Tag Archives: tax compliance

2023 Tax Tips for Active Traders

February 22, 2024 | By: Robert A. Green, CPA

Slide presentation

Join Robert A. Green, CPA, from GreenTraderTax.com, for insights and information to help traders file their 2023 federal tax returns in a timely and accurate manner in 2024.

  • Mr. Green interviews Darren Neuschwander, CPA, head of tax compliance services for Green, Neuschwander & Manning, LLC. Mr. Neuschwander will discuss what’s new this year for traders.
  • Learn how traders, eligible for trader tax status (TTS), maximize business expenses, make vital tax elections, and utilize pass-through entities for further tax benefits, including health insurance, retirement plans, QBI, EBL, NOL, and SALT deductions.
  • Learn all the various tax treatments for multiple financial products, wash sales, and other accounting methods.
  • Learn tips for filing tax extensions and paying taxes on time to avoid penalties.
  • Learn common errors on TTS traders’ tax returns that lead to an IRS or state exam.

 

Tips For Traders On Preparing 2023 Tax Returns

January 24, 2024 | By: Robert A. Green, CPA

Presentation

Join Robert A. Green, CPA, from GreenTraderTax.com, for insights and information to help traders file their 2023 federal tax returns in a timely and accurate manner in 2024.

  • Mr. Green interviews Darren Neuschwander, CPA, head of tax compliance services for Green, Neuschwander & Manning, LLC. Mr. Neuschwander will discuss what’s new this year for traders.
  • Learn how traders, eligible for trader tax status (TTS), maximize business expenses, make vital tax elections, and utilize pass-through entities for further tax benefits, including health insurance, retirement plans, QBI, EBL, NOL, and SALT deductions.
  • Learn all the various tax treatments for multiple financial products, wash sales, and other accounting methods.
  • Learn tips for filing tax extensions and paying taxes on time to avoid penalties.
  • Learn common errors on TTS traders’ tax returns that lead to an IRS or state exam.

If you can’t join us live, register, and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

Significant Tax Moves For Traders To Make in Q1 2024

January 2, 2024 | By: Robert A. Green, CPA

Slide presentation

Join Robert A. Green, CPA, from GreenTraderTax.com, for insights and information to help traders.

  • Green will interview Darren Neuschwander, CPA, of Green, Neuschwander & Manning, LLC. Mr. Neuschwander will give tips on how to get organized early to improve tax season results.
  • Fourth quarter estimated taxes are due Jan. 16, 2024. Learn to avoid a 7 to 8% underestimated tax penalty.
  • Do not trigger 2023 wash sale losses by repurchasing losing trades in January 2024.
  • Focus on extensions due April 15, 2024, for individuals and March 15, 2024, for partnerships and S-Corps.
  • Learn how to assess qualification for trader tax status (TTS) in 2023 and 2024.
  • TTS traders should consider a Section 475 MTM election with a federal extension.
  • Focus on trade accounting for various tax treatments for securities, futures, options, ETFs, ETNs, and cryptocurrencies.
  • Learn how to read a broker-issued Form 1099-B.

If you can’t join us live, register, and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

Year-End Tax Planning For Traders

October 24, 2023 | By: Robert A. Green, CPA

Presentation Slides

Join Robert A. Green, CPA of GreenTraderTax.com, in his webinar on year-end tax planning for traders. Don’t wait until tax time in April 2024; arrange tax savings for 2023 before the year-end. Learn about tax-loss selling, avoiding wash sale losses, paying estimated taxes, and other tax-saving strategies.

Year-End Tax Planning For Traders

September 22, 2023 | By: Robert A. Green, CPA

Join Robert A. Green, CPA of GreenTraderTax.com, in his webinar on year-end tax planning for traders. Don’t wait until tax time in April; arrange tax savings before year-end. Learn about deferring income, accelerating deductions, tax-loss selling, avoiding wash sale losses, paying estimated taxes, Roth IRA conversions, S-Corp payroll with health and retirement benefits, SALT cap workaround strategies for pass-through entities, and other tax-savings strategies. Mr. Green will cover recent tax law changes that affect traders.

If you can’t join us live, register and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

How Traders Maximize Tax Benefits Q&A

June 21, 2023 | By: Robert A. Green, CPA

Join host Robert A. Green, CPA of GreenTraderTax.com. Panelists include Darren Neuschwander, CPA, and Adam Manning, CPA, Managing Members of Green, Neuschwander & Manning, LLC, a CPA firm focused on traders.

