Legal Services

CROSS BORDER TAX PLANNING FOR BUSINESSES

Integrating international tax planning with global business management is essential to the success of your business. Ensuring compliance with Canadian, U.S. and foreign tax laws to avoid costly penalties and the development of tax efficient global strategies can increase a company’s after-tax profitability.
 
In international corporate tax problem solving, prevention is the best cure. Where proper planning has not been undertaken corporate tax problems can have many significant downsides. These downsides can include: impeding access to markets, damaging customer goodwill, hindering economic opportunities, wrecking succession planning and creating enormous costs which can swamp corporate profits.
 
Cross border tax management involves an extraordinary effort in co-managing a process which is both multi-disciplinary (e.g., legal, business, accounting, treasury) and multi-jurisdictional (e.g., Canada, U.S., sub-national jurisdictions). During the past twenty years I have co-managed (with C-suite officers) teams of professionals in multiple jurisdictions through feasibility, design, implementation and post implementation stages of international business expansions and optimization projects.
 
Our Services
  1. Design and implementation by an international tax lawyer of tax optimized (and related legal) strategies for Canadian companies (private and public) and funds (pension, private equity) investing in and expanding to the United States including for both federal and state and local levels or U.S. companies expanding internationally.
  2. General Counsel-Advising your C-Suite as Cross-Border U.S. Tax & Corporate Counsel.
  3. Canadian international tax planning for businesses in Canada expanding globally, including digitally.
Select client work
  • Advised award winning architectural and design companies in Canada on the design and implementation of strategies for structuring their business, tax, and legal affairs to provide services to pre-eminent museums, universities, and governments across multiple states throughout the United States.
  • Acted as U.S. tax & corporate counsel for North American Israeli Tech Fund on the design and implantation of strategies to expand technology to over 20 states including complex transfer pricing and state legal and regulatory matters.
  • Acted as U.S. tax and corporate counsel for an award winning Canadian entertainment company with a $150 million in assets to design and implement various complex financial and business strategies including complex transfer pricing while working with senior management of principal investor ($100 billion fund).
  • Advised owner-entrepreneur business in Canada about federal and state tax and legal obligations for corporate entity and C-suite including beneficial ownership reporting under the Corporate Transparency Act and FinCEN.
  • Acted as U.S. tax and corporate counsel for MNE based in Canada in the global logistics industry (with sales over $30 million) to design and implement a tax optimized cross border business and legal structure in multiple states dealing with income tax, employer tax, and related legal matters (team lead for over 20 professionals including C-suite, attorneys, accountants and economists).
  • NOTE: Prior results do not guarantee a similar outcome. Each matter is unique, and the outcome depends upon the specific facts of your case.

IRS TAX PROBLEMS

I have been advising U.S. persons, including both U.S. citizens and U.S. residents, to become compliant with their U.S. federal tax and reporting obligations since 2006. I have represented U.S. persons in Canada, the United States, and the E.U. as well as in Asia. I have also advised U.S. persons who are uncertain about the correctness of their U.S. reporting and where applicable, assisted them to remediate their affairs and consider tax and legal optimization strategies going forward.
 
My U.S. clients often own foreign investments which may include interests in legal entities and structures (including in Quebec). I have represented clients through all stages of the Offshore Voluntary Disclosure Program and the Streamlined Foreign Offshore Procedures from 2009 to present (including both civil and criminal matters).
 
My representation to date has included advising clients on all aspects of U.S. immigration law relating to renunciation of American citizenship and abandonment of green cards. I work very closely with a U.S. based team of CPAs in the preparation of my clients’ U.S. individual and business compliance and I am considered a co-return preparer on all of my corporate and individual clients’ filings with the IRS. In advising clients who are also Canadian, my legal experience and knowledge of theIncome Tax Act (Canada) Canadian residency laws, and my book on the Canada-U.S. Tax Treaty [2,500 pages] has often been an indispensable asset to my client’s outcome.
 
