Accepting trader-tax engagements for current tax year

Section 475(f) elections, trader-status defense, and clean entity setup. Filed by an attorney, not a software.

The 475(f) mark-to-market election unlocks unlimited trading-loss deductions, kills the wash-sale rule, and converts trading into a Schedule C business — but only if the election statement is attached to the right return, the entity is set up in the right order, and the trader-status posture survives audit. I draft the memo, file the statement language, recommend the entity, and stand behind the position if the IRS challenges it.

Sergei Tokmakov, Esq. · CA Bar #279869 · Licensed since 2011
01 · Engage me

Three ways to get the election right.

Flat-fee setup, hourly strategy, or a retained relationship for active traders. Direct work with me — no junior associates, no software intake forms.

Strategy Call

475(f) Election Strategy Consultation

One hour to pressure-test your trader-status posture, walk through deadline mechanics, and decide whether the election fits your situation.

$240/hr
hourly · 60-min Zoom
  • Trader-status qualification assessment against the IRS factors
  • 475(f) election deadline review for your specific facts
  • Walkthrough of the election statement structure
  • Entity-formation discussion (sole prop / LLC / S-corp)
  • Plain-English explanation of MTM accounting consequences
  • Action checklist sent within 24 hours
Retained Counsel

Ongoing Trader-Tax Counsel

Year-round legal support for active traders: CTR/8275 strategy, audit-letter response, K-1 reconciliation, and quarterly check-ins.

$1,500/mo
retained · 3-month minimum
  • Year-round availability for trader-tax questions
  • CTR (Form 8275 disclosure) strategy support
  • IRS audit-letter response and substantiation memos
  • K-1 reconciliation review for partnership traders
  • Quarterly compliance check-ins
  • Discounted hourly rate for matters outside scope
02 · Common failures

Why most traders blow the 475(f) election.

Six errors I see in audit-defense intake and second-opinion engagements. Each one is preventable. Each one is permanent for the year it occurs.

MISTAKE 01

Missed April 15 deadline

The election attaches to the prior-year return by the unextended April 15 due date. Filing an extension does not extend the election deadline. Most missed-elections I review came from a CPA who assumed Form 4868 covered both. It does not.

MISTAKE 02

Wrong entity for the election

Sole proprietors can elect on Schedule C, but moving to an S-corp mid-year creates a stub-period election problem. New entities have a 2-month, 15-day window from start of trading. Get the entity sequence wrong and the election attaches to the wrong taxpayer.

MISTAKE 03

Statement attached to the wrong return

The 475(f) statement attaches to the prior-year return for an existing taxpayer wanting the election effective for the current year. Attaching it to the wrong return is the #1 reason elections get rejected on examination.

MISTAKE 04

Retroactive election attempts

The IRS has consistently rejected late-relief requests for 475(f). Form 3115 with a private letter ruling is the only realistic path, and it costs thousands in user fees with low success odds. There is no "oops" fix — you wait for the next deadline.

MISTAKE 05

Mark-to-market ignored on year-end inventory

Once the election is in force, all open positions are deemed sold at fair market value on December 31. Forgetting this is the second most common audit trigger I see. The deemed-sale gain becomes ordinary income whether you actually closed the trade or not.

MISTAKE 06

Trader-status posture not documented

Trader status itself is a fact-and-circumstances test — trade frequency, holding period, time spent, intent. Without contemporaneous logs, the IRS treats you as an investor and the entire 475(f) election collapses with it.

03 · Decision tree

Do you actually qualify as a trader?

The IRS uses a multi-factor test. Walk through these four questions; the buckets at the bottom tell you whether to file, hold off, or get an analysis.

QUESTION 01

How frequent and continuous is your trading?

The IRS expects "frequent, regular, and continuous" activity — not a few trades a week, not seasonal trading, not buying-and-holding with occasional rotation.

Signals 1,000+ trades/year. Trading on most market days. Trading is your primary activity, not your hobby.
QUESTION 02

What is your typical holding period?

Trader status requires a short holding period. Investors hold for capital appreciation; traders profit from short-term price movement.

Signals Average holding period under a few days. Most positions closed same week. Day trading or short-swing strategies dominate the book.
QUESTION 03

Is trading a substantial activity?

Hours spent matter. The IRS looks at whether trading occupies a significant portion of your time relative to other income-producing activities.

Signals Trading 4+ hours/day during market hours. Time spent on research, charting, and execution rivals or exceeds your day job.
QUESTION 04

Do you have a documented trading business?

The intent factor is documentary — business plan, separate accounts, dedicated equipment, recordkeeping. Without paper trail, the IRS reads you as an investor.

Signals Written trading plan. Dedicated trading account. Equipment used substantially for trading. Bookkeeping separate from personal finances.
Likely yes Strong signals on all four. The setup bundle is the right move — lock in the election, document the posture, file clean.
Need analysis Mixed signals. Strategy consultation first — we may need to formalize the business this year and elect next year.
Likely no Investor profile. The election will fail under audit. Capital-loss planning is a different conversation.
04 · Deliverables

What's actually in the $2,500 setup bundle.

Six artifacts you receive. Each one is written for your specific facts and trade history — not a generic template that breaks under examination.

01

Qualification Analysis

Memo applying the IRS trader-status factors to your trade history, holding-period stats, and time spent. Tells you whether the election will survive audit before you file.

02

Election Filing Memo

The §475(f) statement language drafted to attach to the correct return. Includes IRC citation, taxpayer identifying information, effective tax year, and the trade-or-business description.

03

Entity Recommendation

Written comparison of sole prop vs single-member LLC vs multi-member LLC vs S-corp for your specific volume, capital, and goals. Self-employment tax, retirement contribution ceilings, and audit signal all factored in.