We’ll spend about 15 minutes on the below content and 45 minutes on Q&A.

Active traders who qualify for trader tax status (TTS) are entitled to significant tax benefits:

– TTS traders can deduct from gross income business expenses of all stripes.
– They can elect mark-to-market accounting (Section 475 MTM) to avoid wash sale losses on securities and navigate around the $3,000 capital loss limitation – tax loss insurance. They can be eligible for a 20% deduction on qualified business income (QBI) if profitable.
– Traders can arrange health insurance and retirement plan deductions (employee benefits) using an S-Corp to pay officer compensation, which creates the necessary earned income component.
– In about 29 states, TTS pass-through entities can utilize the state and local tax (SALT) cap workaround solution to avoid the $10,000 cap on SALT itemized deductions.
– Investors can’t arrange any of the above tax breaks but enjoy long-term capital gains rates and lower 60/40 capital gains rates on futures (1256 contracts).

About GreenTraderTax and Green, Neuschwander & Manning, LLC: https://greentradertax.com/about-us/

If you can’t join us live, register and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

Highlights From Green’s 2023 Trader Tax Guide

April 18, 2023 | By: Robert A. Green, CPA

Use Green’s 2023 Trader Tax Guide to receive the tax breaks you’re entitled to on your 2022 tax returns and execute tax strategies and elections for tax-year 2023. Our guide covers the impact of recent tax laws on traders.

BUSINESS TRADERS FARE BETTER

Investors have restricted investment interest expense deductions. The Tax Cuts & Jobs Act (TCJA) suspended investment fees and expenses for 2018 through 2025. Investors have a capital-loss limitation against ordinary income ($3,000 per year) and wash-sale (WS) loss adjustments, which can trigger capital gains taxes on phantom income. Investors benefit from lower long-term capital gains rates on positions held for 12 months or more before a sale (0%, 15%, and 20%). If traders have long-term investment positions, this is also available to them.

Traders eligible for trader tax status (TTS) are entitled to many tax advantages. A sole proprietor (individual) TTS trader deducts business expenses, startup costs, margin interest, and home-office expenses. TTS allows them to elect Section 475 MTM ordinary gain or loss treatment promptly. To deduct health insurance and retirement plan contributions, a TTS trader needs an S-Corp to create earned income with officer compensation. TTS traders use a pass-through entity (partnership or S-Corp) to arrange a state and local tax (SALT) cap workaround in many states.

TTS is different from the election of Section 475 MTM accounting. TTS is like an undergraduate university, and Section 475 is like graduate school. The 475 election converts new capital gains and losses into 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 WS loss adjustments. The 20% deduction on qualified business income (QBI) includes Section 475 ordinary income but excludes capital gains, interest, and dividend income.

A business trader can assess and claim TTS business expenses after year-end and even go back three open tax years. TTS does not require an election. But business traders may only use Section 475 MTM if they filed an election on time, either by April 18, for 2022 and 2023, or within 75 days of inception of a new taxpayer (i.e., a new entity). For more on TTS, see Chapter 1; for Section 475, see Chapter 2.

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 trading losses. Maybe they qualify for TTS, but that only gives them the right to take trading business expenses on Form 1040/Schedule C.

Securities, Section 1256 contracts, ETNs, and cryptocurrency trading receive default capital gain/loss treatment. Suppose a TTS trader did not file a Section 475 election on securities and commodities on time (i.e., by April 18, 2022) or have Section 475 from a prior year, they are stuck with capital loss treatment on securities and Section 1256 contracts. Section 475 does not apply to ETN prepaid forward contracts (not securities) or cryptocurrencies (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 carry over to the subsequent tax year(s).

Once taxpayers get in the capital loss carryover trap, they often face a problem: how to use up the capital loss carryover in the following year(s). If a taxpayer elects Section 475 by April 18, 2023, the 2023 TTS trading gains will be ordinary rather than capital, thereby not utilizing the capital loss carryover. Once a trader has a capital loss carryover hole, they need 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 they want capital gain/loss treatment again. Chapter 2 covers this topic in depth.

Traders with capital losses from Section 1256 contracts (such as futures) might be lucky 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 election allows taxpayers to offset their current-year net 1256 losses against prior-year net 1256 gains to receive a refund of taxes paid in prior years. TTS traders may elect Section 475 MTM on commodities, including Section 1256 contracts. Still, most elect it on securities only to 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. The other 40% fall under ordinary income rates.

