Alexander R. Olama

How Alex Helps Clients

Alex focuses his practice on tax controversy and litigation disputes, as well as domestic and international tax planning and compliance matters, for high-net-worth individuals and multinational companies. 

From the initial Internal Revenue Service (IRS) examination letter to full scale litigation in the U.S. Tax Court and federal district courts, Alex provides comprehensive representation for individuals and businesses facing complex and high-stakes tax disputes ranging from income tax deficiency to refund litigation disputes. He also represents individuals and companies in examinations, appeals, and other proceedings before the IRS covering a wide range of federal tax matters, including employee retention credits (ERC), charitable contribution and valuation disputes, changes in accounting method, penalty and interest abatements, business bad debts, net operating losses (NOL), and whistleblower claims. 

In addition, Alex is well versed in offshore tax compliance, including providing advice with respect to the IRS voluntary disclosure programs, IRS Streamlined Filing Compliance Procedures, Foreign Account Tax Compliance Act (FATCA), Report of Foreign Bank and Financial Accounts (FBAR), Foreign Investment in Real Property Tax Act of 1980 (FIRPTA), foreign tax credits (FTC) and foreign earned income exclusion (FEIE), expatriation tax compliance, and tax treaties.

Alex has been recognized by his peers as a Florida Super Lawyers Rising Star in 2020-2024.  

Clients trust me to explain their options clearly, set realistic expectations on timing and cost, and guide them toward a practical resolution.

What Clients Can Expect 

Alex provides practical, results-driven solutions to complex tax controversies. He takes the time to understand a client’s business, financial situation, and goals, providing strategic advice and guidance at every step. He believes tax touches everything, and clients trust him to assemble skilled teams across disciplines and jurisdictions.

Alex acts decisively to manage risk and navigate challenging situations. Whether the controversy is before the IRS or a court, Alex crafts practical solutions that achieve results while maintaining the highest level of discretion.  Business leaders and high-net-worth individuals value his judgment, reliability, and proven ability to deliver under pressure.

Outside the Office

Alex enjoys golf, strategic board games, military history, and hiking trails with his wife and their two rescue dogs. 

Proof Points 

• Litigated a seven-day U.S. Tax Court trial defending the valuation of corporate stock, resulting in a favorable settlement and IRS concession of over $2.3 million in penalties.
• Negotiated a settlement resolving federal tax liabilities and mitigated interest dating back to the 1990s in a complex U.S. district court collection action.
• Represented whistleblower in U.S. Tax Court and U.S. Court of Appeals for the District of Columbia Circuit regarding claims against foreign financial advisors who facilitated U.S. taxpayers’ offshore income and asset concealment.
• Advised high-net-worth individuals regarding U.S. tax compliance involving interests in foreign entities and assets, residency-based positions, and expatriations.
• Negotiated abatement of approximately $1 million of employment tax and information return penalties before the IRS Independent Office of Appeals.
• Represented dozens of taxpayers in ERC controversies, resulting in millions of dollars in refunds through strategic negotiation and comprehensive documentation.