04

First-Year Compliance Roadmap

Month-by-month checklist for the first year under the election: books and records setup, December 31 inventory mark, segregation of investment vs trading positions, year-end reconciliation.

05

Estimated-Quarterly-Tax Planning Sheet

Worksheet projecting quarterly safe-harbor estimates under MTM ordinary-income treatment. Avoids underpayment penalties and the year-end cash crunch most first-year electing traders hit.

06

Recordkeeping Template

Spreadsheet keyed to the IRS factors (frequency, holding period, hours, equipment, intent). Makes the trader-status posture defensible without requiring you to reconstruct it under audit pressure.

05 · How this compares

DIY software vs CPA vs attorney-prepared with a 475(f) memo.

Three paths most traders consider. The audit-survivability column is the one that matters when the IRS challenges the election.

Path
Typical Cost
Audit Survivability
IRS-Position Defense
DIY tax software
$50–$200
Low — statement often misformatted or attached wrong
None
CPA without 475(f) expertise
$1,500–$3,500
Mixed — depends on CPA's trader-tax depth
Limited — CPA can represent in audit but not litigate position
Attorney-prepared with 475(f) memo
$2,500 (this bundle)
High — election + qualification memo + recordkeeping ready for examination
Memo is the legal-position document the IRS appeals officer reads first

Not sure which package fits?

Send me a one-paragraph description of your trading volume, current entity (or none), and prior-year tax filing. I will tell you whether the strategy call is enough or whether the setup bundle makes more sense.

Email me directly
06 · FAQ

Frequently asked questions.

Each answer resolves in one sentence before the expansion. Click any question for the full answer.

What's the 475(f) deadline?
For an existing taxpayer, the unextended April 15 deadline of the prior-year return. Extensions do not extend it.
For an existing taxpayer wanting the election effective for the current tax year, the §475(f) statement attaches to the prior-year return filed by the unextended April 15 due date. New entities have a 2-month, 15-day window from the start of trading. Extensions of time to file the return (Form 4868) do not extend the election deadline — this is the most common reason elections fail.
Can I make the election retroactively?
No, with extremely narrow exceptions. The IRS rejects retroactive 475(f) elections in nearly all cases.
The IRS has consistently denied late-relief requests for 475(f) elections. The only realistic late-relief path is a Form 3115 with an IRS-consent private letter ruling, which involves user fees in the thousands of dollars and a low success rate. The setup bundle includes a deadline-conformity audit so this never becomes the question you are asking. If you have already missed this year's deadline, the right move is planning the next election now.
Do I need an LLC or S-corp first?
Not always. Sole proprietors can elect on Schedule C, but entity choice drives self-employment tax, retirement contributions, and audit posture.
Sole proprietors can make the 475(f) election on Schedule C without forming an entity. But entity selection shapes everything downstream: self-employment tax exposure (S-corp can reduce it), retirement-plan contribution ceilings (solo 401(k) and SEP-IRA limits differ), audit signal (separate-entity bookkeeping is cleaner), and how the IRS reads your trader-status claim. The bundle includes a written entity recommendation tailored to your trading volume, capital, and goals.
What records do I need to keep?
Trade frequency logs, holding-period stats, hours spent on trading, equipment used, and a contemporaneous business plan.
The IRS uses a multi-factor test for trader status: frequency, regularity, and continuity of trading; the holding period of positions; the time and effort spent; and the intent to profit from short-term market movement. Documentation of all four factors needs to be contemporaneous — reconstructed records are heavily discounted on audit. The bundle includes a recordkeeping template keyed to each factor with sample entries.
What if I miss the April 15 deadline?
You wait until the next April 15. There is no automatic late-relief mechanism for §475(f) elections.
If you miss the April 15 deadline, you cannot make the election for that tax year. You wait until the next year's deadline. In the interim you remain stuck with the $3,000 capital-loss limit and the wash-sale rule. The right play is to spend the year formalizing the entity, recordkeeping, and trade-frequency posture so the election survives audit when you do file. The strategy consultation is the right starting point if you have already missed this year.
Does the 475(f) election apply to crypto?
Unclear — the IRS treats crypto as property, and §475(f) applies to securities and commodities. Crypto likely does not qualify.
Section 475(f)(1) covers securities; §475(f)(2) covers commodities. The IRS classifies cryptocurrency as property, and the courts have not extended §475(f) to crypto in any binding ruling. Most practitioners treat crypto as outside the election. If you trade futures or options on crypto traded on a CFTC-regulated exchange, those may qualify under §475(f)(2). The strategy consultation is the right venue for crypto-specific facts.
Are you a California attorney?
Yes — California Bar #279869, licensed since 2011. I work with traders nationwide on §475(f) and trader-tax matters.
I am Sergei Tokmakov, licensed in California (CA Bar #279869) since 2011. Trader-tax federal-law work is not state-specific litigation, so I work with traders across the country. State income-tax overlays (California, New York, Massachusetts especially) are flagged in the memo when relevant.

Conversations on this topic

Real questions from the Terms.Law forum where founders, freelancers, and tenants worked through situations like yours.

Get the election filed right.

Email me a one-paragraph description of your trading volume, prior-year filing, and current entity. I will send back a scope confirmation and the PayPal invoice within one business day.

Email me to start →

Disclaimer. The information on this page is for informational purposes only and does not constitute legal or tax advice. Reading this page or contacting me does not create an attorney-client relationship. Section 475(f) elections are fact-specific and depend on your trade history, entity structure, and prior-year filing posture. Past results do not guarantee future outcomes. Sergei Tokmakov is licensed in California (CA Bar #279869); trader-tax federal-law matters that don't require state-specific litigation are handled nationwide. State-tax overlays are flagged when relevant but state-specific representation is referred out as needed.