Taxpayers with losses trading forex contracts in the off-exchange Interbank market may be in luck. Section 988 for forex transactions receives ordinary gain or loss treatment by default, which means the capital-loss limitation doesn’t apply. However, the forex loss isn’t considered a business loss without TTS. It can’t be included in a net operating loss (NOL) carryforward calculation — potentially making it a wasted loss since it also can’t be added to the capital-loss carryover. If the taxpayer has another source of taxable income, the ordinary loss offsets it; the concern is when there is negative taxable income.

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. However, Section 475 losses and TTS business expenses are subject to the excess business loss (EBL) limitation for tax years 2022 and 2023. Anything over the EBL threshold is a net operating loss (NOL) carryforward.

Those not using Section 475 must deal with wash-sale loss adjustments.

WASH-SALE LOSSES

Day and swing traders inevitably trigger many WS loss adjustments amounting to tens or hundreds of thousands of dollars. Create a WS loss when you take a loss on a security and repurchase it within 30 days (after or before).

A wash sale reduces the cost basis on the position sold and adds the WS loss to the replacement position’s cost basis, creating phantom taxable income and capital gains taxes.

It’s okay to incur WS losses during the year but try to avoid delaying the WS losses to the following year. Deferring a loss from November to December is acceptable; however, postponing a loss from December 2022 to January 2023 is not.

You can “break the WS chain” at year-end. For example, sell your entire position in security A by Dec. 20, 2022, and don’t repurchase it for 30 days — around Jan. 21, 2023. Waiting allows you to deduct the whole year of WS losses in 2022. See more about WS in Chapter 4.

EXCESS BUSINESS LOSS LIMITATION

In 2018, TCJA introduced an excess business loss (EBL) limitation. TCJA also repealed NOL carrybacks (except for farmers) and limited NOL carryforwards to 80% of the subsequent year’s taxable income. Add EBL over the threshold to the NOL carryforward.

The 2020 CARES Act suspended TCJA’s EBL, and NOL changes for 2018, 2019, and 2020 and allowed five-year NOL carrybacks (i.e., a 2020 NOL carryback to 2015). TCJA’s EBL and NOL carryforward rules apply for tax years 2021 through 2028.

See more about EBL and its thresholds in Chapter 2.

TAX TREATMENT ON FINANCIAL PRODUCTS

There are complexities in sorting through different tax-treatment rules and tax rates. It often takes work 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. Here’s a brief breakdown.

Securities have realized gain and loss treatment and are subject to WS rules and the $3,000 per year capital loss limitation on individual tax returns. Realization means income or loss when sold instead of mark-to-market (MTM) accounting. A Section 475 MTM election on securities avoids this issue.

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. Most TTS traders skip a Section 475 election on commodities to retain lower 60/40 capital gains rates.

Options have a wide range of tax treatments. 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 (stock index futures) are Section 1256 contracts. Simple and complex equity option trades have special tax rules on holding periods, adjustments, and more.

Forex receives ordinary gain or loss treatment on realized trades (including rollovers) unless a trader makes a contemporaneous capital gains election. In some cases, lower 60/40 capital gains tax rates on majors may apply under Section 1256(g).

Physical precious metals are collectibles; if a trader holds these capital assets for more than 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.

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, enhance a QBI deduction on Section 475 income less trading expenses, and provide a SALT cap workaround. 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 separation from individual investments.

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

A spousal-member LLC taxed as a partnership can segregate business trading from investments to perfect use of TTS and Section 475 and provide a SALT cap workaround, turning non-deductible state and local taxes as itemized deductions into tax-deductible business expenses. See Chapter 7.

RETIREMENT PLANS FOR TRADERS

TTS S-Corps can unlock a retirement plan deduction by paying sufficient officer compensation in December 2022 when results for the year are evident.

Consider a Solo 401(k) retirement plan with an elective deferral amount up to a maximum of $20,500 (or $27,000 if age 50 or older with the $6,500 catch-up provision). The Solo 401(k) also has a profit-sharing plan (PSP) up to a maximum of $40,500.

The IRS raised the 401(k) elective deferral for 2023 to $22,500 and the catch-up contribution to $7,500. See Chapter 8.

