Otto Bosch

Otto Bosch is a former IRS Revenue Agent from the Global High Wealth Group within the IRS Large Business & International (LB&I) Division — the specialized unit that examines the most complex returns of the wealthiest U.S. taxpayers. I served in that role before I joined Kugelman Law to bring direct, inside-the-IRS experience to clients facing audits, controversies, and high-stakes federal tax matters.

From Inside the IRS Global High Wealth Group to Your Side of the Table

Most tax attorneys learn the IRS from the outside — through notices, transcripts, and reported case law. I learned it from the inside. Within the IRS Global High Wealth Group, I worked the same kind of complex examinations our firm now defends against: Information Document Requests, Notices of Proposed Adjustments, partnership compliance issues, related-party transactions, hobby loss disputes, and the layered portfolio-level adjustments that are routine in high-net-worth audits.

I led issue meetings with taxpayers and audit teams, balanced compliance posture against litigation risk, and served as the intermediary with IRS Counsel. As part of Global High Wealth’s enterprise audit approach, I developed and resolved more than a dozen high-value adjustments — the kind that, outside that specialized approach, would not have surfaced at all. I also delivered technical training and led post-conference feedback sessions for examination teams.

That is the perspective I now apply on behalf of clients facing an IRS audit, collections action, or U.S. Tax Court matter. I know how returns get selected, how revenue agents are trained to develop issues, where the real risks hide inside an examination, and which arguments genuinely move an agent, manager, appeals officer, or IRS counsel attorney. I helped run the playbook. Now I work for our clients.

What an IRS Insider Brings to Your Case

Clients hire Kugelman Law for a reason most firms cannot claim: a former IRS Global High Wealth Revenue Agent reviewing their matter alongside seasoned tax controversy counsel. In practice, that means I help clients:

• Anticipate what the agent will request before the Information Document Request arrives
• Identify weak IRS positions early and use them in negotiation, appeals, or trial
• Avoid the disclosures, statements, and missteps that quietly turn routine examinations into eggshell audits or fraud referrals
• Speak the agent’s language during examinations, IDR responses, and managerial conferences
• Position cases for the most efficient resolution possible — administratively wherever we can, and through litigation when we must
• Build a clean, defensible record from day one in case the matter advances to Appeals or U.S. Tax Court

Practice Areas

My practice focuses on federal, state, and international tax matters, with particular emphasis on tax controversy, complex pass-through entity taxation, and high-net-worth taxpayer issues. I advise clients through every stage of a tax dispute — from IRS audit strategy and information development through administrative resolution and litigation. Specific areas include:

• IRS audit defense for individuals, businesses, and high-net-worth taxpayers, including Global High Wealth and LB&I matters
• Tax collections, levies, liens, and resolution alternatives
• U.S. Tax Court litigation and administrative appeals
• Partnership and S-corporation taxation, including related-party transactions and complex flow-through structures
• Cryptocurrency tax controversy and IRS crypto audits
• Multi-jurisdictional and cross-border tax matters, including streamlined offshore procedures and delinquent FBAR filings
• Penalty abatement and unfiled tax return resolution
• Mergers, acquisitions, and transactional tax diligence
• Enterprise compliance reviews, nonprofit matters, and employee benefit plan issues

Background Beyond the IRS

Before joining the IRS, I served as a Senior Consulting and Research Associate at KPMG LLP – Washington National Tax (WNT), advising national and multinational clients on complex partnership and S-corporation transactions, drafting responses to taxing authorities, and producing technical opinions and memoranda on regulatory developments. Earlier KPMG roles focused on state and local tax, mergers and acquisitions, and IRS conformity issues. I have also worked in private practice on partnership and S-corporation compliance, transactional tax diligence, and employee benefit plan and nonprofit audits.

I hold an LL.M. in Taxation from the University of Missouri–Kansas City School of Law, where I focused on Partnership Tax. While in the LL.M. program, I was named the ABA Tax Challenge Winner for Best Written Work Product (LL.M. Division). I am an IRS Enrolled Agent and a member of the Missouri Bar. I am also fluent in Spanish, both spoken and written, and represent Spanish-speaking clients in federal tax matters.

My Approach

I work the way I learned to work inside the IRS: methodical, document-driven, and focused on the facts that actually move a case. That means rigorous issue development, technically sound memoranda, and responses to taxing authorities that anticipate the agent’s next move rather than react to it. It also means pragmatism — most controversies should be resolved at the lowest administrative level possible, and when they cannot, the case file should already be built for what comes next.

For sophisticated clients, much of the most valuable work happens before any dispute exists: transactional diligence, structural analysis, and enterprise compliance reviews designed to reduce exposure long before a notice arrives. That is the same risk-assessment lens I applied as a Revenue Agent in the Global High Wealth Group — now used to protect the client instead of the government.

Speak With a Former IRS Revenue Agent

To discuss how Otto’s IRS Global High Wealth background can change the trajectory of your audit, controversy, or complex tax matter, schedule a paid privileged consultation with Kugelman Law or call (415) 968-1780. All consultations are fully protected by attorney-client privilege.