Your misconceptions
1. Unrealistic expectations regarding tax planning
1.1. Essence
The phrase «parked somewhere in the world» implies the possibility of artificial profit shifting without real economic substance.
This underlying assumption ignores the modern international regulatory landscape in which both the U.S. and Canada are actively combating such schemes.
1.2. Reasoning
1.2.1.
The OECD/G20 Base Erosion and Profit Shifting (BEPS) initiative requires that profits be taxed where economic value is created.
This has led to the implementation of Economic Substance requirements.
Using «shell companies» to «park» profits has become extremely risky.
1.2.2.
The U.S. Global Intangible Low-Taxed Income (GILTI) regime effectively imposes a minimum tax on a significant portion of the profits of controlled foreign corporations (CFCs), even if they are not distributed.
This significantly limits the benefits of U.S. tax deferral for U.S. shareholders on profits accumulated abroad.
1.2.3. Canada
1.2.3.1.
The primary mechanism for controlling the shifting of active operating profit out of Canada is the Transfer Pricing rules (Section 247 of the Income Tax Act).
These rules require strict adherence to the arm's length principle.
Profit must be allocated based on where the actual economic activity is performed and value is created.
If the key functions, assets, and risks are located in Canada, the corresponding portion of the operating profit must remain in Canada.
The Canada Revenue Agency (CRA) actively challenges attempts to artificially reduce the Canadian tax base through transfer mispricing.
Shifting profits without transferring the corresponding functions, assets, and risks will result in adjustments and significant penalties.
1.2.3.2.
Another key barrier is the Economic Substance requirements, reinforced by the General Anti-Avoidance Rule (GAAR), Section 245 of the Income Tax Act.
GAAR is designed to deny tax benefits arising from abusive tax avoidance.
According to recent amendments (Bill C-59, 2024), a significant lack of economic substance is «an important consideration that tends to indicate» the existence of an abusive transaction.
2. Conflict of strategic goals
2.1. Essence
The pursuit of aggressive tax planning (point 1 above) fundamentally contradicts the goal of creating a «simplified, investor-ready structure».
2.2. Reasoning
2.2.1.
Aggressive tax schemes require complex, multi-layered structures, often involving offshore jurisdictions.
This is the direct opposite of a «simplified» structure.
2.2.2.
Aggressive tax planning reduces financial transparency and distorts financial results.
This distortion occurs through artificial profit shifting, such as transfer mispricing (the manipulation of prices of intra-group transactions in violation of the arm's length principle).
This practice severs the link between reported profit and economic substance.
As a result, it is difficult for investors to assess the company's underlying performance, as the reporting does not reflect where value is actually created.
Investors expect reasonable tax efficiency but require transparency to assess risks.
They are averse to aggressive schemes that distort economic reality.
2.2.3.
Complex tax schemes increase tax risks (adjustments, penalties) and make the due diligence process for potential investors significantly more complex and costly.
High tax risk reduces the company's valuation.
3. Underestimation of the project's scale and complexity
3.1. Essence
The characterization of the project as «small-scale» contradicts the list of stated requirements and the context of the situation.
3.2. Reasoning
3.2.1.
A restructuring involving 2 different legal and tax systems automatically complicates the project.
3.2.2.
The project includes 6 diverse objectives, including the implementation of an OpCo/PropCo structure for the segregation of assets and operations and the carve-out of the brokerage business.
This requires coordinated work in corporate law, tax, and finance.
3.2.3.
The recent conclusion of the Subchapter V bankruptcy heightens both the complexity and the risks.
4. The illusion of guaranteed asset protection
4.1. Essence
A naive belief that the creation of a new legal structure ensures protection.
4.2. Reasoning
4.2.1.
The risk of piercing the corporate veil is significantly higher for closely-held corporations than for public corporations.
This is because in such companies there is often no real separation between the owners and the business («unity of interest»), which may lead courts to treat the company as an alter ego of the shareholders.
The key risk factors are commingling of personal and corporate assets, undercapitalization, and failure to follow corporate formalities.
4.2.2.
The recent bankruptcy may indicate past management or capitalization issues, which will attract heightened scrutiny from future creditors.