must taxpayers with EBL limitations amend 2018 tax returns to remove EBL and recalculate NOLs? Is CARES retroactive application to 2018 and 2019 an optional or mandatory requirement? Some taxpayers might prefer to leave things the way they are under TCJA.
  2. CARES allows taxpayers to carryback NOLs from 2018, 2019, and 2020 five years. Usually, tax years close after three years, so how will this work for 2018 NOL five-year carrybacks? For example, 2016 income tax returns filed by April 15, 2017, might close three years after by April 15, 2020. Is that postponed to July 15, 2020, with the IRS relief? Can a taxpayer go back five years before 2018? 
  3. The usual tax deadline for filing a 2018 Form 1045 (Application for Tentative Refund) for NOL carrybacks was Dec. 31, 2019. Will this deadline be extended? (We prefer using this form since the IRS must address the form within 90 days.) Alternatively, taxpayers may use Form 1040X (Amended U.S. Individual Income Tax Return) for each NOL carryback year, which often takes the IRS six months or more to address and pay the refunds. Will the form be expedited during this unprecedented time? There are other procedural questions beyond the scope of this blog post.
  4. Which states will conform with CARES on these tax changes, especially NOL carryback refund claims? During the Great Recession of 2008 and 2009, stimulus tax legislation allowed generous NOL carrybacks. However, some states decoupled from federal law on those changes. For example, California did not allow NOL carrybacks at all, and it restricted NOL carryforwards in several ways. 

Stay tuned to our blog post as we seek answers to these questions. I plan to cover other CARES tax changes that affect TTS traders, too. 

March 27: Congress and President Trump enacted into law the Coronavirus Aid, Relief, and Economic Security (CARES) Act. This “virus bill” includes significant economic aide and tax provisions to help all taxpayers. The House did not make any changes to the Senate version.

March 25: Senate Passes Updated Economic Relief Plan (CARES Act) for Individuals and Businesses (Tax Foundation). The final version of the law includes the tax-loss provisions covered in the March 20 update below. Here are the code sections from Thomson Reuters CheckPoint:

  • “NOLs arising in a tax year beginning after December 31, 2018 and before January 1, 2021 can be carried back to each of the five tax years preceding the tax year of such loss. (Code Sec. 172(b)(1) as amended by Act Sec. 2303(b)(1))
  • temporarily removes the taxable income limitation to allow an NOL to fully offset income. (Code Sec. 172(a), as amended by Act Sec. 2303(a)(1))
  • temporarily modifies the loss limitation for noncorporate taxpayers so they can deduct excess business losses arising in 2018, 2019, and 2020. (Code Sec. 461(l)(1), as amended by Act Sec. 2304(a))
  • temporarily and retroactively increases the limitation on the deductibility of interest expense under Code Sec. 163(j)(1) from 30% to 50% for tax years beginning in 2019 and 2020. (Code Sec. 163(j)(10)(A)(i) as amended by Act Sec. 2306(a)).” (See special rules for partnerships.)

March 20: Congress should proceed with new legislation like the Coronavirus Aid, Relief, and Economic Security Act, to provide additional tax relief, beyond the Treasury Department moving the April 15 tax deadline to July 15, 2020.

Senate Majority Leader Mitch McConnell’s CARES Act bill temporarily suspends the Tax Cuts and Jobs Act (TCJA) business loss limitations, including reauthorizing NOL five-year carrybacks, repealing the excess business loss (EBL) limitation, and loosening the business interest expense limitation. That’s fantastic news, as businesses need tax relief for losses ASAP. Here are the related CARES Act provisions:

  • 2203: Section 172(b)(1) – “Net operating loss carrybacks and carryovers” – Special Rule for losses arising in 2018, 2019, and 2020, such loss shall be a net operating loss carryback to each of the five taxable years preceding the taxable year of such loss.
  • 2203: Temporary repeal of 80% income limitation to deduct a 2018 and forward NOL for year beginning before 2021.
  • 2204: Repeal of 461(l) for 2018, 2019 and 2020 – excess business losses.
  • 2206: 163(j) special rules for 2019 and 2020, increasing ATI percentage from 30% to 50% for limitation on business interest.