Our Services:
  1. IRS voluntary disclosures forbusinesses in Canada and the U.S., including both income and employer taxes (private and public companies).
  2. State and local government voluntary disclosures (tax and legal problems) for Canadian businesses (private and public companies).
  3. IRS voluntary disclosures for individuals, estates and trusts, including streamlined foreign offshore procedures, appeals, and criminal matters.
  4. Advice on federal income tax, corporate tax, partnership tax, international tax, and international reporting forms, including assisting people who are unsure about their reporting or compliance with the IRS. Advice includes but is not limited to IRS Forms: 5471, 5472, 8621, 8938, 8833, 926, 3520, 8865, 1120F, 1120, 1040, 1040NR.
  5. Expatriation planning (U.S. Treasury & Immigration Law).
  6. Abandonment of green cards (U.S. Treasury & Immigration Law).
  7. We work closely with a team of U.S. based CPAs to provide cohesion between our legal advice and your filings.
Select client work
  • Advised C-suite of publicly traded company on TSX on strategies to remediate international corporate tax delinquencies in U.S. and multiple foreign jurisdictions.
  • Advised privately held global logistics corporation in Canada on remediating income and employer tax issues with federal and state and local agencies, including the design and implementation (with transfer pricing) of new tax optimized cross border business and legal structure.
  • Since 2006 I have represented numerous delinquent filers in Canada, the U.S. and the European Union (including U.S. citizens, green card holders, and estate executors) to remedy their problems through: voluntary disclosures, including under OVDP and OVDI and streamlined offshore procedures; IRS Appeals; and IRS tax relief procedures (for individuals for the reduction, elimination, or deferral of taxes, including penalty abatements).
  • Since 2006, I have represented numerous U.S. citizens in Canada and the E.U. to expatriate or to abandon their green cards, and for those clients retaining dual nationalities, to formulate new strategies to help preserve their wealth under both countries tax systems.
  • Advised U.S. citizens and U.S. residents in Canada and the U.S. on understanding and resolving complex and potentially devastating corporate tax problems they faced through their personal investments and private corporations under U.S. tax rules, including PFICs, partnerships (including Quebec), and transfer pricing rules.
  • Advised Canadian investors in U.S. real property on remediating tax deficiencies at the federal and state levels regarding their commercial holdings in rental properties.
  • Advised U.S. based services MNE with operations in 40 foreign jurisdictions on existential international corporate tax and foreign reporting problems with the IRS which the client and their tax advisors were unaware of and provided strategies to save the group and its owners from fiscal disaster.
  • NOTE: Prior results do not guarantee a similar outcome. Each matter is unique, and the outcome depends upon the specific facts of your case.

CROSS BORDER ESTATE PLANNING AND TAXATION

Families or individuals with international facts (individuals or assets touching more than one sovereign) may have traditional professionals such as accountants, wills lawyers, and financial planners to advise them. However, in my career as an international tax lawyer, I have seen many high net worth families and individuals experience grave financial harm from taxation, notwithstanding their support by this group of professionals.
 
A common thread running through these problems, which are often existential, is a failure to identify, understand, and deal with all of the relevant multi-jurisdictional tax law issues they face. Complex and costly international tax issues are often missed because professionals are not working as a coherent team and no one is seeing all of the important tax issues that are existing and needing attention.
 
Our Services:
1. Estate and tax planning for residents of Ontario:
  • with 1 or more U.S. citizen family members;
  • with children living in the U.S.;
  • with complex legal structures, e.g., trusts, corporations, partnerships, LLC’s;
  • with U.S. vacation property, art, securities or other U.S. situs assets;
2. Estate and tax planning for Canadian residents with siblings, parents, resident in the U.S.
3. Cross border gift and related tax planning for large gifts from Canadian families to their children in the U.S.
4. Tax advice for Ontario executors of estates with U.S. decedents including voluntary disclosures before the IRS for delinquent or non-filers.
5. Provide Canadian and U.S. cross border tax advice for your wills.
 
