Alexander R. Olama

Alexander Olama is a tax attorney in Holland & Knight's Tampa office, where he focuses his practice on tax controversy and litigation disputes, as well as domestic and international tax planning, for individuals and companies.

From the initial IRS examination letter to full-scale litigation in the U.S. Tax Court and federal district courts, Mr. Olama provides comprehensive representation for individuals and businesses facing complex and high-stakes tax disputes ranging from income tax deficiency petitions to refund litigation. He also represents individuals and companies in examinations and appeals before the IRS covering a wide range of federal tax issues, including employee retention credits (ERC), installment sale obligations, changes in accounting method, abatement of penalties and interest, business bad debts and net operating losses (NOL).

In addition, Mr. Olama 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 planning and compliance and tax treaty benefits.

Prior to joining Holland & Knight, Mr. Olama was a tax attorney for a boutique international tax law firm.

Representative Experience

• Litigated a seven-day U.S. Tax Court trial involving the valuation of a charitable contribution of corporate stock, leading to the IRS conceding all penalties
• Defended a multi-state entrepreneur in a U.S. District Court collection action filed by the U.S. Department of Justice (DOJ), securing a DOJ-approved settlement for tax assessments dating back to the mid-1990s
• Defended transferee of a taxpayer's estate in a U.S. district court federal tax lien foreclosure action filed by the DOJ, achieving a favorable settlement and obtaining a certificate of discharge
• Served as lead counsel in multiple U.S. Tax Court whistleblower cases involving foreign financial advisors assisting individuals in concealing unreported foreign income and assets; whistleblower received a multi-million dollar award after years of investigation and litigation
• Served as lead pro bono counsel in U.S. Tax Court on behalf of an active duty U.S. military service member as part of the Governor's Initiative on Lawyers Assisting Warriors (GI LAW), resulting in complete IRS concession of asserted income tax deficiencies and penalties
• Serves as lead counsel in numerous employee retention credit (ERC) examinations and appeals and secured millions of the dollars of refunds, addressing issues such as gross receipts and governmental orders-based eligibility, ERC calculations, instrumentality determinations and aggregated groups
• Advised an expatriate client in achieving U.S. tax and reporting compliance without penalties for multi-year cryptocurrency income and foreign asset reporting omissions
• Represents taxpayers in IRS collection matters, including conducting Collection Due Process (CDP) hearings and resolving federal tax lien and levy actions
• Served as counsel for hundreds of taxpayer disclosures involving unreported foreign income and foreign assets under IRS Offshore Voluntary Disclosure Programs, Streamlined Foreign Offshore Procedures and Streamlined Domestic Offshore Procedures, Delinquent International Information Return Submission Procedures, Delinquent Report of Foreign Bank and Financial Account (FBAR) Submission Procedures and IRS Service Center filings
• Advised numerous clients on U.S. tax and information return reporting requirements relating to pension and retirement plans from countries including the United Kingdom, Canada, Australia, Switzerland, Ireland, Italy and Japan
• Advises numerous clients regarding U.S. tax compliance involving international information returns, including:
  • Form 5471 (Information Return of U.S. Persons With Respect To Certain Foreign Corporations)
  • Form 5472 (Information Return of a 25% Foreign-Owned U.S. Corporation or a Foreign Corporation Engaged in a U.S. Trade or Business)
  • Form 8865 (Return of U.S. Persons With Respect to Certain Foreign Partnerships)
  • Form 8858 (Information Return of U.S. Persons With Respect to Foreign Disregarded Entities (FDEs) and Foreign Branches (FBs))
  • Form 3520 (Annual Return To Report Transactions With Foreign Trusts and Receipt of Certain Foreign Gifts) and Form 3520-A (Annual Information Return of Foreign Trust With a U.S. Owner)
  • Form 926 (Return by a U.S. Transferor of Property to a Foreign Corporation)
  • Form 8621 (Information Return by a Shareholder of a Passive Foreign Investment Company or Qualified Electing Fund)
  • Form 8938 (Statement of Specified Foreign Financial Assets)
  • Form 8840 (Closer Connection Exception Statement for Aliens)
  • Form 8833 (Treaty-Based Return Position Disclosure Under Section 6114 or 7701(b))
  • Form 8854 (Initial and Annual Expatriation Statement)
• Represented a global airline in a multi-year U.S. excise tax examination, resulting in multiple refunds and no penalties
• Successfully negotiated abatement of approximately $1 million of employment tax and information return penalties for a manufacturer before IRS appeals
• Counseled numerous non-U.S. clients on structuring U.S. real property investments and related Foreign Investment in Real Property Tax Act of 1980 (FIRPTA) tax and withholding implications
• Advised several healthcare industry clients regarding employee reimbursement and other expense allowance arrangements (including per diem allowances) and mitigating noncompliance within IRS guidelines