CPA industry groups are also asking Congress to raise the $3,000 capital loss limitation, which was never indexed for inflation.

Treasury Secretary Steven Mnuchin announced President Trump’s directive to move the April 15 tax deadline to July 15, 2020, thereby postponing tax filings and tax payments for all taxpayers. Mnuchin said the extension would give “all taxpayers and business this additional time” to file returns and make tax payments “without interest or penalties.” I expect Treasury and the IRS will issue specific guidance soon. Hopefully, all states will follow suit with this federal change, so taxpayers don’t face conflicting rules.

Traders and 475 elections: Although it’s not guaranteed, I think the IRS might accept a 2020 Section 475 election submitted by July 15, 2020, since that is the new tax filing date. It would afford traders 90 days of additional hindsight. IRS FAQs might not address elections, although the CARES Act includes moving of election deadlines, too. If you have a massive Q1 2020 trading loss as a TTS trader, and you are counting on an NOL carryforward, or carryback if allowed, then it might be wise to file an extension by April 15, 2020, and attach a 2020 Section 475 election statement. I think you should be able to revise the election by July 15, 2020, if warranted. (See Massive Market Losses? Elect 475 For Enormous Tax Savings.)

March 19: Senator John Thune introduced a two-page bill Tax Filing Relief for America Act “To extend the due date for the return and payment of Federal income taxes to July 15, 2020, for taxable year 2019.” Treasury and the IRS recently issued guidance to delay certain tax payments for 90 days until July 15, 2020. Still, Treasury did not postpone the April 15 tax filing deadline, putting an undue burden on taxpayers and accountants. Thune’s legislation syncs tax filings with tax payments in a simple manner, whereas Treasury’s guidance is causing tremendous confusion. Senate Majority Leader Mitch McConnell introduced the Coronavirus Aid, Relief, and Economic Security Act, which incorporates Thune’s bill. Thanks to the AICPA for pushing Congress and Treasury hard to get this critical April 15 tax relief. Why rush an April 15 tax filing, exposing clients and accountants to coronavirus, if Treasury already postponed tax payments? See the AICPA Coronavirus Resource Center.

For prior updates, see Updated: April 15 Tax Deadline Moved To July 15.

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



Tax Planning At Year-End Generates The Most Savings

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

Join Robert A. Green, CPA of GreenTraderTax.com, in his informational Webinar on year-end tax planning for traders, individuals, and entities. Don’t ignore 2019 taxes until tax-time in March and April. For investors seeking to reduce 2019 tax liabilities, they should consider various transactions and strategies before the year-end. That’s when it counts the most!

Webinar hosted and recording produced by Interactive Brokers. Everyone is welcome; you don’t have to be a client of IB.


Robert A. Green, CPA

Robert A. Green, CPA



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


Last-Minute Tax Tips For Traders

March 19, 2019 | By: Robert A. Green, CPA

Many traders are filing 2018 tax returns, extensions, and Section 475 elections close to the deadline of April 15, 2019. Join Robert A. Green, CPA of GreenTraderTax.com to discuss several good reasons to file an extension, and his blog post “Tax Extensions: 12 Tips To Save You Money.” Mr. Green will set aside 15 to 30 minutes dedicated to answering questions, so come prepared.

Webinar hosted and recording produced by Interactive Brokers. Everyone is welcome; you don’t have to be a client of IB.

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How to Qualify for Trader Tax Status and Save (TradeStation)

March 15, 2019 | By: Robert A. Green, CPA

On March 19, join Robert A. Green, CPA, of GreenTraderTax as he breaks down the advantages of filing with trader tax status (TTS). Among other benefits,

  • TTS traders may use business expense treatment on 2018 and 2019 tax returns. Learn how to qualify for TTS.
  • Learn how TTS traders use an S-Corp to unlock employee benefit deductions for health insurance and retirement plans.
  • TTS securities traders should consider a 2019 Section 475 election by April 15, 2019, for tax loss insurance: Exemption from capital loss limitations, and wash sale loss adjustments.
  • The qualified business income (QBI) deduction might apply to traders with 475 income, but it’s uncertain at this time.

