August 2013

Tax court was right to deny Endicott TTS

August 30, 2013 | By: Robert A. Green, CPA

We agree with the IRS and tax court on denying trader tax status (TTS) — otherwise known as business treatment — to Endicott (TC Memo 2013-199, Aug. 28, 2013) for 2006 and 2007 since he clearly was a long-term stock investor managing risk in his long portfolio with call options held on average one to five months and a number of stock positions held for over a year, with some over four years.

Many investors use options in this manner. They hold significant long positions in stock and are exposed to bearish headlines, so during “risk off” periods they may sell calls or buy puts on their underlying stock. When they expect little movement they may “write premium” to enhance their income.

Management of an investment portfolio is a far cry from being a business trader with an entity, day and swing trading weekly and monthly options full-time with executions almost every day of the week, average holding periods of less than seven days, and no connection to management of risk in an investment portfolio.

Endicott failed all our golden rules for TTS qualification in 2006 and 2007. Our rules call for 500 round trip trades and Endicott had 204 trades in 2006 on 75 days and 303 trades on 99 days in 2007. Our rules call for executions on 75% of available trading days and Endicott had well under 40%. Additionally, there were seven months in 2006 in which he executed less than three trades in a given month.

Endicott was even less frequent than Holsinger, another landmark trader tax court case we covered on our blog dated 9/3/08. Holsinger executed 372 options trades on 45% of trading days. Holsinger was at least trading and not managing his investments like Endicott.

We have some questions about Endicott’s 2008 trading activity since his numbers —1,543 trades on 112 days, including investments — exceeded our 500 round trip requirement. But, he still was stuck at 45% of day executions, well below our 75% requirement. He started trading ETFs instead of options in 2008, perhaps in connection with his portfolio of investments, although we don’t know for sure. The court clearly focused on the big picture over three years (2006 to 2008) and couldn’t get past the fact that Endicott was a significant investor managing his portfolio and was not running a separate and distinct trading business.

Endicott begged for a beat down from the IRS. He deducted $300,000 on a trading business Schedule C, including huge margin interest on his long stock investment portfolio. Investors deduct investment interest expense on Schedule A (itemized deductions) and it’s limited to investment income.

There are some interesting precedents that come out of the Endicott court.

We’ve written about presenting the “hotel analogy” for options traders to the IRS and this ruling seems to deny one pillar of that argument. Although we would have presented the argument better, Endicott did not deserve to make this case. It’s only for a very close call on TTS.

Endicott argued his number of trading days should include days his option investments were actually open — not just the execution days for buys and sells. He said he did not trade options on a daily basis because commissions made it unprofitable. That’s bogus. Option traders can trade enough to surpass our golden rules if they are running a business. The court agreed and said counting days that investments are open doesn’t hold muster for counting trading days. We don’t consider this a denial of our hotel analogy, but it’s certainly a shot across the bow on that argument.

There are some interesting technicalities in the Endicott ruling. The court broke down qualification for TTS into two sub-part tests, although we think they are basically one test. The first test was “substantial” for size and number of trades. The court erred in viewing Endicott’s significant stock portfolio as part of the TTS test, as although it was large, it doesn’t count in a TTS analysis.

The second test was for “frequency” and it focused on trading execution days as a percentage of available trading days. Endicott knew he came up far short and he tried to claim days for options being open.

We agree with the tax court that Endicott was not attempting to catch the swings in the daily market because his overall holding period of the call options. Holding periods of one to five months are definitely not, as the tax court implies, “indicative” for a trader seeking such swings in the daily market.

(Note: Upon our complete reading of the Endicott case, we found a footnote by the tax court of what is deemed as an “executed trade.” The tax court appears to take the position that the expiration of an option in itself does not count within a trader’s number of “executed trade” for TTS qualification due to lack of any required action of the trader himself. The following example was given: If a taxpayer “purchased stock, sold a call option that expired unexercised, and subsequently sold the stock,” only three trades were deemed executed. This is contrary to our position that the expiration of an option is a trade itself.)

The lesson in the Endicott court case is it’s very important to ring fence investments vs. business trading. If you have material investments, it’s wise to use a trading business entity for that separation. When trader tax status is analyzed, don’t let investments infect your analysis. Don’t count investments in the numerator or denominator for the percentage of days traded, number of trades or average holding period.

