Year-Round Crypto Tax Guidance – Not Just at Tax Time
Tax season is one snapshot. The decisions that determine your outcome happen throughout the year – when you stake, when you swap, when you sell, and when an IRS notice arrives. Ongoing advisory support that's there when those decisions get made.
Book a ConsultationFor most clients with regular crypto activity, the highest-value tax planning happens before transactions, not after. By the time tax season arrives, the cost basis is set, the income events have been recognized, and harvesting opportunities have either been captured or lost. Advisory exists to move planning onto the timeline that actually matters.
This service is structured around your decision points, not the calendar. When you're considering a major liquidity event, a move from spot to staking, a switch between protocols, or any other transaction with material tax consequences, you have access to specific, written analysis before you act. When something unexpected happens – an IRS notice, a sudden rule change, a project you invested in tokenizing – you have a defined point of contact who already knows your situation.
Because Joelle is an IRS Enrolled Agent, this also covers direct representation before the IRS for any examination, correspondence, collection, or appeals matter that arises – without having to introduce a new advisor to your situation mid-engagement.
Scope of an Advisory Engagement
Ongoing engagements are structured around a defined cadence plus on-demand access when decisions arise. Specific scope is confirmed in the initial consultation.
Quarterly check-ins
Scheduled quarterly review covering activity since the last check-in, projected tax position for the year, estimated payment status, and any decisions on the horizon. Written summary delivered after each call.
Pre-transaction analysis
Before a material transaction – a large sale, a move from spot to staking, an entity structuring change, an LP exit – you receive a written analysis of the tax impact, alternatives where they exist, and the documentation needed.
Tax-loss harvesting strategy
Identification of positions trading below basis, analysis of harvest timing, application of the (currently inapplicable) wash sale rule to your situation, and a specific harvest recommendation each quarter and at year-end.
Estimated tax planning
Quarterly projections accounting for both realized and pending positions, with safe-harbor calculations to avoid underpayment penalties and a clear quarterly payment recommendation.
IRS notice response & representation
If an IRS notice arrives (CP2000, CP14, examination letter, summons, etc.), Joelle responds on your behalf as your authorized representative under IRS Form 2848 – no need to find new counsel mid-issue.
Year-end planning
Comprehensive year-end review in November/December covering harvesting, deferred recognition, entity-level decisions, and any structural changes to make before December 31. Output is a written year-end action plan.
Advisory Engagements Typically Fit
Clients who would benefit from steady access to a tax advisor rather than a once-a-year filing relationship.
Active investors making frequent decisions
You're actively trading, staking, providing liquidity, or rotating positions, and want tax considerations to be part of the decision rather than a post-hoc accounting exercise.
Founders & businesses with regular activity
Founders of crypto-native companies and businesses with ongoing crypto operations needing a tax advisor who understands the company's structure year-round, not just at filing.
Anyone planning a liquidity event
Token unlock, large position exit, business sale, fund distribution. The tax outcome of a liquidity event is largely determined by decisions made before the event itself.
Clients with prior IRS notices or audits
If the IRS has already contacted you about crypto activity (CP2000, audit notice, etc.), an advisory engagement provides representation and a path to resolution that doesn't restart with each new correspondence.
HNW individuals with complex positions
Substantial portfolios where any single decision (a large sale, a switch into staking, a transition between entities) materially affects total annual tax exposure.
Anyone wanting steady advisor access
Clients who don't fit the standard "send-the-shoebox-in-March" workflow and would rather have predictable access to a tax advisor who already knows their situation.
Real-World Examples
Specific situations clients have brought to advisory engagements.
I'm considering moving 50 ETH from spot to staking through a validator. I want to understand the tax impact before I commit.
Written pre-transaction analysis: the move itself isn't taxable (no disposition), but the staking rewards going forward are ordinary income at fair market value upon dominion and control per Rev. Rul. 2023-14, recognized monthly or per the validator's distribution cadence. Memo includes projected income, basis treatment of rewarded ETH going forward, estimated quarterly tax impact, and the recordkeeping required to support the position. Delivered before the validator selection.
It's November. I have $80,000 of unrealized losses across my portfolio and roughly $300,000 of realized gains for the year. What should I sell before December 31?
Year-end harvest analysis: identification of all positions trading below basis, sorted by potential harvest amount and impact on tax position; recommendation on which to sell (and approximately when to repurchase if desired, given that the wash sale rule under IRC § 1091 has not been extended to crypto); modeled effect on federal and state liability; and the documentation needed to support the harvested losses.
I just received a CP2000 from the IRS about my 2023 crypto activity. The notice says I underreported by $120,000.
Direct representation begins with a Form 2848 authorizing Joelle to act on your behalf. We pull your 2023 records, reconcile the IRS's calculation against your actual basis and dispositions, and respond within the notice's deadline. CP2000s are often based on broker proceeds without offsetting basis – many resolve with no balance due once basis is documented. The response goes out under your representative's signature, not yours.
Cadence of an Advisory Engagement
Different from project-based engagements: a defined rhythm plus on-demand access between scheduled touchpoints.
Onboarding
Initial deep-dive to understand your activity, entities, positions, goals, and risk tolerance. Establishes the baseline that all subsequent advisory work references.
Quarterly check-in
Scheduled 45-60 minute call each quarter covering activity, projected tax position, estimated payment status, and upcoming decisions. Written summary follows each call.
Pre-transaction memos
Triggered when you flag a material transaction or decision. Written analysis delivered before you act, with alternatives where they exist and clear recommendations.
Year-end planning
Dedicated November/December engagement to lock in harvest decisions, structural elections, and any other actions that must be completed before December 31.
Filing season & representation
If we also prepare your returns, advisory feeds directly into filing. If not, we coordinate with your preparer. Any IRS correspondence during the year is handled under our Form 2848 authorization.
Relevant IRS Guidance & Authorities
Advisory work draws on the full body of crypto tax guidance plus the specific representation authority that comes with an Enrolled Agent license.
IRC § 1091 (Wash Sale)
The wash sale rule disallowing losses on substantially identical securities sold and repurchased within 30 days. Currently does not apply to crypto by its terms, enabling specific harvesting strategies – a position that may not last forever.
IRC § 1(h)(5) (Collectibles)
The 28% long-term capital gain rate for collectibles. Advisory analysis identifies positions likely subject to this rate (especially NFTs) so the higher rate is factored into harvesting and timing decisions.
Form 2848 Representation
An Enrolled Agent is one of three credential categories (CPA, EA, attorney) authorized to represent taxpayers before the IRS without limitation. Form 2848 establishes the representation relationship for all examinations, collections, and appeals matters.
Circular 230
The Treasury Department regulations governing practice before the IRS. Establishes the standards of conduct, written-advice rules, and competency requirements that govern advisory work by EAs and CPAs.
Form 1040-X & Amended Returns
The procedural vehicle for correcting prior-year returns. Advisory frequently includes amended returns to capture missed positions, correct treatment, or respond to IRS notices.
Notice 2014-21 & Subsequent Guidance
The foundational crypto guidance plus all subsequent Revenue Rulings, Notices, and Regulations that shape ongoing advisory positions. Advisory engagements stay current as new guidance is published.
FAQs About Crypto Tax Advisory
Questions clients ask about ongoing advisory and tax planning. Each links to a fuller answer in our FAQ.
Plan Ahead, Not After
Advisory engagements pay off most when started before a major decision. If you're contemplating one – or simply want a steady advisor relationship – start with a free 30-minute consultation.
Book a Consultation