Chicago · Nationwide Practice
Crypto Tax.
We Know the Territory.
Bill Brock, CPA, and Natalie Neumann, EA, work with serious crypto investors year-round: tracking cost basis, preparing returns with documented reporting positions, and planning around evolving IRS guidance. They also handle IRS notices, audits, and unfiled returns — including written advocacy in IRS examinations and administrative Appeals where positions are contested.
Ongoing Crypto Clients
Year-Round Engagement
Cost basis tracking, annual filing, and proactive planning as the regulatory picture develops
Crypto Tax
IRS Notices & Audits
Examination and Appeals representation for crypto holders, including contested positions where the law is still unsettled
Also
High-Net-Worth Families
Estates, trusts, real estate, corporations, and complex individual returns
The IRS's numbers aren't always right. Here's one example.
IRS Proposed
More than $25 million.
Our Review Found
Nearly $4 million of income misattribution.
Matter Settled
Under $100,000.
Past results depend on the specific facts of each engagement; outcomes in other matters will differ.
About William H. Brock
The Kind of Advisor Who
Reads the Fine Print.
Most accountants apply the rules as written. Bill Brock reads them. When the law is ambiguous or guidance is thin, he works through it, takes a position, and helps clients understand the tradeoffs of where to stand.
That analytical habit, built over decades of CPA practice and informed by a background in academia, is what separates his work from a standard tax preparation engagement. He's not a tax attorney, but he's the kind of advisor who will tell you when you need one, and what to bring to that conversation.
This is not a large firm with rotating staff. When you work with W. H. Brock & Associates, you work directly with Bill Brock, CPA, and Natalie Neumann, EA, his senior cryptocurrency accountant.
Close Reading of the Code and the Blockchain
Statutes, regulations, and IRS correspondence, read against on-chain activity and exchange records transaction by transaction. Bill's academic background shows in how he works through what the language actually says, and where it leaves room to act.
Written Protests, Memoranda, and Audit Responses
Protest letters to the IRS Independent Office of Appeals, technical memoranda, and examination responses, grounded in facts and authorities.
IRS Representation: Examinations, Notices, and Appeals
From routine correspondence to cryptocurrency audits, Bill has represented clients before the IRS across examinations, notices matters, and administrative Appeals.
Cryptocurrency Tax
Crypto Tax Is a Year-Round
Conversation, Not an April Problem.
Crypto taxation covers two distinct kinds of work, and this practice handles both. For ongoing clients: cost basis tracking, annual filing, and planning as IRS guidance develops. For clients dealing with the IRS: notices, audits, unfiled returns, and Appeals representation — with the experience to take a position and defend it in a field where the rules are genuinely contested.
Ongoing Tax Planning & Filing
For investors who want a year-round relationship: cost basis tracking across wallets and exchanges, annual return preparation, and planning conversations as positions evolve and IRS guidance develops.
For more information →Received an IRS Notice?
Prompt review of an IRS notice helps preserve your response options. Bill has represented crypto holders through examination and at the IRS Independent Office of Appeals.
For more information →FTX, Celsius & Exchange Bankruptcies
Tax work for taxpayers affected by FTX, Celsius, Genesis, and similar exchange or lender failures. The tax characterization of bankruptcy distributions — return of capital, ordinary income, capital loss, in-kind vs. cash, timing of recognition — is genuinely contested, and the right answers depend on the specific creditor class, distribution mechanics, and the taxpayer's prior basis position. We've handled these matters during active recovery and can coordinate with bankruptcy counsel where the engagement structure warrants it.
Years of Unfiled Crypto Returns?
Coming into compliance is possible, and acting sooner generally means more options. A structured corrective filing approach addresses the reporting gap before IRS contact.
For more information →What We Do
Tax Advisory Across the Full
Complexity Spectrum
From straightforward consulting to multi-year IRS matters, the practice is built around situations where experience and expertise genuinely matter.
Cryptocurrency Taxation
IRS-compliant reporting for crypto investors, traders, and digital asset holders. Audit representation, coming-into-compliance work, and proactive planning.
For more information →IRS Representation
IRS examination and administrative Appeals representation by a CPA and enrolled agent. Particular depth in cryptocurrency audit representation, including cases where the underlying legal positions are still being contested.
For more information →High-Net-Worth Families
Comprehensive tax advisory services for affluent families and family offices, including estates, trusts, multi-generational planning, and coordination across complex asset portfolios.
Real Estate & Estates
Tax consulting for real estate investors and developers, plus estate and trust taxation for families navigating generational wealth transfer.
