Our Services

A considered approach to
every dimension of wealth

We offer a deliberately limited range of services, each refined over nearly four decades of practice. Our commitment is not to breadth, but to depth — and to the belief that true wealth management is inseparable from the life it serves.

01

Wealth Management

Bespoke portfolio construction built around your specific objectives, time horizons, and tolerance for risk. We favour diversified, risk-adjusted strategies that compound steadily rather than chase short-term performance.


Client Scenario

A retired executive with $12M in investable assets approached us after growing frustrated with the constant portfolio churn at her previous firm. She wanted steady income, capital preservation, and the confidence that her wealth would sustain three generations. We constructed a portfolio blending investment-grade municipal bonds, blue-chip dividend equities, and select alternative investments — generating predictable income while maintaining long-term growth potential. Eight years later, her portfolio has grown modestly and reliably, weathering two corrections with minimal drawdown.

Investment Methodology

Our approach is rooted in fundamental analysis, long-duration thinking, and a deep suspicion of complexity for its own sake. We begin with a thorough understanding of your complete financial picture, then construct a portfolio that reflects your values, your obligations, and your vision for the future. We do not trade frequently. We do not chase momentum. We build portfolios the way careful stewards have always built enduring things — with patience, with discipline, and with a preference for quality over novelty.

Asset Allocation Approach

Every allocation decision flows from a single question: what does this family need their wealth to accomplish? For some, that means a conservative posture emphasizing capital preservation and current income. For others, it means a more growth-oriented strategy with exposure to global equities, private markets, and real assets. We allocate across traditional and alternative asset classes, across geographies and currencies, and across time horizons — always with an eye toward correlation, liquidity, and the interplay between risk and return.

Risk Management Framework

  • Stress-testing portfolios against historical crisis scenarios and hypothetical events
  • Monitoring concentration risk across holdings, sectors, and asset classes
  • Maintaining appropriate liquidity reserves for each client's near-term needs
  • Regular rebalancing guided by valuation discipline, not calendar-driven triggers
  • Transparent reporting on risk metrics alongside performance metrics
02

Estate Planning

Structuring the seamless transfer of wealth across generations. We coordinate with your legal counsel to ensure your legacy reflects your intentions precisely — preserving not just assets, but values, governance structures, and family cohesion.


Client Scenario

A second-generation business owner with $45M in family assets came to us facing a common dilemma: how to provide generously for his children and grandchildren without undermining their ambition or creating conflict. We worked alongside his attorneys to establish a dynasty trust, a family limited partnership, and a private foundation — each structure serving a distinct purpose in a cohesive estate architecture. The result was a framework that distributes wealth gradually, encourages productive engagement, and preserves the family's philanthropic commitments for generations to come.

Trust Structures

We help our clients evaluate and implement trust structures suited to their specific circumstances — revocable living trusts for simplicity and control, irrevocable trusts for estate tax reduction, generation-skipping trusts for multi-generational planning, and charitable remainder trusts for philanthropically minded families. Every structure is evaluated not just for tax efficiency, but for its alignment with the family's values and governance preferences.

Philanthropic Planning

For families with charitable inclinations, we design giving strategies that maximize both impact and tax advantage. This may include the establishment of private foundations, donor-advised funds, or charitable lead trusts. We work to ensure that philanthropy becomes a meaningful part of the family's legacy, often involving younger generations in grant-making decisions to instill a sense of stewardship and purpose.

Family Governance & Succession

  • Developing family constitutions and governance documents to guide future decision-making
  • Establishing family councils and meeting cadences for multigenerational communication
  • Business succession planning coordinated with operational and legal advisors
  • Education programs for rising generations on financial literacy and stewardship
  • Conflict resolution frameworks to preserve family unity through transitions
03

Tax Strategy

Proactive, year-round tax planning that goes well beyond compliance. We identify opportunities to minimise liability while preserving flexibility across jurisdictions — always in close coordination with your CPA and legal counsel.


Client Scenario

A technology entrepreneur who recently completed a $30M liquidity event faced a daunting tax exposure across federal, state, and AMT obligations. By implementing a pre-planned combination of qualified opportunity zone investments, charitable giving strategies, and strategic loss harvesting from existing positions — all coordinated months before the transaction closed — we reduced her effective tax rate by more than twelve percentage points while maintaining full compliance and transparency.

Year-Round Planning Approach

Tax planning is not an annual event — it is an ongoing discipline. We monitor legislative developments, review portfolio positions for harvesting opportunities, and evaluate each significant financial decision through a tax lens before it is executed. Our clients are never surprised at year-end, because we have been planning together all year.

