Transforming Emerging Wealth into an Enduring Legacy

Insights from Citizens' Women in Venture Retreat

By Caroline Hale, Private Bank Managing Director and Rick Gordon, Private Wealth Senior Managing Director

Citizens Private Wealth recently hosted a dynamic conversation on how to turn expanding wealth into lasting impact for your family, your future, and generations to come.

In this article, we’ll highlight the most powerful insights from the event and share a practical guide to help ensure the same success for your personal balance sheet as your portfolio companies.

What we heard: Building dynasties requires alignment within the family

Today's venture capitalists are quick to back bold ideas. Applying that same mastery to their personal finances and family legacy is where dynasties begin. That was the core theme of our panel featuring Amy Castoro (The Williams Group), Lindsay Chamings (Andersen Tax), and Rick Gordon (Citizens Private Wealth).

Before you transfer wealth, transfer purpose:

Most wealth transfers fail, not because of tax issues or investment gaps, but because families never talked about wealth. Amy Castoro of The Williams Group shared that generational wealth transfers often fail due to a lack of communication and financial literacy.

The fix? Start talking early. There's no need to talk about balances. Start the conversation with the responsibilities. Build literacy.

Plan before complexity takes over:

The key: Be proactive, not reactive.

That means laying the groundwork early:

• Revocable trusts
• Entity structures
• Gifting strategies

Don't wait for an exit to get organized. Have the right vessels in place before the carry is realized.

Know the tax rules before triggering a tax surprise. Lindsay Chamings of Anderson Tax flagged common surprises around QSBS and rollovers, and unexpected gains that create tax bills without available cash.

Sometimes simple beats brilliant:

• Before liquidity has been accumulated, simplicity often wins. Rick Gordon of Citizens Private Wealth reminded attendees that the best wealth strategies aren't always flashy. In fact, highly creative strategies will often restrict, rather than build, financial independence.
• Think barbell. That might mean pairing risk-heavy venture exposure on the professional side with more stable holdings, like muni bonds, ETFs, and tax-efficient diversification, on the personal side.
• The real test? Lifestyle IRR. Some tax strategies look smart on paper, but fail when they force dramatic changes to how you actually live.

“Keep it simple. Let it be liquid until you start reaching a place where that liquidity has offered you enough financial independence.” — Rick Gordon (Citizens Private Wealth)

Your Legacy Planning Guide

A Practical Framework for Building Long-Term Financial Strength and Family Alignment

This guide is designed for venture capitalists, fund managers, and entrepreneurs who are ready to turn financial success into a lasting legacy. Whether you're preparing for a liquidity event, managing carry, or thinking about how to align your wealth with your values, these steps will help you move forward with clarity and purpose.

1. Discuss Your Financial Picture with Key Family Members

Why it matters:

According to The Williams Group, a primary culprit of failures in generational wealth transfers is lack of communication.

What to do:

Involve spouses and children in age-appropriate ways.

Start conversations early. These conversations can be difficult. It can help to communicate responsibilities rather than discussing dollar amounts.

Focus on building financial literacy in the family and ensure children understand the purpose behind the wealth.

Children are often unaware of the advisors that help manage finances. Make sure they know who to trust.

2. Meet with a Financial Advisor to Plan Ahead

Why it matters:

Your personal balance sheet should support your life, not the other way around.

What an advisor can help with:

Build a barbell strategy: pair high-risk venture exposure with stable, liquid assets.

Prioritize liquidity to maintain flexibility when planning for capital calls, real estate, and lifestyle needs.

Use tax-aware borrowing (e.g., taking out a mortgage shortly after buying a home with cash to preserve interest deductions).

"If it sounds really creative, and it sounds like really unique, it's probably not great. It probably encumbers you, it probably restricts you, it's probably illiquid." — Rick Gordon (Citizens Private Wealth)

3. Connect with a Qualified Tax Advisor or Attorney Before You Need One

Why it matters:

Tax planning for carry, QSBS, and fund structures is complex. Waiting until after a liquidity event is usually too late.

What to do:

Engage a tax advisor familiar with PE/VC structures.

Plan for QSBS eligibility, rollovers, and tax-efficient exits.

Prepare for upcoming changes in tax law (e.g., the Tax Cuts and Jobs Act sunset).

Structure your assets early before the gains are realized.

"You're not going to have time to assess a tax advisor when a deal comes up. You need someone lined up before it happens." — Lindsay Chamings (Andersen Tax)

4. Structure Your Carry and Gifting Strategy

Why it matters:

Carry is a powerful tool for wealth creation, but only if structured correctly.

What to consider with carry:

Avoid surprises: understand your tax waterfall and distribution timing.

Plan for tax liabilities that may pop up before investment gains are realized.

Consider gifting carry early for estate planning.

Use irrevocable trusts to transfer future appreciation.

5. Define Your Family's Purpose and Legacy

Why it matters:

Legacy is more than the balance sheet. Explore your families' values and impact.

What to do:

Host family meetings to discuss shared purpose.

Use philanthropy to teach values and decision-making.

Align giving with your family's mission.

Consider donor-advised funds or foundations for long-term impact.

Final Thought: Start Early, Build Your Bench, and Stay Agile

Legacy planning isn't a one-time event. Start early, revisit often, and stay agile as your life, family, and goals evolve.

At Citizens Private Wealth, we specialize in helping clients build the right bench, connecting you with trusted advisors in tax, estate, investment, and philanthropic planning. Whether you're navigating your first liquidity event or preparing for multigenerational wealth transfer, our team is here to grow with you. We offer personalized, comprehensive strategies that evolve alongside your career, your family, and your vision for the future.