Webinar hosted and recording produced by TradeStation. Everyone is welcome; you don’t have to be a client of TS.

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Get a 100% rebate from TS on your GNMTraderTax purchase.

How To Maximize Tax Deductions For Traders (Interactive Brokers)

February 20, 2019 | By: Robert A. Green, CPA

The Tax Cuts And Jobs Act (TCJA) regulations, tax forms, and instructions have some surprises and unintended consequences. In this Webinar, GreenTraderTax CPA Robert A. Green will discuss how to maximize tax deductions for traders.

- There are lingering questions about whether a trader is eligible for a “qualified business income” (QBI) deduction.
- Learn how to claim trader tax status (business expense treatment).
- Consider a 2019 Section 475 election for tax loss insurance.

Webinar hosted and recording produced by Interactive Brokers. Everyone is welcome; you don’t have to be a client of IB.



Tips For Traders On Preparing 2018 Tax Returns (Lightspeed)

February 6, 2019 | By: Robert A. Green, CPA

Lightspeed customers can learn about common errors and opportunities that active traders can make on tax returns.

If you traded actively in 2018, you should watch this webinar before preparing your 2018 tax returns. Join CPAs Robert A. Green, Darren L. Neuschwander, and Adam W. Manning from Green, Neuschwander & Manning, LLC.

There are several new and revised 2018 tax forms based on the implementation of the 2017 Tax Cuts and Jobs Act.

  • Learn how traders, eligible for trader tax status (TTS), maximize business, home office, and startup expenses using critical tax-reporting strategies.
  • Don’t solely rely on broker 1099-Bs: There might be opportunities to switch to lower 60/40 capital gains rates in Section 1256, use Section 475 ordinary loss treatment if elected on time, and report wash sale losses differently.
  • Make vital 2019 tax elections on time.
  • Learn common errors on tax returns for TTS traders, which can lead to an IRS or state exam.
  • Learn tips for filing extensions and paying taxes.

Webinar hosted and recording produced by Lightspeed. Everyone is welcome; you don’t have to be a client of Lightspeed.

lightspeed webinar-06-03-2019


IRS Confirms Section 475 Is Eligible For QBI Tax Deduction

January 21, 2019 | By: Robert A. Green, CPA | Read it on

Good news for traders: Section 199A final regs confirm QBI includes Section 475 ordinary income and loss.

On Jan. 18, 2019, the IRS issued final 199A regs for the 2017 Tax Cuts and Jobs Act (TCJA) 20% qualified business income (QBI) deduction. The final regs update the August 2018 proposed/reliance 199A regs and confirm that QBI includes Section 475 ordinary income/loss.

Based on our interpretation of TCJA and the proposed/reliance regs, we figured QBI included Section 475 ordinary income/loss, but it was uncertain. Our previous content stated that QBI “likely” included Section 475 ordinary income/loss. The final and proposed/reliance regs each state that QBI expressly excludes capital gains and losses, and also excludes Section 954 items of ordinary income, including forex Section 988 and notional principal contracts.

Making our case to the IRS
After noticing that the proposed/reliance regs were silent about Section 475 income/loss, I contacted one of the lawyers at the Office of Chief Counsel listed on the 199A proposed regs.

The attorney called me back after he saw my interview in Tax Notes, “Groups Urge IRS to Rethink 199A Business Income Rules.” I presented our firm’s rationale for including Section 475 ordinary income/loss in QBI for TTS traders and suggested he read and watch our content. The IRS attorney said my rationale sounded “plausible” in his opinion.

Excerpts from final regs
Final 199A regs, p. 55-56:

“Given the specific reference to section 1231 gain in the proposed regulations, other commenters requested guidance with respect to whether gain or loss under other provisions of the Code would be included in QBI. One commenter asked for clarification about whether real estate gain, which is taxed at a preferential rate, is included in QBI. Additionally, other commenters requested clarification regarding whether items treated as ordinary income, such as gain under sections 475, 1245, and 1250, are included in QBI.

