Mr. Anolik is a corporate tax attorney with special emphasis on international taxation and risk mitigation strategies.

Mr. Anolik has handled client matters involving international investment and finance, intellectual property migration, transfer pricing, infrastructure project finance, mergers and acquisitions, and international taxation. These clients range from start-ups to Fortune 500 companies, on various international securities and transactional matters, including multi-jurisdictional acquisitions and dispositions of business; cross-border joint ventures; and securities transactions and financings for the U.S., European, Asian, and Latin American companies. In addition, Mr. Anolik provides consulting services to high net worth individuals in regard to estate planning, wealth preservation, and asset protection planning.

Mr. Anolik has extensive experience with insurance matters, including captive insurance, where he consults with mid-market closely held businesses (and the family owners) on the advantages of implementing captive insurance scenarios that can provide benefits in such areas as risk mitigation, cost control, and wealth preservation.

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  • Representative Transactions

    International Taxation and Transfer Pricing

    • Represented a Global Outsourcing Company (“GOC”) with offices in Pakistan, Philippines, Ghana, and the US providing a comprehensive transfer pricing study in connection with the establishment of arm’s length prices for related party transactions involving the various GOC entities, including but not limited to, back-office support, software development services, and software distribution services.
    • Advised several Technology-Software-Telcom companies and their respective affiliates (“TechSo”) regarding TechSo’s intellectual property, and intercompany services throughout around the globe.
    • Advised clients and implemented shared services centers in appropriate domiciles such as Switzerland, Singapore, Ireland, and the Netherlands, among others.
    • Represented global software company regarding the migration of intangibles to domiciles such as Bermuda, Ireland, Mauritius, and Cyprus, among others.
    • Development and implementation of global distribution structures that minimized a company’s worldwide effective tax rate, eliminated withholding tax obligations on various intercompany transactions, and minimized local country income taxation through the use of “stripped” or “low risk” distributor/commissionaire structures.
    • Represented an online gaming company, including the development and implementation of a tax-efficient global structure for software development and maintenance services, a treasury function, and a global marketing and development structure company and assisted with the relocation of the company’s Los Angeles software development workforce to Ireland.
    • Stu represented a software company (“Holding, Ltd”) and its subsidiaries that are in the business of design, develop, market, and sell virtualization and automation software for consumers, businesses, and service providers across all major hardware, operating system, and virtualization platforms. Stu developed and implemented a global tax restructuring of the Holding Ltd group of companies, including performing more than 15 transfer pricing analyses for the firm.

    Captive Insurance and High Net-Worth Families

    Stu represented a family that owns and operates two separate surgical center groups, one with over a $100 million investment by a Private Equity firm and the other a majority of which owned by the family (with key persons owning an aggregate of 10% of the entity). Stu handled and continues to handle the following on behalf of the family:

    • Development and implementation of a captive insurance solution to provide medical malpractice and other coverages (HIPPA compliance, reputational risk, communicable disease, administrative actions, etc.) to the group.
    • Implemented the decanting of existing trusts to Wyoming through the establishment of two Wyoming Irrevocable Family Trusts and a Wyoming private trust company as trustee.
    • Stu provides overall advice to the family concerning (i) the Principal’s dealings with the Private Equity investor, (ii) review and advice on the Federal and state income tax efficiency of the family holdings and (iii) guidance and advice regarding charitable planning, including the gift of medical practice to a large healthcare facility.

    Represented a California resident client in regard to the use of a captive insurance solution, including developing appropriate coverages.  Additionally, developed a wealth preservation structure utilizing a Nevada Irrevocable Trust and implementation of Private Placement Life Insurance policy

    Corporate and Transactional Matters

    • Represented a client in the formation and operation of a telecom private equity fund and handled the investments in the portfolio companies.
    • Represented a government contracting client with its acquisitions of a few complementary entities.
    • Represented a foreign software company with its inbound US corporate tax structure, assisted with a Virginia state sales tax audit, and handled the individual tax issues related to foreign executives being based in the US.
    • Represented a client in the formation of a venture capital fund that seeks to invest in Israeli technology and relocate front end offices to the US.
    • Represented a client that acquired a Special Purpose Acquisition Company (“SPAC”) and oversaw its investment.
    • Represented a client in reviewing its corporate and financial books and records before seeking capital from private equity sources. Stu assisted with the negotiation and definitive agreements related to a private equity investment.
  • Presentations & Teaching Experience
    • Presenter, “An Introduction to Captive Insurance”, Pro Law CLE Webinar, October 2018.
    • Speaker, “Private Investment in Provider Facilities,” International Conference, Self-Insurance Institute of America, Inc., Coral Gables, FL June 2012
    • Speaker, 10th Annual Conference of the Captive Insurance Council of the District of Columbia, Oct 2011
    • Speaker, “IP Taxation and International Tax,” Maryland State Bar Association, Montgomery County Tax Study Group, Rockville, MD, Oct 2011
    • Speaker, “Tax Update,” CalCPA Entertainment Industry Conference, Santa Monica, CA, April 2011
    • Speaker, “International Tax Considerations for a Maryland Company,” “Captive Insurance Opportunities for Non-Insurance Companies,” MACPA 2010 Advanced Tax Institute, Baltimore, MD, Nov 2010
    • “Captive Insurance: an Opportunity to Minimize Risk Mitigation Costs,” in BIZGrowth Strategies, Summer 2011.
    • Speaker, “The 1999 and 2000 Conferences on Advanced Tax Strategy for E-Commerce-Going from Theory to Practice: Tax Strategies for Forming and Structuring a Web-Based Business,” The Conference Board, New York, and San Francisco
    • Speaker, “E-Business: Taxation in a Virtual Marketplace, E-Commerce ’99,” Tel Aviv, Israel


  • Publications
    • Captive Insurance – Making Sense Of It All”, Global Tax Weekly, CCH, September 2013
    • “Captive Insurance: an Opportunity to Minimize Risk Mitigation Costs,” in BIZGrowth Strategies, Summer 2011.
    • “Going Global – unique rules govern the taxation of your new global enterprise,” in Washington SmartCEO, Nov .2008
    • Co-Author, “Controlled Foreign Corporations,” CCH Federal Tax Service M:8.00
    • Co-Author, “OECD and E-Commerce: Clarification or Fundamental Change?,” 11-99 Tax Planning International E-Commerce BNA ISSN 1464-8903
    • Co-author, “Subpart F and Source of Income Issues in E-Commerce,” Tax Notes International, October 2000
    • Co-Author, “Offshore Operations: Taking E-Commerce Operations Offshore,” International Tax Review, 2001
    • Author, International Government Procurement Directory, World Trade Center, Baltimore, Maryland, 1996
    • Co-Author, “Export Financing,” International Newsletter, Signet Bank, December 1996



Washington, D.C.





George Washington University, National Law Center, LLM Taxation-1983

Western New England School of Law-JD-1982

Baruch College, City University of New York, BBA Public Accounting 1979

Practice Areas