Had Endicott had a consultation with our firm in the years in question, we would have certainly told him he did not qualify for TTS. As we have said for several years, it’s more challenging for an options trader to qualify for TTS. Especially when they have a full-time job and trade monthly options on the side a few days per week, bunching trades around explorations.

There is plenty of good news in the Endicott court ruling, too. It affirms TTS and reinforces what does qualify.

What should options traders do to qualify for TTS? 
We advise setting up a separate trading business entity that disconnects trading from an individual’s investment portfolio. Don’t manage your investments with options and other “risk on and risk off” instruments like ETFs and indexes. Rather, day and swing trade options, ETFs and indexes on a stand-alone business-trading-program basis. Make sure you meet our golden rules.

Side note: The Edicott Court raised a concern about Endicott’s other Schedule C for consulting income. Endicott retired in 2002 and received income on a yearly basis as part of a non-compete agreement as the president of his former company. He reported this income on a separate “Consulting” Schedule C for each respective tax year. There appears to be no actual daily work requirement for Endicott in association with the receipt of this income and therefore it had no interference on his attempt to trade. The tax court pointed out that a taxpayer that qualifies for TTS “generally” should have the business of trading as his/her “sole or primary source of income.” The key term is “generally.” Just because a taxpayer has another source of income and net trading losses in a given tax year does not in itself deny a taxpayer from qualifying as TTS. In Endicott’s case, this other income was for past services and it should not have been a contributing reason for denial of TTS. 

Watch our Sept. 10, 2013 Webinar recording on this subject.


Same-sex marriages will be recognized for tax purposes

August 29, 2013 | By: Robert A. Green, CPA

If you are same-sex married, you need to learn about new IRS and state tax rules that affect your tax filings, including possibly having to amend open year tax returns. We ask our clients affected to contact us to discuss it soon.

Aug. 30 update: The IRS has released FAQs clarifying the Revenue Ruling. The FAQs make it clear that same-sex married couples must file extended 2012 returns by Sept. 15, 2013, to file as single. The application of yesterday’s Revenue Ruling depends on the tax year in question:
• For tax year 2012 and all prior years, same-sex spouses who file an original tax return on or after Sept. 16, 2013 (the effective date of Rev. Rul. 2013-17), generally must file using a married filing separately or jointly filing status;
• For tax year 2012, same-sex spouses who filed their tax return before Sept. 16, 2013, may choose (but are not required) to amend their federal tax returns to file using married filing separate or joint filing status;
• For tax years 2011 and earlier, same-sex spouses who filed their tax returns timely may choose (but are not required) to amend their federal tax returns to file using married filing separate or joint filing status provided the period of limitations for amending the return has not expired; and
• For tax year 2013 and going forward, same-sex spouses generally must file using a married filing separate or joint filing status.

For more details, see the IRS release: All Legal Same-Sex Marriages Will Be Recognized for Federal Tax Purposes.


Contributing to multiple retirement plans

August 23, 2013 | By: Robert A. Green, CPA

Please read this update from the IRS because we get this question from clients several times a year.

In the latest edition of Retirement News for Employers, the IRS reviews the amount of contributions and salary deferrals that can be made by an individual eligible for participation in multiple retirement plans. The types of plans that must be aggregated in calculating the individual limit for a calendar year are provided, as well as how to handle contributions made in excess of the annual limit. Examples are included that demonstrate the interaction of catch-up contributions (available to individuals age 50 or older by year-end) with the annual limits.


Common trader tax mistakes

August 18, 2013 | By: Robert A. Green, CPA

Trader tax laws and benefits are complex and nuanced. Far too many traders and tax preparers don’t know the laws or misapply them on tax returns. Why pay tens of thousands of tax dollars more than you should?

It’s wise to educate yourself before risking your capital and it’s wise to do the same before planning and filing tax returns. To help with the latter, I’ve assembled a list of the most common mistakes made by traders and tax preparers.

Big picture items

1. Not claiming trader tax status, business expense treatment. (Or claiming this status when not entitled to it.) Business traders can save an average of $5,000 or more using business expense treatment. Business expenses are 100% deductible from gross income, whereas investment expenses are considered miscellaneous itemized deductions and are only deductible “below the line” in excess of 2% of adjusted gross income (AGI) and added back for the Alternative Minimum Tax (AMT), also known as the nasty second tax regime. Business expenses allow home-office deductions, education expenses, and startup costs, whereas investment expenses do not. Also, traders may claim trader tax status after the fact, including on amended tax return filings for the past three open tax years.