Business Tax Consulting
Startups, reorganizations, acquisitions, and sales. Strategic tax planning for every stage of the business lifecycle, from formation to exit.
Corporate Tax Returns
C corporations, S corporations, and partnerships — from preparation through strategic structuring. Real estate, personal service corporations, and technology companies.
Representative Work
Representative Matters
A sample of the situations this practice handles. Details are illustrative of the nature and complexity of typical engagements.
Crypto · Ongoing Tax Planning
An active crypto investor with holdings across multiple wallets and exchanges engaged the practice for year-round service. Bill and Natalie track cost basis on an ongoing basis, advise on the tax implications of significant transactions before they execute, and prepare annual returns with documented positions on each contested reporting question.
Crypto · IRS Audit Representation
A long-term Bitcoin holder received an IRS examination notice covering three years of unreported gains. Bill reconstructed the full transaction history, documented a conservative cost basis position, and represented the client through examination and into Appeals. The audit closed with a reduced assessment.
Past results depend on the specific facts of each engagement; outcomes in other matters will differ.
Crypto · Coming Into Compliance
An early crypto adopter with years of unfiled returns across multiple exchanges needed to come into compliance before the IRS made contact. Bill developed a structured corrective filing strategy, reconstructed the transaction history exchange by exchange, and filed the back returns with documented positions on each contested issue.
Crypto · IRS Examination · Attorney Engagement
In a multi-year, attorney-directed IRS examination of a crypto-active taxpayer, a third-party tax calculation report proposed a large adjustment built on flawed data. Bill's firm conducted a transaction-level review of the IRS's underlying dataset — reconstructing running balances across dozens of wallets and exchanges, tracing intermediary addresses, and verifying on-chain activity against the report's entries. The review identified several million dollars of income misattribution, documented overstatements of the taxpayer's year-end positions by hundreds of Bitcoin, and traced a seven-figure “income” entry to a blockchain transaction that did not involve the taxpayer. Counsel used the findings to resolve the matter.
Representative of the nature and complexity of typical engagements.
Crypto · Estate · Post-Death Planning
A decedent held a substantial Bitcoin position at the 2017 peak. Bill prepared the Form 706, structured the DSUE election to preserve exclusion for the surviving spouse, advised on the multi-year gifting strategy that followed, and handled the tax characterization and Form 1041 reporting of a multimillion-dollar Mt. Gox distribution across three distinct tax categories: ordinary income, long-term capital gain, and return of basis.
Get Started
Tax Work That Matches
Your Complexity.
Whether you're facing an IRS examination, planning a major transaction, or simply need a tax advisor who matches your level of complexity, let's talk.
For Family Offices and Estate Counsel
A Note for Family Offices and Estate Planning Counsel
Family offices. Crypto sits awkwardly across most family office service architectures. The custody and reporting questions don't fit cleanly into traditional alternative-asset workflows, the tax positions are genuinely contested, and the routine outside tax provider may not focus on crypto-specific issues at the level a serious holding warrants. Bill focuses on cryptocurrency tax issues, combined with firsthand experience of how a family office actually operates: the coordination across advisors, the discretion, and the structural role of the principal advisor or family CFO. He's comfortable working as the crypto specialist within an existing architecture rather than as a competing relationship.
Estate planning counsel. Crypto in estates raises issues many general tax practices encounter less frequently: post-death valuation in volatile markets, basis reconstruction across years of activity, the coordination of estate tax filings with subsequent gifting strategies, and the tax characterization of bankruptcy distributions where the right answer depends on the specific asset, the timing of dominion and control, and the underlying creditor position. Bill has handled crypto positions worth tens of millions through estate and post-death planning — including a Form 706 for a decedent holding a substantial Bitcoin position at the 2017 peak, the DSUE election that preserved exclusion for the surviving spouse, the multi-year gifting strategy that followed, and the tax characterization and Form 1041 reporting of a multimillion-dollar Mt. Gox distribution across three distinct tax categories (ordinary income, long-term capital gain, and return of basis). He works alongside counsel as a tax and accounting specialist on defined matters.
For both audiences: a short pre-engagement conversation about scope and structure is usually worth the fifteen minutes.
Contact Bill Directly →For Tax Controversy Counsel
A Note for Tax Controversy Counsel
Crypto examinations generate work product that may later be subject to discovery. The firm can work under attorney-directed engagement structures, including Kovel arrangements where counsel prefers that structure.
For controversy counsel handling crypto work, a short pre-engagement conversation about engagement structure is often worth the fifteen minutes.
Contact Bill DirectlyOffice
4001 W. Devon Ave., Suite 209
Chicago, IL 60646