Strategic Tax Guidance for Wealth Builders

High-Net-WorthTax Planning

Effective tax planning should be as dynamic as your financial life. We bring thoughtful, proactive strategies built around your unique profile—whether you're a seasoned executive, business owner, or part of a multi-generational family office.

Our Philosophy

Tailored Planning, Not Templates

We don't leverage generic templates or cookie-cutter strategies. Every plan is carefully customized after a close review of your complete financial picture.

As your dedicated high-net-worth tax advisor, we bring focus beyond annual filings. We present year-round smart strategy tailored to your distinct investment profiles, income streams, and personal goals.

Custom Strategy
Year-Round Focus

Tailored Planning

Every plan is carefully customized after a close review of your complete financial picture.

Year-Round Strategy

Proactive planning that adapts to your changing financial landscape in real time.

Team Integration

Seamless coordination with your attorney, investment manager, and internal staff.

Comprehensive Tax Strategy Elements

Our team delivers strategic planning across all aspects of high-net-worth tax considerations

Multi-Source Income Planning

Aligning W-2 wages, K-1 earnings, dividends, and equity compensation for optimal tax efficiency.

W-2 wage optimization and timing strategies
K-1 partnership and S-corp income coordination
Dividend and interest income planning
Equity compensation timing and structuring

Investment Tax Strategies

Tax-loss harvesting and capital gain planning with coordination across your portfolio managers.

Strategic tax-loss harvesting throughout the year
Capital gain timing and deferral strategies
Portfolio manager coordination and communication
Asset location optimization across account types

Family Trust & Estate Tax Planning

Creating structures that respect your legacy and reduce unnecessary tax burdens.

Trust structure design and implementation
Estate tax minimization strategies
Generation-skipping transfer tax planning
Legacy preservation and wealth transfer

Entity Design & Structure

S-corps, partnerships, and family limited partnerships used with strategic purpose.

Optimal entity selection and formation
Family limited partnership structures
S-corp election timing and benefits
Multi-entity coordination and management

Philanthropic Strategy

Incorporating charitable giving into your comprehensive tax and wealth plan.

Charitable remainder trust planning
Donor-advised fund strategies
Private foundation establishment
Tax-efficient giving structures

Who We Serve

We understand that our clients lead busy, high-stakes lives requiring sophisticated tax strategies

C-Suite Executives

Executives dealing with stock options, performance bonuses, and complex compensation packages requiring strategic planning.

Business Owners

Entrepreneurs and business owners managing multiple income streams and planning for potential exits or expansions.

Family Office Members

Multi-generational families coordinating complex estates and wealth preservation strategies.

Real Estate Investors

Individuals managing large real estate holdings with complex depreciation and income timing considerations.

Specialized Planning Areas

We provide comprehensive tax planning across complex income sources and investment structures that high-net-worth individuals encounter.

1

Stock-Based Compensation Events

Strategic planning for RSUs, ISOs, NSOs, and other equity compensation structures.

2

Capital Gains from Asset Sales

Optimizing tax treatment for business exits, real estate sales, and investment dispositions.

3

Cross-Border Income Optimization

Foreign tax credit optimization and international income structuring.

4

Alternative Investment Tax Treatment

Crypto asset reporting and complex investment vehicle tax planning.

5

Income Smoothing & Timing

Year-over-year income optimization and strategic timing strategies.

Dynamic Strategy Adaptation

As high-net-worth tax advisors, we take the long view. Your tax profile changes as your assets grow, and we're ready to adapt the strategy in real time.

Portfolio Growth
Adaptive
Tax Regulations
Current
Strategy Updates
Real-Time

Concierge-Level Attention

Discretion, clarity, and responsiveness define our performance. You'll always have access to a senior advisor who knows your file—not a rotating cast of unfamiliar names.

Discretion & Trust

Confidential handling of your sensitive financial information with the highest professional standards

Responsive Service

Quick response times and proactive communication throughout the year, not just during tax season

Senior Advisor Access

Direct access to experienced professionals who understand your complete financial picture

From the starting point, we design a roadmap that aligns with your specific needs. Our job is to find opportunity within the tax code—not add to your stress.

Why Richmond Street Advisors?

Choosing the right high-net-worth tax advisor is about trust, not transactions. Clients return to Richmond Street Advisors because we bring clarity to a system that often feels opaque.

We present strategy, not products

What Our Clients Appreciate Most

Year-round communication, not just during tax season
Direct access to experienced advisors—not junior staff
Strong grasp of tax implications across industries and asset types
Practical solutions that align with long-term targets
Coordination with your existing financial team

When you work with Richmond Street, your high-net-worth tax advisor becomes an extension of your financial team. We coordinate with your attorney, investment manager, and internal staff as necessary.

Every conversation, every update, and every filing is managed with the same level of care we would expect for our own families.

Take the First Step Toward Smarter Tax Strategy

Your time is valuable, and our goal is to maximize the return on it. We focus on impact without cutting corners, bringing clarity and opportunity to your complex financial landscape.