To avoid any unintended inferences, the final regulations remove the specific reference to section 1231 and provide that any item of short-term capital gain, short-term capital loss, long-term capital gain, or long-term capital loss, including any item treated as one of such items under any other provision of the Code, is not taken into account as a qualified item of income, gain, deduction, or loss. To the extent an item is not treated as an item of capital gain or capital loss under any other provision of the Code, it is taken into account as a qualified item of income, gain, deduction, or loss unless otherwise excluded by section 199A or these regulations.

Similarly, another commenter requested clarification regarding whether income from foreign currencies and notional principal contracts are excluded from QBI if they are ordinary income. Section 199A(c)(3)(B)(iv) and §1.199A-3(b)(3)(D) provide that any item of gain or loss described in section 954(c)(1)(C) (transactions in commodities) or section 954(c)(1)(D) (excess foreign currency gains) is not included as a qualified item of income, gain, deduction, or loss. Section 199A(c)(3)(B)(v) and §1.199A-3(b)(3)(E) provide any item of income, gain, deduction, or loss described in section 954(c)(1)(F) (income from notional principal contracts) determined without regard to section 954(c)(1)(F)(ii) and other than items attributable to notional principal contracts entered into in transactions qualifying under section 1221(a)(7) is not included as a qualified item of income, gain, deduction, or loss. The statutory language does not provide for the ability to permit an exception to these rules based on the character of the income. Accordingly, income from foreign currencies and notional principal contracts described in the listed sections is excluded from QBI, regardless of whether it is ordinary income.”

Parsing the language in the final 199A regs
In the proposed 199A regs, QBI excluded all capital gains and losses, and ordinary income/loss items expressly listed in Section 954. Section 954 does not include Section 475 ordinary income/loss. In the proposed regs, QBI expressly included Section 1231 losses from the sale of business property, whereas, QBI excluded Section 1231 capital gains. Section 475 ordinary income/loss is similar to Section 1231 ordinary losses, and it’s not in Section 954, so we determined that QBI likely included Section 475 ordinary income/loss.

The final 199A regs acknowledge the uncertainty and tax writers fixed it in the above language. They opened the door for Section 1231 losses to include more items like Section 475 ordinary income/loss, reiterating that it must not be on the Section 954 list, which Section 475 is not.

There’s an important caveat
Section 199A interacts with a modified Section 864(c), and Section 864 might deny QBI treatment to TTS traders and hedge funds. On the one hand, there is a rationale for QBI treatment for TTS traders, as expressed in this blog post, and Section 864 conflicts with that case. There are unresolved questions which I expect to write a blog post about it soon. Considering conflicts with Section 864, I think QBI treatment for traders is uncertain at this time.

How QBI might work for a TTS trading business
The proposed and final 199A regs state that traders eligible for trader tax status are a “specified service trade or business” (SSTB), so the SSTB taxable income (TI) cap applies. Taxpayers who make one dollar over the TI cap will not be allowed a QBI deduction on SSTB QBI. On the other hand, non-SSTB activity is not restricted to the TI cap, although the W-2 wage and property limitations apply over the TI threshold.

For 2018, the SSTB TI cap is $415,000/$207,500 (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 an SSTB. The 50% W-2 wage and property basis limitations also apply within the phase-out range. For 2018, the TI threshold is $315,000/$157,500 (married/other taxpayers): If a taxpayer is below the TI threshold, there are no phase-out, wage or property limitations for SSTB and non-SSTB.

For 2019, the SSTB TI cap increases to $421,400/$210,700 (married/other taxpayers) based on the inflation adjustment. The phase-out range remains the same, so for 2019, the TI threshold is $321,400/$160,700 (married/other taxpayers).

Hedge funds with TTS and Section 475 ordinary income/loss should report QBI, too. Investors in these hedge funds are eligible for a QBI deduction if they are under the TI cap. Even without a 475 election, trading SSTB has QBI losses from trading expenses.

Investment managers are also SSTB, and they have QBI from advisory fees. Carried interest as a profit allocation of Section 475 ordinary income/loss is QBI, too. Carried interest in capital gains is not.

