Alex Kugelman

Alex Kugelman is the founder and managing attorney of Kugelman Law, a boutique tax controversy and cryptocurrency tax firm serving California and clients nationwide. With nearly two decades of federal tax controversy experience — including litigation in the U.S. Tax Court and U.S. District Court — I represent individuals and businesses in their most consequential disputes with the IRS, the California Franchise Tax Board, and other taxing authorities.

A Tax Practice Built on Two Decades of Federal Controversy Experience

I founded Kugelman Law as an alternative to two flawed options that taxpayers in serious trouble usually face: oversized law firms that treat tax controversy as a side practice, and unregulated tax resolution companies that promise outcomes they cannot deliver. Our clients deserve better than either. They deserve a senior tax attorney personally engaged in their matter, working with a small, expert team built specifically to handle high-stakes federal and state tax disputes.

I have spent my career in federal tax controversy. I have litigated in the U.S. Tax Court and U.S. District Court, defended clients through every stage of IRS and FTB audits, negotiated collections resolutions for clients facing levies and liens, and resolved multi-year non-filing and offshore compliance matters that other firms had given up on.

Today, our practice is strengthened further by the addition of Otto Bosch, a former IRS Revenue Agent from the IRS Global High Wealth Group within the Large Business & International (LB&I) Division. The combination — a senior tax controversy litigator working alongside a former IRS insider who audited the country’s most complex returns — is rare in private practice and gives our clients an unusually clear view of what the IRS is doing, why, and what it is likely to do next.

Nationally Recognized Cryptocurrency Tax Practice

I built one of the earliest dedicated cryptocurrency tax practices in the United States, and I continue to serve as a national resource on crypto tax controversy and compliance. I have been featured on the Bitcoin.tax podcast and The Mark Milton Show, where I discuss the evolving IRS approach to digital asset enforcement, blockchain analytics in audits, NFT taxation, and the practical realities of resolving crypto tax disputes.

Our crypto practice covers the full range of issues clients face: cryptocurrency accounting and IRS crypto audits, NFT accounting and tax compliance, John Doe summons matters, exchange data reconciliation, voluntary disclosures involving digital assets, and pig butchering crypto scam tax recovery work. Few firms in the country combine deep federal tax controversy experience with hands-on crypto fluency. We do.

Practice Areas

My practice focuses on resolving complex federal and state tax disputes for individuals, businesses, high-net-worth taxpayers, and crypto investors. Specific areas include:

• IRS and FTB audit defense, including high-net-worth and small business examinations
• Tax collections defense — levies, liens, wage garnishments, and resolution alternatives
• U.S. Tax Court litigation and U.S. District Court tax matters
• General tax help and pre-controversy strategic counsel
• Unfiled tax return resolution, including multi-year non-filer matters
• Cryptocurrency tax controversy, audits, and accounting
• NFT accounting and tax compliance
• Pig butchering crypto scam tax matters
• Streamlined offshore procedures and offshore voluntary disclosure
• Delinquent FBAR procedures
• Delinquent foreign information return procedures
• California residency and domicile audits

Notable Results

I have spent nearly twenty years getting clients out of tax problems that felt unsolvable when they walked in. A representative sample of outcomes:

• $365,000 tax debt reduced to a zero-dollar liability. A client with a six-figure assessed liability ultimately owed nothing.
• Multi-year audit and non-filing matter resolved with a minimal payment. A complex examination involving multiple unfiled years was resolved on highly favorable terms.
• Ten years of unfiled returns brought into compliance with a successful outcome. A long-term non-filer was returned to compliance and the resulting exposure was dramatically reduced.

Results depend on specific facts. Past results do not guarantee future outcomes.

Leadership, Recognition, and Bay Area Roots

I was admitted to the State Bar of California in 2008 and to the Bar of the U.S. Supreme Court, and I am a member of the American Bar Association, the California State Bar, and the Federal Bar Association. In 2018, I served as the San Francisco Chair of the Federal Bar Association’s Tax Division. I also serve on the Marin County Assessment Appeals Board, where I help adjudicate property tax disputes — a role that reflects my long-standing commitment to the Bay Area tax community.

I earned my Juris Doctor from Chapman University Fowler School of Law in 2007 and hold a B.A. in English Literature from the University of Colorado at Boulder. The English background is not incidental: tax controversy is, at its core, about reading carefully, writing precisely, and arguing persuasively. Those skills win cases.

My Approach

Kugelman Law is a white-glove, paid-consultation firm. We do not advertise free consultations because the work clients hire us for — privileged strategic advice from a senior tax controversy attorney — is too valuable to give away. Every consultation I conduct is a paid, fully privileged conversation protected by attorney-client privilege. Clients leave that conversation with a clear understanding of where they stand, what their options are, and what each path is likely to cost in time, money, and risk.

From there, our work is deliberate. We resolve matters administratively whenever we can, because that is almost always faster and less expensive for the client. When we cannot — when the IRS or FTB has taken an unreasonable position, or when the case demands it — we are prepared to litigate. The clients who get the best outcomes are usually the ones who came in early, told us everything, and let us build the record correctly from day one.

Speak With Alex Kugelman

To discuss an audit, controversy, collections matter, or cryptocurrency tax issue, schedule a paid privileged consultation with Kugelman Law or call (415) 968-1780. All consultations are fully protected by attorney-client privilege.