My practice focuses on federal, state, and international tax matters, with an emphasis on tax controversy, complex pass-through entity taxation, and high-net-worth taxpayer issues. I advise clients through all stages of tax disputes, from audit strategy and information development to administrative resolution, helping individuals and businesses navigate examinations, proposed adjustments, and compliance challenges while balancing litigation risk and practical business outcomes. Drawing on experience within both government and private practice environments, I provide strategic guidance on partnership and S-corporation taxation, related-party transactions, and technical issues frequently arising in sophisticated investment and operating structures.
I regularly counsel clients on multi-jurisdictional tax matters, including state and local tax compliance, conformity issues, and the tax implications of mergers, acquisitions, and other business transactions. My work includes drafting technical analyses, memoranda, and responses to taxing authorities, as well as advising on controversy procedures, penalties, and regulatory developments affecting complex taxpayers. I also assist in transactional diligence and risk assessment, helping clients anticipate and mitigate exposure before disputes arise.
In addition, my practice has included tax research and regulatory analysis involving some international and cross-border considerations, enterprise-level compliance reviews, and nonprofit and employee benefit plan matters. I bring a practical, solutions-oriented approach shaped by experience coordinating with auditors, counsel, and stakeholders, enabling clients to resolve disputes efficiently while maintaining long-term compliance and strategic tax positions.
Bar Associations
- J. Reuben Clark Law Society – UMKC Chapter
Member Since: 2021
- Kansas City Metropolitan Bar Association
Member Since: 2021
- Hispanic Bar Association of Greater Kansas City
Member Since: 2021
Education
- University of Missouri - Kansas City - Taxation LL.M. - 2024
- School University of Missouri - Kansas City - J.D. - 2022
- CALI Awards: Taxation of Estates, Gifts & Trusts (2019)
- Tax-Exempt Organizations (2020)
- ABA Tax Challenge Winner – Best Written Work Product (LL.M. Division), Feb. 2022
- University of Utah - Masters of Accounting - Taxation - 2020
- University of Central Missouri - B.S. Political Science - 2017
- Cum Laude
- Honors: Dean’s List (2014–2017)
- President, Pre-Law Student Association (2 years)
- Justice, Student Government Association Supreme Court (2 years)
- University of Central Missouri - B.S. Criminal Justice - 2017
Cum Laude
Practice Areas
Tax Controversy & IRS Disputes
- IRS examinations and audit defense (high-net-worth and complex taxpayers)
- Response and resolution of Notices of Proposed Adjustment (NOPAs) and Information Document Requests (IDRs)
- Administrative controversy and pre-litigation resolution
- IRS partnership compliance disputes
- Penalty analysis and litigation risk assessment
- Representation support and coordination with government counsel
- Settlement strategy and issue resolution
Federal Taxation
- Partnership taxation
- S-corporation taxation
- High-net-worth individual taxation
- Related-party transactions
- Hobby loss and economic substance issues
- Transactional tax analysis
- Tax opinion and memorandum drafting
State & Local Tax (SALT)
- Multi-state tax compliance and planning
- State conformity to federal tax law
- Uniformity and nexus issues
- State tax controversy and administrative processes
- SALT implications in mergers & acquisitions
- Regulatory and legislative tax analysis
Tax Compliance & Risk Management
- Complex return review and compliance oversight
- Evidence development and documentation strategy
- Enterprise-level audit coordination
- Regulatory interpretation and implementation
Tax Litigation Support
- Pre-trial preparation and case development
- Settlement negotiations support
- Case organization and advancement
- Low-income taxpayer advocacy
Nonprofit & Employee Benefits Taxation
- Employee benefit plan audits
- Nonprofit compliance and examination support
Tax Research & Regulatory Analysis
- Legal research and statutory interpretation
- Regulatory guidance analysis
- Technical training and professional education
- Drafting technical tax guidance and advisory materials
Industry Areas
Featured Pro Bono Activities
Client Reviews
Alex, Grace and Jon are the best crypto tax team you could hope for! They can tackle hugely complex, nightmarish tax cases with relative ease. They’re incredibly talented professionals who really know what they’re doing. I only wish I knew about Kugelman Law sooner!
Alex was more than helpful in helping me figure out some complicated cryptocurrency-related tax issues. Had detailed knowledge of where the IRS currently stands on crypto-related issues.
Kugelman Law is outstanding! I highly recommend their services! The team members all work together in a professional, knowledgeable, caring, kind, and compassionate manner. Alex is an amazing attorney who approaches challenging tasks with patience, optimism and efficiency, and we are so grateful for...
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San Francisco, CA 94111
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Irvine, CA 92618