2. Not filing the Section 475 MTM ordinary loss election on securities and getting stuck with the puny $3,000 capital loss limitation, wash sale loss headaches, and extra tax costs. Many traders and accountants mishandle the Section 475 election statement (due by April 15 of the current tax year for existing individuals and partnerships) or they botch perfecting the election on a Form 3115 filing. One mix up can jeopardize ordinary gain or loss treatment. The biggest pitfall for traders is not deducting trading losses when they otherwise could. Section 475 does not apply to segregated investments or Section 1256 contracts when elected on securities only.

Unfortunately, you can’t fix a missed or botched Section 475 election; you need to focus on climbing out of the capital loss carryover hole you dug. You can form a new entity and use the “new taxpayer” exception allowing an internal Section 475 election within 75 days of inception.

3. Making the wrong decision about the forex Section 988 opt-out election and reporting forex incorrectly. Spot and forward forex receives Section 988 ordinary gain or loss treatment (which generally is better than a capital loss limitation). At any time during the tax year, traders are entitled to file an internal “contemporaneous” opt-out election to have capital gains treatment instead. That’s helpful if you have capital loss carryovers. If you trade in major forex currencies and don’t “take or make delivery” of the underlying currency, the opt-out election subjects forex forwards — and we make a case for spot forex too — to the lower Section 1256(g) 60/40 tax rates. That reduces the highest tax rates by 12%!

Forex reporting depends on whether you file the Section 988 opt-out election and whether you qualify for trader tax status. Section 988 without trader tax status is line 21 of Form 1040, and with that status its Form 4797 Part II. Section 988 losses over $50,000 require “tax shelter” Form 8886. Many IRS agents are confused over tax treatment for spot forex, plus forex brokers aren’t supposed to issue 1099-Bs for spot forex. Make sure to read brokers’ tax reports correctly. For example, rollover interest is part of trading gain or loss. If you opt-out of Section 988 and choose Section 1256(g), use mark-to-market at year-end on Form 6781. Thankfully, summary reporting applies on forex.

4. Not forming a trading entity to unlock AGI deductions for retirement plans and health insurance premiums. These AGI deductions can save $2,000 to $17,000 or more in taxes, but sole proprietor retail traders can’t get them in connection with trading gains. By forming a simple pass-through entity like a partnership, LLC, or S-Corp, business traders can take advantage of these deductions.

Tax reporting errors and compliance headaches

5. Reporting trading gains and losses on Schedule C, almost guaranteeing an IRS notice or exam. Items must be reported in the correct place. While business expenses are reported on Schedule C, trading gains and losses are reported on other tax forms like 8949, 6781, and 4797.

6. Using our transfer-of-income strategy incorrectly, or not using it at all. The transfer is executed differently for sole proprietors vs. entities. You need this transfer to unlock the home-office deduction, Section 179 depreciation, and AGI deductions, and to reduce the IRS red flag factors on Schedule C and entities.

7. Using the wrong solution for securities trade accounting and calculating gains and losses incorrectly, especially wash sales. Many traders and preparers botch IRS cost-basis reporting on Form 8949 and the reconciliation with Form 1099-B. Some traders fail to report non-1099-B items like stock options on Form 8949. We recommend TradeLog software to handle this after downloading actual trades, rather than inputting 1099-B information.

8. Botching tax treatment between securities, Section 1256 contracts, forex, ETFs, options, precious metals, foreign futures, and more.

9. Misreporting Section 1256 contracts such as securities on Form 8949 rather than on Form 6781, thereby losing lower 60/40 treatment. Not all brokers report Section 1256 contracts correctly, especially instruments that aren’t clearly designated as such including some E-mini indexes and options on those indexes.

10. Misreporting ETFs and ETF options and not adding Schedule K-1 pass-through income to cost basis. ETFs and ETF options are generally taxed as securities, and commodity ETFs often pass through Section 1256 income or loss on a K-1. Options on commodity ETFs can be considered Section 1256 contracts. It’s a pain to deal with numerous ETF K-1s at tax time.

11. Not filing a 1099-Misc for fees paid to service providers, including you for administration. Sole proprietors or entities paying service providers $600 or more by check or cash must issue a Form 1099-Misc. It’s better to file a 1099-Misc. late subject to a penalty of $50 rather than encourage the IRS to catch you and assess much higher penalties.

