Chicago · Nationwide Practice
Bill Brock, CPA, and Natalie Neumann, EA, work with serious crypto investors year-round: tracking cost basis, preparing defensible returns, and planning around evolving IRS guidance. They also handle IRS notices, audits, and unfiled returns — with the conservative positions and aggressive written advocacy that contested crypto cases require.
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
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.
Reading What Others Miss
The tax code rewards close reading. Bill's academic background means he works through regulations, deal documents, and IRS correspondence with close attention to what the language actually says, and where it leaves room to act.
Strong Written Positions
IRS protest letters, tax memos, and audit responses are only as strong as the argument behind them. Bill writes with the force and rigor of someone trained to mean exactly what he says, and to fight for it.
Significant IRS Representation Experience
From routine correspondence to cryptocurrency audits, Bill has represented clients before the IRS across a wide range of matters, with the depth to back every position taken.
William H. Brock
Ph.D., CPA — Principal
Cryptocurrency Tax
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.
Read more →Received an IRS Notice?
Don't respond without counsel. Bill has represented crypto holders through examination and at Appeals, a narrower skill set than most CPAs offer.
Read more →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 voluntary approach to back filings addresses the reporting gap before the IRS makes contact.
Read more →Considering Puerto Rico?
Qualification is fact-specific, and the ongoing compliance obligations don't end at the move. Getting the structure right from the start matters.
Read more →What We Do
From straightforward consulting to multi-year IRS matters, the practice is built around situations where experience and expertise genuinely matter.
IRS-compliant reporting for crypto investors, traders, and digital asset holders. Audit representation, coming-into-compliance work, and proactive planning.
Learn more →Representation at examination and at Appeals. Particular depth in cryptocurrency audit representation, including cases where the underlying legal positions are still being contested.
Learn more →Comprehensive tax counsel for affluent families and family offices, including estates, trusts, multi-generational planning, and coordination across complex asset portfolios.
Tax consulting for real estate investors and developers, plus estate and trust taxation for families navigating generational wealth transfer.
Startups, reorganizations, acquisitions, and sales. Strategic tax planning for every stage of the business lifecycle, from formation to exit.
C corporations, S corporations, and partnerships — from preparation through strategic structuring. Real estate, personal service corporations, and technology companies.
Representative Work
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.
Individual · Puerto Rico Relocation
A high-net-worth crypto investor considering relocation to Puerto Rico under Act 60 needed a thorough analysis of qualification requirements, ongoing compliance obligations, and the tax consequences of their specific asset mix before making the move.
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.
Read more about IRS representation →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 structured a voluntary disclosure approach, reconstructed the transaction history exchange by exchange, and filed the back returns with documented positions on each contested issue.
Crypto · IRS Examination · Attorney Engagement
A four-year IRS examination of a crypto-active taxpayer produced a third-party tax calculation report proposing more than $25 million in adjustments. 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 nearly $4 million of income misattribution, documented overstatements of the taxpayer's year-end positions by hundreds of Bitcoin, and traced one million-dollar "income" entry to a blockchain transaction that did not involve the taxpayer. The taxpayer's counsel used the findings to settle the matter for under $100,000.
Past results depend on the specific facts of each engagement; outcomes in other matters will differ.
What the IRS knows about your crypto →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
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
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 often isn't equipped to handle crypto-specific issues at the level a serious holding warrants. Bill brings deep crypto tax specialization 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 most generalist tax practitioners haven't seen: 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 Investors Considering Puerto Rico Opportunity Zones
The Qualified Opportunity Zone framework was substantially revised by the One Big Beautiful Bill Act (H.R. 1, P.L. 119-21, July 2025). For Puerto Rico in particular, the changes are significant: the special rule that automatically designated 98% of the island as a QOZ has been repealed, and Puerto Rico must now participate in the same nomination-based designation process as the states. Existing PR QOZs remain effective through December 31, 2027; new designations under the post-H.R. 1 cycle take effect January 1, 2027 and run through 2036. The new map is not yet finalized.
For taxpayers with significant capital gains in the second half of 2026, this creates a specific planning window. A gain realized in late 2026 with a 180-day investment period extending into 2027 can support a post-December 31, 2026 QOF investment — which qualifies for the new permanent regime: a five-year deferral measured from the investment date, a 10% basis increase after five years, and the exclusion of post-investment appreciation after a 10-year hold. Layered onto the federal benefits, Puerto Rico's Act 60 incentives offer a transferable investment tax credit of up to 25%, a fixed 18.5% income tax rate on QOZB net income, and exemptions from local property, dividend, interest, and municipal taxes for fifteen years, all subject to securing an exemption decree from the Industrial Tax Exemption Office.
Bill's role in this work is as the U.S. tax structuring and capital gains deferral advisor — analyzing the transition rules, structuring the QOF investment to qualify under the post-2026 regime, and coordinating with Puerto Rico counsel and Act 60 regulatory advisors who handle the decree application and local incentives compliance. This is structuring and advisory work for clients evaluating whether a PR QOZ investment is the right home for their deferred gain; it is not lead-role fund formation or capital raising.
A few principles shape what we think this work should look like. The investments worth pursuing are ones that build rather than displace — middle-class housing that residents can actually live in, office and commercial redevelopment that creates jobs on the island, services businesses serving the local economy. The structures worth pursuing are ones with careful decree drafting, including provisions for amending the decree to cover successive projects without losing the original 2027 map's eligibility. The clients worth working with are ones treating this as long-term capital deployment in a place, not a tax-avoidance play or a short-term tourist conversion.
If you have material capital gains in 2026 and are considering a Puerto Rico QOZ investment, a conversation about timing, structure, and whether this fits your situation is worth the fifteen minutes.
Contact Bill Directly →For Tax Controversy Counsel
Crypto examinations generate work product that may later be subject to discovery. Bill's firm is available for Kovel engagements 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