Client

Case Studies

At Caraway Management, our work is defined by the ability to navigate complexity and deliver structured, measurable outcomes. The following case studies illustrate how we support clients facing multi-jurisdictional challenges, concentrated risk, and significant liquidity events.

The Cross-Border Expat

Client: Daniel L. (Canadian, based in London)

The Problem

Daniel, a 42-year-old finance professional, had built his career across Toronto and London. Over time, his financial situation became fragmented. He held investment accounts in Canada and the UK, maintained two separate pension schemes, and earned income in GBP while retaining liabilities in CAD.

This created several challenges:

  • Exposure to currency volatility between GBP and CAD
  • Overlapping tax obligations across jurisdictions
  • Limited visibility across his total net worth
  • Inefficient pension structures, including a dormant plan in Canada
The lack of coordination increased administrative burden and introduced unnecessary financial risk.

The Solution

We implemented a unified cross-border strategy designed to simplify and optimize Daniel’s financial structure.

Key elements included:

  • Consolidating eligible pension assets into a Qualifying Recognised Overseas Pension Scheme (QROPS), improving flexibility and long-term tax efficiency
  • Structuring a multi-currency portfolio, aligning GBP assets with UK expenses while maintaining CAD exposure for future optionality
  • Coordinating with tax advisors in both jurisdictions to optimize treaty benefits and eliminate double taxation
  • Centralizing reporting to provide a consolidated view of assets and performance

This approach transformed a fragmented structure into a coordinated system aligned with Daniel’s long-term objectives.

The Outcome

Within 18 months, Daniel achieved:
  • A 27% reduction in overall tax leakage across jurisdictions
  • Improved currency alignment, reducing FX-related volatility by approximately 20%
  • Consolidation of pension assets, lowering administrative complexity and fees by 15%
  • Full visibility across his global balance sheet, enabling more effective decision-making

The result was a streamlined financial framework, allowing Daniel to focus on his career progression without the distraction of cross-border inefficiencies.

Client: Markus H. (German, based in Frankfurt)

The Problem

Markus, a 47-year-old senior executive at a publicly listed technology firm, had accumulated a substantial portion of his wealth through restricted stock units (RSUs) and performance bonuses.

Over time, this resulted in:

  • Over 65% of his net worth concentrated in a single stock
  • Exposure to company-specific risk and market volatility
  • Irregular income patterns tied to vesting schedules
  • Potentially significant tax liabilities upon liquidation

Despite strong career success, Markus faced a structural imbalance that could materially impact his long-term financial security.

The Solution

We developed a systematic diversification and liquidity strategy, designed to reduce concentration risk while managing tax exposure.

This included:

  • Establishing a structured 10b5-1 selling plan, enabling disciplined, rule-based divestment over time
  • Phasing sales across multiple tax years to avoid pushing income into higher marginal tax brackets
  • Reallocating proceeds into a diversified portfolio across equities, fixed income, and alternative investments
  • Introducing income-generating assets to stabilize cash flow

The strategy emphasized consistency and discipline, avoiding reactive decision-making during periods of market volatility.

The Outcome

Over a three-year period, Markus achieved:

  • Reduction of single-stock exposure from 65% to 28% of total net worth
  • Stabilization of annual income, with a 35% increase in predictable cash flow
  • Mitigation of downside risk, reducing portfolio volatility by approximately 22%
  • Efficient tax management, lowering realized capital gains tax impact by an estimated 18% compared to a lump-sum sale
Markus transitioned from a concentrated, high-risk position to a balanced and resilient portfolio, better aligned with long-term objectives.

Client: Alexandre B. (French, based in Paris)

The Problem

Alexandre, a 54-year-old entrepreneur, had built and scaled a successful manufacturing business over two decades. As he began considering a sale, several challenges became apparent:

  • The majority of his wealth was tied to a single illiquid asset
  • Limited pre-sale structuring had been implemented
  • Exposure to high capital gains taxation in France
  • No formal estate plan in place to manage future wealth transfer

Without proactive planning, a significant portion of the proceeds risked being lost to taxation, while the transition of wealth to the next generation remained uncertain.

The Solution

We initiated a pre-sale planning strategy several years in advance of the anticipated transaction.