12. Misreporting education expenses. Pre-business education expenses — including seminars, trade shows, and travel — are generally not allowed as investment expenses. Education is allowed as a business expense but only if incurred after qualifying for trader tax status. Try to squeeze a reasonable amount of pre-business education into Section 195 startup costs to expense once you achieve trader tax status. Don’t fall prey to those promising better results using dual entity schemes including a C-Corp.

13. Not filing a tax return due to negative income and trading losses. Expect a “jeopardy” (made up) tax assessment notice from the IRS. If you trade securities, the IRS doesn’t see the full picture, even with new cost-basis reporting. The IRS may think you made a lot of money and will hit you with a huge tax bill. Not filing can cause you to lose capital loss carryovers for previous years. With 1099s filed by brokers, there is no place to hide.

14. Mishandling tax notices and IRS exams. Generally, IRS and state agents don’t understand a trading business. It’s not a passive loss activity or hobby loss activity, and various items are reported in different areas with complex and nuanced tax treatment and elections. State tax rules for entities usually make exceptions for trading businesses, but that is not always apparent. Before a tax exam gets out of control, consult with a trader tax expert to get it on the right path.

15. Being non-compliant on FBAR and other foreign tax reporting such as Form 8938 (foreign financial assets). Congress and the IRS are very concerned about tax cheats using offshore bank accounts, structures, and schemes. Not filing foreign bank account reports (FBAR) on time or correctly can be costly: Back taxes, penalties, interest, and even criminal proceedings could be the result. Consider the IRS’s Offshore Voluntary Disclosure Initiative (OVDI). (Note that this program is NOT amnesty; in some cases, it’s a mistake to enter OVDI when there’s a better way to come clean.) Generally, opening offshore entities doesn’t help reduce taxes as they are treated as disregarded entities or they are subject to passive foreign investment company rules. Avoiding the Commodity Futures Trading Commission’s rules for retail forex trading by using offshore accounts or entities doesn’t work.

Entities and retirement plans

16. Forming the wrong type of entity, and in the wrong state. If you live, work, and trade in your home state and want to form a pass-through entity, it’s best to form it there. Don’t fall prey to promoters in Nevada harping on the benefits of corporations formed in Nevada. If you don’t register that Nevada entity in your home state, you won’t have asset protection in your home state. A Nevada LLC filing as a partnership passes through its income to your home state.

17. Tapping into IRA and other retirement funds incorrectly, causing IRS penalties and trouble. Don’t get busted by the IRS for misusing your retirement funds. See our blog dated Jul. 24, 2013 “Learn the DOs and DON’Ts of using IRAs and other retirement plans in trading activities and alternative investments” for more on this topic.

18. Triggering wash sale losses in IRAs which are permanently lost. Far too many traders make this tragic mistake. When you buy back a “substantially identical” security position in any of your IRAs 30 days before or after selling it for a loss in any of your taxable accounts, you can kiss that tax loss goodbye forever. It applies across husband and wife individual and joint accounts. Normally, wash sales are only a deferral problem, but in this case it’s a permanent problem. Abstain from trading substantially identical positions in your IRA accounts or house your active trading in an entity, which is a different taxpayer for purposes of the wash sale rules. A Section 475 election also solves this problem.

19. Choosing the wrong type of retirement plan. The Individual 401(k) plan for business traders is best. It combines a 100% deductible 401(k) elective deferral — where the biggest tax savings lies — with a 20% deductible profit-sharing plan. Don’t forget to open this plan before year-end, even with no money contributed.

20. Paying self-employment (SE) taxes on trading gains. Only full members of futures exchanges owe SE taxes on futures trading gains. Too many traders pay SE taxes on these gains and the IRS doesn’t challenge it. Watch out for the new ObamaCare 3.8% Medicare surtax on unearned income starting in 2013.

Bottom line
Common mistakes cost traders tens of thousands of dollars per year on their tax returns. Don’t be penny wise and pound foolish. Spend a few dollars to buy premium trader tax guides to learn how to avoid these mistakes. Consider engaging a trader tax expert to help with your tax return elections, planning, and preparation. Use the right trade accounting software for securities. Some mistakes you can fix on tax returns on extension or on amended tax return filings. Other mistakes can’t be fixed, and you should focus on tax strategies to dig out of that hole.


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