DEDUCTION ON QUALIFIED BUSINESS INCOME

In 2018, 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).

Because TTS traders are considered a “specified service trade or business” (SSTB), taxable income above the following thresholds is not deductible: $340,100/$170,050 (married/other taxpayers) for 2022 and $364,200/$182,100 (married/other taxpayers) for 2023.

There is also a phase-out range above the threshold of $100,000/$50,000 (married/other taxpayers). The W-2 wage and property basis limitations apply within the phase-out range. TTS traders with an S-Corp usually have wages, whereas sole proprietor traders do not.

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

For more information, see Chapter 7 and Chapter 17.

SALT CAP WORKAROUND

TCJA capped state and local income, sales, and property taxes (SALT) at $10,000 per year ($5,000 for married filing separately) and did not index it for inflation. About 29 states enacted SALT cap workaround laws.

Generally, elect to make a pass-through entity (PTE) payment on a partnership or S-Corp tax return filed by a business. It doesn’t work with a sole proprietorship filing a Schedule C. PTE is a business expense deduction shown on the state K-1 like a withholding credit. Most states credit the individual’s state income tax liability with the PTE amount. Essentially, convert a non-deductible SALT itemized deduction (over the cap) into a business expense deduction from gross income.

DESK REFERENCE

Some readers use our guide as a desk reference to quickly find answers to specific questions. Others read this guide in its entirety. To accommodate desk-reference readers, we edit each chapter to stand alone, which inevitably means some chapters contain information covered in others.

Table of Contents

Highlights. 

Chapter 1  Trader Tax Status.

Chapter 2  Section 475 MTM Accounting. 

Chapter 3   Tax Treatment of Financial Products. 

Chapter 4  Accounting for Trading Gains & Losses. 

Chapter 5   Trading Business Expenses.

Chapter 6  Trader Tax Return Reporting Strategies.

Chapter 7  Entity Solutions. 

Chapter 8  Retirement Plans.

Chapter 9  Tax Planning.

Chapter 10  Dealing with the IRS and States.

Chapter 11  Traders in Tax Court.

Chapter 12  Proprietary Trading. 

Chapter 13   Investment Management.

Chapter 14   International Tax. 

Chapter 15  ACA Net Investment Income Tax. 

Chapter 16   Short Selling. 

Chapter 17  Tax Cuts and Jobs Act.

Chapter 18  CARES Act.

 

Tips For Traders On Preparing 2022 Tax Returns

February 6, 2023 | By: Robert A. Green, CPA

Presentation Slides

Join Robert A. Green, CPA, from GreenTraderTax.com, for insights and information to help traders file their 2022 federal tax returns timely and accurately in 2023.

  • Mr. Green interviews Darren L. Neuschwander, CPA, head of tax compliance services for Green, Neuschwander & Manning, LLC.
  • Learn how traders, eligible for trader tax status (TTS), maximize business expenses, make vital tax elections, and utilize pass-through entities for further tax benefits, including health insurance, retirement plans, QBI, EBL, NOL, and SALT deductions.
  • Learn all the various tax forms to use for multiple types of financial products, dealing with wash sales, and other accounting methods.
  • Learn tips for filing tax extensions and paying taxes on time to avoid penalties.
  • Learn common errors on TTS traders’ tax returns, leading to an IRS or state exam.

If you can’t join us live, register and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

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Tips for Traders on Preparing 2021 Tax Returns

January 26, 2022 | By: Robert A. Green, CPA

Presentation Slides

Join Robert A. Green, CPA, from GreenTraderTax.com, for insights and information to help traders file their 2021 federal tax returns timely and accurately in 2022.

  • Mr. Green interviews Darren L. Neuschwander, CPA, head of tax compliance services for Green, Neuschwander & Manning, LLC.
  • Learn how traders, eligible for trader tax status (TTS), maximize business expenses, make vital tax elections, and utilize pass-through entities for further tax benefits, including health insurance, retirement plans, QBI, EBL, NOL, and SALT deductions.
  • Learn all the various tax forms to use for multiple types of financial products, dealing with wash sales, and other accounting methods.
  • Learn tips for filing tax extensions and paying taxes on time to avoid penalties.
  • Learn common errors on TTS traders’ tax returns, leading to an IRS or state exam.
  • Learn how new tax legislation impacts 2021 tax filings for traders.

If you can’t join us live, register and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

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