It’s more crucial to qualify for TTS than ever before
TTS allows business expense treatment, whereas, TCJA suspended “certain miscellaneous itemized deductions subject to the 2% floor,” which includes investment fees and investment expenses. TCJA still allows investors itemized deductions for investment-interest expenses limited to investment income, and stock borrow fees as other itemized deductions. TTS business expenses allow a long list of deductions from gross income, including home office, and that’s far better!

TTS traders may elect Section 475 mark-to-market (MTM) accounting on securities and or commodities (Section 1256 contracts). Securities traders appreciate that Section 475 trades are exempt from dreaded wash-sale loss adjustments and the $3,000 capital loss limitation. I call it “tax loss insurance,” because 475 ordinary losses lead to much faster tax refunds. (TCJA did repeal NOL carrybacks, forcing NOL carryforwards, instead.) TTS traders are entitled to segregate investment positions to achieve lower tax rates on long-term capital gains. TTS traders prefer to skip Section 475 on commodities to retain lower 60/40 capital gains rates on Section 1256 contracts.

Now with final 199A regs, there’s still uncertainty for QBI treatment for TTS traders. Profitable TTS traders might want to consider a Section 475 election to be perhaps eligible for a potential QBI deduction. In some years, the trader might be under the TI cap, allowing a QBI deduction, and in other years, he might have a (good) problem of exceeding the cap for no QBI deduction.

Married taxpayers should consider filing separately, as that might unlock a QBI deduction for one spouse since the other spouse might have income exceeding the SSA income cap. TCJA equalized the tax rates for filing jointly vs. separately.

TTS traders with Section 475 ordinary losses might be unhappy. For example, assume a trader has $100,000 of QBI from a consulting business. She also has TTS/Section 475 ordinary losses of $40,000, so her aggregate QBI is $60,000, which reduces the QBI deduction.

Section 199A regs are complicated
There are complex issues over what constitutes an SSTB vs. non-SSTB, how to calculate the W-2 wage and property limitations, definitions of QBI, and more.

Taxpayers have to calculate the QBI deduction on whichever is lower: aggregate QBI or taxable income minus net capital gains/losses.

If you expect to receive a 2018 Schedule K-1 containing QBI tax information, then consider filing an automatic extension by April 15. I assume that many pass-through entities won’t issue final 2018 Schedule K-1s until after that date. It’s great that the IRS issued the final 199A regs now, but there are still conflicts and unresolved questions. Look for QBI items on partnership Schedule K-1 line 20 “Other Information” marked with various codes for 199A items of income, wages, property and more. See the K-1 instructions for line 20.

Elect Section 475 on time
Individual TTS traders need to file a 2019 Section 475 election statement with the IRS by April 15, 2019. Existing partnerships and S-Corps need to file a 2019 Section 475 election statement with the IRS by March 15, 2019. New taxpayers (i.e., new entities) may elect Section 475 within 75 days of inception by internal election. Existing taxpayers have a second step to file a Form 3115 with their 2019 tax return.

Learn more about TTS, Section 475, QBI and entity solutions in Green’s 2019 Trader Tax Guide.

Darren L. Neuschwander, CPA contributed to this blog post.

I revised this blog post on March 5, 2019, in conjunction with my new blog post Uncertainty About Using QBI Tax Treatment For Traders

Traders Have Unique Benefits For This Tax Season (Interactive Brokers)

January 17, 2019 | By: Robert A. Green, CPA

Tax season is underway, and TV commercials from tax software companies are stressing the need for CPAs on-demand. This is probably because 2018 is the first year of changes from the 2017 Tax Cuts and Jobs Act (TCJA). Join Robert A. Green, CPA of GreenTraderTax to review highlights from Green’s 2019 Trader Tax Guide.

- Business traders fare better.
- Can traders deduct trading losses?
- Tax treatment on financial products.
- Entities for traders.
- Retirement plans for traders.
- Tax Cuts and Jobs Act impact on traders.
- 20% deduction on qualified business income.
- Investment management carried interest.

Webinar hosted and recording produced by Interactive Brokers. Everyone is welcome; you don’t have to be a client of IB.