Select Client Work:
  • Advised families in Ontario on tax and legal strategies to make large cross border gifts to children and grandchildren living in the U.S. (including Dynasty trust).
  • Advised families in Ontario on cross border estate and tax planning and preparation of wills and trusts for their children living in the U.S., including involving complex cross border legal investment and business structures.
  • Advised families in Ontario on cross border estate and tax planning for U.S. vacation property, including: the establishment of cross border trusts, and strategies for the sale of vacation property in the U.S. to minimize withholding and income taxation.
  • Advised families (or individuals) in Ontario with parents (or a parent) living in the U.S. on cross border estate and income tax planning to minimize decimating tax consequences they face as inheritors/beneficiaries of their parent’s plans.
  • Advised families on revising wills made in Ontario (by other professionals), to avoid catastrophic cross border tax consequences on legal issues missed.
  • NOTE: Prior results do not guarantee a similar outcome. Each matter is unique, and the outcome depends upon the specific facts of your case.

U.S. IMMIGRATION AND TAX PLANNING

Our Services:
Pathways for residents of Canada to enter and work in the U.S. for business purposes,with integrated cross border tax and legal planning, including under the following visas:
  • L-1 Visa (Intra Company Transfer)
  • O-1 Visa (Individual of Extraordinary Ability)
  • E-1 Visa (Treaty Trader)
  • E-2 Visa (Treaty Investor)
  • TN Visa (Canadian Professional)
Select Client Work:
  • Advised award winning entertainment company in Canada on L-1 visa and related tax and legal strategies (including tax treaty and transfer pricing).
  • Advised award winning international design firm in Canada on E-1 visa and related federal and state tax and legal strategies (including tax treaty and transfer pricing).
  • Advised MNE in Canada providing global logistical services on E-2 visas and related tax and legal strategies (including treaty and transfer pricing).
  • Advised officer from C-suite of publicly traded company on cross border tax planning, post facto, to address potentially decimating tax consequences arising from U.S. immigration advice (received in a vacuum without timely and proper international tax planning).
  • NOTE: Prior results do not guarantee a similar outcome. Each matter is unique, and the outcome depends upon the specific facts of your case.

INTERNATIONAL TAX PROBLEMS WITH THE CRA

I work with my clients to help them identify their international (and related corporate and individual) tax problems under the Income Tax Act(Canada). I work closely with my legal team, to assess the combined substantive and administrative law aspects of a client’s case, (both civil and criminal) and develop strategies to deal with the CRA.
 
Due to the enormous complexity of the combined tax laws of Canada and the U.S., it is not uncommon for my clients to unknowingly have serious international tax problems which often include double or triple taxation of their income (or worse) due to their facts and lack of or poor initial tax planning (especially on residency).
 
Remediation of cross border tax problems with the CRA is only half the story. My clients also seek a cross border solution to prevent their problems from reoccurring and to make their structure tax efficient. I assist clients with a diverse range of international tax and reporting problems including involving complex cross border legal structures, offshore reporting (and Forms T1134, T1135), tax havens, permanent establishments, transfer pricing, and treaty law.
 

CANADIAN RESIDENCY AND TAX PLANNING

REGAN: "O, sir, to wilful men, The injuries that they themselves procure
Must be their schoolmasters." King Lear - William Shakespeare
 
In relocating from Canada or to Canada avoiding Shakespeare's maxim frequently requires a comprehensive understanding of both the Canadian tax rules and decades of jurisprudence surrounding Canada's residency system. Unfortunately, many of our clients in this area of Canadian international tax law failed to receive timely and proper counselling about their move.
Most of my books on international tax deal importantly with the subject of Canadian residence law and related treaty law.
 
Our residency tax planning is not for the feint of heart. Understanding our client's personal, economic, and business goals and requirements is of paramount concern. We work with our clients and to advise them and to create international tax strategies to support their journey. In Canadian residency planning whether you are a pro athlete, or a person relocating for business or family reasons, our clients understand "an ounce of prevention is worth a ton of cure."
 

NEW YORK ESTATE PLANNING

Our Services:
  • Wills and trusts (including revocable and irrevocable trusts)
  • Estate tax and gift tax planning
  • Generation skipping transfer tax planning
  • Planning for non-probate assets
  • Powers of Attorney for health and property
  • Elder law
  • Taxation of trusts
  • Income tax considerations
  • Irrevocable life insurance trusts