Multi-Jurisdiction Considerations

For families with residences, businesses, or investments across multiple states or countries, we coordinate tax strategy to minimize the cumulative burden. This includes evaluating domicile strategies, state income tax planning, cross-border investment structures, and treaty-based planning for international assets. We work in close partnership with tax counsel in each relevant jurisdiction.

Charitable Giving Optimization

  • Timing charitable contributions to maximize deduction value in high-income years
  • Contributing appreciated assets to avoid capital gains while securing full fair-market-value deductions
  • Structuring charitable remainder trusts for income generation and deferred giving
  • Coordinating qualified charitable distributions from retirement accounts
  • Evaluating donor-advised funds for flexible, multi-year giving strategies
04

Retirement Planning

Defining what financial independence looks like on your terms. We model scenarios, stress-test assumptions, and build plans that adapt as your life evolves — because retirement is not a destination but a decades-long chapter.


Client Scenario

A couple in their late fifties with $8M in combined assets wanted to retire within five years but were uncertain whether their wealth could sustain their lifestyle across a thirty-year horizon — particularly given their desire to maintain residences in New York and the South of France. Through detailed scenario modeling that accounted for inflation, healthcare costs, currency exposure, and their philanthropic goals, we demonstrated that early retirement was not only feasible but could be achieved while still growing their estate for the next generation.

Scenario Modeling

We construct detailed financial models that project your wealth across multiple time horizons under a range of assumptions — optimistic, expected, and adverse. These models incorporate investment returns, inflation, taxation, healthcare costs, and your specific spending patterns. We update them regularly, so your plan evolves as your circumstances do.

Withdrawal Strategies

The order and manner in which you draw from various accounts can have a dramatic effect on the longevity of your wealth. We design withdrawal sequences that optimize across taxable, tax-deferred, and tax-free accounts — coordinating with Social Security timing, required minimum distributions, and Roth conversion opportunities to minimize lifetime tax exposure.

Lifestyle Planning

  • Defining desired retirement lifestyle and translating it into sustainable spending levels
  • Planning for healthcare costs including long-term care contingencies
  • Evaluating real estate decisions — downsizing, second homes, or relocation
  • Integrating legacy goals so retirement planning and estate planning work in concert
  • Adjusting plans for life transitions — health changes, family needs, new interests
The Oakwood Process

Five steps from conversation
to ongoing stewardship

Step One

Discovery

A confidential conversation to understand your complete financial picture, your family dynamics, your values, and your long-term aspirations. We listen far more than we speak.

Step Two

Analysis

Our team conducts a thorough review of your current holdings, liabilities, tax situation, estate documents, and insurance coverage to identify opportunities and vulnerabilities.

Step Three

Strategy

We present a comprehensive, written wealth plan addressing investment management, tax strategy, estate planning, and retirement projections — tailored entirely to your situation.

Step Four

Implementation

Coordinating with your existing advisors — attorneys, accountants, insurance specialists — we execute the plan methodically, ensuring every element works in concert.

Step Five

Ongoing Management

Regular reviews, proactive communication, and continuous refinement. Life changes — and so must your plan. We are your partner through every transition.

Fee Transparency

Honest counsel begins
with honest terms


We believe that the relationship between advisor and client must be built on absolute transparency — beginning with how we are compensated. Our fee structure is designed to align our interests with yours, to eliminate conflicts, and to ensure that every recommendation we make is motivated solely by what is best for your family.

We do not earn commissions. We do not accept referral fees from third-party product providers. We do not profit from transaction volume. Our compensation is derived entirely from the advisory fees our clients pay directly, which means our only incentive is to grow and protect your wealth.

  • Asset-Based Advisory Fees

    Our primary compensation is a percentage of assets under management, calculated on a tiered, declining scale. As your portfolio grows, your effective rate decreases — our interests remain aligned.

  • No Hidden Costs

    There are no account opening fees, closing fees, or transfer fees. Custodial costs and fund expense ratios are disclosed in full. You will never discover a charge we have not explained in advance.

  • Financial Planning Included

    Comprehensive financial planning — including retirement modeling, tax strategy, and estate coordination — is included in our advisory relationship at no additional cost.

  • Clear Reporting

    Quarterly performance reports include a detailed breakdown of all fees paid, so you always know exactly what our services cost. We welcome the scrutiny.

Next Step

Ready to explore what a
considered approach could mean
for your family?

Request a Consultation