Working With Mainsail

Selecting the right wealth management team is an important decision. Our onboarding process is designed to help you understand our team’s approach, philosophy, and expertise—so you can experience firsthand what it’s like to partner with us and how we can make a difference together.

Book an Initial Conversation
1

Introduction

Meet our team, learn about our approach, and explore how we serve clients.

2

Discovery

Share your financial picture with us; we clarify your goals and create a tailored action plan.

3

Planning

Once we decided to work together, we will deliver a comprehensive action plan and establish objectives for moving forward.

4

Investments

We walk through how we’ll manage your accounts and align investment strategy with your plan.

5

Implementation

Once we’ve agreed on the priorities, our team puts your plan into action and ensures a seamless onboarding experience.

Who We Are

Mainsail is a boutique, multi-generational wealth management firm serving a select group of highly successful families and business owners.

  • Experience & Credentials: Our lead advisors average nearly two decades of industry experience and hold advanced designations including CFP®, CFA®, CWS®, and CRPC®.
  • Team-Based Approach: Your lead advisor ensures your priorities are understood and executed, with the strength of our full advisory team behind every decision.
  • Long-Term Relationships: Our team builds lasting relationships, often guiding multiple generations of a family, ensuring that your financial strategy evolves seamlessly as your life and goals change.
  • Concierge-Level Service: A high-touch, white-glove approach that ensures your priorities are understood, your professionals are aligned, and your plan is executed seamlessly.
  • Select Client Base: By working with a select number of client families, each lead advisor can devote the attention required to truly understand their needs and deliver thoughtful solutions.
  • Beyond One-to-One: Unlike firms built around a single advisor, Mainsail is designed to provide long-term stability and a collaborative team that knows your goals inside and out.

We coordinate as a team so decisions are faster, better, and consistent with your plan.

Mainsail team

Comprehensive, Concierge-Level Planning

Every Mainsail client works with a dedicated lead advisor—supported by the collective strength of our multi-generational team. Your lead advisor is your central point of contact, drawing on the right specialists within our firm whenever unique needs arise. Depending on your needs, we also coordinate with outside professionals such as CPAs and attorneys, ensuring your broader financial picture is always aligned.

Our planning is comprehensive and ongoing—not a one-time plan. With over a decade of advisory experience per lead advisor and the continuity of a multi-generational team, we have the expertise to identify and solve both everyday strategies and complex planning scenarios. We meet with our clients consistently throughout the year to review progress, stay aligned on goals, and adjust plans as life evolves. And because our advisors work hand-in-hand with our in-house investment committee, your plan and portfolio always move in lockstep.

Tax Strategy

Executive Compensation, Business Exit Strategies, Roth conversions, tax-loss harvesting, asset location, and so much more

Estate & Legacy

Trust coordination, beneficiary design, generational gifting.

Retirement Planning

Income strategy, Social Security timing, Medicare planning, cash-flow design.

Risk Management

Concentrated equity strategies, Insurance reviews, long-term care, asset protection.

Business Planning & Lending

Succession, key-employee comp, SBL/structured lending.

Charitable & Family Giving

DAFs, private foundations, QCDs, family engagement.

Investment Management Summary

We believe wealth should be managed with a steady hand and a thoughtful eye toward opportunity. Our team builds portfolios designed for long-term success, while making tactical adjustments when markets shift— so clients can stay invested with confidence. By managing strategies in-house, we can explain every decision, control for taxes and income needs, and deliver solutions that fit each family’s unique picture.

Our investment team manages most client portfolios internally with full discretion. That matters to you because it allows us to:

  • Tighter tax integration: Align portfolios with your plan so we can manage gains, losses, and income needs more effectively.
  • Nimble decisions: Our Investment team can act quickly during volatility or to raise cash for client needs.
  • Personalized design: Strategies are built around your specific goals—not an institutional playbook.
  • Direct accountability: We own the results and can explain every holding down to the individual security level.
  • Expanded capabilities: From custom stock strategies to retirement income design, we offer solutions few firms our size can match.
Mainsail Investment Committee

How We Manage Investments

A disciplined cadence keeps portfolios aligned with client goals and market conditions—combining strategy, research, and responsiveness.

Weekly & Monthly Committee Meetings

The Mainsail Investment Committee meets on a consistent basis to review markets, risk, and model positioning.

Dedicated Analyst

Continuous monitoring of economic data, earnings, and sector trends.

12+ Models

Diversified strategies across equity, fixed income, asset allocation, alternative investments, and income-focused portfolios.

Specialized Managers

We selectively integrate outside managers where their expertise complements ours and broadens client opportunities.

Continuous Oversight

We make sure your portfolio adapts in real time so your plan stays on track, your income needs are met, and you never have to worry about the details.

Once You’re Ready, We Make the Transition Seamless

We coordinate each step so your accounts move smoothly—and you know exactly what to expect.

  • Clear service model: what to expect monthly, quarterly, and annually.
  • Paperwork handled: our team prepares and processes all transfer documents end-to-end.
  • We cover transfer fees*: typical transfer charges are covered to make moving easy.
  • Plan-led investing: your financial plan guides how accounts are managed.
  • Anytime access: online portal and paper statements—your choice.
  • Respected custodian: Raymond James Financial Services (Member SIPC).

*Excludes surrender fees on certain investments; we’ll fully disclose any before proceeding.

Agreement & Kickoff

Once you decide to move forward, our team takes it from here—setting a timeline, answering questions, and making sure you know exactly what to expect.

Paperwork & Transfers

We prepare and process all paperwork on your behalf. Cost basis records move with your accounts, and we track any RMDs already taken so there are no year-end surprises. Residual dividends and interest are monitored and swept automatically as they settle.

Retirement Account Coordination

For 401(k)s and other retirement plans, we work directly with custodians to ensure pre-tax and after-tax assets are handled properly, avoiding unnecessary tax burdens. We also coordinate any deposits or withdrawals to prevent disruptions.

Set Up & Access

Once accounts are funded, we establish your online access, integrate your financial plan, and connect your investments—giving you full visibility and confidence from day one.

Down to the Last Detail

We confirm that all assets, dividends, and interest have arrived correctly, reconcile accounts, and ensure reporting is accurate. The transition isn’t complete until everything is fully settled.

Two Offices, One Seamless Experience

Meet in person in Gloucester or Richmond — or virtually, if you prefer.

Gloucester

6641 Main Street
Gloucester, VA 23061


View Map

Richmond

4510 Cox Road,
Suite 103
Richmond, VA 23060

View Map

Virtual

Secure video meetings and digital onboarding for clients who prefer remote coordination.


Recognition & Partnerships

Consistently recognized by respected publications. Fiduciary, fee-based advice. Boutique service paired with the strength and stability of Raymond James.

Ready to explore fit?

Schedule a brief introductory conversation with our team.

Book an Introductory Meeting