This included:

  • Establishing a holding structure to optimize tax treatment of the eventual sale
  • Introducing trust-based elements to support long-term estate planning and control
  • Diversifying a portion of retained earnings into a global investment portfolio prior to exit
  • Coordinating with legal and tax advisors to ensure compliance with French and EU regulations

The objective was to maximize net proceeds while preserving flexibility and control over future wealth distribution.

The Outcome

Following the successful sale of the business, Alexandre achieved:

  • A 22% improvement in net after-tax proceeds compared to an unstructured sale scenario
  • Immediate diversification, with over 70% of net worth reallocated into a balanced portfolio
  • Establishment of a clear estate framework, reducing future inheritance tax exposure
  • Enhanced liquidity, enabling both personal flexibility and strategic reinvestment

The transition from business owner to investor was executed with clarity and control, preserving both capital and long-term legacy.

Client: Philippe D. (French, based between Paris and Singapore)

The Problem

Philippe, a 58-year-old business owner, had accumulated significant wealth across multiple jurisdictions, including France, Switzerland, and Singapore. His children were living in different countries, each with distinct legal and tax frameworks.

This created a complex estate planning challenge:

  • Exposure to forced heirship rules under French law, limiting flexibility in asset distribution
  • No coordinated structure for cross-border asset transfer
  • Multiple wills drafted independently, with potential for legal conflict
  • Significant potential inheritance tax exposure across jurisdictions

Without a unified framework, Philippe faced the risk of delays, disputes, and inefficient transfer of wealth to the next generation.

The Solution

We implemented a family office-style estate structure, designed to provide control, clarity, and tax efficiency across jurisdictions.

Key elements included:

  • Establishing separate, jurisdiction-specific wills, ensuring assets in France, Switzerland, and Singapore could be administered independently and efficiently
  • Introducing a trust structure in a common law jurisdiction, allowing greater flexibility in asset distribution and mitigating the rigidity of French forced heirship rules
  • Coordinating with legal and tax advisors to align the estate plan with international inheritance laws and tax treaties
  • Creating a governance framework to guide future decision-making and family involvement

This approach provided a cohesive structure while respecting the legal requirements of each jurisdiction.

The Outcome

Over a two-year implementation period, Philippe achieved:

  • A projected 30% reduction in inheritance tax exposure across jurisdictions
  • Elimination of potential legal conflicts between estate documents
  • Improved administrative efficiency, reducing expected probate timelines by 40%
  • A clear and enforceable framework for intergenerational wealth transfer

The result was a structured and controlled transition plan, ensuring that family wealth could be preserved and transferred without unnecessary friction or uncertainty.

Client: Luca R. (Italian, based in Milan)

The Problem

Luca, a 39-year-old professional in the Fin-Tech sector, had built a strong portfolio of public equities and real estate. However, he recognized several limitations:

  • Heavy reliance on public markets, with increasing volatility
  • Limited exposure to high-growth private companies
  • Portfolio returns closely correlated with major indices
  • Growing concern about inflation eroding long-term purchasing power

Despite a solid foundation, Luca’s portfolio lacked diversification into alternative growth drivers.

The Solution

We designed a portfolio transformation strategy, introducing private market investments to enhance diversification and return potential.

This included:

  • Allocating capital to private equity funds focused on high-growth sectors such as technology and healthcare
  • Providing access to pre-IPO opportunities, allowing participation in companies before public listing
  • Incorporating selective IPO allocations to capture early-stage public market growth
  • Structuring commitments across multiple vintage years to manage risk and liquidity

The strategy emphasized disciplined allocation, ensuring that private assets complemented rather than replaced existing holdings.

The Outcome

Within three years, Luca achieved:

  • Allocation of 32% of his portfolio to alternative assets, significantly improving diversification
  • Reduction in overall portfolio correlation to public markets by approximately 25%
  • Enhanced return profile, with private market investments contributing an additional 4.5% annualized return
  • Improved inflation resilience through exposure to growth-oriented, non-listed companies

Luca’s portfolio evolved from a traditional structure into a more resilient, forward-looking allocation, better positioned to capture long-term opportunities beyond public markets.

Disclaimer

These case studies are illustrative in nature. All client examples have been anonymized and represent a composite of real-world scenarios. While the situations reflect genuine challenges, specific details have been adapted for confidentiality and clarity. The outcomes described are not guarantees of future results but are intended to demonstrate the types of strategies and solutions that may be implemented under comparable circumstances.

Caraway